Aaron White: Beyond the Exit: Sustaining the Serial Builder's Drive

28:01And that made all the difference in the end. So yeah, I do think it's artistic expression. But from what I know about you, your perseverance comes from this obsession that probably makes your entrepreneurial activities feel less like work and more like channeling your creativity. In the best cases, yes. Yes, that's true. But then in some other cases, I think it's like, you just don't stop. And it's there's no good reason. It's not because, you know, that, that chart around like capability versus challenge. And there's that flow section. Well, that's great when you're in flow. Wonderful. And if you're out of flow, cause it's too easy.

28:39Cool. You raise your ambitions, but when something is really hard and you don't feel capable of doing it, as long as I know it's not impossible, I can just grind it out. And that is, I don't know where that comes from specifically. I can't tell you that that's necessarily this desire to make, but it's just, I just, I somehow early on, I learned that you had to do that and I can't not do that. And that kind of makes all the difference because there are those gaps. You don't have to be that way. I think, you know, co-founders in a lot of ways help each other navigate those troughs. And it's like, listen, if you don't feel effective right now, I know you're struggling.

29:17I'm here with you. Like you go take a break, do this other thing. I'll do something we can control and then, you know, kind of bounce each other out. But yeah, for whatever reason, there are those times when I, I, I'm not sure it's pure creative drive to make. It's literally just, uh, I can't not do it and I just have to power through it. I, the closest thing I have to that is I ran a marathon once and, uh, you know, I remember how painful I didn't really train nearly as enough. I was doing it barefoot for weird reasons, but it was just so painful. And I kept just saying like, you know, this too shall pass and grinding it out even though I was not enjoying it my ego had you know died five miles back I I don't know why I just kept yeah so it's a combination of being pulled by your creativity and I guess being able to push yourself at the same time when needed so yeah yeah and probably because there's hope on the other side that look if you get through this the fun stuff, you know, will come back around, right?

30:20Pushing yourself because you believe in what's waiting for you. I'm sure you've had as many of these push and pull moments, if not more. Absolutely, absolutely. I can so much relate to it. So you've been writing this amazing blog called Singularity VC. And you know, I've been a fan for years. We talked about it earlier. um so would you say that blog helped you keep stability through your exits yes i think so so writing i think is just one of the greatest things that people can do um and if you can take the time to put something out there edit it make it useful to others that's a micro form of product right you know a company is a product a product's a product and a well-written article is also a product.

31:07And I think it's really helpful for not just others, but ultimately clarifying your own thoughts. You know, when I'm struggling with something, writing about it can be a very useful thing for me and me alone. You know, obviously diaries and journals exist, but this is like, I do like to do it publicly. So I get a little bit of, you know, benefit, not just to myself, but to others. So that has been helpful. And, you know, one thing that I focused on with folks is the storytelling element. I think some of my more popular articles that I've written for others have to do around how to craft a venture narrative, right?

31:42Whether you're raising money or not, doesn't really matter. But how do you tell a narrative that really paints this, wow, if this works, this could be big? How do you communicate that to others? That is something I'm obsessed with because I think more and more tech is weirdly becoming easier and easier. Actually, chat GPT great you can show up to that thing and learn almost anything about anything at this point fantastic yeah the stuff that truly differentiates companies it always has is how strong of a narrative can you put out there that others can absorb and repeat to you know their peers that's how some of the biggest companies get built it's just very you know very simple uber taxi on demand you know for mobile it's like some of these things are just so obvious but getting good at that storytelling has been very helpful for me and I think helpful for others.

32:33And so each of those articles is in its own way, a tiny little story. And now I'm dabbling with video too, because I think, you know, the world has moved, you know, increasingly, you know, into this kind of multi medium, but I will still write before producing something because I really want to make sure that I have something substantive that's exciting to learn about. So why are you doing that in addition to achieving clarity for yourself? Like now you're doing more video. Like, do you feel that you need to create your own kind of audience and it would be helpful for your future businesses? I'll explain to you why I'm asking you is because I have this mission to try to help some of my favorite super successful exited founders to speak more about what it is they're doing.

33:21I've noticed that some people learn the lesson of humility a bit too much. Like they succeed and then the next thing they do, they keep very, very quiet about. So I was hoping you will help me inspire them to think differently and share what they're doing with the world a bit more generously. Yeah. Okay. Well, so I am one of those people, which is part of the reason I'm doing this. There's a number of reasons. Number one, the more you tell your story, the better your story gets, the more you will attract teammates that want to work with you, the more you build a brand for partnerships or investors, and the easier it'll be for customers to find you as well.

34:05And I think, again, the more that tech becomes commodity in a way, the only differentiator is great story. And so it's really worth putting yourself out there to hone the craft. And you can't get better at storytelling by yourself. That's just not how it works. You have to test on others. And you can test it one-on-one or you can test it one-on-a-thousand, right? One-on-a-thousand, you'll learn a lot more quickly, but it's scary. And I think there's the normal reasons it's scary, you know, humility and shyness. For me, it actually comes from imposter syndrome, like deep down. It's, you know, if I put myself out there and I'm a little bit wrong, people who are far more intelligent on this topic will find me and shame me publicly and I will feel stupid.

34:50And then my whole world will collapse. Right. And that's just not true. It's like, you know, it's the Dunning-Kruger effect. It's like, look, if you're an entrepreneur, you probably know quite a bit about your domain more than probably the average. And so you not putting your thoughts out there is actually worse for the world. You're holding back on, on hard won lessons that fewer people than you have, please share them. People want to hear. And yes, you'll always be wrong on something and there will always be critics. But that's been true for you as an entrepreneur. You've had that struggle with customers and investors and trying to recruit.

35:25What's different about putting yourself out there like this? I think if you can get past that imposter syndrome and realize that you truly do know these things, you know, you will be so much better for it. Now, I'm telling you this and still feeling that internally, even with a smile on my face, even putting whatever of myself online, it's still deep inside of me. And I think just the way to break it is to form the habit. I think it's just practice. That's all it is. But you know more than you think and get over yourself and help others. Absolutely. I absolutely love it because people get very surprised when they hear that they may be selfish by not in a way self-promoting, right?

36:07It feels counterintuitive, but it's so true. if you just look at it from a different perspective. I don't remember. I saw some clip of a woman saying exactly this. It's selfish not to share. And that was the, maybe it was a TED Talk. That was the key. Oh, yeah. Like, got it. Now I can't unsee it. You're right. There are people, you know, younger or newer in the field than I am that want to learn this stuff. There are people that might want to work on what I'm working on if only they can hear about it. People might want to purchase it. People might want to follow along. Why am I holding it back?

36:40And I think what's really inspiring for me is on X, there's so many indie entrepreneurs that I follow. If you put a product out there, you might just see me show up and follow you because I'm just like, I know how hard it is to put something out there. And people who are public about not just the thing they built, but the process by which they're building it, talking about their struggles, some of which I know the answers to. Why shouldn't I follow them and support them putting themselves out there? you know they inspire me maybe one in a hundred times i can be helpful back like that's so cool so i get inspired by you know by all sorts of newcomers to their to their you know respective opportunities they can do it why can't i right like it's we can all kind of get better together so this brings me to my question about why did you decide a while back to become a vc several reasons not all of them good right i think the the the reasons the good reasons where I loved product builders so much that the idea that I could just meet with them all day, every day and learn new things about solar, about infrastructure, about this particular workflow for this type of business, this new sales technique, whatever, was just like catnip.

37:57Who wouldn't want to learn everything about everything? And the job delivered on that. It is a fire hose. Like people will come to your firm and to you and they will assume you're an expert on something. And I'm like, no, no, no, I know nothing. And I'm so excited to be here. Right. Which maybe isn't the right sales message if they're expecting, you know. Imposter syndrome again. Yeah. Yeah. Yeah. So like that is awesome. I think the bad reasons and, you know, I was young enough at the time that I thought when I got started with it that these were okay reasons was, you know, it was a little bit of a prestige factor.

38:33factor, maybe less so these days, oddly, but there was a prestige factor for me. And then, you know, you can make a lot of money, which is great. You can also make a lot of money as an entrepreneur, but you know, the idea that I could just be sort of like, I think having that opportunity all, I knew I had to try it, even if it ended up not being for me. And I do a lot of angel investing now, which is great. And it scratches some of that itch that I get to meet, you know, smart people, hear about them, and then participate in a very kind of lightweight way. the the crushing part for me when i was doing it professionally was you meet people who are throwing their whole self and their whole life at this one opportunity and the thing they're talking to you about getting is more fuel for their fire and 99.9 percent of the time you say no and i found that really soul crushing because i've been on that side of the table i know how hard it is to get where they are i know that even if one firm's not right some other firm might be or maybe they're not appropriate for this type of capital.

39:31But saying no is really, really challenging when you know someone's putting their whole self into it. Because it's not just like critiquing something. It's saying like, I don't want to be associated with you in this way. At least that's what it felt like to me. The other challenging part I think is, it can be very emotional for entrepreneurs. It was for me on the other end when I got no's when I was early in my career. And so in those moments, you never know who is going to be open to constructive feedback, even though you're saying no and say this might help you for the next investor, it might help with your product or your business.

40:06And who is going to be so deeply offended that they're going to try to fight you to convince you that it is a good opportunity, which is never a good idea. If you have to push on an investor like that, they're probably not the right investor for you. The ones that you want to work with will pull you along because you told such a strong narrative, you know, narrative matters. So that's just, it's very hard to tell people no. And it's very, it's harder still when trying to give constructive criticism is not oddly, it's not the best course of action. So like, if you've ever wondered why you don't get feedback from a VC, you know, the good ones will really suck it up and give it to you, but know that they're risking a lot of emotional conversations with folks because they never know which type of conversation they're going to find themselves in.

40:50In the end, I found not nearly as satisfying enough as just doing my own thing and kind of, you know, just building with people. I think the number one thing I missed was building with others on a singular mission. VC is kind of a lonely sport where each, you know, each person, each investor is kind of finding things. Maybe you're bouncing ideas off each other, but ultimately you're operating independently. I much prefer operating with a team. What's your relationship with angel investing? You know, it's a tough one for me a little bit because I know that if I really started, you know, turning my Sauron's eye to like doing it really well, like I'm going to be a world-class angel investor, I would be doing very different things than I'm doing right now.

41:33Because in a lot of ways I know better, right? But because it's my money, because the checks are smaller, it's easier for me to say, you know what, I don't have to think through all the eventualities of this thing. Like if you told a good story and I think you're a good entrepreneur, like that's enough, you know? I don't need to think about market dynamics and exit opportunities and all this sort of stuff. So it's a lot easier and emotionally rewarding for me to engage with. Where it gets challenging for me is there's a lot of things that your portfolio of entrepreneurs that you're working with, you could provide help for them.

42:11And there's just not enough time in the day to do your own thing and help others. And so that's a trade-off that doesn't feel very comfortable. So at the moment, I'm trying to keep it sparing, trying to keep it for folks kind of already in my network, just so that I already have a relationship with them in some way. And that makes it a little bit easier for me to engage with and not feel bad as though it was someone I didn't know and I'm getting involved, the pressure's on to help more. But I don't want that to be my primary responsibility. It sounds like through trial and error, you figured out what feels satisfying or fulfilling for you and what doesn't.

42:48And it's very satisfying and fulfilling for you to build things with the people you admire, while it's not quite as satisfying to invest or advise. That's right. You know, I can invest, I can advise at scale through better storytelling and, you know, more blog posts. That's my preferred way. and you know i think it's other lessons you learn as you get older is like it's okay to set expectations with people even if they're not what they want to hear and you know my best example is um dharmesh shah the founder of hubspot who's you know angel invested you know in a couple of of by my opportunities when he put money in he's like hey team just so you know i'm putting an angel check in but don't expect any help from me i'm you know very busy and i prefer to focus on what i'm building and i was like this is fantastic like we have a clear contract now for how i should think about this.

43:35And, you know, even despite that, he's still helpful at very critical moments. But, you know, don't let his portfolio know that. I have tried now to start setting those expectations with people I work with. Here's the kind of the space. And, you know, if that's not for you, that's great. But at least we're clearer on it. So I don't feel bad afterwards. Because managing my emotional energy here allows me to help you, but also keep focused on what I, you know, want to be spending the 90 plus percent of my time doing. You know, I've done quite a bit of angel investing after I had my first exit. And the reason I stopped doing it was that I actually realized that this is how I was solving my identity crisis.

44:11What I really wanted to do is some kind of label angel investing. And I actually considered also a VC label, but didn't quite go there. And when I was honest with myself and figured it out, that's when I said, you know what? No, that's not going to work. I wonder if you can relate to that because you did mention that identity was a big thing for you? Did you want to continue being this part of this ecosystem as I did? Totally. You had a very clear insight about yourself very quickly, it sounds like, which is great. I think here, I've seen enough people put on their profiles, you know, entrepreneur, investor, you know, and I'm just like, I don't think I need that badge.

44:54I mean, I know that it is easy to keep participating in the ecosystem of technology and feeling important if you can write checks to people. But I also have seen enough other folks go down that path that I knew it was more of like a plugging a hole, you know, a hole in your soul through this new honorific that like, you know, it just, it, I knew it wasn't going to work for me. So I have tried, tried not to make it my identity, you know, blog name to the contrary. I think it's just a very cool domain name, but it's something that I know can be catnip for exited founders is to just kind of like, well, now it's time to wear that hat and stay involved this way.

45:33And there's some prestige associated with it. But I'm glad I already had the investing experience because it already taught me a lot about what it would be like to do that full time. And so I knew not to go too deep. Brilliant. I know you mentioned that money has never really been a driver, but I still want to dig in that direction a little bit in terms of your relationships with financial freedom and how you see money as something that enables you to do things you want to do. There's step functions to wealth. I think that's something that I've learned over the years. Like I remember when I graduated from college and I had my first full-time paying job and I was earning enough that when I went to the grocery store, I didn't have to think about grocery store prices, right?

46:18I wasn't buying crazy things, but you know, when you're in like college and scrapping stuff together, it's like, sometimes it'd be like, okay, I got$20 to get me through the week. How am I going to make this work? Right. And you know, then with a full-time job, I was like, oh, I don't have to think about this. That is now a step function improvement in my life. I feel that. I have always kind of known that money was a thing to enable me to do other things, you know, not something that I had to be kind of like slavishly earning and squirreling away, that there's always greater opportunities. And so when I was saying that I would take time off between things, I mean, practically speaking, that means I've set aside a year's worth of savings to live a very austere life while I learn to do something new or build something or talk to people and figure out the next thing.

47:05So it has been an enabling force for me, even in small amounts, long before exits. You know, uh, that just requires living below your means, being a minimalist, being more passionate about building things than travel, you know, whatever, whatever your situation is with the exits, you know, I'd be lying if I didn't say a huge anxiety monkey jumped off my back. You know, I remember thinking that, oh, I'm in my forties now. And if I'm not successful, I'm going to be washed up. And then, you know, how am I going to have a family and a house and a happy retirement and all that. and like I'd never thought about those things before but the age kind of started catching up to me where it's like well listen you've been you know rolling the dice on entrepreneurship now for a couple of decades like maybe you need to change strategy here that went away thank god because I like building so much that if I had succumbed to those kind of internal fears or pressures real or not it would have redirected me to be someone that I'm not so it kind of the exits happened at the right time they're definitely a huge enabling force I don't have to make short-term trade-offs so I can focus on the long term far more frequently.

48:11When you're in your 20s, if you're trying to scrap together funds to be an entrepreneur, maybe you're taking different consulting gigs, sometimes you gotta take the opportunities that are in front of you. Some of them are good and some of them won't be. And now I really don't have to do anything that doesn't align with my passions, my interests, my compass, whatever it is. So that is hugely enabling. And even now though, I still find though that there's this paradox of not just the exit, but entrepreneurship where it's like, look, your company might be flush with investment, but you still have to manage every dollar very, very carefully.

48:43And so I still have this weird, you know, weird thing where I will like over-focus on optimizing some small things, even though I don't necessarily need to, but that it's, it still can be helpful. So I think it's about, for me, I can now make sure that, well, I might get caught up in that. I'm never sacrificing macro long-term opportunities for anything short-term. That's been a much easier thing to navigate, you know, as I've gotten older and had a few wins. So do you use this strategy in your wealth management? Yeah, you know, in my wealth management, that makes it sound like a really, you know, deliberate, systematic thing.

49:24I've got, you know, holdings in a lot of, you know, index funds, and that's real easy because I don't have to think about that. And, you know, um, and admittedly now I have an advisor as well. And so, you know, he's driving a lot of that. I have my, my gambling account, which is, you know, log into Robinhood on Monday and see what fun things happen in the market that week. And that keeps me from doing anything stupid with the bulk of, you know, my, my, my, my dry powder. Um, and then I have a lot reserved for, you know, angel investing, being an LP in venture funds and my own thing. And that's just sitting there ready to go and I I know that because I've got a now a foundation that I don't have to think about it's on autopilot you know and frankly will be okay no matter what like there's nothing that can happen to me that's gonna make it so I'm living you know in my office again uh like that it allows me to look at that other you know pile of dry powder and say what can I do with this you know like how much of a stone to carve off for this opportunity go for it that's really exciting.

50:25So I like to separate it into a honeypot for my impulses, dry powder for the things I want to do to make the world a different, you know, hopefully better place. And then the stability stuff that I just don't think about because that's never what I've been focused on and much more of a, you know, growth mindset, keep going. But it's nice to remove all this anxiety and think, well, you know, worse comes to worse. We can keep living and eating and, you know, kids can go to college and all that. So it does sound like a very well thought through wealth management system. Well, great. Okay. Yeah. If that's well thought through, fantastic.

50:57If you got into the nitty gritty of which funds, which returns, which horizons, I'd be like, I don't know. But I know myself enough to know that separating it out into those three buckets, that was the big unlock. The reason I think it's very well thought through is because it's aligned with who you are and with your understanding of what's fulfilling for you, what's not, right? Because you're allowing yourself the freedom of supporting your creative initiative, however impulsive they are. But at the same time, you have the wisdom to understand that you need to remove all this anxiety about money so your mind can be free to create and chase that meaningful contribution that is so important for you.

51:39Yep, absolutely. So that brings us to my favorite question about fulfillment. So if you were to score your life from zero to 10 in terms of the level of fulfillment you feel at this moment in your life, what would it be? I'll probably rate myself higher this month than I've had, you know, like more time to decompress and travel over the last couple of weeks. You know, I'm going to put it maybe at like a six or seven, which may sound low to others. but also because I'm not unhappy. I'm actually quite happy, but there's a couple of big things ahead of me that I still want to do. You know, my wife and I are trying to start a family.

52:20I'm very excited about that. I think it's going to be very fulfilling and challenging and sleepless. And then, you know, I also have, I already know the next business I want to build and I know how big and interesting it could be if I'm successful at that. The scale of what I'm contemplating next is just entirely different than anything I've done before. You know, I've been trying to make big swings historically, but I think that it's, you don't know how big the swings are until you've raised your ambitions and seen what's possible. And now I'm contemplating even bigger swings. And I think, you know, with my maturity, my imposter syndrome fading away, my network being what it is, the scale of the idea that is, you know, it's a capital that drop, that combination of resources is just, I want to see what I can do with it.

53:06Um, and maybe I won't be more fulfilled on the other end of that if it's successful. Maybe it'll be the same level now, but I can't help but think there's just, there's something a little bit more around the corner really push myself and see, you know, what I can make and, you know, what kind of challenges I can get through. So I'm rating it much higher than I would have ever rated it historically, but I'm leaving myself wiggle room for, you know, deeper fulfillment, you know, on the sort of family vector and the kind of like, you know, career defining opportunity. It sounds like the size of your ambition lowers the level of your fulfillment.

53:39because you're basically saying it's six to seven because I have this huge ambition for a new family and I have this huge ambition for the next business. So it sounds like, okay, if you had those things, you would be nine or 10. It makes me feel maybe you don't fully appreciate where you are already. That could be true. But, you know, I think the fear, I'll tell you actually, I'm glad this is turning into a bit of a psychological vivisection here because you're not wrong. Like I can peek through my head with helpful prompts like this. Like if I were to tell you that today it's a 10, right? In my mind, for whatever reason, healthy or unhealthy, probably unhealthy.

54:19That says to me like no need to do more, right? And if I don't have a need to do more, then I'm stagnating. And if I'm stagnating, I'm decaying. And if I'm decaying, I'm dead. And so like not leaving upside to like want to go grab feels like death to me. And that's a pretty polarizing swing. And the reality is, and I think this is what you're saying, but I have not internalized this yet. I'm 42, soon 43. There's still lessons to learn. Fulfillment is not the same as ambition, right? Those things can be separate. They aren't for me yet. I can see how it would be. There's no reason saying 10 is incompatible with wanting to do more.

55:01But at my current level of maturity, they're still a little bit conflated. Yeah, because it sounds like you could think about it quite differently in your case, because you could say, thankfully, by now I know exactly what brings me fulfillment and what doesn't. Right. Investment, investing activity doesn't, but building does. And it means that I'm so fulfilled already because I can just keep doing these things better and better and better. Right. And then you suddenly you suddenly may feel more fulfillment. Also, it sounds like with respect to the family, you have quite a lot of anxiety or worry that you may not quite be as successful as you were in other endeavors, right?

55:46Which is not normal because you have no idea. I've got no priors to judge it against. It's one of those things where it's just a lot of unknowns coming at you all at once. And, you know, as entrepreneurs, like you deal with unknowns, but ultimately the, the, the motion is to try to like learn and take control of the things you can and increasingly expand the sphere of control. And, you know, with, with this, it's kind of like, there's the before times and the after times, the after times are very different, my understanding. So it does cause me anxiety, but I think your, your insight about fulfillment and how it should fuel and be a stabilizer while still allowing the ceiling to be as high as you want it to be.

56:27I would love to internalize that. I think that's going to take, you know, a few more years before that. I'm very happy if this idea was helpful. Very helpful. Very helpful. Hard, easy to hear and go, oh, that's correct. I think it's gonna be harder to, you know, make a part of me. You keep mentioning the importance of people around you. And I get it that it's extremely important for you to have the right kind of team when you're building products. But can you talk to me about your personal life? How do you choose people you spend time with and how intentional are you about it? Very intentional.

57:04The broken approach that I've had, just to like acknowledge it before I say it, is that I remember this being very true for me in my 20s and early 30s. Less so now, but very true, you know, to a degree it's still quite true is I couldn't be friends with people that I could not envision working with in some way. Like if I couldn't envision sitting down and making a podcast with you or, you know, writing, you know, an article with you or building a product with you or doing something together to make, if I couldn't figure out what that would look like, I would move on. And so I would kind of cultivate my friend circle to be filled with folks that I would be thrilled to do something with if ever the opportunity arose.

57:46Right. And that's really helpful because it kind of, you know, allowed me to have things in common, both sort of spiritually and pragmatically with individuals, which is a great basis for friendship. It's a little narrowing, right? Like, it's not great. There's lots of amazing people. Most people are amazing in their own way, and it may not align to the things that I'm interested in. And so it's kind of like it closes some of those doors. But, you know, I recall cultivating, you know, positively my friend circle. And I've also kind of deliberately, you know, evolved my friend circle by graduating away and moving on from folks.

58:23you know some it's unintentional I'm just busy and I'm a bad you know bad at following up in certain cases so I don't want you know anybody listening to think that they've been like called but there have been times you know where I have I have deliberately evolved my friend circle and I know what I enjoy doing and it's not sitting around you know watching the football game and drinking a beer like I can't do that I just I start freaking out it does not feel like a good use of my time. And so I've been very intentional with it. And my guess is, you know, my parents talking about business at the dinner table, kind of conflating like social and work at the same time is kind of the foundation for that.

58:59But yes, been very, very intentional over the years. By now, I've met dozens of entrepreneurs who appear to be serial builders to me, like you are, but they seem to be stuck after a life-changing exit because they have this trauma of how stressful it is to manage people, to worry about your business, and they simply do not want to go there. And they get stuck in this deep unhappiness because they, on the one hand, know that they need to keep building because that's who they are. At the same time, this trauma stops them. I wonder if you have any good advice on how to overcome that. That is such a real phenomenon.

59:44I was actually just having that conversation with someone yesterday, but I probably have that conversation once a week with successful people. I don't want to do something again, but the people part is the hardest part. Even active CEOs of companies will confide that to people in their trust circle. It's very real. People are very challenging in all the best and worst ways. I think the thing that the advice that I have is think back to, you know, the best folks you've ever worked with. Right. And if you just had to work on a team of 10 to 20 of those people, how amazing would that be? And most people go, oh, yeah, that'd be killer.

1:00:23Like, that's all I want to do. It's like, do that because now you're a better judge of talent. You're better at attracting, you know, high quality talent, discerning it, enabling people, you know to really like flex their their their muscles like you can do that you know when you start you don't know what you don't know if you've you know when you're building a business maybe you know how to hire for one role type because that's the thing you know for me that was engineering i don't hire engineers because i'm an engineer but sales people marketers support like what do i know but you learn those things as you go and so like you you start to become a better judge of you know those folks and your network gets better i think in this case the grass is greener right like yes people will always be hard but you know so much more than when you built your last team up that you can be way more intentional about it and lucky for all of us i think the world's just very different right now like you know i think sam allman said this uh you know he thinks it'll be a billion dollar company soon with just one person i don't know about just one person but i can tell you that i think you can get to like 100 million arr with like 10 to 20 people right like i think that's actually possible because the tech has gotten so much better yeah obviously still need a strong idea and you know strong pull uh from customers but you know those two factors the fact that you know how to hire better and enable people better and you already have a network means that your starting basis for your team will be so much higher quality than ever before and that you probably need fewer people these days than you know if it were 10 years ago like when you started the last thing that should that should inspire some confidence but it's the phenomenon is very real.

1:01:59I see a lot of people, you know, very upset about it. And yeah, it's tough because nobody wants to disappoint anybody else. Nobody wants to let someone down and say, hey, you know, I'm letting you down or the team's letting you down or I made a bad hire. Like this is not the right place for you. I'm sorry I convinced you to join this opportunity. It's actually a bad mismatch for you. Like all those conversations are just deeply painful. So the emotional exhaustion is real. I think the more you mature internally to probably helps. I don't have any good advice for that clearly still got a lot of growth ahead of me but uh there's a lot of hesitancy in folks to do the next thing for that the team yes but this is brilliant thank you i i love your advice very practical besides the trauma of uh dealing with employees and partners also the idea of how stressful building a business is is obviously another fear and uh you know we talked about it I love that post you made a few years ago when you looked back at how your weight related to the stress you had during different periods in your life.

1:03:03And I remember there was this really cool chart which showed basically your weight would go up when you were building a business, then it would go down when you had a period of rest, and then it would go up when you had to raise money from VCs and then would go down. And I thought it was so beautiful because it clearly shows how our body gets, you know, absorbs all this stress and that the price we pay for building a business is also clearly our health, not to mention our mental health. So again, I would love you to talk a bit more about that aspect and how you managed to overcome the fear of additional stress when you made the decision to go ahead and build yet another business.

1:03:46I need to do an update to that post because I've got a lot, I've got more years of data on it and it keeps holding true. Like high stress times, your body eats the stress just as much as your mind does. And it, you know, as you get older, that gets riskier and riskier in a way. You know, the stress, the stress really worries me. I actually feel, I think maybe it's helpful then I feel a little bit more stress not doing anything because that motivates me to do something, which is in a weird way, a stress reducer for me. Taking action always reduces stress on some level, maybe not in total, but, but it does feel better.

1:04:20I think the way in which I'm managing stress go forward is I have a couple of things that make things easier for me. Some are lessons anybody can learn. Some are specific. Like I have had some windfalls now, which means that the things that stress me out around the house, I don't have to worry about. We have someone come and clean the house. You know, we can do meal prep if we want to. Eating out or having order in is not a problem. So I'm not stressing about trying to plan grocery trips and this and that and cleaning and doing laundry and all this. I can kind of set a bunch of stuff aside. So, you know, and if the business folds, I'll be okay.

1:04:56That does remove a lot of stress. So that's nice and that's a post-exited luxury. I think the things that I can control that have gotten better with age, one is the know thyself. Like knowing what I'm good at, what my zone of genius is, is very helpful. Because while I still need to be a good judge of quality for other things in the business, I know that the more I can hand off to others, especially if it's their zone of genius, to focus on mine, the better we all are. And so I've learned to let go more. The thing that I won't let go on is speed of iteration. Because it's okay if you don't do as good of a job as I might dream I would have done with infinite time.

1:05:38But if you and I are iterating really fast, even something that's not quite right, we can make better with, you know, we can make predictably better. So that's the one thing I won't give up on. But other than that, I'm getting much better at handing my toys to others. Right. That reduces a lot of stress. And then, you know, that post is really interesting because I think, you know, that mind body connection works both ways. Right. Like, yes, when I am stressed out by the business's challenge, people challenge, fundraising challenge, customer challenge, runway challenge, my weight goes up, my sleep goes down, and my skin color goes gray, and like all these bad things happen.

1:06:14But I found out in 2019, you know, I'd always dabbled with running and rock climbing and things like that. But in 2019, I started lifting heavy weights. I'd never done that before. And it reversed the direction. It's like the more I got myself in shape, the more I wanted to eat healthy, the more I ate healthy and worked out, the better I slept. And the better I slept, the better I did at work because I just wasn't waking up in a fog. I had a longer fuse. I wasn't losing my temper. And so now a non-negotiable for me is carving out time in the workday to get those workouts in. Because as much as that hour and a half seems that day, like it's going to be the thing that changes the trajectory of the business.

1:06:54it usually isn't but if i start getting unhealthy that will change the trajectory of the business so yeah finding i would say finding some sort of workout that is really appealing to you whether it's biking running lifting whatever that is a lever you have that goes the other way which you know i didn't find that till much later i found the negative side and i found the positive side so they're just some some you know spread your toys around remove things from your life that you can and then learn that improving your health actually improves your well-being, which improves your ability to be more ambitious and do cooler things.

1:07:29You know, you've mentioned a big ambition a few times now. And I have to say that for me, one of the huge aha moments in my life was when I realized that the bigger my ambition is, the less stress I feel. Because I suddenly don't care about those small things, like what you mentioned before they become so small comparing to my big ambition my purpose that I just don't care and I don't stress anymore for me it was very paradoxical because I thought the bigger the dream the more scared I would be but it's the opposite the opposite actually I love that because I think a bigger ambition in a lot of ways results from a clear a clearer vision in a way.

1:08:14Like saying I want to be$20 richer isn't, is like, uh, definitionally clear, but it's not practically clear saying you want to start a company to, you know, build self-driving cars and have it, you know, deployed in every major city. That's incredibly ambitious and it's huge, but it, and it's also clear oddly. And you're right. It burns away a lot of those micro things. And so when you get caught up, you know, if you're trying to save$20, you might get caught up in how you're spending five cents here and there, you're trying to build a, you know, a self-driving, you know, international self-driving car company, you're not going to get caught up in those small things.

1:08:50You realize that spending any ounce of energy on that is a massive waste compared to these bigger levers you could, you know, go find and pull. And so I think maybe then what I'm hearing from you is it gives you, you know, it gives you more clarity. It allows you to not sweat the details, which both those things reduce anxiety. I love it. I mean, great. Everybody raise your ambitions. You'll feel healthier. Do you have a sense of purpose and what's your relationship with this word is? I've definitely done those exercises over the years, the ikigai's, you know, what is my life's purpose? I think I'm getting a clearer vision, you know, maybe.

1:09:30I think one reason my blog is called singularity.vc. You know, if you're familiar with the idea of the singularity. This is Ray Kurzweil. He said that, you know, technology has been on this exponential curve and we're coming up on the point at which it's going to be impossible to predict what happens afterwards. Right. I have always been obsessed with tech, even before I was working with it, because I would read a ton of sci-fi science fiction. I just could not read enough. And science fiction is very ambitious. Right. Like Star Trek's a great one. You know, what if we had a society where we'd remove famine and suffering and all this and we could explore the stars like what would that be like um i think that humans as a species and our societies right now i don't think we have most folks have any idea how much incredible change is coming in the next you know decade or two here like i think there's an immense amount and everything from you know cheap energy ai robotics advances in medicine this world is not going to look the same a couple decades from now.

1:10:33The future's not evenly distributed. It's not going to be everywhere all at once. But the things that we're hearing about in the news today, some of those titles are sensational and some aren't. I think my purpose is to really help pull parts of that future forward and just show people exactly how powerful the primitives that we have are and how bigger we could possibly raise our ambitions together if we can take care of those things. I would love a Star Trek future. That's what I'm hoping for. I think it's going be pretty bumpy along the way but i'm starting to see my purpose is in kind of showing people that what they think of as science fiction is about to become you know pragmatic reality and that's just so fun it's like being a magician right like here's the future like haha that's not real no no it is check it out you know apple vision pro came out last week and that's like one of the moments for a lot of people it's like the device has its challenges but like if you hadn't put your head inside VR until you put that thing on, that was your first entry into it.

1:11:30It should be mind blowing because like, wait, we could do this. Like that's incredible. There's so much more of that coming. So that's exciting. And I think that's starting to help me get a better sense of purpose. But it's interesting. It sounds like you are attaching that sense of purpose more to Singularity VC blog than to your future businesses or current businesses. No, those things, they'll line up. So you also want to be part of that future, not just through storytelling, but through actually creating. No, through like, you know, hands and brains. Is it Alan Kay, like the best way to, you know, predict the future is to make it?

1:12:06I want to make it. Like, I think I can predict which way it's heading, but I think it'll be even more satisfying not just to have written like, hey, hey, folks, I think we're heading this way. But like, hey, folks, look what I just did. You know, how cool is this? What can we do with this now? I think that's way more satisfying. So tell me about your typical day. Right now, with the post-exit hat on, my typical day is amazing because I have not ever had a day where I could just sleep and wake up when my body woke up versus alarms or anxiety waking me up. So, you know, typical day these days is I'll wake up somewhere between 8 and 10.

1:12:45No pressure to pick a time in there. It doesn't really matter. My wife and I have coffee. we do a little walk there's an island nearby that we walk around it's about a two to an half mile loop depending on how we do it we say hi to our favorite you know coffee shop along the way there and then i'll settle in to do a bunch of research and just learn about you know what i'm up to uh and so on one screen i've got you know just a ton of you know notes and links that i'm i'm trying to read and learn and remembering that like hey i i can read academic papers hey i can play with, you know, unfinished open source projects.

1:13:20So like really actively engaging. And on the other screen, I've got my sort of, you know, vision slash mission statement for the next thing that I'm building. And I'm constantly adding and amending to this narrative around what's the change I'm about to bring into the world. That will take me to about, you know, 2 p.m. when I've forgotten that I haven't eaten lunch and then we'll sit down and eat. And then I'll go to the gym for a couple of hours, which is great. You know, I get to get all the mobility I want and all the lifting, all the hot, you know, hot tub or sauna afterwards, which has just been so fantastic.

1:13:55And then I'll come home. I might, you know, read and work a little bit more and then my wife will hang out together. We might play a board game. I might, you know, play games online with friends. Maybe we travel out to dinner, settle in and read in bed, science fiction for me usually, and then, you know, repeat the next day. So it's pretty easy going right now. I know that once the next thing kicks in, you know, I'm at risk of waking up every morning at 7 a.m. because I cannot wait to be at my computer, you know, 15 minutes later without even putting, you know, like street clothes on. Just maybe I'm in my pajamas just furiously working.

1:14:28And then maybe that continues till, you know, eight or nine at night. So I'm trying to hold that off until I've established this kind of healthier cadence with my weightlifting and eating. so that when this finally comes around, it's from a much healthier base than I've done historically. So the days are easy and full of learning right now, which is awesome. So your last exit was in April 22, wasn't it? I think both of them technically concluded in February of 22. So basically for two years now, you have essentially given yourself permission to heal, to rebalance, to learn more things. A little bit.

1:15:07I mean, actually - Next big thing. One of those exits was very much into an active company where I took over, you know, technology and product. And, you know, that there's no relaxing when you're operating a growing business. You know, six months after that acquisition, I helped raise$150 million. You know, we grew the team from a combined$150, you know, on up through a doubling. Like, that is a very intense period for a company. So for the first, you know, first year and a half, at least there was no relaxing. Some things I could take care of, which was nice, but I was still very much in it. I would say over the last couple of months now, this has been the actual true post-exit period where I'm truly between things and I have, you know, a lot of kind of material concerns taken care of.

1:15:54Now is this time of healing. And it truly is kind of like healing, honestly. It's like fixing every broke thing about, you know, like, oh, I didn't realize I was duct taped together here and here and here. This routine that I've just described to you, you know, it's only a couple of months old, but it's pretty great. But it's only a couple of months old. It sounds perfect for the healing period. You know, I always try to encourage people to take their time and heal because I think a lot of what we see when people rush into the next business just to be disappointed and give up very quickly comes from the fact that they did not allow it.

1:16:30themselves to heal properly. Do you have any idea how long you think you'll want to keep doing that? That is a great question. That's a really great question. And, you know, some of the smartest investors I've ever worked with have said the same thing. Like, you must take this period of healing. It's kind of critical to not do it as to kid yourself. You know, in my head, I was hoping for three months. My friends were advising for at least six months. And practically speaking, if I'm not careful, it's going to turn into about, you know, only, you know, two months. So I am trying my best to hold back at really going all in too soon on the next thing.

1:17:11I think in practice, it's going to end up being like, you know, again, three, three-ish months or so, but I wouldn't be surprised if that was the wrong number. I wouldn't be surprised if it truly took six months to fully kind of detach and cleanse yourself from this need to be doing something. you know I mean I remember this happens every time I'm between things it's like those first couple of weeks I should be doing nothing like truly what is there to do there should be nothing going on but for whatever reason anybody who sends me any email about meeting up to talk about anything I'm just like you know those the first two weeks after I told people I was like you know moving on from one thing and didn't know what the next thing was I had more meetings that week than you know I've had in a long time and that was me filling the void of like well I don't have business meetings, you know, inside the company.

1:17:54So I must, I must need meetings outside the company. I'm past that now. Thank God. But yeah, I don't know. I'd be curious in your experience. Is it, is it three months? Is it six months? Is it a year? I mean, it probably depends on the trauma a little bit. I think it does depend on the trauma. Like for example, you seem to have very good idea how to overcome the most typical traumas, dealing with people, the stress, the fear, a fear of failure, the fear that you will not succeed again, because all these things we need to process and be comfortable with before we go forward. I did make every possible mistake the post-exit founder can do.

1:18:33And one of them was that after my second exit, I didn't just start a new business right away. I started two more businesses thinking that now I knew everything and I was so cool and it will be so easy. And nobody told me what happens to our motivation a few years after our exit. It doesn't happen right away. It actually takes a little bit of time. And I just completely lost motivation. So I ended up closing two businesses despite the fact that I had found product markets fit and I should not have closed them from purely pragmatic or financial standpoints. I mean, I sold them, but I sold them more like, team and assets, not the proper exit.

1:19:14And I took time off and I think I should have done it earlier and not sacrificing businesses I really liked. So it's personal, but I would always encourage people to take as much time as possible to heal. And especially if you are about to start a family, That's by itself the biggest venture you'll ever start. Probably, yeah. Yeah, your wife will need a lot of your support. You'll move together to a completely different type of relationship. So I wouldn't rush, especially given that you already had a few companies and sold them. Yeah, there's wisdom in here. My hope is that I can find a better balance go forward.

1:20:04by knowing how to attract, you know, stronger talent and hand my toys over to them and, you know, do more in a way by doing less, right? Like being a better steward of the vision and the culture can have a lot more leverage than getting your hands dirty necessarily. We'll see. I mean, it's open-ended right now. There's no immediate pressure. So there's time, but... I don't know if balance is a realistic ambition for obsessive serial builders, but taking some time off to restore your health and your relationships and everything else you need to restore is not a bad idea before you get obsessed again and start spending your time, your health, your focus on the next obsession.

1:20:50One framing that my wife gave me, and I'm not a sports person, but it stuck with me. She says, you know, I think your folks you work with, you strike me a lot like professional athletes. just like the level of involvement and stress and physical physicality and being, you know, going all in on a business. I think it can be very physical talked about before, you know, they also have like off seasons where they're doing like, you know, recovery and, you know, some lightweight training for a little while. And there's this kind of natural flow to it. And so knowing there are seasons to this, that doesn't have to be, you don't be continuously, you know, grinding and growing.

1:21:27You can take these periods of, of health and restoration. Yeah, that's probably a healthier way to approach this and just allowing yourself that like, no, no, this is part of it. This up and down is part of it. It's okay to have a story period. It doesn't mean you're worthless. All these insecurities, aside from the whole healing part of it, how will you know intellectually that this is your next big thing when you come across it? You know, it's a combination of things for me. one I like I said I've given myself permission to learn and you know the next phase is given my giving myself permission again which I don't need to but like you know articulating it but it's time to like experiment let's build some things and I've gotten much better at not being attached to any one thing but I do you know I mentioned that I would get together with friends and build something every weekend the critical thing for me there is it's okay to get obsessed and build something and it's okay to shut it down uh i'm very comfortable with with that motion you know you call it failure and being comfortable with failure but i just think it's you know you're taking shots some shots land some don't when something is at a combination of maybe like three things this is when i get really excited the first thing is uh i am obsessed with building it that's a great sign and i think that's just like for me i happen to have i hope the right judgment that when I'm obsessed with building something, it's not just because I'm in it for some esoteric reason, it's because it's got some broader opportunity.

1:22:59Two, when I tell others about it, they get very excited about it. That means the narrative is infectious, not just the product construction, right? That something about what I'm telling them is resonating and they go, oh, wow. And then third is when the rubber hits the road and a would-be customer is playing with it and saying, this is great, I need more of this. And when you feel that, that's when the lightning truly hits, because it means that I can build this. I enjoy it. I can attract people to it and tell a good story to sell it. And it actually seems to work. So those three things for me are the like aha moment.

1:23:35So, but in order to get there, you've got to give yourself permission to play with things, to tell people about things that might fail and to show things to people that you might not pursue. And so building that comfort with all three, but when those three things land, that's how I know it's, it's the right thing. And, you know, that's when the health starts taking the downturn if you're not careful, because it also means you're probably working on it like 12 hours a day, you know, seven days a week. But I actually love it how this approach would satisfy your most important needs in a way. Because if you look at what you just said from a different perspective, you're basically looking for something you really, really care about, right?

1:24:11You really love doing. You want this process of being in the flow naturally. then you want absolute clarity as to what it is because without that clarity you wouldn't be able to do good enough storytelling for somebody else to get excited about right so clarity is the second thing and then the last thing is that need for contribution which we keep talking about and you tend to call it proving yourself but to me it feels really more like you really want to matter contribute and do something really good for others so when these things come together i can actually see how everything will work right yeah it's beautiful yeah it's great when it happens and i think for me at least i can feel it viscerally i know when i'm faking interest in something i've scuttled enough projects to know when i am deeply interested in something i've shown people enough lemons to know when they're deeply interested in something.

1:25:10And I've told enough stories to know when I finally have a good one, right? So, you know, it's, I'm grateful that I've had a bunch of things that went nowhere, because it shows you the dynamic range between uninteresting on one of those dimensions to compelling. And that's a, you know, you kind of know when you see it, but you really feel it. And that's a, that's such a good, a good, you know, intersection. So for me, an interesting observation is that you never mentioned a business model as part of it. That doesn't excite me. I mean, there are elements to what I'm kind of noodling with and playing with that the business model is actually exciting when I think about it, but it's not the number one thing that gets me going.

1:25:47And I have seen this enough that people will get excited about a particular business model or fixated on a particular version of their product or a problem that they think is more widespread than it actually is. And that creates a very unhealthy tunnel vision because if the market doesn't want that thing or the market's not going to support that business model, you know, then all of your hopes and dreams are anchored into something that's increasingly incorrect, but it's harder to move away from it because you are attached to it. Right. Whereas something that the, you know, if you find pull from the market on anything, it's almost like the rest of that be damned.

1:26:25just pursue that because it will pull greatness out of you and trust yourself you'll be smart enough to find a business model that supports it yeah some of which are prosaic some of which are really interesting but it's not the thing i start with that's and there are folks that do that and i think that's awesome you know they see a market opportunity that's more structural that they're pursuing for me it's always been about new product experience not some sort of arbitrage of inefficiencies which is still very useful to the world but not where i kind of get excited about? Well, I'm not surprised because your motivation generally comes from building a product.

1:26:57So you wouldn't get excited about the business model. For somebody else, their motivation comes from desire to make money this way, whether it's because they like the money-making game or they just sort of want money for whatever reason. So in both cases, people are focusing on what will motivate them sustainably for long enough for this business to succeed. And in your case, it's building amazing products with amazing team. Yeah. And money will follow that. And I think, you know, of course, you have to be mindful of, you know, of it all along the way. And so it's not that I'm blind to the structure of how a company spends and earns its, you know, its money or the outcomes and their structure and how that impacts your own personal windfall, or your investors wouldn't fall or your teams wouldn't fall.

1:27:48Great. I've got all that locked and loaded in my head regardless, but it's not the thing that's going to launch me into something and sustain me. That's a second-tier concern for me in a way. If you're doing something awesome and the market likes it, then the rest is probably solvable. And so different if you're a CFO coming in, you should be excited about the models and what you can do with it. That's a very different type of person than I am, I think. Yeah. And the fact that you're so experienced and mature as an entrepreneur gives you that confidence that money will come. Because when you look at people who just start in businesses, they don't have that confidence to say, oh, I'll be creating an amazing product people want, money will flow.

1:28:31Right? They can't. They don't know for sure. And I love it that you do. That's hard. Which means that you'll be immensely successful in the next business, I'm sure, when you find it. As long as it's a lot of fun. and a bunch of really smart people choose to work with me and I keep good health for myself and my family, it'll be a win no matter what. You keep an eye on that weight change, right? Aaron, this has been absolutely amazing. And I have just one last question. How do you want to be remembered? Oof, that is a great question. As someone who is always excited about what they were doing about what others were doing.

1:29:13And if that's how I'm remembered, I will feel really good about myself. Beautiful. Aaron, I wish you the best luck with your family, with your health, with your healing process, and with your next business. And I'm very, very grateful for this interview. You gave me so many golden nuggets and so much inspiration for my audience. I just can't wait to release it. Thank you so much. Well, thank you so much. Such a fun conversation. And I think I got some psychological work done here too, which has been very helpful. so i'm very happy i'm very happy all right i'll talk to you soon i'm sure okay bye