S8E12: Kirby Winfield

Hi, this is Shana, the CEO and Founder of Fuel Talent. One of the things I have loved most in my 25 year recruiting career has always been the stories that people tell. Stories of leadership, career choices, company ideas and team building. My inspiration for starting the what Fuels you podcast came from being curious about people's lives and wanting to help share their stories. What what path brought them to this place? What decisions did they make that led to failures and successes? Who influenced those decisions and what lessons were learned along the way? I hope you enjoy the what Fuels you podcast.

Today's guest on the what Fuels you podcast is Kirby Winfield. Kirby's a seasoned startup operator and angel investor. He is currently the founding General partner at Ascend vc, a pre seed stock stage venture fund investing in Marketplace, E Commerce, DTC and B2B software startups in the Pacific Northwest. Earlier in his career, Kirby was a founding team member and operating executive at back to back tech IPOs with GoToneNet and Marchex as well as a two time venture capital backed CEO. He is a Techstars mentor and passionate board member and board Chair electronic at Special Olympics of Washington where he helped bring the 2018 Special Olympics USA Games to Seattle. In his free time, Kirby coaches youth sports and enjoys running, tennis and traveling with his wife, son and daughter. Welcome Kirby.

Thanks so much for having me. I'm super excited.

Oh yeah, I'm psyched. Yeah, I love the headphones and that. I'm just learning right now that you're a dj because I'm huge into music and if I had known I would literally make you DJ for us. So that might be like two. That might make you. I might make you come back on for two.

Oh yeah. Or whenever we get together, live like, you know, get a cohort in here.

Cannot wait. Post Covid. Okay, so we're gonna let it rip with some rapid fire, starting with what is your favorite Special Olympics competition or event?

Oh man. So you know, my daughter Kate is 11 and has down syndrome and autism. She is my favorite athlete. Probably her best event is gymnastics. Her floor routines sometimes go off schedule, but she like freestyles and while that's frowned upon in gymnastics circles, I love watching it. So that's. That's probably my favorite. Yeah, she does swimming and basketball, soccer cheer and gymnastics. So she's probably busier than the rest of our family combined.

Little athlete. She picked it up from her dad. It sounds like. What is the first bucket list trip that you're going to take after Covid?

Oh man, that's a great question. You Know, I think we'll probably go to Germany. My son really is interested in. So he's in eighth grade. He's really interested in the German heritage on my wife's side of the family. And we've already knocked out, like, if you can't tell, I'm, you know, I'm 100% Irish and English and we've already knocked out those trips, so. Yeah. Maybe getting some exposure to that part of the world would be fun.

Yeah. I mean, I love Germany. Okay. What are your favorite three albums?

That's easy. Miles Davis, Kind of Blue, A Tribe Called Quest, Midnight Marauders, 100% and.

Gosh, Lauryn Hill.

No.

Miseducated.

No, my sister loves that album and I. There are a couple songs on there. But no, you know, I would probably say for number three with Van Halen, Never down.

Nice. You have an eclectic mix of taste. I like it.

Yeah, you should see. Yeah, you should see the record collection. It's definitely, definitely all over the place.

Nice. Are you old school DJ like you? You.

Oh, yeah, no, I never. Yeah. Yeah. I never went to Serato. So it's all just two technique 1200s and Pioneer Mixer.

And I love, I love that you're still doing that.

Yeah, yeah. Well, it keeps me. It keeps me engaged in new music too. Right. So I go out running, grab the latest. That's fun.

Yeah. What would you do with an extra hour in the day?

Wow. I would probably meet someone for coffee, like, so it's interesting. I have the extra hour now because I don't drive anywhere anymore. I don't go and meet. My thing was always I'm going to go to the entrepreneurs where they are. I don't want them to come, have to be in my space. Like, I want to go to them, which is great. And addresses a lot of the power imbalances. I used to really dislike about the investor entrepreneur relationship. But it costs a lot of time. So I was constantly driving around town and meeting people for coffee. Run it here and there. And I don't do that anymore, so I'm much more efficient. So I feel like I've got that extra time, which I use to go for a run every day and then spend that time with my family. But so if I had that extra hour, I'd probably go back to getting out.

And like, actually the in person connection is you kind of can't beat it. Yeah. And. And is there a job that you would do for no money?

I'd do this job. I mean, I'd invest for no Money I'd invest in founders for no money for sure. I basically did and almost still do. I don't take a very big fee on my fund. And as an angel, of course, you are essentially doing it for free. So, yeah, no, that's really something I've discovered in the last like four years. It's just how much I enjoy working with a founder on their idea and helping them sort of get out, just get out of their own way so that they can succeed. I'm much better at helping them do that than I was at doing it myself.

Well, your operating experience, I'm sure, comes in very handy of just learning what to do, what not to do, how to anticipate things before they happen. I'm sure you're great at that. What is a pet peeve.

Founders who don't number their slides? I mean, look, in the world, in the universe, there are so many things that I could say I get hang ups about, but I'll choose one that maybe is germane in this conversation. So, yeah, it's something I learned from one of my first investors, Bill Bryant, and it's such an obvious, it's such an obvious thing.

But yeah, I'm going to write that down. That's actually a good takeaway for any entrepreneurs who are listening.

It's huge because investors and the real, that's the nit, but the real learning, the up level from that is investors see thousands of decks and they see thousands of pitches. And your job partially as an entrepreneur is just to again, get out of your own way. Don't give, don't put friction into the process of the investor consuming your story and information. And so, yeah, like numbering slides.

Leave things that are not distracting from the messaging that you're trying to get, if that makes sense.

You got it, you got it, you're good.

Well, I always say that in interviews too. I'm like, you know, all these other things that people bring into an interview are distracting. And it's not like you're looking to not like the person. But usually that's what's happening in interviews. You're looking for gaps or holes. And same thing with investing. I'm sure you're listening to a pitch, you want to love it, but you're trying to poke holes at it.

That's a really astute observation, Shawna. I do think that the interview process or the hiring process is a lot like the investor founder relationship, especially at the earliest stage because you are making a bet on the team. And if you're the interviewee or the founder. Um, you know, part of. Part of what you're trying to do is. Is it's just not give the other person a reason to say no.

Right, Exactly. Exactly. So let's not distract them. So here's my last question on the rapid fire, and then we'll get into you and all things. Kirby, is there a hobby that you haven't pursued yet that you're like, I got to do this at some point?

Oh, man. I. There. Yeah, there are probably two. I'm staring back here. I have an Akai beat machine that I have not yet taught myself to use. So I'd love to get more into actually making music, making beats. I bought a dawn and thought I was going to mess around with, like, beat making podcasts. This was, you know, in, like, March and April of this year when I felt like I had time because the whole startup world kind of froze on the financing side. So I bought all this equipment, and now it just sits here.

So the beats will be your next hobby. I like it. What's the second one you said you had two.

Actually, I was thinking about it, doing a podcast.

Oh, nice.

Yeah. Not to be passe, because so many great people are already doing it, and who needs another one? But I found that, like, I've just stumbled through life into a lot of really interesting relationships and know a lot of interesting people who maybe don't have. Aren't inundated with requests to be on podcast, but who have stories to tell and voices that need to be heard and.

Yeah, and, you know, I would. I would listen. That's a really cool thing to take on.

Well, that's daunting, though.

And I, you know, I felt the same way, and I just literally did it without much thinking, and then I committed to putting it out once a week, which is the bigger thing.

Yeah.

Just don't. Don't put it on any sort of cadence, and then just do it when. When you feel like it. And I don't really know. I have never studied podcasts, but I just know they're fun, so I'd recommend it. We're having fun, right?

Yeah. This is not a blast. All right, good. Well, maybe I'll get you on my podcast.

We'll talk offline on it. Yeah. So tell me about you. I know you grew up here in Seattle, correct?

I did, yeah.

And tell me about your childhood. Are you one of many kids, an only child?

Yeah, One of two kids. Younger sister, who actually, I'm excited for her. She's at Airbnb, and They just filed to go public.

Oh, nice. Plus she likes Lauryn Hill.

She likes Lauryn Hill, so it's funny. So she's actually, she's my younger sister. She was always the more intellectually curious, self motivated, good kid. Went to Lakeside, then went to Reed for college and kind of just totally made up her own major. And I was more the. I was a troublemaker. And when I was a kid, I too was. Went to the Lakeside entrance exam. And for those who don't know, Lakeside is like this prestigious high school in Seattle where Bill Gates went and what have you. And I went, oh my gosh, that's right. So Bill Gates and Shauna Sperwland and then like some other chumps and my sister. But I got in a fistfight at the entrance exam in sixth grade.

Oh, that's nice.

What my dad has said in recent years is, yeah, that was you saying you didn't want to go to Lakeside. And so I had my.

Well, it sounds like you figured it out, Kirby, because you ended up at Middlebury, which is a fabulous well.

And the only reason I did that is because I went to Seattle prep for high school and the Jesuits put me in line. And in all seriousness, that. That was like the perfect fit for me at the time. I was, you know, I was definitely like, I didn't like authority and had a chip on my shoulder and wasn't maximizing my potential in junior high. Switched over, went to prep and sort of turned it around and had a great experience there. Met and actually met the younger sister of who would become my first boss in the startup world. So, you know, if I had gone elsewhere, who knows?

Yeah, it's always interesting, like sliding doors, part of life where you're like, what if I hadn't done that? Where would my mouth be? It's always so interesting. So you said that you had a chip on your shoulder. I've interviewed so many people who say that and I'm always curious, like, is that a motivator for you? Is it. Does that still drive you?

No.

Did somebody doubt you when you were little? Like, where does that come from?

Yeah, I think it came from just, you know, being, being a firstborn and having my dad be a very. He was still, still with us, but as a professional. He was a radiologist and you know, was part of some private practice here. They bought like the first MRI machines in Seattle and he was very much straight ahead, like super high expectations.

So you're supposed to follow in his footsteps.

And you were like, maybe, maybe not into Medicine. But I think just, you know, he was an Ivy League guy and like this and that. And there was just. The expectations were really high and, like, there wasn't a lot of room for. Not performing. And so I think that was really. That's really good. Like, he instilled this idea in me. Like, you know, you just show up first, leave last, work harder than anyone and ask for more, and that'll put you ahead of 99% of people. And he said that. And I always. That always stuck with me. He's right. But the problem is, I think that's.

I think that's. I said we don't need any sound bites, but I think that's a good one. You have to say that again. I loved it. So you're saying, come in earlier, leave later, and work harder than everyone else and you'll always. It's 100% true.

Yeah, yeah. And he said, and ask for more when you're done. Right.

Ask for more. And. Are you saying this to your own kids?

So we're, you know, we're not there yet, but. But the problem is. So the problem is. He's right. That'll get you in front of 99% of people. But then once you're in that 1% of people as a high performer, basically, that just means you're like, at this point, that just means you're a worker in the knowledge economy. Like, it's not. Whatever. Maybe you're in some.

Right. It doesn't necessarily bring you joy.

No, it doesn't. And so what do you do once you're there? And I think that's what I really struggled with professionally. Like, I knew how to get in the door and I knew how to, like, sort of make my mark, but I struggle with motivation, you know, beyond that external thing. So. Yeah, well.

And there's also a lot of people, and you strike me as one of them that needs to be. To have a purpose and have passion and not just a paycheck. Like, that doesn't seem to be your driver. It seems to be more being creative and driving an idea more than just like, oh, I'll just go to work and go through the motions.

I think I just mean I've always liked doing startups because that aspect of extreme risk and extreme reward and much like in the type, I guess, whether you're black, you can play strategy, count cards, sports betting, you can handicap and pick where you think you have edge. In startups as well, you have a certain amount of influence over the outcome. It's A game of skill, but it is also still a game of chance. And that, that combination really is compelling to me. And.

And are you competitive?

Yeah. Oh, yeah. I mean, I've, I can, I've played.

I don't know why. Did you play sports growing up?

I did, yeah.

The running, tennis. Is that later?

That's, that's the old man stuff I do now. But I was, you know, I played lacrosse, football, and I actually played football through college. And yeah, competition is a big part of who I am. And I actually probably over indexed on competition in my early career, partially because we had very sort of alpha Wall street competitive cultures in the two first companies I was with.

Yeah, I want to hear more about those. So as a competitor, are you more likely to love to win or hate to lose?

It's funny because that's the question. When I was interviewing for the job that eventually became a CEO role at Expos, Bill Bryant, again, my first investor, asked me that question. And I knew the question was asked that there was a right answer.

Yeah, I was going to say, like, I don't know what the right answer.

But I didn't know what the right answer was. And so I just said what I feel, which is I hate to lose.

Yeah. And what did he say to that? I mean, which one was the right answer?

I don't remember. Probably. Probably. I love to win, but because, you know, loving to win means you're more willing to risk it all and you don't worry about the downside case where it's like, you hate to lose, you're gonna be conservative. To me, like, winning is the opposite of losing, and that's why it's great. So. And I've always been the kind of person who, like, I want to put in the work, I want to do everything I can so that, you know, if we take a loss, like, it's not out of a lack of diligence.

Right. You leave it all in the field and you can say like, I put it all in. And then if you lose, it's just like, yeah.

Whereas if you're like. Whereas if you're like, oh, no, I just love to win, well, you might just kind of show up and expect that to happen. Like, I feel like hate to lose is like a grinder.

Yeah, I completely agree. Yeah. So you ended up at Middlebury. You played college football, which is awesome. And what did you want to be after college?

So I was super clear on it. I was a creative writing minor and an English major. I wanted to go into advertising in New York City. And, you know, at that time, that meant, like, it wasn't quite Mad Men, but it wasn't Math Men. Like, it became. And, yeah. You know, so. So my idea was. Yeah. Like, somehow I had this idea that I'd write copy, but also be an account person. And, like, also, like, I didn't really know what the hell I was talking about.

I didn't even know that that job existed. And I think I'm a couple years older than you, but I don't think I had much exposure to ad agencies.

Yeah, it was weird, but now that.

I've seen Mad Men, I'm like, that looks like a sexy, fun business. And especially New York City, which, of course, I lived there for many years. And it's. That sounds really cool.

It's. No, it was, you know, it was a romanticized idea. Right. And it was like, I read a lot of John Cheever growing up or something like that. You know, my dad used to live in Manhattan, and so I had this, like, this romantic idea of what. What all that kind of could be.

Yeah.

So I did internships, you know, in the summers. And.

And how did you end up going into this, you know, founding team for Gotonet. How did that come to be?

So literally, one of the jobs I did one summer was my. I mentioned my friend Megan Keister from. From prep. She introduced me to her older brother John, who at the time was running, like, a, you know, physical software company where he would ship, you know, they'd ship these CD roms out, and he needed someone to write the marketing copy. And Megan was like, yeah, my buddy Kirby, he's a writer. And so John just reached out and I wrote a bunch of copy for his brochures and kind of thought nothing of it. He paid me a couple hundred bucks or whatever, and I just spent it on beer and went on my way. And then. Then I graduated in 96, moved to Manhattan, was working because I was completely unprepared and didn't deal with getting a job. I ended up at this giant PR firm. It's like an executive trainee, and hated it. John reached out and was like, hey, we're starting an Internet company, and you're a journalism major, right? And I was like, sure, I am. He's like, well, you have a writing sample. So I actually wrote, like, I made up these articles and faxed them to him, and he brought me on. I think I was the 10th employee. And I ran editorial and copy for this nascent web portal, which two months later, their head marketing Person left and they just promoted me to the marketing role and I ended up running marketing through the IPO and through.

What an incredible ride. What was that like as far as the funding? Was it bootstrapped or venture backed or how did that company grow?

It was bootstrapped. Russ was a cfo, a public company CFO of Wall street, but before that was like a rainmaker for a couple of banks when he was in college picking stocks. And so he had a really great understanding of the financial markets and specifically how to engineer public market equity fundraise. And so we went out in a sort of, I think it was called small business IPO quietly in 97 and used that, used that public stock to acquire a number of different companies that we eventually pulled together under the GoToNet umbrella and portal brand. A lot of other companies were popping as public stocks in 98 and we were not because we used it as this tool.

What was the business model? What exactly did GoTonet do?

As you used to explain, my father in law would always ask me, what the hell do you do? Say well, it's like a magazine, but it's on the Internet. And so you just sell, you know, you sell ad impressions and at the time, you know, you, you could sell those for a really high cost per thousand. We were one of the only profitable Internet companies back in the day. Eventually the street took, took onto that story and our stock popped.

And was there ever a dip, Kirby, or was it like pretty much a rocket ship the whole time?

Well, that's what I was trying to say. It wasn't a dip, but it felt like a dip because everyone else was, you know, up, you know, 100x during the time where we were flat. And so. But John and Russ and the team had this really thoughtful strategy around just building a profitable company and rolling up all of these assets to create this sort of juggernaut of Internet traffic. And we were I think at one time in the top 10 in terms of the amount of impressions we were running through our owned and operated websites. And so that paid off over time. We eventually did become a $4 billion company and ended up selling, I think for two and a half to InfoSpace in 2000.

Wow. I remember that at the time I was living in New York and slightly following Seattle because there was a part of me that was like, will I ever go back there and just kind of tracking what was happening? And I remember that being a huge story out of Seattle. What a cool experience for you. And so did that put you in a Position to obviously have the luxury of figuring out what do I really want to do. Did, you know, like, I got the bug now and I kind of want to keep going, or were you, like, maybe I'll go be a DJ or maybe I'll go travel?

Like, I felt. No, I felt like. So I felt like, you know, certainly I knew exactly how much good fortune I had had. Like, it was very clear to me, you know, even while we were there, kind of this idea of there were people who are concerned about buying and holding their options to avoid some extra tax versus, like, I'm at. And I was like, I'm just going to sell my stock. I never thought this would happen. And so fortunately had some breathing room after that to think about what to do. But Honestly, that was 2001, and you might remember the Mariners had a pretty good year that year. So I literally. That was like, my wife calls it the summer of Kirby. All I did was hang out with my buddies in the restaurant industry and go to Mariners games and hang out until all hours. So I kind of had. I kind of made up for lost time a little bit, you know, because Go to net was a, you know, real seven days a week, 14 hours a day job. Like, no vacations. It was.

And what was the culture like? And what did you take away from that culture as far as, like, how you wanted to create your own culture going forward?

Well, yeah, yeah, it's interesting. It was an incredibly intense, urgent, athletic type culture. So there was no. There wasn't a lot of room for reflection. You know, it took me a while to unlearn it. Like, It was kind of like, let's. I don't really care what's going on with you. What's going on is this company, like, if we're gonna make this work, this is the only thing that matters. We used to call go to that the girlfriend killer, because, like, literally, like, almost everyone went in with a girlfriend and, like, immediately that relationship died.

What do you think? I mean, that's got. To me, that feels like more of a New York mentality, that kind of living to work versus working to live, which feels a little bit more Seattle. And also nowadays, I'm not saying it's fluffy, but everybody focuses so much on culture and mental health and taking care of employees. And this is like a little bit more dog eat dog. Like, get on or get off.

Yeah, that's right. And, you know, that's. Although I think that's a Valley thing now, too. I used to have Valley investors tell me, oh, Seattle, that's where you guys don't work that hard.

Right?

Like, and look, I think it's not for everybody, and it's not for everybody in every stage of their lives. So I would say it was definitely for me then, like, what else was I going to be doing?

No, I totally agree.

It's like a constructive use of my time, 100%. And I couldn't have learned the things I learned and had the failures I had that make me a better investor now or what have you, like, without.

Getting an mba too. Right.

But that's why. I mean, honestly, one of the reasons that I'm not interested in running a startup anymore, because I'm not sure I know how to do it any other way than. Look, we can all say all the right things, but I just look at the portfolio and the companies that I see, I don't see a lot of companies being successful where there isn't an intense culture of work. So in between gotomet and March X, I had this sort of crisis of my wife was in business school and I just felt like this kind of a loser. After the Mariners situation, I was like, God, what am I doing with myself? And I went to work for my buddy's restaurant for a while in service and just didn't really know what I was up to. So I knew I had to do something, but I didn't want to go work for someone else, so. So I was like, oh, maybe law school. I've been told that I should be a lawyer in my past, probably because I was super argumentative or whatever. So I literally just took the LSAT and I did well enough to get a scholarship to su. So I went to Seattle University Law School for nine months and may or may not have been longer. But the fortunate thing that happened in about month eight was that John and Russ and Pete Cristofilio hit me up and said, hey, we're starting this thing. Do you want to come help us? And so I said yes. I think I left my books in the locker at Seattle University and ran to the office. And so that was the beginning of March X.

Also marketing. You were also like, the marketing guy.

I started as the marketing guy out of the gate, but knew that I wanted to sort of have a more. You know, I think I knew that I wanted to develop my sort of general management skills.

Operating. Yeah.

And run a P and L. And so ended up hiring myself an amazing replacement who is 10 times better than me, Lee McMillan, who's now the CEO of Whitepages.com to take my marketing job there. After we were public and I moved over and ran our media P and L, we raised a couple hundred million dollars and bought a big portfolio of domain names. And it was my job to take those from being these kind of ugly parked web pages to building and working with the team to make them into this network of useful content and technology experience. So that was.

And what ended up happening with MarchX? I mean, I know that it's still around, but what's been the evolution of that company? It seems like it's gone through all sorts of change and growth.

Yeah. So I think out of the gate the thesis was really, it was a big bet on search engine marketing and the rise of Google. And so monetizing a network of pages via paid listings, acquiring traffic via paid listings, and actually operating our own paid search engines and feeds, that was kind of MarchX 1.0, which got us a billion dollar public market valuation and created a lot of opportunity for us. And over time, as Google and the search world sort of shrunk, Google grew and the search world outside of Google shrunk, the margins and opportunities in that category shrunk. And so the team had enough forethought to bridge into a new category. And that was voice. And so they both, by acquisition and product development have built this really interesting voice analytics platform where they have millions and millions and millions of calls from all of these major clients that do a ton of phone either sales or customer service and they pull out insights from those calls. Actually, it's one of my best friends, Ryan Pauly, who I met our first go around at Marchex, just came back and is now their chief product officer. So I'm still long March X, but they've definitely evolved.

I'm sure that going through that you learned a ton. Was that. Would you call that kind of your biggest learning in your career or kind of all of it collectively?

No, because I think when I left March X, we were still growing and hadn't sort of made the shift to a different model. So, so I left in 2008. We grew the media business there from 4 million to 40 million revenue. And so I think what I learned there was that 10 years of working for Russ Horowitz was enough. And I mean that in the manner that I didn't have the stamina he had. You know, he is still there at Marchex and was just this incredibly intense leader and I was in an incredibly exposed role running our biggest P and.

L. You got to have the stamina for that, for sure you do.

And I wasn't treating myself well. So like I was not a healthy person at that time in my life and I wasn't. So I didn't, I didn't put myself in a position to be able to make a longer run at it. But you know, and also I think working for the team for, you know, for 10 years and change, I was ready to try something new.

Yeah, of course. And so, you know, you've been very self deprecating in a sweet way where you've been like, oh, there's other people who are better and smarter and more stamina. But when are you kind of. If we were observing you not as an investor but as an operator kind of in your genius zone, like rocking your job.

I really never felt like I was doing that. So it's hard.

So do you feel like it's hard work? Like your dad said, the hard work thing and you never really felt like that flow feeling?

Yeah, yeah. I mean, look, I think, you know, if I ever felt it in any of the roles I was in, it was, you know, it was doing partnerships or closing big sales or like selling the company, closing an M and a transaction.

The relationship aspect of that probably.

Yeah, like, and the inflection points of like visible victories. Right. As opposed to just chopping wood and building product. And like so many things you need to do and you need to love to make a company successful, I just wasn't interested in. Yeah, because they didn't. I mean it's the same goes back to school. Like, I was never intellectually curious enough to like do the work just because.

Well, looking back, don't you wish you had been more like that? You're like we were sitting on a wealth of knowledge and as you get older and you're like, I'm tired and I'm distracted and I've got like this, I mean I'm full add like squirrel, squirrel. And I'm like, gosh, I wish that I had done a deeper dive. Actually my best learning period period of my life was at Lakeside. I ended up leaving there and going to Mercer island for high school. After middle. I spent all of middle school at Lakeside and I still remember my teachers and my lessons there. There's something about that. That form of teaching worked for my brain. It was much more hands on. And that's why I'm saying like this work experience that you've had has been kind of your MBA versus sitting and studying case studies. You're probably better at just like being in it and learning on the job.

Yeah. Yeah, I am. I'm just better at, you know, reading and reacting, I would say.

Yeah.

Like, that's how I always put it.

It's like, read and react how your. How your direct reports that you've had over the years would describe you. Like, are you good at managing people, or do you lose interest in that?

Yeah, I don't know.

Probably good because you're good at developing entrepreneurs or, like, taking interest.

I mean, I think I'm better at. I think I'm better at the investor founder relationship than I was at the employee or employee relationship. I feel like, look, I'm really pleased that there are folks who I got to work with early in their careers who have since gone on to do really, really awesome stuff. Like, and I may or may not have had anything to do with their trajectory. Right. But it's fun to watch.

Have you taken on that formal mentor role or have you ever been a mentee where it was like, kind of a formal, like, hey, will you mentor me?

I've been never formal. I mean, John Keister was my mentor, is one of my best friends, and, like I said, was kind of the first guy to believe in me just giving me a copywriting job over the summer, let alone, like, my first job in technology. And he. I'll never forget, he always took the time. It would have been so much easier for him to hire someone better or more experienced, but he took the time to sit with me and redline my deck or my PR release that I wrote or whatever it was, and, like, tell me what was wrong, Tell me how to improve it. He invited me to pitches to sit in and help, like, that I had no right to be in. Like, he just. And I. I think it's almost. That almost ruined me as a. As. As a manager, because I always felt like that was the bar I was trying to reach for my. For my employees. And what also happens is not everybody's up for that. Right. So you. So you can sort of the challenge. The challenge becomes too, like, identifying who is going to benefit from or even desire that level of mentorship and engagement.

Yeah. Yeah. As you're talking, I'm actually thinking about this Covid moment of remote work and thinking, like, I wonder how much of that might be lost right now. Just that quick, nimble, hey, run in my office. Quick question, quick pan out, run back, turn it around. Like, the innovation and the speed I would imagine are suffering pretty significantly right now.

Yeah. The founders that I know that are super early are, like, cannot wait to get Back in the office. Because there is just that there's current. I'm sure there are. I mean, I know there are startups, I've seen them that are trying to solve for that sort of serendipity and you know that alchemy that happens when you've got people working hard on a new problem in close proximity to each other. But yeah, and you think about it just even at big companies, like, you know, the people who are so, so pleased with their ability to work remote and, you know, I'm one of them, are typically people who are well along in their careers and don't need mentorship and don't need to build network and don't need to like learn totally.

As a recruiter, it's impacting hiring because clients are thinking about a different level of bar. Not just talent, but independence, self motivation, grit, ability to kind of have resources and figure shit out. And then as a recruiter, also with this remote opportunity, you know, we can place people anywhere from all over the country and other cities are reaching out to us to help them find the killer Seattle talent that we have.

So.

So it's just opened up this whole new way of thinking and world and I'm super curious to see what's going to come out of it. I am a little bit concerned about women and how rapidly they're pulling out of the workforce right now because of this whole kind of kids at home and how do I do it and I can't manage. And I love that you have invested in so many women. I really love that.

Well, I mean, it's sort of a coincidence, I guess, like it's happenstance, right. I looked up and lo and behold, I've got a lot of female founders in the portfolio. I will say it's not by design, but as it turns out, like my job.

Well, you need to be open to it. I mean, it might not be by design. And I know that when we first talked, you were like, hey, I'm investing in the best talent. They happen to be women, which I appreciate very much, versus just like, oh, I better check that box. But you have to be open to it. You have to see women in a certain way and make them feel safe enough to be vulnerable, to have you either on their board or as an investor. Because it's a big decision to take money from someone.

Yeah, yeah. I mean, I guess I've been fortunate enough to always work with really impressive women my whole career. My first boss before John was actually a woman who ran emerging markets at Ruderfin. Public relations, who was a tough boss. But I've kind of looked. My mom was a nurse, and after my parents got divorced, she went back to school, got her degree in two years and then got a master's in two years and then started her own practices as a counselor.

Oh, wow.

My sister has always been someone who I've looked up to, even though she's younger because of how, like, together she is. And, you know, my wife. My wife got an MBA while I was sitting around, like, you know, drinking beer at baseball games. So I've been surrounded by, you know, impressive women my whole life, and I think I gravitated towards having women's friends always, like. And I think that's, you know, that's something. There's something to that. Just in diverse investing in general, like, you kind of invest. I would say you kind of invest the way that the back of your brain works. Yeah, it's like, who are. Who are you around? Who are your friends? Who do you look up to? Who influences you? Like, if you will. If you're influenced by, you know, people from all over the place, from all different backgrounds, and like, you. You recognize and respect that they're influencing you. You're not just entertained by them. Like, then, Then. Then it's easier to. Those channels are already, like, those grooves are driven in your brain. Those channels are already open.

Yeah.

So you don't. So there's no stutter step. There's no, like, wait a minute. When you are. When you see a founder who is not a straight white male, because you. You've spent a lot of your life, you know, friends with people who are not straight white males.

Yeah.

Learning from people who are not straight white males. Not saying that we're not big fans of the straight white male in a sense.

When did you first become interested in investing and what have you learned about it?

I wrote my first check in 1999 to my buddy Matt Greenfield. What's up, Matt? He's in la. Was in LA at the time, and he roped me into the startup that they were gonna put cameras in bars and then have a website connected so you could check the scene out before you went. This is what I was really interested in at that time. Right. Like, what a great idea. I'll be able to go. And is it worth me going to the whiskey tonight or no? Because suffice to say, you know, that was $10,000 I'll never get back. But, you know, I kind of invested angel invested in technology since day one. Just very opportunistically without a lot of thought. Right. And stumbled into one or two winners and then ended up running a couple of venture backed companies. And so having that other, like that other side of the table experience.

Did you enjoy the fundraising process when you're on the other side?

No, didn't like it. I hated it.

And how has that shaped you as an investor now being on the other.

Side of the table? I think about it a lot. I was super insecure. I didn't like the power imbalance. I really got in my own head in the process. All the way from building the deck to building the narrative to. I just felt so powerless and confused and I felt like it had nothing to do with my actual aptitude to build a great business. And so as an investor I kind of. What I don't want to do is evaluate the entrepreneur's ability to deal with the anxiety that may be caused by the power imbalance between an investor and an entrepreneur. Like to me that's just a bullshit screamed and put up.

It's so interesting you say that because as you were talking I was just thinking about some of these engineers that we have that fail the whiteboarding part of the interview and then, and then they go get a job at like a competitor that's just a kick ass job. But they just interviewed a little bit differently. Maybe like an on site active interview where they're working on a problem together and some people just don't test well or some people just aren't great at pitching but they may be killer and they may have that grit and a great idea.

Yeah, I had an investor tell me, I'll leave out all the details but I would just say that this person told me maybe next time you should be a coo. And I'll say they were probably right. But it doesn't feel good to hear that when you're the CEO company. And so look, I kind of come at it from that angle, having experience have experienced that. And I want to put founders in a place where they can be the best at what they're the best at. And that's what I'm investing in. I'm not investing in how good they are at the thing they're the worst at. But, but people do that like that to me is silly. I'm going to invest in what you're the best at. I'm going to help you discover the places where you can add folks to supplement you.

I love that thinking. And that's another amazing sound bite. I think people and other investors should hear that it's like, let's invest in people based on what they're best at and we can fill in the gaps with talent in those areas that need development. It totally makes sense. So when you're investing in some of these entrepreneurs, how much of it is kind of data analysis, gut idea, founding team, what are you using as your vetting process?

Yeah, so I mean, it varies because look, there are three things that matter at the earliest stages. Team technology and traction. And I always say the more that you have of one, the less you need of the others. So the example I would give is if you're Jack Dorsey, you don't need any technology or traction, you're going to get a check for who you are. Right. Most of us aren't Jack Dorsey. And so we need either a product that is framed out, somewhat built, or a prototype or an MVP, you know, or, you know, if you've got 50 customers signed up to pay you 10 grand, maybe you don't need the product at all. So I would say the word I would use for traction appreciate is signal.

Okay.

So yeah, I don't say you don't need revenue, but if you're pinching me on your, you know, your beauty startup, right. You better have like 15,000 people on your insta. Yeah, like if you're pitching me on your recycling startup, you better have 10,000 people in a community group who are passionate about, you know, household recycling. Like, like that's the bar anymore is, is there needs to be a signal that you've done your homework and that you have a unique and unusual insight into where the market's going.

When you're looking at co founders, how important is it to you that they have synergy as far as just making sure that they're aligned on the vision and the work style, personalities, just all of it. Like, I've heard stories often of that kind of going south.

Yeah, I mean, I get less heartburn about that than some people do. I guess I feel like, yeah, you're going to have like there are so many things that can go wrong with a startup. Co founder issues. There tend to be other things that are wrong with the founding team or their pitch or the way they present that will say that before I get the chance to worry about whether they have co founder issues. I'm just passing on the investment because of those other things. Like if that makes sense. Yeah, like, in other words, like awesome teams are awesome teams.

Right.

Like, and I only want to invest in awesome teams. And so like, you know, usually it's folks who have worked together before have.

A track record together or who's known each other. Do you always take a board seat?

No.

Well, I mean, obviously you've done so many investments, you can't be on all those boards. But how do you determine which boards to join and what makes someone a good board member?

So typically as an investor, you know you're taking a board seat when you lead a seed or a round. I don't lead seeds, I lead pre seeds A lot of the time it's not appropriate for the company to have a board at that stage. So typically I'm, you know, I act as a sort of off the record board. Right. For the founder. We have recurring meetings and I try to help them get to the next milestones and then once they're ready, sort of click into a mode where they've got more of a programmatic reporting cadence and they start to grow up and act like a company a little bit from a governance perspective. But the boards I join are generally places where, you know, the founder has asked me to join and, and where there's a specific area where I feel like I can be helpful in the company's like, growth.

Yeah.

And so what is what makes a good board member? I think that it really depends on the board member. So I think there are so many different roles that board members have to play. And like on a good board you have different characters. So you have the coach or the friendly. Usually that's an outside board member. You have the fiduciary, the edge checking number cruncher who's probably usually a later stage investor. You've got the rainmaker network board member. You know, hopefully you've got someone with like a, with like a founding product background. Like, I mean, I guess there is no like one type of good number.

Right. I like how you're saying that because I'm thinking of all these different boards that I know about. I'm like, that's exactly. That sounds like the killer board, the one you just described. If you could like get all of those boxes checked.

Yeah.

And what about you as far as you talked a little bit about a backable entrepreneur and team, but is there a trait that you're like, if they don't have this, I'm absolutely out.

I guess the one trait I don't like because it reminds me of how I was as a founder is cynicism. And so I got told when I was raising money in the Valley, like, hey, you think like an investor. And I realized that was absolutely not what the investor wanted to have to say to me as a founder, right, like that's not a compliment because what it means is that you're removed from, there's a level of remove from the problem and from your opportunity. And that's, you know, you're sort of cynically looking at like, here's this market, we can exploit it, we can build this product, it's going to be worth this much money. Like this is why. And so sometimes I'll run into a founder who's like super impressive and has all the right sort of boxes checked, but I can tell that they're sort of like too much like me better, but still that level of cynicism and that just means you're not going to run through the wall, you're going to sell too early or you're going to, you won't make the pivot. So that's one thing I think you try to be careful of is I don't want to say Taurus, but folks who, folks who are well within their rights to think this way, by the way, just who have a level of remove and. They can be cold hearted about analyzing their opportunity costs and what they're doing and why, for how long. You want people who are too busy trying to fix this problem that's bothering the shit out of them to think about like the calculus of their next 10 years of their lives.

Yeah, that totally. That makes sense. And so for Ascend, what exactly do you guys focus on? Which types of business models are you looking at? Like who should be coming to you to pitch their ideas?

Yeah, yeah. So super straightforward. I only invest in stuff that I feel like I have some edge and ability to help the founder in. And also that I think our region is advantaged in. And so that's obviously E commerce, transactional consumer businesses, but specifically selling goods, Marketplace businesses, both B2B and B2C and then sort of B2B SaaS with an AI sort of filter on it. That's a little hand waving. And look, I think when you're a regional fund, you need to have a decent amount of generalism in your thesis just to be able to capture enough potential outlier outcomes. I think if I were to just sit here and say I'm only doing B2B marketplaces in Seattle, I probably couldn't deploy enough capital. Right?

Yeah, that makes sense to me.

So B2B software is kind of a catch all, but I'll say in that it's really interesting if I look at what we've invested in the Last two years. It's heavy on AI and it's heavy on this sort of concept of the proliferation of vertical SaaS within the enterprise. And how do you tie, how you pull threads across the enterprise so that people have more real time information about what's going on or how do you make sure that workers can sort of access information from across all of these apps and in a simple and intuitive way, you know, there's future of work stuff that's coming down the pike now. We're just looking at doing something in the meetings space which is, you know, everyone's favorite thing in the world is looking at their calendar for the week and figuring out which meetings that they wish they weren't at, which ones they need to be at, which ones could they just get a digest of for.

Sure, how to make sure it's worth your time and worth turning on your video camera. And how do you stay engaged where you got the kids running in the background and yeah, that's a challenge for sure. And so outside of Ascend, how are you spending your time and where do you put your energy as far as things you're passionate about?

So I run every day. So I'm passionate about my own health. Like, so sleep, exercise and nutrition is always the tough one. Right. But I try. Yeah, yeah, it's tough. Especially now where like so many of the other things that I, you know, would reward myself with, like going to watch my son play in a competitive soccer game, like just are gone. You end up tricking yourself into thinking you deserve celebration. Celebration. Right. But so, so we try to keep it tight on that front. Like so I'm passionate about that because I've realized that's the sort of foundation of my ability to be a good parent, a good husband and a good friend and a good investor. So I really make that non negotiable.

You're running on a treadmill or outside or on a trail.

Outside. Treadmill, depending on the weather. Yeah, yeah, I tried to get, you know, 45, 50 miles a week.

Holy crap. That's a, that's a runner. Runner. Good for you.

Yeah, well, it's like I said, I've kind of. I've got this problem where I'm 0 or 1. Like I'm all or nothing.

Yeah, I get those types. What sign are you?

Leo.

Oh, okay. Happy belated or I guess August.

Yeah, August. Yeah. Yeah. So I didn't, you know, and I'm passionate about, I'm passionate about Special Olympics. So super active on the board. We just had the opportunity to bring on a great new CEO. So spent a lot of time on the CEO search for that. As we can imagine, that's always a super important hire to make.

How frequent are the Special Olympics?

Well, it's funny. So we have 18,000 athletes in the state of Washington with intellectual disabilities who participate, and they train every week for the sports they're in. We offer 29 sports in four different seasons. Each of the seasons has eight regional games that lead up to one state games. So you've got. But you've got, like, league play beyond just like the actual, quote, unquote, Olympic event. There's some people don't understand about Special Olympics. It's pretty much a core. It's a pillar of the lives of most of our athletes. So people with intellectual disabilities tend to suffer from social isolation. They tend to be unemployed at a much higher rate than the general population. And so for our athletes, going to practice once a week and playing a game on the weekend isn't just, like something that they've added onto their busy schedule. In a lot of cases, it's the thing that ties them to their community and their friends. And so Special Olympics as a movement is really about enabling those folks to be active, to be connected, and to be healthy. And certainly having a daughter in the program is great, but really, it's the adults in the program who really benefit, I think the most and who need it the most. And so that's been a crazy.

So when will it be because of.

COVID So we do. We, you know, spring, summer, winter, fall games. So those are. Those have all been taking place online. It's really. It's really hard because we have, you know, our athletes tend to not have access to technology at the same rate as the general population. So a lot of struggles there. So that's been taken. It always takes a lot of my time and energy, but it's rewarding. Mark. And then. And then, you know, I mentioned Seattle Prep earlier, and I joined the board there. I'm just so impressed with what they've done during COVID for the students and, you know, feel like, because it was such a pivotal experience in my life, that it's the right thing to do to try to help pay it forward for the next generations of students there. So I get to work with those folks, too.

You've got a lot going on. I mean, seriously, just the running alone has me exhausted. You're like, maybe you are like the Energizer Bunny. Like, rest more than you thought. You definitely have a lot of energy. So my ultimate question for you is what fuels you?

You know, that's a great question. I think I want to be honest. I think I want to make my wife proud of me. You know, I think I want my kids to be proud of me.

Well, I mean, just on what I learned in the podcast, I'm sure that they are.

Well, I think if I can do that, then I'm probably doing the right stuff.

Yeah, that's great. I like that. Love it. I need to change up my answer. My husband's like, really? That would be the last thing. I'd be kidding. That's a great answer. Well, thank you for being on the podcast. So fun.

Oh, this was a blast. Thank you for having me.

Thank you for listening to the WET feature. Be sure to subscribe, rate and review on itunes, Google podcasts, or Spotify and follow us on social media to keep up with the latest news and episodes. You can also contact us@podcastueltalent.com to provide feedback, ask questions, and share topics or guests you would like us to cover in the future. We hope you feel inspired by our guests and that we have helped fuel your day. Join us next time for another episode of what fuels you.