Will Wu: Top Five Product Lessons from Creating Snapchat "Discover" and "Chat" | E1111

Will, I am so excited for this. I heard so many good things from many different people, but especially the incredibly good-looking Jack Brody. Thank you so much for joining me.

1. Will’s Tech Journey & Satellite Story

Thanks so much for having me. It’s really a privilege to be here. It’s very, very kind of you.

I wanted to start with your entry into tech first. I like a bit of context, so how did you first get interested in tech and product?

Okay, so we’ll go way back. I was very lucky to grow up in a household just surrounded by tech and science. My dad was an electrical engineer working in the semiconductor business in Silicon Valley, and my mom had a PhD in chemistry.

Growing up, my dad would always bring home the latest computer gadgets. For whatever reason, I was always so curious about how these computers and technologies worked, much to his chagrin. I would get out my tool set, start unscrewing everything, and literally tear apart these computers. Then I would never put them back together, which drove him insane.

I just grew up around computers, and I had a very formative experience when I was around 12 years old. Starting when I was 12 and going through my early teenage years, I discovered something on the internet called IRC. Do you know what IRC is?

No, I don’t, but please keep going.

IRC stands for Internet Relay Chat. I think it was invented in the late 80s, but it was essentially the first ever form of internet chat rooms. As a 12-year-old kid, I would log on to IRC in my childhood bedroom every single night and connect with strangers online.

2. Evan Spiegal's Product Mastery

It sounds a little bit weird, but I met some of the most brilliant people you could possibly imagine. If you think about the types of people who were on IRC in the early 2000s, I can only imagine they were middle-aged computer scientists who had literally invented computers, the internet, and everything else.

They mentored me, and I learned from these strangers on the internet. I literally have no idea who they are, but I learned so much from them about computers and technology. I learned about cybersecurity, cryptography, computer networking, and video encoding.

One of my parents’ favorite stories to tell is that when I was 13 years old, I went on Craigslist and bought a used satellite dish. I was taking guidance and mentorship from the people I was talking to online, and I ended up taking this used satellite dish, crawling onto the roof of my parents’ home, and drilling holes into the roof to mount it.

Then I figured out how to point it at a TV provider’s satellite up in the sky. I ran the cable into the back of my computer to see if I could decrypt the signal.

Technology was my playground growing up. I was constantly exploring different facets of what was possible, out of pure intellectual curiosity, to understand how technology and computers worked. It was magical to me. How is it possible that we’ve created these devices that can do so many things?

3. Snapchat Product Design Experience

We have this innate love of product and technology at such a young age. I was told I had to ask about that, and then I was told I had to ask how you came to Snap. What’s that story?

I think the first half of my life was really about thinking of myself as a technologist and an engineer. I saw my father as a role model. He was an electrical engineer, so that’s what I ended up studying.

I went to school for electrical engineering and then went to graduate school for computer science. I dropped out of graduate school to start a company with some amazingly brilliant people I met there. The company was also about online connection.

I think the formative experience I had meeting all these strangers online really helped me understand the impact that online connection can have. We started a group-messaging app, which was the hot thing to do in Silicon Valley at the time.

One day, a mentor of mine walked into my shared co-working space with Evan, the co-founder and CEO of Snap—or Snapchat, as it was called at the time. This was late 2013, so Snapchat was still a startup, although it was already growing to be very popular. I was already an avid user.

My mentor said, “Hey, Will, this is Evan.” At first, I had no idea who he was. Then I quickly realized that he was the CEO of Snapchat. I got really excited because I was an avid user, and we had a really good conversation. We ended up going to lunch together.

I remember we were getting to know each other and telling stories. I started telling him the story of how, for the original iPhone, I was so excited about the launch that I got all my friends together and we camped out in line at the Cingular Wireless store for 26 straight hours. We were first in line at the store to get the original iPhone.

I told Evan that story, and he got really excited because he loves the iPhone. We high-fived across the table. He said, “I have the perfect job for you.” Later that day, I got a job offer in my email. The job title was “product designer.”

Up until that point, I had always thought of myself as an engineer and a technologist. I looked at the job offer and thought, “What is a product designer?” I literally had no idea what a product designer was. I tried to Google it to understand, but I still didn’t really grasp it.

I’m very appreciative to Evan for helping me see myself as a product person. Up until that point, I had only seen myself as an engineer. He saw what I was doing, what I was building, and the way that I thought. He saw my passion for products like the iPhone, and he helped me see myself in a new light.

You worked with Evan on product for many years. How many years was it in the end?

Nine years and 2 months, according to LinkedIn.

What makes him so good at product?

Evan has an unbelievable product instinct. He’s so quick at understanding social interactions between humans and what makes a beautiful design. He has really strong values when it comes to product. He’s instilled the way he sees the world and the values he has into Snapchat.

He’s also an amazing storyteller and communicator. Part of being good at product is communicating your ideas and your vision, and he’s very inspiring in that way. I consider him a lifelong friend of mine. He’s a brilliant product thinker.

4. Building Discover on Snapchat

You worked on, and were central to, many different elements of Snap that are so loved today. Let’s start with Discover. What are the biggest lessons you have from being so central to Discover?

One of the biggest lessons from Discover was that it’s really important to understand the traffic patterns of how people are using your app.

We spent more than a year building Discover, designing it painstakingly, and creating and pursuing the vision we had for it. Then we launched it, and it was hidden off in the corner of Snapchat. The way the app was laid out, it was essentially at the very right of Snapchat.

Ironically, it was pretty hard for our users—our Snapchatters—to discover Discover. It was an intense launch because we had built up all this hype around it, and many of our media partners were really excited. Then we launched it, and people weren’t discovering it.

What we ended up doing was a very small design tweak. We moved Discover one screen to the left, essentially putting it on the same screen where you saw your friends’ Stories. That completely changed the fate of Discover. It made it easy to discover Discover, and it helped me understand the importance of thinking through the ways people are using your app or product today.

You have to think through how to gracefully expand your product feature set by putting additional functionality into the right portions of your user interface.

That totally makes sense. I love the challenge of discovering Discover. The meta-problem there is quite hilarious, to be honest.

5. SnapGaming Platform Insights

Another element you worked on, which is crucial as well, is the gaming platform. I think a lot of people don’t actually recognize that. I heard about trips to Australia, which we can get into later, but what are the biggest lessons from working on Snap’s gaming platform?

Snap Games was one of the most valuable experiences I’ve ever had. I learned a lot from it. I got to meet some incredible people, and I saw that the game developer community is global, vast, diverse, and incredibly creative. I think some of the best product thinkers actually come from game design.

For me, the biggest lesson from Snap Games was very personal: learning and building the confidence and courage in myself to overcome challenges. I was in my 20s, and I had never managed a team before. I had never acquired different companies in pursuit of a vision.

I remember the launch of Snap Games being quite chaotic. It was one of the most stressful periods of my life. We launched it with a grand keynote on stage. It was the first-ever keynote for Snap, and I was speaking in front of thousands of important people.

Public speaking really terrifies me. I had never spoken to a reporter or journalist before, and my first time speaking to one was actually speaking to a whole room full of prestigious reporters. They were all cross-examining me.

All of this was happening while we were simultaneously trying to launch a crazy new product on unproven technology, in partnership with five different game developers from different continents and time zones around the world. I wasn’t eating or sleeping very well.

It gave me a lot of confidence because, at the end of the day, I persevered through it. After getting through that, I thought, “Wow, I can get through a lot more than I thought.”

It gave me more courage to challenge myself, and it made me start to realize that imposter syndrome—which I’ve felt my entire life and still feel to this day—can be a good thing. It used to terrify me, but now I intentionally put myself into uncomfortable situations that trigger imposter syndrome because it means I’m pushing myself to learn and grow.

6. Product Design: Art vs Science

I totally agree with you. I’ve always felt it, having not been educated and being a venture investor. I think I must be the only one.

People can often feel imposter syndrome when they’re thinking about art versus science, and product in particular. They lean on data and science because they’re afraid of their own conviction or courage, as awful as that sounds. Is product art or science? How would you answer that question? If you had to put a number on it, where would you place them?

I believe product is equal parts art and science. I’m beginning to build a new team here at Match Group called ASL, and it has 2 meanings. One meaning is Art and Science Lab, which reflects my belief that the most innovative and best products happen at the intersection of artistic disciplines and scientific or technological disciplines.

It’s a dance between the 2. You need to bring people from multiple perspectives, backgrounds, and trains of thought together to swarm around solving problems for people in order to create really innovative products.

As a product leader, in addition to making sure the team has people with art and science backgrounds, I think you need to take both an artistic, intuition- and instinct-driven approach and a scientific, data-driven approach when you’re developing and growing a product over time.

Sometimes you have to lead with your instinct. When you’re taking a product from 0 to 1, no amount of data or market research is going to tell you exactly whether it will work. You have to take a leap of faith.

Often, when you’re iterating beyond that, you can use data to inform your instinct and determine which direction you want to go.

Speaking of that intersection, and the subconscious that you mentioned, you’ve spoken to me before about the importance and focus of human-centered design. I didn’t really understand what you meant, to be honest. Before we dive in, what is human-centered design at its core?

Human-centered design is keeping your end users—humans—at the forefront of your mind through every step of the product development journey. That starts with the very early stages of ideation and need-finding, building empathy for your customer, and continues through development, prototyping, showing prototypes to users, getting their feedback, iterating, launching, and so on.

It’s really just keeping the human at the forefront.

Where does human-centered design most often get lost?

7. Execution Speed & Product Reviews

I think it can get lost if you lean on data too much. A signal in the data might tell you to do one thing, but if you don’t stop and think about how that feature change might impact your end users, how they feel, or how it might impact the problems you’re solving for them, you can lose sight of your customer.

At the end of the day, you can end up going down a path that might have long-term detrimental consequences.

8. Human-Centered Design & Apple Watch

Are there products that you think do this brilliantly today, and products that do it badly, to bring this to life for us?

The Apple Watch is a fantastic example of a product that I assume was made with a human-centered design approach.

Human-centered design is about identifying problems that humans—your users and customers—are having and figuring out how to solve them through a blend of art and technology. The Apple Watch is an incredible product. Look at how ubiquitous it has become over the last few years.

For elderly people, for example, it’s a problem in old age that if you have a fall, it can have long-term, detrimental health consequences. It’s incredible that the Apple Watch can use its accelerometers, motion sensors, and other technology to detect these falls and notify emergency services.

Even looking at the most recent Apple Watch announcement, I think the feature is called Double Tap. Apple saw that there was a problem with using the Apple Watch. On every Apple Watch up until that point, you couldn’t tap the screen to hit a button if you were holding a cup of coffee or walking the dog with a leash.

They invented a feature through a blend of intuition, instinct, art, and science that lets you double-tap the fingers on the same hand where you’re wearing the watch. It hits the primary action on the watch.

It’s another example of human-centered design: looking at the problems your users have and figuring out how to solve them.

Who does this badly?

I don’t know if it’s fair for me to bash anyone. The first thing that comes to mind—and I should caveat this by saying that I understand it’s a phenomenal product—is Concur.

Of course I know Concur. It’s terrible.

I’m glad it’s not just me. It serves a different type of customer, so it’s really good for an enterprise. It’s an enterprise SaaS product, and it can be successful because it solves the right needs for an enterprise customer—the company they’re selling to.

I don’t know if it was designed from the ground up with the end user in mind.

It’s like Bill.com. I always think, “Do they have anyone in product?”

It’s a different product mindset and philosophy. Enterprise product is very different from consumer product, which is where I normally focus my energy. That’s where I think the human-centered design approach really matters.

9. Identifying Your Target User

When we talk about the human-centered design approach, break it down for me. If I’m a founder listening to you and I want to do it, what is your approach?

Identify your target users—the people you most want to use your product—and build empathy for them through whatever means necessary. You can get really scrappy. If you’re an early founder or entrepreneur, you can talk to people on the street.

What questions do you ask to uncover user needs? It’s hard for me. The first thing that comes to mind is that I’m at Match Group, thinking about how to continue to spark online connection around the world. What’s your approach to dating?

If you were trying online dating for the first time, which apps would you consider? If you’ve already gone through online dating, what are some of the struggles and challenges you’ve had?

You basically want to hear about the problems people have. Someone might say, “Getting started with online dating is really challenging. There are tons of different apps to choose from. How do you know how to make a dating profile?”

It can be awkward to figure out how to represent yourself with photos and text online in front of potentially millions of strangers in a romantic setting.

10. Simplicity in Product Design

You listen to their problems, formalize those problems, write them down, and then bring together smart, creative people from different backgrounds—people with art and science backgrounds—to think about how to solve those problems.

You mentioned creating profiles. Is simple always better when it comes to product design? Some profiles are simple, and some aren’t. Is simple always better?

It’s not always better, in my experience. When you’re creating a novel product that people don’t yet understand, something that’s truly innovative and new, simplicity is paramount to making it easy to use and easy to grow.

I think about the original iPhone, for example. It was actually very simple. Apple used user-interface design patterns like skeuomorphic iconography to ground people’s understanding in real physical analogies.

Over time, iPhones have become much more sophisticated. They’ve added feature after feature. That can work because if you start simple, you have a core product. If you’re lucky enough to find product-market fit, you have a simple core product that people can easily pick up and understand.

Once you’ve captured their attention and found product-market fit, you can take them on a journey over time. You can layer in complexity and push the boundaries of what the design language can do in order to introduce new features and complexity that solve users’ problems in entirely new ways.

How do you prevent feature creep? It’s so easy over time to add more and more, and then you look at the product and think, “That’s cumbersome.” How do you retain simplicity over time?

This is where I think there’s a lot of art involved. You have to think through the right level of abstraction for features.

You don’t want to open an app and see hundreds of toggles, settings, and switches. It’s overwhelming, confusing, and hard to understand. You do want to make some of those settings and toggles available for power users who want to push your product to its limit.

It’s about figuring out, from a design perspective, what the information architecture should look like and how to tweak the interface so it’s approachable for a layperson but has depth for a power user.

How do you strike that balance?

Through a lot of iteration and experimentation, coming up with hundreds or thousands of different mock-ups and designs.

I’m a huge fan of rapid prototyping—not just creating interactive Figma mock-ups that you can click through, but actually prototyping with real software code. That lets you rapidly experiment and feel things out using your intuition and instinct. You can also conduct user studies and figure out whether it’s approachable for a layperson.

I was speaking to Pony before the show.

Pony?

Yes, Pony. He told me about a time when the team wanted to ship a product that was a little bit rough and creaky, and you said, “No. Just no, guys. That’s not going to happen.”

How do you think about speed of execution? Is good today better than perfect tomorrow?

I can sometimes be known as a stickler for design details. I think that comes from working with a product team in pursuit of a vision. You want to put a product out there that you can be proud of.

First impressions really matter, whether it’s the first impression for your target customer or for reporters. When you’re launching something brand new, it can’t be perfect. Perfection takes forever, and if you try to build perfection and launch after several years, you might find out that it doesn’t solve a real user need and have to start all over.

You should at least launch something you’re really proud of—something that reflects and is emblematic of the vision you’re trying to achieve.

Does that go against rapid prototyping? You might say, “Quick and dirty. Does this work? Do you like it here? Do you like it there?” Do those ideas conflict?

I think rapid prototyping is a critical tool for any product person to accelerate the path toward putting something on the market that they’re proud of.

It allows for rapid iteration and guidance by intuition and instinct within your internal team—among people who share the vision of what you’re trying to achieve. It also allows you to do informal user testing. You can hand a rapid prototype to a friend or a target customer and see what they think.

11. Inspiring Creativity in Teams

It’s actually quite complementary to the idea of getting a product that you’re proud of out there.

We see what they think, and then we have a product review. I’m not in the product world, and a lot of CEOs aren’t either, so I want this to be a lesson for them. When we think about product reviews, how do you conduct them? What makes a good one versus a great one?

I have a few different types of reviews, and I don’t know if you’d bucket all of them under a product review. I think the environment for a brainstorm is also extremely important.

For a product review, I would start by asking: are we in person or remote? Do we have a whiteboard or a Miro board?

I don’t even know what that is. It sounds amazing.

You don’t know Miro? It’s a collaboration tool.

I haven’t seen that, or maybe I have but haven’t seen the name.

It’s for designers and product people to design together.

Got it. You learn something new every day. I love it. I’ll have to check it out. I guess I’m old-fashioned—I like a whiteboard.

I think that when it comes to creative brainstorming and design brainstorming, being in person is of paramount importance. Your physical setup is extremely important.

I like to create a relaxed atmosphere where you’re on a couch and can be casual and conversational. I also like to create a safe space where people have the psychological safety to throw out crazy ideas.

I’ve often found that wacky ideas, which are almost like half-jokes, can have an important edge. At the end of the day, they can turn into an amazing idea or product feature.

You cap the number of people at a certain point. How do you determine whom to invite? I’m intrigued to really understand the bare bones of it.

It’s important to have a small group because otherwise you get into a situation where there are too many cooks in the kitchen. There are too many people who can shoot down ideas, which I think is the worst thing when it comes to creativity.

Shooting down ideas is something I try to avoid in the product culture I create. Any idea can have merit if you look at it through the right lens.

I try to cap it at maybe 5 people maximum. That’s a rough rule of thumb, but I think it’s important that they’re people you trust and understand how to work with. You’re all coming at a problem from different perspectives.

Maybe someone is formally trained in product design, or maybe someone is an engineer who can think about the problem from a different lens.

Do you set an agenda beforehand?

I have in the past. Setting an agenda can be important, but sometimes too much structure can stifle creativity.

It’s a constant tension or struggle I face internally. Some of the most creative ideas can arise from chaotic environments, but you also need some level of structure to keep people on task.

How do you bring chaos to an environment? I’m a rebel and a rule-breaker, which is why I never went to college. My mother still thinks I’m doing something on the internet when I arrive with Chanel, and she still doesn’t know what I do.

The fund helps, I have to admit. I’m sure she tells everyone I’m a hedge fund manager. Not quite, Mom, but close enough.

12. Product Team Culture & Hiring

How do you bring chaos? How do you inspire creativity and say, “Let’s actually think outside the box here”?

2 things come to mind. The first is bringing together people from diverse backgrounds and perspectives. I can’t underscore enough how important that is.

You want people thinking about the same problem—the same human need you’re trying to solve—from totally different perspectives. Whether it’s engineering, fine art, graphic design, fashion design, architecture, or something else, bringing those perspectives together helps you analyze a problem in a different way.

The other thing that’s important is inspiration. Travel around the world, see your target customer in the flesh, and observe the way they’re interacting with the world. Understand their environments in a really nuanced way.

Getting the right creative inspiration is paramount to generating that chaos and coming up with the right ideas.

What’s really hard, though, is when you’re the product leader and you have revenue generation today but innovation for tomorrow. How do you balance investing in what makes money today and making sure that machine keeps humming, while also keeping an eye on generative AI and new ways of creating profiles that are seamless and require no effort?

You need both. You need revenue to support the business, but you also need to innovate and push your product forward to stay ahead of the competition.

In my experience, the best approach is to have 2 separate teams dedicated to those independent goals: one team dedicated to revenue generation and another dedicated to innovation.

There’s often a strong tension between the 2. When you’re building a product, you might have to deteriorate your revenues with a new feature in order to experiment with an innovative new idea. If the same team is making those decisions, that conflict of incentives can paralyze development.

Do those separate teams need to work together, or are they clearly distinct?

They definitely have to work together. That’s part of the role of a product leader: properly balancing the needs of those 2 teams.

You have to create the right communication pathways and processes for the teams to collaborate, share notes and ideas, and build a culture of openness and information sharing.

13. Multiplayer Gaming: Crash Club

You also want people from the 2 teams to get to know one another personally so they can build trust as humans. That way, they aren’t just thinking about the opposing ideas and directions they have.

What mistakes do product teams make when it comes to culture? How does product culture go bad?

I like to create a culture where everyone is growth-minded and practices humility, empathy, and listening to one another.

What I don’t like is when you have people who are egocentric and driven by ego—people who think they know everything. That can be poisonous to team culture. It can stifle the voices of other people in the room and plant seeds that tarnish the rest of what you’re doing over time.

I think a lot about team culture and how every person is like a seed in your team. Those seeds blossom into trees over time, so your team is like a field of trees.

If you have the wrong people on the team, it can be like a parasite that grows over time. You have to get rid of it quickly.

What a wonderful floral analogy. I’m glad you’re taking on the natural analogy.

It doesn’t work out, then who knows? You need to change the voice a little bit. He has too much hesitation in his voice.

14. Traits of a Top Product Designer

I totally agree with you on the importance of culture, but that comes down to hiring and getting the right people on board. It’s really hard to hire great product people. You’ve done it very well at Snap, and you’re doing it again at Match.

Before we talk about the people, how do you structure hiring for product? What does that process look like? I’m an angel investor and I’ve never done it before. How do I hire product people?

I specifically look at products that people have designed or built in the past. Someone’s actual work—the products they’ve created, or at least imagined—speaks volumes more than you can extract from a few interviews.

It speaks volumes about the way they think and communicate their ideas.

What do you want to see in the products they’ve built?

15. AI's Impact on Product Design

It depends on the product. When I was first building Snap Games, this goes back to the Australia comment you made earlier, I had a crazy vision of creating multiplayer games in Snapchat that were fun, vibrant, and colorful, and featured your Bitmoji. You could play as your Bitmoji in Snapchat with your friends.

Snap didn’t already have game-development expertise within the company, so I started looking for game studios around the world that we could potentially acquire through M&A to bring that expertise into the company.

I found a game that really spoke to me. It was multiplayer and real-time, incredibly fun and colorful, and the music had the right energy. It was made by the same creators as Fruit Ninja. The game was called Crash Club, although I don’t think it’s on the App Store anymore.

The user interface for the game menus was a 3D box that you could swipe and tap. The box would spin around in 3D. It was a novel approach to UI interaction design.

Before I had even met the developers, I thought, “This is the game studio we need to acquire.” I found a way to connect with them, and we had an introductory call.

At that point, I was already sold on their product abilities and game-creation abilities. I was really looking for whether we were a good culture fit—whether we got along and had personalities I would want to work with over time.

They were in Australia, and I was in Los Angeles. We had 1 call, I confirmed my suspicion, and I immediately flew to Brisbane the next day to pitch them on Snap buying their game studio. It happened incredibly quickly.

Getting back to your question, it depends on the product you’re trying to build. If you have a certain vision for the kind of product you want to create, you’ll see the right person. You’ll know it when you see what they’ve done in the past.

16. Keeping Match Relevant in Dating

What are the single best qualities you look for in a product designer? You mentioned the design of the 3D shapes and the spinning. What are the best qualities in product design?

Whether it’s a designer, an engineer, or a product manager, I’m looking for people who are very growth-minded.

What does that mean? I’m pushing you on that.

Someone who is open to change, adaptation, and learning. Someone with the innate intellectual curiosity to understand the way the world works and improve their abilities.

How do you test that in an interview?

When I hire anyone, I always ask about their long-term career ambitions. I want to understand how much thought they’ve put into their end state and what their end game really looks like.

I want to make sure that their end game is something I can support and that I can hopefully help push them along that journey over time.

What do you not want to hear in that 10-year plan?

I wouldn’t say there’s anything I don’t want to hear. I believe in striking a work-life balance, but at the end of the day, I’m looking for someone who’s really passionate about their craft and whatever they’re doing.

Passion drives people to work beyond 9 to 5. You have to understand people’s motivations. Why are they interviewing with you? What are their career ambitions? What are they looking for?

What do you think product people care about today? I think people’s shift has been very real. They say they care less about money than ever before and more about mission. They say that because they think it’s more moral, but they actually care about work-life balance much more than anything else.

The pandemic helped people realize that maybe you don’t need to be in the office 5 days a week—or, even worse, 7 days a week.

Having some flexibility is conducive to a better work-life balance and perhaps even to being a better teammate and employee because you can bring your full self to work under the right circumstances.

I don’t know if people aren’t looking for money. This is something that concerns me about product management as a discipline today. It feels like a sexy, trendy job in tech that has an allure because it’s known to be high-paying.

I try to weed out people who might only be interested in product management for reasons like that.

Cash?

I mean, speaking to a venture investor, your job is probably sexier than product management.

We get paid.

Product managers get paid pretty well, I think, at least at certain companies where it’s a highly valued function. It is a cool job. You’re the CEO of the product. That’s how most people describe it, and that’s kind of cool.

Do you use case studies in the interview process? If so, how do you think about using them?

I don’t personally. I’ve always felt that they can be too artificial and forced. I think of a case study almost like a standardized test.

When I was going through college and studying for internship interviews, it was all about brain teasers. It’s a certain type of test of someone’s thinking, but if someone isn’t good at brain teasers, they can still be good at many other things.

I don’t take a very structured approach to case studies, brain teasers, or anything like that in interviews.

Do you know pretty quickly when someone is good?

I think I do. I’d like to think so. I look at what they’ve done and what they’ve built. Even if they’re early in their career, I look at concepts they’ve created and ask them about those concepts.

I’ll ask, “Why did you put this button here?” or “Why did you use this specific copy or string of text in the user interface?” That gives me an understanding of how they think and how passionate they are about product.

What have been your biggest hiring mistakes? For me, one is when someone comes from a great brand. I think, “They came from Jack’s product team at Snap, so obviously they must be amazing.” Then they’re not.

Another is when I think someone is incredibly innovative, but they’re not a good culture fit and I didn’t take that into account. What have been your biggest mistakes in product hiring?

For me personally, I can get overly invested in people. I can give people a lot of room to fail because I like to see the best in people. I’m a glass-half-full kind of guy.

My friends give me a hard time about this because I tend to like everyone, even people most people severely dislike. I love them because I see them for who they are and think they bring something special to the world.

That sometimes means I give people a long leash. I may need to read the signs from the team earlier to figure out that someone isn’t a great culture fit or isn’t very passionate about our mission and is only in it for the money.

Is it wrong to be in it for the money? I know founders who have created companies and are just there for the cash. Does it matter, especially for product people, if someone says, “I’m here for the money you’re paying me, but I’m really good at what I do”?

I think it matters. I don’t like the idea of a paid mercenary who’s only in it for the money.

Product can be a high-earning job, but I think the most profound and innovative products come from a deep passion for creating something that can have an impact.

Do you like people who have already had experience in that space?

Not necessarily. It can often be valuable to bring in people with a different perspective, so they can think through a certain type of product or feature from first principles, using the expertise and unique perspective they bring.

I totally agree. I think it’s especially valuable in gaming. I love hiring people from gaming into non-gaming products.

Exactly. When I got to know the game-development community, I encountered some of the most brilliant product thinkers in the world. I had no idea.

I totally agree.

I want to talk about the future, and then we’ll do a quick fire because I’ve roamed around. We have to talk about the impact of AI first. How does AI change the actual process of product creation and design?

As a product designer or product manager, I think AI has already created a number of tools we can use to become more effective.

Some product designers on my team are already using tools like Midjourney and DALL-E to come up with different UI concepts or visual concepts.

I’ve also been experimenting with large multimodal models, or LMMs. They can work with language, like ChatGPT, but they can also see images and photos and analyze and understand them.

I think there will probably be an AI tool in the near future that gives you instantaneous user feedback and testing. You create a mock-up or prototype and hand it to the AI, saying, “Give me feedback on this new experience as if you were an 18-year-old male living in Los Angeles,” or “as if you were a 55-year-old woman living in New York.”

I’ve already started playing with some of these LMMs in this way, and I think that capability is right around the corner.

Understanding how to use the latest AI tools will be important to making sure you have the right tools at your disposal to do a good job.

When it comes to product design, it’s also important to understand the capabilities of AI. I think AI is going to change every facet of life as we know it over the next few years. It’s important to understand the capabilities and limitations of the technology and figure out how to weave it gracefully into your product design so you can stay relevant.

Many people on the show have said that, in the world of AI, with the impact it has on product and user interfaces, UI will become completely irrelevant and be replaced by a bot. Do you agree, or is that overly simplistic?

I don’t agree with that at all. AI is an overloaded term these days. Right now, when we think of AI, many people are talking about large language models like ChatGPT.

What’s amazing about ChatGPT is that it opens up an entirely new paradigm of human-computer interaction. In theory, we no longer have to interact with computers through user interfaces and buttons. We can just talk to computers.

That’s powerful. My mom is in her mid-70s, and she didn’t grow up with mobile phones or with understanding how to navigate mobile interaction and user-interface paradigms. She isn’t very good at using apps on her iPhone, but she’s really good at talking.

It’s incredible to me that something like ChatGPT can enable an entirely new mode of interaction with computers.

I don’t think previous human-computer interaction paradigms are going away. Look at the command-line interface. It was one of the original ways to interact with computers, and people still use command-line interfaces today.

The graphical user interface on a desktop computer also still exists. Even though we have incredible multi-touch interfaces on our phones, people still use graphical user interfaces on their PCs, and they still use command-line interfaces.

In the same way, I think people will continue to use interfaces on a screen, laptop, or phone, even in a world where talking to a computer through a large language model is pervasive.

I totally agree. I can’t wait for my mother to be able to use a piece of technology at all. She still calls it Google “Goggle,” so it will be a relief if she can talk to her phone and give me a break.

I’m all for it. It’s going to be incredible.

Generative AI: I’m a venture investor, and we love a bit of generative AI. Is it worth the hype?

I do think the hype is warranted, but I wouldn’t invest in every generative-AI company that comes across my radar.

There are a lot of entrepreneurs with great ideas for applying something like ChatGPT to a new application. But if they’re essentially just prompt-engineering on top of the same large language model everyone else has access to, I worry about their long-term defensibility.

Fundamentally, though, I do think the hype around generative AI is warranted. Going back to the shift in human-computer interaction paradigms, it allows us to interact with computers in an entirely new way.

On top of that, these large language models are trained on much of the world’s information and data. It’s incredible. It’s like true intelligence—democratizing access to intelligence over time.

As the cost of accessing these systems and the cost of inference get cheaper, they can reason across multiple domains, whether that’s human history, science, or medicine.

It’s incredible to have an intelligent system at your fingertips that can access so much of humanity’s knowledge.

If you think about Match, unlike Snap, where great champions use Snap more, if you have a really successful Match user, they say, “Thank you for finding me the love of my life. I’m off now.”

I think it’s beautiful. This is what wakes me up every day, to be honest. It’s thinking about the impact we can have at a global scale on real people around the world.

It’s a major success for us if we never see someone again because they found a relationship they’re happy with for the rest of their lives. I think it’s amazing.

It’s a little strange and something I’m still getting used to, because if we’re successful, we lose users. A lot of our job comes down to making sure we can capture the next generation of users—people who are just coming of age and beginning to think about dating and sparking romantic connections.

Dating apps are competitive. What I mean is, people have 4 or 5 of them. When I had dating apps and was single, I had 5. It wasn’t as though you used them to be as successful as possible. Do you know what I mean? Are you actually competing?

I think about it more as collaborating, frankly. It’s about partnering with other apps and brands, many of which are within the Match Group portfolio.

You’d say your competition is games?

Are you asking where I go on dating apps?

Mostly when you’re on the L—when you’re on public transport in the UK, such as trains and buses, or in Ubers.

I wouldn’t say it’s dating apps. You’re competing against other casual games. Everyone has only 24 hours in a day, and only a certain number of those hours are spent glued to a mobile phone.

Hopefully people aren’t always glued to their phones. Hopefully they’re out in the real world interacting with people in real life.

So, yes, I think you’re competing for time—your share of mind. Whether it’s gaming, TikTok, or something else, there’s a finite amount of time in the day. At some level, every mobile app has this issue.

I totally agree. I always say we’re competing against Taylor Swift, which makes me terrified.

A formidable competitor.

You’d choose Taylor over me every day.

17. Quick-Fire Round

I want to move into a quick fire. I’ll give you a short statement, and you tell me: when do you listen to users, and when do you ignore them and say, “We’re sticking to the product roadmap and what we know”?

Listening to users is normally extremely important. The one exception might be when something users are asking for conflicts with one of your core product values.

Even then, I don’t think you ignore them. You listen and understand what they want, then figure out how to solve the problem they’re having in a way that adheres to your values.

What’s your work-from-home setup? I was told you have a special setup. Give me the wisdom.

I went a little crazy during the pandemic. I have an Apple Pro Display XDR. I iterated through a few cameras, but at this point I have an Insta360 Link, which is an incredible webcam on a gimbal.

I have a custom keyboard. I’m a huge nerd. Growing up on IRC, I have a Leopold FC660C keyboard with Japanese Topre switches in a custom housing made by Ryan Norbauer, an artisan keyboard case maker in Los Angeles.

I also have a Logitech MX Master 3 mouse. I swear by that mouse. I could do an entire podcast on my work-from-home setup.

You’re a totally normal guy. Don’t worry.

Totally normal.

What would you say is the biggest mistake founders make when hiring product teams?

Not getting rid of poor culture fits quickly enough.

What’s the first sign?

It can be a lot of different things. You see the way someone treats another coworker. If they aren’t kind, if they have an ego, or if they think they know everything, those can be signs.

Those are the things that can deteriorate the culture you’re trying to build over time.

What 1 piece of advice would you give to a product leader starting a new role?

Get reps in building products. No matter what it is, build something—even if it’s a personal project on the side. Getting those reps in is really important.

Embrace imposter syndrome. Imposter syndrome is a good thing because it means you’re growing.

What’s the watch collection? I want to hear about your watch collection now.

I’ve been obsessed with watches since I was a little kid. I have a drawer full of all the watches I’ve ever owned in my life—my old G-SHOCK, my Nike watch, and Swatches from growing up.

More recently, I’ve been exploring all different types of brands, and I just love watches. They’re an amazing blend of art, science, and technology.

I love how they’re a form of self-expression. I also love how they’re anachronistic. At a time when we’re surrounded by digital computers, having a mechanical watch with a heartbeat of its own—whose heartbeat, as long as you’re wearing it, beats in unison with your heartbeat—is incredible.

I totally agree, especially in terms of the heartbeat. I also think, in terms of marketing, that the heritage of being passed down through generations is fascinating.

The different social capital attached to different styles, and the idea that what you wear is who you are in some respects—do you know what I mean?

I know exactly what you mean. Every day I look at my watches and think, “Who do I want to be today?” It’s an incredible form of self-expression.

I’m also a sentimental person. I love how you can get a watch to celebrate or commemorate a milestone in life. For the rest of your life, whenever you wear that watch, you think about and feel nostalgic for that milestone.

I think it’s really important what watches can symbolize.

We could change it to a pat on the back. It doesn’t have to be for life; it could be for your birthday.

Sadly, no mother or girlfriend has ever done that for me.

Final question: what recent company or product strategy have you been most impressed by? What have you seen another company do and thought, “That’s impressive”?

I have to give a shameless plug to one of our own companies, Tinder. They’ve been working on a new AI feature that lets users quickly surface the best photos from their camera roll, all using AI in a privacy-safe way.

When I first signed up for Tinder years ago, I remember thinking that it should be possible to create an AI model that predicts which photos already on your phone will perform best on Tinder. You could train that model on the high-performing photos on Tinder.

That’s pretty good. It’s the best girlfriend you could have.

I think it could solve a huge user problem that I felt when I first signed up for Tinder. I didn’t know how to choose the best photos of myself, and I hate photos of myself.

It took me weeks to figure out the right photos to put on my profile when I first made one. Being able to do that almost instantaneously could be a real friction remover.

I totally agree. I love that as an example. That’s one hell of a model if it can predict which pictures will convert best.

I’ve loved this. I heard so many great things from Jack, and I’ve wanted to do it for a long time. Thank you so much for putting up with my wayward questions.

Thanks so much, Harry. It’s been a pleasure.