Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20Product: Top Five Product Lessons from Creating Snapchat "Discover" and "Chat", How to Hire the Best Product Talent and Why Case Studies in Interviews are not Helpful & How AI Impacts the Future of Product Design with Will Wu, CTO @ Match Group About this episode Will Wu is the CTO @ Match Group, the owner and operator of the largest global portfolio of popular online dating services including Tinder, Match.com, OkCupid, and Hinge to name a few. Prior to Match, Will was VP of Product at Snap Inc. As the 35th employee, Will spearheaded the creation of Snapchat’s “Discover” content platform. He also led the creation and growth of the “Chat” messaging feature, which today is a primary Snapchat engagement driver that connects hundreds of millions of people each day. In Today's Episode with Will Wu We Discuss: 1. The Journey to Snap CPO: How did Evan make his way into the world of product and come to meet Evan Spiegel? What are 1-2 of his biggest takeaways from his time at Snap? What does Will know now that he wishes he had known when he started in product? 2. How to Hire Product Teams: How does Will structure the interview process for new product hires? What are the most telling questions of a candidate's product skills in hiring? What case studies and tests does Will do to assess a candidate? What are 1-2 of Will's biggest hiring mistakes in product? 3. How to Do Product Reviews Effectively: What are Will's biggest lessons on what it takes to do product reviews well? What are the biggest mistakes product leaders make in product reviews? How can teams drive focus in product reviews? What works? What does not? 4. Product: Art or Science? How does Will balance between gut/intuition and data in product decisions? Is simple always better in product design? What is human-centered design? How does it impact how Will approaches product?
Transcript 10,754 words · 3 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 Evan has got an unbelievable product instinct, just so quick at understanding social interactions between humans, understanding what makes a beautiful design. He's got really strong values when it comes to product. I mean, he's instilled the way that he sees the world, the values that he has into the company. Part of being good at product is communicating your ideas and your vision. And he is just a very inspiring product figure. He's brilliant.
0:26 Harry Stebbings? This is 20 Product, the monthly show where we sit down with the world's best product leaders to discuss how they approach product, design, product management and more. Joining me in the hot seat today, we have Will Wu, CTO at Match, the owner and operator of the largest global portfolio of popular online dating services, including Tinder, Match.com, OkCupid and Hinge, to name a few. Prior to Match, Will was VP of Product at Snap. As the 35th employee, Will spearheaded the creation of Snapchat's Discover content platform. And he also led the creation and growth of the chat messaging feature that today connects hundreds of millions of people each day. But before we dive into the show today, imagine shipping new webpages in weeks instead of months,
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3:24 Speaker 02 You have now arrived at your destination.
3:27 Harry Stebbings? 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. So thank you first so much for joining me.
3:36 Speaker 00 Thanks so much for having me. It's really a privilege to be here.
3:39 Harry Stebbings? Very, very kind of you, but 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? Let's start there.
3:47 Speaker 00 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. My mom was a PhD in chemistry. Growing up, my dad would always bring home the latest computer gadgets. For whatever reason, I was just always so curious about how these computers and technology worked. So much to his chagrin, I would like tear them apart. I would get out my tool set and like start unscrewing everything and literally tear apart these computers. And then I would never put them back together, which just like drove him insane. And I had a really Formative experience when I was around 12 years old, where I discovered on my computer on the internet,
4:32 Speaker 00 what's called IRC. Do you know what IRC is?
4:35 Harry Stebbings? No, I don't, but please keep going.
4:37 Speaker 00 Okay, alright, so IRC stands for Internet Relay Chat. And it is essentially, I think it was invented in the late 80s, but it's essentially the first ever form of internet chat rooms. So as a 12-year-old kid, I would log on to IRC in my childhood bedroom every single night, literally, and connect with strangers online. And it sounds like a little bit weird, but I met some of the most brilliant people you could possibly imagine. Because if you think about the types of people that are on IRC, and this is in the early 2000s, I can only imagine there were these like middle-aged computer scientists who had literally invented computers and the internet and everything.
5:19 Speaker 00 So they mentored me and I learned from these strangers on the internet. I literally have no idea who they are. I learned from them just so much about computers and technology. I learned about cybersecurity and cryptography and computer networking. And my parents' favorite story to tell is that when I was 13 years old, I went out on Craigslist and I bought a used satellite dish. And I ended up taking this used satellite dish, crawling up onto the roof of my parents' home, and literally drilling holes into the roof to mount this satellite dish. And then I figured out how to point it at a TV provider's satellite up in the sky. And then I ran the cable into the back of my computer to see if I could decrypt the signal. So technology was like my playground growing up.
6:03 Speaker 00 I was just constantly exploring different facets of what was possible. And it was just to understand how technology and computers worked, because it's just magical to me. It's like, how is it possible that we've created these devices that can just do so many things?
6:17 Harry Stebbings? Okay, so we have this innate love. I love that in terms of climbing onto the roof, also terrified for health and safety reasons. Your parents must be going, "My word, he needs to find some more friends." But I'm kidding. So my question is, 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?
6:37 Speaker 00 So basically, I think the first half of my life was really thinking about myself as a technologist, as an engineer. I saw my father as a role model and he was an electrical engineer. So that's where I ended up studying. And then I had gone to school in electrical engineering and ended up going to grad school in computer science and dropped out of grad school to start a company with some amazingly brilliant people that I met there. And the company was actually also about online connection. I think this formative experience that I had, meeting all these strangers online when I was a kid, really helped me understand the impact that online connection can have. So I started this company. We were building a group messaging app, which was sort of the hot thing to do in Silicon Valley at that time.
7:20 Speaker 00 One day, a mentor of mine walked into my shared coworking space with Evan, the co-founder and CEO of Snap. This was in, this was in late 2013. So Snapchat was still a startup. It was already growing to be very popular. I was already an avid user. My mentor was just like, hey, Will, this is Evan. And at first I had no idea who he was. And then I quickly realized that he was the CEO of Snapchat. I got really excited because I was an avid user. He and I just had a really good conversation. So we ended up going to lunch together. I remember we were getting to know each other, telling stories. And I started telling him the story of how, I remember I was so excited about the launch of the original iPhone, that I got all my friends together and we all camped out in
8:02 Speaker 00 line at the singular wireless store for 26 straight hours. And we were first in line at the store to get the original iPhone. And I remember telling Evan that story and he got really excited because he loves the iPhone. So we sort of high-fived across the table. In that moment, he was like, I have the perfect job for you. Later that day, I got a job offer in my email and it said, "Product Designer" as the job title. And I looked at this job offer, it said, "Product Designer." And I was like, what is a product designer? I literally had no idea what a product designer was. So I tried to Google it to understand, but I still didn't really grasp it. But I'm so appreciative to Evan for helping me to see myself as a product person.
8:45 Speaker 00 Because up until that point, I'd just seen myself as an engineer. But then he saw what I was doing, he saw what I was building, he saw the way that I thought, my passion for products like the iPhone. And he helped me sort of see myself in a new light.
8:57 Harry Stebbings? I told you this is like a chat, which is why the schedule can be a little bit misleading. But everyone always says Evan is this kind of product visionary. You've worked with him on product for many years. Yeah, he was like nine years in the end. Yeah, nine years and two months calling to LinkedIn. What makes him so good at product, Will?
9:13 Speaker 00 Evan has got an unbelievable product instinct, just so quick at understanding social interactions between humans, understanding what makes a beautiful design. He's got really strong values when it comes to product. I mean, he's instilled the way that he sees the world, the values that he has into the company. He's a really amazing storyteller. He's an amazing communicator. He's, I think, part of being good at product is communicating your ideas and your vision. And he is just a very inspiring product thinker. He's brilliant.
9:46 Harry Stebbings? You worked on and kind of were central to many different elements of Snap, which is so loved today. If we start on Discover, what are the biggest lessons you have from being so central to Discover?
9:57 Speaker 00 I think one of the biggest lessons from Discover was it's really important to understand the traffic patterns of how people are using your app. Because we had spent more than a year building Discover and launched it. And it was sort of hidden off in the corner of Snapchat. Like, the way that the app is laid out is like at the very right of Snapchat, essentially. And, and we found that ironically, it was actually pretty hard to discover, discover for our users, for our Snapchatters. And so it was actually, it was a pretty intense launch because, you know, we built up all this hype around it. And a lot of the media partners that we had were really excited. And then we launched it and people weren't discovering it. So then what we ended up doing was a very small design tweak.
10:39 Speaker 00 We moved Discover one screen to the left, essentially, to be on the same screen as where you see your friends' stories. And that completely changed the fate of Discover. It made it so easy to, again, discover, discover. And it really helped me understand the importance of thinking through the ways that people are using your app today and thinking through how to gracefully expand your product feature set. By wedging additional functionality into the right portions of your user interface, if that makes sense.
11:10 Harry Stebbings? Another element that you worked on, which is crucial as well, is the gaming platform, which I think a lot of people don't actually recognize. I heard about trips to Australia, we can get into that later. But what are the biggest lessons from working on Snap's gaming platform?
11:22 Speaker 00 Oh, Snap Games, what it was called, was one of the most valuable experiences I've ever had. I had a lot of lessons from it. I think some of the best product thinkers actually come from game design. I think for me, Snap Games, the biggest lesson was in sort of understanding and sort of building the confidence and the courage in myself to overcome challenges, as sort of corny as that sounds. I was in my twenties and I had never before managed a team. I'd never before acquired different companies in pursuit of a vision. And I remember actually the launch of Snap Games was quite chaotic and I think one of the most stressful periods of my life, where we tried, we ended up launching it with this
12:06 Speaker 00 sort of grand keynote on stage where I was, it was the first ever keynote for Snap and I was talking in front of thousands of really important people and public speaking really terrifies me. And I'd never actually before spoken to a reporter, a journalist. And then, so my first time ever speaking to a reporter was actually speaking to a whole room full of really prestigious reporters and they were all sort of like cross-examining me. And it was just, all of this was happening right at the same time while we were simultaneously trying to launch this crazy new product on this like unproven technology in partnership with game develop, five different game developers from different continents and time zones around the world. It was just, it gave me a lot of confidence actually, because at the end of the day, I persevered through it.
12:49 Speaker 00 After getting through that, I'm like, wow, I can actually, I can get through a lot more than I really thought. So I think it just gave me more courage to challenge myself and it made me sort of start to realize that imposter syndrome, which is always something that I've felt my entire life and I still feel to this day, is, it can be a good thing. It always used to terrify me, but now I'm almost, I intentionally put myself into these imposter syndrome like uncomfortable positions because it just means that I'm pushing myself to learn and to grow.
13:17 Harry Stebbings? My question to you is, you know, I think often people can feel imposter syndrome when they're thinking about art versus science and product in particular. They like to lean on data and science. Because of a fear of their own conviction or courage or lack of courage sometimes, as awful as that sounds. And I always think, is product art or science? How would you answer that question? If you were to put a number on it, where would you place them?
13:38 Speaker 00 Product is equal parts art and equal parts science. I I'm just sort of beginning to build a new team here at Match Group called ASL, ASL. It has two meanings, but one of the meanings is Art and Science Lab, which reflects my belief that the most innovative and the best products sort of happen at the intersection of artistic disciplines and and sort of scientific or technology disciplines. And it's sort of like a dance between the two. You need to bring folks from multiple different perspectives and backgrounds and trains of thoughts together to sort of swarm around solving problems for people in order to create really innovative products. So as a product leader, I think in addition to making sure that the team has art and science backgrounds,
14:23 Speaker 00 I also think you need to take a sometimes artistic sort of intuition and instinct driven approach and sometimes scientific data driven approach when you're actually developing a product and growing a product over time. So sometimes you have to lead with your instinct, you know, when you're taking a product from zero to one, you know, no amount of data or market research is going to tell you exactly whether it's going to work. You have to take a leap of faith. But then oftentimes, when you're iterating beyond that, you can use data to inform your instinct and to inform which direction you want to go.
14:52 Harry Stebbings? Speaking of that intersection and the subconscious that you mentioned there, you've spoken to me before about kind of the human centered design importance and focus. And I I didn't really have an idea what you meant, to be honest, Will. So before we dive in, what is human centered design?
15:09 Speaker 00 At its core, human centric design is just keeping your end users, humans, at the forefront of your mind through every single step of the product development journey, from the very early stages of ideation and need finding and building empathy for your your customer. All the way through development, prototyping, showing prototypes to users, getting their feedback, iterating, launching, et cetera. It's really just keeping the human at the forefront.
15:37 Harry Stebbings? Where does human-centered design most get lost, Will?
15:39 Speaker 00 I think it can get lost if you, again, sort of lean on data too much. Because oftentimes, you know, a data, a signal that you're seeing in the data might tell you to do one thing. But if you don't stop and sort of think about how whatever feature change that is might impact your end users, how they feel, or how it might impact the problems that you're solving for them, then you can lose sight of your customer at the end of the day and end up going down a path that might have long-term detrimental consequences.
16:08 Harry Stebbings? Are there products that you think of today that do this brilliantly and that do this badly to bring this to life for us?
16:14 Speaker 00 The Apple Watch is a fantastic example of a product that I assume was was made with human centered, with a human-centric design approach. Because if you think about it, I mean, I feel like human-centric design is all about identifying problems that humans are having, your users, your customers are having, and figuring out how to solve them through a blend of art and technology. The Apple Watch is an incredible product. I mean, look at how ubiquitous it's become over the last few years. And elderly people, for example, it's like a, it's a problem that in old age, if you have a nasty fall, it can have long-term detrimental health consequences. So it's incredible that the Apple Watch can use its accelerometers and motion sensors and all that kind of stuff to actually detect these falls and notify emergency services.
16:59 Speaker 00 I mean, even looking at the, I don't know if you saw the most recent announcement for the Apple Watch, I think it's called Double Tap. They saw that there's a problem with using the Apple Watch today. Every Apple Watch as we've known it up until this point, you can't actually tap on the screen to hit like a button on the watch if your hand, if you're holding a cup of coffee or if you're like walking the dog or something like that with a leash. So they invented this feature through a blend of intuition and instinct and art and science that lets you double tap your fingers on the same hand, you know, where you're wearing the watch, and it actually hits the primary action on the watch. It's another example of just how this human-centered design is looking at the problems that humans have, your users have, and figuring out how you can solve them.
17:42 Harry Stebbings? Okay, who does this shit?
17:44 Speaker 00 For me, as a user, Concur. Do you know Concur?
17:48 Harry Stebbings? Of course I know Concur. It's terrible.
17:50 Speaker 00 Okay, that's not just me. I mean, it's just, it's serving a different type of customer. So it's really good for an enterprise. I mean, it's like an enterprise SaaS product. They can have a really successful product because they're solving the right needs for an enterprise customer, another company that they're selling to. But I don't know if that product was designed from the ground up with the end user in mind.
18:10 Harry Stebbings? No, it's like bill.com. I always think with these companies, like, do they have anyone in product?
18:15 Speaker 00 I think it's just a different, it's a, it's a good different product mindset and philosophy. It's like enterprise product is very different from consumer product, which is, you know, where I normally focus my energy, where, you know, I think the human-centric design approach really matters.
18:28 Harry Stebbings? When we actually say that about the human-centric design approach, when you break it down for me today, if I were to say, I am a founder listening to you and I want to do it, what is your approach and how can I do it, Will?
18:40 Speaker 00 I mean, it's essentially identifying your target user, the people that you want the most to use your product, building empathy for them through whatever means necessary, really. I mean, you can get really scrappy. If you're an early founder entrepreneur, you can go talk to people on the street.
18:57 Harry Stebbings? What questions do you ask to uncover user needs? Because it's hard.
19:01 Speaker 00 For me, the first thing that comes to mind is, you know, I'm at Match Group thinking about how to continue to spark online connection around the world. And I would ask, what's your approach to dating? Have you tried online dating before? If you were to try online dating for the first time, which apps would you consider? If you've gone through online dating already, like, what are some of the struggles that you have? What are some of the challenges? Tell me your problems. You basically just want to hear about what problems they have so that you can, you know, so someone that might say that, oh, getting started with online dating is actually really challenging. There's tons of different apps out there that you can choose from. How do you know how to make a dating profile? It's just incredibly challenging. It's like a little awkward to figure out how to represent yourself with photos
19:44 Speaker 00 and some texts online in front of, you know, potentially millions of strangers in a romantic setting. So just thinking. Hearing, listening to their problems, formalizing those problems, writing them down, and then bringing together really smart, creative people from different backgrounds, that art and science background, to really think about how to solve those problems.
20:05 Harry Stebbings? You said about the kind of creation of profiles. Is simple always better when it comes to product design?
20:11 Speaker 00 It's not always better in my experience, but I do think that when you are creating a novel product that people don't yet understand, something that's truly innovative and new, I do think that simplicity is paramount towards making it easy to use. And I think about the original iPhone, for example. It was very simple. Actually, they use user interface design patterns like skew-morphic iconography to help ground people's understanding in real, physical analogies. And then over time, iPhones have gotten much more sophisticated. They've added in feature after feature and after feature. The reason that that can work is because if you start simple, then you have a core product.
20:55 Speaker 00 If you're lucky enough to find product market fit, then you've got a simple core product that people can easily pick up and understand. And then, once you've sort of captured their attention, once you've found that product market fit, then you can take them on this journey over time where you layer in complexity. You can really push the boundaries of what the design language can do in order to introduce new features and new complexity that solves the user's problems in totally new ways.
21:20 Harry Stebbings? Can I ask, how do you prevent feature creep? It's so easy over time just to add more, add more, add more. And then you look at the product and it's like, oh, that is cumbersome. How do you retain simplicity with time?
21:32 Speaker 00 I mean, this is really where I think there's a lot of art involved. You have to think through the right level of abstraction with features. You don't want to open up an app and see hundreds of toggles and different settings and different switches. It's just overwhelming and confusing and hard to understand. But you do want to make some of those settings and toggles available for a power user, someone who really wants to push your product to its limit. Figuring out from a design perspective, how, like what the information architecture should look like, how to tweak the interface to be approachable for a layperson, but to have depth for a more power user, if that makes sense.
22:16 Harry Stebbings? How do you strike that balance, though?
22:17 Speaker 00 Through a lot of iteration, experimentation, coming up with literally hundreds or thousands of different mockups and designs through, I'm a huge fan of rapid prototyping, like not just creating interactive Figma mockups that you can click on, but literal prototyping with real software code, so that you can just rapidly experiment and feel out using your intuition and your instinct and do user studies and all that kind of stuff to figure out if it's approachable for a layperson.
22:48 Harry Stebbings? I was speaking to, I don't know if I'm saying this right, but Pani before the show.
22:53 Speaker 00 Pani, yes.
22:53 Harry Stebbings? Pani, yeah, so I was talking to him before and he said to me about a time when the team wanted to ship a product, when it was like, it was a little bit, you know, a little bit creaky. And you were like, no, just no, guys, not gonna happen. How do you think about like, speed of execution and is good today better than perfect tomorrow?
23:12 Speaker 00 I am, I can be sometimes known to be a stickler for design details and I guess where that comes from is when you're working with a product team in pursuit of a vision, you want to put a product out there that, or at least in my experience, you want to put a product out there that you can be really proud of. And I think first impressions really matter, whether it's the first impression for your target customer or for reporters out there, whoever it is. I've always felt that when you're launching something brand new, it can't be perfect. Perfection is, it just takes forever and you know, you might not actually, if you try to build perfection, you launch it after taking years, then you might find out that it actually isn't solving a real user need and then you might have
23:56 Speaker 00 to start all over. But you at least should launch something that you're really proud of, that reflects, it's emblematic of the vision that you're trying to achieve.
24:03 Harry Stebbings? Does that go against rapid prototyping? If you think about something you're really proud of, rapid prototyping, like, hey, quick and dirty, does this work? Does this work? Do you like it here? Do you like it here? Do they not go against each other?
24:13 Speaker 00 I actually think that rapid prototyping is a critical tool for any product person to accelerate the path towards putting something out onto the market that they're proud of. Because it basically allows really rapid iteration and guidance by your intuition and instinct. Within your own internal team, within the people who all share a vision of what you're trying to achieve, and it also allows you to do sort of informal user testing. You just hand your rapid prototype, you hand your phone to a friend or a target customer and see what they think. So I think it's it's actually quite complimentary to the idea of of getting a product that you're proud of out there.
24:51 Harry Stebbings? Okay, so we see what they think, and then we have a product review. And again, I'm not in the product world, and I want, and a lot of CEOs aren't. And so I want this to be like for lessons for them. When we think about product reviews, how do you do them? What makes a good versus a great one?
25:08 Speaker 00 I have a few different types of reviews. I don't know if you sort of bucket this under a product review, but I think the environment for a brainstorm is also extremely important.
25:19 Harry Stebbings? Let's start then. Brainstorm, are we in person or remote? Do we have a whiteboard? Do we have a mirrorboard?
25:25 Speaker 00 I guess I'm old fashioned. I like a whiteboard. I I think that when it comes to creative brainstorming and design brainstorming, being in person is just of paramount importance. I think your physical setup actually is extremely important. I like to try to create a relaxed atmosphere where you're sort of on a couch, casual and conversational. And I like to create a safe space where you sort of have psychological safety to throw out some crazy ideas. Because I've often found that wacky ideas that are sort of almost like half jokes can actually have a really important edge to them that can, at the end of the day, turn into a really amazing idea, product feature.
26:04 Harry Stebbings? Do you cap it at a certain number of people? How do you determine who to invite? I'm just intrigued to really get to grips with kind of the bare bones.
26:12 Speaker 00 It's actually really important to have a small group of people, because otherwise you just get into these situations where there's too many cooks in a kitchen and there's too many people that can sort of shoot down ideas, which I think is the worst thing when it comes to creativity. I mean, it could just, shooting down ideas is something that I just. Really try to avoid in the sort of like product culture that I create because any idea can have merit if you look at it under a certain lens. But yeah, I try to cap it to maybe like five people max. I mean, there's like a rough rule of thumb, but I think it's really important. It's like people that you trust. You know, the way their minds work, you're all coming at a problem from a different perspective. Maybe someone has, maybe someone's formally trained in product design, or maybe someone is an engineer. And you can think about it from those different lenses.
26:55 Harry Stebbings? Do you set an agenda beforehand?
26:57 Speaker 00 I have in the past. I think setting an agenda can be important, but sometimes if you add too much structure, it can stifle creativity. It's like this constant tension or this like struggle that I face internally where I think some of the most creative ideas can arise from chaotic environments. But you also have to like have some level of structure to sort of keep people on task, if that makes sense.
27:18 Harry Stebbings? How do you bring chaos to environments? I'm a rebel rule breaker. It's why, again, never went to college and mother still thinks I'm dealing something on the internet. I want to rock up with Chanel and she still doesn't know what I do. The fund helps, I have to admit now.
27:33 Speaker 00 I'm sure.
27:34 Harry Stebbings? She says to everyone that I'm a hedge fund manager. So, you know, quite mum, but you know, we're there. Yeah. But like, how do you bring chaos? How do you inspire creativity? How are you like, let's actually fucking think outside the box here.
27:46 Speaker 00 Two things come to mind for me. I think one, just bringing together people from diverse backgrounds and perspectives. I just can't underscore enough how important that is so that you have people thinking about the same problem, that same human need that you're trying to solve from a totally different perspective. Bringing these different perspectives together can help you analyze a problem in a different way. The other thing that I think is really important is inspiration. Traveling around the world and seeing your target customer, for example, in the flesh. Observing the way that they're interacting with the world and understanding their environments in a really nuanced way. I think getting the right sort of creative inspiration is paramount towards coming up, towards generating that chaos and coming up with the right ideas.
28:32 Harry Stebbings? It's really hard when you're the product leader and you've got revenue generation today and innovation for tomorrow. How do you think about balancing investing in what makes money today and making sure that machine hums? But also being sure that you have an eye on generative AI and new ways of creating profiles that's seamless and easy. And you don't need to do anything or whatever that may be. How do you balance the two revenue generation and an eye to the future?
28:57 Speaker 00 I mean, you need both. I have found that the best approach is having two separate teams that are dedicated towards each of those two independent goals. So one team dedicated towards revenue generation, another team generated towards innovation. Because oftentimes there's a really strong tension between those two. When you're building a product, you might have to deteriorate your revenues with a new feature in order to experiment with some really innovative new idea. And if it's the same team making those decisions, that conflict of incentives can be paralyzing for development.
29:34 Harry Stebbings? Do they need to work together, those separate teams? Or are they quite clearly distinct and different?
29:38 Speaker 00 They definitely have to work together. So I think that, I mean, that's sort of like part of the role of a product leader is to be able to properly balance between the needs of those two teams. It's creating the right communication pathways, the right processes for those teams to collaborate with each other and share notes and ideas. I think you need to think about how to build a culture of information sharing and one where people from those two different teams can actually get to know each other personally. So they can build trust with each other as humans.
30:10 Harry Stebbings? What are the mistakes that product teams get when it comes to culture? How does product culture go bad?
30:16 Speaker 00 For me, I like to create a culture where everyone is growth minded, where everyone practices humility, empathy and listening to one another. What I don't like is when you've got folks that are very egocentric, really ego driven, people who think that they know everything because that can be poisonous to your team culture. It can stifle the voices of other people in the room. And it can plant these seeds in the team that over time can tarnish the rest of what you're doing. I think a lot about team culture and how every single person is like a seed in your team. And those seeds over time blossom into trees. And I guess your team is like a field of trees. But if you've got the wrong people.
31:01 Speaker 00 It can be like a, I don't know what the right analogy is here. It can be like a, like a parasite that can grow over time. So you have to get rid of it really quickly.
31:08 Harry Stebbings? What a wonderful floral analogy and I'm glad you're, you're, you're taking on Attenborough for the analogy.
31:15 Speaker 00 If that doesn't work out, then who knows?
31:17 Harry Stebbings? You know what? You do, you need to change the voice a little bit. He's got the
31:21 Harry Stebbings? I, I totally agree with you on the importance of that culture, but that comes down to you and you're hiring actually and getting the right people on board. You've done it at Snap very well. You're doing it again at Match now very well. My question to you is, first off, before we talk about the people, how do you structure hiring for product? What does that process look like? Again, I'm an angel investment of yours. I've never done it before. How do I hire product people?
31:45 Speaker 00 What I've found, I specifically look at products that people have designed or built in the past. Someone's actual work speaks volumes, more than you can possibly extract out of like a, a few interviews. I think it speaks volumes to the way that they think, the way that they communicate their ideas.
32:04 Harry Stebbings? What do you want to see in the products that they've built?
32:06 Speaker 00 Okay. So when I was first building Snap Games, actually this goes back to the Australia comment that, um, that you made earlier. I had this kind of crazy vision, vision of, uh, creating these multiplayer games in Snapchat that were fun and vibrant and colorful and featured your, your bit mojis. You could play as your bit moji in Snapchat with your friends. And Snap didn't have game development expertise already within the company. So I started looking for game studios out there in the world that we could potentially acquire through M and A to sort of bring that expertise into the company. And I found a game that just really spoke to me. It was multiplayer,
32:48 Speaker 00 real time multiplayer. It was super fun and colorful. I remember that the music had the right energy that I was looking for and then everything just.
32:54 Harry Stebbings? Was this Fruit Ninja?
32:56 Speaker 00 It was the same creators, actually. The, the, the game was actually called Crash Club. I don't think it's actually on the App Store anymore, but the user interface of the game menus was like this 3D box that you would like swipe and tap on and like the box would spin around in 3D. It was a very sort of a novel approach of thinking about. UI interaction design before I had even met the developers behind the game. I was like, this is the game studio that we need to acquire. So then actually, I, you know, I found a way to get connected to them. We had an intro call in that intro call. All I was looking for, like I, I was, I was already sold on their product abilities, on their game creating abilities. But all I was really looking for was whether it was a good culture fit, whether we got along, whether they had a,
33:40 Speaker 00 you know, personalities that I thought that I would like to work with over time. And literally like, we had one call, they were in Australia, I was in LA. I confirmed my suspicion and I immediately flew over to them like the next day to Brisbane, Australia, to pitch them on essentially Snap buying their game studio. And we had, we made it happen incredibly quickly. So getting back to your question, it depends what product you're trying to build. But I think if you have a certain vision in mind for the kind of product that you want to create, you'll know it when you see it, when you see what they've done in the past.
34:12 Harry Stebbings? Can I ask, what are the single best qualities you look for in a product designer? You mentioned there the design of, you know, the 3D shapes and spinning. What are the best qualities of those product designers?
34:22 Speaker 00 For me, I like to find, whether it's a designer or an engineer or a product manager, I'm looking for people who are very growth minded. I mean, I'm, you know, I, I think just inherently when you're trying to push the envelope with product innovation.
34:38 Harry Stebbings? What does that mean? Like they're very growth minded. Sorry, I'm pushing you on that.
34:41 Speaker 00 Like someone who is open to change and adaptation and learning. Someone who has the innate intellectual curiosity to understand the way the world works or to improve their abilities.
34:55 Harry Stebbings? How do you test that in an interview?
34:57 Speaker 00 Observing the types of questions that they ask you. Actually, when I hire anyone, I'm always asking what their long-term career ambitions are. So I can understand how much thought they've put into what their end state, what their end game really looks like. And I want to make sure that that end game is at least something that I can support.
35:18 Harry Stebbings? What would turn you off in that 10 year? So I asked someone this the other day and they said, I want to be working nine to five. I work to live. What do you not want to hear in that 10 year plan? What would be like, oh, I don't want that.
35:29 Speaker 00 I mean, I actually, I believe in striking work life balance. I think that like the nine to five comment would also concern me, but it's not the end of the world. But I think at the end of the day, I'm looking for someone who's just really passionate about their craft and whatever it is that they're doing. Cause I think that passion is what drives people to work beyond nine to five. It's like, you have to understand people's motivation. It's like, why are they interviewing with you? What are, what are their career ambitions? What are they looking for? And if someone is looking for a nine to five.
35:58 Harry Stebbings? What do you think product people care about today? I think people's shift has been very real. People care less about money than ever before. Mission, nah. They say they do more because they think it's more moral, but they actually do care about the work life balance. I find much more than anything.
36:13 Speaker 00 I mean, I do think that the pandemic really helped people to realize that maybe you don't need to be in the office five days a week. Having some level of flexibility is conducive of having a little bit better work life balance. And maybe even being better, being a better teammate, being a better 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. I mean, this is one of the things that concerns me actually about product management as a discipline today. I feel like it's this sexy trendy job in tech that has an allure because it's known to be high paying.
36:55 Speaker 00 And I guess it's like, I, I try to weed out people who might only be interested in product management because of reasons like that.
37:02 Harry Stebbings? Like cash, PMs get paid pretty well, I think, right?
37:05 Speaker 00 They do, at least, you know, in certain companies where it's a highly valued function.
37:11 Harry Stebbings? Can I ask, on, on like case studies in the interview process, do you do case studies? If so, how do you think about doing them?
37:17 Speaker 00 I don't. I mean, I've always just felt that it's a little bit too artificial and forced. And it's like, kind of like, I mean, I was never, I think of a case study almost like a standardized test. You know, the classic brain teasers that some of these big tech companies, I don't know if they still do it, but at least, you know, when I was going through. College and sort of studying for my internship interviews and all that kind of stuff is all about these brain teasers. I don't know, it's like a certain type of test of someone's thinking. But if they're not good at brain teasers, they can still be good at a lot of other things. So I don't really take a very structured approach when it comes to my interviews with case studies or brain teasers or anything like that. Do you know pretty quickly when someone's good, do you think? I do, I think I do. I mean, honestly, I look at what they've done.
38:01 Speaker 00 I look at what they've built, even if they're really early in their career, looking at concepts that they've created and asking them about those concepts, asking them, oh, why did you put this button here? Or why did you use this specific copy, this specific string of text in the user interface here to get an understanding of how they think, to get an understanding of how passionate they are about product? What've been your biggest hiring mistakes? For me personally, I mean, I, I think that 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 guess. I'm like a glass half full kind of guy. And my friends always actually give me a hard time about this because I tend to like
38:46 Speaker 00 everyone, even people who are, who most people severely dislike. I, I, I love them because I just like see them for who they are and I think they bring something special to the world. But I think that does make it so that sometimes I give people a long leash and, you know, I may need to sort of like read the signs from the team earlier to figure out that maybe they aren't a great culture fit, or maybe they're just in this for the money and not that passionate about our mission. Is it wrong to be just in it for the money? I do not like the idea of like a paid mercenary. I think that the most profound and innovative products come from a deep passion for creating something that can have an impact. Do you like people who've had experience in that space before? Not necessarily.
39:31 Speaker 00 No, I think it's really oftentimes valuable to bring in folks from a different perspective, to think through from a first principles point of view, or, you know, by leaning on the expertise, that unique perspective that they have, how to create a certain type of product or feature.
39:47 Harry Stebbings? I totally agree. I think actually that it's very beneficial, especially like gaming in particular. I love hiring people from gaming to non-gaming products.
39:53 Speaker 00 Totally. This is what I'm saying. It's like when I got to know the game development community, I mean, I encountered some of the most brilliant product thinkers in the world and I just had no idea.
40:02 Harry Stebbings? Listen, I want to talk about the future and then we're going to do a quick fire.
40:04 Speaker 00 Okay.
40:04 Harry Stebbings? As I've roamed around here, we have to talk about kind of the impact of AI. First impact of AI on product design. How does AI change the actual process of product creation and design, do you think?
40:14 Speaker 00 I think in a few different ways. First of all, as a product designer or a product manager, I think AI has already created a bunch of tools that we can use to be super product designers or product managers. I mean, thinking through like, you know, I have already some product designers on my team who are using tools like Mid Journey or Dolly to come up with different UI concepts or visual concepts. I actually think I was experimenting with, I guess they're called LMMs, these large multimodal models that are both like they can talk with like language, like a chat GPT, but they can also see. They can see imagery and photos and analyze and understand them.
40:55 Speaker 00 And I think there's probably going to be an AI tool in the near future that gives you instantaneous user feedback and testing. Like you create a mock-up or a prototype and you hand it to the AI and you say, hey, AI, give me feedback on this new experience as if you were a 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 actually started like playing with some of these LMMs in this way and I think it's definitely just right around the corner. So I think like making sure that you understand how to utilize these latest AI tools is probably really important towards making sure you've got the right tools at your disposal to do a good job.
41:35 Speaker 00 And then obviously, when it comes to product design, I think understanding the capabilities of AI. I mean, I think AI is going to completely change every facet of life as we know it, essentially, over the next few years. And therefore, I think it's really important to understand the capabilities and limitations of the technology and figure out how to gracefully weave that into your product design so that you can stay relevant.
41:57 Harry Stebbings? I've had many people on the show say that in the world of AI being kind of center stage and the impact it has on product. UI will really be completely irrelevant and it'll be BS. Do you agree with that statement or do you think that's overly simplistic?
42:11 Speaker 00 I do not agree with that at all. I mean, AI is an overloaded term. I think these days, you know, right now in this moment, when we think of AI, a lot of people are talking about large language models like ChatGPT. What I think is so amazing about ChatGPT is that it opens up an entirely new paradigm of human computer interaction. We theoretically no longer have to interact with computers through user interfaces and buttons, but we can just talk to computers. It's actually really powerful because I think about my mom, for example, she's in her mid seventies. Because she didn't grow up with mobile phones, understanding how to use and navigate mobile interaction and user interface paradigms, she's not that good at using apps on her iPhone, but she's really good at talking.
42:55 Speaker 00 So it's incredible to me how something like ChatGPT can enable an entirely new mode of interaction with computers. But I don't think that the previous human computer interaction paradigms are going away. The command line interface, that was one of the original ways to interact with computers. Like people are still using command line interfaces today. Similar vein, I think people will continue to use user interfaces on a screen, on a laptop or on a phone, even in a world where talking to a computer through a large language model is pervasive.
43:25 Harry Stebbings? I, listen, I totally agree with you. I can't wait for my mother to actually be able to use a piece of technology at all. She still calls it Goggle. And so, you know, it'll be a relief if she can talk to her phone and give me a break. Trust me, Will, I am all for it.
43:39 Speaker 00 It's gonna be incredible.
43:39 Harry Stebbings? It's gonna be great, it's gonna be great. Her husband's gonna love it even more. My question to you, generative AI, I'm a venture investor. Is it worth the hype?
43:47 Speaker 00 I do think the hype is warranted, but I'll caveat by saying I wouldn't just invest in every single generative AI based company that comes across my radar. I think there's a lot of entrepreneurs right now who have a great idea maybe for how to apply something like ChatGPT to a new application. But if they're essentially just prompt engineering on top of the same large language model that everyone else has access to, then I worry about their long term defensibility. But fundamentally, I do think that the hype around generative AI is warranted. I think, you know, going back to that shift in human computer interaction paradigms, it just allows us to interact with computers in an entirely new way. And on top of that, the fact that these large language models are trained on
44:32 Speaker 00 All of the world's information and data is just incredible. It's like it's true intelligence. It's democratizing access to intelligence over time, especially as the cost of accessing the inference gets cheaper because these AIs can actually reason across multiple domains, whether it's human history or science or medicine. It's just incredible to be able to have this intelligent system at your fingertips that can access like all of humanity's knowledge. It's incredible.
44:59 Harry Stebbings? Can I ask you a weird one from a product perspective? Is it really hard by your most successful users never use you again?
45:05 Speaker 00 Sorry, say that one more time.
45:06 Harry Stebbings? Well, if you think about Match, unlike Snap where like great champion users use Snap more, if you have a really successful Match user, they're like, thank you for finding me the love of my life. I'm off now.
45:18 Speaker 00 No, I think it's beautiful. This is what wakes me up every day, to be honest. It's just thinking about the impact that we can have at a global scale on real people around the world. I mean, it is a major success for us if we never see someone again because they found a relationship that they're happy with for the rest of their lives. I think it's amazing. It's a little like, it's a little strange, but it's something that I'm still getting used to because if we're successful, then we lose users. But then I think a lot of our job comes down to making sure that we can always capture the next generation of users, you know, those people who are just coming of age to think about dating and sparking romantic connection.
45:53 Harry Stebbings? Do you think dating apps are even competitive? People have four. Back when I had dating apps when I was single, Will.
45:59 Speaker 00 Okay.
46:00 Harry Stebbings? Important to say I don't have any more, but you would have five. You would just do it to be as successful as possible. Are you actually competing?
46:07 Speaker 00 I actually think about it more as collaborating, frankly, to like, it's like partnering up with other apps and other brands, you know, many of which are actually within the Match Group portfolio.
46:16 Harry Stebbings? But I'd say your competition are games. Sorry, this sounds awful. Where do you go on dating apps mostly? Mostly when you're on the loo, when you're, sorry, when you're on public transport in the UK, like we have trains, buses or in Ubers. I would say it's not like dating apps, you're competing against other casual games.
46:34 Speaker 00 I mean, there's only 24 hours in a day. And you know, there's only X amount of those hours that you're going to be glued to your mobile phone. So yeah, I mean, I think you're competing for time, your sort of share of mind, whether it's gaming or TikTok or whatever it is. I mean, at the end of the day, there's just a finite, finite amount of time in the day. And I think, you know, at some level, every single mobile app has this issue.
46:55 Harry Stebbings? No, I totally agree. I always say we're competing against Taylor Swift, which makes me terrified, terrified. You would choose Taylor every day over me.
47:02 Speaker 00 Formidable competitor.
47:03 Harry Stebbings? Formidable. What the? Uh, listen, I want to move into a quick fire, Al, Will.
47:07 Speaker 00 Okay, let's do it.
47:07 Harry Stebbings? Short statement. So tell me, when do you listen to users and when do you ignore them and go, you know what? Product roadmap. We're going to stick to what we know.
47:14 Speaker 00 I think listening to users is normally extremely important, though I think the one exception might be when something that users are asking for conflicts with one of your core product values. But then I still think you don't, you don't like ignore them. But I think it's just about like listening and understanding what they want, figuring out how to maybe solve that problem that they're having in a way that's adherent to your values.
47:37 Harry Stebbings? What's your work from home setup? I was told that you have some special work from home setup.
47:41 Speaker 00 I did go a little crazy about this over the pandemic. Um, I've got an Apple Pro Display XDR. I mean, I've iterated on a few cameras, but at this point I've got something called an Insta 360 Link, which is just an incredible webcam on a gimbal. It's, it's amazing. I've got a custom keyboard. I'm a huge nerd. I mean, you know, think about me growing up on IRC. I've got a, what's called a Leopold FC 660C keyboard with Japanese topre switches in a custom housing made by someone named Ryan Norbauer, who's like an artisan keyboard case maker in Los Angeles. What else? Oh, I've got a Logitech MX Master 3 mouse. I swear by that mouse. I don't know, I could go, I could, I could do like an entire podcast on my work from home setup.
48:27 Harry Stebbings? No, you're a totally normal guy. Don't worry, Will.
48:28 Speaker 00 Totally normal.
48:29 Harry Stebbings? You've just, you know, yeah, destroyed all street cred. Can I ask, what would you say is the biggest mistake founders make when hiring product teams?
48:37 Speaker 00 Not getting rid of or culture fits fast enough.
48:41 Harry Stebbings? What's the first sign?
48:43 Speaker 00 You see the way that they're treating another coworker. If they're not kind, if they've got an ego and they think that they know it all. I think these are the things that can be deteriorating to your culture that you're trying to build over time.
48:56 Harry Stebbings? What one piece of advice would you give to a product leader starting a new role first thing tomorrow?
49:01 Speaker 00 Just get. Reps in building products, no matter what it is, just build anything, even if it's a personal project on the side, because I think getting those reps in is really important. And embrace imposter syndrome. Imposter syndrome is a good thing because it means you're growing.
49:16 Harry Stebbings? What's the watch collection?
49:17 Speaker 00 I have been obsessed with watches since I was like a little kid, literally. I mean, I've got like a drawer full of all the watches I've ever owned in my life. My old G-Shock, my Nike watch, Swatches growing up. More recently, I've been exploring all different types of brands and I just love watches. It's like this amazing blend of art and science and technology. I love how it's like a form of self-expression. I love how they're sort of anachronistic nowadays, you know, at a time where we're just surrounded by digital computers, having a mechanical watch that's got this heartbeat of its own. That's sort of like, as long as like you're wearing it, its heartbeat is like in unison beating with your heartbeat. I just think it's incredible.
50:00 Harry Stebbings? I was thinking in terms of marketing, like, you know, the Patek marketing of, you know, being for generations.
50:06 Speaker 00 Absolutely.
50:07 Harry Stebbings? Is fascinating. And actually, how different, how different social capital accrues to the different styles. And like what you wear is who you are in some respects. Do you know what I mean?
50:17 Speaker 00 I a hundred percent know what you mean. Every single day I look at my watches and I'm like, who do I want to be today? It's an incredible form of self-expression. And I also like, to your point, I guess I'm a sentimental guy, but I love how you can get a watch to celebrate or commemorate a certain milestone for the rest of your life. Whenever you wear that watch, you think about, you get nostalgic about that milestone. I just think it's really important what watches can symbolize.
50:42 Harry Stebbings? I mean, we could change it to a Patek, it's not for life, it's for your birthday. Sadly, no mother or girlfriend has ever done that for me. But listen, final one, what recent company product strategy have you been most impressed by? What have you seen another company do and you're like, smart?
50:56 Speaker 00 Okay, I have to give a shameless plug for one of our own companies, Tinder. They have been working on this new AI feature that allows users to very quickly surface the best photos from their camera roll, all using AI in a privacy safe way. When I first signed up for Tinder.
51:14 Harry Stebbings? How do you do that? Surely that's subjective.
51:16 Speaker 00 It's possible to create a model, an AI model, that can predict which photos that already exist on your phone will best perform on Tinder because you've trained that model on highly performing photos on Tinder. I'm optimistic it can really solve a huge user problem that I felt when I first signed up for Tinder years ago. It's like, I don't know how to choose the best photos of myself. I hate photos of myself. It took me weeks to figure out the right photos to put on my profile. But being able to do that almost instantaneously, I think, can be a friction remover.
51:50 Harry Stebbings? I love this. As I said, I heard so many great things from Jack. I've wanted to do it for a long time. Thank you so much for putting up with my wayward questions.
51:57 Speaker 00 Thanks so much, Harry. It's been a pleasure.
52:00 Harry Stebbings? Now, if you want to see the full video, you can check it out by searching for 20VC on YouTube. That's two zero VC. It was such a great show with Will. But before we leave you today, imagine shipping new webpages in weeks instead of months, saving millions in development costs while teammates across multiple departments and time zones seamlessly collaborate on your site at the same time. Webflow's visual-first platform means design and content changes aren't dependent on engineering. So your marketers and designers are free to take back control with tools that support your growth. Need a CMS that can handle 40,000 pages? A native localization tool that can fully tailor your site to 22 different locales?
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Previous 20VC: The Metrics That Matter in SaaS Today; Why CaC Payback is Flawed & CAC Ratio is Better, Why You Need to Hire Three Sales Reps at a Time, How to Forecast in 2024 & Biggest Mistakes Made Forecasting & How to Make Customer Success Sell More with Dave K Next 20VC: The Biggest Misconceptions & Hardest Truths About Seed Investing Today; Why The Best Founders Don't Need You, Why Uncapped SAFEs Are Good, Why Reserves Are Bad, Why Signalling is BS, Why Price Doesn't Matter with David Tisch & Terrence Rohan Page updated September 29, 2026 · transcript and summary are machine-generated
