Mike Pollack: My Post-Exit Identity: Student of Life

27:49And so I think once we set up the business, our vision got bigger about all the things we could do with our technology and with our business. And I think we had a great exit and a great outcome come along at a unique moment in time right before the market got kind of crazy. And I think we left room for plenty more things to do. And I think great businesses never finish the task at hand because there's so much opportunity there. And so, you know, I think my co-founder and I independently set out to solve effectively the same problem, but from two different spheres. I think he approached it from a technically, how do you solve this with technology?

28:32I was focused on how do we build a business around making this a thing and making it a self-fulfilling prophecy that everybody would use this. And so I think in that regard, we got lucky, my co-founder and I, that we had similar views on the matter. We had similar values and similar philosophies. And then again, we both saw a similar problem from two different lenses. And so we'd go to a customer meeting and he'd hear something and I'd hear something and we'd hear different things. but they arrived at a similar conclusion. And so I think in that way, we were really lucky. And I think that made it a much more impactful thing.

29:11But yes, to answer your question directly, I think the passion hasn't changed. And I think if you're a lifelong student of a specific problem space, or you're trying to be an expert in something, it's so alluring to go chase something else. Again, you see this conundrum with post-exit founders. You and I are jointly in a group with a number of them. And something you see all the time is somebody starts a business about bananas and they become an expert on bananas. And then afterwards, they're like, oh, I can't ever work on bananas again. I need to go work on watermelons. But they forget how much they know about bananas and they forget how steep the learning curve is to figure out watermelons.

29:54And so, you know, the way I characterize this to many post-exit founders that I talk to is, you know, you should be smart enough in your problem space potentially and dumb enough to try it again and not underestimate the cost of switching. Other ideas seem so alluring and so compelling. And again, this is where our brain tricks us about grass is greener. I've found that I think it's in my I think I can have a bigger impact if I stick to a problem, even if there's some initial pushback of like, but this idea over there is so cool. That sounds so neat. You forget how much expertise you have and how hard and how long it took you to acquire it.

30:35Again, earlier in this interview, you used the word trauma, which again, is probably fair in some ways of being in a space when you don't know anything in the beginning and then begrudgingly learning lessons the hard way one step at a time. And the cumulative weight of that is probably fair to use the trauma word to say, hey, you climbed a mountain one step at a time. And in the real time, you may not have even recognized how many steps you were taking, but the cumulative step volume is enormous. And so I think the best thing I encourage many founders to do is stick to the space where you're most impactful.

31:09Again, and there's obviously amazing founders who can cut across spaces and people who are just exceptional in that way, I've come to the realization I might not be one of them. And I'm cool with that. And I'm okay to stick to my lane and play in a space where I can have the most impact. Yeah, this issue comes up a lot in my interviews as well. And there is a different school of thought, which basically suggests that it's perfectly fine to switch to another space. And I noticed that it usually comes from people whose zone of genius is industry agnostic in a way, that they have some particular talent that can be applied across different industries, then it's fine.

31:49So I imagine that if your zone of genius is in sales, your network that you've built is enormously valuable. And it would be, from your perspective, very silly to not use it, right? And maybe that's why you feel so strongly about that. Am I wrong? You know, so you say zone of genius for myself, I might frame it as zone of competence. I don't know if I'd go as far as to give myself any room for genius at all. But I think, you know, I think my expertise is generally around human behavior. And I think sales and marketing and in a business context is fairly straightforward and bounded. You know, I think about entrepreneurs who operate in the consumer space.

32:36And something that's so peculiar to me is I'm a consumer and I behave in wildly unpredictable, strange ways. I'm probably my own difficult consumer. But I think about the evolution of consumer products and all the things a consumer can do in a business context, coming from like a management consulting background. it's pretty straightforward what most businesses need to do. And sales and marketing, if you think about what they're tasked with doing, it's grow revenue, grow opportunities. So again, you've bounded the problem and you've bounded the things you can do to attack the problem. And so in that way, I think there's a lower level of risk in creating in that space.

33:15That means the outcomes potentially are smaller. That means the failure is also, So the downside is potentially smaller too. To your comment about the zone of genius and thinking about entrepreneurs who are world-class, who can do amazing things. I'm not convinced I'm one of those. I'm pretty confident I'm probably not. And so what I'm comfortable with is saying, where's a place where I can make an impact, where I can make something just a little bit better and I can make my customers happier. I can generate revenue from that. I can create a team and get a great outcome for my team. I can get a great outcome for investors.

33:47And I think if I can do that, I'm very pleased to do that. And I think that's an awesome way to do it. But to your point, I do think, again, some problems truly are horizontal. And again, take like a world-class entrepreneur, like an Elon Musk or somebody like that, who can apparently work across multiple industries. It's very clear. He has an amazing understanding of the physical world, right? When it comes to things like rockets and manufacturing, this person is amazingly, incredibly talented at understanding that and challenging those around her to push through some of the common problems you might see there.

34:23Now, it will be interesting 20 or 30 years from now if that same genius applies to fickle consumers like a product like X or Twitter. I think that'll be so interesting. And I think for entrepreneurs, if you believe, and again, if you believe the mechanics of your expertise can be applied horizontally, then I do understand that. I do understand how you could say, hey, I'm going from space A to space B. But, you know, when I meet founders who had a business in, again, sales or Martech, and then they say, hey, I'm going to go into the healthcare space. I think, again, people underestimate the complexity of either understanding a regulatory environment or understanding the players.

35:07I think your comment about a network is very valuable, a network of people who will give you honest feedback about your idea, your product, or whatever. One challenge I see, particularly when you start a business, is humans, I think, want to be conflict-averse and want to be kind to one another, naturally. So when you start a new business and you ask people and you say, hey, I've got this idea, people are always like, oh, yeah, that's a good idea. That's great. And I think that is a borderline dishonest thing that people do, not in a malicious capacity, but just because it's easy to do that. I think part of your job as a founder is to figure out how to disprove that nonsense.

35:49And in my world, I've learned it's get money because businesses don't give money just because they give businesses because a problem gets solved. I think when you start in a new space, a lot of people will be like, oh, this is such a great idea. But it takes a long time to convert the, hey, this is a great idea to, okay, sure, write a check or commit. And I think naturally, if you're a founder, chances are you're an optimistic human. You believe that people are being honest and genuine and they are excited about what you're up to because you're an excitable human. I think that part is very hard.

36:22So I think for me and what I encourage other founders is where are places where you can de-risk that it's awesome to it's a real business and shrink that space? And again, to your point, there are founders whose zone of genius is so broad, they can do that from space A to space B. I just don't think I'm one of them. So I don't know exactly how they do it. Again, I operate in my zone of competence. Maybe someday I'll get to some kind of like, I don't know if there's ever going to be like a small lowercase g genius associated with it, but I'm happy to stick to my lane and do what I can do inside of there.

36:56I saw beautiful how much clarity and rationality you have in your decision. I don't come across it very often. Again, as I said in the beginning, you're unique in many different ways, including that. Can we dig a little bit deeper in how you see success in this stage in your life? I would say for me, the way I see success is I wake up with a limited amount of stress because some of that is self-manufactured. And I go to sleep with as little stress as humanly possible. And to expand on that a little bit more, it's I'm surrounded by people I care about and I love. So two layers of that. The first is my family, and I hope that they're all healthy and happy and taken care of.

37:44The second layer is my team. And again, a team is my co-founder and the team we're building, but it's that I care about these people and they challenge me and I challenge them to do their best possible work. I think if you get those things, that's an amazing setup. And then beyond that, there's some level of economic, I don't know, satiation I think you need to have around your needs are met. it's interesting when I talk to other exited founders from millionaires to billionaires, a thing that I find so interesting is this cohort, which from the outside looking in, looks so happy and looks like they have everything, oftentimes is as unhappy, if not more happy, unhappy than the general population.

38:32And I think, you know, you have to define your own success. You have to define your own happiness. I think we live in a culture, particularly the US culture, and I think social media amplifies this, of you never have enough. This other family, this other company is raising more money than you. They're going on nicer vacations than you. You're missing out. Success to me is block out all that noise and be happy with what you got and accept that. That's easy to say and hard to do. There's moments where I see founders raising some amount of money. And I'm like, wow, that's crazy. That should have been me.

39:10But so what? Who cares? Let it go. And I think it's okay to have those fleeting moments of like, wow, wouldn't that be cool? But I also don't let those capture my psyche. I don't let those hold me hostage. I don't let those do that. So I try and, you know, daydream globally at times, but perhaps really live locally in that I'm very happy with what I have. And I think I have to focus on making the most from the most of what I have. And again, if in my head I decided, hey, I need to take this business to this stage or I need to structure this in this way, perhaps that would be part of my success criteria.

39:50But I've just found let a lot of that go. I think the younger version of myself was much more active about status. status i need to get to this level i i want to be the ceo of this i want to do this i i think just the benefit of maturity in life and experience is recognizing that's all noise and if it doesn't matter to you then it doesn't matter and and again so much of social media is filling you with you need this or you should have this it's not explicitly said that way but but when you scroll through the pictures and you see somebody on there whatever doing their whatever an emotion you could feel is how I should be there.

40:31Why didn't I get invited? Or why don't I have that? And I think success to me is, I don't give a shit. And I have freedom intellectually around that's not holding me hostage. And I truly enjoy where I am, who I'm with, what I'm doing. And I do it because I have the flexibility to do so, which is a privilege. And I don't have the prison of, I have to do it because I need to. I think the opposite of success is you're in a situation where you don't have control and that makes you feel frustrated and worked up. And I think the simplest way to think about success is you have intellectual independence from the things that could hold you hostage.

41:16That doesn't mean you're rich. That doesn't mean you have to be. It just means you have control over where you want to be and what you're doing. And I think that's much more of a mindset potentially than a physical outcome. The two can go hand in hand. But again, I know plenty of people who are from the outside very well off or have enormous money or have big houses, but are in their own head a failure or not successful. And I think that's just such a crushing, heartbreaking way to exist. And I think the only person that can change that generally is you. I absolutely agree. so when you were building your last business you did not have children I mean you got your first one towards the end of that journey so now that you're thinking of starting a new one you have to face the need to balance and share your love your dedication, your time, your energy with your children tell me how you are feeling about it and are you tempted to and not start the business quite yet while the children are so small.

42:25So as we're recording this, when you say start a new one, it's funny you say that we have a baby due next month. So when you say start a new one and I'm starting a company, in many ways, it's like where I'm living both. And it's interesting, when we were selling our business, us. We started our M &A conversation started in October, and then the business was sold in March, so maybe about five, six months. And I had a daughter in November, so like a month into the M &A negotiations. I had a baby, and I took, I don't know, maybe two weeks off, and then we kind of went into it and did that. I think it's amazing how the brain works.

43:04I don't remember that being that bad. It was very hard. Again, the M &A is a challenging experience. It's hard. And then having a newborn is its own challenge. And my co-founder now has, at this time, maybe a seven or eight or nine month old. And he was asking me about, at the time when we were selling the business, at the time I had a two-year-old and a newborn at that moment, how did I do it? And again, the brain's such a crazy thing that I don't really remember. But we got it done. We got through it. And maybe, again, your comment about trauma, which I picked on a little bit, perhaps is accurate because my brain's totally hidden it.

43:43It was so bad, like my brain hit it, or it wasn't that bad at all. And I don't know. So that's one thing from the past. But you ask me, how do I think about it going forward? I'm foolish enough to think I can balance it all. And I say foolish because the data shows I can't and I will drop something, even though I'm at this moment arrogant enough to think I can do it. And so I think, again, going back to this student analogy, I'm trying to figure out how to do that. And I think, you know, me and my co-founder, when we talk about what we want to do next, we spent far more time this time talking about how would we want to structure our business and our time to maximize the outcome of the business and the outcome for ourselves the goal isn't to work to death to your question about when i had no kids it was easy to work 50 or 60 hours it was easy to work all the time right when my wife would go to sleep i'd sit do more emails i just emails this poison that is this never-ending thing where you could always just respond to one more person or just write up one more thing.

44:49And I, like many people, totally am guilty of getting on the treadmill of like, oh, yeah, I'll just hammer out email after email after email. And again, in hindsight, did that even matter? Did I even need to do those? And so I think the thing I'm trying to think about having a family and going forward with this is, and again, maybe this may sound ridiculous, but how do you do this in a healthy way where you balance both? And I I think there's people who can do it. I look at someone like Sheryl Sandberg who tells an amazing story about being a mom and making this work and building one of the biggest businesses in history.

45:24And, you know, I don't think I'm even at her. I'm not even close to her level. I know that she's got real zone of genius. Again, zone of competency on a good day. So I think it's doable. And I think one of the benefits I get of being the founder and the CEO is I do get to architect it in a way to try and maximize both. You're right to call out. There probably is a cost and one that I can't see and don't fully understand at this point. But I think it's worth a try. And I think, you know, should I find that it's not sustainable or it doesn't work? One of the privileges I have now that I didn't have five years ago is I could say, okay, you know what?

46:03I need more help. We need a COO or I need a chief of staff or I need to delegate more effectively or I need to allocate this somewhere else or you know I need to focus my time elsewhere and I think that's where the difference in being well you need a nanny oh yeah nanny yeah exactly right yeah all the resources right yeah exactly right a nanny all the resources right and that's where I think that's that's where I think you try to figure out what are you optimizing for and and again you know at the start of this conversation we were talking about identity right and if your identity is, I'm the CEO, I need to carry the business on my shoulders, then it's going to come at a cost to your family, right?

46:47And I don't view myself as I need to, and again, I'm not operating a fortune 25 public company, right? In the beginning, I think a lot of the work is, a lot of the work I did when I look back at things I was doing, my co-founder and I had a great conversation just a couple of months ago, we were talking about, we probably really only needed to do 30 or 40 percent of the things we actually did, but we needed to do them 60 or 70 percent harder. And you just think about that idea of, again, I was always busy as in the earliest days or even in our business. I was selling, I was writing spec, I was doing whatever.

47:26And again, if I'm really honest about it, was any of it really that good? Was I doing my best work? If I just said, hey, instead of doing 10 things crappily, let's just do one or two things amazingly. And again, when you start in the beginning, you have no choice because you're like, if I don't do it, who will? And one of the benefits we have now of starting this business and with more resources, you can say, what are we optimizing for? Myself and my co-founder, both of whom now, again, are parents of young children. It isn't, we have to make this work at all costs. It's we want to build something that has an impact and is good and is amazing and adds value for customers, but not necessarily at a cost to our sanity.

48:09And so I'd say right now in the benefit of I'm in the earliest stages, it's easy to say how we're going to figure it all out. We'll figure it all out. It'll be easy to your point. It's a nanny. It's a chief of staff. It's a wherever you need more support. And I think the biggest difference, at least for me, about being an experienced person versus being an inexperienced person is when I was inexperienced in my life, I didn't know how to ask for help or I was too afraid to ask for help. As an experienced person, I desperately ask for help all the time, everywhere I possibly can, and I have no shame in doing so.

48:45And so I think that's the biggest difference. And again, I think having the confidence and again, about your identity, you don't have to do it all yourself. I think so much of the marketing to founders is like this, like hustle porn of you got to work harder, you got to do it all yourself, you got to carry all the water. And for some founders, and for some businesses, that might be true. But that also potentially begs a bigger question of should that business even exist? Are you even chasing something that makes sense? Right? And I think that creates a lot of corrosiveness inside for many founders and the founder community broadly.

49:22And I think the reason I tend to stay in a space where the problem is validated, the customers are reasonable, the market conditions are straightforward. I am truly minimizing my upside, but I also believe I'm minimizing my downside. And so I think I can have a higher probability of success and I can balance some of these things. But the question you're asking is a fair one. And at this moment in time, I think it'll be great. But you're totally right to call out like, maybe I'm underestimating it, which I probably am, which I tend to do. So I don't know. Check back in in six to 12 months, and I'll give you a more cogent, real answer on this one.

50:01So talking about money, how does your relationship with money and then the meaning of wealth change for you after you sold your business? So before I sold the business, I had moved to San Francisco now almost 10 years ago. And when I came here, I had a duffel bag, like a bag of stuff. And I stayed in somebody's rent controlled bedroom. I had no money. And I was in debt because I'd started a thing with a friend and it was its own catastrophic disaster. her. And in my time being here, I saw extreme wealth all around me and none of it was mine. I didn't have any of it. I didn't have access to it.

50:43I'd go out to dinners with people. And in the Bay Area, particularly from the years 2014 to 2024, that period of time, there was extreme wealth being made and venture capital was funding all these things. And so in many respects, I was the benefit of being in some of those communities. But again, I was just as concerned, like, how are we ever going to be able to live here? How can we ever have a house? How can we ever, I'm living in a rent controlled place. I mean, that helped sustain me for many years. And so when we sold the business and our economics changed radically, you know, I think our relationship with means and wealth changed as well.

51:23We were able to buy a house and we were able to set up our family in such a way that we think we're going to be okay and we can make it work. And I think, you know, wealth is a double-edged sword for many people. I talk with many founders who struggle with it, and it's an albatross of sorts of like, what do I do with this? It carries a big burden on me. I don't necessarily feel that. I think, you know, wealth is in many ways, like any other kind of vehicle, it can get you to where you want to go. If you don't know where you want to go, or you drive it recklessly, it's going to get you in trouble.

52:01And I think, you know, we, my wife and I have a really reasonable mindset where I'd say Midwesterners and like the true sense of that. And that I think what we want is reasonable and what we want for our family is reasonable. I don't think our ambitions or our aims are ostentatious or gross in that way. And so, you know, I'd say I, we choose to manage our money the same way we did when we had very little in that we try to be thoughtful with it. We try to support causes we believe in. We try to spend it on things that will make us happier or add value. But I think, again, it's a strange thing how wealth is portrayed, particularly in America, right?

52:44That the story in our culture a little bit is the American dream is about wealth and money and acquiring stuff and getting more. And again, this envy of we have to go after these people that have it. And again, the thing that I think most people don't fully recognize is many people who have money, again, are as unhappy or if not unhappier than people that don't. And so for us, I think it hasn't dramatically changed our worldview. I think it's given us flexibility. And I think that the best way, again, another analogy for wealth that I think about is, again, like the vehicle, it gives you optionality.

53:25It gives you optionality to say, oh my God, I have to take a job doing something I don't want to do because I need to pay the mortgage. Or it gives you the flexibility to say, you know what, I'm going to take six to nine months to think about this thing and mull it over. And so I think it's an incredible tool and just that. But I think, again, the way it gets played in our culture and our society is used to divide and used to maybe make people scared or do all kinds of strange things that, again, is peculiar to me. I don't know. I wasn't raised in a way where we had ostentatious wealth. And I think when I look at people who've accumulated large sums of money and I just see them struggling with that, I think that's such a strange thing.

54:14And I think many people from the outside looking in don't understand that or don't see it that way. Because again, so much of the American dream is you're going to win the lottery or you're going to have all this money or it's going to be so great. And it just, it doesn't work like that. It's not like all of a sudden you close the deal. You ask about wealth, right? Like a tangible thing is, you know, there was always a moment when I'd be fundraising where you're going out, you're asking for the money, you're trying to do it. And it's, it's a, it's a hard thing because many people are telling you no.

54:43And then there'd be this day where somebody would say yes and you'd get the money and the wire would come through and you'd see, you know, millions of dollars hit the business bank account. And for a second, I'd be like, oh my God, this is so exciting. Look at what used to be like zeros and zeros and zeros. And now there's a number in front of those zeros. And that was such an amazing thing. But it did like fill me with joy. It actually filled me with anxiety of like, oh my God, now I got to not screw it up because someone's entrusted me with all this money. I think the same is true when you accumulate wealth.

55:14The difference is you don't have investors, you have a family, and potentially you have multi-generational people if you're thinking about that or trusts you have to set up or now lawyers you've got to deal with. And so in that way, the problem just gets bigger. And again, you talk to people who have far more money than we have or billionaires or whatever, and they have their own challenges they contend with, with the albatross that is wealth. And so I guess that was a long-winded way of me processing it in my own head, because I guess I haven't thought about it a whole lot, But the short answer would be for us, I'd like to think it enabled me and my family to have more flexibility and optionality.

55:52But I'd love to believe it hasn't changed our values. It hasn't changed who we are and what we want to do. And it's simply given us flexibility to get to where we always wanted to get to, but perhaps take a little bit more time to get there or see some things along the way. And so in that way, it's been a wonderful thing. Do you ever feel guilty about your financial success? I don't feel a lot of guilt. Generally speaking, I'd say the most guilt I feel is as a person who talks a lot. Sometimes I say something I shouldn't have said. That's where I'd say I feel more guilt. I'd say on an economic basis, no, I'm incredibly proud of the business we built.

56:30I'm happy to hear from the customers who say things like, you helped me get my bonus or because of the thing you built, we closed more business. I'm very pleased to be in what I would perceive as an honest business. I don't sell tobacco. I don't sell credit cards. I don't believe I prey on people. And so I think, you know, I know people and founders and people who are in businesses that I wouldn't choose to be in. That doesn't mean they're right or wrong, but that would be one thing. And I would imagine if I had made money in that way, perhaps I'd feel more guilt. But no, I think we built something that was valuable and the market rewarded us.

57:07And it's interesting, the business we built, values of businesses go up and down. And at the particular moment we sold it, the value of the business was very high. If we sold it at this moment, it would be lower broadly across the software space. That's what's happened. In the future, that will probably go back up again. And so, no, I view it as we played a good hand in that the goal of the business fundamentally is to get an outcome. I'd say for your customers, your employees and your investors in that order. And I'm pleased to say we got outcomes for all three of them. And that's awesome. And so I think where there's an opportunity to feel guilt potentially is, are you using your means to accomplish your goals, whatever those are, whether that's supporting the causes you believe in, whether that's empowering your family and your friends and those around you?

58:00I think that's where people can self-manufacture some guilt. And I feel pretty good that we're trying to use our means, again, to empower those around us, to support the causes we believe in, to, again, give our family the best chance and ideally leave the little part of our world a little better than we found it. And so I feel no guilt about that. And I think, again, you have to, part of the responsibility, I think, is when you acquire something or accumulate something, Your job is to be a steward of that and to leave things better than you found them. So I feel very good that we're trying to use our means, again, to leave things better than we started with them.

58:42And if I felt that we weren't doing that or we were being a bad steward, perhaps that's where guilt comes for some people. But for me, my motivation would be, so then fix it. Don't feel guilt. Just change it in the same way that if I feel guilty, I said something I shouldn't have. the thing I would do is go and apologize and say, I was an idiot. I put my foot in my own mouth. That was my bad. And so I think, again, guilt to me a lot of times is you know you did something wrong and you're not fixing it or you haven't fixed it or you're not trying to fix it. And I just, as a self-motivated human, believe, go fix it.

59:17If you're feeling guilt, go fix it. What are you waiting for? And so the answer to your question is no, absolutely not. What are the most important values for you? I'd say the most important values for me are first, probably being true to yourself. So the question about guilt, right? If you did something wrong and you know you did something wrong and you let it fester, to me, that's where you eat yourself, your insides kind of eat you up. And I think being authentic to who you are is a key value and trying to be the best version of yourself. I think that's a big one for me. The second one would be always try to leave things better than you found them.

59:58That means interactions with humans. That means when you do something with your family, that means when you create a business, my intentionality is to try and take things that are good and make them better, or if they're bad, make them good. And so I think that's a core one. And then I think the third one that also comes to mind is just be good, just be a good human and encourage those around you to be the best humans they can be. And I think about that as a parent, when you try and teach a lesson, and sometimes when you're in the moment and you're like, oh, I'm so frustrated at you, how could you do this?

1:00:31And then you realize you're being a jerk, or you could do a better job, or, you know, I'm not going to argue with a four-year-old, because what does he know? And so I think that's an important one. And you feel that as a parent, and I think I feel that now as a founder, when in our last company, where, again, I was so busy responding to customers or chasing stuff down, I didn't take the time to really document our values thoroughly or really articulate why we're doing what we're doing or why it's so important. I think, you know, it's, I now have the, again, the privilege, the time to do that and the time to think about that with the next one.

1:01:06So I think, again, being kind, doing good, I think that's a big one. And then, you know, maybe just last, or maybe it's the corollary to be good is just, again, then try and pay it forward any way you possibly can. I think about as an entrepreneur, I'd like the Thomas Edison adage of his idea of failing his way to success. I think we talked about zone of genius earlier. I think about zone of failure translates into zone of not failure anymore. And then maybe you get up to confidence and then maybe, maybe genius someday. But I think this idea that I want to use my means, my time, my wealth, my resources, my attention to help make everywhere I can just a little bit better and a little bit more impactful seems like a good way to go about it.

1:01:58I don't know if that's the cure-all, end-all, be-all, but again, if you take that as a northern most star, it seems like a reasonable one. And so maybe that's a corollary to the third point, but that would be broadly how I would probably think about it. Is spirituality part of how you perceive the world? What are your thoughts on that? So I'm a spiritual person in that I fundamentally believe there is something bigger than all of us. As a person who is not the best with authority, I have some challenges with religion as a construct. But again, I believe fundamentally in spirituality. And I've experienced and seen things that are just bigger than me, bigger than humans, bigger.

1:02:48When you go to spaces and the earth and you see whether it's the Grand Canyon or things of enormous impact, you're like, wow, this is so cool. And when you see a team, like a high-functioning team, whether it's as actors or a company or whatever, make something that transcends what that team can make individually, you cannot not give credit to spirituality and to just say that there is something bigger and greater than all of us. I just, I'm too pragmatic of a human to not give credit where credit's due. I think a lot of people ascribe their success to things that are greater than them, which I think is self-undermining in some ways.

1:03:32And so I think everyone's got to choose their own, I don't know, your own deities or your own whatever about where you get the motivation to do what you do. But I think it's very hard to go through life and not say, wow, I got really lucky on this and ascribe that luck somewhere, whether it's a dice roll in the universe, whether it was just the gods aligned. I don't know what it is, but I think you have to be spiritual because to believe that this whole world can just be explained by a bunch of silly humans, just it doesn't give enough credit to all the crazy things that happen in the world. So yes, I'd say I'm impressed and awed by the the spirits that exist broadly and the spirituality that collectively comes out of that.

1:04:18But again, my cynicism with just dogma and rules and top down of it has to be this way, I don't love that. And again, the reason I find, again, spirituality, broadly speaking, interesting is it demonstrates there's no right way to do it. And if you look at the evolution of religion or spiritualism over time, all these ideas, they're wildly different, but they all kind of collectively overlap in some very similar ways. And so I think there is a role for that. I think, you know, whether you ascribe it to spirituality or luck, you have to recognize that there are things that play in the universe that are bigger than you that you can't control.

1:04:57And if you're content to allow that to happen and you let go, they're awesome and amazing things can happen. And, you know, sometimes you get really lucky and then sometimes you get to crap roll the dice, but you just got to keep playing the game. And I think that's an exciting part of being in resistance in the first place. If someone sold the business yesterday and came to you for advice about how to handle this couple of years right after, what would your advice be? So usually I have a good or a bad habit, depending on how you want to frame it. But when people ask me a question, usually I tend to follow up with a lot of questions just to make sure I know what's going on.

1:05:36And so the first question I might ask in that situation is, why did you sell it in the first place? Because I think a lot of times people's motivations are there, but either they don't want to see them or they're hard to unpack. If you said, hey, like I was burned out, like I again, and broadly speaking, you know, I think there's only a couple of reasons someone sells a business, right? Right. You're you're burned out or there's an economic incentive to do so or the team's tired or you see a better opportunity or you want to move on. And so I think the first question is, why did you do it? And I think that alone will unpack a lot of conversation about how you got there.

1:06:17And then the next question is after that. So where do you want to go next? And I think the natural state is always why I want to keep doing what I was doing, because that's what I know. And again, we talked earlier about identity, right? And if your identity is wrapped up in why I was doing this, I don't even know who I am now. That seems terrifying or is fucking awesome, depending on how you frame it, right? The scariest canvas you ever look at is the blank one. It's so easy when there's stuff on the canvas to be like, oh, yeah, I've changed this or I'm happy to be an editor. It's real hard to be a creator.

1:06:55And so I think, you know, the blank canvas problem is real for anyone, anywhere who's making anything, whether that's an entrepreneur pursuing their next idea, even trying to define or design their identity. I think that's a real thing. But I think the first question starts with, why did you do it? And again, I would imagine, because I've had this conversation with other founders, when you ask that question, there's four or five layers to really unpack even that question. Because again, there's the surface level of maybe what you told your investors. Or maybe what you told the team. But then there's the, what were you really thinking when you were laying in bed at night?

1:07:31And again, was it a trauma-driven decision of like, I need to get rid of this thing. I can't do it anymore. Or was it like opportunistic of like, this buyer came along and offered me so much money, my eyeballs exploded in my head. I couldn't believe it. Again, I think once you go there, people don't give enough credit, I think, to their own internal monologue and are quick to discount it and say, well, they just came along and offered me this money. But if you believed it was bigger, you would have stayed. Or if you knew it was done, you would have left or whatever that is. So I think the first question is, why now?

1:08:10Why did you do that? And I think there's a very rich vein of conversation in there. And then when you peel that back, before I even would take the founder looking forward, what do you want to do next? I'd spend a lot of time talking about, well, what did you love while you were doing, when you were doing it? What was your favorite part? And again, in my brain, when I think about the seven years now, they all kind of blend together. I'm a good self-liar in my own head of like, oh, it's all great. We had all kinds of good times. But if I really think back on some of the times where it was like really terrifying, or something bad happened, or we lost a key customer, or a major account fell through, there's those moments where it was terror it was horrific in the in that moment right obviously we're fine in the end um so i i think i'd spend a lot of time doing that and i think most founders what what makes them unique is they're really good at looking forward they tend to be awful at being introspective because it's dark and scary and hard and there's no good answers and that's why you know most founders probably don't need a coach they need a psychiatrist and they need to actually deal with their inner monologue of what they're doing in the first place but that's hard and that's dark and that's scary and most people don't want to do that so so i i think i'd spend more time talking about what what did you do before we even get to where do you want to go and my goal in doing that if i could get it right i don't know if i could would be I don't give any advice about where to go.

1:09:50If you ask the right questions, the founder says out loud what they want to do and they make the decision. And it's my job to just help them say it out loud and have the confidence behind it because the answer they already know. But again, it's easy not to go there. Yeah. Sometimes they know the answer. Sometimes they have to face the reality that they have to go and fight those demons and do the work of introspection. But what I see happening a lot is just people do what they think other people expect them to do or just what people around them do, which is why we see so many tech entrepreneurs going into angel investing of VC, right?

1:10:32Because they think, oh, that's the path that people around me seem to be doing. But then you go to different parts of the world and they don't think that way. So it's very clear that people think that way, not because they did all the work they need to do, but just because of whom they're surrounded by. You know, you make an interesting point. Like I'm originally from the suburbs of Chicago. And one thing that I love about the city of Chicago is we have world class cultural institutions. We have amazing museums, great, spectacular museums. And one thing that happened in the late 19th century is as entrepreneurs would make money, they would endow their cultural institutions.

1:11:13They'd become large philanthropists and support these organizations. In the Bay Area, I'd say our cultural institutions, our museums, our art galleries, they're okay. They're not nearly as world-class as I think they should be. And I would agree with your point, which is a lot of people make money and then they don't know what to do with it. So they're like, oh, I'll just invest in more startups. Again, zone of genius, zone of competence, maybe zone of insecurity because they're like, oh, well, I know something about startups, but I don't know anything about art. I don't know anything about how to structure a museum.

1:11:45And I think, you know, the tech ecosystem is unfortunately very insular and at times very narrow banded in that you have people who say, oh, I know a lot about technology, but I don't know anything about anything else. So I'll just stick to what I know rather than go do the hard thing of saying, wait, I want to go become a world class philanthropist. Or again, look at what Bill Gates has done in terms of being an amazingly interested human of saying, wow, I'm going to go achieve mastery on all these topics that have enormous implications for humans. What a wonderful thing. And that's not the end all be all, but that's one approach to go be like, again, if you're a SaaS founder and then you're like, oh, I'm going to go be an angel investor in the SaaS space.

1:12:29Like, sure, maybe that brings you joy. But I realized really quickly, I'm not a very good investor. I don't get joy from that. That's not exciting to me. And I have the confidence to say out loud, I don't think I'm going to do that. And even though there's many people who like that and love that and maybe are great at that, those people should do that. But there's also a whole cohort of humans who are doing that just because they don't know what else to do. And I think you raise a very good point, which is it's so easy just to go with the flow. It's so hard to raise your hand and say, no, no, no, no, no.

1:13:00I'm going to do something a little different. and again our society is optimized around doing what you already know how to do and people not questioning you or challenging you and again if you're not prepared to do the hard work introspectively of like wait wait do I really even care about this problem or more importantly do I care what other people think about me if I do something different do I have the confidence in my self-identity to do that I think many people struggle with that and particularly in a founder set, imagining just among engineers or people who are less extroverted or maybe don't have as much self-confidence or their identity has been forged around this tech universe, it's been very hard to break out of that.

1:13:45And so, you know, I see and know many people who have that problem. And I think the Bay Area has an incredibly large collection of those humans, even though now post-COVID that's scattered a little bit. It is a peculiar thing. And I think again, for many founders, it looks like they're so successful, but on the inside, they feel like they're shackled and they're stuck in this space, excuse me, or this identity that they didn't entirely choose, but that's all they know. And stepping out of that lane is so scary. And I think that's hard. I think that holds a lot of people back. Yeah. No, absolutely.

1:14:23And there is a balance between your zone of competence, as you call it, with a lot of humility, not zone of genius. And, you know, actually seeing that the world is more than what you've done so far or what you've experienced so far. Which is why I always love it when people take a little bit of time after they exit and maybe travel or experience something else or at least do a lot of thinking and introspecting before they commit to another 10 or 20 years of a particular activity. I think that's a fair point. And I add to that, that, you know, there's something that's peculiar about the tech space that I've encountered is, you know, many founders or people who get into technology.

1:15:13I'm going to broadly generalize, it may not be entirely true, but I feel like many founders view technology as a way to remove humans from a process or some point in their life experienced, I don't know, maybe trauma from other humans and always thought that, wow, the technology will get humans out of it. of here. And humans can be jerks. And we don't like humans, and we want to get rid of them. And sometimes you hear it in the Bay Area, this notion of like, well, people in the middle of the country, in the United States of America, they rely on religion. And they're such fools for doing so. But meanwhile, here in the Bay Area, you have this techno-utopianism of like, oh, but AI will solve it.

1:15:52AI will cure everything. And AI is just another form of that deity. And so what I think is a lot of people in tech view tech as a way to take humans out of the equation. And I think one of the strengths I have or the skill I have is I love humans. I think humans are awesome. And I think human nature is a fascinating thing. And I think I'm perpetually, to go back to the beginning of this interview, a student of what do humans do and how are humans successful? And I think if you make things for humans, you're always a student of how to make the best thing for humans. And so I tend to think my skill set means I can work with humans on many different kinds of problems.

1:16:31I've made a decision to stick to a problem where I'm somewhat of, again, a highly competent person. But again, I get excited going back to early in my career when I was a management consultant, I'm working on any kind of problem inside a business because usually there are problems of process, there are problems of people, there are problems of technology. And if you can just help humans come together, you can do these amazing things. And so I think, you know, many founders aren't as excited. There are plenty, but many tech founders in particular aren't as excited to really understand the human element of things.

1:17:04And instead, because their expertise might be on the technology, they're like, oh, we're just technology our way through this. We'll invent something, we'll figure it out. But in reality, most of the time, the problem is humans collaborating or humans working together. And so, you know, I think that's where the tech industry has this interesting challenge at times, because today technology is pervasive in every industry. There's no more just tech anymore. Everything is tech enabled. And increasingly, the problems are collaborative. How do you get humans to get the most from this? And so I think your point is there.

1:17:42And I think it's an interesting one many founders struggle with of like this inflection, I think, that's also happening in tech more broadly as tech disperses across industries, but also as some of the really cutting edge technology around AI and LLMs create a choice here around, well, do you take humans out of the process and rely on the technology or do you make humans more impactful? And are we tool builders or are we people replacers? And I don't think it's an or, it's not one or the other. But I think that's an interesting moment we're in right now. And I think for many founders, again, if you're tech-centric, you got a tech background, you're like, tech, tech, tech, I do what I know best.

1:18:21And I think that hides or masquerades where the problem really is and sends people down. Sometimes what could be rabbit holes. But I think you make a very good point there. Mike, I am enjoying this enormously and I can talk to you forever, but I also realize, you know, I need to let you go. So I have a couple more questions that are intentionally kind of black and white, but I want to challenge you. On a scale from zero to 10, how would you rate your level of fulfillment? fulfillment 10 being I have everything I've ever wanted ever and zero being I have nothing I have nothing I wanted whatever whatever you define it as say at this moment I'm probably a seven or an eight maybe in that I'm fulfilled and that I have an amazing family I've got a wonderful wife I've got amazing kids I have that working but we're not done yet we have a baby on the way and I have a four-year-old, a two-year-old and a soon-to-be baby.

1:19:29So like, it seems great, but we have things ahead and there's more to do. On the work side, we have this idea and the idea is so beautiful and elegant and great, but that's because no one's actually dealt with it. No one's giving us money for it. It's not a real thing. Ideas are always so beautiful in the beginning until they reach reality. And then you realize, oh my God, this is the worst idea ever. So I'd say the room for the two or three is, again, to continue to push myself to continue to be a student, to go further, to do more, to make my family happier, to build a business I'm proud of, to empower those around me and the causes I support.

1:20:05So I'd say I don't know how anybody could ever actually be a 10. And if you're all the way down at the other end of the scale, you probably need to do some internal work, maybe. So I don't know, six, seven, eight, maybe, on a good day. Brilliant. And my last question, how do you want to be remembered? Two answers. Number one, someone who told good jokes at the right moments in time, that that would be, that's like the silly part of me. But the second one would be, you know, somebody who fought for the causes he believed in, someone who helped those around him, and someone who, again, always left things a little better than he found them.

1:20:43And if I get, there was four things, but if I get like one or two out of the four, I'd say that's a victory. Mike, thank you so much. It was absolutely amazing. Of course. We have to stop, but I hope we'll continue in our live conversation soon. I look forward to it. Thank you for taking the time to chat today. I'm excited to continue the conversation and I wish you and the entire audience, I hope everyone stays safe and sound and sane in the world we're living in today. And I look forward to talking again soon. Thank you so much.