Figma 上涨250%:史上最大IPO定价错配?Meta与Microsoft季度业绩大爆发:拆解
- Rory O'Driscoll认为,那些说“Figma把30亿美元留在桌上”的人是在胡说八道;Harry则说自己参加过5、6次定价会议:订单簿上的报价是38、39、40美元——没人报98美元,而“98美元这个价格之所以出现,只是因为IPO定在了38美元”。 投行设计出的正常涨幅是15-20%;偶尔会意外出现250%的涨幅——1999年以来最大的一次——而超大涨幅可能只是“IPO流程中周期性、自然发生的结果”,就像地震。直接上市也解决不了这个问题。
- 暴涨的真正代价是结构性的:机构买入前会设定内部卖出目标价,而“这些目标价没有一个会超过每股110美元”——因此,Figma现在的股价已经高于它主动争取的那些长线机构的目标价,Rory认为“他们中的大多数现在正在卖出这些股票”。 Brian Halligan对此反驳:长线机构只是先建立小仓位并长期持有;“我认为卖出的是对冲基金。”
- IPO窗口大幅敞开,便宜资金已经转向公开市场。 Rory的框架是:过去3年,私募资本更便宜、麻烦更少;现在公开市场的估值倍数已经高于私募市场,所以“如果你未来2年需要融资,现在会是一个非常他妈好的时点”。Lemkin对Canva的建议是:“快跑,Forest,快跑。”Halligan也认可一条与会者的判断:“VC比公开市场投资者难缠得多。”
- Halligan认为,CEO薪酬已经双重失灵:2006年监管变化后,行业从ISOs转向RSUs,这“让CEO变得风险厌恶”,而不是像ISOs那样放手一搏;按同业分位数对标,会给Dylan Field约2000万美元——“只相当于他净资产的3%……根本改变不了什么”。他认可Figma约20亿美元的PSU豪赌;Rory指出其中的陷阱——最高约118美元/股的价格触发条件,靠暴涨本身就已经实现,因此“业绩成分很快就消失了”。如今,豪赌式激励已经成为许多增长轮条款清单的标配。
- 关于AI资本开支,Rory在财报周得到的结论是:这不是AI正在创造效益,而是超大规模云厂商原有业务产生了巨额现金,只要这些业务继续产现,它们就能持续为基础设施建设买单。“真正的男人手里有700亿美元自由现金流,就能拿出400亿美元去买服务器。”账面上,每年4000亿-6000亿美元资本开支,可能只对应250亿-300亿美元应用收入——长期趋势确实真实,但“边际玩家会像2001年一样被淘汰”。Brian判断泡沫的信号是:科技公司卖给科技公司;他更关注“普通人”收入,也就是ChatGPT、Harvey和Rogo。
- SMB AI仍是尚未攻克的机会:专业消费者产品有效(Lovable、Gamma),企业产品也有效,“但中间这一层我还没看到太多”。障碍在于训练——“Brian和Jason的三明治店里,没有AI团队”。Jason Lemkin表示,任何能解决自训练问题、把一次“Palantir级别的部署”从6个月压缩到60秒的创始人,“我现在、此刻就想投。”
- Cognition/Windsurf据传以150亿美元估值成交,高于此前传闻的100亿美元,基于合计约1.7亿美元收入;它买的是品牌和市场入口,不是团队——30%员工被裁,其余人要么接受每周80小时的工作量,要么拿9个月补偿离开。 Lemkin从这场交易中得到的教训是:一旦离开标准资本结构,“你基本上就只能依赖陌生人的善意……而这永远是个错误”。与此同时,Ramp以220亿美元估值融资5亿美元,部分只是金融科技的物理规律——“稀释2%,还是拿银行牌照,二选一”;高价融资只有在你还必须再次融资时,才算“自杀轮”。
1. IPO价格由精疲力竭的创始人在发行前夜、与自己的投行隔桌决定
- Halligan回忆,价格和配售在发行前夜敲定。此前连续2周跑了12个国家、每天路演6场,“你的电量已经见底”。整个路演期间,公司和Morgan Stanley“完全站在同一边”,直到最后这场1小时的会议,双方突然“隔着桌子对坐”:投行拿来的订单簿塞满了“他们的对冲基金哥们”,而且给了相当不错的配额;公司想要的却是长线机构——Fidelity、Wellington、Capital、T. Rowe。
- 接下来就是Harry在5、6个定价会议里都听过、每次几乎一字不差的说辞:Morgan Stanley推动HubSpot以24美元定价,因为“Fidelity告诉我们,他们24美元会买,25美元就退出”。HubSpot和Fidelity玩起胆量游戏,最终定价25美元,但Fidelity还是买了。Brian谨慎地说:“我不认为存在串通,但Morgan Stanley和Fidelity显然站在同一边,都在试图让我们以更低的价格出售。”
- 至于暴涨应该怪谁,答案是:“创始人决定价格是多少。所以是Dylan做的决定。”而Figma的发行条件本身就极易引爆行情——以老股出售为主、发行新股极少、超额认购40倍(HubSpot为27倍),6家大型长线机构因为拿不到大额配售而“非常恼火”。Halligan为团队辩护:“Figma没有蠢人……没有人把这笔交易定价定得离谱地低。”
- Harry对上市收盘晚宴的比喻,值得这张入场券的票价:“投行刚刚为了每股1美元坑了你一把,作为补偿,他们请你吃一顿昂贵的饭,再灌醉你,让你忘掉这件事……第二天你开车离城,下一只羔羊被送进屠宰场。”这种机制为何从未改革?“这件事你一辈子只做1次,也是你人生中最重要的事;而这些人每天都在做。”
2. “98美元这个价格之所以出现,只是因为IPO定在了38美元”——30亿美元的批评经不起订单簿检验
- Harry把两个问题分开:一个是刻意设计的“小爆炸”——经典的15-20%涨幅,让Fidelity感觉良好;另一个是意外出现的大爆炸——Figma约250%的涨幅,他称之为1999年以来最大的一次。前者是每股1美元的争论,后者完全是另一种现象。
- Rory彻底拆解了Gurley式批评:订单簿里的报价是38、39、40美元,“没人以98美元下单”。因此,“如果有人走进来,说我知道这只IPO明天开盘会到100美元,那我们就以80美元融资——他们根本不会有订单簿”。那30亿美元“根本拿不到”;声称可以拿到的人“是在胡说八道”。Figma或许少拿了“几美元”,但不是60美元。
- Rory认为,真正令人难过的后果是:每家大型机构买入时,都会设定一个内部卖出目标价,而“这些目标价没有一个会超过每股110美元”。于是,股票现在已经高于你最想要的那些长线持有者的长期目标价,“他们中的大多数现在正在卖出这些股票”。Halligan不同意这个事实判断:长线机构是先建立小仓位,“准备长期持有……我认为卖出的是对冲基金”。
- 还有两个经常被忽略的利益相关方。一位与会者曾在自己第一家创业公司的IPO中负责定向配售项目:员工凑出5万-7万美元买入,“公司里基本上每个人当天都赚了10万美元……员工甚至不知道稀释是什么”。至于创始人稀释,Halligan只用了4个词:“我的净资产从X变成了100倍。我当时只觉得能参与其中就很开心。”Rory认为,这正是“这个流程如此难以改变”的原因。
3. 资本结构质量会复利10年——Zendesk的警示故事
- IPO前,HubSpot做了一轮非交易路演:所有线下见到的大型投资者都大举买入;唯独错过的两家——巴尔的摩的T. Rowe和南加州的Capital Group——在IPO后花了3-4年才争取过来。Rory的规则是:“你永远记得那些没拿到的人。”
- 反事实案例是Zendesk:它在市场动荡的一周、比HubSpot早3个月定价上市,始终没能真正争取到大型长线机构,因此多年保持着对冲基金占比较高的股东结构。问题出现后,这个较弱的股东基础在边际上助推了激进投资者施压,也促成了不情愿的出售——公司拒绝了约200亿美元的报价,最终以约100亿美元卖出。Halligan坦率地总结:“拥有一张好的资本结构表被低估了”,而HubSpot能拥有好的股东结构,“更多是运气,不是能力”。
- 直接上市能救Figma吗?Rory做了功课:SEC现在允许公司通过直接上市融资,Amplitude就是案例;但直接上市的清算价会是39或40美元,而不是100美元:“超大涨幅是IPO流程中周期性、自然发生的结果”,就像地震。他现在观察到风险投资市场也有类似规律:一个品牌名以120美元定价一轮,6周后“又有一群人以350美元做同样的事”。为什么?因为品牌名在里面。这是公开市场版本的他所谓“formal”。
- 顺带击穿一个散户迷思:HubSpot约90%由大型机构持有,“散户持有的非常少……由普通家庭持有,其中包括Harry Stebbings的妈妈”。
4. 快跑,Forest,快跑:便宜资金已经转向公开市场
- 被问到Canva看到这种行情应该怎么办,Lemkin毫不犹豫:“快跑,Forest,快跑。市场大开,估值不错……我会把所有事情都安排好,准备上市。”但Lemkin也补充说,创始人已经质押了大部分股票,公司已经盈利,早期投资者也曾在数百亿美元估值上交易——“这显然不是一个正在打造中的Musk帝国。”
- Rory把镜头拉回机制本身:“价格会让所有市场出清。”过去3年,私募资金更便宜、更容易拿到——“5倍收入,还得面对一群在纽约对我百般刁难的人;10倍收入,却不用和这些增长期投资人见面,一年只见一次。”现在情况反过来了:“便宜资金已经在公开市场……如果你未来2年需要融资,现在会是一个非常他妈好的时点。”
- 面对Stripe主导的“为什么还要上市”论调,Halligan用亲身经历做比较:在私募市场,“我们被一群古怪、略微错位的VC投资者缠着,他们肯定已经钻进了我们的短裤”;到了公开市场,还是同一类人,但“没那么钻我们的短裤”。公开市场投资者“被低估了”,只要保守地描绘长期图景,他们是理性的。Twilio和Zendesk遭遇激进投资者的恐怖故事“相当罕见”,而且这些公司“确实遇到了一些问题”。Halligan认可的字幕金句是:“VC比公开市场投资者难缠得多。”
- 从人的角度看,IPO日是“你人生中最重要的2、3天之一。你会哭,会笑,会拥抱”。Halligan回忆,一位联合创始人曾在公司市值达到10亿美元时给他看股票应用:“截个图。我们以后再也看不到这个数字了。”(实操层面:第一笔交易需要数小时才能结算,Figma花了约6小时;选NYSE而不是NASDAQ,因为“你可以敲钟”。)
5. CEO薪酬已经失灵——应该锚定净资产,而不是同业
- Halligan从两方面批评现行机制:2006年监管变化后,行业从ISOs转向RSUs,这“让CEO变得风险厌恶”;期权则会让你“放手一搏”。薪酬委员会如果按同业第75百分位定薪,会给Dylan Field每年约2000万美元——“这相当于他个人净资产的3%,根本改变不了什么”。逻辑和Musk一样:“Mary Barra年薪2900万美元。你觉得Elon会在乎2900万美元吗?”因此,他认可Figma以PSU为主、规模约20亿美元的豪赌。
- Harry分析说,PSU“奇怪地重新创造了2006年被监管取消的期权”。但Figma这套方案“没有奏效”,因为股价触发条件一路上探至约118美元/股,却被暴涨本身直接实现了。“业绩成分很快就消失了”,尽管Dylan仍会在7年内逐步归属。他更喜欢收入、营业利润等可触摸的多年目标,但披露要求以及“ISS和那些爱抱怨的人”,会把所有人重新推回股价触发条件;2018年的每套方案都因此兑现,而2021年这一批方案(包括Airbnb的)则被困住。
- HubSpot的答案是“新增ARR加一个最低盈利数字”,这让Rory由衷赞赏:“很少有薪酬委员会像Brian这样做……这比只盯着股价好太多了。”Halligan对所有薪酬设计的概括是:“没有什么是完美的——只能看你能做的最不坏方案是什么。”
- 趋势正在扩散:Lemkin看到自己投资组合里的“每一轮增长融资”都出现豪赌式薪酬方案——按10亿美元估值成交,但如果做到10倍,创始人还要分享公司额外7-10%的股份。Rory预测,那些业务做成了、却没达到膨胀后的股价触发条件的CEO会要求豁免,“我现在已经能想象那部电影了”;Lemkin则押注,脾气糟糕的VC不会让步——“现在已经不是2024年了”。相关地,Halligan认可创始人二次出售:当年以约200万美元卖给Sequoia,事后看是“糟糕的财务决定”,但Salesforce找上门时,“它让我更有底气”;现在他每月出售完全相同数量的股票,让市场看不出任何信号。
6. Meta的季度业绩与资本开支问题:现金机器正在为前沿建设买单
- Harry给出的数字是:调整后EPS同比增长38%,收入增长22%,自由现金流下降22%。Rory在财报周最大的顿悟是——此前他“大致看对了AWS,却大致看错了Microsoft”——这不是超大规模云厂商的AI在创造效益,而是“它们所有原有业务都运行得太好、产生了太多现金,因此未来1年还能继续这么做”。正如他所说:“真正的男人手里有700亿美元自由现金流,就能拿出400亿美元去买服务器。这是一个伟大的国家。”
- 他的泡沫算术是:AI应用总收入可能只有250亿-300亿美元,对应每年4000亿-6000亿美元资本开支。假设10年后应用收入达到3000亿-4000亿美元,长期趋势“几乎肯定是真实的”;但中间会有一段时期,“边际玩家会像2001年的边际玩家一样被淘汰”,杠杆过高的公司会被烧毁,大公司则会先收缩、再逐渐消化这些产能。他拒绝两种极端:“这既不是惊人的AI极端主义,也不是泡沫末日论……在发现前沿之前,你永远投得不够;除非你尝试,否则最后只会变成欧洲。”
- 一位与会者判断泡沫的信号是:“科技公司卖给科技公司,会让我紧张。”1999-2000年就是这样,Harry补充说2021-22年也一样。他想看到的是“普通人”收入:ChatGPT,向律师销售的Harvey,以及面向投资银行家的Rogo。Lemkin不让这个讨论轻松过关:“它在某种程度上必须是泡沫。资本开支不可能永远持续……希望我们都能及时离场。”
- Halligan指出一个被忽略的赢家数据:从2022年8月26日市场触底以来,Oracle和SAP股价都上涨约230%;在SaaS公司中,只有Shopify约300%的涨幅更高,超过了HubSpot、Salesforce、Adobe和Atlassian。Rory尤其看好Oracle:它拿现金流买了GPU,“现在已经让自己重新成为云市场的重要参与者”。
7. 年度CEO是Jensen,但Satya的案例更有意思
- Rory毫不犹豫地选Jensen,一位与会者补充理由:“他正在重新思考CEO这套打法。”另一位与会者从结构上解释:此前没有大规模存在的两类基础设施——GPU和模型——分别掌握在Jensen以及Sam/Dario手中,而且两者现在“相对于各自类别的其他部分,似乎都占据主导地位”。Satya和Zuck争夺的是另一种奖项:“在超大规模上出色管理现金机器——事实证明,这是度过成年生活的一种相当赚钱的方式。”
- 一位曾在Adobe担任VP的与会者,提出了支持Satya而非Zuck的理由:对创始人来说,“这东西很容易——把部队召集起来就行。Zuck想做什么都可以。”Adobe花了3年内部说服,才完成向云端迁移;Satya则邀请Sam Altman进来,做出“买下OpenAI 49%的这个古怪交易”,并在没有创始人权威的情况下,全押Azure做AI。另一位与会者给他的定义是:“他基本上是一个重新创业的创始人。”
- 另一种更阴暗、也更有趣的解读是:Satya的天才之处在于,他接受了“这家庞大的官僚公司自己做不成”的事实,于是选择把复杂的交易谈下来,而不是继续撞墙。他脑海里的声音大概是:“真他妈谢谢你们所有人,我只能带着一个BD人员把这件事想出来,而你们所有人都坐在那里混日子、不交付AI。”没错,Microsoft要承担OpenAI 49%的亏损;但这只相当于营业利润的约3%,换来的可能是1万亿美元。
8. SMB曾是HubSpot的逆共识,SMB AI仍未被攻克
- Halligan最初押注SMB,是因为他整个职业生涯都在经历“向CIO销售那种摧毁灵魂的过程”,相信互联网会不成比例地偏向小企业——“你的成功更多取决于大脑的宽度,而不是钱包的厚度”——并且用CAC和LTV,而不是利润表来判断业务。这在当时极度逆共识:更偏企业市场的Marketo才是共识选择,融资估值也更高;而SMB赢家——Shopify,“甚至比HubSpot更好”、Block、Monday——都来自“硅谷共识之外”。
- 这个起源故事也说明了周期规律:2009年经济衰退期间,HubSpot在Sand Hill上下见了20家投资者,“每个家喻户晓的名字都说不”,直到Scale为一家收入700万-1000万美元、正以100%速度翻倍的公司开出投前6600万美元的条款清单。Rory说:“大家都不买的时候,才是买入时机。”2009年的窗口孕育了HubSpot、Box、DocuSign和RingCentral。
- 今天在AI领域,SMB打法还能奏效吗?Lemkin的困惑是,真正的AI产品需要训练和前置部署工程师,而SMB两者都没有。HubSpot自己声称80%的“SMB”拥有AI团队,但这与他的判断冲突:“Brian和Jason的三明治店里,没有AI团队。”他愿意立即开支票:任何能解决自训练问题、把“Palantir级别的部署”从6个月压缩到60秒的创始人,“我现在、此刻就想投”。Rory看到的是一个杠铃:专业消费者产品有效(Lovable、Gamma、Replit),企业产品有效,“但中间这一层我还没看到太多”。
- Rory的答案是,这“可能还要再花1、2年”:有钱可烧的大公司会先定义应用类别,然后SMB获得“预训练、预配置”的产品——接听电话、派发订单——“打开就能用,你们两个人听起来就像一个大型呼叫中心”。SMB想要大公司拥有的一切,但必须“打包得足够紧、定价得足够紧……切成一口大小”。Halligan也提醒,不能把HubSpot的历史模式照搬过来:当年很多有效的东西——入站营销、免费增值、PLG——“今天根本不会奏效。你必须持续创新”。
9. Cognition/Windsurf:买的是品牌,不是团队——结果所有人都是灰帽子
- 这轮传闻中的估值从100亿美元升至150亿美元,对应合计约1.7亿美元收入(双方各约8500万美元)。Lemkin对估值跳升并不意外,这和Anthropic传闻估值从1000亿美元升至1700亿美元的逻辑相似:“市场对优质资产的需求很高……价格就是稀缺资产的分配机制。”这其实是私募市场版本的IPO暴涨。
- 交易完成后的安排说明了这笔交易究竟买了什么:Cognition裁掉被收购Windsurf团队的30%,并给剩余约200人选择——每周工作80小时、每周6天到办公室,或者拿9个月补偿离开,须在8月10日前决定。Lemkin的判断是:“很明显,他们买的不是团队。”Devin是一款受尊敬的细分产品,他最难的问题组合型CEO会使用它,“但他们不会像使用Claude Code那样,把它部署给整个团队”。因此,Cognition买到的是一个品牌、约8000万美元需要维持的收入,以及3-9个月的加速市场进入期;按新估值计算,基本不需要额外稀释。
- 在交易内幕曝光后,大家才知道Windsurf剩余的1亿美元并不是Google出资,而是创始人和投资者筹出的。这场风波的道德是:“白帽子没有看起来那么多,结果所有人都是灰帽子。”Lemkin进一步总结:一旦离开标准资本结构,转向临时拼凑的交易安排,“你基本上就只能依赖陌生人的善意——正如Blanche DuBois所说,而这永远是个错误”;在正常的特拉华州并购里,至少“你最终拿到的就是你该拿到的东西”。
10. Ramp的220亿美元估值、自杀轮迷思,以及CRV退回自己最擅长的事情
- Ramp以220亿美元估值完成5亿美元E轮融资,由Iconiq领投;这大约是它18个月内的第5或第6轮融资。Lemkin认为,这既是增长势头,也是实际需求:发行公司卡意味着要为资金沉淀提供资本。一位与会者粗算,约700亿美元收入背后的交易量,如果对应2%-2.5%的 interchange 收入,就意味着30亿-40亿美元的资本需求——“你正在取代Amex”。所以结论很直接:“风险投资股权是市场上成本最低的资本。稀释2%,还是拿银行牌照,二选一。我会选择稀释2%。”
- 针对Harry提出的“自杀轮”问题,例如以31亿美元估值融资1亿美元,规则是:过高的价格“只有在你必须再次融资时,才叫自杀”。如果你以20亿美元、甚至40亿美元估值融资5亿美元,3、4年后以15亿美元上市——“给那些按20亿美元估值买入的人添堵,但生活还得继续”。真正致命的是,你需要融资4亿美元,却只融了1亿美元,最后又在下行轮里回来。Lemkin补充说,这种1%-2%的估值上涨本身几乎没人注意;他自己的一个小型LP曾告诉他,区区30亿美元的估值上调“根本不算数,不要确认它”。
- CRV募资7.5亿美元、缩减团队并放弃后期精选基金,得到的是赞赏而不是担忧。一位与会者说:“把你擅长的事情做好……保持信息清晰。”而LP的偏好并非非此即彼:同一个LP可以支持CRV聚焦,可以再给Founders Fund10亿美元,也可以单独给Elad Gil15亿美元。Lemkin根据自己的机会基金计算,可能只是“多拿10%-15%的carry,却换来大量戏剧性”,“我90%的carry会来自主基金”;而且2只7.5亿美元的基金优于1只15亿美元的基金,因为“你想更快进入carry阶段”。
- Harry追问Benchmark:基金规模纪律是否让它错过了Miles和Victor?一位与会者拒绝接受个人化叙事,把问题重新定义为:最好的专业基金,能否与全栈机构竞争?Benchmark“即便不是最好的,也是最好的专业基金之一”;两种策略都可以成功,前提是执行到位,但各自都有风险——专业基金会被“噪音挤到一边”,全栈机构则会扩张到“很多单笔看起来不错的交易”,却拼不出有吸引力的整体回报。一位与会者给出的市场判断更直白:在X的讨论中,品牌名单就是“YC、Sequoia、Andreessen——基本就这些”。
Rory O’Driscoll
The people who said, “Oh, Figma left $3 billion on the table.” The $98 price only happened because the IPO happened at $38. The discussion they were having on the day was, let’s call it the Halligan discussion, of, “Do I go $2 more and exclude Fidelity, or $2 less and take Fidelity?” It’s a good, useful discussion. Had someone walked in and said, “I know this IPO is going to price at $100 a share to open tomorrow morning. Let’s raise at $80,” they wouldn’t have had a book, because no one had bid at that thing. So, that money wasn’t accessible.
Jason Lemkin
Run, Forrest, run. The market’s wide open. The valuations are good. There’s a lot of demand. It’s very seasonal. Timing really matters.
If I were Canva—it’s an amazing company—I’d be lining everything up to go public.
1. The Worst IPO Mis-Pricing Ever: What Really Happened at Figma
We’re just going to start and dive in with the Figma IPO. We saw the most unbelievable mispricing. It went out at $33. It went up to around $145. I’d like to throw this out there to some of the greatest minds in this business: How did we analyze this unbelievable pop? What was it at HubSpot, Brian? There must have been a pop, right?
Brian Halligan
We had a pop.
You priced at $25 and you opened around $30.
Brian Halligan
We priced at $25. I think we opened at $33.
Yeah.
Brian Halligan
It might be worth just talking about what happens behind the scenes on this.
Yeah, everyone’s talking out of their rears on X, aren’t they? They act like they know everything.
Brian Halligan
Yes. I don’t know everything, but I can share what actually happens and how you make that decision and what the pressures are. First of all, you’re making the decision on the price and who the investors are the night before the IPO. At this stage, you have never been as tired in your entire life as you are when you’re making this decision.
You’ve been on the road for the last 2 weeks. You hit 12 countries. You had 6 pitches a day. Your battery is on red. You’re tired, and then the investment bankers sit you down and say, “You’ve got 2 big decisions to make.” One is who the investors are going to be—who are we picking? We were 27x oversubscribed. Figma was 40x oversubscribed. Who are they going to be? Then, what’s the price?
For the whole process, the founders were very well aligned with Morgan Stanley and the investors—perfectly well aligned—until this 1-hour meeting the night before the pricing. All of a sudden, you realize, “Actually, we’re across the table from you.”
The first thing you’re across the table from is they give you the book of all the people who want to buy your stock. Again, 27x more demand than you have supply. In their version of the book, they have a lot of their hedge fund buddies in there with pretty good allocations. We also have some of the quote-unquote long-onlys. We could talk about that, too: Fidelity, T. Rowe Price, Wellington and Capital Group.
What HubSpot wants is just the long-onlys. You want to keep the hedge funds out. Morgan Stanley wants that, too. They want to keep them happy, but they also want their hedge fund buddies in there because they make a lot of money on that. So, that’s a negotiation, trying to get all that—squish the hedge funds down and get the long-onlys up.
Then it’s the price. In HubSpot’s case, it was a very interesting dynamic. We had raised the range throughout the roadshow over the previous 2 weeks. Morgan Stanley—we wanted to go out at $25. Morgan Stanley said we should go out at $24. The reason we had $24 was that Fidelity had told us that they were in at $24 and out at $25.
You really want Fidelity because Fidelity has trillions of dollars, and they could own—you know, they could be a massive buyer. So, then you have a debate in your head: How badly do you want Fidelity? How much do you want to sell for?
We were oversubscribed, and we thought, “I think Fidelity is going to come in anyway. It’s a really good thing. I think they’ll come in. We’re going to stick with $25.” So, we pushed back. We said no, and we priced it at $25. I don’t think there was collusion going on, but definitely Morgan Stanley and Fidelity were on the same side of the table, trying to get us to sell at a lower price. That’s kind of how it happened behind the scenes.
So, there are these micro-conflicts, but they rear their heads at the last minute in particular, right? At the last minute.
Brian Halligan
It’s really just the very last minute. It’s fine, and by the way, there’s a lot of talk around the pricing and how much it pops. Whose fault is it? Morgan Stanley’s fault? The founders make the decision on what the price is, so Dylan decided at the end of the day.
By the way, if you’re Dylan and you’re at Figma, you had a very limited amount of shares that were selling. They were mostly secondary. There were just very few shares to sell and a lot of demand for it. If you’re Dylan, that’s going to drive the price up.
The second thing is, here’s who you really want: You want Fidelity, you want T. Rowe Price, you want Wellington, you want Capital Group. There are about 6 big long-only funds you want in there. They’re pissed because they’re not getting a big allocation. That created the demand environment that was a little tricky for them because they wanted to buy more shares, and that’s what pushes the price way up.
The supply is low and the demand is very high. It’s an interesting little game of chicken. You played chicken with your investment bankers and some of the long-onlys right at, like, 7:00 the night before the IPO.
But there’s no one dumb at Figma. This is the other thing about social media. You think Dylan and his whole finance team and CFO have never heard of these issues before? I mean, everyone’s trying to weigh everything and come out with the optimal outcome, right? No one massively mistakenly underpriced this deal, did they? We’re not talking about rookies here, are we?
Brian Halligan
I don’t think so. I think there are a lot of smart people around the table giving them advice, and they wanted to make their investors happy. Part of it also is you want to have a pop. You want Fidelity, T. Rowe Price and these long-only folks to come in and, right out of the gate, feel good about their investment. You want them to hold for decades and decades and decades. So, there’s a little bit of that. It probably just popped more than he thought.
And that’s the actual sentence, right? Until that, Brian, everything Brian said is correct. The stunning thing is they clearly give the same speech every time, because I’ve been in the room, I think, 5 or 6 times, and they give it. It’s always Fidelity and one of the other 2. It’s like, “You want Fidelity. It’s only another dollar,” right? That whole speech is exactly right, and you want a little pop.
The interesting thing that Brian said at the end was the odd thing here is, instead of getting, let’s call it, the designed 15–20% pop that makes everyone feel good, you ended up with this absurd 250% pop, which is clearly off the charts. I think it’s the largest pop since 1999.
What you’re really saying is you’re trying to engineer this small explosion, and then every once in a while, inadvertently, you create a big explosion and you look like an idiot. So, the question is, are we arguing about whether we need small explosions, which happen all the time—in other words, the classic HubSpot 20% pop? Is that a problem or not? That’s all about a $1 discussion with Fidelity.
Then there’s the separate problem of when you get it massively wrong. What causes that? They’re 2—I think you should talk about them separately, because they’re almost 2 separate issues. Does that make sense?
Brian Halligan
Because there’s 1 small thing I heard nobody talk about on X. At my first startup job, they gave me the job—and this is the only IPO I’ll ever have been through as an employee—of handling the directed shares program. It was my job to hand them only to the employees, not the external ones.
There was a lot of drama because people had to come up with $50,000, $60,000 or $70,000 to buy their stock. This is a lot for folks who had no secondaries. There was no secondary, and everyone in the company basically made $100,000 that day. It was a magical thing.
Now, was it underpriced? But we forget about the employees. They don’t care about that. They don’t even know what dilution is.
Yeah.
Brian Halligan
All they care about is what happens with their stock. It was a magical moment for the employees. Whether it was mispriced is a different issue, but no one’s talked about that transfer. It may be a small issue, but employees may not care.
I guess a core question for me is: Do we think it was fundamentally mispriced, extensively, or is this actually just IPO exuberance on an asset that is good, with a great-quality founder? Is it not dramatically overpriced at the $137 that it hit?
Rory O’Driscoll
Agreed. That’s actually the next truth. You’re exactly right, because the whole 20% pop discussion is an interesting one. Maybe Fidelity, to use Brian’s example, would have bought at $24 or $25, and they probably bought more at $30, right? That’s kind of in the bounded range.
I can tell you right now, the people who said, “Oh, Figma left $3 billion on the table because they could have got $95 a share,” are talking out of their ass. I can guarantee you the order book—I think it was, what did the price say, at $35, $38, whatever it was—there was some at $38, there was some at $39, there was some at $40. No one was putting in an order at $98.
What happened—and this is kind of a bit existential, metaphysical; maybe go with it—is that the $98 price only happened because the IPO happened at $38. It’s exactly what you said, Harry. The discussion they were having on the day was, let’s call it the Halligan discussion, of, “Do I go $2 more and exclude Fidelity, or $2 less and take Fidelity?” It’s a good, useful discussion.
Had someone walked in and said, “I know this IPO is going to price at $100 a share to open tomorrow morning. Let’s raise at $80,” they wouldn’t have had a book, because no one had bid at that thing. So, that money wasn’t accessible. All that happened here was, as you say, I think maybe they could have got a couple of extra bucks, and maybe that might have slightly dampened demand, but really what you’re saying, Harry, is correct.
Rory O'Driscoll
There was some pent-up euphoria on the retail side, and they all rushed in. I can tell you why it's not successful. Going back to Brian's example—and this is a really sad comment, but it's true—if you have a 20% pop and you get Fidelity at $25, they'll buy more at $32.
Let me give you a really sad fact, and I didn't realize this at first. All those big buyers who came in at Figma at $38, before they buy, they have an internal process with a price target to exit. None of those price targets are going to be more than $110 a share.
So, unfortunately, because you want to price it—I won't say underprice it—it's now trading at a price that's probably above the long-term price target of the long-term investors you want. Most of them are selling those shares right now. I used to think, “Oh my God, they'll hold because they know it's a long-term investment.”
But if you're running money as one of these institutions and you bought at $35 and built a business case that says, “We think this will be worth $50 a share in 2 years,” and suddenly it's worth $100 a share in 2 days, at least half those mutual funds have to say, “Should we lose our position?” My guess is they will.
Brian Halligan
People say long-only. They're not long-only. They do sell. They come in and out of HubSpot. I see them coming in. I think they're trying to build a position. They only floated a tiny amount here, and so I think they're like, “Okay, we're in there. We got a toehold. We're going to hold for the long haul. We think this is substantial.”
I doubt they sold. I think it's Harry Stebbings that sold. I think it's hedge funds that sold.
Jason Lemkin
I think they're definitely right on the hedge funds. No one in the hedge fund world is out; it's in.
Brian Halligan
Yeah, I doubt the big long-only—quote-unquote, long-onlys—sold. Can I tell you guys another story about this whole thing?
First of all, on this topic, before HubSpot went public, we did something called a non-deal roadshow with Morgan Stanley. We met all the big investors. All of the big investors we met came in big on our IPO.
The ones we missed, we couldn't convince to come in on the IPO. For us, we missed T. Rowe Price. It's down in Baltimore. We didn't want to go down to Baltimore. And we missed Capital Group in Southern California. It just didn't quite hit. It was a long trip, and we missed both of those in the IPO.
It took a good 3 or 4 years before we got T. Rowe Price and Capital Group in and convinced them this was a good company that was going to be around for the long haul. So you kind of want those guys in there, and you want to make it a strong incentive to get them in right off the bat, or you might not get them for a while.
And meet them in person.
Brian Halligan
Yeah. So the non-deal roadshow is key.
Jason Lemkin
It's also proof of the old rule: You always remember the people you didn't get, no matter how long ago. All of us have been fundraising. You can vividly remember every no. You can vividly remember every, “I didn't go and see them, and I should have.”
Do you think we overestimate the importance of having Fidelity in the IPO?
Brian Halligan
I think it's important. Fidelity and T. Rowe Price own a huge chunk of HubSpot now. Wellington Management owns a very large chunk of HubSpot, and they're pretty stable. They trim on the edges and come in and out.
Most people think consumers own a lot of the stock. The retail investors own a lot of the stock. Very little of HubSpot is owned by mom-and-pop investors. It's like 90% big institutional investors.
Brian, you never gave me access to the IPO. I would have been—
Brian Halligan
For the record, Harry, I think you were 12 at the time. I'm not even sure you could legally own stock, big guy.
Dude, there's no way I could have bought. I was totally underage. The one thing that I do think is, if we're Dylan Field now at Figma, are we thinking, “You know what? I wish I'd done a direct listing”? Does this make direct listings much more attractive, and would this have solved the problems that we've seen?
Rory O'Driscoll
Again, I'm going to push, because when you sent out the questions, I did more reading on this than I had in a while. One thing I didn't realize is the SEC has amended the rule, so you can now raise capital on a direct listing. So it is possible, right? I think Amplitude did it.
But—and this is the big but—if you did a direct listing, and this is why I said it gets kind of weird, I don't think you would have direct-listed at $100 a share. It might have been $39 or $40, right?
The weird kind of thing is, I've just—how do you put it?—come to think that it may well be that these random, weird pops every once in a while are just a natural phenomenon, like earthquakes. They just randomly happen, right?
2. Is Canva Next? Why Founders Should "Run, Forrest, Run" to the NASDAQ
Because it's not like, if you did a direct listing, people would have said, “Yeah, I think I should pay 8 times run-rate revenues for this puppy.” It would have been the same analysis at 15 times or 20 times run-rate revenues: $35, maybe $38. You might have captured the 2 or 3 extra dollars that you left on the table, in return for getting Fidelity.
And then you would have had the Brian CEO comment of, “Is Fidelity worth 3 extra bucks?” But what you would not have done is place the stock at the lofty level it is now.
So it may well be that mega-pops are a natural, intermittent consequence of the IPO process, and that a direct listing doesn't solve that part of the problem. I'm sorry—was that as clear? It's kind of weird. What you're basically saying is it's almost like a psychological phenomenon, and I'll give you an example in venture of the same thing. We're seeing it now.
I get it, but it's not, though, because you've got Circle, you've got CoreWeave, and you've now actually had 3 in the space of 2 to 3 months.
Rory O'Driscoll
I think timing in the market matters, and you've had a similar thing in 1999. I think it's a once-in-a-while phenomenon when conditions are adjusting from one more pessimistic stage, which we were in in April. Remember how bearish we were in April? It's only July or August, right?
When people are adjusting, maybe we just don't adjust quickly enough, and the euphoria comes in after the stock gets priced and it's trading. There's a small number of highly speculative assets, and there's a lot of appetite for those assets, so they all just rush in.
It's the venture equivalent of what we're seeing now. When someone with a really big brand name does a round, 6 weeks later many of these companies are doing a follow-on round. Nothing's changed. Everyone bid 120, the brand name won, and 6 weeks later there's a bunch of people doing it at 350. Why? The brand name is in. This is kind of the public-market equivalent of FOMO. That's how FOMO manifests.
Brian Halligan
I think the direct listing is like you're a little bit scared you're not going to get those long-onlys. You're not going to properly market it to them, and 7% to the bankers, in the grand scheme of things, is not that much. I think it's risky unless you're Google or Facebook.
Just to pile on what Rory said, timing really matters. HubSpot went out 3 months before a kind of sister company of ours, Zendesk, went out, and it was just a shaky week when they went out. They didn't get the big long-onlys, and they had a good story, but they didn't get them and they never really got them. They always had a lot of hedge funds in there, and they always had a lot of individuals in there.
Our timing was pretty good—not great, but pretty good. Figma's timing was obviously really good.
Jason Lemkin
But that's super interesting, Harry. Zendesk is kind of a tough tale, right? I don't think Mikkel Svane wanted to sell, right? He turned it down at whatever $20 billion and had to sell for—I mean, $10 billion. These are still good numbers, but he was a reluctant seller, right?
And maybe—and to Brian, I hadn't realized this—maybe part of it was never getting that buffer in, assuming they held, right? He had never gotten that buffer in at the IPO, right? And then you're just—I mean, I'm just watching everything. It's horrible to deal with these activist investors, right? It is. It's a terrible experience as a—
I'm going to unpack this because it won't be obvious to everyone listening what happened there. I had never heard that point before, Brian, and I remember both IPOs as well. What you're basically saying is you guys and Zendesk, I want to say, priced in 2013 or 2014-ish—I can't remember, right?
Right, and then what you're saying is, because of the way your deal came together, you got the long-onlys day one. Zendesk didn't. They priced 3 months early, and the VCs had to put money in the round. It was so tough.
And what you're saying is, 5 or 6 years later, they still didn't have quite as strong an investor base. When they hit an issue and they had activist pressure, it's probably not the only thing that caused them to have to sell, but at the margin, you had a stronger investor base the whole way through.
That's your argument for giving the book and getting Fidelity. Part of it, I would argue, is most of that stronger cap table was—it was more luck than skill. The Mikkel story, the Zendesk story, and the HubSpot story just rhymed. But our timing was better. We had a better cap table. Having a good cap table is underrated.
Brian Halligan
That's why you should take money from me, Jason, and Rory. That's what we tell founders.
By the way, while we're talking about this, just to give the inside baseball on the whole thing.
Brian Halligan
So that night, you’re exhausted. You’ve never been tireder. If my co-founder is really introverted, he has negative energy because you spend so much time with humans, and then that night you have a big IPO party with all your friends. You’re so tired, and the last thing you want to do is go to a party. Inevitably, somebody gets wasted at the party. It’s not the founders. Somebody gets wasted, and it’s a big thing.
Then the next morning, the inside baseball is that we did New York. The next morning, you have a big dinner, and then you’re up on that platform. There’s a huge discussion about who’s on the platform and who didn’t make the platform.
Who’s deciding who’s on the platform? That’s another thing Dylan was dealing with, which is super irritating and probably dealt with a couple of weeks before. Did the VCs make it onto the platform, for example? That’s going to be very important to the VCs, to be up there, right?
Brian Halligan
Yeah. You don’t want to take your picture staring at the big drape of Figma outside Wall Street. That’s pretty embarrassing. That went on X.
Okay.
Brian Halligan
And just a pro tip to the listeners who are eventually going to go public: we’re on the platform, it opens, and everyone on the floor is up there looking at you on the platform. Most companies just kind of sit there like, “Yeah, yeah. Yeah, yeah, yeah. Clap.” Everyone down below is like, “Oh, they’re so boring.”
3. CRV Shrinks, Benchmark’s Bet, and the Future of Venture Strategy
You have to have a plan to do something interesting when you’re up there to get the floor excited and to get the press excited. That’s one thing. Then the market opens, and in my head I thought, “Well, we’re trading. That’s it.” But what happens in Figma, what happens in HubSpot, all these things, is that it takes a while for that first price to settle in.
You and your executive team, and maybe your VCs, are all sitting there extremely awkwardly on the floor of the New York Stock Exchange, looking at a million monitors. You’re not trading yet, and it takes a couple of hours for the darn price to settle in. It took Figma about 6 hours, and it finally settled in. It was like, “Okay, okay. It’s $33. Great.”
I remember that moment because my co-founder, likely Dharmesh, who’s a prince, had the stock app. He showed it to me and said, “Brian, look, look, look. We’re worth $1 billion.” I remember saying, “Take a screenshot. We’ll never see that again.” We were so excited. That’s the behind-the-scenes on the floor.
The other pro tip is that you can do NASDAQ or the New York Stock Exchange. They’re virtually exactly the same, except with the New York Stock Exchange, you get to ring the bell. That’s why we picked the New York Stock Exchange.
That’s really sweet. We did one in Cboe, where you get to ring it, but in an empty TV room. It was kind of very soulless. You’re pretending to be excited.
But no, you’re right. The whole point of the dinner—remember, the dinner comes right after the pricing committee. My mental model of the dinner is that the bankers have just screwed you over for a buck a share, and in return they buy you a very expensive dinner and liquor you up so you forget.
It’s totally discordant because you’ve literally come, as Brian said, from a very angry meeting where these people who’ve been your friends for 2 weeks on the road, carried your bags, and done everything for you suddenly start picking your pocket and telling you that they have to give money to their friends. It’s controversial, you argue, and then at the end you walk away and go back, and then they all ply you with liquor, right?
Remember, this is the information asymmetry. 1 day later, you drive out of town, and they bring in the next group of their best friends. The next lamb is led into the slaughter, baby, right? That’s the deal.
But it worked. I mean, where else in the world are you going to get a couple of billion dollars for 2 weeks’ work?
Brian Halligan
Oh, in Silicon Valley, you get it every day. That’s happening now.
Well, this is true. This is.
Brian, can I ask you one meta question on this? I think I know the answer. When you look at Bill Gurley’s criticism of all of this, one is all the money left on the table, right? That’s the math. But I think underlying that also is dilution, right?
Most early-stage investors, as investors—not as founders, because I’ll ask my question—dilution does creep up on you as a founder who’s gone through this journey, right? Did you ever sweat any of this dilution, the IPO dilution, the post-IPO dilution? Did it even come into your calculation, or did you just not care?
Brian Halligan
My net worth went from X to 100x. I was just happy to be there.
4. Why CEO Compensation is Broken
That sentence is why this process is so hard to change. The profound truth is, as Brian said, you’re doing this once, and it’s the most important thing in your life. All these guys are doing it every day, and they know so much more than you. It’s a really hard process to reform. It’s one of those ahas.
I do want to stick on that. You said your net worth went from X to 100x. I think an element that we chatted and texted about before, Brian, that not enough people are talking about is actually the package that’s in place for Dylan, which is obviously this kind of $2 billion moonshot grant, kind of Elon Musk-style.
Brian, we were saying that we don’t talk enough about CEO comp. Why don’t we start with you, Brian, on this, given that you’re the best person here to speak about it? How do you think about this, and how did you analyze that?
Brian Halligan
Yeah, I think CEO comp is pretty broken at the moment. There are 2 things that I think are pretty broken about it. The first is that everyone really relies heavily on RSUs.
When I grew up in the industry—I hate to be that guy, being like, “Back in the old days”—it was mostly ISOs. It was options until 2006, when regulations changed and the expensing of that changed. So the world kind of moved to RSUs.
It creates sort of risk-averse behavior in the CEO. Cash comp goes up and down a little bit, let’s say, but with an ISO, you’re swinging for the fences. You have a strong incentive to swing, and so it’s really had a dampening effect on the risk-seeking behavior of a CEO that I think more companies should want. It’s kind of pervasive across the industry.
I don’t like this RSU comp thing. That’s the first problem I see with all this stuff. The other problem with comp is that almost every company looks at CEO comp, and the way it works behind the scenes is that HubSpot has a compensation committee. Everyone’s got a compensation committee.
HubSpot wants to pay the CEO, let’s say, at the 75th percentile of what her peers make. We look at 20 different peers of similar-size companies and peg her at that 75th percentile, which in her case is $20 million—a lot of money.
Now, if you did that for Dylan, who would be in our comp group with a similar market cap to HubSpot, he’d make $20 million a year. But if you think about it, that’s less. That’s like 3% of Dylan’s own personal net worth. It doesn’t move the needle. It doesn’t matter at all to him.
You have to get creative. I actually like what they did with his comp. They use PSUs very heavily, not RSUs. I like the idea of not pegging your comp to your peers, but you kind of have to peg the comp to the net worth.
It’s the same thing with Elon Musk. If you paid Elon Musk what Mary Barra makes—$29 million a year—do you think Elon cares about $29 million? You have to kind of comp it to the CEO’s net worth as opposed to just the peers. So that’s what I like about this.
I broadly agree, especially on the process side, and you’re right on the PSU. I knew you were going to come in on that, so I’ll just save you the trouble.
A PSU, basically, is an RSU that’s like an option but with a zero strike price, so it’s guaranteed money. Brian’s right on all the negatives there. PSUs—performance stock units—have evolved to effectively make the RSU more like an option.
What you’re saying is that it’s guaranteed money, but only if something happens. The typical thing that people are pegging it to in the public markets, even though I don’t agree—and I’ll come back to it—is stock price. Right?
In other words, instead of saying, “Here’s 10,000 shares no matter what,” it’s, “Here’s 10,000 shares, but you only get them if the stock price is $40.” What you’ve bizarrely done is recreate options, because they got regulated out of existence in 2006. Now you’ve effectively recreated them. The PSU is making an RSU more like a stock option.
Brian Halligan
I like that.
I know. In general, I do too. But watch this. The problem with the Dylan comp package—I’m going to say it didn’t work—is that if you look at it, the problem with stock-price triggers for compensation is that it sounds rational, but they put this in place before the IPO. If you read the triggers, they’ve already achieved them.
The weird thing—and I’ll tell you why they do that in a second—is that all these triggers effectively said that you’ve got a whole bunch of price targets up to $118 a share, I think. When they were making those triggers, literally 2 months ago, they were like, “Yeah, this is going to be great for the next 3 years, but totally out of Dylan’s control just because of the way things have priced.” He’s made all the triggers already.
He still has to vest over 7 years, so it’s not like he takes all the money and runs, right? But the performance element vanished very quickly because of the pop. The aha for me is that I prefer performance-based to not performance-based whenever you can.
I would have preferred, even for a public company, to do them on tangible goals like revenue and operating income and all that over multiple years.
Rory O’Driscoll
And I see, Brian, the problem, and the reason you don't end up doing that is because, A, you have to disclose them, and, B, things change. When you change comp at a public company, ISS and all the whiny babies give you a whole lot of shit.
So what happens—and I've been in the room—is you say to yourself, “I would love to pay Brian Halligan for 35% revenue growth and 35% EPS growth for the next 7 years, and we'd pay him $1 billion.” But if we put that on the table and then circumstances change, we have to disclose it. Then all the analysts will start saying, “Oh my God, they think they can make 35%.” So if they only do 30% growth, Brian missed.
It just becomes problematic, and what they do in the end is say, “Screw it, we'll just do stock-price targets,” which are better than nothing, as Brian says, because it's more swing for the fences. Sometimes you have this weird thing: If you look at all these packages that were put in place, all the ones that were put in place in 2018 worked and gave the shareholders what they wanted and gave the employee—the CEO—what they wanted because the stock price went up.
All the ones that were put in place in 2021 are stranded because all those price targets, like the Airbnb price targets, ain't ever going to happen now. So it's an imperfect mechanism, as comp often is, but directionally the right approach.
Brian Halligan
I'm not in violent disagreement with what you're saying. At HubSpot, the way HubSpot does it is on net-new ARR.
Nice.
Brian Halligan
And an earnings—like, a floor earnings number. And that's where we ended up, by the way. None of this is perfect. It's like, what's the least bad you can do? I kind of like the way we ended up on it.
That is really nice. I'm curious: Do you have to disclose that? Do you get angsty about disclosing that because you're kind of hinting at what you think you can do?
Brian Halligan
Yes, but people can figure out net-new ARR, and they can figure out what your bottom line is. What we used to do was net promoter score and stuff like that, and that gets really tricky, having to disclose all that.
Rory O’Driscoll
I really like it. Very few comp committees do what Brian does. I think that's so much better than just stock price.
Jason Lemkin
Every growth round that I've seen in my little portfolio—all of them—has had moonshot packages. They're going in earlier, and they're becoming a standard part of how many growth funds win deals. They go in and say, “Yeah, I'll do the deal at $1 billion, but I'm going to give Harry another 7% of the company,” and they're always at least 10x. There's a quid pro quo.
It's not 10x; it's 10x from what I'm paying as a growth investor. Fine, I'll do Clay at $3 billion, but if you hit $30 billion, you guys both share another 10% of the company. So I think this is getting institutionalized earlier and earlier as valuations go up.
It may not matter what any of us think, because the growth guys are adding this to the standard term sheet. The flamiest version is where you literally say to the CEO, “I'll reimburse you in options for the dilution you're taking on in the round.” This is a little more high-class than that because it's saying at least you have to achieve first. But I will say—
Rory O’Driscoll
Usually you get more. What I've seen is, instead of a growth fund saying, “I'll give you another 2% back”—forget that—“I'll give you 7% or 8%. I'll give you a massive package, but I've got to make my 10x,” right? It's their version of the Elon package, right?
Jason Lemkin
And I think what happens there is—my prediction is—and again, I'm often disagreed with on this on comp committees because I've done some of these where I've tried to make them based on tangible targets—what will happen when you do the stock-price ones is, if the company's doing really well but the stock price isn't achieved, the CEO will be sitting down 2 years from now and asking to waive some of the criteria. I can just see the movie now, right? And, you know, so be it, right?
Rory O’Driscoll
Maybe I'll bet you nickels to dollars that it doesn't happen, because founders are just signing up. I don't know what, Brian, you see at Sequoia, but founders are signing up for crazy stuff these days. They're signing up for massive stuff, and I don't think a lot of grouchy VCs are going to waive it. I just don't think it's going to happen.
Jason Lemkin
I hear your point, Rory; I just don't think it's 2024 anymore.
Brian, you are an amazing coach to founders. I speak to Pat, Andrew, and Reid a lot, and they say that founders love your coaching, mentorship, and advice when they have big growth rounds like these with performance-based incentives, like we're talking about. How do you advise them? Is it what you thought you'd see now on the other side?
Brian Halligan
I like all this stuff for the founders. When I came through, it was pretty rare to do that. The other thing I like is founders taking a little bit of money off the table on the way.
For us, when we did our round, Sequoia came to us and said, “We'd like to buy some of your shares.” In retrospect, it was a horrible financial decision for me, but it was good at the time. I sold, I forget, a couple million dollars' worth of HubSpot shares. My co-founder and a few other people did.
What I liked about that was that Salesforce came knocking and wanted to acquire HubSpot. It stiffens my backbone a little bit. So it's good for the founder, and it's good for the VC.
I think it gets a little wobbly when it's a $50 million secondary in the Series B, but in general, I like what's going on in venture. I think the valuation is very high right now across venture, so we'll see how this thing plays out. I think it's a little bubbly right now, but I generally like the trend that's going on in terms of secondaries happening for founders, and I like these PSU-type rounds.
There's a founder I work with right now who's a terrific founder who just took 4 years to get it going, and now it's ripping. He'd been massively diluted, and so I'm like, “Well, let's figure out a way to give you a nice, big grant.”
Rory O’Driscoll
I go back to—yes, I agree with all that, and I do think, though, that valuation is the imperfect metric. And Jason, I think you're wrong. I think investors and grouchy VCs will recut because CEOs are smarter than us at comp.
What I've learned is this: I have empathy, but they are running their company and they obsess about it day and night. Let me tell you, if you've got a CEO who doubles revenue for the next 2 years and the only reason he's not making his extra 3% is because we overpaid 2 years ago and now revenue multiples are normalized, and therefore he's not getting his 5x, he's going to come into the comp committee and say, “I have nailed running this company. We have 3x'd revenue. We're operating-income positive. Give me my damn shares.”
And I'll sit there going, “I knew we should have done revenue and operating income at HubSpot from day 1.” What we're doing right now is we're taking what Bob Bryan correctly calls high-end valuations, and then we're 10xing them, and we're basing comp on that. Brutal. We're basing comp on a chimera. It's never going to happen.
Look at all those 2021 value-multiple disclosed ones. Most of them are like, “What were we thinking? We thought that we'd go from $200 billion to $2 trillion.” Maybe not.
If we think about going from $200 billion to $2 trillion, there's going to be a boardroom that's going to be thinking, “Huh, should we take some action now?” If you are Canva, are you looking at this going, “Forrest Gump, run—let's head to Nasdaq”? How do you think about the impact of this on Canva and subsequent companies' willingness to go out?
Jason Lemkin
Yeah, run, Forrest, run. The market's wide open. The valuations are good. There's a lot of demand. It's very seasonal and oddly seasonal, and timing really matters. If I were Canva—it's an amazing company—I would be lining up, lining everything up, to go public.
But the founders have already pledged to give away the majority of their stock. It's not about money for them. The company's profitable.
Jason Lemkin
They're going to give it away to good causes, and they want those causes to get as much as possible.
Yes.
Jason Lemkin
I'm not saying I know the answer. I just think it's more complicated than someone who needs the money. All the early-stage investors have had a chance to trade at tens of billions, right? And the founders—there's just a lot of liquidity already there. The company's massively profitable. I just can't—I'm not smart enough to predict how those factors stand together, right?
This clearly isn't a Musk empire that's being built in Canva, right? It's very different, right?
Rory O’Driscoll
I think you have—I've been thinking about this. You have all the idiosyncratic personal things. You have people who say, “I don't want to go public for a long time,” and you have people who need to go public early, right? All those are idiosyncratic.
But if you zoom out 1 level, I just had this conversation with an LP. They're asking, “When does it open?” In the end, price clears all markets. For the longest time, the money in the private round was cheaper and less hassle for the last 3 years than the public market, so no surprise we did more private.
Let me see: 5x revenues with a bunch of people in New York busting my balls versus 10x revenue, and I never get to talk to these growth-stage guys except once a year. I'm doing option B.
Right now you have a situation where maybe, at the IPO price for Figma—20, 10, 15 times—I should be 18 times revenues. You kind of go, “I can get that privately.” You can't get 80 times revenue privately. So if you're now looking at where things are trading today, I think at the margin those prices are higher than the private things.
Jason Lemkin
So, stepping back from the idiosyncratic stuff at the highest level, the cheap money is now in the public markets. Brian's right: you'd be an idiot not to go for it. If you need to raise money in the next 2 years, now would be a really good freaking time.
5. The Case for Going Public: VCs Are a Bigger Pain Than Public Markets
Brian Halligan
Can I just build on that? In Silicon Valley, I think Stripe is really beating the drum on this: why the heck would we ever go public? There's that sentiment out there because there's so much private capital and you can do secondaries.
I don't have a violent disagreement, but I think people are just nervous about what's on the other side. My take on it was, when we were a private company, we had a bunch of quirky, slightly misaligned venture capital investors who were definitely in our shorts. Then we flipped to public, got rid of those VCs, and had a bunch of quirky, slightly misaligned public investors who were less in our shorts.
It's actually better in a lot of ways than being private. There's so much written about what happened with Zendesk or Autodesk, or these really bad things that happen. It's pretty rare, and I have found public investors to be pretty rational if you paint them a picture of what will happen over a long period of time.
If you're pretty conservative with your numbers, they're rational and they'll stick with you. I think they're underrated, and I think people think it's something scary over there. It's not as scary as people think.
I have a lot of founders who say, “I'm terrified of the activist investors. I'm terrified about what happened to Jeff at Twilio. This is my company. This is my life. I don't want to have that happen to me.” What would you say to that founder?
Brian Halligan
It's pretty rare what happened to Jeff. Everyone talks about Jeff, and everyone talks about Zendesk, but it's pretty rare. That company was having some issues.
Rory O'Driscoll
I agree. I agree about it, and I am a “we should go public” person. I think it's a little overwrought. Yes, some of these issues do happen, but overall, I think the activist VC—because we were one of them—
Jason Lemkin
VCs are a much bigger pain in the ass than public investors.
Brian Halligan
We are much agreed.
Let's add that to the B-roll.
Jason Lemkin
Yes, I think VCs are a much bigger pain in the ass than the typical public investor, and slightly less of a pain in the ass than the public activist investor, right? I remember saying that one. Believe me, I'm pretty sure on that one, right? I'm going to defend us there, Brian.
Most times, the public guys are benign. Though I will say, in the last 5 years on the venture side, definitely the benign content has ramped up. The marketing in the last 10 years on the venture growth side has very much been, “We are benign. We are more benign than the public investors.” I think that might be misleading. That might not be true. That might be reliance on preference.
I think you're right that it's a healthy trend to realize that you can go public, you get this liquid stock, and it's not as terrifying as you think. You have liquidity every day, not just once a year by appointment only. I'm a big “IPOs should happen” person, and I think that—
Brian Halligan
Here's what's underrated about the IPO: it's very stressful. You're exhausted, but the day you go public is going to be one of the top 2 or 3 days of your life. It is an amazing day. You'll go back to your company, and 2 days later you'll have a party with your company. You will cry, you will laugh, you will hug. You worked so hard. There's something about that that is really, really special that people—
Jason Lemkin
Having said all that, I've only lived through it on the employee side, when it was great, right? The day after that was weird, going back to your desk because the world's changed. The next day is really weird.
But if I could IPO at $30B or sell my company for $30B in cash, I'd much rather run the company—don't get me wrong—rather than sell, right? But if it were just a financial decision, I'd rather have the $30B on one day than wait a decade for it to drip and dribble out, right? So there is a conflict there as a founder.
Selling is tough for 98% of founders. I'm sure if you ask Sequoia, only 2% of founders say it was the greatest experience of my life selling my company. But, man, getting it all at once if it's the same, even with a net present value, it's just a weird trade-off between the two: the journey and the economics. It's complicated.
I just want to butt in there, Jason, because you said there about getting it all at once versus drips and drabs. I'm super naive here, Brian. You said about it going from, like, 1× to 100× when you do go public. Is it drips and drabs over years? How does that—
Brian Halligan
Is it dripping and drabbing? If you can look at the way I do it, I sell the same number of shares every month since we went public. The reason I do that is I don't want people to think I'm signaling something. If I make a big buy or a big sell, it's going to signal something. It's funny: investors will look at it.
So I just have the same exact number of shares I sell every month. It's on autopilot, and it's drips and drabs. You're definitely right.
Do you know how much you have left?
Brian Halligan
Yeah, I've got plenty left because I got more shares. Here's the thing that I didn't understand as a founder: you get more shares as time goes on. I actually didn't know that when I started hustling. I thought the pie would get smaller. Actually, the pie was much smaller, and then it started growing a little bit.
Jason Lemkin
One of the things we didn't warn you about joining the podcast, Brian, is that every once in a while Harry basically asks you to disclose your net worth. You have to remember, it's like in a prison cell: you don't have to answer. You can plead the Fifth on anything, right?
Brian Halligan
No, Harry, I will not disclose my loss rate on deals or term sheets, nor my net worth. Just refuse. Point blank.
You handled that very well, Brian. Rory, what was your multiple on HubSpot?
Rory O'Driscoll
I'm not going to disclose that. It was extraordinarily good, and I'm extraordinarily grateful to Brian for allowing us to do the Series C, especially when I had whiffed the Series B and my colleague Rob, and then Stacey, took over and did the Series C and corrected my dumb decision. We were extraordinarily lucky to invest in them at something like a $70M pre-money valuation on a company doing $10M. Thank you, God, from the bottom of my heart every time I go to my little house. Thank you. Thank you, Brian.
For the backstory on Scale's investment—
Brian Halligan
It was the Series C, and it was bad timing. That timing matters more than I ever would have thought or studied in school.
It was in the throes of the recession back in 2009. Dharmesh and I got off the plane from Boston, landed on Sand Hill Road, and we were like, “We've got this. We're going to go up and down.” It was 20 meetings, and we went to all 20 meetings and got back on the plane. We were like, “We got no offers.”
Up and down Sand Hill Road, every big-name firm—every household name—said no. We went back and forth. We had nothing. So we were about to do an inside round at a slight uptick to our Series B. At the very last minute, Rory and Rob Theis had us in. We pitched them, and they gave us a term sheet at $66M.
So actually, the thanks goes from me to you, Rory, because you marked up our deal. I appreciate you.
Rory O'Driscoll
Synergy. We call it synergy.
Absolutely. No, yes, I remember that was in '09. We did HubSpot, Box, DocuSign, and RingCentral. The time to buy is when everyone else is not buying, especially when—let's put it out there—you're just little old Scale and you're not Sequoia, who came in after.
The world might have to end, and that's obviously a little tough for everyone, but it'll be really great when companies like HubSpot are grateful to get my term sheet seat at $66M pre-money. Just to remind everyone, at that point they were doing somewhere between $7M and $10M, doubling year over year.
Other than that, it was a tough decision. So grateful. Thank you very much. My multiple was excellent, Harry, so pound sand. It would have been even better if we had had the mechanism then to hold for longer after the IPO. I profoundly wish we'd had that as well.
Jason Lemkin
The smart money on HubSpot was in the public markets, since we went from $1B to $25B in a relatively short period of time. That was the play with HubSpot, and I think Sequoia is really smart. I suspect that was one of the reasons why they said, “Let's hold these companies after they go public.” It's backfired in some cases, but I think it's going to work over the long haul.
You couldn't hold, Rory. You weren't allowed to in your LP.
Rory O'Driscoll
It's a long story. We had a single LP. We had to distribute. It's a long story. Move on.
Don't you love the way I asked Rory for the multiple? He's like, “No, no, no, moving on, moving on.” And then Brian's like, “Let me tell you how he missed it in the B,” and you're like, “Oh, I prefer the multiple question. Let's go back.”
Jason Lemkin
No, I'll give Rory credit. As great a company as HubSpot was, it clearly wasn't a consensus bet at the time, objectively.
Brian Halligan
Marketo was the consensus bet.
Rory O'Driscoll
Marketo was raising at bigger valuations. They were always raising 3×.
Jason Lemkin
Well, they were more enterprise, Brian. That's the play. You’ve got to go more enterprise. Yeah.
6. Can AI Even Work for SMBs? Why No One’s Cracked the Code (Yet)
Marketo. It's Marketo, correct? Yes—Marketo. And it is actually worth riffing on that because we have the king of SMB on this call with Brian. I mean, you're right: the interesting thing about HubSpot was the way they built a $30 billion market-cap business in SMB, starting with sub-50-person employee companies. And you're right, Jason, it was very counter-consensus wisdom at the time.
Brian, any thoughts on that? What was different about it? Did you ever want to go upmarket?
Brian Halligan
The reason we bet on SMB was that I had spent my entire life doing the soul-crushing exercises of selling to CIOs. It is just soul-crushing work. I didn't want to do it. And I also felt, at least back when we started, that the internet disproportionately benefited small relative to large. Your success was much more about the width of your brain than the width of your wallet, and so we had sort of a play on that.
We also looked at the consumer business. Actually, the P&L is a shitty way to look at these businesses. Let's look at CAC and LTV. We kind of convinced ourselves that it worked. One of the interesting things about HubSpot SMB is that the other SMB company that's done amazingly well, even better than HubSpot, is Shopify. They're both outside of consensus land in Silicon Valley.
I think there's a big echo chamber in Silicon Valley and a big negative bias toward SMB, but you can make it work in SMB. HubSpot and Shopify have shown it. Block has shown it.
Jason Lemkin
Monday.com as well—massively anti-consensus. Totally agree.
Rory O'Driscoll
Yes. I think they're moving to enterprise.
Yes, they are, in a way that you guys didn't. Would you have made the choice today, Brian, in AI? The reason I ask is that to make a lot of great AI products work, you need training, you need forward-deployed engineers, and you need daily—even if it's SMB, every day someone's got to be your AI orchestrator. If you were doing all that today, would you go a little bit more mid-market? Because these SMBs don't have time to train their AIs.
Brian Halligan
Yeah. In fact, here's one of the interesting things about my life: all these founders come to me and say, “How did it happen with HubSpot? How did you do marketing?” We talk about our Website Grader, content marketing, and inbound marketing. “How did you take on Salesforce?” I kind of came up with freemium, and we learned a lot. We innovated a bit, and a lot of what we learned just wouldn't work today. You’ve got to keep innovating. You’ve got to keep turning that over.
I'm careful to give people advice and tell them what we did at HubSpot because it worked at the time. It was really innovative at the time. But a lot of what we did on go-to-market, a lot of the freemium stuff, a lot of the PLG stuff, a lot of the interesting culture stuff, and our SMB play—some of it works, some of it doesn't.
Some of it works, some of it doesn't, I think. Right?
Brian Halligan
Some of it works, some doesn't. Yeah.
Do we have Jason? I'm just literally—this is me exploring, not knowing the answer. What are the great SMB AI products? Is there a great SMB AI product out there today where you go, “That…”? Well, Lovable's a stupid question, Rory. I mean, you could argue that what you seem to imply is that it's harder to do enterprise-kind-of-SMB-level apps in AI because of the need for training data. Then I'm trying to think: what are the mass-adopted enterprise apps? Obviously, you're the Lovable and Replit guys, so there are some. I don't know others.
Even the exceptions sometimes prove the rule. I mean, I'll tell you, I learned a lot of AI from Brian's AI. I copied it and made it better, right? When Brian built his clone, he and I were talking in the very beginning. He's like, “Well…” I'm like, “Brian, it's pretty good.” I had some fun, cathartic conversations with Brian's AI, and I had some fun ones. I'm like, “It's pretty good. Mine's better, but only because it's trained on more data. Mine is better.”
Jason Lemkin
But I didn't get it. I asked Brian, “Why is yours so good?” He said, “I spent a lot of time training it.” This was 6 months ago. That's a lot of time in AI, and I didn't get it, right? But now, when I look at every true AI company, it's hard to train it.
This is a quandary for SMB investments, right? What I'm looking for in SMB companies and AI is: how do you self-train? How do you solve the unsolvable issue? How do you solve the fact that it can take 6 months to roll out a Palantir-grade deployment? How do you do that in 60 seconds? Any founders that crack that code, I want to invest this hour, this second.
I'm pushing every startup I work with that's SMB to be more AI, and sometimes they push back on this, right? But you’ve got to do it. How do you train? How do you train the training?
Rory O'Driscoll
The stuff I see, Jason, is that there's a ton of prosumer stuff that's working. Lovable's working, Gamma is working. So many prosumer things seem to be working, and then enterprise is working. You're right, I haven't seen much in between.
Jason Lemkin
But there's no training in the—I mean, we use Gamma too. We love Gamma, but you don't train Gamma. You do train Gamma a little bit, don't get me wrong, but you sort of accidentally train Gamma by uploading your templates and your things, right?
Replit and Lovable—I mean, I'm Mr. Vibe Coder, right? Those are AI under the hood. The training is weird, though. It's AI under the hood. I just think this AI B2B SMB is something that hasn't been cracked, to Rory's point, and I think we should all just rush all our capital into that.
Listen, if you can train an AI, it's easy. HubSpot just put out this report on AI with SMBs, right? It said something like 80% of folks have an AI team to do this. Even with what they call SMB and VSB, 80% have a team. SMBs don't have a team, right?
The owner doesn't. The owner of a restaurant—one restaurant that Brian and I are invested in—they don't have an AI team, right? At Brian and Jason's sandwich shop, there's no AI team.
As I say, I opened the door to a non-prepared topic, so I'm winging it, but my sense is two comments. One is it may well be that it takes a year or 2 longer, because if you think about even the HubSpot journey, what tends to happen is the big companies with loads of money fart around, kind of mentally defining these apps and figuring out what they should be, because they can afford to. Then, where the features lock in, the SMB guys go, “Oh, we'd like that,” and you don't have to do as much of the figuring out what it is.
In the case of this generation, you probably come with a very much pre-trained app where, if it's call answering or something like that, most of it's already done and you just have to configure it at the SMB level. It may be over the next year or 2, because I do believe—and this is, I think, one of the reasons we love HubSpot—that anything the big companies have, the small and midsize companies want too. They're not different; they just need it packaged tightly and priced tightly so they can consume it in bite-sized chunks.
7. Meta’s Monster Quarter: Growth, Cash Burn, and the Real AI Strategy
Over the next couple of years, it may well be that for things like phone answering and simple order dispatch, there'll be a whole bunch of pre-trained, pre-baked systems: “This is how it works, Mr. SMB. Just turn it on, and you, too, can sound like a big call center.” So I'm optimistic. It won't be trained on a company-by-company level, but I think it will deliver big-ass value.
You said there about big companies with lots of cash. I do want to progress this, because there's something I'm fascinated to hear your guys' thoughts on. Meta—what a freaking ripping quarter. It was a 38% year-over-year increase in adjusted EPS, 22% revenue growth, but a 22% drop in free cash flow. How did you guys read it? How long does this go on for? Is this the start? Is this near the end? How much patience do people have?
Brian Halligan
It's funny you led with the “How long does it go on for?” because 2 weeks ago, when I said, “How long does it go on for?” you looked at me like I had 2 heads, right?
You see the shit I put up with, Brian. I just take it.
Brian Halligan
No, I'm polite. I don't give it back. I just take it.
I will say, on all these things, the takeaway—and I like the way you framed it here, and not the way you framed it in the note you sent me prior—is this isn't an AI-enabled success. This is: I have an awesome existing business, and it kicks off so much money that I'm allowed to spend that money on building this great AI vision. I can probably do that for as long as my existing business kicks off cash.
My big aha from this week's earnings—and I would say I got broadly AWS right and I broadly got Microsoft wrong—is that not all the AI stuff is working for the hyperscalers. My big takeaway is that all their existing businesses are working so well and kicking off so much cash that they can keep doing this for the next year. They said they're going to keep doing this for the next year because they want to play in the new game. That's the takeaway.
Real men with $700 billion in market cap and $70 billion of free cash flow get to spend $40 billion of that on servers. It's a great country.
Is there any nervousness at Sequoia, Brian, at all, that the good times might end soon? Is there any draft Sequoia memo, version 3, ready to go out? Just search and replace with Gamma—just have Gamma, please. Dust off the “RIP good times” and update it for AI.
Any discussions at the partner meetings you’ve been in about that? I mean, David Cahn wrote the piece about the gap between capex expenditure and revenue.
Brian Halligan
Yeah, I think we’re in a kind of—one of the questions is, are we in a bubble or not? The argument against the bubble is: look at Anthropic and ChatGPT. The growth rates are ridiculous. Or look at Harvey, or so many of these companies that are at the app level.
As an investor looking at this stuff, I get nervous about tech companies selling to tech companies and Silicon Valley companies buying from Silicon Valley. There’s a lot of trading going on, and there’s a lot of growth in there. I like what ChatGPT is because it’s mere mortals using that thing. I love what Harvey’s doing; they’re selling to lawyers. I like what Rogo is doing, selling to investment bankers.
I get nervous because I think 2001—and definitely 1999 and 2000—it was just Silicon Valley companies buying and selling from each other, and it created kind of—
2022, though. 2021 too. A lot of it—
Brian Halligan
For sure. Yeah, for sure. So I kind of like these ones selling to mere mortals—
But it has to be a bubble at some level. The capex—this is the capex bubble. It can’t last forever, right? We can’t—
Jason Lemkin
That’s Harry’s point. Look, AI is bigger than the internet, most likely, right? Bigger. So the investment makes sense, but when you see Meta’s cash flow decreasing, there’s some kind of bubble here, right? Hopefully we all get out, but it’s some kind of bubble.
Rory O’Driscoll
“Bubble” is a laden word, right? It implies—I just think you invest. It’s the usual two things. There’s an enormously enabling technology, and it’s getting massive traction at the apps level, as Bryan mentioned. But you still add up all the apps’ revenue, and it probably comes to $25–30 billion maximum, while the capex to build that is running between $400 and $600 billion.
So you’re investing $400–600 billion a year to enable a $25 billion ecosystem to go and keep doubling. Maybe next year it’s $50 billion. My takeaway is that the long-term trend is almost certainly real. If you fast-forward 10 years, that $25–30 billion of apps revenue could easily be $300–400 billion. So, in the long term, it’s not a bubble.
There’s probably going to be a period where things get ahead of themselves, right? The marginal player will get caught, just like the marginal player got caught in 2001. The overlevered player who’s taken on too much debt—financiers will get caught and get burned. The big guys will retrench for a year or two and then just grow into it.
That’s the most likely version of the movie: some pain at some point in time. It’s boring because it’s not amazing AI maximalism, and it’s not bubble doomerism. It’s just that we’re doing what we always do with a new technology. We’re spending like crazy because it’s the only way to discover the frontier, and until you discover the frontier, you’re not investing enough.
We’re doing it as an organization, or as an organism almost. Capitalism is working. We’re spending money trying shit that works. Some of it won’t work, but unless you try, you just end up like Europe. Sorry, Harry, I just shit on you. You’re so Irish.
We’ve had 800—
Jason Lemkin
He talks more European than you do, Harry.
Harry, we’ve had 800 years of you guys shitting on us. Every chance I get to shit on your back, I’m going to take it. So just get used to it, man.
Aside from the navel-gazing on this, because I don’t know what the answer is, I would just say I’m incredibly impressed at massive scale with how fast Microsoft is growing and how fast Meta is growing. The companies people aren’t talking about are the very old-school Microsoft, SAP—and how about Oracle?
Jason Lemkin
Oracle.
Absolutely. How about Oracle? My date is August 26, 2022. That’s when everything kind of hit the bottom in share price. If you go from that date and you look at Oracle and SAP, they’re both growing about 230%.
Jason Lemkin
Are you talking stock price or revenue growth rate?
Stock price.
Jason Lemkin
Yeah, you’re becoming a stock-price baby.
Yeah.
8. CEO of the Year? Why Jensen Huang Leaves Zuck & Satya in the Dust
Jason Lemkin
The lower you start, I mean, I think part of that is a function of the fact that they started at a much lower pace. But I think you are right, though. The stunning thing in Oracle’s particular case is how they’ve, rightly or wrongly, taken that free cash flow and invested it in GPUs and have now made themselves relevant in cloud. Provided that market keeps growing, that’s clearly worked for them so far.
Rory, I know you love unfair questions. I’m going to give you the chance to grant a CEO of the year award, and you can grant it to Satya or Zuck. Which one do you give CEO of the year to?
Rory O’Driscoll
You know, I’m deciding I’m now going to be the new humble me. It’s inappropriate for me, a little grasshopper, to comment on which of those two amazing CEOs is the best. They’re both GOATs.
I think the CEO of the year is Jensen.
Yes, that’s—I’ll go with that.
[Speaker?]
Yeah. And I like him. But the other thing I like about Jensen is that he’s rethinking the role of the CEO. He’s rethinking the CEO playbook. I think he’s a pretty good inspiration for CEOs out there today. I’m a huge—
I’ve certainly gone as long as you can go, right? He’s the number one on my CEO list—
Jason Lemkin
Because I think, of the two, the reason the two people you cited are not—well, in one, it’s very much an existing business carrying and doing something in the new world, whereas with someone like Jensen, or Sam at OpenAI, or Dario, we’ve created the new world.
I think the two people who have the two categories in the stack that didn’t meaningfully exist at scale in SaaS and cloud land, and that exist now, are the GPUs, which is all Jensen, and the models. Neither of those categories even existed. Obviously, not only do they exist, but they appear to be dominant relative to the other parts of the category, either apps in AI land.
So I think Rory’s right. Those are the contenders for CEO. The other guys are contenders for managing the cash machine brilliantly at scale and keeping it up and to the right, which turns out to be a pretty lucrative way to spend your adult life.
[Speaker?]
I’ll tell you why you absolutely have to go for Satya over Zuck, by far. It’s a simple—it’s more of a structural reason, and this is certainly what I learned in my tenure as a VP at Adobe and as a founder. This stuff’s easy. You just call the troops together. Zuck can do what he wants.
Satya having to get—I just watched Adobe trying to go to the cloud. It took 3 years of convincing everybody. What Satya has done—inviting Sam Altman back in, doing the deal, managing the deal, investing the money, doing this kooky deal to buy 49% of OpenAI, investing all-in on Azure for AI—he doesn’t have the power to do this on his own, right?
I mean, Brian and Dharmesh can get together and honestly, you guys can just decide what you want to do. I know I’m being simplistic, but I bet you’d agree. For Satya, the amount of meetings and orchestration and stuff you have to do as a non-founder—it’s much harder.
He’s like a refounder. He basically acts like a founder. He gets stuff done like a founder. It’s super impressive.
Brian Halligan
If you accept the constraint that you can’t build the core technology internally, which is what Microsoft had to accept, and he accepted, right, execution since then has been perfect. You found the only other people that had the technology. You gave them a convoluted deal, you sucked a lot of value out of them, and you have the ability to resell it. All those things are awesome.
At some level, you must kind of wish, as the CEO of Microsoft, that there’s a little part of you that says, “If my guys were only smart enough to build the shit that OpenAI was building, I wouldn’t have to do all this crazy stuff.” But maybe that’s the nature of being smart enough to accept that this large bureaucratic company can’t get it done and live with it.
Maybe that’s the answer to why it’s awesome. He’s lived with the reality of, “I wish my people could do this, but they can’t, and I’m not going to keep banging my head against the wall. I’m going to do this very hard thing for a non-founder to do. I’m just going to cut this weird deal with these other dudes, give them $10 billion, own 49%, and basically ride into the AI business without actually having the core model that you should have had to be able to do it.”
It’s kind of a one-man show. Literally, he must feel—maybe the real sound in his head is, “Thanks a fucking lot. The rest of you guys—I had to figure this out with one BD guy while all you guys were sitting on your ass not shipping AI.” Maybe that’s what he deserves the medal for.
Jason Lemkin
Not easy.
Brian Halligan
Not easy, and he has to suffer and take 49% of the losses.
Jason Lemkin
Massive losses flowing through their financial statements, right? You could argue asterisks and daggers, but it’s not cost-free. There is a cost, right?
Yes, but 3% of OpenAI—they’ll be fine. I mean, 3% of OpenAI in return for, you know, probably a trillion dollars.
You get criticized for this as a non-founder CEO. You get criticized for every line versus Zuck. They’re like, “What are we going to do?”
Jason Lemkin
Just being ballsy enough. You’re right.
What are we—what are we going to do with Zuck? What are we—what are we going to do?
Jason Lemkin
You’re exactly right. Just being ballsy enough to write a $10 billion check for something weird is, in and of itself, heroic.
Bryan, do let us know when you have to go. I know you have the time.
Jason Lemkin
I have to go. No, no, no, no. That’s not how it works.
You’re the best, man. Thank you so much.
9. Cognition's $15B Deal & Mass Layoffs: The Most Savage M&A Move of 2025
Jason Lemkin
You’re good. Thanks for inviting me.
Guys, I do just want to go to a couple of private rounds, just because they’ve really stood out to me. We’ve said, about companies that we’ve talked about before, Cognition is now rumored to have done a round at $15 billion. The new combination is obviously Cognition and Windsurf. Both had $85 million in revenue, so combined, you’re at $170 million, being priced at the new $15 billion. How did we think about this?
Jason Lemkin
It didn’t move a ton, in the sense that what you’re saying is the rumor was it was being done at $10 billion, and now the rumor is it’s been done at $15 billion.
I mean, you know what? The cynical take is pretty much the same as the Anthropic rumor. It was done at $100 billion, and now it’s being done at $170 billion.
Jason Lemkin
I think what it says is demand is high for premium assets. It’s a little like the private IPO: You float a price of $100 billion and you end up at $150 billion. You close at a price of $10 billion, and you end up at $15 billion. I think there’s just a lot of demand for premium, perceived-premium AI assets, and price is how scarce assets get allocated. So, there you go.
What’s the question? I just thought this layoff-and-buyout thing was just crazy.
Jason Lemkin
Separate question, but yes.
Well, unpack that, Jason. I guess today Cognition laid off 30% of the folks they bought, and they offered to buy out all the other 200 employees. They gave them a 9-month package. They told them they either had to work 80 hours a week, 6 days a week, in the office, or they should take a 9-month package.
Jason Lemkin
And listen, no criticism—great people here, right? I’ve had some of my best portfolio companies use Devin, which is pretty interesting when I talk to them, right? But doing this hero acquisition, then laying off 30%, and then telling everybody to either work 80 hours a week in the office or take a 9-month package, the story keeps getting more complicated. Then finding out that the founders and the investors put in the $100 million—Google didn’t—the story is more complicated than it looked at first, right? There aren’t quite as many white hats, and everyone’s a gray hat, it turns out.
Okay, but let’s just unpack that. Why make the acquisition, then, if they’re going to get rid of 30% and then say, “Hey, all of these terms are posted if you’re buying the team”?
Jason Lemkin
I don’t think they’re buying the team. I think it’s clear they weren’t buying the team. Listen, my limited experience with Devin is that it’s an AI engineer, okay? I talked to all the folks in my portfolio. The 2 actually toughest-problem CEOs are using it, okay? Stuff where they’re reluctant to use AI. They like Devin, but it only does a little bit. They pay for it, it’s fine, but they’re not deploying it across their whole team like Claude Code or something.
So, they have a niche product that’s done well, and they want access to a top platform to get into everybody—a broader platform. They bought a brand. They bought $80 million of revenue to maintain, right? And they saved themselves, who knows, 3 months to 9 months. They basically did a deal that looks non-dilutive at the end of the day at this $15 billion.
Maybe there’s just a lot of spin on a deal that was just for brand and an accelerated market entry. I don’t know. The fact that they’re offering to let every single employee go certainly means they don’t see a lot of value in the folks that are left. There’s an implicit cultural statement, and again, they’re basically saying, “We’re all working 9 to 9, 6 days a week, and you guys aren’t. If you want to sign up for this, do; if not, leave.” I mean, you’re right, there’s an element of clarity to it.
They’ve got until August 10 for all employees to decide whether they’re staying or going. It’s a lot of change from the last pod.
Jason Lemkin
But all predictable, I mean.
Bye, guys.
I’m not laughing because the human implications here are so stunning, right? I mean, Google’s such a jerk: “We don’t want anybody. We want the company to die.” Then the investors and the founders having to take the $100 million out of their own pocket and leave it in Windsurf. Google didn’t do it. They had to do it after the deal was handshaken, apparently.
Then it all happens. Then they get bought at the 11th hour, and now everyone gets a buyout package. It’s just—I mean, even in a 9-to-5 world, it’s too much.
Jason Lemkin
Yeah. And what you don’t know is, because they all had the common part of that, they got their equity cashed out. What you don’t know is how that compares to taking that $100 million, closing the company down, and splitting the money. So, yeah, you don’t—I genuinely don’t know how they ended up.
But what it says is this: If you’re not one of the key players, the minute you move away from the cap table to making it up as you go along, you’re very vulnerable. You’re basically depending on the kindness of strangers, as Blanche DuBois would say, which is always a mistake, right? You’re depending on arbitrary people deciding, quote-unquote, what fair is, and people’s decisions on what fair is change over time, right?
Versus in a normal M&A, where you know where you stand. It’s a Delaware corporation or a Nevada corporation, and you get what you get. I think the lesson here is, once you get away from that, everyone’s just winging it, and it’s hard to know from the outside.
Did you quote A Streetcar Named Desire?
Jason Lemkin
Yes, I did.
In a VC pod? My respect and love for you has gone through the roof.
Jason Lemkin
There you go. There you go.
That is fantastic. You know what?
10. Ramp’s $22B Raise: Genius Move or Suicide Round?
Jason Lemkin
Just a little bit of the humanities, right? Well, now that computer science is on, I’m going to go back to doing my English lit exam.
Yeah. Well, there are 2 more things that I want to discuss. Ramp raised a $500 million Series E at a $22 billion price. Iconiq led it. This is like the 5th or the 6th round they’ve raised in an 18-month period. So, is this in line with company progression, or is this late-stage capital really trying to find a home?
Jason Lemkin
Probably a bit of both, because remember, Ramp, unlike most software companies, part of what they do is lend money. They basically give people corporate credit cards, on which they earn the interchange. The way you earn the interchange as the issuer is that someone has to fund them for that period—the 30-day float period.
Now, I don’t know in their case: Are they funding it themselves, or do they have some kind of flow-through? But in any event, issuing a corporate credit card, by definition, is way more capital-intensive than simply building a software company, and they’re building both. So, it probably consumes more capital than the typical software company. The faster you grow, the more capital you consume. At some level, there’s going to be just a capital need for that.
On top of that, you obviously have the phenomenon of it being a wildly hot, successful company, perceived as dominant in this category. By virtue of that, it’s just going to attract a lot of venture capital interest. If people keep offering you money at increasingly higher prices, you’re probably going to take some. So, probably a bit of both.
The other thing with these rounds, when I look at Ramp—$22.5 billion, very quickly, but $500 million—it’s only 2%, right? Clay just did a round at $3 billion, which is stunning growth too, right? But they sold $100 million, right?
So, these little, tiny rounds—the absolute dollars may sound large, but they’re not even rounds when we’re talking about 1% dilution, 2% dilution. The VCs get a markup out of it. There’s also a weird set of questions about whether they really count.
I remember back in the day, I had a markup at a $3 billion investment, right? It was a very small number. My anchor said, “Don’t recognize it. It’s not big enough. It doesn’t count, right? It doesn’t count. Don’t. Just don’t.” And he was right. I’m not saying that’s the same here, but if I’m Ramp and I could sell 1% in a series of rounds, there’s no cost, is there?
But do you actually think these are good rounds for companies? I think they’ve been called suicide rounds before, where you raise $100 million at a $3.1 billion valuation. It just sets a really high price for the company to grow into, with actually not that much money going into the company.
Well, that’s the downside, right? Maybe it is a suicide round.
Jason Lemkin
You know, I think if you need the money, you have to get the money. And if you need the money at a high price, it’s better than a low price. I don’t think raising money at too high a price is only “suicide” if you have to raise again.
If you don’t have to raise again and all you do is have some investors who’ve overpaid and they take 4 or 5 years to grow into that valuation, well, that’s tough shit for the investors.
[Speaker?]
But from the company's perspective, it's fine, and you're glad you got the money, right? So I think the number one thing you don't want to do is raise $1 or $3 billion when you needed $400 million, and then go back out 6 months later. You haven't had the growth, and in theory, you're only worth $1.5 billion, but then people get the cognitive dissonance of, “It's a down round and you're screwed,” right?
That's a suicide round.
That's a suicide round. But if you raise $500 million at $2 billion, and even 3 or 4 years later you go public at $1.5 billion, well, tough shit on the guys who paid $2 billion, but life goes on.
Ramp's raised $1.9 billion, so it's just going to keep consuming this capital for one reason or another, right?
[Speaker?]
And as I say, you can actually work it out if someone had the time. I've heard they're doing roughly $700–$800 million. Interchange is a good slug of that, and you get 2.5% on interchange, so you can work out their total transaction volume. You have an average, probably, of a 15-day rotating balance.
So you probably have 4 to 5 times revenue in terms of floating cash amount. In other words, to do $700 million in revenue, you might have a $3–$4 billion capital requirement because you're floating all these—I mean, you're replacing Amex. You're floating all these guys on their credit cards. So you do need the money.
I mean, I get like 20 emails a week from Brex telling me to deposit more in my account.
Yes.
Jason Lemkin
Maybe it's not a coincidence. I'm constantly getting, “Jason, your borrowing may go down below $2 million. We need money instantly today.” Leave me alone, guys. Just leave me be. I'm fine.
That's exactly right. No, I mean, in the end, fintech companies are fintech, and at some point, you need—
One of the non-negotiables is to have low-cost capital, and at the moment, bizarrely enough, venture equity is lower-cost capital than pretty much anything out there. As Jason said, “2% dilution or get a banking license.” Hmm. I'll do the 2% dilution.
Going back to venture land, CRV raised $750 million. They shrunk the team, and they're not raising their late-stage Select fund. Is this a sign of a more rational venture landscape? Is this a sign of LP appetite being less willing to do opportunity funds? How did you guys think about and analyze this move?
[Speaker?]
I think they do early stage well, and they probably decided the best way to make money is to do the thing you do well, then do it well and keep the message clear. I actually thought it was very smart of them, right?
There are some firms that are pulling off these multiplatform strategies, but it's just a step-function increase in complexity, right? If you can do it—and obviously we all know the names who have—great, you have a multiproduct firm. But if you're going to be marginal at it, the non-negotiable thing is to at least do 1 thing well, right?
CRV clearly decided that rather than muddying the waters trying to do this multistage strategy thing, they would just execute really well on great early-stage investing. So I thought it was probably smart in a world where you just want to have a clean message.
And to your comment on whether it's a sign of wider LP appetite, no, I think what you're seeing is that LP appetite is varied. You can say, “Hey, I'm really glad, CRV, that you focused your message down,” and the next day you can say to Founders Fund, “You've got the most amazing growth fund on the planet. Let me give you another $1 billion.” The day after that, you can say to Elad Gil, “You're just amazing. Let me give you $1.5 billion on your own.”
They're trying to figure it out too, and maybe the takeaway is that the whole industry has changed so much that there's a lot of different ways to play the game. More than anything, I think they want to see that people know what game they're playing and play it well, right? Rather than trying to have envy of someone else's game.
By CRV saying, “Hey, this is what we do, and we're doing it well,” you can say, “Okay, I know what I'm getting from that,” right? Does that make sense? I wouldn't want to—
Yeah, versus keeping it clean. I mean, look, the other thing is that now we're in an age of everyone raising as much capital as they can and deploying infinite capital as startups stay private forever.
Jason Lemkin
But deep down, if you're in it for carry over fees, if you want to get into carry mode faster, I'd rather have 2 $750 million funds split in half, like Founders Fund did, than 1 $1.5 billion fund, right? It's just better for GPs, isn't it? I'd rather get into carry mode faster.
I don't know CRV's results, but they've had some good investments. If they're looking at it, especially some partners who maybe generated more carry than others, they're like, “I'm not in it for $1 million or $2 million a year in salary. I'm in it for big carry checks, and I want to get this thing deployed in 24 months, 30 months,” right?
I know we've lost this over the last 18 to 24 months, but if we look back on all of history, in normal times, you want to optimize your fund size to achieve the maximum carry you can in a given time, right? Then just go raise another. In an ideal world, you might even raise a fund a year, so you could get into carry mode as quickly as possible.
You lose a lot of things. You lose time and other things, but you want to get to carry mode fast. You don't want to leave it all to your grandkids, do you?
Jason, come on, man. Do you regret doing an opportunity fund?
Jason Lemkin
I don't regret it because I'll make money, but it wasn't worth it for me to do the opportunity funds. It's not enough. I'll make maybe 15% more money, but it's not enough money. If I had a $500 million opportunity fund and could deploy it, that'd be different.
So maybe CRV looked at it, and maybe they did some of their deals that didn't make a lot of money. It was a lot of hassle, and they're like, “Hey, I only made 10% or 15% more carry. My LPs don't love it because I burned a lot of capital from them. Let me concentrate where I make a lot of carry.” That's my guess.
And for me, Harry, it's the same thing. Ninety percent of my carry will come from the main fund, so I'm like, “I don't want the drama in my life.” I'll still make maybe 3x, but that's it. It's not a lot of money.
I think that's what the math, interestingly enough, runs out to, because you look at it and you go, “How many deals do you have in your main fund? How many of them are amazing? How much can you get in?” Maybe only 20% of them are amazing. How many of them can you deploy late-stage dollars in? Maybe only half of that, because the late-stage rounds get pricey very quickly.
It turns out that unless you end up with one of the very few companies that are not just amazing but super amazing, where they can be a $20 billion outcome, your ability to deploy lots of capital relative to your early-stage fund is actually much smaller than you think. So the size of the opportunity fund that you can deploy just within your entities is smaller than you think.
And you're right, Jason. Then you end up saying, “Is it worth it?” Now, you can decide, as some people have, “No, I'll build a whole late-stage growth strategy,” and knock yourself out. You can do anything and put billions to work, but then, at that point, you're becoming a different thing, right?
Plus, maybe less discussed, maybe CRV is too big for this, but almost every seed manager that we know that's been successful can spin up an annex fund. It's not a permanent decision to not raise another vehicle. If all of a sudden you got into Anthropic early and it's turning out pretty good, you could raise a couple hundred million in an annex fund or an additional fund.
Do you not think, though, that Benchmark's capping or discipline on fund size is one of the core reasons why maybe they've lost some talent this year, when you look at the likes of Miles or Victor leaving?
I don't know if I agree with the characterization. I think they've had—I mean, Jason did the list, actually. Either you or Jason did the list last, Harry. They've done amazing deals. If being left behind is that set of deals that they've done, I don't think that's challenging.
Jason Lemkin
Right.
But you're both right. You're both right. The names that they've picked—extremely well, right? Incredible investments. At the same time, if you look on social media, Benchmark isn't listed the way Andreessen and Sequoia were a generation ago. It's just not. Does it matter? Harry's built a big brand. He's concerned it matters. You could argue both sides, but when the industry was smaller and Brian Halligan had to drive up and down Sand Hill to get a deal done and it took months, brands were just different, right?
It's still an A-tier brand, but it's not in every conversation on X, right? It's YC, Sequoia, Andreessen—that's it, really.
Do you not think that if you were scaling fund size and scaling strategy, that would have increased the likelihood of being able to keep great talent like Miles and Victor from leaving?
[Speaker?]
I think it's presumptuous.
[Speaker?]
I'm not going to tell Benchmark how to run their business. They've done it. I've been in this business. I remember them starting in ’95 and talking to them. They've done a pretty damn good job of running that business. They don't need my help.
I think it's what Jason said. Stepping back from the individuals, the meta question you're asking is—let's stipulate, because I think it's true—what we're asking is: Is the very best specialist fund able to compete in this market with the very big, full-stack firms? That's really the meta question you're asking.
I'm willing to stipulate, and there's a lot of data that says it, that Benchmark has been among, if not the best, specialist funds. So I think this takes it away from commenting on individuals, which gets personal very quickly, and more toward the meta question: Is the right strategy a specialist fund, or do you need to be a full-stack player to matter?
There's no doubt that if you're full-stack, you have more coverage, you have more news, and you have more news flow. There's also no doubt that—I cited the data from the Rotman guy at DST a while back—your picking goes down a little, but your volume goes up, right?
I think the biggest risk you face as a specialist is that you get crowded out by the noise, and people don't know you're amazing enough. Therefore, you lose some of the at-bats to the people who have more brand. The risk you face as a big brand is that, in your wild urge to put all the money out, you end up overextending yourself, and you get subpar returns.
You fast-forward 5 years, and you look back and go, "Oh, we had lots of noise, lots of good individual deals, but as Jason said, it didn't add up to compelling returns because we had so many other deals." I think the truth is both strategies will work if executed well, and both strategies have their risks. I know that's kind of a stupid answer, and you're right, it is, but I think there's lots of ways to make money.
The one thing you don't want to do is be inconsistent. You have to have a strategy that plays to your strengths and that can work for you, and you have to understand the risks that your strategy entails, including the risk of a specialist strategy. We see it every day. When you're competing against the guys who have infinite deals, infinite deal flow, and infinite money, it's hard, and sometimes you lose, right?
Equally, for those guys, sometimes you put $100 million into something and it just doesn't work. Unless you have an outlier to cover all those mistakes, that's going to be their problem.
Guys, I want to wrap up with one final question. We had Halligan today. He was fantastic. Who would you most like to have as our VIP guest on the show next time?
Rory O’Driscoll
You guys are so much better at this than me because you interview for a living. I don't have an opinion. I thought Brian was an excellent guest because he brought a different perspective to bear as a CEO. He was strong on the things he knew. Obviously, we knew him from the deal.
Both of you have done way more interviewing than me because I do none. So, by definition, you do more. Whoever you two think, I'm totally willing to try. How about that?
I think it would be great to have Marc Benioff. I think he would do it. He'll be different from Brian, right? But my idea that I didn't have until today was Jeff Lawson.
I thought the same. I thought Jeff would be fantastic, dude.
Didn't occur to me until today. I would love to hear all of his reflections, all of his thinking. I mean, he's a founder's founder, and that hadn't occurred to me. It's a great idea, right?
Rory O’Driscoll
And how would we, in fairness to him, not make it just be everything you learned getting fucked up? You want the activist story, but you don't want it to be a celebration.
He's rethinking everything from his stack in the age of AI, right? Let's go for it. I'm going to do Jeff and I'm going to do Benioff, and let's get them on in the next couple of weeks.