[BidClub_]
Invest Like the Best · · 114 min

How This VC Went From Broke to Becoming the Hot Hand in Silicon Valley

Patrick O'ShaughnessyRamtin Naimi

YouTube
TL;DR
  • Abstract's founding thesis: strip out Uber and Roblox (both seeded by First Round) and it was "close to impossible" to find a $5B+ power-law company whose seed round was led by a seed fund — Sequoia seeded Stripe, Airbnb, Dropbox and Nubank; Andreessen led first institutional rounds for Okta, Databricks and Slack; Khosla seeded Instacart and DoorDash; Index seeded Robinhood and Figma; Lightspeed seeded Snap and (he thinks) AppDynamics. Seed funds claiming proprietary deal flow were "mostly kidding themselves. They're a little delusional" — so Naimi built a seed firm aligned with the multi-stage platforms rather than against them.
  • The repricing math behind everything: roughly 1,000 seed deals got done 2008–2011, and an equal check into every one would have returned 3,000x on Uber alone — a 3x net fund for blanketing the entire market. "There is no world in which you could blanket an asset class and generate a 3, 5, 7x" — proof seed was too cheap, and why entry floors should be 3–5x higher. At today's ~$25M average entries, blanketing merely breaks even: "now you actually need to be better at picking than you were historically."
  • Ownership as a relative, not absolute, metric: his 5% from a $100M fund versus a co-lead's 15% from $1.5B is 5x the look-through exposure — "people ask me if I had an index approach. I'm like, it's the opposite of that." In 94% of fund-one companies, no venture fund anywhere offered more look-through ownership. Abstract now leads 80–90% of its deals and claims the highest seed-to-Series-A graduation rate to a tier-1 firm "by a pretty wide margin."
  • The product is lowering founders' future cost of capital: Naimi runs the entire Series A raise as the sole node — deck, data room, mock pitches, direct GP intros, all meetings in a 3-day window, nightly feedback. Result per his data: highest-decile A valuations, lowest average dilution, and at a $2B exit an extra ~$200M in the founder's pocket — "I can't personally think of a single value-add that a venture capitalist brings to the table that translates to more."
  • The 2021 warning: in the last six months he's funded seven companies that raised Series As within weeks at 4–5x his entry price with "not a whole lot of fundamental business progress," and his latest funds are printing 30–40% IRR within months of deployment when they should be in the J-curve. "The industry is getting a little drunk on IRR." On AI valuations themselves he refuses a verdict for 3–4 years: 20x growth decaying to 10x has no established fair multiple, and application-layer companies can become obsolete overnight when they become a feature of a foundation-model company.
  • Staying private is a deliberate productivity throttle: "early liquidity was the bug and not the feature of crypto — people got rich too quickly and stopped building things." When Google went public, over 100 people made millions and "92 of them were never heard of again." Today's 1–5% tender offers buy a down payment, not generational wealth — great for company building, "problematic from a venture returns perspective," with continuation vehicles as the emerging fix.
  • The art world runs on venture mechanics: the big four galleries (Hauser, Gagosian, Zwirner, Pace) are the platform funds, smaller galleries are the seed spotters, and graduation to a blue-chip gallery quadruples prices — "nicer to pay 25% of the cost." Masterpiece is a power law inside a single artist's output: one painting in a 12-work show is the one everyone fights over, which is why one Picasso sells for $5M and another for $100M.
  • The biography is the pitch: bankrupt at 24 (Chapter 13) after self-funding a marketplace-lending exchange straight into the sector's collapse, then 47 deals in 10 months via AngelList — first syndicate (Ripple) filled $470k in four hours; SPVs have returned ~$100M — before selling a stake in his management company to a consortium likely including Andreessen, Ovitz, Ackman and Sacks with a seven-year sunset. Abstract is now just shy of $2B AUM. "I don't think there is any excuse saying that you can't start a venture capital firm with no money."
Digest · the substance, structured for research

1. The art market is venture with paint: same structure, same graduation trade

  • Naimi's route in was social, not academic: mentors Michael Ovitz and Stuart Peterson would spend "two, three hours walking you around their home" narrating their collections, and he wanted a hobby he and his wife could share — "art collecting seemed like it could be golf for both me and my wife." He collects living contemporary artists in three generational buckets (mid-60s/70s, late-40s/50s, and his own 28–38 cohort), used an adviser only briefly, and concluded "you're better off doing the majority of the work yourself."
  • His structural read: at any moment ~50 important practicing artists are represented by the big four — Hauser, Gagosian, Zwirner, Pace — and once signed they're blue chip, with prices that sustain because those galleries have the clients and institutions to "control the markets for those artists." Beneath them sit the same recurring smaller galleries who discovered the talent first — exactly like the seed firms the big platforms cultivate for early deal flow.
  • The trade is the graduation: find galleries with a high "graduation rate" to the mega-galleries, buy before the jump, and "as soon as that happened, their prices basically quadruple … it's nicer to pay 25% of the cost of something versus full value." But not every artist graduates — "that's when you have to start applying some of your own judgment and hope you have the right taste."
  • The market has repriced like venture did: 20–25 years ago entry-level art was $10,000 and you could take a painting home for two weeks and bid 20–25% under ask; now big galleries carry 75–80 artists (versus 10–15 historically), he gets ~30 exhibition previews a day, and one mentor's rule stings — he's "never bought a painting for less than $100,000 that he's made any money on."

2. Masterpiece is a power law inside one artist's output

  • The highest-scoring collection on the list that ranks collections by the means at which they were built wasn't Cohen's or Griffin's — Patrick's quip, which Naimi endorsed: "it's like a low IRR collection" when you can buy anything. It was a postman and a librarian who spent 1960s weekends buying Pollocks and Rothkos on pure eye, before any value was assigned, and gave it all to museums.
  • Within any new show of 12 paintings, "there's probably one that's incredible that everyone's going to be fighting over, two that are really good, and the rest is kind of just… the gallery was like, we could sell 12 of them." The dramatic appreciation accrues to the best examples — why one Picasso clears $5M and another $100M. Ovitz's edge was discipline: maybe only three Picassos, "but the three best Picassos ever," rather than accepting consolation prizes.
  • His value screen: art cycles predictably — "things that were iconic 20 years ago tend to be undervalued 20 years later, then get very highly valued 30 to 40 years later." The undisputed iconic bodies of the '90s and 2000s (Richard Prince's Cowboys and nurses, Tracey Emin) skew white-male and out of fashion — "not a lot of demand for their work, but a really good buying opportunity." Counterweight: check collector-base depth — if everyone collecting an artist is 30–40 years older, "am I going to be the only person collecting this artist in 20 to 30 years?"
  • The unifying skill is Ovitz's phrase, frame of reference: "the more companies you meet, the easier it gets to discern what the better companies are. The more art you look at by a specific artist, the easier it becomes to identify what a great example is." The tell of a masterpiece: you know who painted it "within the first second of looking at it."

3. Galleries make the most money; status and museums are the access layer

  • Who wins economically? "The galleries." They take 50% on the primary sale, then steer resales back to themselves for another 15–25% — "on multiple round trips of a painting, they probably made more money on the painting than the initial cost of the painting." Cost of goods "basically zero," very large tickets, 50% rev share. Patrick's verdict: "Good business."
  • Auction houses look better than they are: 15–26% headline commissions, but estates (which must sell fast for taxes) trigger guarantee wars — Paul Allen's collection cleared well over $1B at auction — and competing guarantees can compress net margins to 2–3% or losses. Sotheby's at a ~$3B market cap after 100+ years: "good businesses, not phenomenal businesses."
  • Status isn't vanity, it's plumbing: "artists actually don't want their art in people's homes. They want it hung in the MoMA where millions will see it." Galleries favor museum-board members because those collections eventually land in institutions — "the boards of these museums don't look like boards of any other industry in the world because the boards unlock access." Naimi's own reputational lesson from Ovitz: refuse the consolation prize, or "you will always be the guy they give second and third tier work to." And the best entry point is between exhibitions, when an artist quietly gives the gallery one painting shared with "you and two or three other people" — not the fair previews sent to 5,000 collectors.

4. The founding thesis: multi-stage firms were the better seed investors

  • Naimi defined power law as a private value or exit north of $5 billion, then found that "if you eliminate Uber and Roblox, whose seed rounds were led by First Round Capital, it's close to impossible to identify power law companies in which the seed round was led by a seed-stage venture capital firm." The receipts: Sequoia led seeds for Stripe, Airbnb, Dropbox and Nubank; Andreessen the first institutional rounds of Okta, Databricks and Slack; Khosla seeded Instacart and DoorDash; Index seeded Robinhood and Figma; Lightspeed seeded Snap and (he thinks) AppDynamics.
  • The uncomfortable corollary: "seed funds that claim they had proprietary deal flow were mostly kidding themselves. They're a little delusional. It's hard to believe a seed firm with two or three people has more coverage at early stage than a multi-stage fund with 30 or 40." Head-to-head, multi-stages won on brand and on terms seed funds couldn't match — so he built Abstract "aligning my interest with multi-stage funds as opposed to aligning my interest with seed funds."
  • The pricing proof that the multi-stages, not the seed purists, "had a bit more of the right idea": between roughly 2008 and 2011 about 1,000 seed deals were announced. An equal check into every one captures Uber's 3,000x — a 3x net portfolio for blanketing the entire market, before adding Airbnb, Dropbox and Instagram. "There is no world in which you could blanket an asset class and generate a 3, 5, 7x." Conclusion: seed deals needed to be 3–5x more expensive as a floor — and even at a $25M average entry, blanketing should only break even. "Now we're in a market where you actually need to be better at picking than you were historically."

5. The tracker: 6–7,000 LinkedIn profiles and 47 checks in ten months

  • In 2016 he reverse-engineered the last few hundred tier-1-backed founders — "venture is a pattern matching business, for better or for worse" — into a profile (these schools, degrees, companies, roles, at these moments in the company's inflection), tracked roughly 6–7,000 matching people on LinkedIn, and got a push notification whenever one changed their title to founder. His discovery: "an unfunded seed-stage founder might be like the easiest person in the world to get a meeting with" — useful, since "I was a nobody at this point in Silicon Valley."
  • The output, August 2016 to June 2017: 47 deals — an angel check into Rippling, "a first dollar check into Solana at four cents a token," seeds in Clay, Cherry, Newfront, the management-company round of Polychain (briefly the world's largest crypto hedge fund), then Avalanche and dYdX. Scoreboard: two positions with $100B+ coin market caps (Ripple and Solana), Rippling approaching $20B, and eight or nine unicorns — with AngelList SPVs that "have returned close to $100 million."
  • AngelList was the entire cold-start solution: he sourced the deal, wrote the memo, and the platform sourced every dollar. His first syndicate — Ripple — had "$470,000 subscribed" when he refreshed four hours after posting: "Holy shit… I can't believe this actually works." Economics: 0-and-20 to LPs, AngelList takes 5 points of carry for sourcing capital, he keeps 15. For a six-month stretch he was one-third of all volume on AngelList.
  • How he got in: "Very aggressive… just being relentless," but deliberately likable and infinitely flexible on size — "I don't care if it's 25,000 or 500,000… I made myself flexible enough that it became hard to say no to me. If you give founders hard constraints on allocation or ownership targeting, you make it very easy for them to say no." Plus weekly catch-ups with every junior VC in the Valley: when multiple people named the same company in one week, he called it.

6. Flat broke at 24: the résumé before the firm

  • The pre-history is pure hustle: Iranian immigrant parents ("America revolves around money — I heard it a little too often as a kid"), $2,000 borrowed at 13 to trade — quickly derivatives, since $2,000 wasn't enough for stocks. At West Elm at 16 he gamed the non-clawback incentive structure by upselling staging ("have you ever seen a coffee table that's higher than a sectional?") and once single-handedly unloaded four UPS trucks of furniture, 7:30am to 7:30pm, when every other stock guy called in sick. His sweet-16 party business — he financed the venue and DJ, charged cover, hired "roided-out meatheads" for $50 a night — netted ~$2,000 a weekend, cash stuffed in a garbage bag when the pencil box overflowed.
  • Senior year of high school he made a few hundred thousand dollars trading out-of-the-money options on triple-levered bank ETFs through the financial crisis — "the good thing was it gave me a ton of confidence and I convinced myself I was a genius. The bad thing was it convinced me I was a genius." He skipped college, got a Series 65, and launched a hedge fund in January 2009 with ~$3M from 45 small checks. Months down 37% and 51% followed; August 2011 — Greece, 13 consecutive down days, and he was short vol (likely; garbled in source) — was "one of the worst months of my life." Everyone still made multiples, but he hated it: "the feedback loops in hedge funds are too tight — you can convince yourself you're a good or bad investor too quickly."
  • Then the wipeout: told by VCs (including GV's David Crane, after a cringeworthy suit-and-tie meeting) to start a company — "terrible advice to give anybody" — he self-funded a secondary exchange for marketplace-lending loans in mid-2014. Fourteen months later, product ready, the sector had collapsed: Sequoia was marking Prosper toward zero, LendingClub was down ~85% from its IPO peak. "I had spent my entire net worth building a supplemental product to a collapsed industry" — ending in Chapter 13 bankruptcy at 24, cleared within two years.
  • The reframe he now carries: Arjan Schütte (likely; "Aron Chute" in audio) of Core Innovation Capital gave him a job when "no one else in the world would have" — his answer to the kindest-thing question. And Jerry Yang, as an LP, refused his embarrassment: "wear that as an entrepreneurial badge of honor… Venture capital is you put everything somebody else has into whatever you believe in. And if it doesn't work out, you get a job at Apple or Google."

7. Selling a stake to the consortium — with a sunset — and rewriting portfolio construction

  • Cyan Banister (likely), then at Founders Fund, noticed him and introduced Kevin Hartz — Xoom founder (sold to PayPal for over $1B), Eventbrite co-founder, $3M-post Airbnb investor, first dollar into Pinterest. Hartz's line after their first meeting: "If you were this good at this, not knowing anybody, I wonder how much better you'll get if you know all the right people." Within roughly three weeks the chain ran Hartz → Chris Dixon and Keith Rabois → Marc Andreessen → Michael Ovitz → likely Bill Ackman, Kevin Warsh, and likely David Sacks.
  • That consortium bought an equity stake in his management company when he was 26, priced "just shy of 50" — but with a six-to-seven-year sunset: "everything I do in seven years, and one day they're not entitled to economics." Since venture's excitement "starts to happen in years 9 and 10," a seven-year timer "is nothing" — it lapsed a couple of years ago and "I'm proud to say I own 100% of my business again."
  • Fund one: $100M closed end of 2018, ~$50M anchored by the consortium, the rest from Josh Kushner, Matt Cohler, Neil Mehta, Leif Abraham (likely), Dan Rose, Chase Coleman, plus operators like Jerry Yang and Okta's Frederic Kerrest (likely) — and only four institutions (two college endowments, two fund-of-funds).
  • Those four grasped the heresy: institutions had been stuck on "VCs must own 15%" for 25 years while the funds grew 10–30x. Naimi's reframe — ownership as a relative metric: his consistent 5% from a $100M fund versus a co-lead's 15% from $1.5B is one-third the ownership from 1/15th the fund — "I actually had 5x the exposure… people ask me if I had an index approach. It's the opposite of that. I'm the most concentrated exposure you can get." By full deployment, in 94% of portfolio companies "there was not a venture fund anywhere in the world that would have gotten you more look-through ownership."

8. From the 5% tax to leading: the multi-stage floor is 10%

  • The original playbook ran 20-for-20: introduce his best companies to the relevant tier-1 partner — "You take your 15, I'll take my five" — every time getting his five, a tier-1 co-lead, and happy LPs. Then the irritation: "I felt like I was doing most of the leg work and getting this 5% tax."
  • The fix was leading while breeding the multi-stage in as co-lead, and stress-testing "how far can I push a multi-stage firm down on ownership before they walk but are still happy": the answer is 10% — "if we push them down to six or seven, it's just not worth it. They'd rather wait for the Series A." Validation came fast: of his first four led deals, two raised follow-ons from Benchmark, one from Sequoia, one from Andreessen — proof his leads weren't adverse selection.
  • Today Abstract leads 80–90% of its portfolio, its led deals "have dramatically outperformed" its co-invests, and by his data it has "the highest likelihood of getting a follow-on Series A by a tier-1 VC firm… by a pretty wide margin" — at a pace of ~14 net new seed deals a year, "a little over one deal per month."
  • The machine is built for speed and coverage: 3–5 meetings plus back-channels, compressing "what might take another firm two to three weeks into two to three days"; 18–30 pitches a week ("it's not a flex to get a meeting with me — I pretty much don't say no to meetings"); a daily 30-minute all-hands on every company met. His creed, via Doug Leone through Roelof Botha: "Dumbo ears — you have to hear everything or see everything." And a direct pushback on the prior day's guest: coverage may not matter at growth, but "at seed stage, coverage is absolutely key… most of these companies don't even have websites yet."

9. Picking: three salesmanships, dilution sensitivity, and the non-local pivot

  • "Investing in founders works a lot better for me than investing in markets." The genetic makeup: commercial plus technical, where commercial means salesmanship in three verticals — fundraising; hiring ("hiring in early-stage startup companies is sales" — convincing a $400k Meta-caliber engineer that a $150k salary plus equity in "a concept of an idea" is rational); and selling V1s that are "half-ass broken glitchy things that no one would pay for." Technical bar: an engineer other engineers would actually work for, with shipping velocity — "six weeks or six months?"
  • His favorite screen: "prove to me that you're exceptional" — because of the old Quora question about founders over 35, answered by Reed Hoffman, Marc Benioff and Reed Hastings, all already successful when they started. "It's hard for me to believe that the first impressive thing they're ever going to do is this company they're asking me to invest in."
  • The counterintuitive preference: dilution-sensitive founders — not the "standard" seed seller of 20–25%, but the one who says "I need $3 million and I want to sell as little of my company as humanly possible." Those founders hold the same bar on every point of equity, fire misses before the 12-month cliff, and build teams whose smallness shocks people relative to what they've achieved — "incredibly high-quality talent has a multiplier effect on company efficiency."
  • On resilience: "the local pivot is what kills companies." Poparazzi (seeded as TTYL, five or six pivots earlier) hit #1 on the App Store on launch day, took a Benchmark term sheet — then, six weeks in, no retention, and the founder returned the cash rather than grind out another consumer-social idea. Vapi (originally Superpowered) went zero to double-digit millions of ARR within 14 months of launch — four years and seven pivots after Naimi seeded it. Krea (likely; originally Genverse) is the same story.

10. Winning: run the whole fundraise as the sole node — that's the product

  • The broken thing he chose to fix: the founder's Google-doc fundraise, where nine investors intro 30 VCs — too many misaligned incentives, too many leaks ("VCs are just trying to gather information"). His alternative: "I will be the sole node. I'll help with the deck, the data room, mock pitches; I'll make introductions to the relevant top GP at every firm; we'll line up all meetings over a 3-day window; at the end of every day I'll get feedback on what's resonating." Choking off information forces VCs to "truly build conviction" — and they move faster.
  • Leverage is the deliverable: more term sheets, less dilution. His data: highest seed-to-A graduation rate, highest-decile Series A valuations, lowest average dilution. One founder's reference call: the odds you own 10% more at exit are "10x higher with Abstract on your cap table" — 5% saved at the A, 3% at the B, 2% at the C, worth an extra $200M on a $2B exit. "I can't personally think of a single value-add that translates to more than an extra $200 million in your pocket." The ultimate validation: tier-1 co-leads now tell founders "we're more than happy to let Ramtin run this process — they'll do a better job than anybody." Patrick's tag: "you're sort of the czar now for this process."
  • Who wins the competitive A? "Sequoia, Benchmark and Andreessen… when one of those three extends an offer, they tend to win unless competing with one of the other two." A LinkedIn stat he cites: the firms leading the highest number of financings in companies before they became unicorns since 2015 — Andreessen first, Sequoia second, Benchmark fifth, "shocking when you consider how much smaller their funds are." The moat is board-member density: founders are told to optimize for "the best board director for the next 10 years," and those three have the storied ones.
  • The missing piece at Abstract is brand — and the gap between personal and firm brand: as one VC told him, "I hear the name Ramtin multiple times a week; I hear the name Abstract once a month." Very few firms have more than one to three partners who can independently source, compete and close — "which is why venture is hard to scale as an asset class," and why LPs wish they could back just the four GPs, not sixteen. The criticism he accepts historically: "heat seekers, signal chasers… which wouldn't have been inaccurate six or seven years ago — but over time, I think we became the signal. People tend to hold on to old narratives."

11. The health check: AI multiples undetermined, seed-to-A drunk on IRR, private-market liquidity as throttle

  • On AI valuations he refuses the easy call: "I actually don't know if it's true [that they're too high], and I don't think anybody will know for another three or four years." A company growing 20x, then 15x, then maybe 10x year-over-year has no established fair multiple — but there's also "no shortage of application-layer companies that become obsolete overnight when it becomes a feature of a foundation model company." Verdict: "undetermined" — and since venture is about capturing outliers, "you'll do whatever it takes to get into one of those companies."
  • The part he calls unhealthy, "very reminiscent of 2021": in the last six months, seven of his seed companies raised Series As within weeks at 4–5x his entry — "basically just paying 10 times the price for the same exact company I invested in a couple months ago, plus or minus a few hires." His latest funds are exiting the J-curve "way too quickly" at 30–40% IRR within months of deployment: "there should be negative IRR during the deployment period… the industry is getting a little drunk on IRR."
  • The staying-private flywheel: mega-funds can only scale because company scale scaled — now a dozen to 15 private companies can absorb $500M–$1B checks while still out-growing their public comps. The unintended benefit is enforced hunger: "early liquidity was the bug and not the feature of crypto — people got rich too quickly and they stopped building things." Tender offers of 1–5% buy "a down payment on a house, not $40 million and generational wealth." The Google cautionary stat as he tells it: over 100 people made millions, "and 92 of them were never heard of again — and the other eight became VCs." Good for company building; "problematic from a venture returns perspective" since no LP wants liquidity in 3–5% installments — hence the new wave of continuation vehicles.
  • On LPs, his taxonomy: "the ones with imagination and the ones without." The imaginative ones — fund-one backers of non-obvious managers — "have done dramatically better" than those who only back spinouts with underwritable track records (which likely overstate future access anyway). His exemplar: Paula Volent (likely) — Bowdoin's endowment chief, now Rockefeller, day-one LP to Chase Coleman, early to Josh Kushner, with Druckenmiller chairing the IC — was Abstract's first institutional LP, and her kind of add "was a signal to the market: pay attention to this fund."
Ramtin Naimi

I don't think there's any excuse for saying that you can't start a venture capital firm with no money, because I was literally flat broke when I started Abstract.

Patrick O'Shaughnessy

Did you file for bankruptcy?

Ramtin Naimi

I had literally filed for bankruptcy at 24 years old when my previous startup company had failed. I was literally out of bankruptcy when I started a venture capital firm.

1. The Art of Collecting

Patrick O'Shaughnessy

All right. I think the place we have to begin is in the art world. I think you have the most systematic, intense art-collector story that I've heard, and I want to start here not because it's some esoteric side topic, but because I think there will be lots of inspiring points for what we'll talk about in investing as well—not art, but companies.

Can you lay out your art-collecting journey for us? Where did it start, why did you get interested in it, and how did you begin to learn about how the art world actually works? That's my one big question: Explain how this works to us.

Ramtin Naimi

I have 2 incredibly close mentors. One who introduced the 2 of us, Michael Ovitz, and then another guy named Stuart Peterson. Both of them have world-class art collections. Michael has a storied art collection. I'm sure you've seen it.

Patrick O'Shaughnessy

Yeah.

Ramtin Naimi

I spent a lot of time at their houses over the years, and every time I went, I tried to learn a little bit more about what was in their house. They could both spend 2 or 3 hours walking you around their home and talking about what they have, how they got it, and the story behind it—the history behind it and the significance of it.

I always thought that was really interesting. I never really had much time for hobbies, and it was one that I thought my wife and I could enjoy together. I needed to find a hobby, and I thought golf was a little one-sided. So, for me, art collecting seemed like it could be golf for both me and my wife.

Then I started dabbling in understanding the markets, and I realized that nothing in Michael's collection was attainable. So I scratched most of those artists off my list. Then I looked at Stuart's collection, and most of it was unattainable. Some of it was by artists who were still somewhat attainable.

I worked with an adviser briefly, just so I could familiarize myself with the market. Once I spent enough time familiarizing myself with the market, I realized that, like anything, if you're going to invest time and resources into something, you're better off doing the majority of the work yourself.

Obviously, it's good to have people like advisers who are experts and boots on the ground in the ecosystem advising you here and there. But I think you need to maintain the relationships with the galleries yourself. You need to maintain the relationships with the auction houses yourself, and even have some direct artist relationships yourself.

So I spent time, energy, and resources dedicated to learning as much about it as I possibly could. I wanted to collect primarily contemporary artists and primarily living artists. I decided to collect 3 different buckets of artists, and I break them down by generation.

I have artists who are 2 generations before me. These guys are in their mid-to-late 60s and early 70s. Then I have artists who are maybe 1 generation before me. These guys are in their late 40s to late 50s. Then I have artists of my generation, and that's everyone who's 28 to 38 years old.

I started to understand who is important in the conversation at a given time and who is getting museum and institutional interest. Who are museums paying attention to? Who are museums hosting exhibitions for? What makes this artist unique? Where does this artist draw inspiration from?

There's also a lot of artists who are great and have all those boxes checked, but might not necessarily be something that I want to live with. My wife and I personally like living with our art. Even if something could be a great asset to hold, if we don't want to hang it up on our walls, we don't feel right about the concept of buying art for the purpose of putting it in storage.

The artists 2 generations before me tend to be more heavily dominated by white male artists—guys like Richard Prince, Christopher Wool, and George Condo. A generation before me includes guys like Mark Grotjahn and a lot of female artists like Jenny Saville, Laura Owens, Cecily Brown, and Jacqueline Humphries.

In my generation, it's more along the lines of Rashid Johnson, Christina Quarles, Avery Singer, Marina Rheingantz, and Anna Weyant. All of these artists now tend to be represented by the blue-chip galleries.

2. Parallels Between Art and Venture Capital

When I started dabbling in the art world, I realized that there are actually an overwhelming number of parallels between the venture world and the art world, primarily in the way blue-chip galleries work and the way that the big platform venture capital firms work.

If, at any given time, there are 50 important practicing artists in the world—or even the estates of the most iconic dead artists—they tend to be represented by the big 4 galleries: Hauser & Wirth, Gagosian, David Zwirner, and Pace. Once they're represented by those galleries, they're deemed blue-chip artists, and their prices are very, very high.

But their prices tend to sustain or even appreciate because those galleries are very large, they have very big clients, and they represent a lot of institutions. So they can control the markets for those artists. People tend to be more comfortable paying a premium to buy art from those galleries because of the inherent safety net you get when buying from them.

But then I started to realize that there are smaller galleries, and even smaller galleries beyond that, that tend to share a lot of artists with the larger galleries. It's because they were the ones who initially discovered them.

It's the same thing in the venture capital world. You have the 4, 5, or 6 top venture capital firms in the world that tend to have exposure to every power-law company and every generational company in any given vintage. More often than not, you'll see the same firms that financed those companies earlier and earlier and earlier.

Like the big venture capital firms try to maintain relationships with the firms that spot talent earlier and earlier, the big galleries tend to maintain relationships with a few of the mid-tier or smaller-tier galleries early. What I started to do after that was spend time with those galleries that I noticed were the early spotters of talent and find these artists early in their careers who had a high, so to speak, graduation rate to getting picked up by the blue-chip mega-galleries.

As soon as that happened, their prices basically quadrupled. I'm not saying that's the purpose behind doing this, but obviously it's nicer to pay 25% of the cost of something versus full value. So I started maintaining those relationships and trying to see what I actually liked from their programs, because, like anything, not 100% of the artists graduate.

3. Challenges and Strategies in Art Collecting

From there, you have to start applying some of your own judgment and hope that you have the right taste to identify what other people are going to find appealing and what institutions are going to find appealing.

Patrick O'Shaughnessy

What made a collection like Ovitz's unattainable? That's an interesting word. Why could you not replicate it? Behind that question, I guess, is: What do the collections that you respect the most have in common, from your perspective?

Ramtin Naimi

The reason Ovitz's collection is not attainable is due to the sheer value of it. There's this one art list—I'm blanking on the name—that ranks collections based on the means by which they were obtained.

That's actually really interesting, because people today say that Steve Cohen and Ken Griffin have the world's greatest collections, and they probably do. But they don't assign the same score to them because—

Patrick O'Shaughnessy

It's like a low-IRR collection.

Ramtin Naimi

Exactly. So if you can afford to buy any piece of art in the world, it's easy to know what the 50 most iconic things in the world are, and you just have to buy them. Everything's for sale in the art world, so as long as you're willing to pay the price, you can build that collection.

The collection that scored the highest—and I'm going to say that I don't remember their name, but it's easy to look at the article—was assembled by a husband and wife who were both government employees. The husband was a postman and the wife was a librarian, and they spent their weekends collecting art in the '60s.

They were collecting Pollocks and Rothkos, and they ended up giving it all away to museums. They never actually did it for any monetary gain, but their collection ranked so highly because they were able to judge purely based on talent and skill, before anybody had any idea who these artists were and before there was any value assigned to their work.

I do believe that in every great generation, in every decade-long period, there are certain bodies of work that are considered iconic. If you think of the '80s, you have Richard Prince's “Cowboys,” which Michael probably has one of the greatest examples of. He still has a couple of great ones.

They were basically old Marlboro bro ads that Richard Prince had ripped out of magazines, turned into photography, and sold. But they became iconic because he sort of owned the concept of appropriation as an artist.

And then, in the early 2000s and late ’90s, Richard Prince came out with those nurses, where he was printing out old nurse book covers and then painting over them. That became another iconic example of appropriation. Then you had Tracey Emin. She was a lot more graphic than most female artists were in the ’90s about the female body as a subject.

When you’re trying to identify those things in real time, it’s very difficult because there are a lot of art shows and exhibitions at any time in New York City. New York is the king of exhibitions, and there are exhibitions that are positively acclaimed, but 2 or 3 years later, that artist fizzles out. When you’re collecting artists who are practicing and active, it’s very challenging because there are 1,000 artists in any generation, and only 10 of them end up mattering 20 or 30 years later.

I collect active artists, and then I try to go back and look at some historical things. For whatever reason in the art world—and if you look at all the data in the art world, it tends to work like this—this cycle continuously happens where things that were iconic 20 years ago tend to be undervalued 20 years later, then get highly valued 30 to 40 years later. I tend to find things that were the indisputably iconic bodies of work from the ’90s and 2000s that today might be out of favor.

A lot of the people who were very iconic in the ’90s and 2000s happen to be white male artists who are currently out of favor in the art world. There’s not a lot of demand for their work, but it’s a really good buying opportunity for those artists, at least in my opinion.

The next thing you look for is depth in that artist’s collector base. There are certain artists who have huge followings. They put out 50 paintings through their multiple galleries per year, and they’re all sold. They have 50 paintings that show up at auction, and they all sell and clear large price tags because their art appeals to a large demographic of collectors. George Condo and Rashid Johnson are probably the 2 artists who fit most squarely in that bucket today.

Then there are artists who are a little bit more niche, who have collectors and whose markets are very strong, but their markets can’t sustain 50 or 100 paintings transacting every year. Their markets can sustain 8 to 12 very high-value paintings transacting every year. You always try to think about that in your calculus because you’re asking yourself, “Well, if the market depth is shallow and I’m a young collector, and everybody else collecting this artist is 30 to 40 years older than me, in 20 to 30 years, am I going to be the only person who’s collecting this artist?”

There are a lot of things to try to think about there, but I think at the end of the day, you’re really just trying to buy art that stands the test of time.

Patrick O'Shaughnessy

When we talk about abstract art, I’m going to ask about the time that you spent studying power-law outcomes in companies. One of the lessons I’ve learned from doing this show for so many years is that the power-law concept applies literally everywhere. It sounds like not only does it apply in art, but actually within a given artist’s collection of work. The idea of a masterpiece or high quality is really interesting to me. What can you say about those 2 concepts and what you’ve learned about them?

Ramtin Naimi

It’s so strange because there are no earnings against which to measure success. There’s nothing really quantitative. It’s in the eye of the collective beholder. But what I try to define is what’s shared in common among high-quality or masterpiece works.

I think in the art world, they’re very definitive examples of what that artist is known for—something that you could look at and basically say, “This is exactly what the artist was trying to get across in their message, and it came through very clearly in this painting or this sculpture.” Oftentimes, you’ll see a painting by an artist and you’ll have to do a double take to realize which artist actually painted it. There are certain paintings that you look at by an artist, and it’s so obvious that it was painted by that artist.

Within the first second of looking at it, you know who painted it. So that's obviously a really good indication. A lot of it is just frame of reference. You don't actually appreciate what is a great example until you've seen tons of examples, right?

It's a phrase that Michael Ovitz always talks about: frame of reference. I'm sure you've heard me mention him before. It's the same thing with the more companies you meet: the easier it gets to discern what the better companies are. The more art you look at, and the more art you look at by a specific artist, the easier it becomes to identify what a great example of that artist is.

4. The Role of Status and Reputation in Art

Certain things you look at and you're like, "Well, this looks like one of their paintings, but it looks like a messy version of one of their paintings." Or, "This looks like a painting that they started working on, and they realized it wasn't going in the right direction, so they half-assed the rest of it." Versus, "This is something they nailed, and they know they nailed it." A lot of that just has to do with training your own eye and looking at a lot.

Patrick O'Shaughnessy

Talk about the role of status in the art world, both for collectors, for galleries, and for artists.

Ramtin Naimi

That's a real thing. I don't actually get involved in any of that because I don't have time for it. I don't think I've ever gone to an actual exhibition opening. It's part of the upside and downside of being in San Francisco: there's no art in San Francisco.

I don't think I've ever bought anything that I saw in person before buying it. I've only ever bought previews. You have to find time to actually fly somewhere and go see something in person, and I don't have the time. My schedule, unfortunately, doesn't lend me the leisure to do that.

I think it's very common in the New York world, especially among finance guys who are active art collectors. I think it creates competitive dynamics: "Oh, you have one of these? I actually have the better one. Oh, we're both fighting over the same painting. I'm the one who got it."

I think that's where the galleries leverage those competitive dynamics to do what's ultimately best for the artist, right? At the end of the day, artists actually don't want their art in people's homes. They want their art in museums. They don't want their art to go in someone's living room, where only 20 people will ever see it. They want it to be hung up in MoMA, where millions of people will see it over time.

That's why you see a lot of these guys on the boards of those museums, because those museums ultimately want to foster relationships with the people who have the greatest collections. A large portion of those collections one day ends up in their museum. That's why museum affiliation is also a really great way to access great art.

Galleries are more inclined to give great paintings to people who are on the boards of MoMA, the Met, the Whitney, and the Guggenheim because they know that, more likely than not, this painting—maybe not tomorrow, but eventually—will end up in the collection of this museum. So that is definitely where status comes into play. That's why, when you see the boards of these museums, they don't look like the boards of any other industry in the world, because the boards unlock access to what these guys consider to be the greatest art.

5. The Business of Art Galleries & Auction Houses

Patrick O'Shaughnessy

What is surprising about how the Big 4 houses work that you've learned?

Ramtin Naimi

The funny thing is that they compete for the artists very similarly to the way VCs compete for deals, right? It's very obvious who the artists are who are in the most commercial demand, who are in the most institutional demand, and who they could see building their careers over the next 10 or 20 years.

The courting process is the same, right? It's like, "We'll do a better commission split with you. It's not 50/50 with us; we'll go 60/40. We'll go 70/30. Do you want a signing bonus? Here's $1 million cash up front. Go with us. Don't go with them."

It's very competitive among them to get the best artists, and artists are always leaving one and going to the other. I still don't quite understand, because generally speaking, in the talent world, contracts are pretty ironclad. You can't just go from one person to the next. But there is—I still don't quite understand how that works. I'm still curious to learn that aspect, but artists do frequently go from one gallery to another.

Patrick O'Shaughnessy

What are the keys to being known or building a reputation as a great collector?

Ramtin Naimi

There are things that Michael Ovitz has taught me over the years, right? In the early parts of my collecting, there was a painting that I wanted, and they didn't offer me that one. They offered me the consolation prize instead. I was talking to Howard Marks or Stu. I'm like, "What do you think? Should I take it?" And they said, "No, because if you do—"

Patrick O'Shaughnessy

You're a patsy.

Ramtin Naimi

Exactly. Right. They're going to know that they can just keep giving you consolation prizes, right? Ultimately, they want you as a collector. So if they realize you're only going to buy what you want to buy, they'll ultimately give you what you want.

If you play along and play ball, if you're the guy they can give second-tier and third-tier work to, you will always be the guy they give second- and third-tier work to. So there's that aspect of it.

A lot of it is just staying top of mind. What's worked best for me in venture also, right? I see early-stage seed companies at a high level of frequency because I stay top of mind for my founders who have friends who might be starting companies. I stay top of mind for angel investors who are actively grooming the next generation of founders and are looking for people to introduce them to lead their seed rounds.

In the art world, it's the same thing. It's sending your dealer a gift when their baby's born, sending them Christmas gifts, and checking in with them from time to time. The reason I mention staying top of mind is that the most competitive time to get a painting is during an artist's primary exhibition or during a fair like Art Basel, because they send that preview out to their entire collector base.

5,000 people are going to see that painting, and you're definitely not the only person who wants that individual painting. Your odds of getting it are close to nothing unless you're willing to jump through a million hoops to get there. But every single artist is working; they need to make money.

More often than not, in between exhibitions and in between fairs, they might make 1 painting and give it to the gallery and say, "Please sell this for me." That's where I found most of my work. The artist just made this 1 painting available: "We're offering it to you and 3 other people. Please let us know what you think." Your odds are much higher when it's just shared with you and 2 or 3 other people.

Patrick O'Shaughnessy

If you think about the artists, the galleries—both kinds of galleries—the collector who buys and then maybe sells in the future, and other players, auction houses, et cetera, who makes the most money?

Ramtin Naimi

I would say the galleries. I think the big galleries do quite well, because the big galleries that have great clients and are able to control their markets tend not only to manage all the primary sales, but they also tend to manage the majority of the secondary sales.

If you're buying great work from Hauser, Gagosian, Zwirner, or Pace and you want to sell a painting, they don't want that painting to go to auction. They want that painting to go back to them because they probably have 20 other people who might be interested in that painting. Not only did they get their 50% commission when they sold the painting to you in the first place, but now they're going to get somewhere between 15% and 25% for selling it for you.

Over multiple round trips of a painting, they probably made more money on the painting than the initial cost of the painting. I would say they make the most.

Auction houses, you would think, make a lot of money. They have no costs except for marketing and displaying the art, and then they take anywhere between 15% and 26% commission, depending on the value of the art. Then I started realizing that's actually not the case, right?

They have competitive dynamics, too. The most famous example was Paul Allen. When he passed away a few years ago, his entire collection became available for sale, and I think it was at an auction house. The collection sold for well over $1 billion in cumulative sales.

When someone like him dies—he's an extreme example, but there are plenty of people who have collections worth $50 million, $100 million, or $300 million—it's usually the estates of those people that auctions want. It's part of the reason that the estates actually have to go to the auctions, because obviously they have a finite amount of time before they have to pay the taxes. The quickest way to sell everything is to send it to auction.

That's when the auction houses start competing with each other over commission splits and guarantees. It's more along the lines of, "Hey, we will guarantee you at least $500 million for this collection. We'll guarantee you at least $100 million for this collection. We will reduce our commission from 26% to 13% because we're going to give half the commission back to you."

There is no shortage of stories where their guarantee was too high to compete with the other auction house, and they ended up losing money, or their net margin ended up being 2% or 3%.

I don't think the auction houses have huge market caps. I think Sotheby's is about a $3 billion market cap, and it's a well-over-100-year-old company. So I think they're good businesses, not phenomenal businesses, because I think their margins are a lot more volatile than one would think looking into it externally.

I'd say the blue-chip galleries seem to have endless pockets. What they spend money on is beautiful gallery space and making beautiful exhibitions, but they have a cost of goods that is basically zero, then very, very large tickets and a 50% revenue share.

Patrick O'Shaughnessy

Good business. Where are venture and art the most divergent in how the 2 worlds work?

Ramtin Naimi

It's a lot easier to identify what is going to be a great company than who is going to be an artist that stands the test of time. There are a lot more tangible things you can look at. There are much more fundamental and technical things you can look at that'll tell you that something is special and something is good.

There is a market for pricing in the venture world that might not necessarily be the case in the art world. Fair market value is very clearly determined in the venture world: a company goes out to fundraise, an auction is run, term sheets are offered, and a price is set.

Those things are obviously very different. I'd say the primary difference is really just that venture is much more tangible—even though art's tangible, you kind of get my point—in that there's a lot more to underwrite.

Patrick O'Shaughnessy

Yeah. There's an E, not just a P.

Ramtin Naimi

Exactly.

6. Building a Successful Venture Capital Firm

Patrick O'Shaughnessy

Okay. I want to talk about the way that you've learned how the entire early-stage venture world works. Abstract has very quickly become one of the firms whose name you hear a lot. You hear your name a lot.

I'd love you to explain, in the same way you explain the art-world market structure—I'll call it market structure—your perspective on the early-stage investing market structure. How does it work, and how did it get there?

Ramtin Naimi

Sure. The simplest way to describe this is how I came up with a thesis for how Abstract actually invests. This thesis has evolved over time, but the thesis on which I started Abstract was trying to identify which companies had the highest likelihood of becoming power-law companies.

I identified power law as any company that had a private market cap or exited north of a $5 billion valuation. What I'd realized over time was that if you eliminate Uber and Roblox from the equation, whose seed rounds were led by First Round Capital, it's close to impossible to identify power-law companies in which the seed round was led by a seed-stage venture capital firm.

This has changed in recent years, which is why our strategy has also evolved. The thesis it was built off of has stayed constant: that multistage, tier-one VC firms were better at seed investing than seed funds are.

It's not to say that they'll outperform them, because I don't think the portfolio-construction model allows for that anymore at the scale of those funds. But I do believe that the power-law companies of the future will be more likely to have seed financings led by multistage venture capital firms and seed-stage venture capital firms.

In the early days, people didn't think multistage firms did much seed investing. But if you look at Sequoia, they led the seed round for Stripe, Airbnb, Dropbox, and Nubank. Andreessen Horowitz led the first institutional rounds for Okta, Databricks, and Slack. Khosla led the seed round for Instacart and DoorDash. Index led the seed round for Robinhood and Figma. Lightspeed led the seed round for Snap and, I think, AppDynamics. The list goes on and on.

What became obvious to me was that seed funds that claimed they had proprietary deal flow were mostly kidding themselves. They were a little delusional. It's hard to believe that a seed firm with 2 or 3 people has more coverage at the early stage than a multistage fund with 30 or 40 people.

Then it became very apparent to me that when a multistage fund and a seed fund tried to compete with one another, it was very hard for a seed-stage venture capital firm to compete with a multistage venture capital firm. Oftentimes, multistage venture capital firms had brand weight that the seed funds couldn't compete with, but more often than not, it was the fact that they were willing to offer a valuation and terms that a seed fund couldn't compete with.

I decided to build a seed-stage venture capital business, initially aligning my interests with multistage funds as opposed to aligning my interests with seed funds. The reason I thought people were wrong when they said multistage funds were jacking up the prices of all these deals is that we pulled the data on this.

If you look between 2008 and 2011, there were about 1,000 seed deals funded in that time frame, or at least publicly announced seed deals in that time frame. So there's some survivorship bias there. But what you need to ultimately look at is that probably 80% of the companies got announced, because that's just what ends up happening in venture.

Let's assume there were 1,000 companies and Uber was in that bucket. If you wrote an equal-sized check into every single one of those 1,000 companies, you would have gotten a 3,000x just on Uber. So you would have actually had a 3x net venture-capital portfolio blanketing the entire market.

There was also Airbnb and Dropbox and so many other companies, including Instagram, that were funded in that window. There is no world in which you could blanket an asset class and should be able to generate a 3x, 5x, or 7x.

That was a very clear sign that deals were too cheap back then. As with anything, as markets get more efficient over time, deals start to price a little bit more accurately. I thought that seed funds were holding on to those low prices a little too drastically, and multistage funds had more of the right idea.

If you start to think that a 3,000x multiple on a seed deal like Uber gave you a 3x across blanket coverage between 2008 and 2011, then you could argue seed deals need to be 3x more expensive as a floor. But if you mix in all the other companies, you'd probably assume that seed deals should be 5x more expensive as a floor.

By the way, even if that's the case, at an average entry valuation of $25 million, if you blanket the entire market, you should be able to break even on your money—which should never be the case because, as you know, investing is challenging. So now we're in a market where you actually need to be better at picking than you were historically.

In the early days, I looked at the last few hundred companies that were backed by the multistage, tier-one venture-capital firms, and I started to identify patterns that existed in the founders they were backing. Venture is a pattern-matching business, for better or for worse.

What I started to notice was that they liked founders who went to one of these schools, got one of these degrees, worked at one of these companies, in one of these roles, and during one of these periods of time in that company's inflection. So I started tracking individuals who fit the bill on LinkedIn.

There were probably 6,000 or 7,000 people who qualified, and any time one of them changed their job title to “founder,” I got a push notification and started reaching out to them.

Patrick O'Shaughnessy

What year is this, just to ground us?

Ramtin Naimi

2016.

That's kind of when I realized that an unfunded seed-stage founder might be the easiest person in the world to get a meeting with. I was a nobody at this point in Silicon Valley, and the fact that anybody would take a meeting with me was nice.

As their financing rounds came together, I would ask for any allocation. They would give me anything from a $25,000 check that I'd raise as an angel up to a $500,000 check that I'd raise as an SPV. I'd use AngelList for that.

I'm probably the number-one AngelList success story. AngelList really catapulted my career, and I think it's actually an amazing business that more people should pay attention to and leverage the same way I leveraged it.

Patrick O'Shaughnessy

You did 47 in that first year?

Ramtin Naimi

Forty-seven in that first 10 months. I funded 47 deals in a 10-month window between August 2016 and June 2017.

I got an angel check into Rippling. I got a first-dollar check into Solana at $0.04 a token. I got a seed check into Clay, a seed check into Cherry, and a seed check into Newfront. I got into a bunch of crypto companies.

I got into the management-company round of a hedge fund called Polychain Capital, which for a brief period of time was the largest cryptocurrency hedge fund in the world, and even private deals as well. Then I got to seed a bunch of the companies that spun out in the early crypto ecosystem, including Avalanche and dYdX.

I think our SPVs have returned close to $100 million on AngelList at this point. Within the first 47 companies that I had funded, 2 of them—Ripple and Solana—have market caps north of $100 billion today.

Rippling is approaching a $20 billion market cap. Everything else I mentioned has a market cap between $2 billion and $7 billion. So, out of 47 companies: 2 centacorns, 1 decacorn, and about 8 or 9 unicorns.

These individual types of founders that I was tracking turned out to be the right types of individuals to track.

Patrick O'Shaughnessy

Is that how you found all those people?

Ramtin Naimi

For the most part.

Patrick O'Shaughnessy

Wow.

Ramtin Naimi

Some of them were obviously people I found by spending time with every junior VC at every single venture capital firm in Silicon Valley. I would have catch-up meetings with all of them on a weekly basis, and when I heard multiple people in one week mention the same names over and over again, I started reaching out to those individuals. I got into a bunch of deals, and the—

Patrick O'Shaughnessy

How did you do that? How did you get into them? You must have had to be quite aggressive.

Ramtin Naimi

Very aggressive.

Patrick O'Shaughnessy

What does aggressive mean for you?

Ramtin Naimi

For me, it just meant being relentless. Just checking in constantly: What can I do? How can I be helpful? I really did focus on just being likable, though. I wanted to be somebody the founders thought, “He’s a good guy, he’s working hard. Let’s get him on our cap table.”

I wasn’t aggressive about my check size. I was like, “I don’t care if it’s $25,000 or $500,000. Anywhere in that range, I’m happy with.” I made myself flexible enough that it became hard to say no to me. If you give founders hard constraints on an allocation you need or ownership targeting, you make it very easy for them to say no to you because they’re like, “Sorry, I can’t make that work.” But if you’re flexible, people generally, if they like you, want to work with you.

After I financed those companies, three different co-investors we had were Founders Fund, Andreessen, and Khosla. I didn’t have a relationship with any of those venture capital firms. The individuals I was tracking turned out to be the right individuals, and the firms that I wanted to co-invest alongside ended up being the firms I ended up co-investing alongside, just by the nature of finding these individual founders to back.

That’s when my journey really picked up. Cyan Banister, who was a partner at Founders Fund at the time but had spent a lot of time at AngelList, had noticed me. She and I spent some time together, and she introduced me to her close friend Kevin Hartz.

Kevin Hartz, at the time, was a partner at Founders Fund. Kevin Hartz is a legend in Silicon Valley. I’m not sure if you know him, but—

Patrick O'Shaughnessy

I don’t know him, but I know the story.

Ramtin Naimi

He founded Xoom in the early 2000s—

Patrick O'Shaughnessy

And Eventbrite too, right?

Ramtin Naimi

And Eventbrite as well. He took Xoom public and then ultimately sold it to PayPal for over $1 billion. But he’s also been a phenomenal investor. He was in the $3 million post-money valuation round of Airbnb. He was the first dollar into Pinterest. He was early in Uber. He was early in PayPal.

All roads from my network ultimately actually lead back to Kevin Hartz. Kevin and I met, and I hit it off with him maybe in his first year of tenure as a partner at Founders Fund. He started writing checks into a few managers. He wanted to find a way to work with me, but then also just opened up his network to me.

7. Insights on LPs and Venture Capital Trends

This is part of the most special thing about Silicon Valley: There are certain people in Silicon Valley who just want to help other people succeed. I’ve been fortunate to be blessed by having relationships with a lot of those people. Kevin met me, and I think when he ended the meeting, he basically said, “If you were this good at this, not knowing anybody, I wonder how much better you’ll get if you know all the right people.”

Kevin introduced me to Chris Dixon at Andreessen Horowitz, and Keith Rabois. Chris Dixon introduced me to Marc Andreessen. I think it was Marc Andreessen who introduced me to Michael Ovitz. Michael Ovitz introduced me to Bill Ackman, Kevin Warsh, and David Sacks.

Ultimately, a consortium came together with all those individuals, and they bought an equity stake in my management company when I was 26 years old. That deal had a timer on it because I didn’t want to be owned by anybody in perpetuity, and that lapsed a couple of years ago. I’m proud to say I own 100% of my business again.

It was a surreal experience. I went from having no network—these were only individuals I’d read about—to having met all of those people in a matter of about 3 weeks and finding a way to structure a deal with all of them. Kevin and Michael were probably the 2 most instrumental people in that and have stayed my 2 closest mentors to date.

I kept doing the SPVs and kept writing the angel checks for an additional year, until I realized that I could actually institutionalize this approach. I set out to raise Seed Fund I. That was a $100 million fund that I raised at the end of 2018. Those guys had anchored the fund with about $50 million, and the remaining chunk of the fund came from a lot of people who looked like them: Josh Kushner, Matt Cohler, Neil Mehta, Leif Abraham, Dan Rose, Thomas Lehrman, Chase Coleman, and Santo Politi.

Then I got a bunch of operators, including Jerry Yang, who founded Yahoo, and Frederic Kerrest, who founded Okta. I ended up getting 4 institutional LPs in Fund I. Those 4 institutions were 2 college endowments and 2 funds of funds.

I basically rewrote the book on portfolio construction with my first fund. Part of this stems back to what my initial part of the strategy was. Institutions had this framework that venture capital firms needed to own 15% of a company in order for the math of a deal to work out, which never made that much sense to me because they’d been stuck on that 15% framework for the last 25 years.

The difference is that in that 25-year window, these funds have grown 10, 20, or 30 times, but that 15% threshold—or the 15% to 20% ownership they wanted these firms to have—still stayed constant. What I focused on was ownership as a relative metric as opposed to an absolute metric.

What I mean by that is, I knew I could get 5% ownership in these deals very consistently, and I knew the firms I was co-investing alongside could get 15% ownership in these deals very consistently. Back then, these firms were much smaller than they are today.

Let’s assume the typical multistage fund I was co-investing alongside in 2016 was $1.5 billion, and my fund was $100 million. If I could get 5% and they were getting 15%, sure, I had one-third of their ownership out of a fund that was one-fifteenth the size. So I actually had 5 times the exposure.

This is frustrating to explain to people because people ask me if I had an index approach. I’m like, “It’s the opposite of that. I’m the most concentrated exposure you can get to these companies.” There were only 4 institutions that truly grasped that.

By the time we fully deployed Fund I, it became pretty obvious that in 94% of the companies we’d invested in, there was not a venture fund you could have invested in anywhere in the world that would have gotten you more look-through ownership in that company than you would have gotten through Abstract. Our next fund was highly institutional. Now we’re very institutional today, and everything is oversubscribed quickly.

Patrick O'Shaughnessy

How many companies were in that first fund?

Ramtin Naimi

Probably about 55.

Patrick O'Shaughnessy

Okay.

Ramtin Naimi

What we did early on in that fund was operate a pure co-investment model. I met founders, and I now knew all the top-tier guys at all the multistage venture capital firms. For the companies that I thought were the best, I would introduce them to the relevant partner at one of the top funds and say, “I think these guys are impressive. I like what they’re working on. You know more about this category than I do. Why don’t you take a meeting with them, and if you like it, let’s find a way to work on it together? You take your 15%, I’ll take my 5%.”

I did that about 20 times perfectly. What I mean by perfectly is 20 for 20. They got their 15%, I got my 5%, I got a tier-one co-lead, and my LPs were happy. The strategy was working.

Then I started to get a little annoyed because I felt like I was doing most of the legwork and getting this 5% tax.

I wanted to find a way to start getting more ownership in these deals while still being collaborative. I still had no name at this point in Silicon Valley. It’s arguable whether I have much of a name today, but back then I definitely had nothing.

What I wanted to figure out was that the founders I wanted to work with wanted those firms on the cap table. There was no world in which I was saying, “It’s me or Andreessen. Who are you going to go with?” because I was going to lose that 10 times out of 10.

But what I started understanding was that I could lead these financings and bring the multistage firms in as a co-lead. When I led, I still left enough room for a co-lead, but I really started to stress-test how far I could push a multistage firm down on ownership before they ultimately walked away from a deal, while still being happy about it.

The number I settled on was about 10%. Pretty much every multistage, tier-one VC firm will do a seed deal at 10% if they have to. If we push them down to 6% or 7%, it’s just not worth it. They’d rather wait for the Series A.

8. Leading Seed Financings

We started leading financings more consistently, and we ended up leading 14 companies in that first fund. The first 4 deals I ever led—2 had raised follow-on from Benchmark, 1 had raised follow-on from Sequoia, and 1 had raised follow-on from Andreessen.

I had a very positive feedback loop that the deals I was leading at seed were not adverse selection, and that gave me more confidence to continue leading. The more time I spent focused on seed, the more confident I got in my ability to pick seeds versus relying on other people as a proxy.

Now we have a ton of data that shows quite clearly that the deals we have led as a venture capital firm have dramatically outperformed the deals in which we were not the lead investor but co-invested in.

Nowadays, we probably lead 80 or 90% of the companies in our portfolio. We pulled the data on every seed firm out there, and we are the firm with the highest likelihood of getting a follow-on Series A from a Tier 1 VC firm. The highest graduation rate of any seed fund from seed to Series A to a Tier 1 fund is us, by a pretty wide margin.

That was what we started to focus on. By the time we closed the first fund, it became pretty apparent that I had accidentally built probably the most well-networked LP base in Silicon Valley. I wanted to find a way to leverage that for the benefit of our founders, because that's ultimately who our primary customer is. Over time, we really started focusing on being the number one venture capital firm to get a founder from seed to Series A.

Patrick O’Shaughnessy

I'm curious how you got the capital in the AngelList days to first do those $25K to $500K deals. I'm also curious about the structure of the agreement to sell a stake in your management company that had the sunset provision in it.

I'm asking about both of these because there's always this cold-start problem with people who want to do what you've done, run their own investing firm, or get going. You solved two of those problems with these two approaches.

Ramtin Naimi

I started a venture capital firm with no money because I was literally flat broke when I started Abstract.

Patrick O’Shaughnessy

You filed for bankruptcy.

Ramtin Naimi

I had literally filed for bankruptcy at 24 years old when my previous startup company had failed. I was literally out of bankruptcy starting a venture capital firm. It's funny because, at the time, it was this humiliating experience. I put everything I had into this one company. It turned out to be the wrong category to build a company in. I pulled the plug.

Thankfully, I got a job after that, so I was able to get back on my feet somewhat quickly. But no, I didn't have parents I could rely on for seed cash to start being a venture capitalist. I didn't go to an Ivy League school where all of my friends' parents were the guys who ran every single one of these venture capital firms.

9. The Power of AngelList

I truly believe that there is no excuse for saying that there isn't access, because I think there are enough tools—at least in venture; I can't speak to other asset classes—that have really democratized access to capital. If you prove that you deserve capital, there are people in Silicon Valley who will give that to you.

AngelList is the perfect platform for that. AngelList has capital on its platform—dedicated platform capital—and if you find a deal, they'll put the money into it. I started finding deals and bringing them to the platform, and the money showed up. I was like, “This is real.”

I could bring a deal to the platform. I could write a summary on the company. I could write about the deal dynamics. Then, within 24 hours, they would say, “We raised $300,000 for this deal. We raised $400,000.”

I remember the first deal I put on AngelList. It's crazy. I was stunned the first time this happened. The first deal I ever put on AngelList, I wrote the write-up, put the syndicate up, and then sent it to AngelList. I refreshed it 4 hours later, and there was $470,000 subscribed to the deal. I was like, “Holy shit.”

Patrick O’Shaughnessy

What was that?

Ramtin Naimi

It was Rippling. This is incredible. I can't believe this actually works.

Patrick O’Shaughnessy

So the money came from the AngelList platform. You didn't source—

Ramtin Naimi

I didn't source $1 of the capital on that platform. AngelList sourced every penny of capital that came into those deals. Once I realized it was real, I just—

Patrick O’Shaughnessy

Went ham.

Ramtin Naimi

I went ham. I was looking for deals. I was hunting for deals all day long.

Patrick O’Shaughnessy

What were the economics split between you and the platform in those deals?

Ramtin Naimi

AngelList is 0 and 20 for the LPs. If AngelList sources the capital, which in my case they did in every single deal, they get 5%. I get 15%. So it's actually a great deal.

Patrick O’Shaughnessy

It's a fantastic deal. So you get 0 and 15 on all those.

Ramtin Naimi

0 and 15 on every single one of those deals. I got so excited and so jacked up by this that I got so active that, for a brief period of time—I think for a 6-month window—I was 1/3 of all the volume on AngelList. It was fantastic.

The cool thing about it was that when I stopped doing deals on AngelList and decided to raise my fund, a bunch of the syndicate investors who were actively supporting my deals were like, “What happened? Your deals aren't on the platform?” I said, “I'm starting a fund,” and those guys all became LPs as well.

10. Scaling and Building a Team

It not only helped establish a platform for me to raise a fund, but not every single founder in the world wanted SPVs, because there's a public nature to that. I still wanted to invest in companies; I didn't want to be limited in my ability to do so.

At one point, Lightspeed invited me to be a scout for them, and I put half my scout fund into the seed round at Rippling. So that worked out well. I was working at Core Innovation Capital at the time, and I had some money there and did some angel checks in tandem, too. You could literally bootstrap a venture capital firm out of bankruptcy.

Patrick O’Shaughnessy

So then you sold 20% to this consortium of the guys you mentioned earlier. How did you do that? How did you know how to price it?

Ramtin Naimi

That was one of those situations in life where I was actually quite fortunate, because there was a lot of demand for what I wanted to do. I was able to set a price, and I set a price that I thought was fair. At the time, the price seemed high to me. In retrospect, it seems low for them, right? I think those are the best deals in the world, where everyone's happy. I was happy to get the deal up front, and they're happy they made that deal at the end.

Patrick O’Shaughnessy

What was the price?

Ramtin Naimi

Just shy of 50. I had some experience with this because I mentioned that I invested in the management company of Polychain. I learned a little bit about what a management company equity financing looks like, and there were some learnings I took away from that.

The one thing that I really wanted was to ultimately own my own company. I thought that, over time, if I scaled, having the founders of every single big platform fund owning an equity piece of my management company was probably not the best thing for me long term. So we had set a sunset on that. I believe it's 6 or 7 years.

The nature of it was basically that they invest, and because it sunsets, they just got some top-of-waterfall participation in the first 7 years of my economics, or something like that.

Patrick O’Shaughnessy

They get economics on everything you did in that first 7 years in perpetuity. Got it.

Ramtin Naimi

Everything I do in 7 years and 1 day, they're not entitled to economics.

Patrick O’Shaughnessy

Yeah, got it. So it effectively lasts as long as you raise the fund in year 6. They get it for another 12 years.

Ramtin Naimi

A 7-year timer in venture is nothing. They get no carry.

Patrick O’Shaughnessy

Right, right. Most of the excitement in venture starts to happen in years 9 and 10. And then you used that capital to finance the business and build a team.

Ramtin Naimi

Yeah, we hired a team. We built a really cool back-end platform from scratch. We wanted to be seen as a very serious institution early in our fund's life cycle.

Alex, my partner, has a much more traditional background than I do. He's a Bridgewater, Columbia guy: very process-oriented, very analytical, very data-driven. Early on in our fund, we basically built a CRM from the ground up, which we're actually spinning out as a company right now because every venture capitalist I've shown it to has been like, “If this is a product, we would pay for it.”

The guy who built that for us, Will, is actually spinning that out into a standalone business. But there are a million ways, going back to this, to bootstrap your way into the venture capital world.

Patrick O’Shaughnessy

Okay. So now, if I start to think about more elements of the process here—55 companies in the first fund, 47 in the AngelList days—talk me through the process of engaging with a new company that's young, the sorts of things that you're pattern-matching on or looking for, and the things that turn you off and cause you to not be interested.

11. Identifying Exceptional Founders

Ramtin Naimi

I've learned over time that investing in founders, for me, works a lot better than investing in markets. I'm better at identifying what a good founder is than what a good market is.

There is a genetic makeup that I look for in a founding team of a company, whether it's spread among 1 founder or multiple founders. I'm looking for a combination of very strong commercial ability and very strong technical ability.

I'm not technical, but Alex on my team is technical. Andre is technical. Will is technical. They're more suited to vet the technical capabilities of an individual than I would be.

When I mention the commercial aspect, I'm really looking for salesmanship in 3 different verticals. Vertical 1 is the ability to fundraise, which seems simple, but building a startup company is hard. Anything you can do to put the odds slightly in your favor just makes your odds of success that much more likely.

There are certain founders who are good at fundraising and certain founders who are not good at fundraising. The founders who are good at fundraising get to build their startup company that much more easily than someone who's bad at fundraising.

That's obviously something you can sometimes solve for because you could help with that as an investor, but it's very beneficial when a founder has that salesmanship rigor. The next one is hiring. Hiring in early-stage startup companies is sales.

85% of the companies we finance are based in the Bay Area. They need to hire engineers who can easily get a job at Meta, Google, or OpenAI for $400,000 a year, and the seed-stage company is trying to hire that person for $150,000 a year. It takes a very specific person to convince somebody that a $250,000 annual pay cut is in that person's best interest in exchange for equity in this company that just has a concept of an idea.

That's really important because recruiting is something that I think a lot of people underestimate the importance of at the early-stage founding stages of these companies. The next one is selling a product. Oftentimes, V1 of these products are half-assed, broken, glitchy things that no one would pay for, but these founders are able to go out and find individuals who will at least be a design partner or a pilot customer and give them a shot to build something.

Oftentimes, it's not even in their best interest. It's a time suck. They will say, "Come back to me when there's actually a working product," and convincing somebody that it's actually worth spending time with them to perfect the product is also a specific type of individual.

On the technical side, we're looking for someone with extremely strong technical capability whom other engineers would actually work for. Some people are great engineers whom other engineers might not necessarily want to work for, and other people are great engineers—or maybe not, maybe they're just great engineers—whom other engineers would happily work for. What I look for on that side is shipping velocity. Is this the kind of engineer who's going to ship a product in 6 weeks or 6 months?

At the end of the day, I think seed-stage investing, at least for us, is very momentum-driven. I want to build a portfolio of 60 high-momentum companies and hope that 3 to 5 of them reach escape velocity and become amazing companies.

12. The Importance of Dilution Sensitivity

Another thing that I've started to gravitate toward over time, which is a little counterintuitive to being a venture capitalist because you want to own a lot of these companies, is that I've found I've had a lot of success with dilution-sensitive founders. What I mean by dilution-sensitive is that you meet two buckets of founders at the seed stage. You ask them what kind of round they want to raise, and they're like, "A typical $5 million, $25 million post-money round. I'm down to sell 20 to 25% of my company. Pretty standard."

I'm like, "I don't think there's anything standard about selling 20 to 25% of your company at seed. You don't have to sell 20 to 25% of your company. Do you need $5 million?" Then there's the other founder who comes in and says, "I need $3 million, and I want to sell as little of my company as humanly possible for that $3 million."

I found that those founders tend to be a little bit more high-conviction in what they're building. They tend to believe that every percentage of equity they give away is 1% of equity they'll never get back. That's incredibly powerful because, more so than negotiating with investors—which is great—they tend to maintain the highest bar of talent that they hire because they think about equity the same way, whether it's going to an investor or an employee. They want to make sure everybody they hire is worth every ounce of equity they get.

Those founders also tend to be the ones that aren't wasteful with their equity. If someone's not working out, they're going to fire them before their 12-month cliff, so there's not deadweight equity with 30 to 40 people who no longer work at the company. That's also really great from an IRR perspective on your investment because it means that the option-pool refresh in the next round is not as big as it would have been if they had just loosely given away a lot of equity.

I will say those founders who are the dilution-sensitive ones in my portfolio, who have the highest bar for the talent they hire—the companies in my portfolio where all of those things ring true and the companies are doing quite well—people are always shocked at how small the teams of those companies are relative to the scale of what they've achieved. I truly do believe incredibly high-quality talent has a multiplier effect on company efficiency.

Patrick O’Shaughnessy

13. Efficient Investment Processes

How fast do you work your way through one of these? How much time, measured in hours or whatever, do you spend with the founding team before making an investment?

Ramtin Naimi

Typically, it varies, but it's somewhere between 3 and 4, sometimes 5, meetings, and then doing a lot of back-channel work in between those meetings. Sometimes you have the time to do that; other times you don't.

Having said that, the way our firm is set up, we have standing meetings multiple times a day. Our whole firm is designed around speed, and we've built our model around being able to do what might take another venture capital firm 2 to 3 weeks in 2 to 3 days.

Patrick O’Shaughnessy

Okay, so talk through that. I want to hear the cadence of a week at Abstract. If I just walked through the office halls for a week, what would I see?

Ramtin Naimi

Tons of pitch meetings. That is what I think our time is best spent doing: pitch meetings and then helping our existing portfolio.

Patrick O’Shaughnessy

Founders pitching you.

Ramtin Naimi

Founders pitching us. I always tell people it's not a flex to get a meeting with me because I pretty much don't say no to meetings. I probably take anywhere between 18 and 30 pitches per week.

Patrick O’Shaughnessy

Wow.

Ramtin Naimi

It goes back to Michael's phrase, "frame of reference."

Patrick O’Shaughnessy

The more companies you meet, the easier it is to spot the people who truly stand out.

Ramtin Naimi

Obviously, you miss things over time, but I think—

Patrick O’Shaughnessy

It's hard to know what great looks like without seeing a lot of things.

Ramtin Naimi

I also find that the VCs whom I believe are the most successful VCs and have had the most storied careers tend to be the people who take every single introduction I send them. The VCs who are still building their careers, when I send them deals, are like, "I'm a little swamped for bandwidth right now." I'm like, "All right, that guy's not going to make it."

It's pretty obvious who really wants to meet Roelof at Sequoia. I think you heard this line from Doug Leone. When I first met Roelof, he told me that in order to be successful in venture capital, you have to have Dumbo ears, which means you have to hear everything or see everything.

I saw Neil's podcast yesterday where he was talking about how they don't care about coverage. I think that could be true at the growth stage. I think at the seed stage, coverage is absolutely key because there is no market map of everything that exists. Most of these companies don't even have websites yet. There is nothing to go on.

You really just need to have your tentacles everywhere to get as many companies as possible surfaced up to you. There is so little that exists about these companies that there is very little work you can do to qualify or disqualify them in advance. You really just need to spend time with them.

Patrick O’Shaughnessy

What are the standing meetings that you have with your team, the internal ones?

Ramtin Naimi

We have a 30-minute meeting at least once a day to catch up on every company people have met with that day because we meet with so many companies that it's very easy to forget what was interesting. On a daily basis, we're just syncing up: has anybody met with anything that other people on the team should meet?

Patrick O’Shaughnessy

In the meetings themselves, do you have favorite questions that you find yourself returning to again and again to ask founders?

Ramtin Naimi

The number-one thing that I look for from founders is a sign that they're exceptional. What I mean by that is, if you look at the most successful, impressive founders out there, they tend to have been impressive—not necessarily successful, but impressive—people prior to starting that company. They had a history of doing special and impressive things.

There was this famous question on Quora once upon a time. Somebody asked, "Is it true that nobody's ever started a successful company after 35 years old?" In Silicon Valley, everyone says that all the power-law companies are founded by younger individuals, which has some truth and also doesn't. The people who answered that question included Reid Hoffman: "I founded LinkedIn when I was over 35." Marc Benioff: "I founded Salesforce when I was over 35." Reed Hastings: "I founded Netflix when I was over 35."

Every single one of those people had been very successful by the time they started those companies. It's hard for me to believe, if I meet somebody and I can't get a sense that this person is special, or has been special, or has done impressive things in their life, that the first impressive thing they're ever going to do is this company they're asking me to invest in.

Patrick O'Shaughnessy

Do you literally ask them, "Tell me the most impressive things you've done"?

Ramtin Naimi

I ask, "What are the entrepreneurial things you've done?" I ask them to tell me their story. If there is something impressive in their story, they will make sure it stands out.

Sometimes the special thing is that they got into the school of their dreams. So did everybody else who went to that school. I'm looking for something that's truly different.

Resilience is key. That's a little harder to discern, especially with the age of founders that I back. Not everybody's had a situation where they've had to deal with hardship to develop that resilience. But some of the founders in our portfolio have done pivot after pivot after pivot, have survived for years, and then ultimately started a company that had nothing to do with their first company and ended up being very, very successful.

Now, I'm not saying that every founder should stick with every single company over a certain period of time. There are founders who should absolutely stop working on a company, either return cash or find a soft landing, and move on. But there are other founders who will just do these non-local pivots. I think the local pivot is what kills companies.

An example of this: We invested in a company called Poparazzi. Do you remember that one?

Patrick O'Shaughnessy

Sure.

Ramtin Naimi

Yeah. We had seeded them when it was TTYL. Then TTYL pivoted 5 or 6 times until it turned into Poparazzi. Poparazzi launched—I think it was the first consumer social application ever to debut at number 1 on the App Store. By the end of that day, they had 3 term sheets from 3 Tier 1 VC firms, and they signed a term sheet with Benchmark.

Within 6 weeks, it became very obvious that there was no retention. The growth was there, but the retention wasn't there. He just returned the cash. He had all this money from Benchmark, and nobody was telling him to shut the company down. But he was like, “I've only been thinking about consumer social for the last 3 years. I know that if I pivot again, it's going to be another consumer social idea because my brain is wired to do that right now.”

“So I need to shut this company down. I need to return cash, and I need to just go back to the drawing board. If and when I come up with another company, I'm going to come back to you with a seed round so I don't have this Series A valuation hanging over my head.”

There are other founders who have just churned their entire team, maybe even half their founders, but maintained the balance sheet and went into skeleton-crew mode until they figured out things that had nothing to do with the first version of their business. Clay is a really good example of that.

Patrick O'Shaughnessy

I think we wrote a small check into the seed round of Clay, I think, about 8 years ago.

Ramtin Naimi

And then I think they hard-pivoted 2 years ago into what Clay ultimately is. Vapi is a company in our portfolio that was originally called Superpowered. They're doing very well. They've scaled from zero to double-digit millions of ARR within 14 months of launch, but that was 4 years after I seeded them and 7 pivots later. Krea is another example of multiple pivots until they finally caught fire with the latest version of their product. Krea was originally called Geniverse.

Patrick O'Shaughnessy

At the beginning, you told me a line about art one time, something like, “All good art is ugly,” or something like that. Do you care much about the idea, or are you really, really focused on the attributes of the founder?

Ramtin Naimi

The idea needs to be thematically interesting to me, not be in an overly saturated market, and show some sign of novel thinking. What I mean by that is, there is this weird phenomenon in Silicon Valley that every time a Tier 1 fund, or maybe 2 Tier 1 funds, finance a company in a category, in the next 3 months I'll get pitched 15 companies doing the exact same thing.

It's very hard to discern whether that person truly wants to build a company in that category or whether they just want to be a venture-backed founder and know that there is capital available for this category right now. Oftentimes, I'm looking for signs of novel thinking. Either it needs to be one of the first 1 or 2 times I've heard this company pitched to me, or it's being pitched to me with a completely brand-new perspective—a perspective that I haven't heard before and that I think means this person truly thought about what they were trying to build.

When I go back to it, the specific idea is less important to me. It's more about the founder's understanding of the idea. It's very easy to understand how thoughtful someone has been about anything just by questioning them. There are certain founders you ask questions to, and their questions lack depth and their answers lack substance. You end up in these situations where I'm like, even when I ask you the question, the answer still isn't a real answer. I don't actually feel like you even know the answer.

Then there's the other founder who you ask a question, and they can give you a 15-minute-long answer to every question you ask. It's like, no, this person is clearly either being asked this question for the 5th time or has asked themselves this question 10 times already and thought about every angle to it. I'm not saying that that's absolutely necessary, but at least it shows me that they've actually come to this with a first-principles mindset and truly thought a lot about building this specific company.

At the end of the day, I also try to look 18 months into the future. If this company does well, how many investors do I personally know who will be interested in leading a follow-on round of financing for this company? If it's a company that 3 Tier 1 funds have already led a Series A or Series B financing in, most of those Tier 1 funds are going to be more interested in following on to one of those companies than the new company.

There are certain times where maybe it's a mistake, where I just believe a category is too saturated and the risk-reward ratio isn't quite there.

Patrick O'Shaughnessy

Okay. So now we get to the point where you like a company. How do you think about the pricing for a round that you will tolerate? There's some degree to which you're a price taker. There are market prices for these things, and those ebb and flow. Are you basically a price taker, or do you have limits to what you'll do?

Ramtin Naimi

If there's a multistage fund around the table, the deal will get done no lower than 25, and it'll probably get done no higher than 50. If it gets done higher than 50, it means one multistage fund got really excited and just turned it straight into a Series A, at which point it's not really a fit for me anymore. And that does happen. The 50 is something I actually need to take into consideration because every venture capital firm has a portfolio construction model, right?

My portfolio construction model says that I want to own 8% to 10% of 60 companies at seed, and I want to maintain that 10% ownership in the best 10 of those companies through Series B. Now I have assumptions for what my entry valuation needs to be into these companies. It used to be that I wanted to maintain an average entry valuation of sub-$20 million. I used to be able to do that, but I can no longer maintain an average entry valuation of sub-$20 million.

Maybe my average entry valuation today that I want to maintain is sub-$30 million. That means sometimes I'll do a deal at 15 post because I found a deal that was off the beaten path and it's a pre-seed. Maybe I took an early bet on people. For some, I'll do a deal at 50 post. But if I can maintain an average entry valuation of sub-$30 million, it'll be nice.

If you start doing too many deals that are north of 30, you start messing up your portfolio construction model because the more deals you do over 30, the fewer shots you have on goal, right? If my goal is to have 60 companies per fund and suddenly my entry valuation starts to deviate from what I modeled in my portfolio construction model, then I need to start asking myself, “Is investing in this company worth losing 1 shot on goal out of this fund?” That's when you need to start thinking about price a little more discerningly.

Sometimes the answer is yes. I'm just like, “I want to invest in this company. This company needs to be in the fund.” You kind of need to convince yourself that you like it twice as much as another company in your fund because you're basically shooting 2 bullets at 1 deal.

But once we've decided to invest in a company, price tends not to be something that dissuades us from investing in that company until it gets so egregious that you can no longer call it a seed deal. That's basically our point of view. Obviously, we try to get it to fit within the confines of our portfolio construction model, but oftentimes you have to deviate from that to get the company into your portfolio.

14. Winning Competitive Deals

Ultimately, venture is an outlier's business, and you have no idea if the deal that you passed on due to price will be the outlier. You kind of just have to swallow the bullet sometimes.

Patrick O'Shaughnessy

Now we come to winning. You have to convince the founders to take your money and not other people's. I love this idea that the pitch you give to founders, which is increasingly proven true, is that by taking your money, they're effectively getting a fantastic fundraising partner for the future, and that you and Abstract are lowering their future cost of capital. Talk us through that pitch that you give and then how you execute against it.

Ramtin Naimi

Competing for deals is very challenging. I think it is an incredibly time-consuming process, and for us, competing is a very labor-intensive process because, as you know, prior to doing this podcast, there's nothing publicly available about me on the internet, period.

Pretty much all of the selling I need to do is explain to the founder who we are and what we do, and have 7 or 8 of my other founders call them and explain the benefits of working with us. They tell them that if they were to start a company again, they would absolutely come back to us for their seed round.

When we do decide to win a deal, we really do go all in in terms of how much we're putting behind it to make the case to the founder that we are their best seed partner, period.

In addition to fundraising, we have a full platform team now, as anybody else would expect from a large seed fund that we have today. We have an incredible head of GTM, an incredible head of comms, and an incredible head of talent. We can help with all of those things, but what we really wanted to do was be exceptional at one particular thing, or at least what I wanted to focus on. I think everybody on our team specializes in their own specific things, but the one process that I thought was broken in the venture ecosystem when I first got into this was the fundraising process.

You're an investor, so you've seen these spreadsheets before. When a founder wants to fundraise, they put together a Google Doc and share that Google Doc with all of their investors. On that Google Doc, in the left-hand column, there's a list of every single venture capital firm they want to talk to. Then they ask all of their investors to go through that list and say, “Please mark whether or not you have a relationship with one of these venture capital firms, how senior your relationship is, and how close you are with that individual.”

The founder will go through that list at the end and ask 9 of their investors for intros to 30 different venture capitalists, and they'll kick off their process. The reason I thought that was bad was that there are too many people involved in the fundraising process and too many potentially misaligned incentives, right? This potential investor might have a really close relationship with this VC. They might be trying to do their buddy a favor by helping him win a deal.

Too many people work at these venture capital firms, and that's too many young people telling their friends about who this fund is talking to, who's passing, who's not passing, and what the valuations are coming in at. VCs are just trying to gather as much information as they possibly can. When you choke off that information, then they're forced to really just do their own work and truly build conviction in a company. They tend to work faster this way.

After I closed my fund, as I mentioned, and with all the LPs we had, it became pretty apparent to me that I was the person in Silicon Valley who had the direct line to the most senior GPs at every single one of these venture capital firms. In the early days, I got some of my founders to trust me, and I'd say, “Listen, let's not bring anybody else into the fundraising process. I will be the sole node. I'll help you with the deck, and I'll help you with the data room. Let's do a few mock pitches with people on my team.”

“I will make introductions to every single top GP who is the relevant partner at each of these venture capital firms for your company. We'll line up all of these meetings over a 3-day window next week. At the end of every single day, I will check in with all of them, get feedback, find out what's resonating, what's not resonating, and who's truly interested versus who's not interested. We'll keep the process going, keep it tight, keep it efficient, and avoid any information leaks. Then we'll try to get you the best deal possible.”

Ultimately, what I try to do is get as much leverage for my founders as possible. Leverage comes in the form of term sheets. The more term sheets they have, the more negotiating power they have. Everybody wants negotiating power and to make a good deal for themselves, their company, and their existing shareholders.

When you don't have leverage, you will sell 25% of your company at Series A to whoever gives you the terms that you want to work with. When you do have leverage, you can get that down dramatically. What I thought could be the number-one value-additive thing that I could do for my companies was make sure that, by the time they exit, they own more of their company than they would have had I not been on the cap table.

Now we have data showing that not only do we have the highest graduation rate from seed to Series A, but we also have the highest decile of average valuation at Series A and the lowest average dilution in the Series A. We can basically give your company way better access to lower-cost capital in the future from the highest-quality partners.

I had one of my founders do a reference with another founder, saying that the likelihood that you own 10% more of your company at exit is 10x higher with Abstract on your cap table than without it. If I can save you 5% at the A, 3% at the B, and 2% at the C, these things tend to add up nicely. If you end up exiting your company for $2 billion and end up with an extra $200 million in your pocket, I can't personally think of a single value-add that a venture capitalist brings to the table that translates to more than an extra $200 million in your pocket.

Patrick O'Shaughnessy

Having done so many of these where you're helping a founder raise, let's focus on Series A to start, because that's what follows what you do. What have you learned about running these processes? I'm interested in the very nitty-gritty details, like what time of night to call the VC to get feedback, or how to solicit true feedback that's not whitewashed or something.

Ramtin Naimi

I think I've been doing it for long enough that I have very trusted parties.

Patrick O'Shaughnessy

They'll just tell you at every venture capital firm?

Ramtin Naimi

They'll just tell me.

Patrick O'Shaughnessy

But how did that start?

Ramtin Naimi

In the early days, it was really just a lot of, “Who is this kid? Why is he running these processes? Why are these people trusting him to run this fundraise? Why is he the gatekeeper for this round?” Over time, it just became accepted that I was that person.

I think the definitive thing that proved that I'm the accepted party to do that, whether it's at the A, the B, or the C, is that we've proven to do such a service for founders when we're running these processes for them that even in deals where our co-lead is a multistage, tier-one, big-name platform fund, when that next round is coming, they will tell the founder, “We're more than happy to let Ramtin/Abstract run this process because they'll do a better job at it than anybody else will.”

Once we got the validation from our co-investors that they thought we would do a better job running this than they would, I think it just became accepted that, for our portfolio companies, this is the way it's going to be.

Patrick O'Shaughnessy

So you're sort of the czar now for this process.

Ramtin Naimi

Yeah, that's a fair way to describe it.

Patrick O'Shaughnessy

What have you learned about the dynamics of who tends to win at Series A when they want to?

Ramtin Naimi

There are different types of ways rounds come together, right? There is the typical process where the founder puts together a deck and a data room, lines up meetings with every single venture capital firm, and goes out and pitches. Then there are deals that happen outside of that dynamic, where we have less involvement.

Oftentimes, we help our founders build relationships with certain VCs in advance of the Series A process, because that's actually a good way that we get information on what those people would want. What should be this company's North Star metrics? How should we know when this company will be ready to raise a Series A?

Oftentimes, one of those people will just come in and preemptively make the founder an offer. The founder likes this partner, the terms are fair, and they don't want to spend the next 3 to 4 weeks of their life fundraising, so they call it a day and move forward. I think certain VCs are very, very good at doing that.

But in the bake-off process, when there are 15, 18, or 20 firms around the table, very few companies end up getting more than 3 or 4 term sheets. There are a few companies that get 7, 8, or 9 term sheets. The firms that I think truly excel at winning hypercompetitive Series A rounds, based on what I've seen from my experience over and over again, tend to be Sequoia, Benchmark, and Andreessen.

Even to this day, somebody pulled out a statistic and shared it on LinkedIn the other day that I looked at. It showed the VC firms that have led the highest number of financings in companies prior to those companies becoming unicorns since 2015. First place was Andreessen, and second place was Sequoia, which validates this truth already. Fifth place was Benchmark, which is kind of shocking when you consider how much smaller their fund is and how targeted they have to be with the checks that they write.

Typically, when one of those 3 firms extends an offer to a company, they tend to win unless they're competing with one of the other 2. Then they tend to only lose to one of the other 2. If you eliminate those firms, then it's kind of a free-for-all, and there are certain people who are more qualified to win certain deals than other deals.

Patrick O'Shaughnessy

If you eliminate that dynamic, there are plenty of companies that could have absolutely raised a Series A from one of those firms that somebody else ends up winning, but they preempt the deal and are just very good at sniping deals. I think those 3 individual firms have built brand weight that's so strong that founders really just want to be affiliated with them.

There are certain partners at those firms who have such amazing reputations as board directors that a Series A is the first time you're giving up a board director seat. Not to say there aren't phenomenal board directors at a bunch of firms, because there really are.

Ramtin Naimi

But the density of high-quality board members with storied reputations for being great board members at those 3 particular firms, I think, outweighs the number of high-quality board members that exist at pretty much any other venture capital firm.

15. The Value of Strong Board Members

The advice founders get from their seed investor is that, in addition to optimizing for a good deal for yourself at the Series A, you really should be optimizing for who’s going to be the best board director to have on this journey with you for the next 10 years. In the early days of Andreessen Horowitz, every single one of the founding partners was an operator who had sold companies for hundreds of millions of dollars, right? It was hard to compete with: this guy is going to be on your company, and he knows exactly what it takes to build a successful outcome in venture capital.

And then, alternatively, Benchmark and Sequoia have some individuals like that, but they also have individuals who have been on the boards of the most successful, most incredible outcomes in Silicon Valley history. So they have a much better sense of what exceptional looks like, more so than other people. They know things that work, and they know things that don’t work.

There are great board members at every venture capital firm, and they’re all very public. You know who they all are. There are a lot of people at those venture capital firms who don’t have those experiences, who haven’t sold a company and haven’t yet been affiliated with a great company. Those guys will do great, and some of them will join boards and become one of those people individually. But when a founder is choosing, they’re more likely to choose the person with that experience than the person without it.

Patrick O'Shaughnessy

If you took a snapshot today of Abstract and had to go out and gather feedback from everyone who engages with the firm—founders, LPs, other venture investors, other random people—and bucketed all that feedback into a spectrum, what would the most complimentary people say, and what would the most critical people say, do you think?

Ramtin Naimi

Sure. I would say the most complimentary people would say that we’ve become one of the leading seed firms in Silicon Valley in a relatively short period of time. We have a great reputation among our founders. We’re routinely referred to as the most trusted investor on the cap table of our portfolio companies.

I think a lot of the multistage firms would consider us their most trusted seed-stage venture capital firm partner. I think some would say that we’ve achieved a lot more success than other people who have started a venture capital firm in the same amount of time that we have.

I’d say the people who would say critical things would probably say that we’re heat-seekers, signal chasers, which wouldn’t have been inaccurate if you had said that 6 or 7 years ago. A lot of the model was aligned around, “How do I get into deals alongside those firms?” Candidly, I had to do that because I wouldn’t be able to raise SPVs otherwise, right? That’s why I got the LPs to invest the money they did, right? That was my go-to-market strategy.

But over time, I think we became the signal. I think people still tend to hold on to old narratives, so I could totally see that being the case. In the earlier days, we were high-volume. We’re not anymore as a firm. I think we invest 14 net-new seed deals per year, which is a little over 1 deal per month.

I don’t think we’re high-volume today by any means, but again, people tend to stick to old narratives. People will say that we’re high-volume and they’re all call options, which I would just say is not true.

Patrick O'Shaughnessy

I can’t help but think about all the different art-world analogies that you’ve built very quickly: a talent spotter, an up-and-coming gallery. So, of course, it demands the question: when and if you’ll become Gagosian?

Ramtin Naimi

I think Gagosian has a really cool story. He was a total outsider with no relevant pedigree, and he was kind of just dismissed for his first few years—or first decade—until he ultimately became the leading guy in the category.

Now, I’m far, far, far away from that, and I think Silicon Valley is a friendlier place than the art world. Silicon Valley has been nicer to me than maybe the art world was to Larry Gagosian in the early days. So I don’t want to draw the direct analogy, but I think the main thing is just staying consistent, maintaining the reputation, building upon that reputation, and then producing great results.

Patrick O'Shaughnessy

Venture is the only asset class where historical results are somewhat indicative of future performance.

Ramtin Naimi

And you can actually somewhat forecast how a venture capital firm will do over time based on how they’ve done historically. So I do believe if we just stay consistent, we have a pretty long trajectory and a long career ahead of us. I’m 34 today. I started this when I was 26. I think I have at least 20 years left in me to keep doing this.

I think you could build quite a brand and quite a platform in that time frame.

Patrick O'Shaughnessy

What feels missing from the core machine today? You mentioned speed being an objective function that you optimize around a lot. If you could just snap your fingers and improve some aspect of the Abstract platform, what would you improve or change?

Ramtin Naimi

It would be brand. I think brand would trump anything else that the machine doesn’t have today, primarily because when a founder comes to us referred by an existing portfolio company, most of the work is done for us.

You’re not going to find much about these guys online, but they’ve been phenomenal partners to me. They’ve opened doors for me. They’ve knocked it out of the park on our fundraise. They brought together the most solid angels to fill out our cap table, and he’s always available when I need him for anything.

If we don’t have that and we’re cold-reaching out to founders, it’s much more of an uphill battle to convince them why we should be in the same conversation as all the other venture capital firms they’re talking to, whose names they’ve heard before. That’s why I mentioned that winning deals for us is a very manual process.

Other firms just get to win because of their brand. I have to spend the man-hours and call in all the favors I have to in order to win the deal. So part of the reason I’m doing this is coming out of obscurity.

Patrick O'Shaughnessy

Yeah.

Ramtin Naimi

But I think that’s really the missing link. There are other people who work at the firm, and you mentioned this earlier: you hear my name more often than Abstract. I really do want the firm to be Abstract.

16. The Importance of Personal Branding in VC

I think that’ll be beneficial because scaling a platform and scaling a team helps when everybody on the team can do things—when everybody on the team can go out and compete, win, and support their own portfolio companies. If there is brand weight that they can all leverage to compete, that allows them all to have more of a level playing field in doing their jobs.

Patrick O'Shaughnessy

Say more about that tendency for individuals to have more of a so-called “brand” these days as investors than firms. Another VC explained this to me once, and I asked him how he identified whom to hire for his venture capital firm. He said he tends to optimize for people who either already have personal brands or have the ability to build a personal brand.

He’s at a very good venture capital firm with a strong brand, but he was the one who actually explained to me that Sequoia, Benchmark, and Andreessen Horowitz have incredibly strong brands. If you’re a less well-known individual partner at Sequoia or a less well-known individual partner at Andreessen Horowitz, you can still compete and win some of the most competitive deals in Silicon Valley because of the brand that you’re affiliated with.

He said, “Now, the amount of time and resources it takes to build a brand that can compete with those firms on brand is counterproductive to what it takes to be a great venture capitalist. But building a personal brand is something you do in tandem with being a great venture capitalist.”

Then I asked him to explain. I was like, “Elaborate: what’s the difference between a personal brand and a venture brand?” He goes, “Well, I hear the name Ramtin multiple times a week. I hear the name Abstract once a month. That’s the difference between a personal brand and a venture capital firm brand.”

He goes, “People know who you are. Founders know who you are. VCs know who you are. You have a reputation. There are companies that people associate with you. There are skill sets that you have that people associate with you.” People who have personal brands at venture capital firms tend to be able to compete for competitive financing rounds.

If you look at every venture capital firm, excluding those top 3—and even in those top 3, this tends to be true more often than not for the most competitive deals—when those firms are competing for a hypercompetitive financing, it tends to be the same 1, 2, or 3 partners who tend to do most of the selling and closing for those deals to bring them home.

Very few venture capital firms have more than 1 or 2, and at most 3, individuals who can independently go out and source, compete, and close financings in the most competitive deals. That’s why venture is hard to scale as an asset class.

That’s why a lot of LPs look at these large platform funds and say, “If I could just invest in these 4 GPs, that’d be way more appealing than investing in 16 of them and having exposure to the other 12 when I really just want exposure to these 4.”

Again, it’s like the art thing with the paintings.

Ramtin Naimi

Yeah, exactly.

17. The Health of the AI Investment Ecosystem

So, yeah, there's tons of analogies. I do think there are certain individuals that you meet who tend to be charismatic, trustworthy, and have good judgment, and who will have an ability that, given enough time and opportunity, allows them to build a very good reputation and a personal brand for themselves as well.

Patrick O'Shaughnessy

Do you think this whole ecosystem is in a healthy place?

Ramtin Naimi

Yes and no. People argue that these AI companies are raising at astronomically high valuations, and I actually don't know if that's true. I don't think anybody will know if it's true for another 3 or 4 years because, while the multiples seem insane, the companies are also growing at unprecedented rates.

Historically, you could look at a SaaS company and say, “Well, if it's growing 3x or 4x year over year, and you could project 5x growth over the next 2 years, you can justify paying this price today.” With AI companies, it's, “This company grew 20x year over year last year. It's on track to grow 15x year over year this year. Maybe it grows 10x year over year next year.” What kind of—what is the fair multiple to assign to that deal? It's kind of hard to determine what the correct answer to that is.

But there's also way less predictability in its potential growth, right? There's no shortage of application-layer companies that become obsolete overnight when they become a new feature of one of the foundation-model companies. So, a company could have grown 20x last year and 10x this year, and then shrink next year.

I think, at the end of the day, with venture, you're trying to capture outliers. If the companies are shaping up to be the next power-law companies of the future, you'll do whatever it takes to get into one of those companies. So, for the follow-on rounds, I will say that I don't think it's in a bad place because these are truly incredible companies growing at truly unprecedented rates and achieving adoption that no one ever thought was possible. They clearly have unbelievable signs of product-market fit very early in their life cycle.

18. The Kindest Thing

So, that's the side that I wouldn't say is healthy or unhealthy. I'd say it's undetermined. I'd say it's good for the asset class overall. If you're investing in companies that are growing this fast, LPs will ultimately do well. Will they do as well as they would have if these companies were invested in at half the price and double the ownership? Sure. But markets get efficient over time, and I think venture as an asset class is getting efficient. Efficiency brings returns back to the mean, and then you're starting to invest in managers that you think could find alpha in one way or another.

The part of the ecosystem that seems unhealthy to me, and is very reminiscent of 2021, is the timeline from graduation from seed to A, A to B, and B to C. In the last 6 months, I think I funded 7 companies that have already raised Series A rounds within weeks of me leading their seed financings, and at a 4x to 5x multiple of what I financed the company at just a few weeks prior, with not a whole lot of fundamental business progress in that time frame. That hasn't happened since 2021.

In 2021, I was funding companies and, within a couple of months, the Series A got done. That is very actively happening again. I'm funding companies that are raising As within a couple of months and then Bs within a couple of months after that. If you look at the company relative to what I invested in versus what the company is today, they're basically just paying 10 times the price for the same exact company I invested in a couple of months or 4 months ago, plus or minus a few hires and maybe some design partners.

So, I do think the industry is getting a little drunk on IRR. The same thing that happened in 2021 is happening again. In terms of my latest funds, they're getting into J-curve territory and are coming out of the J-curve way too quickly. I think in venture your IRR should be back-loaded.

19. Early Life and Entrepreneurial Beginnings

Exactly. Right. In the 2021 vintage and the latest vintage, our funds are getting to 30% to 40% IRR within the first few months of initial deployment, which just shouldn't be the case. There should be negative IRR for at least the deployment period, right? The velocity at which companies are raising follow-on funding is a little jarring.

Patrick O'Shaughnessy

If I rewind back to before age 26 and think about the rest of your life, what are the things that have happened to you that have most made you who and how you are?

Ramtin Naimi

I had a very nontraditional, by Silicon Valley standards, childhood. My parents are Iranian immigrants. My dad immigrated pre-Revolution, and my mom post-Revolution. I have an older brother; he's 5 years older than I am. We grew up in Los Angeles, just outside Calabasas.

My parents were small-business owners while we lived in L.A. My father owned a couple of restaurants and a couple of dry cleaners, and my mom was in school to be a dental hygienist. When we moved to the Bay Area, because that's where my mom had a sister and she wanted to be closer to family, I was probably about 12 or 13 years old.

My dad is an immigrant coming from another country, so my parents were financially motivated. He kind of, at an early stage, instilled in me that America revolves around money and that you need to figure out a way to make it. I heard it a little too often as a kid.

One of the things that I could point to when I was younger was the stock market. For whatever reason, my dad always had CNBC on in the mornings before school started, and I always saw it in the background. When I was 13 years old, my dad and my mom were kind enough to lend me $2,000, and I wanted to teach myself to trade stocks. I quickly learned that $2,000 was not enough money to trade stocks, and I wanted to learn to trade derivatives instead. I learned that the multiple potential of derivatives was orders of magnitude greater than what you get in the stock market. I did that throughout high school.

I also had a couple of cool high school jobs. I only had 2 real jobs in my life. Job number 1 was when I was 14 years old: I shelved books at the local library. Job number 2 was that I worked at West Elm, the furniture store. That's actually my wife's favorite story about my upbringing because of the way I did sales.

Patrick O'Shaughnessy

Tell us. How'd you do it?

Ramtin Naimi

At West Elm, I had this job when I was 16 and 17 years old, and I used it to finance a side hustle, which I'll tell you about in a second. Everybody at West Elm had a corner of the store, and every corner was its own version of a style of an apartment that you could have.

I worked there on the weekends, and I always kept an eye out for people who came to Marin from the city in Zipcars. They rented a car clearly to take some furniture home, so I always spotted the people who rented a car because I knew they were there for a mission.

When they came in, West Elm wasn't commission-based; it was incentive-based. You didn't get a percentage of your sales; you got a progressive bonus based on the size of a sale. You were incentivized to upsell people. If a sale was $500, you got a $10 incentive. If a sale was $1,500, you got a $150 incentive. So, the incentives graduated exponentially.

Somebody would come in and want to buy a sectional, and they were ready to take it home. Staging is everything in those stores, so I'd be like, “Do you guys want to take home the pillows? Do you want to take home the coffee table? What about the rug?” They'd say, “No, no, no. We just want the sectional.”

I would take everything off of it just to show them what it would look like when it got home. Then I would constantly encourage them to take it because they would be very unhappy with the way it looked when it came home. There was no harm in returning it because, unlike commissions, incentives weren't rolled back when things were returned. So, I focused on that.

West Elm had a lot of very low sectionals and sofas, and I would ask them if they had a coffee table at home. I'd say, “Is it a low coffee table?” They'd say, “No.” I'd say, “Well, have you ever seen a coffee table that's higher than a sectional? You need to prop your legs upward. It's not going to look good. It's not going to be comfortable. You should take this coffee table also.”

I ended up having the highest average ticket sales at West Elm. The hourly rate was nothing compared to what you got on those incentives, so I really just focused on upsizing those sales.

For half a summer and half a school year, I actually opted to go to the stockroom because I was able to get more work done in the stockroom since you weren't on the floor all day long. That's when I actually got an appreciation for hard labor because, as I mentioned, West Elm was one of those stores that stocked everything.

They had a deal with UPS. Every morning, UPS would pull up a truck, and the stock guys would unload it and put it in there. That's just how they made the inventory.

I remember this was probably the single hardest day of physical work I had in my life. Our manager said, “Tomorrow we have 4 trucks, so we staffed 6 stock guys to unload these 4 trucks. It's going to take half the day, and we're going to call it a day.”

The guys at UPS didn't actually unload. The deal was just to drop the trucks off and then pick them up when they were empty. Everybody showed up the next day, and everybody called in sick except for me.

And I had to single-handedly unload 4 UPS trucks’ worth of furniture. I started at 7:30 in the morning, and I think I was there until 7:30 at night. For whatever reason, I ended the day very proud of myself, even though I don’t know if I should have. I really appreciated what hard work was.

Patrick O'Shaughnessy

Well, I do think there’s a concept of working hard and smart. I do think you have to do both.

Ramtin Naimi

I think hard work is just something that was always instilled in me at an early age. I think founders work hard. I think you have to build hard to build anything of value or anything of success. I think there are certain people who are willing to work that hard and certain people who aren’t. I would argue that the 5 people who called in sick that day weren’t willing to work that hard, and they probably haven’t really gone much further in life than that West Elm stockroom.

My side-hustle business was where I actually made most of my money in high school. I grew up in Marin County, which is a relatively affluent area, and there are some people who are a lot more affluent than others. There were certain girls whose parents would throw them very extravagant Sweet 16s, and there were other girls whose parents wouldn’t throw them one. I saw a hole in the market there.

My high school business was that I would finance birthday Sweet 16s for anybody who wanted one. I did this for a couple of years, between the ages of 16 and 17. I would rent out a venue and get a DJ, and my only condition was that they could invite anybody they wanted. It was going to be their birthday, their name was going to be on the banner, and the DJ was going to do shout-outs to their name. But I got to charge a cover charge, and I also got to make the party dramatically larger by inviting anybody from every other high school in Marin County.

I turned this into a real business. I would get the venue, get insurance for the venue, and go to the local gym to get the roided-out meatheads. I’d give them $50 for the night, and they would block the side doors so nobody could sneak in. I spent so much money on the first party that my parents were worried I was going to lose all the savings I’d saved up to throw that one event.

The funny joke was that I had a pencil box to collect all the cash. Within about 10 minutes of the party, there was too much cash, and I couldn’t close the pencil box anymore. I ran to the bathroom, took out a garbage bag, and started stuffing it with cash. That became a business that ran for the next couple of years, until it didn’t really make sense to host parties anymore.

Patrick O'Shaughnessy

How much money would you make on a party or something?

Ramtin Naimi

I would net $2,000 a weekend, and I would do 2 to 3 parties per month. It was a good little side business for high school.

20. Starting a Hedge Fund and Lessons Learned

Patrick O'Shaughnessy

Talk to me about the experience of starting a hedge fund and getting a little bit more serious about the investing side of things from a young age.

Ramtin Naimi

It wasn’t until my senior year of high school that I actually made money trading. I got very fortunate through a combination of lucking out with volatility and not understanding risk management while trading out-of-the-money call options and put options against triple-levered ETFs that tracked the banking sector during the financial crisis.

These were ETFs that would swing anywhere between 10% and 30% on a daily basis, given what the Federal Reserve was doing with TARP or no TARP, Lehman going bankrupt, or Bear Stearns getting acquired by JPMorgan. I made a few hundred thousand bucks trading derivatives against those instruments over a few short windows. That was both a good thing and a bad thing for me.

The good thing was that it gave me a ton of confidence in myself, and I convinced myself that I was a genius. The bad thing was that it gave me way too much confidence in myself and convinced me that I was a genius. I decided that I wasn’t going to go to college and that I was going to start a hedge fund straight out of high school.

I got a Series 65 license, which is the license you need to start a hedge fund. There was a local financial adviser whom I spent some time with for a summer. He did private wealth management for some high-net-worth individuals, and some of those guys saw me trading on my screen and said, “If you start something, we’ll put $10,000, $15,000, or $20,000 into it.”

I ended up raising a fund in January 2009. I rolled my money into that fund, which was the largest check in the fund, and then I raised an additional $3 million from, call it, 45 individuals—lots of tiny checks that didn’t really mean a whole lot to anybody. I launched the fund in January 2009, so timing was definitely on my side.

The fund focused on concentrated positions in triple-levered ETFs, momentum trading on high-volatility tech stocks, and derivatives on those 2 strategies to get even more leverage on the first 2 strategies. I just had no idea what I was doing, but thankfully the market was forgiving of a strategy like that. There was extreme volatility along the way. I had certain months where I was down 37%, and one month I was down 51%.

August 2011 stands out as one of the worst months of my life because it was the European debt crisis, when Greece was on the crux of defaulting. I think the market had 13 consecutive down days, and I was short vol. I actually experienced how you could go into debt running a hedge fund. Thankfully, I recovered from that. It took a few months, but that was a very, very painful month.

I was in the Bay Area, and I just kept hearing more and more about tech. I didn’t particularly enjoy running a hedge fund. I did well financially relative to my age doing it, but I didn’t like sitting in front of a computer screen for 15 hours a day. It’s a very lonely job and a very stressful job.

I think people in venture complain that the feedback loops are too long. I agree that the feedback loops in hedge funds are too tight. I think you can convince yourself you’re a good investor or convince yourself you’re a bad investor too quickly in hedge funds. I think that’s why, if you look at hedge funds, by default they tend to have a shorter duration of life than a legacy private equity firm or legacy venture capital firm. It’s just very hard to outperform in public markets for extended periods of time.

But I was in the Bay Area, and I wanted to learn more about tech because it was my backyard. I kept reading about it, and I started cold-emailing VCs, angel investors, founders—just anybody I could read about online. Silicon Valley is a nice place. People are pretty receptive to cold emails, and I got a few meetings with individuals.

I learned more about tech and wanted to find a way to immerse myself in the ecosystem. I spent more time with individuals, but I wasn’t really getting anywhere. I thought, “If I want to do this for a living, I can’t be one foot in and one foot out. I need to just immerse myself in this entirely.” So I decided to wind down my hedge fund and focus on that.

The hedge fund did well. Everybody produced multiples on their investment. Then I tried to get a job at one of the big venture capital firms. I ultimately got a couple of interviews, and I look back on this and cringe.

One of the first guys who ever took a meeting with me was David Crane, whom I reconnected with recently. He runs Google Ventures. I shot him a cold email, and he responded. He was probably the most senior person who responded, and he asked me to come in for a meeting.

I wore a suit and tie and walked into the office. It was my first time walking into a venture capital firm, and I felt like a salesman. Everybody was wearing jeans, T-shirts, baseball caps, and sneakers. Based on the way I dressed, I knew I blew it in the initial meeting. But he was kind. He gave me some pointers and feedback, and I met a few other people as well.

The consistent feedback was, “Hey, listen. Your background is not that relevant to venture capital, but you should consider starting a company instead.” Over time, I’ve learned that there actually is no relevant background to venture capital. Similarly, there’s no relevant background to starting an art gallery, apparently.

Everybody suggested I should start a company, and I think that’s terrible advice to give anybody. You should never advise anybody to start a company. They should start it on their own or not start one at all. But I ended up taking that advice and started a company. I funneled everything I had left over from my hedge fund into that company.

This was in mid-2014, when marketplace lending was a popular sector.

Patrick O'Shaughnessy

Yeah.

Ramtin Naimi

Think companies like LendingClub and Prosper. I thought that sector was going to be the next big thing because, given the rate of capital going into it and the rate of exponential growth of those companies, I thought that if the sector reached its full potential, there would need to be a liquid secondary market for it because those loans did have maturity periods.

Those maturity periods scaled anywhere from 3 years to 5 years to 7 years. Banks trade debt like a liquid asset class all the time, so why wouldn’t the individuals trading on these platforms be able to have the same access to liquidity? I wanted to build an exchange that allowed debt investors to have that same level of liquidity.

I self-funded this company with everything I’d made previously, built out a team, and went through the regulatory framework for setting up an exchange.

Then, 14 months in, when I had a product, I was actually ready to raise external financing, but that sector had completely collapsed. I think Sequoia started writing Prosper down to zero, and LendingClub had plummeted like 85% from its peak IPO price. I had spent my entire net worth building a supplemental product to a collapsed industry. Pretty much everything I made on my hedge fund, I lost on that company, and I ended up in debt.

That was kind of my first reality check in life, when I realized, no, I’m actually not a genius, I could lose money, and maybe I should have just gone to college. Why did I put myself through all of this? One of the venture capital firms that I pitched that company to was a firm called Core Innovation Capital. The founding partner of that firm is a guy named Arjan Schütte, who’s one of the kindest people I’ve ever met in my life. He’s just a good guy.

Core’s focus is investing in fintech that provides upward mobility for the emerging middle class. It’s somewhat impact in nature, but very much focused on returns. When I wound down the company, I ended up reaching out to him, and he gave me a job. I ultimately got my venture capital job flat broke.

When I ended up in all this debt, I needed a way to restructure it. That was probably the worst moment of my life: sitting in the waiting room of a bankruptcy lawyer’s office, trying to figure out what type of bankruptcy I needed to file. It ended up being Chapter 13, which is not a write-off of debt but a restructuring for 5 years. Thankfully, things worked out, and I wiped it all off within 2 years. It was a nice comeback.

Patrick O'Shaughnessy

What was the headspace like at that time?

Ramtin Naimi

It’s awful. There’s nothing pleasant about that experience. In hindsight, losing your net worth is a lesson better learned at 24 years old than 54 years old, so I’m grateful for that. The learning there is, if you’re going to start a startup company, raise other people’s money instead of your own money.

But I remember once, when I was explaining this to institutional LPs in the early days, it was something I was very embarrassed about, and I was trying to figure out how to talk about it. Jerry Yang was one of my LPs who I spoke to about it, and he said, “No, I knew about it.” He said, “I loved it.”

I was like, “Why? Why did you love it?” He goes, “You should wear that as an entrepreneurial badge of honor. Any founder in the world with a failed company would have been in that same exact position had they put their own money up for a company.” He’s like, “That’s a true entrepreneur. That’s true entrepreneurship. You put everything you had into something because you believed in it. And when it didn’t work, you had to start from scratch.”

He’s like, “Venture capital is you put everything somebody else has into whatever you believe in. And if it doesn’t work out, then you get a job at Apple or Google, right?” That was actually a really interesting way to phrase it for me. Not that I don’t think there are various tiers of entrepreneurship, but the whole concept of wearing it as a badge of honor is like, yeah, you lost your own money on something that typically most people just lose other people’s money on.

Looking back on it, I’m like, that was cool. That was the epitome of my resilience journey, right? I got knocked as hard on my ass as I possibly could have, was humbled as much as somebody possibly could have been, and had to start completely from scratch once again.

Then I ended up with an entry-level job at a small venture capital firm. That’s where I met my partner today, Alex David. He was a partner at Core Innovation Capital. Within a few months of being at Core, it became pretty obvious to me that fintech Series A, impact-ish investing wasn’t what I wanted to spend my career doing.

Even though I have a ton of respect for Arjan and the mission that that firm is on, they’ve actually done phenomenally well with returns. They led the seed round of Ripple. I ultimately wanted to figure out how to become a generalist seed-stage investor.

The reason I focused on seed stage was because that was the only place where I thought I could access enough capital to the point where I mattered. Any later stage, there was no amount of capital that I thought I could access that would actually make me a relevant conversation in those places. So seed was the obvious starting point for me.

21. Building Abstract and Family Life

Then I needed to find a way to build a track record that didn’t involve working at a firm for a decade until I got serious check-writing ability, or raising my own fund, because who would give me a fund at that point in life? That’s when I learned about AngelList.

Patrick O'Shaughnessy

What’s behind the name Abstract?

Ramtin Naimi

Abstract. A couple of things. The definition of abstract is existing in concept but not reality, and that’s pretty synonymous with seed-stage companies. I also wanted the name to show up in places quickly.

I remember back then I spent all my days on Crunchbase, and Crunchbase had things alphabetically listed. I realized if my firm started with an A, it would be at the top of the list on everything. I wanted a firm that started with A, so that’s where I started.

Then I wanted a word that was easy to remember and didn’t sound like any other venture capital firm. I came up with the word Abstract. Then I found the definition for abstract, and I’m like, this actually just seems like a perfect name for a seed-stage venture capital firm.

Patrick O'Shaughnessy

If you were to describe the nature of whatever chip you have on your shoulder from, let’s say, your early to mid-20s through today, how has it changed, and how would you describe it?

Ramtin Naimi

I think the number one thing that’s changed is, in the early days, I just wanted to be accepted as an outsider. I think that’s happened because I actually think Silicon Valley is a very special place: if you prove that you’ve earned your seat at the table, no one actually cares about anything else. You’re at that seat for a reason, and we’ll leave it at that. So I think that is no longer a chip.

At any instance in the firm’s history, it was, “The early days were like, they don’t know what they’re doing. They’re just following other people.” I’m like, okay, cool. I’ll start leading deals. Then we started leading deals, and it’s like, “Okay, they only know what to do at seed. They have no idea what to do at later stage.”

They might be right. We’re still early and doing some early-side, later-stage things. But in any type of business, when there are other people who have a right to be there and they see you as someone who doesn’t have a right to be there, you’re going to get a lot of shade thrown your way.

I encourage my founders not to focus on competition. I try not to focus on competition. I just try to focus on doing what we can as best as we possibly can. I think everything we have done historically has proven that we can do what we think we can do, what we said we can do, and what we said we will do. I think we can continue that pace.

Patrick O'Shaughnessy

Say a couple of adjectives each about your parents. How would you describe them?

Ramtin Naimi

My mom is really tough, but also the most loving mom in the world. My dad is actually a totally soft-hearted guy, but very strict about having direction in life. My dad’s number one thing was, as long as you’re working hard, you’re good at something, and you know how to create something out of it, you’ll be successful at it.

My brother started a company as well, a vertical SaaS company that sells into the automotive industry, which, when we moved to the Bay Area, was the industry my dad got into. He ended up working at car dealerships and then working his way up until he eventually became a partner of a franchise group that primarily deals in luxury exotic cars.

My brother worked with him for a little bit and learned a little bit about that industry. He bootstrapped a vertical SaaS business that he just recently sold for a little less than $30 million. The cool thing about it was he went to Y Combinator and raised less than $600,000 for the company, and he just ran it with his co-founder and no employees. They got it to just shy of $6 million of ARR, but it was highly, highly profitable.

Besides 2 employees, some hosting fees, and some data licenses, there were no expenses to the business whatsoever. There are certain founders like him and other people in our portfolio that I point to as examples of how much you could actually do with just $600,000 or $1 million. But the reason I point to him is that we were raised the exact same way.

We think about things differently, but I think for 2 immigrant parents, having kids that have both built things—my brother sold the company for $30 million, and I have a venture capital firm that’s just shy of $2 billion in AUM today, with very humble beginnings—whatever they did instilled something in us. It instilled some sort of chip on our shoulder in us.

I think probably the smartest thing that they had done—and I don’t know if this is specific to Iranian immigrants or other types of immigrants—was that my mom was way more focused on us being in the best neighborhoods growing up versus the best house. She thought being exposed to what is possible was better than having a nice house or a big house in a place where you’re a big fish in a little pond.

She was the tiniest fish in the biggest pond in the neighborhood that we'd grown up in. I had friends whose fathers were the CEO of Visa or the CEO of Blue Shield and lived in these extravagant homes. So I knew these things existed, and I knew the path to that wasn't just being a doctor or lawyer; there were other things there.

I think the best thing that my parents did for me and my brother was exposing us to that.

Patrick O'Shaughnessy

What else outside of art and investing gets most of your attention?

Ramtin Naimi

I have a wife and 3 kids. My wife is pretty involved in my business, actually.

I met my wife at a holiday party. When I first met her, she was the director of marketing and communications at Bessemer. During our relationship, she became the head of marketing communications at Spark Capital, and now she freelances and keeps herself busy by making sure we don't screw those things up at Abstract.

She oversaw our entire rebrand, and she's very big on founder experience and the aesthetic of the brand and the firm that we built. I met her, I want to say, when I just turned 26 years old. So really, she was there in the founding days of Abstract.

What was really special about meeting somebody like her was that I love what I do, and I love talking about it. Because she worked in the industry herself for 6 or 7 years, she understands the significance of something that I might be excited about. She understands the significance of something that I might be upset about.

It's actually really interesting, and she appreciates what I do. She views it as a family business. She's very involved. She's outside the office, she's friends with everybody, and she's close with my partner. She actually cares about what I do, and she's always been my biggest cheerleader since day 1.

March 2020 came around, and we were engaged. We ended up having to postpone our wedding because every venue was closed for the next 2 years. We saw a lot of our friends traveling the world and really enjoying their COVID experience, and we basically decided whether we were going to do that or whether we were just going to start having kids.

So we did start having kids, and our first daughter, Lily, was born in October 2020. During COVID, we actually had 2 kids and raised 2 funds. We were very productive during COVID, and people say that if we were able to do all of that during COVID, we'll get through anything.

Basically, in 2 years, we lived in 1 house together and had 2 kids together, and I ran my business from the house for 2 years. It was a great experience, and honestly, we didn't even argue once throughout it. That's when it kind of became clear that it was just a meant-to-be relationship.

We ended up getting married in the backyard of our current home when we were pregnant with our second child. Now we have—we just had a third in December, who's now almost 6 months old.

Patrick O'Shaughnessy

Family, art, and investing.

Ramtin Naimi

Family, art, and investing. I have no time for anything else.

Patrick O'Shaughnessy

If you think about the entire process now of this little world you've constructed around yourself to have this incredible high-throughput, high-expansive frame of reference, to use your term, and all the things you're doing—30 pitch meetings a week—if you had to zone in on the single thing that gives you the most energy over and over again, what is it?

Ramtin Naimi

The companies that I decide to invest in when I decide to invest in them.

Patrick O'Shaughnessy

Like that moment?

Ramtin Naimi

That moment. You meet all these companies, and it's kind of like, “Okay, okay, hey, hey, this is cool. This is really interesting.” Then you start peeling back some layers, and you just get more and more excited about it.

Then you have to win. You pull out every single stop, you clear your calendar, and you do whatever you need to do to earn your slot on that founder's cap table and to earn their trust as their partner.

There have been windows of time where we went 2 or 3 months without investing in a single company. In those 3-month periods, I'm like, “What happened? I know there were good companies. Did we just not see any of them? Did we pass on ones that were obviously good?”

I kind of just feel like I had 3 months where I wasted time. We achieved nothing of value in the last 90 days. How do we prevent that from happening again? Are we not seeing enough companies?

I find a lot of excitement and enthusiasm. Outside of family-related things, obviously, watching my kids talk or speak or catch a ball or draw something—that trumps everything relating to business.

When a company you invested in really starts to work, that's always really exciting. When you see the stars start to align for one of your companies and you can be there to fuel the fire in any way you possibly can and be the pit crew to that Formula 1 driver, I think those things are really special.

The only part of this ecosystem I haven't asked about is the LP side. What have you learned matters to LPs? I guess a similar set of sensibilities around how you structure things to find, pick, and win the best LPs as well, and the sort of process that you run to do so.

We're very fortunate. We have an incredibly high-quality LP base that consists of blue-chip endowments and foundations, founders of generational companies, and either them directly or through their foundations as well. Great hospitals—just great organizations to make money for, candidly.

There are some other, more traditional, down-the-fairway guys who are good because they've done this for a very, very long time, and they're good mentors because they've been LPs in other funds for 20 to 30 years.

I think there are 2 types of LPs you meet—probably more than that, but I'll narrow it down into 2. There are the ones with imagination and the ones without imagination.

I don't want to throw shade at anyone in particular, but there are certain LPs who have built portfolios of amazing venture capital firms, and they had invested in them before they were amazing venture capital firms. They were fund-1 commitments to people who might not necessarily have checked all the boxes of a traditional venture capital firm.

I think, by and large, those people have done dramatically better than the LPs who may be less imaginative and tend to only back managers who've spun out from other platforms. That's the easy manager to back. It's, “Okay, cool. This person's been a venture capitalist for 10 years. You can look at their historical track record and pretty much underwrite what their future track record is going to be.”

Arguably, their future track record won't be as good as their historical track record because the deals they were able to access at those platform funds might not be deals that they have the ability to access or win in the future.

Paula Volent is a great example of this. I don't think she'd mind me using her name. She used to be at Bowdoin, and now she's at Rockefeller. She was a day-1 LP to Chase Coleman. I think she was very early to Josh Kushner, and she was my first institutional LP.

Bowdoin is a small endowment, but I actually think there are stories that show that it's one of the best-performing endowments in the world relative to its scale, and Stan Druckenmiller famously chairs their investment committee. Oftentimes, you'll see that the managers she's in are mega-managers today, but she was with them since day 1.

Like anything, there's a risk-reward profile. You take more risk with somebody when the reward potential is higher. If you take less risk with somebody, the risk is lower and the reward is lower.

You're looking for individuals, at least—especially if you have a more non-pedigreed background like I had—who are going to be more interested in manager-strategy fit versus, “What is your track record, and why should I care?”

In terms of what you need to do to make yourself appealing to LPs, there are multiple tiers of LPs. There's the highest tier of LP that can access any fund they want, and they're already in amazing venture capital firms. Then there are LPs that don't get into those deals and are looking for more exposure to other types of companies.

We fortunately have an LP base that is heavily concentrated in the best firms in the world, and then they added Abstract to their roster. That actually ended up being very beneficial for us because those are a lot of institutions that hadn't added a manager to their platform in a while. They already had the best managers, and getting Abstract added to that roster was kind of like a signal to the market: Pay attention to this fund.

I think what we brought to the table was something that they were already bought into. It was that these multistage platform brands will continue to dominate, and they're going to continue to get double-digit ownership in the best companies in the world early.

Their funds will get bigger and bigger, and as LPs, your exposure to those companies will be less and less, but you still will have exposure to the greatest companies. I think what we brought to the table was definitive proof that we're accessing the same quality of company—granted, less ownership, but dramatically more relative ownership.

When they look at our fund, if there are overlapping companies in our fund and any other fund they have in their portfolio, 94% of the time they have orders of magnitude more look-through ownership of that company through our fund than they would through one of the others.

Patrick O'Shaughnessy

What have we not talked about in the world of VC investing that you think is important and intrigues you? One thing I tend to talk about somewhat frequently, which I'm trying to figure out whether or not is a feature or a bug, is the scale of the companies that are staying private. It's kind of like a one-hand-feeds-the-other type of thing, because as these megafunds—and all of them—scale, they can only scale because—

Ramtin Naimi

The other ones are scaling.

Patrick O'Shaughnessy

Exactly. Right. So they can scale because the size of the companies that are staying private is scaling. If you have a $5 billion, $8 billion, $10 billion, or $12 billion venture capital firm, you need places where you can write $500 million to $1 billion checks. You now have that in a way that you didn't have 10 years ago, and you probably have about a dozen, maybe 15, places where you can write checks that large in venture capital today.

Those companies fan the flame that allows these VC funds to get larger and larger. They break the narrative that venture doesn't scale, because venture actually does scale if you can write billion-dollar checks into companies that are still growing. The companies in venture that are the largest are still outpacing the growth of any of their public-company comps, so they still do have venture-scale growth, but they're still private companies. The one thing that's interesting to think about from that perspective is what that actually means for an LP and what it means for early managers. I think it actually benefits us in a way that it might not benefit the later-stage guys.

But I think one unintended consequence of this is that it maintains hyperproductivity in these companies. I always joke—it’s an honest truth—that early liquidity was the bug and not the feature of crypto. People got rich too quickly, and they stopped building things. This latest swath of companies that can absorb $500 million to $1 billion checks—the reason the productivity of these companies is comparable to that of an early-stage startup is because there's been no early liquidity, and you have people still grinding and working. The liquidity is coming via these 1% to 5% tender offers, which is more than enough to give people a down payment on a house, but not enough to give people $40 million in cash and generational wealth.

Ramtin Naimi

The restrictions on secondary transactions have gotten really, really tight. So you can make an argument that excess liquidity early is a killer of productivity. Is there a way to throttle that? And, yeah, you keep your companies private and keep people satisfied with liquidity. I think that's very good from a company-building perspective. I think it's problematic from a venture-returns perspective. No LP is interested in getting liquidity in 3% to 5% installments, so I do think there needs to be a solution to that.

There's a seemingly new swath of continuation vehicles popping up in Silicon Valley, so it seems like there will be ways for people to get large sums of liquidity while venture managers get to maintain their basis and their position in these companies. I think it'll all net itself out, but I don't think the end result is ultimately that these companies are all just going to go public.

I think they've all found a hack, which is this: your top 100 performers today, if you give them all instant liquidity on their positions tomorrow, 92 of them probably might not be your top performers tomorrow, right? And if you want these companies to continue running circles around their public counterparts, I think this—I shouldn't call it trickle liquidity—but it's not like winning a lottery. It's not like if these companies go public.

I mean, what was the instance with Google? Something like over 100 people made over $10 million—

Patrick O'Shaughnessy

Something crazy.

Ramtin Naimi

And 92 of them were never heard of again, right? Then the other 8 ended up becoming VCs who wanted to make more money than that. So I think that's the risk you run into with that kind of liquidity. As people win these lotteries, and these companies are so large right now, that is the type of liquidity that the early hires and senior management of those companies will experience.

Patrick O'Shaughnessy

It's a really interesting way to think about it. I hadn't heard that specific angle on it before, but I'm glad I asked the question. I feel like we've covered a tremendous amount of information in 3 hours or whatever and gotten so much of your life. It's so interesting how all the pieces fit together and how your tendencies for approaching a new situation or problem sort of mirror each other. You've got this method that's clearly emerged.

Thank you so much for the time. When I do this, I ask the same traditional closing question of everybody: What is the kindest thing that anyone's ever done for you?

Ramtin Naimi

From a business standpoint? It was probably Arjan Schütte giving me that job at Core Innovation Capital. I actually look at that as the single point in my life that, had I not landed a job at a venture capital firm when I was flat broke with nothing to my name, where would I have ended up? There are a million scenarios I can point to where I wouldn't have ended up where I am today. So I could point to a lot of things that came from that guy giving me a job when no one else in the world would have at that point. That's probably the kindest thing someone's ever done for me in business.

The kindest thing anyone's ever done for me in my personal life is my wife just being the perfect wife. She truly is the embodiment of everything you need to succeed in life.

Patrick O'Shaughnessy

Thanks so much for your time.

Ramtin Naimi

Thank you.

How This VC Went From Broke to Becoming the Hot Hand in Silicon Valley | BidClub