125: Seth Levine on Rebuilding Your Company for the AI Era From Scratch

I wish I'd known it was gonna be okay. I spent a lot of time sacrificing things in my personal life and with my family because I thought I needed to be everything everywhere all at once, and I didn't need to be. One of the things that I have realized as I've gotten older is that you don't need to say yes to everything. I understand there's maybe a pushback on that, which is like, well, you're successful because you did those things. But I actually think I could have done 60% of the things that I did and still been just as successful, right? Getting on an airplane and going to New York 13 times a year for the first 3 years of Foundry, and it was before New York 'Cause it's like a big startup thing and that's part of why I did it. But I, I think I could have gone 6 times a year and it'd been just as effective.

Welcome back. This is From Startup to Grownup. My name is Alisa Cohn, and today I'm thrilled to welcome Seth Levine to the podcast. Seth is a founder, investor, and author, and one of the co-founders of Foundry, the venture firm he built alongside Brad Feld and their partners. Seth has spent decades working with founders and leadership teams, and in this conversation, he brings a lot of candor about what it really takes to build something enduring. As you'll hear, Seth and I jump right into our own version of a cold open, talking about how meaningful his relationship with Brad has been. Brad, also a past guest on From Startup to Grownup. We then talked about how boards should be thinking about AI right now and why leaders need to stop asking how to make the current organization a little more efficient and start asking how they would build the company from scratch today. We also talked about the long road of building Foundry itself. Including what it felt like to keep getting rejected while trying to raise the firm's first fund, and the little-known fact that initially they had a 5th partner and why and how that didn't work out. Seth also talked about productivity, the systems he uses to stay intentional about his time, what he wishes he had known earlier in his career, and the qualities he believes matter most in successful founders. This was a great conversation, super practical and super fun. So please enjoy my great conversation with Seth Levine.

Brad and I have worked together for 25 years now, and we call each other on our BS all the time. And he's one of my absolute closest friends in the world, right? And probably outside of my family, the most important person in my entire life in terms of like the trajectory that my life has taken.

Wow, I love that. Well, I'm not even gonna cut this out. I'm excited to start the podcast this way. And let me introduce you to everybody.

Did we just do the cold open without even realizing it?

We just did the cold open, exactly. This is Seth Levine, and you're a founder an investor, and an author. And as you were just mentioning, you and Brad Feld, the famous Brad Feld, along with 2 other co-founders, co-founded Foundry, a very well-known VC firm, which made news in 2022 when you said you were not gonna be raising a new fund. But I really wanna jump right into the boardroom and right into AI because that's something we're all talking about now. It's a never-ending drumbeat. How should boards be talking about AI with founders right now?

Yeah, I love that question. And by the way, thank you for having me on. Let me jump right in. I love that.

Great to be with you.

Uh, we're very action-oriented. oriented here at Foundry.

Yeah.

So that's great. Obviously every board is talking about AI, and I think it's maybe the first question to ask, like, AI will never be worse than it is today. So as AI gets better and better, how does that help our business and what is the threat to our business? Right? And both those two things can be true, but I think that sometimes people like jump straight into, here's how we're using AI to whatever, you know, juice development, which is sort of the obvious thing. Everyone's using it in engineering, but they're not like taking a step back and saying, hey, as AI gets better and better, how does that help our business and what is the threat to So we're having that conversation. And by the way, that's a continual conversation, right? Because as we use the tools more and more, we get better ideas for actually what it can do. And by the way, as new models come out, I mean, the last set of models that came out, you know, a month ago or so as we were recording this, you know, they are way better, like maybe not quite an order of magnitude better, but like close to that than the last ones. And so it's important to revisit those questions on a continual basis and say, what is the opportunity for AI, but how does this threaten our business? And we, we have companies on both ends of that, right? We have a couple where AI is a huge threat to what they're actually doing. And others where it's a huge opportunity, and many sort of have a little bit of both, right?

Right. Can you give us an example? You don't have to name names, obviously, but give us an example of a company of yours or a company that you know about which is not pushing itself hard enough about AI. They're like, we're using it to juice development, it's fantastic, we're adding this AI, you know, plugin or something, but that you realize, wait a minute, it's literally reshaping the way people are buying, and a year from now you're gonna be outta business unless you rethink how you're doing something.

I mean, I, I will generalize to a lot of businesses because what I would describe is I think there's probably 10 to 15% of companies just generally, and I think this is true in the Foundry portfolio, so I'll be a little bit self-critical as we push our portfolio on this. And we actually have a working group inside our portfolios led by one of our portfolio CEOs that's an AI working group, because I think people want to move themselves from what I'm about to describe as the middle group to the sort of the upper tier. But I think this applies generally pretty globally. There's probably 15 to 20% of companies that are really leaning into AI. They're using it to do more than just sort of be a copilot on engineering and make, you know, make their engineering teams go faster. They're using it in ways that are a bit more fundamental. They're creating programs inside of their businesses. They're using it in whatever they expose to their customers to give them a better experience, to allow them to customize reports and data and, you know, whatever it is that they're getting from their platform. So that's probably 20%. Then in our world, probably most of the rest are sort of like dabbling in it, but mostly using it as this sort of coworking tool, right? As something that enhances productivity and makes makes everyone whatever, 30% better or whatever it is. And that's great. I mean, that can be helpful from an operating expense standpoint, et cetera. But they're not really thinking about how does it fundamentally affect our business. And then I think in the broader world, there's probably another, let's say 15 to 20% of businesses at the very bottom who kind of have blinders on and they're just like, no, no, no, no, I wanna keep doing it, you know, the way that I've been doing. And I, yeah, I use it for sort of like search, enhanced search essentially, right?

Right.

By the way, I think how a lot of consumers use AI, and look, all of this is okay, right? I mean, I, I'm sure you do as well. I get questions from friends and family about like, I'm using it wrong and everyone talks about it being so powerful, but like I'm not really doing anything with it. And I usually start by just saying like, we're not even in the— I don't love sports analogies, which is what you say right before you use one. But like we're in the first inning, but we're like, it's like the first batter, right? Like it's really early and it's okay. And I try to give people a little bit of grace around just like, however you're using it now is fine, but let's talk about how you might use some of these tools to be even more effective, right?

Yeah.

And so I think it's okay. Now, when you're building a venture-backed company, I don't think that that's okay. I think you need to be moving into that top 20% and that needs to grow. Um, and so we are pushing hard on our portfolio to be thoughtful about using it in much more fundamental ways. And by the way, we're doing the same thing at Foundry. I don't know if you wanna go do a deep dive on what Brad's building with this sort of company operating system, but like I spend my days in the terminal window now on my laptop, like kicking off processes that, you know, Cloud Code is working on, right?

Yeah, that's amazing. And I wanna hear what you guys are working on and what you, Brad, are working on. But I would say that I just had on the podcast, the CEO of Whisper, whisper.ai.

Yeah.

And also the CEO of Harness. And obviously whisper.ai was actually born in the AI age, right? So it was born like a year or 2 ago-ish. And so I would just say the way he's thinking about their business is very much with an AI mindset. So AI native, and doesn't just mean the product. It means, for example, what he said was, we are never gonna hire another customer service person. We have 5 people, they're all managing all these agents. We're gonna scale infinitely because we can scale agents infinitely. That's a completely different way to think about customer service. in any kind of company. The Harness CEO, Jyoti, talked a lot about how they're thinking about pivoting, or I wouldn't say pivoting, but, you know, 'cause they were AI first anyway, but like evolving in this AI moment. So I'm just curious to ask you, how are you pushing your founders to really be methodical and tinker their way into what they need to do and really dive into using the tools? Like, what are you actually saying to them and what is their response?

So a couple things. First, love Whisper, use it all the time. And as someone who, and I'm sure you're the same way, like, you know, as an author, right? I write, I have a blog, I've written a couple couple books, like I like typing, but Whisper is like completely changed.

Game changer.

I mean, it's funny to watch me work sometimes 'cause I'm in a terminal window, I'm talking to my machine, which is really just talking to this AI, you know, Claude Code, and then it's kicking off all these process. And if you teleported in from, you know, 10 years ago, you'd be like, what is going on here? So love that product. And I think it's absolutely fantastic and products like it. And I also, by the way, it's so much better. I'm sure you've had this experience with just like the built-in voice-to-text, particularly on the Apple products.

Yeah.

If there's a weird way to spell something, it will find it, right? You'll be like, hi Susan, you know, thanks for coming over. And it's like S-I-O-U-X-I-O-N. And you're like, it's never spelled that way. But Whisper, of course, can see if I say Alyssa and I'm responding to something of yours, it'll actually see, oh, that's A-L-I-S-A, not E-L-I-S-A or whatever, right?

So also formats it for you. I mean, it's shockingly good.

And it works, right?

That's a big Whisper commercial. Okay, good.

Yeah. And as you make adjustments, it'll say, oh, I'm saving this as as a preference anyway. So that is awesome. And I've already talked so much about it. I barely remember what you asked, but I think I can get back to the actual question. Yeah.

How you're pushing your founders right now, I would just say in a rigorous way to think about how they're evolving into being quote unquote so-called AI native.

So you framed this question perfectly because you gave this example of like company that was born during the AI age, right? And it's funny, I just had this conversation with a company with a board, and it's a company that's been around for a while and it's large. It's a $70 million top line business and at one point had, you know, 2, 300 people working for it. And we were saying there's a fundamental difference between companies that were started, let's say, in the last 3 years and companies that were started before that. And that's what you're describing. And the behavior that I think is the most important behavior to drive is if you were starting this company today, how would you actually do this function? 'Cause I think what businesses tend to do is say, how do we make our customer service, and to keep with your example, more efficient? Okay, well, we've got 10 people that work on customer service. How do we add AI on top of that and make them a little bit more efficient? As opposed to saying, hey, if we were starting this business today, how would we think about customer service? Okay, well, we'd have 2 really good people in customer service who managed 15 agents of some kind to do it. I'm making that example up, but that is probably not that far off from the truth. And so instead of saying, actually, this is how we're gonna revamp customer service, they instead say, how do we make our 10 people 30% more efficient? And I think those are 2 fundamentally different questions, right? I mean, it's sort of like the old HR question that we were all taught to ask, you know, at the 90-day review, like knowing what you know about this person and this role, would you hire them again? But we tend not to do that, right? companies like to make incremental change because it feels uncomfortable, I guess, to make more radical change. And this is the conversation we had in this boardroom because the CEO is very, very AI-focused, in part because their business got pretty disrupted by AI. They're— it's a market research firm. And he was basically saying, I don't want to be incremental. I actually want to ask the question, how would I do things fundamentally differently? In his case, and I'm not saying AI needs to mean that, you know, take 50% of the people out of your business, but he basically took the business down to like half of its employee size, including firing his of engineering and his head of product, 'cause they just could not wrap their hands around these AI tools. And again, he was deep in this and he was vibe coding himself and things like that because he was like, this is how I'd build the business today from the ground up. I mean, obviously, again, in this case, we're, you know, like rebuilding the plane a little bit as we're flying it 'cause it's a big business, as I mentioned, and it's growing. But he asked that question. I think that's really hard for people. And by the way, it was difficult obviously for the people that ended up leaving. They just did an offsite. He sent me a couple videos from the offsite. The energy of the people in that room, the people that are really embracing this new way of work, it was infectious. Like, I got excited just, you know, watching these videos that he sent me over text yesterday.

Yeah.

So that's how I think about it.

That's powerful. It sounds like he didn't fire his head of engineering because the head of engineering was superfluous. It was more like the head of engineering was dragging his feet in making this change.

100%. And he's replacing the head of engineering. But the head of engineering was like, hey, how do we add coworking tools to make each engineer 30% more effective? As opposed to saying, if I was gonna build an engineering team that needed to both support this existing team product, but then also work on these new tools. How would we do that? And how can we actually create these new tools? And the experience the CEO was having was he was off on the weekends coding up new things that ended up getting put into production. And he's like, why can I do this in a weekend and you guys can't, you know, do this in 3 months? And he needed to find someone else who like really embraced that. And look, I get how challenging it can be for people to embrace AI. And I, I'm sure you and I could think of examples where we were slow to adopt some of the new tools. 'Cause it's just like, ah, I'm just used to doing something.

Oh yeah, yeah. Workflow is, um, just your normal workflow habits are very insidious actually.

Yeah.

And they really keep you stuck in a way.

And I imagine as a CEO coach, that comes up all the time, right?

Yeah.

People get stuck in how they do something and it's just hard. I mean, I think that's the power of coaching, right? Is you get someone from the outside saying, why, why are you doing it this way? Like that, right? You just told me that it doesn't make any sense. So, you know, you push 'em on that, right? I'm sure that's a huge part of your practice.

Right, totally. And it sounds like to me that one of your biggest pieces of advice for CEOs right now would be to ask the question, if I was starting the company from scratch, what would I do? do differently? And probably who would I hire differently? Is that right?

Yeah.

Is there more advice you would give CEOs right now?

I would change that statement slightly, Alisa, 'cause I, I think this is important. When you ask someone what they would do differently, they anchor on how it is now.

Yeah.

Great point. Right? So I would actually, when I have this conversation with CEOs, like, no, if you were building this from the ground up, how would you build this? Right?

Yeah.

What would this organization look like? It's funny 'cause we often would ask CEOs to do an exercise. I'm sure, again, I'm sure you do this in your practice. As well, which is like, hey, 18 months from now, give me your org chart, right? What will it look like as you scale and get bigger? And that was to put people in a mindset of like, okay, do I have the right people in the right boxes? Suddenly you've got someone and they've got 20 people in their organization and it spurs a conversation about, hey, can that person actually scale to that? What we're talking about is like fundamentally different, even more radical than that, which is sort of saying, hey, I'm just gonna build a business from scratch that does the thing that we do. and at our size, $10 million, $20 million, whatever it is, how do I actually orchestrate and how do I think about that org structure? And that I think is a really powerful exercise.

Yep, I love that. It sounds like what also you might advise CEOs, and tell me what you think about this, like the founder you were talking about does, get your hands dirty with the tools. That's something that I really encourage people to do so they understand themselves, the power, the use cases, but also limitations right now today of what's going on out there. Do you agree?

I think you have to, right? I mean, I think, and look, I get the fear of it. Like I was not thinking about jumping in into Claude Code 'cause I'm not really a coder. And I was like, I don't know, maybe that's a bit too much. Now one, I think that was a mistake anyway, right? Like I should probably have been using it before. Anyway, I decided to do it and it's been a really powerful experience. And now I have a better sense for like, what does it mean to vibe code? Like what does that actually look like? How do I architect, you know, how do I connect Claude Code? The amazing thing about these tools, by the way, and I'll pick on Claude just 'cause I know it the best, is when you get stuck, you just ask it what to do, right? Like I'm trying to update something or, you know, I'm trying to like, like whatever, figure out how to connect to Asana, let's say, right? That was something I did early on 'cause I like to manage my tasks through Asana. And it turns out I can both push tasks to Asana from Claude, but I can also ask it to go grab a task from Asana and then do it. And I didn't know, I just was like, I don't know how to like get this set up. And I was starting to like do some web, you know, like what do you do? You go to the web and you research it. And I was mentioning this to Brad and he was like, don't go to the web, just ask Claude how to do it. And so I went in and I asked Claude how to do it. It was like, oh, here's what you need. And it walked me through it step by step, you know, and it was like, do you want me to do this? Do you want me to do this? And I was like, yes, yes, yes, yes, yes. And like, I don't know, 2 minutes later I had a sauna connected through Clubhouse.

Remarkable. Remarkable. It's really incredible. We are definitely gonna move away from AI and talk more, uh, largely about themes. But before I leave this topic, I wanna ask you, what are you advising your kids to do now? 'Cause you have 2, what, high school age kids? Is that right?

I, I have 3 kids. One is still in high school. 2 are graduating from college this year.

Okay. Okay.

So, yeah, I mean, it's interesting too, cuz one of 'em is an artist. So, you know, some of her classes, I mean, she's taking non-art classes as well, but some of her classes, you know, she's literally creating things with her hands, which I love. And I think is maybe a little bit AI resistant as well. Like good, you know, art, especially sort of 3D art, is not easily replicable with AI. But, you know, I think, and this is the advice I'm giving everyone, like lean into AI. You know, I show them what I'm doing. This is what you can do with AI, and I'm happy to set you you up on some of these tools that are a bit more advanced. It's funny, when the girls were first years in college, one of them, their school said you can't use AI. And I sent a note to them basically saying like, this is completely effed up. Like, this is not okay. And I want you to know I'm telling my kid they should be using AI. And if that's your policy, then we should find a different school because you're not training people to be prepared for the world if you're not teaching them how to use AI. I think it's incredibly important. I'm a trustee of my college where I went to, Macalester in St. And one of the other trustees and I have been really leaning into AI for this exact reason. We actually had a group of professors from school go out to Palo Alto with us and really like have a 3-day retreat on how to use AI. We had executives from LinkedIn and Google and Microsoft, a bunch of other places come in and present and just show them the tools. And then we had lots of discussions about how do we integrate AI not just into the classroom, but also in their own work in ways that are correct and authentic and things like that, that aren't like replacing feedback, let's say, that a professor might give a student, but augmenting it in ways that are, you know, are powerful and help them scale the work that they're doing and have more impact with their students and their teaching outcomes. Right. Which is what they care about.

Yeah.

And so like, that's how I think about everyone using AI. Right. And so that's the advice I give my kids.

So lean into the tools.

100%. And like the hardest thing is getting them to use it beyond search. Right. Because I think that's where most people stop. stop using it. And it's a more powerful search tool, and that's great, but I really am trying to encourage them to figure out how do you actually give it tasks to do and offload some things. Even if it's 90%, you know, you could do the thing in 90% of the time or whatever it is, you still wanna just play with it and understand what the capabilities are.

Right. And also to begin to ease it into your workflow, which is the whole point, right? Yeah.

Yeah, 100%.

I love that. So I wanna go back to the beginning when you guys founded— I love saying that, founded Foundry. When you guys founded Foundry, You hired an organizational consultant and she helped you pre-founding. And as far as I can tell, she still works with you. Tell us more about that. Why did you decide to do that? What were the characteristics of these 4 people that said, I know, let's hire a coach, right? And that, that kind of led you that way.

Yeah, Nancy has been with us since we started. And I think we recognized coming together that we needed maybe a little bit of help. We wanted to be thoughtful in organizational structure. We were all pretty close, but we'd had some different dynamics, right? I mean, think about sort of like the transition I made. I had worked for, for, like I was an employee of Brad, right? For whatever it was, 5 years before we started Foundry, really 6 before we had raised the fund. That's a very different dynamic than being a partner of someone. And we wanted to be really thoughtful in terms of like how we built that organization. So Nancy helped us do a lot of pre-work before we even had a name. We weren't even Foundry.

Like what kind of pre-work?

It was a lot around how do each of us like to work? What's our work style? It wasn't Enneagram at the time, although we've since done that, but we use this thing called the DISC And that spurred then a facilitated conversation that Nancy facilitated, where we talked about our different work styles and how that might cause friction, how that might come together, show up in different ways. So that was really, really helpful. We used it to create a cadence of both feedback to each other and also a cadence of how we were gonna work on our business. We had all been at a very large Silicon Valley-based venture firm, SoftBank Venture Capital, which eventually became Mochi. Mobius Venture Capital. And that had been a very traditional stovepiped hierarchical— at one point when I was there, it was like 80 people. I was a cog in the machine of Mobius, and we wanted to build a very different firm that was going to be much flatter. We were equal partners, just very different than the way that, or the environment that we'd come from. And we just felt like we needed help. So Nancy was with us. I mean, she still is. I truly most recently talked or emailed with Nancy yesterday.

Right.

So she's still around and helping us a lot. And by the way, it's helped a number of our portfolio companies as well. But we felt like it was important to set that cadence up. So for us, that looked like quarterly offsites where we would spend time together working not just on the portfolio, but on our firm itself. And then, you know, lots of sort of social time together. That dynamic has changed, right? When it was the 4 of us, it looked one way. Now Jason's retired. And so now there's a new partner. So that dynamic has changed and we're at a different point in our lives as well, right? We're not like vacationing. Together in the same way that we used to and things like that. And of course, we came into the new partners with existing relationships, and that probably made it even more important to have Nancy involved because we, you know, we had several of us that had been very close friends for a really long period of time, and then we're bringing in some new people. I think coaching is really important, and I've— I mean, just personally have used coaching several times in my life to help me be a better version of myself. One was organizationally with Nancy, which is ongoing. Another was— and we can talk about it more if you want— but I I like broke, like, I don't know, 15 years ago. I was like, I cannot scale. Like, this is not working. And I hired a productivity coach and he really changed a bunch of fundamental things that I was doing in my workflow. And then the last is— what's that?

Sorry, I didn't interrupt you. I wanna hear the last, but what did you change?

The last is now.

Yeah.

Because Foundry's going through this transition. You mentioned it earlier, but we're not gonna raise another fund. You know, I'm like, I'm old but not that old, right? I'm in my early 50s. Like, I've got a lot of energy, as people can probably already tell. Like, I just, you know, I'm not ready to, like, just sort of walk off and be done. And I feel like I've got a lot more to give back. And so, I want to be thoughtful about that transition and kind of the next phase. I have a couple of ideas of things I might do. It occurred to me that maybe it would be helpful to have someone kind of help me do that. But I'm also trying to be thoughtful about, like, how do I want to spend my time and what are my priorities? And like a lot of people, I sometimes feel like my calendar and my life, because of that, kind of gets out of my control. And I felt like I needed some help with that. And so, anyway, those are the 3 times. that I've spent time in coaching. Specific to productivity though, yeah, I mean, boy, did I change a lot of things, right? I think my next book is going to be about productivity, but I'm much more deliberate about my morning routine and setting my day up. And so I, I am very thoughtful about that. I do the same thing every day.

So what are your practices? I—

the second thing I was going to say, and this is important relative to the morning routine, is that I don't use email as my, like, control center. I work in email when I need to work in email, but I don't just back to email and default. I use Asana. There's lots of task management tools. But that became an important part of my morning routine. Because what I would typically do is look at my email and try to get through that before I took a shower or worked out or whatever I was going to do in the morning. And I think a lot of people do that. And now I don't. Now I start my day by going to my calendar and seeing what I have to do really that day, and then sort of the next couple of days. And then I go to Asana. And I look at the tasks that I didn't get done yesterday in the context of the calendar that I have both today and upcoming, I write down kind of the key to-dos, like what do I need to get done today? And that's the next thing. Then I order those things so I know kind of what order I need to do things in. Then I scan my email just to see if anything's come up, but I don't respond to anything and I don't like move things around. And that's my morning routine. None of that involves actually doing any email, and all of that involves like setting up the day for how my day is, right? I do separately twice a week, I look at my calendar and just Do I have the meetings correct? Do I need to adjust something? Do I have a day where I've got too many back-to-back meetings where I need to create some space? I have some pretty specific rules that my productivity coach helped me put into place about what meetings I'm willing to take, 'cause I have a lot of people reaching out to me. And one of the things I was actually able to do very successfully was create a heuristic for what meetings I was willing to take, but then also create really 2 things. One was pushing people to asynchronous calls, right? Meaning where we don't schedule time, but I just say, hey, I'm gonna reach out, here's my number, it'll be me. And that that helped a ton because now I do things when I'm driving and things like that. I also push people— I use this platform called Voxer, which is like a voice-to-text thing or a voice thing, but I push people to that and that's also helped. So that's gotten rid of a bunch of meetings. And then the other thing I did was I do get some very common requests. Hey, I just moved to Boulder, or hey, I'm looking to get into venture capital. And I created pretty lengthy email responses to that that I can reuse over and over again. So I'm trying to provide value back to people that I'm not able to meet But in a way that feels to them like I took some time and was thoughtful about it, even though the truth is I took some time once, and now I can repeat it over and over again. So he had me do those things, and that really helped kind of free up my calendar a little bit and be a bit more thoughtful about the types of how and where I spend my time.

Wow. I think that's so powerful. I especially love, you know, sort of— I get asked these questions over and over again, and so now I have this like sort of canned response because it's actually useful and valuable. And then also the notion of async. I think that people need permission to do those kinds of things. Otherwise they just feel— well, I think what people do is they're like, hi. Oh no, I don't wanna talk to this person. They kind of ghost them. Or they don't make good decisions about their meetings, so that takes up a lot of time. Or then they feel bad about not meeting with people. And so I love the permission that somehow you got to handle it in this way.

It felt like a middle ground to me. And it's funny that I had never thought about this before. I definitely felt like like I needed to be responsive to people, right?

Yeah.

And, and I felt like very core to the story I tell myself about who I am, especially back then, right? 15 years ago. So I was like a relatively newly minted partner and I was scrapping basically and, and, you know, striving, if you will. And I felt like I've gotta be available. Like I don't wanna be seen as this VC that, you know, would never take meetings and won't respond and things like that. So I respond to every real email that I get, right? Not blind copy stuff, but like an actual email. Everyone gets a And I'm still able to do that, but I felt like I needed to take meetings, and it was hard to tell people, oh, here's a 15-minute slot. You know, like that's what I started is like, okay, I'll go from 30 minutes to, you know, 15 minutes. And it turns out it actually works great to tell people, hey, I'm not scheduling, you know, sort of non-portfolio meetings right now, but give me your number, I'll give you a call. And I use the simplest app in the world. I actually should probably provide code, a new version of this, but I use something that manages my call log. And when I'm driving— I did it this morning. I had to drive to Boulder to have an appointment. I was like, okay, what's— who's next on my list? I called the guy, we talked for, you know, 15, 20 minutes, and, and that was checked off my list, right? I drove back, called someone else. And, you know, you— over time, that gets kind of— gets through it. And sometimes I don't reach people, and I usually leave it on them to call me back, right? Like, I leave the message, I was trying to be responsive, and if I don't hear back from them, then I didn't hear back. It's okay.

Yeah, 100%. I love Going back to Nancy and when you guys started the firm and her help, sounds like she really set up some great dynamics with you all. And also, I assume she was helpful in getting you guys to talk about things that were uncomfortable, having difficult conversations, talking about things you disagreed about. Is that accurate? And if so, how did you guys kind of learn to approach having tough conversations?

Yeah, so let me tell you the untold story about the founding of Foundry. We don't really talk about this that much, and I, I I don't think I've talked about it in this kind of public setting, but when we started Foundry, we were 5 partners, and that is sort of around. Like, if you look it up, people sort of acknowledge that. We don't talk about that much. We talk about Foundry really being founded by the 4 of us, really, because founding isn't like a one-time event, right? It's not like a point in time thing, even though we think about it that way. But the Foundry evolved over a period of time, and it was the 4 of us that evolved that. But of course, we started with 5 and we became 4. That means that someone ended up leaving, and Nancy was very impactful in helping us through that process. We had a 5th partner. He was someone we'd worked with for a long time. Like me, he had worked for Brad. He'd worked for Brad longer than I had, and he struggled to take the jump from being an associate, sort of junior partner at the direction of Brad, to being a partner in a venture firm, which is a very different style of job. And working. And Nancy really helped us as a group come to terms with the fact that it wasn't going to work out, have an initial conversation with him about here's what's not working and here's what we want to help you get better at, um, and then ultimately have the difficult conversation with him that this wasn't working and it was time to leave. So I mean, that's a highly personal story around working with her, but I think it would have been much more difficult to have navigated that conversation without Nancy. And then of course on the back side of that, we've just come through this relatively traumatic event. It was like a year, 15 months into the founding of Foundry, and that made us tighter on the backside. But everything all of a sudden got more important because then we were all key persons and, you know, things like that. And we were like, hey, we really need this to work out. And so that was, you know, I think again, having her along for those difficult conversations was really important.

That's powerful. If we were in the room watching you have this conversation, the first conversation with this person saying, hey, it's not working, What would we have heard?

Yeah. We prepared for it. So the actual first conversation was just me to him, 'cause I was the least threatening, I think, to him. And I don't know, I'm actually happy to have difficult conversations. I feel like that's part of my superpowers. I'm okay with that. And so I often end up having to do that on boards I'm on and things like that. But she helped us prepare for the way in which you describe that, as you know, as a coach, is really important because it can't seem like we are— we needed to talk about the job and what was expected and not about the person, right? It wasn't a personal failing that it wasn't working. It was, Because these are things that we need or that we want from you and that we think are part of being a partner. I still have that file, by the way. I did sort of like— it's still on my Dropbox. So that's what that looked like. And then there were some interim conversations because we used to do like at the end of the year in a venture firm, you've got sort of an unused pile of cash, right, depending on where you were against budget and things like that. And we used to have a very deliberate Nancy-facilitated method for doling that out. And for the first funds, we allocated a very small portion of our carry and then we allocated more over time annually. And so she She helped us work through that. And that one year that he was still a part of the partnership, that was a pretty difficult conversation because we were like, well, you're not doing the things that we feel like you need to be doing. And so we, we had a very difficult conversation around his allocation to that. And again, I think Nancy helped us frankly have the guts, if you will, because I think we could have easily defaulted. By the way, there wasn't much money left over. It wasn't like a big number. It was the symbolism that was more important than anything else. And I think we could have easily just defaulted to like, Look, it's early, let's just split it, whatever. And she really helped push us on like, no, that's not what you're saying. That's not the— she helped design the exercise we went through to like sort of figure out what that was going to be, um, and then kind of forced us to like have the conversation in the first place. So by the way, I think this is true for lots of teams, right? I mean, it's the reason why when many teams have an offsite, they should hire someone like you to like come in, because it's hard to be in the meeting and be facilitating the meeting, right? It is really, really challenging, and it also It creates a different dynamic because there's someone who's like in charge of the meeting, but is also supposed to be an equal participant in the meeting. And I just find it so helpful to have someone else there to play that role of being in charge of the meeting and facilitating and all those sorts of things. And Nancy is amazing. I mean, Nancy at Perspective 2, Nancy Ralston. So for people that are listening who are like, I need some of that, Nancy is great.

That's amazing. Plus one for the power of coaching and facilitation. It's amazing. But Seth, I wanna push you a little bit. What words did you actually say? I think that people, you know, are willing and able to like, okay, I know I have to have a hard conversation, but like, what do I say? And in my book, From Start-Up to Grown-Up, I have 11 scripts in the back of the book to help people have these difficult conversations. And I think it's so important to be able to get your mouth around the words. So like, can you role-play for us actually that conversation?

Yeah, I started with, hey, we need to have a hard conversation, and I want to acknowledge that it's going to be hard. I'm not asking you to react in real time because I'm not looking for that. I think it's important that you have a chance to think about what we're saying. I've written it out and I have a copy of that. I'm gonna give it to you when we're done.

Hmm.

So it started with that. And I, as a general rule, I think that's helpful, right? Like if you ask people to respond in real time, like the first thing they're gonna do is defend what they've been doing. And I, that's generally not productive, although it's not that I wasn't willing to hear pushback on it, but I wanted him to like really think about it first. So that's how I started it. And then I said, look, I wanna be clear, we are invested in making this partnership work and having you as a partner, but there's some things that aren't working for us as a group. I'm the one who's in here to talk about it because you and I have this good and close working relationship, and I want you to know that I'm personally— we are invested in it, I'm personally very invested in this. Um, but here are some things I want to talk to you about that we feel like are not working in the way that we'd like them to be working. And then I went through what that was.

What were they?

Gosh, I'd have to pull it up, but it was a lot of— You may not remember. I mean, to be a partner at a venture firm, you need to be self-directed, decisive, Thoughtful, responsive, a bunch of things like that. And in our case, we were in equal partnership, and there were some things he was doing that was weird, right? And a lot of it related to me because he saw himself as sort of senior to me in the sense that he had been around for longer, and that weren't part of what we were trying to put together, and that we and I needed to call him out on. And so they all related to those things, right? He was struggling to make decisions. He was not being responsive. He was coming across as very, um, know-it-all or sort of full of himself, and that was not the Foundry ethos. Um, he was treating me like a junior partner when I was a full partner. I think those were the types of things that were on the list.

Yeah.

And he wasn't making any decisions. He wasn't making any investments because he was afraid, you know, he kept sort of analyzing, oh, I need more data. I don't know. He just sort of struggled with all of those things. And I watched that live because at one point I said, hey, I know you've been looking at a bunch of things in Seattle. Let's go there together. Let's look at some of the companies you're looking at and let's make some decisions on what you want And he and I went up to Seattle, and he hemmed and hawed about, you know, a bunch of companies that he was interested in. And so, I also wanna be real here, Alisa. Like, I wanna tell you how this ended. I mean, obviously, it ended with him leaving. It also ended with the end of our friendship.

Hmm.

I mean, I believe that I did the best that I could do to preserve that friendship. And by the way, he was very close friends with my wife. We had one kid at the time, knew my daughter. We did a lot of things together. And when we finally had the conversation where we told him Told him he was leaving. I took him out to I guess it was dinner after that, and I said, "Look, I know this has been hard. I just want you to know, like I would like to stay friends, but I'm gonna give you some space because I know you're mad, and I'm hopeful that we'll get through this together because we've been friends. We'd been working together. I mean, until we moved to the Foundry office when we were in the old SoftBank Mobius office, he and I essentially shared an office. There was like a sliding door between us, but it was mostly open. So we basically had this one." big office and it was the two of us. We're constantly, hey, can you check this? Hey, can you look at this? He taught me how to create a cap table, things like that, right? When I first got to SoftBank and it didn't work. He stayed friends with my wife for a little while and then finally she was like, hey, I can't have this relationship outside of my partner, my husband. And I understand that's hard, but you keep calling me when you know he's out of town because you can see on Twitter that he's gone. And I'd love to stay friends and get together with you, but that has to be in the But I want to say that because I don't want it to be this sort of kumbaya, like we managed this thing and it was amazing or whatever. Like, it was really hard. Those conversations were awkward. It was the right thing to do, and it cost me a close friend.

Yeah, thank you for sharing that. I really appreciate that because, as you well know, it's hard to always see the kind of underside of what's really going on. And that's also why I was asking you kind of the details of that, because people don't know, and you've been through it. so successful and Foundry's been so successful, there's like a ta-da, you know, with a bow on it. And I think it is so important to expose, you know, what actually goes on, all the joys and all the sorrows, as the Buddhists say.

I wrote a post once sort of semi-related to this, not about Foundry, but I, it was like the 10-year overnight success or 10-year entrepreneur. I can't remember what I called it. And it was one of the things, and I talked about how like you just, you read the VC press or whatever, you start up press and it looks like everyone's successful and companies are like overnight night, you know, this, that. And it talked about how, like, that's not really how companies are created and how hard it is. And I don't know that I've ever gotten as much feedback on something I've written, particular emails and private notes from people saying, oh my God, I thought I was like the only one. Like, I've been struggling for years on this and it finally feels like it's working, but like, boy, it took me 7 years to get here. And I'm like, yeah, that's kind of how it works, right?

Totally.

And even some of the companies that people think— I mean, we just talked about Anthropic earlier. I mean, Dario left OpenAI in 2020, I I think maybe even 2019, like a while ago, right? And so it takes time.

It takes time. It takes time. And also really great companies are actually really terrible companies for quite a long time. And I think people don't understand that's the trajectory. It's not up and to the right. It's, you know, definitely like it's not working, it's not working, it's not working. It starts to work. And that brings me back to actually the founding of Foundry, which is that I think that you guys were trying to raise money for quite a while and it wasn't working for quite a while. And I'm curious I'm curious if you can walk us through that process as you were forming your venture firm and what you told yourself as you kept getting rejected.

Yeah, I love that you know that because I feel like you referenced this earlier. I think now here we are 20 years after the founding of Foundry and everyone's just sort of like, oh yeah, you guys came together and you had this big fund and your first deals were incredibly successful and, you know, now you've got $4 billion. And the truth is it was actually much harder than that. We really struggled. We came together in 2006. Jason and Ryan, our 2 partners who had lived in California, moved out in the middle of that year. We did a bunch of prep work. It was very expensive back then. You needed to write an offering memorandum. We were equal partners in that. I put in what at the time was my entire life savings, our entire life savings, my wife and mine. And we started fundraising in January of 2007. And by May, it was clear it was not working, right?

Not working.

We were getting reject— not working. We were not gonna be able to raise the fund. So much so that I actually had a conversation with my wife where I said, hey, I don't think this is gonna work. I think I've lost our life savings. I don't want to over-dramatize that. We weren't going to lose our house and things like that, but I thought we've lost the relatively little money I had saved at that point. But it was 6 figures and it was everything I had, everything we had. And I'm just going to have to go find a job of some kind, right? We had a kid, it was time that— we had 2 kids, sorry. And it was just time for me to think about something else. And she was like, hey, I think this is going to happen. Don't worry about it. Not don't worry about it like blowing it off. it off, but like, I believe in you guys essentially. And we weren't gonna give up right then, but we kept at it. And then we got a, a really big yes, right? Lindell, who's now my partner, was at UTIMCO, the University of Texas, and he said, yes, and I'll take 20% of the fund.

Hmm.

And that's what put us in business. And founders who are listening to this will appreciate it. Like, once we got that one big yes, all of a sudden we had a whole bunch of other people say yes. And we had, I wanna give credit, AMG, Chris Jacoby had said yes early on. Which was amazing, right? But it was a $2.5 million check. It just wasn't going to catalyze the whole fund. But I give credit to Chris always because he was absolute first yes that we had. And Fred Wilson put $1 million in from USV. And those guys had said yes early on, which I and we really appreciate. But it was Lindell and Utimco saying yes that actually ended up putting us in business. And then not only did we raise the fund, but we actually, we ended up closing on $225 million. We probably could have gone even more than that. And the original target had been $175 million, right? So it ended up being incredibly successful. And then of course, you know, our first investments were, you know, Zynga and AdMeld and Fitbit. And, you know, things did pretty well in that fund. And then all of a sudden we were like, okay, we can raise, it's not, not too hard. That story is important.

Totally. What did you tell yourself? So first of all, you get your first no, that's too bad. But like, then you're kind of realizing it's a stream of nos to the point where you actually tell your wife, I don't think this is gonna work. By the way, nice for her to believe in you. I'd love to hear what that meant to you. Yeah. But what did you tell yourself that allowed you to keep going?

Yeah, I mean, I think this is where it's been helpful to be very close, to have had some context, right? We didn't just start working with Nancy. We had already been working with her for probably a year at that point. And we basically said, we believe in ourselves and we believe we can do this. And, you know, we're going to give it more time. And I can't remember exactly how we said it, but I want to say we said, look, we're going to keep— and this is very Brad, right? Like, one, being optimistic, but also like, hey, let's be realistic We're going to give it until X, and if we still don't have momentum by X, it was probably early fall, then yeah, maybe it's time to say, okay, this isn't going to come together. I think that's kind of how we dealt with it. And by the way, I think that's not a bad sort of allegory to how other companies, others might work. You need to stick at it. You need to give it a real period of time. Fundraising is hard. We knew it was going to take some real time. And again, it wasn't about getting to a close, although we did end up getting to a close by November and a big one. We essentially closed on almost the entire fund in the first close. But it was like, look, if we don't have real momentum by September, then, you know, let's revisit this. It may not really be working. That's kind of how we came together and kind of dealt with it. And it's helpful to have optimistic partners. And again, Brad is always the sort of eternal optimist. So, you know, I think that helped as well. And fortunately for us, we stuck at it long enough for it to actually happen.

But I'm curious, like, how did you handle personally the feeling of like, oh God, I don't think this is going to work? You, you know, again, you had a small life savings, but nonetheless, it was your life savings. Like, was there a pit in your stomach? Or do you be like, all right, well, action solves everything? Or like, how did you comfort yourself?

I was pretty stressed out about it, right? Because, you know, we had 2 kids by then. I was— I mean, I remember joking with my wife that like, I'd been a VC at this point, it was 2007. I'd been a VC for 6 years. Like, I don't know that I'm super qualified to do anything from here, right? Like, what is my job going to be? And what does that mean for our life and all of that kind of stuff? And so I definitely remember feeling, you know, pressure around making something happen and finding some sort of backup, right? And I felt that my backup options were not great because I wasn't sure what I was qualified to do. And sort of going back into the job market felt pretty scary. I had really only applied for 2 jobs in my life. One was the very first job I had after college, and then the second was the job that was at SoftBank. And I was like, God, I don't know that I'm ready for that. So, you know, I think that I needed to convince myself. And again, I think my partners helped me do this. Like, we were not stressed and we didn't act stressed as a partnership, even though I felt stress and pressure personally.

Yeah, that makes sense. And so that can kind of like almost bolster you in a sense while you're going through it.

Yeah, feed off of their optimism, which I think was really, really helpful.

Yeah. Well, as we talked about at the top of this podcast, Brad Feld, your partner, one of the most important people in your Also pretty chatty, and you're pretty chatty.

Yeah.

And Brad has a pretty well-known blog. You also have a blog, and I'm curious, what made you start writing and sort of sharing your insights? And so I would just also say build your personal brand. Why has that been meaningful to you?

I started blogging very early on in like venture capitalist blogging. I was still an associate at Mobius, at SoftBank Mobius, and I kind of had it in my head like I need to build my personal At the time, I was not thinking I was going to have a career in venture. I was thinking I would do something else, right? This is just a couple years into SoftBank Mobius. And also, I mean, to our point earlier about like, you just got to get your hands dirty and play with the technology. I was interested in RSS and blogging technology. Again, it's brand new. This is like 2003. It's brand new. And so I wanted to like really play with it, but I felt like the voice of someone who was up and coming in venture, not a partner, might be interesting to have. add to the mix because there were a few people. Brad was blogging, Fred Wilson was blogging, a couple of others, but not many. And I thought it would be interesting. And then, you know, I like writing. I mean, it's very different. I've written a couple books now, so that's very different type of writing. But I do not have a quiet mind, and writing is a time when my mind tends to quiet down, like especially so when I'm writing more long form, like in the form of a book. So I did it really— it was sort of selfish, right? I mean, I wanted to do it for me. I thought it'd be interesting, and I thought it would build my personal brand, and I felt felt like I didn't know how that would be helpful, but I figured it would be.

And how has it been helpful?

I think it's been, especially early on in Foundry when relatively few VCs blogging, I felt it was a great platform to build my name as a partner in venture. And so, you know, that's probably why I was much more active back then than I am now. Also, when you're writing long form, it tends to take up a lot of your time. So totally less time to be writing blogs, uh, blog posts. But I did feel like it was incredibly helpful for me to build my brand. And even if people didn't follow it as I was, let's say, pursuing a company, I would send, you know, send them to my blog and say, hey, if you want to know a bit more about me, here's 5 posts that I think are interesting that you might, you know, that might be relevant to you, right? And, and I would change those up depending on who I was talking to, but it was a really good way to sort of be a little bit vulnerable and, and sort of be— show people what type of person I was before I had any kind of real sort of broad, I don't know, reputation, if you will, in the venture and startup ecosystem, right? And it's, I mean, it's interesting to think back and look back on it now, because I've obviously, that's changed, right? I've been a partner at Foundry for 20 years. Foundry is well known. I get a little bit of the Brad pixie dust, you know, sort of sprinkles, sprinkles out on me as well. And so that's helpful. But, but, you know, if I look back 15, 18 years ago, when I was like trying to scrap for deals and, and, you know, show people I could be value added, like it was a really effective way to say, yeah, this is the stuff I care about. It's not that different, frankly, than what I now do with the books, which are longer form and more important and sort of deeper topics, because it's something I can give to people and say, hey, this will tell you a lot about actually who I am and what I care about, even if you don't read the whole thing and you sort of skim it. And I imagine you use your book in the exact same way, right? I mean, it's sort of lead gen for life, right?

Well, that's very well said, lead gen for life. I think all the writing I do, writing, and speaking and like podcasting like this is all lead gen for life. Because I think it's so important that you just said that it's not just for business. What happens is I write a newsletter and I send it out every other week and people feel like I'm writing directly to them.

Yeah.

And they'll say, oh, this came at the exact right moment or something like that. And first of all, hey, that's amazing. That builds my brand. Second of all, my mission in life is to make a difference. So I literally made a difference for that person in that moment virtue of sending out this newsletter to a whole bunch of subscribers. And people really have the experience of knowing me through that. And I think it's, you know, you get opportunities and you get interesting connections all by virtue of that.

Yeah. And it's, you know, I'm a big believer in like, we call it give first here in Boulder. And obviously Brad just wrote a book about it, but which was, which you did a great podcast on, but I'm a big believer in just sort of putting good things out there. Right. Like I actually would like to to have a life where maybe I'm not remembered specifically, but like some good things I did end up sort of outliving me, if you will. And one way of doing that is to put content out and affect other people, right? And I think that that's, you know, in the sports world, they talk about your sort of coaching tree, for example, and, you know, who are the other coaches that you brought up? And I think actually, to me, the measure of a success of a coach is less, less wins and losses and much more, you know, who did your coaching style end up spawning, right? And what was sort of the culmination, like the cumulative, that's a better way of saying it, success of all the people that are kind of down in your coaching tree. And I think about that a lot in terms of the work that you and I do. Like, do we, and you don't even need to know about it, right? Like your newsletter, it's great when people write back and say, hey, that came at the right moment. But even if they don't write back and then downstream it's like a big MLM, Right? They affect some people and they affect some people. And all of a sudden this thing that you wrote, you know, has had this incredibly like, you know, multiplying impact in the world.

Love that. It's so true. Yeah. It's so true. And the same is true of my book. And I'm sure the same is true of your books too. And, and you just came out with a new book, which I think is really interesting. It's like a rethinking of capitalism. So let's, let's spend a little time talking about that. What, tell us about the sort of the premise of the book.

Yeah. I co-authored a book or 2 books actually with the same person, Elizabeth McBride, friend By the way, to be clear, co-writer is not like a ghostwriter. And this new one is about sort of the evolution of capitalism. I was at a dinner in New York with actually the same company that I was telling you is sort of really embracing AI very differently. And this was a number of years ago, probably 5 years ago. And the CEO, it was just me and the management team sort of at the end of the dinner. And the CEO said, hey, you know, we're being asked to comment on all of these sort of social things, social issues of the day. What should I do? And, you know, Would you accept a lower return for us, like living a set of values? And I thought it was a really interesting question. So I took it to Elizabeth because I share, you know, she and I have a very close relationship and I share interesting ideas with her. And it was one of those questions that, like, you know, sometimes people ask you something, it goes in one ear and then you're like, 2 days later you've forgotten it. I'm like waking up in the middle of the night still thinking about this like a week later. So that's when I took it to Elizabeth. And Elizabeth is a journalist. And so her first instinct is like, hey, let's talk to some people about this. This is pretty interesting. And so we did a few, like, almost like informational interviews. We weren't thinking of writing, writing a book. And it turned out that was like a fascinating topic. Like, what's the role of business in our economy? But also like, where's our economy headed, right? Like, the role of business, at least under neoliberal capitalism, like the style of capitalism that we've been living under for 50 years, was to create value for shareholders. But did that really work? And oh, by the way, in 2019, and this is like a year or two later, uh, the Business Roundtable said actually, which is a group of CEOs from some of the largest businesses in the US, had said, no, no, no, there are actually other stakeholders that matter here— employees, community, environment, et cetera. And that sort of like real— we realized this is like a bigger topic, a bigger question. So we dove, I mean, headfirst into this. I mean, I, I'm not to disparage other VC books, but like neither of my books are the kind of like VC at my computer writing about my experiences, pontificating about things like These are deeply researched books. For The Capital Evolution, we talked to probably 100 people, CEOs, academics, people up and down the corporate food chain, corporate ladder, a bunch of businesses you probably never heard of, but that were working on innovative models, other investors, Pete Stavros, for example, KKR, Jamie Dimon from JP Morgan, like lots of— Dan Schulman, who's now the CEO of Verizon. He was the CEO of PayPal. Lisa Greenhall, who basically invented impact investing, like people like that. So very deeply researched. And the book is an exploration of like, where have we come from? What does capitalism look like? Not just in the last 50 years, but what did it look like before that in the golden age of capitalism? What's working and what's not working? And then where do we go from here? And we outline sort of some ideas about where we might go. It's— I would, I would think of it more of like a thought piece. Um, like it's not super prescriptive. We've got some ideas for what the future looks like or what the future could look like.

Yeah.

But we describe this choice, right? We're in this kind of messy transition. We've sort of moved away from neoliberalism to what, it's unclear, but this sort of like economic reality is affecting everything in our lives right now. And it's obviously permeating politics and populism on the left and populism on the right are not all that different. And certainly what underpins them are very similar. It's why, you know, Mondani and Trump get together in the White House and they kind of get— they kind of agree on a bunch of stuff and everyone scratched their head about that. And you're like, you know, like, again, populism on the left is pretty much the same as populism on the right, even if their prescriptions for what to do about it are very different. So we explore these themes in the book and in what I think is, or at least I've been told, is a very sort of accessible manner, accessible enough that it became a bestseller. So lots of people were, you know, were at least—

That's amazing.

Yeah, hopefully they read it.

But yeah, yeah, yeah, yeah. What— but, but Seth, give us a couple, maybe a couple of, um, thoughts to, to get people interested in. Like, you know, give us like 2 insights that came out of the book, and in particular, maybe in your exploration, 2 insights that maybe surprised you in your reporting.

So, uh, one of the things that surprised me was, you know, this— the original question, because my original hypothesis, and I think Elizabeth was there to was that, yeah, we are at a point where businesses are going to have to be more active. People don't trust government. People don't trust the media. And, you know, what's left? Well, businesses. And I realized after— we realized after spending some time thinking about it, like, we need to be very careful about that on 2 dimensions. One is that it's a bit of a power grab, right? I viewed the 2019 Business Roundtable statement a little bit differently, which was less sort of— I always sort of wondered how real it was. And it was important. And we talk about why it was important, whether or not, you know, they really, really meant it or not. But actually, it was more than sort of what they said. It was kind of a power grab. It was like, no, no, no, we're going to now be the arbiters of this. And we need to be very, very cautious about that. That's not necessarily the world we want to live in. So that was something that changed in my thinking around sort of what, you know, where we, where we came from versus where we are. And then the second thing was, you know, there's an important role for government here, but I think we need to be very cautious about what that role is. And so there's an entire chapter dedicated to this. It's called something to the effect of Government Is Not the Problem, But It's Not the Solution Either. And we prescribe a— and I hadn't really thought deeply about like, where can government be helpful and where does government get in the way? And so, you know, we tried to take— we tried to ask that question and we have some thoughts on what is the right role for government. So that's something else that I think I think I hadn't thought deeply about. I think I probably was more on the— when we started the work, on the sort of page of like a little bit more government is probably not bad. And now I actually think a little bit differently about that. I think a little less government might be right, but more in certain areas and a lot less in other areas.

Yeah, that's— I think that's really powerful and important. And you spoke to all these CEOs, including Jamie Dimon, and I guess I'm curious, what specifically surprised you from the point of view of talking to all the CEOs? What were their insights or, you know, ideas or the discussions like that surprised you?

Well, for starters, I think the line about where they— how involved they should be is not clear. Right. It was very— talking to Dan Schulman was very different than talking to Jamie, very different than talking to other CEOs. And in those cases, those are public company CEOs. We talked to some private company CEOs as well, as well as a bunch of people from, let's say, Patagonia. We actually were able to sort of get into some people from Chick-fil-A. We tell the story of Hobby Lobby, right? These are, you know, these are— I hadn't thought about them as connected as they are, but like Patagonia, again, Patagonia, Hobby Lobby, and Chick-fil-A are very similar in the sense that they're deeply values-driven organizations, very different values, deeply value-driven organizations that are private, right? So they can kind of reflect those values. And Chick-fil-A's kind of in the middle, right? We tell the story about how Chick-fil-A obviously had sort of got in trouble with people on the left because they're— not because Chick-fil-A specifically, because the founder said some very anti-LGBTQ+ things. But then later they had— they got in trouble with the right because they had a, you know, a VP of DEI, right? And interestingly got in trouble like years after they had promoted someone into that position. And so they're like kind of, you know, dealing with it from both sides, which I think is actually illustrative of like, you know, you got to be careful about your bedfellows. Um, but anyway, we tell, we tell stories like that that, you know, really speak to the sort of diversity of opinion about where, how, how and where companies should be involved. Jamie said something interesting to us, which at first I thought was kind of BS, and we pushed him on it, and I still didn't really believe him. And then the more I thought about it and the more people we talked to, I, I actually started to more embrace this idea. But he really tried to differentiate for values, expressing a set of values, and politics, which is like overtly getting involved in sort of like US politics, right?

Mm-hmm.

And I, you know, I think some have maybe criticized Jamie for perhaps not speaking out on some issues that, you know, they feel like he should speak out on. But I think that's really Jamie sort of saying, look, I don't actually want to get pulled into politics, as he said, don't get weaponized, right? He's watching some fellow CEOs get weaponized by one side or another who are very fast to sort of turn what you're saying into whatever it is that they're trying to do that they think is the right thing to do. And I think I better appreciate, and Elizabeth as well, I think we better appreciate this. There is a little bit of a line between, and it's a blurry line, but there's a line between values and politics. I'm not saying every company should be on one side or the other. Certainly these private businesses are not, right? I mean, Patagonia and Hobby Lobby literally sued the government. So that's very overt. overtly political. But I think for the most part, we want our companies to express values, whatever they might be, but not, in my mind, be as expressly involved in politics. And I know that some people, some of my liberal friends think that's terrible, right?

Mm-hmm.

Like, that's— I'm giving them a pass to do bad things and not stand up for these things that are, you know, basic human rights and things like that. And I understand and appreciate that perspective. And, you know, my politics maybe lean more, I guess, in that direction, although I'm relatively what we used to call centrist, I guess. And that's kind of the conclusion that we came to. And we really sort of outlined that in great detail in the book with some tension, 'cause Elizabeth and I aren't totally aligned in our views on this too.

Yeah. Yeah. I think what is important about it is that it is a very readable book and it's also really a thought starter and a conversation starter for people to sort of explore their own thinking. But Seth, this podcast is called From Startup to Grownup, so I can't let you leave as we wind down here without asking you about your observations about what makes a successful founder. So you've had a long career investing in founders, being around founders and startups, and I am just really curious, what have you synthesized or pulled out that are the top characteristics that will tell you that a founder will be successful?

Yeah, so I think it's a couple things. I think it starts with a deep curiosity. I think they put humility over Right? I think being humble, approaching the world with humility, being coachable, being able to get feedback, it's hard, right? I've certainly struggled with— I think I'm better at this than I used to be. I think when I was younger, I was very stubborn. And I'm probably— if you ask people around me, I'm still pretty stubborn. But I think it's really important to be open to that feedback. And I think that they are, generally speaking, the most successful founders we've worked with are somewhat— I'm going to say driven, not, not obsessed, but like somewhere between that driven and obsessed line of like the thing that they're doing, right? Because it's not a 9-to-5 job. It needs to feel like a mission, right? It needs to feel like something that you are deeply— maybe passion is a better way of saying it— deeply passionate about. So I think those are the, those are the things. You're, you're curious, you're passionate, and you have humility. You know, humility versus Pride. I think those are the characteristics of most successful founders. Not everyone, right? There's some examples of some deeply not humble, very successful founders. So it's not— there's not one formula, but that's the formula to work for us. And certainly it's the type of person that I want to work with, right? I look for that in our founding teams because that's the kind of person that I want to spend the next, you know, 10, 12-plus years with, right? I mean, the venture, you know, Venture exits used to be 6, 5 or 6 years, and it was 7 or 8 years. Now it's, you know, 10, maybe even 15 years.

Yeah, it's a long journey, that's for sure. Just a couple more questions. What do you wish you had known earlier on your journey?

I wish I had known that— well, I mean, really, I wish I'd known it was going to be okay. I spent a lot of time sacrificing things in my personal life and with my family because I thought I needed to be everything everywhere all at once to You know, paraphrase the movie. And I didn't need to be, right? I think it's as one of the things that I have realized as I've gotten older is that you don't need to say yes to everything. And I understand there's maybe a pushback on that, which is like, well, you're successful because you did those things. But I actually think I could have done 60% of the things that I did and still been just as successful, right? Getting on an airplane and going to New York 13 times a year for the first 3 years of Foundry. It was— I mean, I did a bunch of things in New York, and it was before New York was like a big startup thing, and that's part of why I did it. But I think I could have gone 6 times a year and been just as effective, right? And I think that, that I didn't understand that. I didn't realize that. And I also was not maybe sort of kind to myself in every sense of that word, right? I, I pushed too hard. I was gone too much. I, uh, and then when I was gone, I felt like I needed to be at everything. And so So I would have these days where I was like, you know, out at a breakfast at, you know, 7 in the morning and then, you know, meetings all day and then drinks before dinner and then a dinner thing and then an after-dinner thing. And I realized, and this is how I travel now, you know, I don't always need to do that. Like sometimes you just need a little bit of like self-care and kindness and it's okay to take an evening where you either don't go out at all or you, you know, whatever. So I think that, I think that that's something I really wish I had been more thoughtful about, right?

Yeah.

Which is like, where do I need to be and how do I architect this to be better to myself? And I love that people are talking about that more and more, whether that's making sure you have time to exercise or meditating in the morning or maybe not, I don't really drink when I travel anymore because I found that it just, I can show up better and it's just better for me and my personhood to not do that, right? When I'm on the road and I'm already, you know, my body's already a little bit stressed because I'm moving time zones and things like that. That— I'm not saying that everyone should do that, but I just like those things work for me, including scheduling some time to work out when I'm on the road and things like that, and just being okay with that, right? And saying, no, no, I don't, I don't have to do those things. Now, some of it is my kids are older, and so I'm, you know, it used to be I would go to these New York trips and I would, you know, I'd fly in late one night or early the next, early morning. Sometimes I took the red-eye from Denver, which is terrible because it's like a 3.5-hour flight. And I would just like, I would run hard for 2 days and then I'd fly home and I'd get home at 1 in the morning, which is really 3 in the morning New York time because I wanted to be home as much. And so I recognize that I get a little bit of time back to me because I can stretch that out another day or maybe my wife can go with me or, again, my kid, 2 of my 3 kids are gone from from, from the house and the other one's in high school. So I, I feel less pressure around that. But I think I could have figured out— again, if I, I wish I had traveled fewer times and, and maybe extended those trips by 12 hours to be more kind to myself.

Yeah, that's very powerful. Very, very, very, uh, does that resonate with you?

I'm not sure.

Yeah, totally. I was just thinking how much it resonates with me. I mean, I used to take so many red eyes, and there was a point I I was like, you know what? I've earned the right to be more mindful of my time. No more red eyes is one of my rules.

Yeah, 100%. Yeah, it's good. And I think, I mean, people strive when they're younger and they feel like they need to do that or they need to show up at every event or they need to go to that conference or whatever. And I, you know, the advice I often give to people, it's like, it's how I feel about buying clothing, right? Like, I'd rather buy a smaller number of really, of high quality things, especially now we're on Zoom all the time. Like, no one really sees me most days anyway. But like, I think that that's sort of an allegory to how you can live your life, which is, look, pick the things that are really impactful. And of course, lean into those, spend time. And I'm not even saying what that is for you, right? That could be going to Upfront if you're in the venture industry or whatever conference it is. But like, feeling at least like I did, like I needed to show up to every single thing all the time.

Yeah.

I think just stretched me too thin. And I clearly wasn't my best self put all those things. And I definitely, you know, it, there was a cost of, in terms of not being around at home.

Yeah, 100%. Seth, last question. What advice do you have for other founders as they embark on their journeys to grow into leaders?

Well, there's 2 things and they might sound antithetical, but they're not. One is be bold, right? Like I love and appreciate this concept of boldness. I love the word because I think it's, it's sort of like this all-encompassing and it can mean different things to different people. You can be bold in different ways. different contexts. But the second thing is breathe. Like, I think sometimes— and again, maybe I'm just projecting kind of my earlier self— but like, taking a minute— I do this all the time, right? Like, when things get a bit busy and I, you know, it's better to be 1 minute late to your next Zoom or whatever it is, like, take a second and like literally breathe. Take a couple deep breaths in and it'll all be okay, right? And I, I feel like that's just helpful advice. I actually think those 2 things marry nicely together, even though they might I know that might sound a little antithetical.

I love that advice. No, I love that advice. I do agree with you. I think it's like once you are breathing, you can then be bold. That's the point. It's like, take a breath, take a pause, be intentional. That allows you with the energy and the space to be bold.

I love it. I love that word intentional, right? Intentionality. I think we, and I feel like this sometimes, I describe like my calendar, for example, often getting outta control. And I just, I think the issue is I feel like Like, I am not being intentional when those things happen. And if I can take a step back and be like, no, I'm gonna be intentional about this. And when my days get busy but I've been intentional, I have a very different reaction to it than when my days are busy and I just feel like I'm getting pulled by other people, right? And that agency, that intentionality, I love that way of thinking, Alisa. That's great.

That's great. Seth, I could talk to you forever, but I'm gonna let you go. This was such a pleasure. Thank you for joining me today. It was really great to talk to you.

This was super fun. I could, I could keep going as well. This has been really great.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.