Ignite VC: Shaping the Future of Startups and Venture Capital with Kirby Winfield of Ascend VC | Ep41

Welcome back to the Ignite podcast. Today we're delighted to have Kirby Winfield on the show. He's the founder, founding general partner of Ascend vc. Kirby, thanks for coming on the show. We'd love to get an intro from you for the audience.

Yeah, absolutely. Thanks for having me. Brian. I'm born and raised in Seattle. I was like, you start at the, start at the beginning. Born and raised in Seattle.

One of the few, not many of.

Us, no, one of the few people left. I was going to say it used to be only us and, and now people look at me like I'm, you know, some sort of artifact when I say that. But yeah, was, was born and raised here and then went back east for college. Came back in 96 to help a friend with a startup which at the time we didn't even know what a startup was, but he created an Internet company and wanted me to help him and so was the sixth employee and ran marketing for the company and it was called GoTonet. It was a Web 1.0 portal that, that really was built around a semantic web search technology called MetaCrawler. It was kind of my introduction to AI, which ended up being kind of a through line in my career. We took that company public. It was an incredible outcome and it was a very forgiving time to be a 26 year old running marketing for a $4 billion company. And that was the kind of thing that happened all the time back then, apparently. No, And I think I managed to not screw up too badly because we got back together and started another company called Marchex in 2003 with the team, took that public in 04, did a $200 million secondary shortly thereafter and bought a portfolio of domain names that I ended up running as a business line owner. We grew that from about 5 million to 50 million in revenue using big data taxonomies. Again, like a little bit of AI. Took that company public. I left in 08 and I made the mistake, I always say, of thinking I mistook my good fortune for talent and thought, oh, I can probably just take companies public. It seems easy. These guys did it and I was there. So I took over a venture backed startup that had raised $18 million, quickly found out that, you know, I might have been better suited to picking the right founders to work for than to being one. And, and nonetheless, like slog through this thing, did a hard recap of the, of the business, laid off two thirds of the staff.

Oh man.

And really that was my introduction to venture capital. But we ended up selling the company successfully to comscore. So it was the big data analytics company that we sold sold to comscore. I ran corp dev at comscore for a year and a half and then.

You know, the retention kind of earn out kind of thing.

Yeah, no earn out, thank goodness. And the stock actually went on a huge run while we were there. But I launched the product globally that we integrated with comScore's product, new product line. It went to 100 million in two years. Just incredible. Yeah, we, you know, my technology founder had really built something special and I kind of rode his coattails through, through the, through the exit to a great, to a great outcome, actually post exit, but was ready to move on and so jumped back in, did one more startup again, two smart technical co founders with a great product who needed a business guy. And, and I jumped in and did a company called Dwellable, which we raised a couple million dollars for as a travel app maver on here locally and Boris at version one up in B.C. funded it and you know, we built the team, monetized it, you know, had hundreds of thousands of users, couldn't get the Series A, sold it to HomeAway a year later. Great outcome for investors. Pretty good outcome for the team and.

Nice little kind of pop there, early stage, 5 million cap kind of thing. 10 million cap. And sold it for how much?

Yeah, exactly, we sold it for 20 million.

Nice little quick 2 or 3 xer.

Yeah. And again, all credit to the technical team who founded it and created the solution and hired up a amazing group of folks who then just really fit into a gap that homeaway had on their mobile team. And so, and, and big kudos to that entire group for moving to Texas to get the deal done so that this time I was smart enough to realize I wasn't going to add much value post deal. And so I left right after we closed.

It.

Kind of looked at my career and gosh, you know, four startups, four outcomes. You know, the last two were the ones that I ran and I had to work really hard to just get, you know, decent returns.

Yeah.

And the first two, I picked these really smart founders to work with and had huge, huge returns. So I thought, man, maybe I should go back to like picking really smart founders because I'm not sure I'm built for this. I was, and I was beat down. I, you know, I had a young family and I'd never been there for them. I was always running startups.

Yeah.

You know, I was 50 pounds overweight, I was drinking too much, traveling too Much.

Yeah.

Not exercising. So I kind of did this whole life reset and I was really fortunate to have a very patient wife and got back to focusing on what was important for a little bit.

It's really the people we marry that make the biggest difference.

Oh, no.

I mean, just such a big difference.

No question. And I'm still 23 years in. I'm grateful every day because I don't think I would have made it without her. She. And I kind of got to reconnect and I got healthy and got my priorities straight and. And was like, gosh, you know, I'm not. I'm not done. I'm not much of a golfer. Like, what, you know, what can I be doing? Yeah, what do I like doing?

Right?

Like, you know, dude, I don't know. I had never asked myself that question in my life. Like, just.

Really?

Yeah.

No, you just kind of did the next thing and did the next thing.

Yeah, I always did what I thought I was supposed to do, whether it was what my parents thought I was supposed to do. Like, I wanted to be a dj. Like, that's what I wanted to do.

Well, run DMC poster, right?

There you go. But. Or, you know, we've got wild style up here. Nice going here. And like, you can't see all the other stuff. But yeah, I mean, I'm so cool. I wanted to be a dj, but that was like, there was just no way that was a viable path in, you know, especially my dad's eyes. And I thought it would be disrespectful to him to, like, pursue a career in music career and, you know, even music advertising. Like, I could have gone work for a label out of college in New York. Like, I could have done all these things. But I kind of said, I'm going to do advertising I'm going to do because that's what's expected and I think I might like it. And then you just wake up 20 years later and you've just done the thing that was next, the next big thing. And I thought I should run startups because that's what you do if you have success with your first couple of shots as an employee, you do it yourself and. Yeah, and then like, you do the next one and then. And so I just never paused to ask what I like doing or what I thought I was.

Actually. How old were you when you finally said that question to yourself?

I was 42.

Wow. 42.

Yeah. Yeah. Which just wasn't like something.

I think that's a magical number, right? That's the answer to life.

That's right.

42.

Jackie Robinson. I don't know. I feel like people come to those realizations earlier these days because there's just a much healthier.

I was 26. Yeah, I was 26. I worked really hard, grew up poor. I'm from Seattle as well. Shoreline, undergrad, all that stuff.

Yeah, yeah, yeah, yeah.

Shorecrest catalog, middle school, that whole area.

What was that? I went to Siree growing up.

Where is it?

I went to a school called Siree. We grew up unincorporated King County.

Oh, okay.

Which is now Richmond Beach.

Yeah, I know where that is. Yeah.

Well, I was 8 years old. Then we moved to the city.

But anyway, I was on the other side of the lake, basically.

Yep.

Shoreline, northwestern side of Lake Washington. But, you know, I worked really hard, got the finance degree, got the Wall street, cfa. Same experience. Like, I became disillusioned, actually. I was like, I hate this, actually. I don't want to do this. And so I kept asking myself, if I had 10 or 20 million in the bank, what would I do? I didn't have to work. Right. That was where you were at 42, where you're kind of like, well, I could just sit here and play golf, but really, what do I want to do?

You had the foresight to run the thought experiment before you got there, which is smart. And I had the blessing and the curse of having such amazing good fortune right on school that you could be tricked into thinking it doesn't really matter.

Trapped by your own success, kind of.

Yeah, yeah, you can. You're kind of like, well, why would I ask a question like that? It's clearly working. Yeah.

Everything's up into the right. With my career and my life and. Yeah.

So why am I gonna. You know, Becomes harder to switch. Anyway, so I. I was fortunate to have this time to kind of press pause and figured out, like, what I like doing and what I think I might be good at is working with founders and, you know, talking to them about their journeys and trying to be helpful. And, like, I've just, by virtue of sort of circumstance, had almost every good and bad experience that you can have as a founder. Thought that might be useful. And. And I. And look, I love. Somebody asked me earlier today, like, what's your favorite thing about your job? And it's. It's meeting with founders and that. Like, absolutely. It has to be. If you're a vc, like, I don't know what you're doing.

If you don't look forward to meeting with the founder, you should probably get out of the business.

Yeah. And just, just the fact that what I started to realize was I would meet with all these founders and as an angel, you know, very catch as catch can. But like, even founders where I was like, I hated the business and, you know, maybe I didn't even really think they were that awesome or, well fit to the problem, I always learned something I didn't know.

Yeah. Yeah.

I learned something about, you know, I learned something about software infrastructure. I learned something about, you know, foreign markets or I learned something, you know.

Yep.

And I thought, well, this is cool because, like, even when I'm losing, I win. Like, and, and it was just really, it was really kind of eye opening and I seemed to get good response from those folks. I always felt like I can impart, like one thing that might be useful.

Right.

And started angel investing with kind of an eye towards, you know, figuring out if there was space for me in the ecosystem, if there was, like, if I offered a product, you know, to the, to the founders, that was, that was not currently on the shelf. And in Seattle, as, you know, like, it's a really amazingly supportive and connected venture community, but it's very small and there aren't many options. And I come. My thing was like, look, there's vanilla, there's chocolate, there's strawberry. Like, I'm just over here trying to provide like, you know, rocky road, like a little different that maybe isn't for everyone, but the people who it's for it maybe really like it and people like the ice cream.

How long were you angel investing before you actually, you know, raised your first fund?

So I was angel investing full time from 16 to 19. Raised Fund 1 first closed in July of 2019. Along the way, got to help launch as an advisor only. Didn't do any real work, but helped launch the incubator program at the Allen Institute for Artificial Intelligence.

Oh, we just invested in one of those companies, HAL9. Do you know those guys?

Oh, Javier, yeah.

Javier, yeah. Love that he's on the podcast. I love that guy.

Yeah, he's the man. That's great. What a great investment.

Yeah.

And I still hang out at AI2 quite a bit, trying to be useful where I can be to the teams. But that was, that was a neat opportunity to kind of come in and sit with those folks as they were spinning things up and give them kind of a investor lens on things and, you know, and they let me hang out long enough and base my investing out of there long enough to where I built a little track record and had some investments go. Well, at the same time, I had a bunch of people I'd made money for in my four previous startups who.

Are like, dude, I don't throw some money at you.

Yeah, well, first they were like, dude, just stop showing me all your angel investments. I don't have time to think about these things. Yeah, they're basically like, hey, just do a fund, do a fund.

Yeah, I don't have time for this because I think people from outside looking in don't realize how much work this, this is. It's not as hard as starting a company and running a company, being a founder, but running a venture firm is actually a lot of work. It's different kind of work. Yeah.

Kind of work. I mean, you have like, I would say, like, you're never the single point of failure for anyone. Whereas when you're running a company, you are the single point of failure for every employee and every investor. Yeah, less so the investors because they have portfolio theory at play. Whereas when you're running, running a fund, you know, if I get hit by a bus tomorrow, like, founders will be bummed, but they'll keep building their company, they'll be fine.

And I guess that depends. Do you take board seats? How concentrated are you? What is your portfolio theory for your firm?

Yeah, yeah. So it launched in 19 and we're on fund too. We've made more than 80 investments. We invest in AI, ML and data B2B software, sort of. We think of it as just SaaS 3.0 really. The AI isn't what matters, it's what it allows you to do, solve problems for the enterprise. And so, yeah, that's the thesis. And we're, you know, we're pretty, we're pretty prolific. So my feeling is that because we're broadly, sorry I should say generally focused on, on the Seattle region. Yeah, you know, we don't want to be hyper concentrated because, well, Seattle is certainly on the rise. The thesis behind the fund is that over the last five years there have been $60 billion in outcome in this ecosystem where the previous 10 years there maybe was a quarter of that. And so we are starting to look a lot more like New York did in the auto.

It's kind of a flywheel spinning there with all of the startups and Amazon, Microsoft and.

Yeah, yeah, you get, you get the off ramps now. You've got growth, growth talent, you've got 30 unicorns, you've got people who've done it. We never had that before. You just had all these technologists trying to figure out how to get from A to D. And now you got people who've done it. So we do, you know, we do think there's a lot of density of outcome on the horizon, but it's not the Bay Area. And, and, and it, and it, you know, and that's okay. It shouldn't be that what it should be.

I think a big part of our thesis too is like there, there are unicorns everywhere.

Right.

There's 10,000 seed fundings a year. Roughly 100 over the long term become unicorns. And it's about 1 or 2%, depending on who you ask. I'd love to get your thoughts on this, but I feel like going forward, maybe there's a diaspora of unicorn creation happening outside of Silicon Valley. And I think you're describing what's happening in Seattle as kind of a.

Absolutely, that's the case. My only point with regards to portfolio construction was that. And you need more coverage if there are fewer per capita unicorns. And so that's why we.

Yeah, let's unpack that. What does that mean? More coverage?

So, so if I'm in the Bay Area and let's assume I'm in the top like quintile of investors with regards to access and deal flow and picking, I might be able to run a pretty concentrated strategy.

Yeah, I know which 20 I want to invest in because the odds are.

The graduation rates are way higher. The odds are way higher that you're going to see those things Mark, and eventually have good outcomes. That's just the numbers. I'm a Seattle booster and I believe that Seattle is an incredible place to find alpha, especially if you're an LP and you're not able to get into the top quintile funds in the bay with which 99% of LPs can't. Right, right. But the point is, if you're in Seattle, you know, if the frequency of, of outcome is slightly lower, like you just want to correct for that by having more swings.

Yeah, I love that. So I love to dig into that. I like this thesis, this portfolio construction theory, which is, let's assume there's a frequency of unicorns, it's below the average. Let's also assume that I'm not as good as I think I am. Right. I'm maybe not the top 20% VC. I'm maybe average or maybe I'm below average. A rational investor in this case wants to increase their volume of swings to maximize their chances of hitting an outlier. Is that how you're phrasing it.

Yeah, I love that. Yeah. Hopefully I am top quintile, but the only time will tell. And meanwhile. Yeah, meanwhile there's plenty of research to show you that in any geography, the sort of. The ideal portfolio at pre seed is about 50 companies.

Yeah. And I've actually looked at some research and I used to run Monte Carlos on loan portfolios back at Wall Street. If you run millions of simulations with statistical, you know, probabilities, distributions, you know, and precede and seed, you could, you can make a case that you should have even 100 or 150 or more.

Yeah.

And. Yeah. Yeah. So, you know, the rational. And there is a diminishing return, I think probably past 100, 150. But, you know, you think there's 10,000 seed investments every year. There's gotta be at least 500 that are probably pretty good, you know, worldwide, you know, and in Seattle, there's some fraction of that call.

That's right. That's right. Again, I think you can run the, you can run the, the, shall we say, like smaller check, more coverage model in a, in a market like Seattle, which I think is top five in the country, but is not number one. Yeah. Because. Because there's less surface area.

Yeah.

So. So, you know, so you can approximate. You're necessarily not indexing the market, but you can approximate some meaningful percentage coverage, which again, you would have to be YC to do it in the Valley.

Yeah. Do you often pinch yourself and think of how awesome it is to be a vc, how you stumbled upon this career?

All the time. I'm like, how, how did. A lot of times I just go, how did I survive, you know, my startup operating career? I mean, I barely did, to be totally honest, but like, I'm just so grateful to be doing something that I always tell people I'm working at the intersection of stuff I like and stuff I'm good at. And if it doesn't fall into those two buckets, it either gets outsourced or it doesn't get done. And that's just not a luxury that you have as a founder. As a founder, you often have to lean very heavily into the stuff that you don't like. But. But you know, fortunately, yeah.

As a vc, you could kind of hire people or contractors or whoever to outsource things you don't like to do.

Yeah. If I didn't have a chief of staff or in a back office outsourced back office firm and a fractional cfo, like, I probably wouldn't do this job because I'm Preternaturally allergic to, you know, administrative and finance. So, yeah, you just kind of pick. You try to. You try to put yourself in whatever, you know, your zone of, Your zone of goodness is.

I think that's generally good advice too, is if you find yourself doing something that you don't like doing and you can outsource it and you can delegate it or hire somebody to do it, you should. I had somebody on the podcast who was a unicorn founder, and I asked a question like, what's the best business advice you ever received? And I think you said along the lines of hire people to do. Do the things you don't want to do as soon as possible or the.

Things that are low leverage. I mean, we've had founders, like, reconciling books on a monthly basis, doing accounts receivable through like the seed post seed. And you know, I remember a founder once told me, I said, well, you know, hey, you know, what do we do last month in revenue? And you know, what's the. He says, well, may give you some broad strokes, but I'm still closing the books. You are closing the books. Yeah, there's some.

Raised $2 million. Like, what are you doing?

Yeah, but there is, you know, there's a certain founder. I was definitely this way where you're just like, oh, you want to. And you want to outwork everyone.

Yeah.

And sometimes that's just not the smartest way to pursue. Pursue or prosecute your. Your startup.

So did you return to your childhood.

Dream of becoming a dj, you know, over time? It's funny, I finally bought turntables in like 1997 and, and a mixer and started collecting, collecting vinyl, start buying vinyl. And so, yeah, I have, you know, I've gotten to play. I've played weddings. Like, I've really played a bunch of parties. And you know, I still threaten to, like, go try to get. Do a residency somewhere. I have enough friends where I could probably bring enough business where someone would let me set up and play records once a month. But maybe that may be, you know, that maybe one or two funds away. We'll see.

That's so much fun. Yeah, for me, it's. I'd love to be able to like, create hip hop beats and stuff like that. Growing up listening to I see the Run DMC poster and just growing up with hip hop, the 80s and 90s, like the classic era of hip hop, and just, Just be able to create some beats from that era, like in the DJ premiere, fashion, Dr. Dre fashion, any of those.

Like, well, you can do it now, right? I mean, you get Ableton and all these. All these Dawes and like. Yeah, if you're. If. If you're more technically inclined than I am. My problem is I still play vinyl. I didn't get serato. Like, I'm. I'm a Luddite when it comes to music, sadly.

You know what I realize about myself? It's interesting. It's like, what do I like to create? What comes naturally. Talking to you on this podcast is just natural for me. It is a process of creation, and I get to learn and learn about you and learn new things, and I like it. That's why I do the podcast. But I've sat down with Fruity Loops and Ableton, and I just can't get through the barrier of creation. I don't enjoy the beat making process. I've created some beats. They sound okay, but I'm not having fun just like writing songs on guitar. I can play, I like to strum, I can sing a little bit, but I don't like the struggle of the creation of it.

That's the perfect definition of a venture capitalist.

Yeah, yeah, exactly. I enjoy the creation, I enjoy talking about it, learning about it, but my mind wants to go to the next thing. And that's what makes me a good vc, I think, because I can surf chaos, go from company to company, and it's just constant context, switching and learning new things. But I don't like to dive deep on anything.

You're an executive producer? Yeah, executive producer.

Yeah, I'm executive producer. Kind of come in, seagull, shit all over everything and then fly out of there.

I mean, look, maybe you're brending some. You're bringing some record. You bring the sample. Maybe you bring a record or two.

And Michael, I like this sound, you know, Check this out.

Something like this. Yeah. Okay. Yeah, it is. It is funny. I'm the same way. I wish. I wish. I don't know, maybe that's not the right word, but I spent so much time. It's embarrassing how much time I spent playing video games growing up in college. And I don't. But I did when I had the time to put in my 10,000 hours making beats or DJing or. Right, yeah. I didn't spend that time doing that. I spent that.

You give me Mike Tyson's punch out. You give it to me. To this day, I can go all the way to Tyson without practically getting hit. And I learned to play that game almost 30 years ago. And I can just go in and Just my kids are like, whoa, dad, they can barely get past the first the minors with Piston Honda and stuff. And I'm all the way to Mike Tyson.

That's. That's really funny.

Yeah. I mean, all the muscle memory is still there.

It's, it's. It's incredible. What, what our brains are, you know, full of.

Capable of.

Yeah, Yeah. I. It probably. I always wonder what, like, I think I know the. The complete lyrics to like 10,000 hip hop songs. And I'm like, what, what. What is that space that's taken up by that? Like, what, what. What could that be used for?

Does your wife hate you when you respond with rap lyrics? Because my wife hates that. You know, I'll just take a. I'll. I'll just take something like a little phrase or a little. A little word and I'll just like return a rap lyric.

Yeah.

From 30 years ago.

That's. It's. It's. My wife used to listen to rap, but she's one of those that, like, you know, there were a bunch of people that used to and they stopped and like, maybe you're one. There's no, no grudge. But they stopped in like 94. And then my problem is I kept going. So now thank God for Twitter or I wouldn't know anyone who cares.

What are your top three rap groups? Hip hop groups. All time.

All time.

Yeah.

I mean, top five. Yeah. I don't know. Probably Gangstar, DJ Premier.

Yeah.

Tribe Called Quest.

Tribe's number one for me.

Yep, probably. Probably P Rock and Seal. Smooth. You know anyone like big Daddy Kane, BDP.

Yeah. So the early 90s, late 80s stuff.

Yeah. Black Moon beat nuts. Like I get second golden era. I really get with too. And then, you know, I think that became kind of a wasteland after 97.

And I. Yeah, I think black on both sides. Most Deaf was probably one of the last great hip hop albums that came out around 2000. Black Star.

You know, I. I felt that way and then I kind of re engaged with the music in like 2012 or so. And so sort of the okay Player era, like the blog era, got into Joey Badass.

Have you heard his.

Yeah, yep. Joey Badass and ASAP and like, and then I, you know, fashion. And now I'm big into your old Droog and Makami and. And the God Fahim and like.

Okay, yeah.

Cook and Soul is the most amazing producer I've heard since Pete Rock.

Okay.

So there's like, there's still a bunch.

Of still out there. Yeah, it hasn't died. It's just.

Yeah, yeah. And you just have to look for it or be, you know, be around it. Which is easier than ever now because of the Internet. You know, when I was growing up, like to be around it, you had to be around it.

Yeah.

And so it's, it's good. It's one of my, one of my excuses for being on Twitter still.

I love it. So you'll love this. So I get on with my old friends. We all known each other since elementary school or earlier in some cases. We'll play Rocket League together and we'll just play rap in the back.

Oh, that's great.

And so that's like me being a kid in my 40s, just returning to my 9 year old self.

Well, good for you for doing that.

Yeah, it's so much fun. Let's unpack. I would love to unpack the overweight Kirby drinking too much. Because I just came out of this period myself during COVID where I gained a bunch of weight and I was drinking every day and I'm like, what am I doing? Like, what was that kind of period like for you? And when was it like, oh, I got to make a change here.

You know, I mean, I think I was in the businesses I was running, the two startups I ran. Well, certainly, let's go back. Pretty much every startup I was, I was involved in, I was doing, you know, a lot of outbound. So I was, you know, out representing a company, traveling, doing deals, doing sales. I was digital media, which is kind of notoriously a, you know, hard driving, hard party.

And yeah, I worked at Rocket Fuel back in the day at tech.

So you know it.

So I know it. Yeah.

And you know, I go to London a lot, go to New York all the time and go to, you know, Monte Carlo and like all these crazy boom boondoggles and you just kind of get. That just becomes your lifestyle. And then you get home and you know, work till 8 o' clock at night and then I. It'd be too late to go home for dinner. So I just go to the, you know, restaurant, you know, drink wine and hang out and. And you just kind of getting this like all you're doing is going to work and then going out.

Yeah.

And it had kids and so fine. Like then you're going to work and going home. But you know, know when I have a nice glass of wine after a hard day and you open the bottle and so I think you just kind of get, you know, kind of gets away from you a Little bit. It got away from me. Yep. To where I just didn't feel great about, you know, I didn't feel great about my just who I, who, who I saw in the mirror.

Yeah.

You know, and kind of.

Yeah, I got to that point too where you know, having way too much, maybe even a bottle of wine every night and it's like looking at myself, I'm like I look old and I look puffy and I just look tired.

Yeah, I look fat.

You know like in.

Life's hard enough if you start.

Life's hard enough. Yeah.

Wake up. If you wake up with, with sort of two strikes against you. Like boy, you're spending the whole day trying to, trying to fight back. That's not, that's not a great way to be present, you know, as a leader as you know and I think so after the, so like after the third startup I got smarter about you know, sort of alcohol consumption and you know, being mindful. But I replaced it with ice cream.

Oh no.

So the good news is I was pretty clear headed the majority of the time I was running dwellable. Not to say that I wasn't you know, when I was running the other companies but yeah, just you know, I think I was in a better, better, a better place with how I was managing my day to day but probably gained, you know, another ten pounds because.

Oh man.

Yeah, I was like, well hey, I deserve this.

Yeah, I probably gained 50 pounds. I'm down about 25 now but I gained definitely 30 or 40 right in covet just shot right way.

Wow. Well, you look good man. Congrats on, congrats on managing it actually.

63 years old. No, I'm just joking.

Yeah, yeah, yeah, yeah. Do you have a blood boy? Right? You're um.

I'm 43. I'll be 44 in June. Um, but yeah, green tea every day, you know, lots of sleep. Get my exercise.

Sleep. Man, I wish someone had told me sleep and exercise. I didn't exercise for like the day I stopped playing football in college until like 2016. I basically did no exercise and played football in college. I did division three. So. And, but still play, playing is putting it pretty, pretty loosely. Right.

I was on the field, I was geared up, I was wearing uniform.

Um, I got, you know, it's good, it's good times. Some of the best times. Best friends, you know, still have the test with the guys and so it was a blast. But. But yeah, I just kind of. My thing was I always worked out so I could play football and so once that went away. That motivation went away. I was like, oh, well, why would I work out? And in 16, I kind of go up because I got to lose weight and started running. And now, of course, it got addicted to that because everything's binary in my.

Life, and so I'm the same way. Yeah, same way. It's. I'm a hundred percent in or a hundred percent out.

Yeah.

It's like all or nothing.

It's. It's hard. It's in. A blessing and a curse, I think. I think. I mean. Yeah. And of course, because I was. Got into running, then I started running, like, 12 miles a day sometimes, and I had friends, and I was running fast, and my friends were like, what are you doing? Are you training for something? And I was like, no, I just really like running. And they're like, you're going to hurt yourself. And I did. And then I got depressed and I gained weight. And so it's this whole kind of.

You know, finding the balance, you know. Yeah, it's really tough.

It's. It's tough, I think, putting family. I don't know if you found this, but for me, like, when I kind of reset and put my family first, it was really interesting. Like, this idea of putting my family first and then work, you know, would fill in as it came.

Yeah.

And as opposed to, what do they need?

How can I put them first in every situation and then work backwards from that?

I'm just broadly having that as a framework versus, like, I was always like, well, my job is the most important thing, and nobody cares about me if I don't have a job. That. That's important. So job first, and then if there's leftovers, it's for you guys. But switching that. What's happened is I used to. I had all the time in the world for family for, you know, a couple years, I was angel investing, and then. Then I did the funds, and slowly, slowly, slowly, there's less time for family.

Yeah.

But family's still at the top. It's still the priority. And so even if there's only an hour for family, that hour is super valuable. And I make sure that it's the time that works for everybody. And, like, you know, somehow it still feels like more time because it's still the priority. Like, if something has to give, it's always going to be work. Yeah, almost always. Sometimes it. Sometimes it has to be work. But, like, nine times out of 10, you know, the work can be managed into a space or time that's.

That doesn't What I've learned as working team ignite now full time is I kind of work a swing shift. I kind of work those, you know, three or four hours in the morning, three or four hours in the afternoon, maybe an hour or two in the evening and then I'll throw in the extra three or four hours once or twice on the weekend. And it kind of just, I really like that flexibility of, of being able to kind of work when it makes sense rather than having to go like into the office button seat, you know, for 10 hours a day or whatever it is.

Oh yeah. I mean it's the, it's the only reason I can work as much as I do and as hard as I do is because I can do it in that fashion. Like I get up at 5, 5:30 this morning. I was up at 4:30 for some reason. I'll just work. You'll get there, but I'll just work till you know, work till 8 and then I'll you know, bring my daughter to school and then I'll you know, go for my daily run and I don't schedule meetings till 11 and then I do meetings from 11 to 5, sometimes 4, 11 to 3, but whatever it is. And my, my thing is I love the weekends. There's certain type of work I do on the weekends and the weekends nobody needs anything from me and I can run later in the day. So weekends I work from you know, call it 5 to 10, 5 to 11. And it's just, it just feels, it just, it's because I want, it's what I want to be doing with my time and in the weekend treat is that there's like no meetings so I really get to work and I do.

The little blocks, you know, I block off. Okay, I'm going to take a walk here in the middle of the day because I know I need to like energy level is going to be low. So I'm going to go for a 20 minute walk at that hour, that half hour I block off an hour for lunch and I um, I work out. I have the tonal. Have you heard of this?

My buddy Rob Cony Bear at Shasta they did the series A I think amazing machine.

Like I cannot say enough about it. My wife got it for me for my birthday I guess almost two years ago now. And life changing just being able to go up there and just bang out a 15, 20 minute weight training just change your, change your life. So I work out every single day, usually, usually at lunch, do the protein shake, but then meditation, right. Meditating twice a day.

Yeah.

Trying to get that.

Too noisy. Too noisy. I know that you're not supposed to strive for nothingness, but I just haven't. Meditation and yoga are two things that I intellectually know would make my life better that I still don't do.

I never regret doing yoga, but I'm always resistant to doing it for some reason. I'm always like, ah, I could go work out, I can go for a run or a walk or blah blah, blah. And then I do the, I'm like, oh no, I said I would do yoga once a week, I'm gonna go do it. And at the end I'm like, gosh, I really like this.

Really? Yeah. I mean that's, I have people who I respect a lot who rave about it, but I'm addicted to running. It's such a, such a time bounded like I'll run six miles in 50 minutes or whatever and it's perfect, it just fits and I get what I get from it is so reliable and consistent.

Um, you gotta try weight training. Uh, are you doing weight training?

No, I went and saw a trainer and I know I should be doing weight train, should be doing body weight. I am very much, I have a very hard time doing new things and what. And once I do them, I, that's all I do. And so it's the 30 day thing. Yeah, I could do. If I could do the weight training for 30 days, I would do it every day for the rest of my life.

What I learned was, you know, the after 40 you lose about 1% of your muscle mass per year. And so you have to, you have to work out just to maintain your muscle mass. And it's also correlated to longevity. Right. The muscle mass I know I've had, you won't fall and break your hip, you know, because you have all the muscle.

No, and really when you turn 50 is when it really gets bad. So you're supposed. Yeah, I, I, it's, it's, I would say like. So a lot of times I don't know how you work, but like a lot of times I'm working on something without working on it and, and so it feels like procrastination, but it's just not time, it's not baked yet. Whatever the.

Yeah, yeah, yeah, yeah.

And so I've now like I did the step, you know, in December of engaging with a trainer. So like I feel like I'm working on it. Like I took a step towards, towards making it, making a, towards towards integrating new workout routines or towards Lifting weights, whatever it might be. So I trust myself. I've learned to trust myself. Which mistake in this case? But like I trust myself that when it's time, I'll do the thing. Yeah, certainly works for. It certainly works really well for work. Maybe less so for home stuff is my wife's like, why didn't you respond to that email? I'm like, well, it's not. Because it's not time yet.

It's there. I will respond.

Yeah, don't worry. I don't know. So maybe it's just an elaborate way of explaining my laziness.

So describe for me your perfect startup and it could be one that you invested in or, or just a theoretical perfect snowflake of a startup that comes across, you know, and you're just like, this is an easy. Yes, it checks all the boxes.

Yeah, sure. We announced today that it doesn't have to be real.

You don't have to say names if you don't want to.

Yeah, no, but actually it's, there's actually a really good example that, that is top of mind right now because they got their seed done today. We did the pre seed and then Bessemer and Juan Catalyst led the seed. It's a deep fake detection startup.

Oh, I heard about this one.

Clarity. Yeah, I met the founder, you know, 2017 or 18, you know, really charismatic guy. Didn't think about him again for four or five years. And then a friend of mine was working with him and said, hey, you should really talk to Michael. He has background in startups and specifically a little bit on the venture side. He's wicked smart. He's just a, he's the kind of person where after you meet him and you get off the phone with him, you just think to yourself, how do I, how can I be involved with this person?

How can I, should I sell my venture firm and go work for this person?

Right, right. And combining that with a market that's a complete, just wide open blue ocean that is going to absolutely explode in the next five years with no clear winner and you know, a couple.

I mean, it's almost like cyber security. Right. It's like looking at CrowdStrike probably 10 years ago. There's going to need somebody, there's going to, there's going to be a winner here.

That's right. In this area and maybe multiple winners. Like it is a massive, massive, massive problem space. So we invested, you know, whatever a year ago and as you've probably noticed, like deepfakes have become like huge issue.

I guess there's fake Trumps calling around people right now.

Trump's. There's now a problem that Clarity is working on around executive deep fake protection. You know, there were, if you saw in Hong Kong, but basically hackers made their way into a zoom and deep faked four executives from a company. The fifth person was a real employee of the company, thought the other four executives had apparently approved and directed them to wire $25 million out the door. They did it. They did it.

And so the money's gone. It's just gone.

Money's gone. And so.

Wow.

And so that can happen to real companies, right? And that's insane at any level. And so a lot of the conversation now is with, you know, for this company that we've invested in is with, you know, CSOs of banks, you know, in financial institutions.

And so now you have to run this deep fake software on top of all communication, basically.

Right. At all times.

You just never know at all times.

So it's got that intersection of an incredibly dynamic and charismatic founder who, you know, can raise money, a problem space that is nascent but, but you know, we bet that it would explode and you know, hopefully that's true. And, and you know, then a technical team and that's, that's a plus plus in a solution that's unique and defensible, which we think they have. They're all out of, you know, 80, 80, 200 and cyber warriors in Israel. And, and so, so that's kind of.

Like that founder market fit was off the charts amazing founder that you see ringing the NASDAQ bell someday, being the leader of the space, kind of checking all those boxes for you.

That's, that's one where, you know, and you know, ask me in, you know, seven years, but that at least has the profile of something where you're like when it, when it all kind of feels like it's going to be that, that's, that's great.

But so much of this early stage stuff, it is a feel, right?

It's totally because as you know, like a lot of times they don't look like that until they look like that.

And so, you know, I have plenty of those. Right.

Well, and the question, but you know, Court at Docusign will tell you, like Docusign didn't look like that for the first five years. Those guys didn't. Didn't look like that and that company didn't look like that. And everyone thought they were crazy. And so, you know, especially in this market, you, a lot of times we don't have that flashy founder, you don't have that person that presents as like a magical fundraiser. And so you got to try to unpack, like are they close to being that and are they so good at smelling the problem and like chasing it down? Is the market big enough that you're willing to underwrite a little bit of a stretch on, on one of those axes? Because we don't have the same density of like, you know, sizzle selling slickness that, that the Bay Area does. And I think that's actually a strength up here. Yeah, but it makes, it makes it, it does kind of change how you have to evaluate deals, especially at the earliest stage. It's not always as easy as it was with clarity to identify. Okay, yeah, this is, There aren't as many easy checks as you would like, I think.

Yeah, yeah. So you do a lot of AI investing. Like what are you excited about? I mean the steep fake thing is a great example. But what are some other trends and interesting things you think are happening in the present future?

Probably the infrastructure layer has been over invested. I think you're seeing, you know, that's, and I, and I think I felt that way for a little while now.

A lot of money chasing the third place, fourth place infrastructure layer startups. Yeah, yeah.

And I think, and I think a lot of AI for AI is, is too early and because you're either a really good practitioner and you'll build your own LLM evaluator or you know, you're a really big enterprise and you're not really spending money on AI. And so we've just been focused on like vertical SaaS. 3.0 is what we're calling it, but basically just, you know, AI native SaaS. We just invested in Patrick Thompson's company who was a founder who we had in Fund 1, who exited and he's now, you know, building, I will say just building something new and. But the idea is to basically disrupt a particular set of kind of marketing, sales, CRM automations by doing an AI native version of that. And when we think about AI native, we think about it both in terms of the integration of AI into the solution that is customer facing, but also the integration of AI into the fabric of the company itself.

Yeah, there's going to be a lot of incumbent SaaS that's disrupted I think in this next wave because AI is creating a new way of creation of SaaS. Right. And software is eating the world now. AI is eating software and I'm seeing a lot of startups, I'M sure you are too. Where they're like, oh yeah, we're going to go after this 10 year old SaaS platform that cannot, just can't do it in a modern way because they're just, they're just stuck in the way that it was 10 or 15 years ago.

Yeah. Now we had this conversation with the founder of the portfolio earlier today and they're like, they have found their way into a really interesting place where there are three incumbents in the space that they're in, which let's call it like it's an IPASS kind of solution. And they're all, you know, 10, 15, 20 years old. And it's, and it's just, it's just.

Like that was super modern, you know, back when cloud came out in the late 2000s and the multi tenant SaaS and you know, salesforce.com and blah blah, blah. And now they're starting to be stodgy, clunky old tech stacks and there's just new ways of creating that software and, and new ways of doing the business. Like I'm looking at an API company where there's all these API companies out there.

Yeah.

That are all built on like 5, 10, 15 year old technology that help you connect apps while they're using AI to automatically automagically do that for you. It just unlocks a whole different way of integrating APIs. You can just have AI do it and it just does it on the fly and adapts exactly to what you need when you need it. Rather than trying to like make you like kind of look at all the JSON and match everything up and get all the edge cases and send me the company. Yeah, it's a good one. I mean, yeah, we need to do more of that. I'll send you more deal flow and.

Yes, that's for sure.

But I could talk to you for another hour. I know we're at time. Thank you so much for coming on, Kirby. We'll definitely have you back on the pod at some point in the future. Thanks so much for coming on.

Yeah, Brian, this was awesome. Super enjoyed it and stoked to see you around town and do some deals together.

Let's do it. Thanks so much.

Thank you.