Kirby Winfield (Ascend VC) on shifting mindset, investing in founders, and finding love in the game

The more that I put myself out there as who I am, like, the less surprised someone is when they talk to me and maybe the more they already felt like they knew me. And so they're more at ease, so they're more willing to talk about things in their business transparently. And so again, it all goes to of course I'm in the business of making money and it all goes to my ability and advantage there. But it just so happens that the way I get there is by doing stuff that I love doing.

Hey, it's Adam Schoenfeld. Welcome back to the Built in Seattle podcast where Seattle's top entrepreneurs, investors and leaders share their stories and their lessons from behind the scenes. If you like this show, then you'll love my short weekly email. The Pike Street Journal subscribesj Email each week I send some bonus nuggets from these interviews, stuff I get when the recorder's off, and some more insider takes on Seattle people and companies that's pulling PSJ Email My guest today is Kirby Winfield. He's the founding managing partner at Ascend VC where he invests in pre seed startups. He was an operator for 20 years before becoming a VC. Three times on the founding team and three exits. But he talked about the unhealthy physical and mental state that he landed in after his last exit, how he was able to change his mindset, and how those lessons and experiences have shaped the way he works with founders and and his approach as a vc. I hope you enjoy this candid and wide ranging conversation with Kirby. I'm here with the one, the only Kirby Winfield. Welcome to the podcast, Adam.

It's awesome being here, man. I'm really honored that you decided to include me.

I knew you way back before you were an investor, when you were an operator.

Yeah, that's right. And probably a lot less healthy. Probably out of town a lot more probably. I didn't know my family quite as well. It's been a long time.

Can you talk about that a little bit? What's changed in your life? You're a lot more healthy. You're not traveling as much. We have Covid now. But was that a shift from being a founder to an investor? What was that?

Yeah, so it was a huge shift. So I basically say like I spent the first 20 years of my career chasing esteem needs. So I tripped and fell into startups right out of college and the first one was called Go to Net. And we ended up taking it public and it was very successful. And so the bar was always to me like how do I chase the next big deal and how do I take more responsibility and optically appear to be successful in the startup world? And I kind of got caught in this trap where I felt like I needed for my own validation and even within my family, like I thought to be loved, I needed to be visibly successful in startups. That's a kind of messed up way to go about things because basically that makes it a life or death struggle for your ego. And I spent, I was completely binary. Like I put 100% of myself into the startup and nothing into my family and nothing into really anything else, including my health, physical and mental. So you wake up and do that for 20 years. And I was 60 pounds overweight, pre diabetic, was drinking way too much, I hadn't exercised since I played football in college and it was just a mess. And I had missed a lot of my kids childhood and I have a daughter with down syndrome and had left a lot of that on my wife to help her in her early development. So I got out of the last startup we sold in 2016 and just looked in the mirror and said okay, this isn't working. I'm not happy, nobody's happy. And by the way, every startup I did, the outcome got worse. Now they were all still exits. I guess it's good. But it was going the wrong direction. So my, even if I were just chasing the, the external like validation that wasn't even happening. And so I just said you gotta reset. And I wiped the. Like I said I'm not doing anything. After we sold to homeaway Expedia, I said we're not, I'm not doing anything business wise for three months. I'm not taking a single caller meeting and I'm gonna run every day and I'm going to get my genetic health analyzed by the now defunct startup Arivol. And in order to make some changes and came out of that into 2016 and said all right, what, what do I love doing? Which is the first time I've asked myself that maybe ever, certainly since high school. And so I went out to explore the answer to that question and that's what led me to, to launching a fund three years later.

What an amazing journey. I didn't know that backstory. I'm glad we started on a lighter note right there. Kirby.

Hey, it's got. It is lighter now I'm 50 pounds lighter.

That's incredible. What do you think it was that allowed you or helped you make that mindset shift?

I think I realized that it Wasn't sustainable for me to keep doing things the way I had been doing them. So ripping off these four year, five year sprints that were all or nothing, I think part of realizing that. So it wasn't possible if I wanted to keep a family and have some semblance of sanity. And then also I think in parallel to that, I finally stepped back and had a couple of people tell me, hey, you tell the story, this narrative about yourself, like you're this failure. Because that's how I saw it. The first two startups, like I was founding team but wasn't the CEO and so they did really well. And I thought, okay, I did had something to do with that, but rode the coattails a little bit. And then the next two startups were decent outcomes but not home runs. And to me that just felt. Because the first two were monsters. I just felt like I was. I always tell people, like, the more I got in charge of something, the less good it ended up. And I really internalized this narrative of now I suck. And I had a couple people just slap me and be like, you're very fortunate. You've had a lot to do with the positive things that have happened in your career and the outcomes that you've been a part of, even the ones you didn't run and like, just shut up and be happy with. What externally looks pretty good. Like four out of four startup liquidity events. And like I felt like they gave me like people, I gave me freedom to feel like I'd done enough in one if in that world, not that I've done anything great, because I still don't think I did, but like enough that I felt checked the box for my sort of ego and I could move on and really then ask that fundamental question of what I wanted to do versus I felt like I'd done what I had to do in startups, if that makes sense.

Yeah, I can imagine. That was powerful. Moving from that mindset for so long of what you had to do to thinking about what do you want to do, what do you love doing? And I gotta say, knowing you and looking at how you have put Ascend out in the world, you definitely look and feel different than a lot of other VCs. Has this experience, kind of the roller coaster played into the type of ethos you wanted to have as an investor or how has that played?

Yeah, I think it has. Just in terms of the reasons that I'm doing it. I again, I had a pretty good run there and fortunate enough that I could have chosen to do a bunch of different things. And so literally the reason I'm doing VC is because I love founders. I love, I love the game and I, I think there's an opportunity to be additive and fill a gap here in doing it the way I do it. And it feels more, let's make the analogy like I never, I had a hard time finding product market fit with the startups that I ran. But, but with, with investing, I feel like I have that finally have that product market fit where there's a pull from the market. I feel like what I'm doing is something that some segment of the market, at least from a founder and an LP perspective finds unique and interesting and 10 times better and wants it and, and I'm sure I'm not for everybody but, but being able to be my like authentic whole self and fundamentally be invested in the success of founders, which is easy to say and hard to do as you start writing bigger checks and going up the capital stack, but at least right now I get to get in the boat and row a little bit and that's fun.

Can you talk about what that means, doing it the way that you do it and how that is different out in the market? Thinking about this in terms of product market fit, how is that sort of unique relative to others that are doing early stage investing or investing in general?

Yeah, I think that in working with Look, I've raised money from a lot of the institutional investors in Seattle or am currently working with them on companies in our portfolio and have very good friends at pretty much every firm you can name in Seattle. Not that's any great feat because there aren't that many and I would say the vast majority of them are much better investors than I am when it comes to, you know, Series A and beyond. And when it comes to really understanding what does C to A and A to B look like and how do I help a company focus on the right things to get to those next milestones? And I've got plenty of holes in my game, but the one place that I feel like I'm advantaged is I spent the last decade raising venture and managing venture boards and venture expectations and honestly not doing a great job of it, but then having to drag one of those cap tables through a peri recapitalization when figuring out how to do a pivot and find an exit and then again raising money from investors for another deal and sort of getting halfway to where we wanted to be and not being able to necessarily feel great about our chances at a series A and trying to find. Find a good outcome for. I feel like I have fresh and relevant experience. It's almost like I look at, I look at some investors in town who have operated and they were all so successful that maybe they didn't get the same sort of painful experiences that I had that maybe are more relevant to a bigger group of founders. I don't know.

Yeah. Almost like your founder empathy spans a wider range of possible situations across all the four companies that you did and the ups and the downs. Because we all know that it's not going to be a straight line in most cases.

No, that's right. And again, I don't know. I think a lot of this, I wonder how much. How sustainable it is 10 years from now. Am I going to have the same sort of visceral connection to my own founder experience that, you know, aligns me with founders. I hope I can maintain it. I think investing at the earliest stage helps because I'm. A lot of times I am a proxy sort of team member for however many hours a month. So I hope I can maintain that. But yeah, I think that's. I think if you ask people, that's probably unique. Just, I just try, you know, empath. I never trust anyone who says I'm empathetic and authentic. So I would never say that. But that's the feedback I get is that people feel like they look. The other thing is I'm not going to lead your seed round ever. I'm not going to lead your A round ever. So there's no downside in telling me everything that's going on and asking me for help. And that's another place where I feel, I feel that it's a little bit of a different relationship than it might be with a firm that has later.

Stage ambitions because you, you remove the need to posture for the next check. In a way, yes. And you can just get down to what really matters of how are we going to grow this business, how are we going to validate our market? Like, how are we going to have success here at this phase of the business?

That's right. I literally, all I care about is you winning. And by the way, that sometimes ends up in me getting the opportunity to invest more money anyway to win.

You said you love founders. Can you talk more about that? And why'd you choose those words instead of I like investing in founders or I like betting on founders? We hear VCs say different flavors of that, but you just said straight up, I love founders. Can you tell me more about that and where that comes from.

I said I love founders because I think I just like people. I've always had a big tent approach to life I'd rather have. I feel like I learned from every relationship I can build. Every, like, half hour I can spend with someone makes me better. And I have this insane, like, benefit of the doubt that I give people, person to person. If you talk to people I've known for a long time, they might tell you that over time, that has a half life. But, like, I'm very optimistic. And, And I also, I get, like, I get when you're at that stage of a company where you're. You've decided to do it, but it's not really anywhere yet. And, like, how hard it is to communicate the reason that you're doing it and how frustrating it is to communicate with investors who don't seem to want to hear the truth, but they want to hear information, like, arranged in a certain fashion for their consumption that will allow them to evaluate you. And I just, I remember being. I remember really struggling with power imbalances. Okay. As a founder, really struggling. I'm a very insecure person and I need to be loved. And I've got all this, like. And so I hated the power imbalance. Getting in a room with a VC, getting. And the VCs that many VCs that I pitched were very much traditional VCs, where part of the game is that it's an intimidating thing. They're intimidating people whether they mean to be or not, and their offices are set up in an intimidating way. And the meeting logistics are intimidating. And I always felt like I had to fight through that just to be able to let them know me and let them know why I was doing what I was doing. And I thought, what a stupid barrier, like. And if I'm struggling with that, as a relatively privileged founder with a track record and a network, imagine someone who doesn't have those advantages going into those situations. And it's just a shame because basically what you're solving for in that case is, as a vc, is okay, who can overcome. I guess I'm not going to invest in anyone who really struggles with power imbalances and anxiety, but, boy, you might miss on some winners there if you do that. And so I figured, how can I remove that when I meet with founders? How can I make sure that I see the founder's whole self and put them in a situation where they're able to communicate with confidence why they're doing what they're doing? And how they're going to get there. And to me that was about being of service to the founder and going to the founder back when we could go places. I don't have an office a lot of the time I would try to find a place where I can meet the founder that wasn't my office. And just trying to set things up so that to give myself as an investor look, it's selfish too, right? It's an enlightened self interest like to give myself as an investor the best chance to know someone but not let it get screwed up by the sort of noise of the power dynamic.

That's such an interesting observation because having felt that raising money and going to all these big scary boardrooms, it's definitely there and I love how you've stripped that away in your process. Does that then show up in how you work with the companies as well or how does that show up? Because it sounds like you've made some pretty intentional choices about the early stages of getting to know founders and before you make the decision to invest. Does that carry through to then how you work with them once you're in the deal?

I don't know if it carries over per se. Like I would say once we're off and running. Look like once we're off and running my job is to help you support you, but also hold you accountable. Because we're now on the clock. We're trying to optimize learnings per dollar spent. We're trying to figure out where is the pole in the market for the thing that you think you're going to do. And then we got to find that and then once we feel it, we got to, we got to make sure we lean into it in a way that gets us to the next fundraising milestones. Because typically the companies I'm investing in aren't raising that much money. And and so it doesn't really help anyone for me to spend the entire time canoodling with them and empathizing, although I do my fair share. But I think if you ask folks like I typically get on at post close, a bi weekly call schedule with founders and without being a proscriptive board OKR type manager of the situation, I want to make sure that folks can bring me places where they might be blocked and see if I can help. And at the same time if I see someone going off the rails or making a mistake that I've seen made or made myself before, I can help short circuit that. But yeah, I'd say the tenor of the relationship shifts post Deal, but I don't think it's a Jekyll and Hyde thing.

So changing gears a little bit here. You seem to have leaned into content and brand more than many other Seattle VCs. How are you thinking about go to market for yourself as an investor?

I think the first thing is that I was an English major. I was a creative writing minor. I always get a hard time for my college friends because many of them went on to write best selling novels and, and I write emails for a living, but I've always liked writing. And then I was actually a copywriter early on in my career at goto. Net and wrote PR and marketing materials and then so I have a marketing background and a writing background and I spend, and I spend an ordinance amount of time on Twitter talking about hip hop and record collecting and shoes and like second only to the amount of time I spend talking about startups and venture capital. So it's, I've been doing that for a decade. So I think just, I have a, I've always loved to write. I have a marketing background and I'm really curious about different communities in, in the social media world. And then from a boots on the ground perspective like I have, I was an angel for 20 years here and made more than 30 angel investments and got to know a lot of other angels and then as a founder, you know, raised money from a lot of VCs and then as an operator worked with thousands of different people in the tech ecosystem over two decades. And so from a sort of network perspective I felt I have a lot of folks I can talk to and I think I have some interesting things to say. And I'm also okay looking stupid in public. That's been one of the best things about this whole like shift and awakening to not caring about what people think like as much and what people think of my brand or my success is like, or lack thereof is like I'm just okay, I'm just okay shooting from the hip and learning on the fly. And I like, I like the challenge of trying to like make a joke on in 280 characters. And I like tweaking convention. I like the idea that I'm a VC even though I'm really not. It's a 15 million dollar fund. It's, it's small potatoes. It's VC enough that I can tweak the convention a little bit and make little jokes on my website and just, and, and nobody's gonna tell me no because it's my shop. So if I want to put up a Wacky startup toolkit that's like half finished. And I edit it once in a while at one in the morning when I'm. You can't sleep and there's a list of people on it and it might not be complete. And I forgot, like, two of my, like, people I respect the most, and they asked me, like, what I'd done or what they've done to deserve being left off. I don't care. It doesn't matter. Like, the, like, I think a big thing is I just feel so free to. To really just be myself. And that seems to map well to what some founders and I probably won't, you know, never going to please everyone all the time. But what some founders find is interesting, compelling and positive. As a founder, so you just want positive energy, right? Like, whether or not the investment gets made. Is it. Is it is. You know, do you feel valued in that interaction? And do you feel like. And do you feel like you connect with this person? And the more that I put myself out there as who I am, like, the less surprised someone is when they talk to me, and maybe the more they already felt like they knew me. And so they're more at ease, so they're more willing to talk about things and in their business transparently. And so again, it all goes to. Of course I'm in. I'm in the business of making money, and it all goes to my ability and advantage there. But it just so happens that the way I get there is by doing stuff that I love doing. And I think if you love. By the way you've talked to people, right, who, who don't understand Twitter, they don't understand why you're there and what you do there. And I'm like, look, if you don't love Twitter, if you don't understand that and enjoy it, then I can't explain it to you, and you're not going to be good at it because you need to love it. And Twitter is not the only place I'm active. But, like, that's an analogy, right? If you're the kind of person who just loves this stuff and shooting from the hip and putting, Putting. Putting it all and making jokes and being. Being. Being a jackass sometimes, then it's going to work for you. And if it's not, then it doesn't. And so I guess there's maybe not that many people who enjoy the things I do.

Yeah, I love the way you describe that, because it's not dogmatic. Everybody should put content out in the world or write or share their opinions in the way I do, but that it's something you love and enjoy and that comes through. And I'm, I love that you do it because it's great to see you out there and I want to encourage people listening to read your about page on your website because I just love it. When I say we, I mean me lines like that. And I just love how direct and open you are in describing yourself and the way that you operate. It's. It's very refreshing. Refreshing.

Thanks man. That's good. I'm glad that comes through. I feel, I do feel like Even though I'm 46, like I'm really only in my first year of running a fund and so I, in some ways I'm like I'm 23 again and I think, I think that I, and I watch a lot of younger entrepreneurs and how they operate and the conventions have changed. Right. There's this rise of younger VCs and alternate vehicles, these rolling funds that people can raise on angellist or just solo GPS doing things. And, and you don't have to be, you don't have to be Kleiner Perkins. Like you don't have to, you don't have to speak in thought leadership language and publish research and, and, and anyway there are lots of different ways to.

You don't need to be in a peer reviewed journal. You can, you can put out a tweet and see what happens.

Yeah, that's right. And if you're wrong and if it looks silly then everyone forgets in a day anyway, like it's, it's okay. And I think having lived in like having grown up in basically in public companies, it's just very liberating to not have to worry about any of that stuff.

Can you talk about how you pick companies? What matters most when you're making an investment decision?

Height. I pick them by height, dammit.

I will never raise money from you. Kirby.

Depends. The other companies I'm looking at. It's the typical. I have a heuristic that I use that I'm sure everyone else does in some fashion or form at the earliest stage. And that is like team, team technology and traction. And by technology I mean product and market. So it's so it just. But it. Technology starts with a T. So and when I say team technology and traction, the more you have with one of those, the less you need of the other two. So I always make the analogy. If you're Jack Dorsey, you probably don't need a product or traction because you'll just Get a check. I think that's how he raised for square, like for right just a deck. But most of us aren't Jack Dorsey. And so we need like an mvp. And if our MVP happens to be like some whisbing world changing cure for cancer IP then we probably don't need a ton of traction or revenue. But it's probably not. So then we probably need some traction. Or if we have a million dollars in revenue then we probably. Nobody really cares about our technology and whether it's differentiated. Like we have a market but we probably don't have a million dollars in revenue. So you need to have all three of those things. I think the team is by far the most important. So I like to see someone who not only is impressive and is doing it, has a great fit for the problem and is passionate enough to do it for 10 plus years and go through all the stuff that you and I know founders need to go through to get there but that also is like self aware enough and compelling enough to fill in the gaps in their experience and expertise and to be able to bring on co founders or early employees that they have no right to be able to bring on. Because by the way that also signals their ability to have close customers they have no right to close and get PR they have no right to get and eventually onboard investors they have no right to have. And so it's all about that sort of the team dynamic and that's the price of admission. And then assuming that you have that yeah it matters. The general do you have a credible. Do you have a credible path to discovering what where that where the market pull is for your general solution Is the problem that you have, is it an urgent problem for the market that you're addressing and is your solution 10 times better than what's out there? All this typical stuff but I'm more interested in the opportunity space than market size. So I'd say I want to see a bottoms up on if your solution works for a specific like submarket. I'm less concerned about the size of that market but more concerned about how you ladder out from that down the road. So you just need to. There needs to be a credible sort of I can get this from because basically I need to know that you can get from pre seed to seed milestones.

So and so are you looking for more of a prescribed path or vision on how they take the wedge and expand or ladder out or is it more just about knowing there's option value?

I think it's knowing there's option Value. What matters to me is can you express a vision that ends up being meaningful if you can reach it, but understanding that's probably 10 years out, can you at least build the first two rungs of the ladder to get there? Trust that if you can do that, you'll probably find your way to the next eight.

Yeah, that's a great way of saying that. I struggle with that because you always have to start small. To start right, you need a sub segment or a niche or some place to go first. But yeah, if you're going to be on the venture path, then it needs to have that big option value and that big potential.

Yeah, it's. And I used to find it obnoxious as a founder because I was like, we have revenue. Like, even at Series A, like, we had $2 million in revenue. And I'll never forget, actually Michelle Goldberg, who was at Ignition at the time and who was on her board, she said, yeah, but that revenue is worthless. It's the wrong kind of revenue. And I was like, what do you mean? How is it the wrong kind of revenue? You know, it turns out it was like media revenue, not SaaS revenue. The multiple is different. And if I'd listened to her earlier, we would have probably. It would have made a difference to our Runway. And something else she said actually was, I got out of a pitch meeting and I was like, why do VCs want me to lie to them? Because I was like, I'm just selling widgets here. You know what I mean? Like, I'm growing revenue, like on SaaS, and it looks good and we'll keep doing it. And they don't want you to lie. They just want you to have vision. They want you to have a bigger plan than just making your next quarter and selling more widgets. And that's the hardest thing, I think, to tell founders, especially the ones in the portfolio. Now, as we get further along who are going for series A is, it's so different than Seed. Like, seed is okay, it's not traction, it's signal. And did you build a product and do you have a good team? Pre seed is do I think you can get those three things? Seed is, you have those three things, and then A is, oh, you're growing revenue, like, hand over fist. So what? Everyone who's pitching VCs for a has that profile. So the revenue is no longer the thing. That's the hardest thing for a founder who's gone from zero to one to understand because you're like, but I finally have revenue. It's growing like crazy. I can't service the demand. And they're like, yeah, that's a problem. How did you let that happen? Like, how are. How do we. How do we resource to service that demand? And like, moreover, like, how are you gonna get to your B? Because that's apparently the real hard thing to do. And meanwhile, founders are tearing their hair up because they're like, they realize that what they thought. It's a false summit.

I love that one. It's. Yeah, it's. You're on the second rung of the ladder and you need to stand there and look up instead of just taking one more step the next quarter or the next year. And that's having been there, that's incredibly painful. What do you coach people to do then when they're going into their a. When they're in that beautiful position of having revenue and having reached the false summit? How do you coach people to move past that?

I had a conversation this morning. I think the. The thing is to just to remind them like, that fundraising has very little to do with like today's reality and all. It has everything to do with the, you know, envisioning the future because that's where certainly later stage investors that's. They need to believe that you are the person who can hire the right people to scale up the company in the right way to manage and grow that demand, to take that ember and turn it into a hot fire. But like one that's contained, you know, maybe. And not a timely analogy to make these days with fire. But it's. So the advice is don't talk to investors about your like you're. If you're. I was again, I was so insecure that the minute I had any sort of metrics, I just wanted to point to them and put them in every slide. And every slide was a metric slide. Oh, look at our ARR Growth and look at our nps. And I'll look at. And again, that's the price of admission. So really coaching founders to at the a spend a lot of time talking to and pitching friendly. It's like 20, 30, 40 people on a narrative around why your company is going to change the world. Why is it different than all the other companies? Why? How? What's the story in the Wall Street Journal in year seven? Like, when you're going public, what is that story? What's the headline? And then work backwards to. Okay, look, things are great. Now here are the three things we know we need to do to get to 10 million ARR. And having a credible sort of. Because then now you need to be showing like the ability to both be a strategic sort of leader of a growth stage company and like an operating manager of that same company. And so you need to be able to tell a really compelling story that starts to, you start to basically you start to have to sound like a Wall Street CEO on a roadshow. You're not there yet, but like you start to shift. And it's funny as you have enough companies that move through the chain up through series C and D, it's what happens. Like the series B deck even certainly the series C deck that your 12 slide. My little like advice about 12 slides. That goes out the window right around series B. It's 30 slides and it, and it starts to look a lot like, okay, now we're looking at comps. We're looking or diving deep into the operating metrics. And that's. You have to be able to convince investors that you're. You have the capacity to be that leader. And that's very different than saying I, hey, I got this thing to its first sales.

Absolutely. Such a hard thing to do. I love the way you frame. That should be your next Twitter storm over there. On Twitter you gotta talk about those questions about the seven year later Wall Street Journal headline. I loved those. And that way of framing it.

Maybe I'll get an AI to transcribe this.

I think there is one for that now. The, the gtp.

Yeah, that's right. Do you have access? I've got one. One founder I know who, who has given me a little bit of access. It's something.

Oh, sweet.

Stuff is crazy.

We'll just get AI generated. Kirby.

Yeah. Yeah. I feel like what could go wrong?

All right, this is, this is. This has been great. I'm learning a ton. I want to be respectful of your time. So we should wrap this up with the Supersonic 6. All right, number one, how much coffee do you drink?

I drink two cans of high brew espresso in the morning maybe then a double Americano iced after that sometime mid morning. It's definitely the lowest my coffee consumption has been in since high school.

That's low. I won't ask you about when it was high, but that is. Yeah, that's an impressive low watermark. Number two, what's one Seattle company that you're following or studying right now?

Man, that's a, that's a tough question there. Because honestly, all the companies I'm following are either in my portfolio or about to be. I don't Pick my head up very often. So that said, I spend a ton of time with crowd cow. Joe and Ethan are incredible founders and friends and have really built a super interesting logistical and emote around sustainable craft protein and that's only been gigantically, positively impacted by Covid. So that's been a real fun one to be involved with and spend time on.

Number three, who's one Seattle person that you're following or learning from right now?

It's that, you know, we talked about this like before. It's tough. It's tough to pick one person. I think I actually do think Leslie Feins Egg from Female Founders alliance is probably someone who I'm really consistently just. I think I benefit from her insights and her transparency around just whether it's again, like I feel like she's a kindred spirit a little bit like she shares a lot about her just day to day struggles with things she's tackling in life and like how that impacts what she's tackling for business. And it makes me feel like I've got a. That I'm not alone because I feel sometimes I don't communicate all those things. I'm good at talking about my past, but my present I try to keep pretty bright and shiny and she reminds me that, that you can be successful and build something unique and. And by the way, she's like building something really unique and necessary and also be human and so I appreciate that.

Check out episode 18. Leslie Feinsig was on this podcast and I and she was very open, very direct, exactly how you described.

I gotta go. I gotta go download it. That's perfect.

Number four, what's one thing that Seattle needs to improve as a startup hub?

It needs to be cool force for people to invest in startups. There's not social capital tied to angel investing in the city. There is in the Bay Area. We have an awesome angel community and I think we have a lot of. Certainly the angel groups in Seattle are probably, if you put them together, are like the number four source of funds in Seattle, bigger than some funds, including mine from an annual deployment perspective. So I think people need to recognize the importance of the angel groups and individual angels in Seattle. But I did a survey earlier this year of founders and there's still real concerns around angels in Seattle not evolving as quickly to accept simpler instruments like safes, or to invest in diverse founders or to invest in anything that's not enterprise SaaS. And that's just. That's not me saying that I'm an angel too. I didn't like hearing it, but there is some, there is some. And so people ask, what do you think the challenge is? And I just think in the Bay Area you have like the first thing you do after you make if you clear 250 or 500k either in an exit or your salary, you're saving like you're finding a way to spend to put 10k, 20k into startups. Just as a young sort of startup employee, I just don't know that I see that happening here yet. It's starting to happen more. I got a call, I actually got a call from an employee of a startup that I'm invested in and she said I've saved up $50,000 and I want to invest in black founders. I was like, all right, this is a signal. Certainly great to hear someone wants to represent, invest in underrepresented folks. But the fact that it was an employee of a startup that has not exited, that tells me something. And maybe it's not that it's social capital, but its sociopolitical capital. And the more of that happens, I just think that's going to change the dynamic of what it's like to raise your first money in Seattle. And I think it's going to change it for a good way.

Yeah, look forward to seeing that evolve. We could definitely use it. Number five, what's one piece of advice you'd give your 20 year old self?

Stay fit. I think that would have solved a lot of problems in my life if I had forced myself to just, just to run six days a week. Because as it turns out, if you force yourself to do that, you'll not do other things. You don't do those other things, you may have a lot more positive things happening in your life and you'll be a little bit more able to take advantage of those years. That said, like, easy to say now.

That'S a pretty good site.

Had some pretty good times.

Yeah, absolutely. Number six, what can this community do to help you? Is there anything you want people to put their attention on? Anything you've put out recently that you want people to go check out?

I wish more people were on Twitter in Seattle in the tech ecosystem and maybe you're all there and just. And we're not connected. So follow me on Twitter. I'm just Erby Winfield and I would love to see a broader representation of folks from this ecosystem spending time and communicating and learning on Twitter because I just think it's a super valuable, valuable tool for, for investors and founders and everyone else.

If people listening Start blowing you up, mentioning you on Twitter, asking you questions. Are you going to respond?

I always respond. I'm pretty sure I've responded to every. Every tweet that's ever been that I've ever been tagged or sent, and including the one where the guy accused me of. Oh, God, it was so weird. I got randomly accused of being part of some sort of drug trafficking conspiracy. Yeah. Which even in my younger days would have been a stretch, but I replied and then I. Then I blocked, so don't do that. But otherwise, yeah.

All right. All mentions and messages are welcome, other than accusations of drug trafficking. All right. Glad we have some guardrails on that. Kirby, this has been amazing. Love talking with you. Thank you for everything you're doing for the community.

Yeah, thanks a ton for having me, Adam. And thanks for all you're doing. Podcast is amazing. You're an amazing founder. I love your journey and how you took learnings from simply measured and applied them in your next deal. And I applaud how you've been. You've been able to. I think you learned a lot more, a lot faster than I did. And hopefully people can learn from you so that more of them can have your journey, which I know is still ongoing. And I'm excited to see where you go.

Thanks, man. And thanks for spending time with me today. John. I think it's on. Hey, it's Adam again. Quick note before you go. Thanks so much for listening. I hope you're enjoying the show as much as I am enjoying making it. If you do like it, please leave a rating or review that would help other people find it in Apple podcasts or wherever you listen. And if you have any feedback, send me an email. Adamseattlepodcastmail.com no underscores, no periods, just Adam Seattle. Podcastmail.com it.