Very Fine Day #27: Hunter Walk

Brad Esposito

HUNTER WALK is a partner at seed-stage venture fund Homebrew and former Google and YouTube weapon. While he’s now 12 years into his VC lifestyle, Hunter worked early on in the workshops of Linden Lab (SECOND LIFE) before tackling YouTube consumer products, making YouTube the first non-Apple app to land on the iPhone. At Google, Hunter arrived at 1000 and left at 12000, watching an entire digital ecosystem grow around him. He has worked for “Late Night with Conan O’Brien” and grinded a BA in History at Vassar. Early in into the social internet, Hunter offers a fascinating insight into the early years (AND CREATION OF) the creator economy.

VFD: What have you been up to today? What's a day in the life for you at the moment?

Hunter Walk: I was on the East Coast last week, and now I'm back in San Francisco, which means a day in the life is 30 degrees cooler than it was in New York. But it's just me and my dog at the moment – my wife and kid are are out of town. I'm gonna join them later this week. So that means I'm the proverbial old man on the computer all day, zooming with founders and other investors, taking a walk here and there, and then letting the dog sleep in our bed, which my wife hates. But I think it’s like: if you can bring that much pleasure to someone or something by just allowing it to sleep next to you, who are we to deny someone else that pleasure? It makes the dog so happy and it makes me happy. So I just change the sheets before my wife gets back.

VFD: What kind of dog?

Hunter Walk: She's a Swiss mountain dog. Like a short hair bernese, about 90 pounds. She was unintentionally a COVID puppy: we got her in October of 2019 when she was about eight weeks old. Of course, a few months later we started to go into lockdowns and social distancing. I feel like we got some good reps in with her seeing the world, but she's still a little bit territorial. I don't think she’s used to strangers coming into the house with great frequency.

VFD: Yeah.

Hunter Walk: And so the first time she sees somebody she gets a little bit of stranger danger. Once she smells them and once she sees that they're a friend of ours she calms down. But I don't know, maybe it's the puppy thing. I'm just going to ascribe it to the COVID virus. She's a sweet dog.

We had a Rottweiler. This was 12 years ago – my wife got a Rottweiler when she was in college – and when I met her out here I was around for the second half of the dog's life. That was also a very, very sweet, 105 pound runt of the litter. But people would cross the street to avoid her because Rottweilers just have that reputation. And while this dog is still considerably large it's nice that she doesn't instil fear in people.

VFD: Yeah, we did a similar thing – in terms of getting a dog in the middle of COVID. Over here we got greyhound. We'll take her for a walk and she's afraid of everything. But people don't know that. And anyone with a dog smaller than her is pulling their dog close to them.

When you said before you were in zoom calls a lot, is that in your role as an investor at the moment? Is that what a lot of your job is at the moment: postponed zooms?

Hunter Walk: Well, I describe Homebrew as a concentrated, early-stage fund. So we try to make a handful of investments each year in companies that are just getting started and then spend meaningful time with them, especially the first three to five years. Part of the joy of that is really getting to know the founders and their teams to support them, but getting to know them as people as well. I think there's a lot of things in this job that are best done not over Zoom, but over whiteboards and meals and walks. Since things sort of opened up a little bit more I've gotten down to LA for a few days and I just got back from New York. I've been trying, certainly around here in the Bay Area, to flip back to the things that would be meaningfully better in person and taking the logistical burden off myself

VFD: Right,

Hunter Walk: So it’s not like: hey, founders, come to my office! Instead it’s going to see people. A handful of folks I've never met in person and we invested in them during the periods of separation. And then everyone else I hadn't seen in quite a while. I think that human touch can't be lost.

But yes, outside of that, a lot of things have flipped to virtual and I don't think all of them are going to flip back right away. Safety aside, I think there's just an efficiency that some people had to be convinced of and this convinced them of it. I also think that there were certain things where asking to do a call, or a video, had some sort of social stigma to it. Like a signalling of: you're not important enough to come to my office. I hope that remains a little bit flatter. Can we just focus on what's the right communication style for what we’re trying to accomplish? Which sometimes may very well be: no, we have to see each other in person or: this needs to be synchronous. Let me give you a call.

So yeah, that's how I'm approaching the reemergence into a world where maybe it’s OK to see people again.

VFD: Fingers crossed. How did you get into that? How did you make the decision on investing being something you wanted to do?

Hunter Walk: Y’know, I guess there was a single player decision and then a multiplayer decision. The single player decision – what I was deciding for myself – was when I was still working at Google and at YouTube. It sort of felt like my tenure at YouTube was wrapping up and I had this question about: do I stay at Google and just move on to a different product area? Or do I go somewhere else and start something on my own?

But I had found that I had gotten promoted to my level of unhappiness. Like, my job – which had been on the product management side – got to a point where I was managing teams and working through resource allocation, and less actually working on product features. It was more enabling my team to build what they thought should be built. I sort of burned out on that a little bit.

So I was thinking about: well, maybe it's time for me – after 12 years or so between Google and a startup I was at prior – to go from the “doing” side to the “helping” side for a while. Be outside of the team and just help the team build the best version of what they're going to build, whatever that means. Whether it's consulting, advising, filling a role in a temporary way.

So I wasn't thinking: Oh, I'm going to become a full-time professional investor. I'd been doing some angel investing but it was sort of like Kickstarter just at higher donor levels. I was investing in people and projects that I thought were interesting. Sometimes they had a financial return as a backup reward. Sometimes the project never shipped.

VFD: You ever have a moment where you were like: I should stop putting money into places where I'm not getting any back?

Hunter Walk: Yeah, I was coming at it from a place of extreme privilege. I was married without a kid and I had a little bit of disposable income from Google doing well, and I really wanted to accomplish two things.

I was a liberal arts undergrad and I really believe in adjacencies and learning about what's happening in other areas. And YouTube was, by its nature, forcing me to go deep and narrow on things like video, social, and community. This was in 2008, 2009, 2010: there was a lot of other stuff going on at the time, too. Mobile commerce was starting to find its its legs, you had businesses and industries starting to get the benefit of collaborative online tools. There was the beginning of the Cloud. All those types of things that I thought were fundamentally interesting, but I knew that in the near term my day job wasn't going to allow me to learn about those companies or learn about those technologies in a meaningful way.

One way of doing it was by riding shotgun on people who were building things in those spaces. When they happened to be friends of mine, even better, because then I felt good about that support. It was kind of de-risking the human part of it.

And you sort of asked: did I have a financial motivation? And if I wasn't meeting that mode, if I wasn't meeting that goal, would I have stopped? The way that I sort of thought about it was that I gave myself a budget each year to make a handful of angel investments. I said: Hey, look, once I commit this money I'm not gonna track it anywhere. I’m not trying to save up to buy a house one day. It was more: Let's assume it's gone. And after two years or so, if it turns out that I'm really bad at this, I should probably write it off.

But, if it turns out that I'm OK at it and at it least breaks even? Getting the money back that I had invested was in my mind a win. So I wasn't doing it to get into the hot startups. I wasn't doing it to try to build a track record so that I could become a professional investor later. I wasn't doing it because I had some belief that my ability to pick startups would beat an index fund. It was just this amazing moment where I realised I had finally reached a point of financial stability where I could cut a small check to a friend without worrying too much.

In retrospect, it turned out fine financially. But I think what was even more illuminating was that it helped me learn in parallel, and I really value experiences or opportunities that allow you to increase the amount of information you can take in and the learning you get from it.

One of the things we look for in startups we back is just how quickly we think they iterate and learn. Not like: Well, tell me what milestones you’re are at. I care almost less about that and much more about the velocity and trajectory. A team that learns and iterates quickly can solve a lot of problems over time. And one that moves slower and deliberately can sometimes fall victim to being too methodical and find themselves with a lack of time, resources, and morale to go slow.

VFD: Yeah, it's kind of part of that chaos that people get addicted to in startups, right? If you're in an environment where it's just so quick, and you've just got to keep moving and not stop iterating and just hope it works.

Hunter Walk: Sometimes people hear that and they’re like: oh, that's ‘move fast and break things’, right?

VFD: Yeah,

Hunter Walk: But actually, one of the reasons that we have taken the investment model we've taken – which is concentrated early stage work with the team – is because we actually believe those earliest stages aren't just about getting to the next funding round as quickly as possible.

I think smart people can usually figure out how to will themselves from A to B. But what I rather they figure out is who they actually are as a company. Start to set their culture there, bring on the right people, and learn enough to build the infrastructure that's going to help them not just raise the next round, but be successful post that raise, too.

So sometimes we do ask people: Hey, you've got your first 10 customers and they don't fit any one particular customer profile. They're just a hodgepodge. That’s great that you got to 10. But from 10 to 100 you need to have a customer persona, you need to understand how you're going to reach them, and you need to understand who your buyer is. And the more similar they look, in some ways, the easier that's going to be. So before we go out and try to raise that next round, let's start to do some work.

And that’s not just tapping your friend network to get people to use your product. But let’s start to build the muscle out for paid acquisition. Let's start to build a muscle out for a sales cycle. Because you're gonna have to answer some of these questions in your investment meetings. But even if you didn't, even if somebody would just hand you a cheque without asking any of these questions, the moment that cheque clears you're gonna have to start growing – and growing faster than you have already. And if you don't know how to do that it gets very hard to change the engine mid-flight.

So I like to make sure that people are patient and figure out what they want to get right. Not just: Well, somebody wants to give us more money, we should take it. That’s not always the right way. And that's a little bit contrarian, I'd say, as to where the markets are these days where there's a lot of capital velocity. And it's not one size fits all advice.

There are certain companies and certain founders who I think can then use that capital in very productive ways, even maybe ahead of having figured out everything they need to about their company. But my median answer is not: is that capital ready to be offered to you? But: are you ready to take that capital?

VFD: It’s a good question. Do you get jealous of being around these people and these companies now that you’re not on the tools as much. Does it ever come into your mind: Maybe I should just park this for a little while and start something up again…

Hunter Walk: No, I think if we hadn't done Homebrew…

My partner Satya and I started Homebrew but we had worked together in the mid 2000s and had always wanted to work together again. He was running product at Twitter, left there around the time that I was thinking about leaving YouTube, and all of a sudden we had that blank sheet of paper to decide what we wanted to do.

I think if we hadn't done Homebrew he would have still had interest in building. But I was sort of ready to move away, and I don't get that operator itch that you asked about. I think it’s for two reasons:

One: I feel great about how I left. I accomplished a bunch of the things that YouTube and I wanted to accomplish. Certainly not everything. And in hindsight, I had some blind spots, and there are things I would have wanted to do more of, or differently. But overall I felt really good about my tour of duty.

And then second: building Homebrew – even though I would never compare a small venture firm to a startup in the sense that founders have it much harder – but a lot of the questions we were asking ourselves, especially in the first five years, were much more similar to the questions that our founders were asking themselves than maybe some of our co-investors who had been in business for 10, 20, or 30 years at established multi-billion dollar firms.

And so I didn't feel like I was “playing entrepreneur”. But I did feel that feeling of ownership, that feeling of making decisions and then seeing if you're right or wrong, that feeling of representing something.

If myself and my partner agreed on it, we went and did it. If we disagreed on it, we didn't do it. Everything from making investments, to who we took money from, to our voice in the marketplace and what we stand for, to the things that we believe in. Some folks might be more hesitant to do all of that.

And being in the seat of the investor as opposed to somebody who's building hands-on helped to incrementally satisfy some of that. If I was just a cheque writer – if I was just a banker – I don't think that would be satisfying to me. It's not a derisive statement. There's plenty of people who I think love the spreadsheet and love the economics of it first and foremost. But for me, the investing was just the business model that would allow me to spend my time the way I wanted it.

I always get “means to an end” and “ends to a mean” confused, but it's the one that’s meant to be like: it was my mechanism to get to spend my time the way I wanted it.

VFD: I’m racing through my head now wondering if I’ve had it wrong my whole life.

Hunter Walk: Yeah, it’s a bad one. It’s the type of expression where you're literally saying the opposite of what you intended to if you use it the wrong way.

VFD: Definitely. OK, well, we've jumped ahead a little bit. I wanted to loop back: you mentioned Google a few times. But where did you grow up? In San Francisco?

Hunter Walk: No, I'm originally from the New York City suburbs: Queens and then Long Island, which is just to the east of Queens. I moved out here in 1998 for grad school, so I've been out here since then. But I'm an East Coast Jew. That's where I always feel most at home.

VFD: What was it like growing up there?

Hunter Walk: It was interesting. I have a younger sister and we’ve both had a similar upbringing but reacted in different ways. She stayed in New York and is now in Westchester – she likes the suburbs and I liked Manhattan. So I have always wanted to continue living in cities.

My wife, who's also from New York and Texas… We met in California but we both moved 2500 miles away from our families in our early ‘20s for a reason. But then we realised as we got older, especially once we had kids, how important they are and how much we love being near them, we just still find ourselves 2500 miles away.

So I think what emerged from that experience was an appreciation for the density of, and movement of, urban environments. I grew up in a very homogenous suburb, so I tried to seek different versions of more heterogeneous communities. I went to Vassar, for undergrad, which used to be a women's school but was still only about 35% male. But when an institution is built for somebody other than you, you can tell by the pictures on the walls and by its history. I worked for women, had female managers in my first job all the time, and I joined the women in management club at Stanford Business School. I was the the only guy who asked to join the Women's Club.

And then, of course, in San Francisco itself I just continue to try to give myself the experience of not being always in the structural majority. Because in my upbringing I just… was. I was in a town that was heavily, heavily Jewish, and that gave me a good sense of community and identity. But it also narrowing what my world looked like.

VFD: Yeah, definitely. And so you move across the ‘States to go to college?

Hunter Walk: Yeah, to go to graduate school. I got a history degree from Vassar, which is about 90 minutes or two hours north of New York City.

I enjoy writing. And I enjoy stories. So I thought I was going to be an English major. But when I got to Vassar and started taking the intro level 101 courses I realised that history, or the study of history, can be very different than what I'd been exposed to in high school. I felt like high school history was names, dates, and wars. And Vassar gave me licence to explore history as stories. So it was a cultural view of why things were happening. And I specifically focused on 19th century American history, which was the formation of a truly American culture that was informed by, but separate from, its European heritage. And I loved that aspect of it. So I realised that the stories that I was most excited about wasn’t necessarily fiction, but was nonfiction, and was looking backwards as opposed to forwards. And I enjoyed learning about those stories and telling my version of them.

VFD: What was your plan on getting a degree in history? And sorry if this sounds very tepid and two dimensional, but was it working at a museum? Or being a lecturer? What was it that you were going for?

Hunter Walk: I wasn't initially thinking that it would lead to a particular profession. I was thinking that I was enjoying what I was doing, I was learning how to learn, and I was gathering disparate skills. I ended up doing Summer internships that were more professional focused. Like: oh, you're going to work at an advertising agency. Oh, you’re going to work at a TV network. Those things felt like I was road testing careers. But the history degree didn’t feel like I was making a line between that degree and then teaching history or working in a museum.

I'm 47. So this was, I guess, mid-’90s. And it was weird, because if you weren't doing a specific, professional degree or you were going to be a teacher, you were following a science degree into the sciences or you were following an art degree into the arts. The “professional” careers that you chose from were banking or consulting. It was very narrow. Kids today have a much broader view of what's available to them, and I knew I didn't want to do banking. So then I went and did management consulting for a few years.

VFD: Right

Hunter Walk: And that’s what led me to decide I didn’t want to be a management consultant.

VFD: Hahaha, yeah, how were you even confident that you had that skillset?

Hunter Walk: Oh, I wasn’t confident that I had that skill set. I mean, I didn't know how to use Excel… so they had to teach me a few things.

The way it was portrayed to me was that the skill set you need is versatility, quick learning, and good communication skills. So I felt comfortable in those areas.

But I didn't assume that I was going to be successful. I just assumed that I needed to pay my rent. And the fact that it was a three year programme made it a bit like: OK, this may not be the right choice, but I won't get stuck here. Because even if they love me, they're gonna kick me out.

So it had an expiration date. And I liked that I felt like I could get exposure to “business” and then decide whether business was right for me or not, or go back to something that was definitely not business.

The Freud On A Couch thing for me is: my parents are both retired. My mother was an artist and art teacher, my father had a more traditional business. And so, up until my early to mid-20s, I just kept telling myself I had to figure out which one of them I was. Like I could only be either creative or business-oriented. And then finally I decided that maybe that was the wrong way to think about it. Like: Actually, maybe I’m a little bit of both of them and a little bit of my own self.

VFD: Yeah, really crazy that it works that way.

Hunter Walk: Yeah, crazy that that's actually how it works. But that gave me the confidence to merge my personal and professional sides. Like, my work wasn't gonna just be something I did during daylight hours. I was willing to commit myself to working on things that I cared about, with people I respected, and to say “no” to things that were clearly “good jobs” but that weren’t where I felt like I could be my most fulfilled, most passionate, or most engaged.

VFD: Right? So you've realised that consultancy is not for you, you're in your mid ‘20s, and you decide…

Hunter Walk: They kick me out. And what all these consulting programmes do is they try to get you to a business school and then come back and bring some of your classmates with you. So they do a really good job of introducing you to the different schools. I was generally ambivalent about the idea of an MBA – it's a professional degree, right? And if anything I was intrigued by the PhD programmes where you actually get to learn and study theory, not just memorise theory and application of that theory.

But Stanford was the one school that intrigued me for two reasons. First: I had been doing a consulting project out here, so I was in San Francisco for about six months and I really enjoyed the area. And then second: I was attending a panel that my consulting firm had put on where you're learning about all the different schools. One of the panels that they put on was with the admission directors of a few different schools, all wonderful programmes that are considered high quality MBAs. And the question that somebody asked from the audience was: if I apply this year, but I don't get in, would you suggest I apply again next year?

I don't remember the exact schools, but let's say Harvard, MIT, Chicago… they all gave versions of “Yes, of course, we'd love to see your applications.” And then the admissions director from Stanford, who was the sitting at the end, she paused and was like: If you didn't do anything new - if you just stayed in the same job and didn't do anything new that third year - then, like, No! You probably shouldn't reapply. Essentially, the idea that if you are static as an individual and you're just wondering whether the numbers game will work for you the next year? No. But if you're dynamic as an individual, and you've changed and evolved as a person, and you want to retell your story to us, then yes.

And I was just like: damn it. I love that. Let’s challenge folks with honesty as opposed to the easy answer, which was: Apply! And as I looked into it a little bit more, part of what Stanford is was very focused on the idea that in the best case scenario we're not just teaching you to be successful in your profession, we're trying to help you as a person, right? Like, there's a lot of leadership courses, and a lot of self development.

And I was like: Man, that's what I like. The idea that going through this period is not just spending two years acquiring skills, but trying to figure out who you are, challenge yourself, develop yourself as a person, and come out the other side with somebody who has more clarity about the way they want to navigate the world – starting with the work they want to do.

So I applied and I sort of said: OK, this is my test. If I get in, I'll go. And if I don't get in, that's the universe telling me that business is not for me and I should go back to something more creative.

And as fate would have it, I got in. I went. And in some ways I closed the door on being “creative” for a living, even though I think that side of me has served me well and has been serviced by the projects that I've had the privilege of working on.

VFD: It’s a fluid concept, right: Creativity. We probably don't do a good enough job of allocating it to anything that isn't painting and drawing and doing the more traditional things.

Hunter Walk: I spent my 12 years pre-Homebrew in various aspects of what you would now call the “creator economy.” Because my introduction to the PC wasn't command line programming, it was desktop publishing and graphic design, both through my mother and through being a newspaper geek in middle school. I'm old enough that when I was a kid you we were literally laying out the newspaper and taking it to the printer. And then by college, it was obviously all digital.

It’s like the thing Malcolm Gladwell talks about but it's not just the 10,000 hours, it's about when they occur. Being at a liberal arts college from 1991-1995 was a really interesting time because we had a high speed connection and we had a local area network and we had an internet connection. We had email, we had a non graphical and a graphical browser… I was exposed as a kid who just loved to learn and who was an introvert in real life but an extrovert behind the keyboard. I got to see what online community looked like. And I just said: Man, this is it for me.

So the stuff I worked on was always in this virtuous cycle of technology helping individuals be more creative. One of the purest forms of that creativity happens online and not offline, and in a community for both audience and collaboration. And then – here's the business side – I always believe that creativity doesn't have to be about economics, but if you deny people the right to see economic benefit from their creativity you are leaving a strategic opening in your product or platform for somebody else. If you’re not allowing them to dedicate their full selves because they need the job alongside the creativity – at worst you’re exploiting them.

Just being like: Hey look at the top of the Maslow hierarchy. Isn’t that nice? Don't look at the bottom: food, water, shelter, safety, security. Instead, we're just gonna give you the endorphin rush of somebody clicking “like” on your post.

VFD: Feels good!

Hunter Walk: Don't worry about the money!

I always believe that: no, you have to allow people to decide when they want to turn their creativity into into dollars. Not force them to – sometimes creativity can just be about expression – but give them that option.

VFD: So when you when you mentioned that you'd been part of the creation of this “creator economy” without realising it – is that in your time at Google?

Hunter Walk: No, I was at this pretty cool startup I worked at before Google. It was a company called Linden Lab that built a virtual world called Second Life. Zuck’s “meta-verse”.

But it predated Roblox and Minecraft and all this very interesting stuff. It finally sold at the end of last year to a small private equity group, but had been around a while. It was just this profitable, ongoing company that never became the 3D internet that some people had heralded, but was definitely very influential in what it explored. It allowed people to code in-game, so you could give objects properties that weren't created by the world builders ourselves. You could design things in Photoshop: your avatars, your clothing, and import it in. It had a virtual currency: the Linden dollar.

When you talk to different people who have innovated in social networks or who innovated in virtual currencies or who have innovated in continuous creative spaces, and a lot of them will refer to the work we did as being quite influential. But economically, we walked so they could run those companies into multibillion dollar things.

But it was amazing. Parts of it were fantastic in the moment, parts of it I wish I had been able to enjoy more. In retrospect, the reason I didn't enjoy parts of it was because of the pressure I was putting on myself and some notion of what it means to be successful in Silicon Valley, especially as a non-engineer. But all in all, it turned out to be a great place for me to spend three years, and then when the time was right, a great place for me to leave and go join Google.

VFD: I want to hear more about what you just said there about what it means to be successful as a “non-engineer”. Actually, it sounds like you didn’t change the way you thought – it’s just a hindsight thing.

Hunter Walk: I mean, yes. Therapy and maturity helped me in the years to come.

Y’know, my father had chosen an industry for his career that was great until it wasn't, and then once it started contracting and getting downsized he got laid off and never really found a way…

VFD: What was it that he did?

Hunter Walk: Men’s dress clothing. Suits and ties.

VFD: Right.

Hunter Walk: And I had a loving father. I can't claim real hardship, we were never poor. I was never poor but I was broke at times, y’know what I mean?

VFD: Yeah,

Hunter Walk: And so I had later realised that I was living with this fear of: there's a failure tiger, professionally, that's chasing me. And eventually it will catch me. And my job is to just stay a few steps ahead of it long enough to survive.

And my view of that in terms of what I decided coming out of grad school was to make an authentic choice. To go work for a startup that is working on something you believe in and that you think is really interesting and smart people are interested in, and then you can make a difference.

But when it became clear that it was going to be something, but not a rocket ship, not: oh, this is going to probably touch maximum 5 million people. Not 50 million, not 500 million people. I started to worry that the failure Tiger was speeding up and I was slowing down. Because how was I going to explain that? Obviously, the technology was amazing, but I didn't build that. I was supposed to be building the product and building the business model and building the partnerships. So if it wasn't a resounding success, how would I find my next job? And eventually the failure tiger would overwhelm me and I wouldn't be recognised as smart by my peers and I wouldn't be able to provide for a family and that type of stuff.

And what I only realised a little bit later was two things: first, that the failure tiger is my own creation.

VFD: It’s a good metaphor, I like it.

Hunter Walk: Although I still look over my shoulder every once in a while. And second, and maybe we could talk about whether this is still true today, but: Silicon Valley is very tolerant of what I call “smart failures”. Things that didn't quite work or were too early but very ambitious, very audacious, built with smart people and considered to be worthy, right? And if you didn't compromise your ethics or values during that period and you didn't do anything that's made people be like: oh you can’t trust that guy… I mean maybe even that can be forgiven.

But you can do a few of those and people will be OK. It’s a neutral not a positive, right? Whereas I had seen this fact that we had taken this big swing, and it wasn't perfect, as a blotch on my record. But it was something people were interested in and are still interested in. So that was all kind of self-imposed.

It’s one of the things I try to do whenever I give career advice. I talk about separating the quality of the decision from the quality of the outcome, and that it's more important to believe in the quality of your decision and then help manage to the outcome. A career where you're making lots of good decisions and have a mixture of outcomes will still be wonderful. But if you lose your way on the decision making, you are more likely to not end up where you wanted to be. And so just trying to give people the confidence to say “no” and know that this is the right decision, and then shut out the noise. Shut out what your roommates are doing, shut out the fact that you turned down being the second employee at whatever company, because the environment that we're a part of is very toxic, I think, when it comes to comparing yourself to the aggregate success of others.

VFD: It’s very easy to do, right?

Hunter Walk: Sometimes it can be instructive, and sometimes it can be helpful and open your eyes to opportunities. But I think that ultimately people should be the best version of themselves. And the more you understand who you are, and what you want to do, those are priorities that change and shift over time. So it's fluid – but I think that’s where happiness comes from. And so I was lucky enough to find my way into the tech community in the late ‘90s, and also to make a few good choices here and there. I made a few good decisions, some of which had good outcomes. And I also got the benefit of the doubt because I'm a tall, straight, white male who did grad school at Stanford and worked at Google. So I pattern match pretty well.

VFD: Yeah.

Hunter Walk: There’s this new thing we're doing called Screen Door, which is meant to fund new VCs who come from underrepresented backgrounds. I'm trying to create competitors who look less like me. Because I think that's what the technology and the community I love needs more of. And less of me, going forward.

I benefited so much from the people who helped me get to where I wanted to go. I want to try to do the same, and I'm just starting to realise that I can do it, more than just taking a coffee meeting with somebody to give them advice, but I can do it at a structural level.

VFD: It’s kind of that single player vs. multiplayer thing again, right? But in a different context.

So Second Life - you went through that. And then it was Google following there?

Hunter Walk: Yeah, I worked on two products at Google. I came on to work on the early AdSense team.

VFD: What year was that?

Hunter Walk: 2003.

VFD: OK, so Google is starting to find its legs.

Hunter Walk: It was a little bit over 1000 people. You can always sort of do it by products. They hadn't released Gmail, they hadn't released Maps. It was essentially Search, right? Search with some ad products. Obviously very good search.

What attracted me to that, again, was the idea that the web is a publishing tool. I had fallen in love with blogging and publishing websites. Google was, especially through PageRank and Search, it was like: if your content was really good, you could rank above more expensive, more name-brand content. And I loved web rings, I just love the idea that you could find a topic you cared about and you have this curated set of sites. Like a “Buffy the Vampire Slayer” webring. I want that back.

So I got intrigued by the idea that one of the challenges for this middle/long tail of sites was that the business model for them absolutely sucked at the time. You had punch the monkey banner ads, which were a race to the bottom, and those increasingly didn't provide great economic value. You could do popunders, popovers, all these things that were fundamentally at odds with the user experience. Let alone Spyware and stuff like that. And I loved the idea that Google was trying to build a model that would do non-invasive, contextually relevant ads and you didn't have to learn anything other than how to put some JavaScript on your page.

You didn't have to put on a suit and learn to pitch advertisers, you didn't have to get approval from anybody. You could be tiny, you could be big, it didn't matter. Once I got there, I saw that. Like: wow, this is real traffic and real dollars. These are real businesses publishing. This works.

And so for me – and I started talking a little bit before about that virtuous cycle – obviously, Google bought Blogger and stuff like that, but we weren't really involved at the time in those first two aspects. Like: let's help you be creative. And let's help you be creative with communities and audience.

I mean, Google Search drove audience but in a way that wasn't about editorial. It was more just about their best guess of what you're looking for. So that was very much, in my mind, the best answer to that third point, which was: how do we help people who are creative make money from their creativity? And AdSense felt like the best solution I'd seen in a very long time. So I went into that for a few years and that's where I met Satya, my partner at Homebrew, as well as a bunch of other wonderful, wonderful friends. And I did that for about three years, or maybe three and a half years.

VFD: And then from there… I thought you were at Google for longer?

Hunter Walk: I went over to YouTube.

VFD: Oh, right. OK. And was that when YouTube was purchased?

Hunter Walk: YouTube had just been acquired.

So YouTube got the acquisition closed, November 2006. And I essentially went over on January 1, 2007. I was thinking about leaving Google at the time. It had grown from 1000 to 12,000 people and it was starting to feel very big. I had been working on some video stuff that I thought now, maybe, was best left at YouTube if YouTube was becoming the centre of gravity for video at Google.

I'm very big about sticking the landing. I believe part of the role of product management isn't just to start something, but to finish your phase. And so rather than just making a decision about whether I was going to stay or not, and then letting somebody decide what they wanted to do with my product, I wanted to find my product a home or at least give it its best shot at finding a home before I moved on.

I didn't really know anybody at YouTube, but I found somebody over there, went over, and started talking to them about what I'd been doing. And the answer I got back was: I totally understand why you were working on this stuff from a Google perspective. Some of it could be interesting to us long term. But to be honest, we have a lot of stuff here we need to get done.

Y’know, YouTube was only 18 months old. It was 65 people growing very quickly. And it was like: have you thought about coming over here? And I honestly hadn't. But once that door got opened, and I spent some time with the founders and understood that Google was going to give it a certain degree of independence, which was really what I was hungering for, I went over there.

And then I stayed there until the end of 2012 or the beginning of 2013.

VFD: What did you do at YouTube?

Hunter Walk: I spent the majority of that time running the consumer product team, which you can sort of think about as everything on YouTube but the ads. I did the monetization for a little while, but that definitely happened after me.

I went over and I started working first on API's and the embedded player. So the YouTube outside of YouTube. Then I helped spin up the first mobile team.

There was an engineer and a business development colleague who were very prescient about how video was going to play out, and I believed them. And it seems so funny – we talk now about how could there have been some scepticism within YouTube or within Google that this was worth doing?

Well, we had to transcode the entire thing. It was expensive to be YouTube and to have mobile.

But we sort of felt that being the YouTube of mobile was going to be very valuable and very important. So we spun that up and we ended up making YouTube the only third party app on the first iPhone. There was a lot of good that came out of that, which in hindsight seems exactly correct. So we started that. And then that Spring, maybe Spring of 2007, the founders asked me to take responsibility for the product. And I did that for about five years or so.

VFD: Right. And this “creator economy” stuff - is this where you did that?

Hunter Walk: Yes. YouTube was early in that. I was certainly supportive of that, and certainly my background and AdSense helped. But I wasn't the only one. Chad, the CEO and co-founder, from day one he had talked about: if you can get TV sized audiences, you should get TV size dollars. He very much saw that vision.

So we had a small group of people within the company, including one very influential one, who really wanted to solve everything that would allow us to do that at scale. The most important point in solving that wasn't technical – Content ID helped us figure out do we believe this is original content, and can this be monetized. And having AdSense 20 miles away in Mountain View helped because we knew we could plug this thing in.

But I’ll tell you that the one thing that really helped move us was the acquisition of this small startup called Next New Networks. It was out of New York and it was half owned and operated video content - they were making and publishing their own stuff on YouTube - and half what was called back then a multi channel network. Bringing together different creators and helping them cross-promote. Bundling them into channels. All this type of stuff.

VFD: Smart.

Hunter Walk: And we acquired that group. And that instantly gave us critical mass of individuals with unique skill sets to Google: Audience development. Creator operations. All that type of stuff. And people who fundamentally believed that the YouTube native creators – people who had started creating on YouTube and not repurposed their clips from a primetime show or a sports league – would be the core differentiator and most important part of YouTube. And that's what helped move us forward. Before that it was a bunch of incremental things, but we lacked the critical mass of people who believed and who had the skill set to really double down.

And some of those people are still at Google, but that group has gone on to do amazing things. One of them is COO of TikTok. So these people have stayed within this general area and they continue to do amazing things. And it was such a joy to help with.

I tried to get that through that acquisition once and I couldn't get it through. But then there was some changes on the business side of the house and the new leadership saw the value in it and was willing to sponsor it. The reason I couldn't get it through was that the business side didn't really believe in that yet. And I wasn't acquiring any engineers. If it was just engineers I could have swung that in a day.

VFD: It was a content bet.

Hunter Walk: Yeah, I was trying to acquire people for somebody else's cost centre. And that never works if that cost centre disagrees with you. But that type of stuff was ultimately my downfall: not being political enough. But I felt like it was what was right. So we tried a second time – we had to pay a little bit more to bring them back to the table – but it worked and they became great friends.

I really think a lot of the stuff that they did, and we did at YouTube, was ahead of the curve and now informs what a lot of these platforms are catching up to try to do.

VFD: Yeah, I don't think it's an understatement to say YouTube is doing pretty well. It's a pretty big thing.

Hunter Walk: So I hear.

VFD: Yeah, it's around.

Well, thank you so much. I really appreciate it.

Hunter Walk: Thank you. I appreciate the invite. I'm honoured.