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

Written By Anastasia Koroleva

Episode - 25

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

 
 
 

Mike Pollack. He sold his third business 6 years ago and has since, through trial and error, crafted a unique formula that balances happiness with a high likelihood of continued business success. In this episode, he shares this formula with us, delving into how to identify your true zone of competence, release control, and master the art of letting go.

What We Discussed:

00:20:22: Discussion on Motivation and New Venture

00:20:53: Focus on Sales and Marketing Tools

00:22:10: Building the Business - The Science & Art of Sales and Marketing

00:23:14: Current Market Trends - AI and llms

00:24:46: Importance of Listening and Innovation in Entrepreneurship

00:25:33: Transition to Business Stories and Experiences

00:26:02: The Story of Their Sold Business

00:27:02: Evolution of a Business Vision

00:29:00: Entrepreneurs and Problem Spaces

00:30:01: Discussion on Switching Business Domains

00:31:05: The Concept of 'Zone of Genius'

00:31:53: Discussion on the Definition of Success

00:33:37: Balancing Ambition and Satisfaction

00:35:01: Ignoring External Noise and Staying Focused

00:38:21: The Importance of Being Satisfied with What You Have

00:40:33: The Freedom and Privilege of Intellectual Independence

00:41:16: Balancing Business and Personal Life

00:44:15: Work-Life Balance and Prioritizing

00:46:16: Identity and Work

 

00:47:28: Optimizing for Success in Business

00:49:45: Perspective on Wealth and its Impact on Life

00:55:28: Handling Financial Success and its Responsibilities

00:59:10: Emphasizing Core Personal Values

01:00:02: Fostering Goodness and Encouraging Others.

01:00:09: Teaching and Reflecting on Lessons

01:00:43: The Importance of Values

01:01:00: The Concept of Paying It Forward

01:01:55: Discussing Spirituality

01:03:50: Acknowledging Success and Luck

01:04:58: Post-Exit Business Advice

01:07:10: Motivations for Selling a Business

01:10:37: The Balance Between Competence and Exploration

01:12:37: The Role of Technology and Humans in Business

01:14:18: Re-Evaluating Tech-Centric Approaches

01:16:16: The Intersection of Human Impact and Technology

01:18:34: Level of Fulfillment

01:20:07: How do you want to be remembered?

01:20:35: Conclusion of interview

  • Mike Pollack: [00:00:00 - 00:00:13]

    There's only a couple reasons. Someone sells a business. 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? 


    Anastasia Koroleva: [00:00:13 - 00:00:35]

    Mike Pollock. He sold his third business six years ago and has since, through trial and error, crafted a unique formula that balances happiness with a high likelihood of continued business success. In this episode, he shares this formula with us, delving into how to identify your true zone of competence, release, control, and master the art of letting go. 


    Mike Pollack: [00:00:35 - 00:01:06]

    The human brain has a strange way of always thinking we can make our grass greener. When I talk to other exited founders, which from the outside looking in looks so happy and looks like they have everything, oftentimes is as unhappy, if not more unhappy, than the general population. Wealth is, 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. 


    Mike Pollack: [00:01:06 - 00:01:19]

    Most founders, 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. 


    Anastasia Koroleva: [00:01:26 - 00:01:28]

    Thank you so much for joining me today. 


    Mike Pollack: [00:01:28 - 00:01:28]

    Hello. 


    Anastasia Koroleva: [00:01:28 - 00:01:50]

    Good morning, Mike. You are a very unique person, and I'm very excited to have you here today. But one of many things that stand out about you is how you describe yourself on LinkedIn. Your LinkedIn profile says you're a student of life, and I love that. That's a perfect identity for a post exit founder. 


    Mike Pollack: [00:01:50 - 00:01:51]

    Thank you. 


    Anastasia Koroleva: [00:01:51 - 00:01:59]

    Can you tell me why you came up with this identity for yourself, or at least the identity you want the world to see? I'm not sure. You tell me. 


    Mike Pollack: [00:01:59 - 00:02:32]

    Sure. Well, thank you for reading that. I assume most people don't, because on LinkedIn, I imagine no one's paying attention anymore. But I think it's a strange thing to try and summarize who you are in a short, pithy overview. And I think on LinkedIn, where you're trying to present some little nugget of who you are, my reasoning for that is that's the most honest, authentic, and genuine characterization I think I can give of myself, in that I'm a student. 


    Mike Pollack: [00:02:32 - 00:02:48]

    I'm probably not the best student I'm trying, but there's plenty of room for improvement. And I like the idea that I'm continuously learning. I'll probably never be a master. But it's the pursuit of that mastery that I think makes it exciting. And that's the part of being a student that I enjoyed. 


    Mike Pollack: [00:02:48 - 00:03:18]

    And so, yeah, I think that setup accurately captures where I am, and I think it leaves room along the way to meet other students, many of whom are better or more successful than me, that I can learn from, meet and work with other teachers and masters along the way, and recognize that the journey of being a student, fundamentally, I don't think, has a destination. Obviously, there's points along the way, but I thought that setup was most, again, authentic and honest to where I am in my life and where I'm trying to go with it. 


    Anastasia Koroleva: [00:03:18 - 00:03:45]

    That's such a beautiful answer, Mike. I'm sure you know that lots of people struggle with their identity after they sell their business because we get very attached to our CEO founder identity and then try to find a new one. I definitely had that problem, and now, looking back, I think it was silly. But at that time, it didn't feel silly. It felt very painful not knowing who you are and how to introduce yourself. 


    Anastasia Koroleva: [00:03:45 - 00:03:52]

    Did you have that problem, or you transitioned into the wisdom of being a student of life easily and naturally? 


    Mike Pollack: [00:03:53 - 00:04:25]

    That's very generous of you to call it wisdom. I don't know if it'd necessarily be wisdom, but to go back to your comment, I think that the bigger challenge is many people struggle with their identity. Broadly speaking, founders have one set of challenges, but I think many people struggle in their own skin and struggle to define who they are and be happy with who they are. And so I think I take the question and break it into two pieces. Number one, how do you find or attain or figure out what happiness is with your own identity? 


    Mike Pollack: [00:04:25 - 00:04:45]

    And then secondarily, the question you asked about being a founder, what is your identity? I'm generally pretty happy with who I am. I've got lots of issues I still need to fix, and I haven't figured it out by any means, but I generally go up and go to bed and wake up and feel pretty happy with what I got. I have a beautiful, amazing family. I get the privilege to work with awesome people. 


    Mike Pollack: [00:04:45 - 00:05:17]

    I get to do cool stuff, and my life is filled with a lot of privilege in that way, fundamentally. And so from the standpoint of my identity, I'm flexible in knowing that in many instances, while I like to be a leader and a teammate, sometimes the best leadership I've ever done is following other people, taking a step back. And so, you know, I view my identity probably in a little bit more flexible construct, perhaps, than other people do. I don't need to be the CEO. I have been, and I enjoy that, and I get extreme pleasure from that. 


    Mike Pollack: [00:05:17 - 00:05:45]

    But at the same time, I've also learned being a teammate, sitting in the back, being somebody else's lieutenant or number two or number three is also just as critical. So to get to the second part of the question, thinking about how do, how have I found my post exit identity? Or how have I fit in there, I have to say, for me, it's been awesome. I have a young family with a four year old and a two year old and a baby on the way. And so there's plenty of stuff to do in my household and in my life. 


    Mike Pollack: [00:05:46 - 00:06:12]

    And I think being in charge or being the CEO carries a lot of stress. And much of that, perhaps, is self manufactured. If you let some of that go and you learn how to release it, I think you can find there's plenty of other things to do. And I do find joy in going to the grocery store and completing a grocery list. It's a different kind of joy, perhaps, than completing an m and a transaction or doing something like that. 


    Mike Pollack: [00:06:12 - 00:07:13]

    But I do think there's many little elements in life that need a task defined, that need a plan created, that need a job to be done. And my silly little reptile brain gets tickled when there's a task that needs to be defined, a plan that needs to be created, and even when that plan gets thrown away and I'm forced to create something on the fly, I get just as much fun from that, I think, as I did when I was in charge of the business or setting people up. So the short answer to your question is, I think having some stable mental health around your identity and recognizing it's not set in stone, it isn't defined in some book, and it can change and be flexible means that whether I'm a CEO or I'm changing diapers, my goal, again, to go back to that student of life thing, is how do I maintain my beginner mindset? How do I work with the team that's around me, and how do I get myself and those around me to perform their best? And if I do that and I do that every day, it's pretty awesome. 


    Mike Pollack: [00:07:13 - 00:07:24]

    I mean, that's cool. I like that. That fulfills what that little thing in my head that makes it feel like, hey, we got something done today. So I don't know, maybe that answers the question. Maybe that was too much. 


    Anastasia Koroleva: [00:07:24 - 00:07:32]

    That was fantastic. I loved it. Thank you so much. I didn't have to ask any questions. You just answered all of them before asked. 


    Anastasia Koroleva: [00:07:32 - 00:07:32]

    Perfect. 


    Mike Pollack: [00:07:32 - 00:07:35]

    Okay, good. Student of life, working on it. 


    Anastasia Koroleva: [00:07:35 - 00:08:06]

    That brings me to another thing we discussed already that I find very interesting about you, that you experienced at least two exits of businesses where you were not a founder before you started your own company and then exited it six years later. So how did it feel for you being quite a high level executive, but not the owner of the business during those exits, comparing to when you exited your own company? 


    Mike Pollack: [00:08:06 - 00:08:45]

    So, to belabor the student of life analogy, I think about a portion of my career, similar to many people, was learning from other folks. And when I entered startups, I entered startups first and foremost as a consultant, and then someone who transitioned into production, and then someone who went from a product position to a sales leadership position. And in those various roles, I was learning from wonderful people and seeing how other people did it. I think there's an enormous privilege in watching other people make mistakes and seeing how they make them and not making them yourself. I make lots of mistakes. 


    Mike Pollack: [00:08:45 - 00:09:07]

    I make them every day. I try and make less of them, and I try not to make the same ones twice, but generally speaking, I make a lot of them. You know, when you're joining a startup, you get the opportunity to enter into startups, as I did. I had the idea for something, and I met a team that had a better means to implement that idea. And so it was a great opportunity for me to join. 


    Mike Pollack: [00:09:08 - 00:09:40]

    And again, from a product standpoint, really design and create this thing that turned into a business, but ultimately was, you know, we raised a lot of capital and sold for substantially less than the capital we raised. By all intents and purposes, I would say economically speaking, it was a failure. But from a learning standpoint, it was phenomenal. I got to see all kinds of things, how not to screw it up, and life's easy, and business is easy to screw things up. So it was an amazing experience to see that. 


    Mike Pollack: [00:09:40 - 00:10:21]

    But you asked me how did I feel going back to the identity question, something that I think is consistent amongst founders or entrepreneurs is this idea about control and wanting control. If you're going to start a business, fundamentally, you have a viewpoint about control, that you think you can do it better. And I think when I look back on those experiences, one thing that created a lot of agitation for me that I don't think I handled very well was if I were in charge, I would do differently. And I think the human brain has a strange way of always thinking, we can make our grass greener. It's better if I were in charge or if I did this, I do this, I'm so much smarter. 


    Mike Pollack: [00:10:21 - 00:10:53]

    And the reality is, if I'm cynical about it, generally, grass everywhere in this analogy is brown grass. And you have to just accept the fact that your brown grass is like my brown grass and mine and yours, and who cares? Just have the grass you have and be happy with it. And so in those experiences, when I look at those businesses in hindsight, I think at times I let my perhaps emotions get the best of me of like, well, if I were in charge, I'd do this, and we should be doing that, and why didn't we do this? And who cares? 


    Mike Pollack: [00:10:53 - 00:11:46]

    Like, now that I've been the CEO, you know, and I've seen, I've been on the receiving end of that, I recognize how truly counterproductive that is. And there's times in a business, or when you're on a team, where you shut up and you just row in the direction the boat's going, the captain doesn't need to hear your feedback, and there's a time and a place for it. And so I think earlier in my career, where I had less self control and I was a bigger pain in the butt than I might even be today, I probably made those experiences more challenging, but I'd say emotionally it was tough, because, again, part of I think what makes me at times a good entrepreneur is I have a strong view about how things should go or where I want to take them. That view, again, may not always be right, but I believe there's some value in that. So when you're part of a team, you just have to shut up sometimes you have to package that. 


    Mike Pollack: [00:11:46 - 00:12:45]

    And I think that experience was at times challenging, but also incredibly constructive and value additive for me as an individual. And then you ask me, how does that translate into when I'm the CEO and I can think about, like, oh, God, I can empathize and completely understand what my team must be feeling right now because I felt it, and I was happy, excited, pissed off, frustrated, annoyed, all those emotions and more. And so I think that the best thing that can happen in life broadly is to experience things from other people's viewpoints. And so whether that's you being the employee before you're the founder or just being on the receiving end of a rough thing and then recognizing that it goes both ways, I think, again, it goes back to this idea that you're constantly learning. And so I think it was enormous gift that I got to work in some of these startups and again, make mistakes on other people's time and money. 


    Mike Pollack: [00:12:46 - 00:13:19]

    Watch and see how other people handle things. And in my head, I still carry that. I think some of the greatest lessons I've ever learned were watching how not to do it, because how to do it. We give ourselves a lot of credit for thinking that up, but a lot of times it's more valuable to see somebody, like, totally screw it up and say, like, oh, wow, I saw this from all sides, and I can understand how we got here and how not to get here. And so I'd say that the range of emotions is broad, but the learnings and the experiences are tremendous. 


    Mike Pollack: [00:13:19 - 00:13:32]

    And I think helped form me into, at times, a better, more empathetic, more understanding leader of just, hey, here's what the other side is probably feeling. So. So maybe take that under consideration. 


    Anastasia Koroleva: [00:13:33 - 00:13:45]

    Fantastic. Would you still say that despite all that experience, building your own company was traumatic experience for you? Psychologically traumatic. 


    Mike Pollack: [00:13:45 - 00:14:18]

    And trauma in the world we live in, I think carries a lot of weight, right? When I think about trauma, I think about enormous grief and pain and horrific things. And this is where I think our language, broadly speaking, in today's world, has gotten a little bit bombastic. And it may be overbuilt a little bit in that starting a company is very hard. You're right to use words like soul crushing and stomach churning and hard. 


    Mike Pollack: [00:14:18 - 00:14:55]

    It's incredibly hard, because most of the time, things aren't going right. In the six or seven years from when we started our business, when we sold our business, there were plenty of moments where key people left. Customers fired us, or we lost them, or we were near running out of money or all these things. And I think in the scheme of things, in the moment, traumatic probably is fair because your guts, it feels like, oh, my God, I'm going to fall off a cliff. When you zoom out and you take stock of the situation, you're like, hey, it's just a business I can let go. 


    Mike Pollack: [00:14:55 - 00:15:09]

    It's not life and death. It's not. And again, this gets back at your first question about identity and where you karmically carry the weight. If you view it as my identity, my soul is wrapped up in this business. The business dies, I die. 


    Mike Pollack: [00:15:09 - 00:15:28]

    Something like a karmic death. That's a heavy load. You're right, that's trauma. If you experience that, if you're a little bit looser on the grip and you recognize, okay, shit's going to happen, but the next day, I'm going to pick it up, I'm going to come up with a plan, and we'll figure out what to do. I think that makes it lighter. 


    Mike Pollack: [00:15:28 - 00:15:46]

    And here I have now the benefit of having sold the business now almost two years ago. So a lot of that trauma, perhaps, now has gone away. And like a parent getting ready for their next child, you forget about all the hard, brutal, crushing moments. You're just like, oh, sure, bliss. It's so great. 


    Mike Pollack: [00:15:46 - 00:16:09]

    So I could be lying to myself a little bit here, but I do think starting a business is a hard thing. Starting anything is a hard thing. Convincing humans to come along with you to do something, particularly if it's new or novel, is and always will be hard, because the natural inclination of humans is to say, no, I'm good. I don't want to take any risk. I'm pretty happy with how things are. 


    Mike Pollack: [00:16:09 - 00:16:24]

    And so when you're starting anything, you naturally will receive some pushback or challenge. And along the way, the hero's journey, as we know through history, is always, oh, I'm going. Everything's going great. Uh oh, something happened. Now I got to figure it out. 


    Mike Pollack: [00:16:24 - 00:16:41]

    And it's that up and down. And so, yes, I guess it's fair to say starting a business is very hard. I think this idea of trauma, I guess, depends on how you rank or think about or assess that hardness. Is it hard? Because intellectually it's draining. 


    Mike Pollack: [00:16:41 - 00:17:07]

    And at the end of the day, you got to solve all these problems, from employees that aren't happy, to customers that don't like it, to something broke, to the auditors found something. Who knows? Something's always coming up. And so I think if you perceive it as hard, it is more sustainable than if you perceive it as traumatic. And again, I know founders who would use that word and say, like, oh, my God, it was the hardest thing ever. 


    Mike Pollack: [00:17:07 - 00:17:33]

    And I guess that just comes down to how you view the world. I tend to think things are less hard than people sometimes may think they are. But that doesn't understate or negate anybody's viewpoint, because they're entitled to that, too. So I'd say, for me personally, it was very hard. We had moments where things were incredibly challenging, and we had days where, like, everything went wrong, and that's just so hard. 


    Mike Pollack: [00:17:34 - 00:18:11]

    But then I'd go to sleep and I'd wake up and I'd be like, okay, there is something to get excited about. Like, if I could just find that little glimmer of something that would give me the, like, the intellectual gasoline to keep going. And just the way I'm wired as a human is. As long as I can see just a little bit of progress, I can justify agony or unpleasantness or frustration. And so I'd say in our situation, and again, this may be with the benefit of hindsight, I want to think while there were moments, and again, I can vividly remember some of them where it was incredibly crushing and hard. 


    Mike Pollack: [00:18:11 - 00:18:49]

    I never thought, like, oh, my God, if I don't make this work, I'm dead, or, this is the end. Or, like, oh, no, I'm going to have to change my personality and name and become a whole new person. So I think people do have that experience. I think for me personally, it was definitely very hard, and we had moments of hardness, but I had enormous confidence in my co founder, who's a wonderful, amazing human, in my team, and again, in our customers, who, like, believed in us, gave a shit, and supported. So I don't know, maybe that's me with the benefit of hindsight, Molly coddling it a little bit and giving it rose colored glasses treatment. 


    Mike Pollack: [00:18:49 - 00:18:51]

    But. But that would probably be how I'd think about that. 


    Anastasia Koroleva: [00:18:51 - 00:18:52]

    Do you miss it? 


    Mike Pollack: [00:18:52 - 00:19:09]

    Yes and no. So, again, this goes back to the grass is always greener. I have something today right now that's wonderful. I have some free time before I start my next thing, and it's wonderful. But there are moments where I miss the pressure. 


    Mike Pollack: [00:19:09 - 00:19:39]

    I miss the, you got to figure it out. And I like that. I think I do some of my best work in that way, and I think I like the team I was surrounded with, who encouraged and challenged me to come up with bigger and better ideas than I could ever do on my own. What I miss the most is at this point, as we're starting to potentially bring together a new team and start working on what's next. I like when a team is together for a while, and like any high functioning team, people know how to challenge each other to do better. 


    Mike Pollack: [00:19:39 - 00:20:20]

    And I really get excited by the back and forth of, like, a good tennis match or something like that, where if you play with someone better than you, you play better. And the goal when setting up a company or a team, I selfishly believe, for me, is I want to play with better people than me so I can do my best playing. And so I miss that level of intellectual rigor right now, because the tasks I tend to work on are either more on my own, I need to figure this thing out, or I've been asked to look at this business or think about this thing, and I. I miss the whiteboarding time I miss the creative part of how do we collectively figure this out. It's not gone just at this moment. 


    Mike Pollack: [00:20:20 - 00:20:39]

    I'm not doing as much of that. And so it's like a muscle in your body that wants to work hard, but there's no, the task isn't quite there to work on. And so I don't believe it goes away. It's not a use it or lose it, but. But yes, in the short term, I'm excited to get back to that, but I also have confidence knowing it's not gone. 


    Mike Pollack: [00:20:39 - 00:20:43]

    And so it's not like a buy forever, it's more of a see, assume. 


    Anastasia Koroleva: [00:20:44 - 00:20:50]

    Okay, so what are you thinking? You mentioned you are putting together a team for a new venture. 


    Mike Pollack: [00:20:50 - 00:21:16]

    So you know what I think about. And, like, my background tends to be very much focused in the sales and marketing space and tools for salespeople and tools for marketing. And you just think about that process, you think about selling something. And my competency and focus as an entrepreneur predominantly is things for businesses. I'm not really focused on things for consumers. 


    Mike Pollack: [00:21:16 - 00:21:44]

    For businesses generally, there's one of two ways you can help them, broadly speaking. One is help make things cost less. So that usually involves removing people from a process. I'm not as excited about those kinds of problems because usually they all evolved to the same kind of thing, which is cut humans. The second kind of thing you can do that I think is more interesting is help humans be more impactful, help a human do a job better. 


    Mike Pollack: [00:21:44 - 00:22:18]

    And so in that way, I think of myself as kind of like a tool builder in that way. And so what I like about a space like sales and marketing, broadly speaking, is sales and marketing is art and science. The science part is, let's use numbers and math to figure out what's performing and what's working. The art is how do you get people interested, and how do you say something to the right person at the right time that's going to get them excited? And I think I'd say for me, as an entrepreneur, that problem is really big, and there's lots of things in there. 


    Mike Pollack: [00:22:18 - 00:22:46]

    And so I'd say we're working around a couple of things in that space, and in the coming months, I'll talk to it a little bit more. But, but I'd say broadly, what excites me is it's this enormous problem space that never goes away from here to eternity. People and businesses will always want to grow more, grow faster, and figure out how to do that better. So I feel good about being in a space that's in forever. Secondarily, I'm still really excited about that problem. 


    Mike Pollack: [00:22:46 - 00:23:21]

    I spent a lot of my career there and I think I really now understand it. I would encourage this to any founder or entrepreneur or anyone even in space, is there's a certain level of market founder fit that's important. And so for me, something I get really excited about is I like the people I'm building my tools for, I like the customers I get the opportunity to do business with. And I think the problem space again, is very interesting. And at this moment in time, with the inflection point of AI and llms, everything's getting kind of tossed and changed. 


    Mike Pollack: [00:23:21 - 00:23:41]

    The science is undergoing profound change. The art has a chance to change about how the art is done, the way maybe we moved, how art moves in waves and things kind of change rapidly. I think we're at one of those inflection points. So the short answer is we're doing something in that space. And in the coming months I'll share a little bit more. 


    Mike Pollack: [00:23:41 - 00:24:08]

    But in the short term, I would say I get really excited to help people use tools, software, processes to do things they're already doing better. I think we're at this unique moment where a bunch of things are happening at once. And so how do you put that all to work? And I think me and my co founder are excited about some ideas we have on that. But again, I'll take a cynical take on it just for a second, which is right now they're only ideas. 


    Mike Pollack: [00:24:08 - 00:24:52]

    And while they might be good ideas or they might be bad ideas, we've got to spend a lot of time with our customers to understand what they want and how they value that and how that's impactful for them. And I think that part taking like this ugly kind of like thing of clay, and then listening to customers to understand how or what they want and then translating what you hear into that finished thing is such like a hard, difficult, challenging thing. But I personally find enormous joy in that. And that's the part I get most excited about, because it leverages two skills that I think I'm pretty good at. Number one, which is really like trying to listen, listen between the words, listen around the words. 


    Mike Pollack: [00:24:52 - 00:25:19]

    And then number two, making something that somebody didn't ask for but they really wanted, I think that's kind of the skill. And then there's a whole part that comes after that, which is building the business and the structure and the team, which I think also is fun, but, but I get excited about that. So you ask, do I miss it. Here I am telling a love story of how excited I am to go chase product market fit again. And so I guess the answer is yes, I do. 


    Anastasia Koroleva: [00:25:20 - 00:25:38]

    I can see that that's very obvious. But I love that you actually put it in words so eloquently. Thank you so much. Okay, so that motivation right now is very clear. Did you have the same motivation when you started your business that you sold? 


    Mike Pollack: [00:25:38 - 00:26:08]

    So it's an interesting story. In the story of our business we sold, my co founder had built the beginnings of it. He deserves an enormous share of the credit for really building the technology. When we met, I'd say he had the technology figured out, but we hadn't quite figured out the business yet. Our product at the time was collecting data about cloud infrastructure in particular. 


    Mike Pollack: [00:26:08 - 00:26:41]

    What we would do with that data is the same way Google Maps maps the physical world, we'd map the digital world. And so we'd help businesses like large cloud vendors assess the potential, the priority, the propensity of businesses to buy. And so in that way, we built a really powerful system for collecting all that data. And then it took us probably three to four to five, maybe even six years to figure out how do you turn that into a business? I think this is where many startups stumble, and it's about fundamentally having the right set of skills around the table. 


    Mike Pollack: [00:26:41 - 00:27:32]

    One of the reasons why I love my co founder is I think in our Venn diagram, we both have pretty big circles, and we have a nice amount of overlap between us. And I think when we first met, I saw immediately the value of what he had created, and I saw a path where we collectively could take that and build that into a bigger, more impactful business. And so I'd say at that time, my motivation was the same. I was still passionate about building tooling, for helping sales and marketing, and I'd had literally right before that, a failed startup in that space. And so I was intimate with the buyer, I was intimate with the problem, and when I saw what my co founder put together, I saw right away like, oh, wow, I can help take where this is, and I can help help it get to the next level. 


    Mike Pollack: [00:27:32 - 00:28:11]

    And 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 I think my co founder and I independently set out to solve effectively the same problem, but from two different spheres. 


    Mike Pollack: [00:28:11 - 00:28:38]

    I think he approached it from a technically, how do you solve this with technology? I 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. 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. 


    Mike Pollack: [00:28:38 - 00:29:15]

    And so we 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. But 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. 


    Mike Pollack: [00:29:15 - 00:29:53]

    You and I are joining a group with a number of them. 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. And 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. 


    Mike Pollack: [00:29:53 - 00:30:12]

    Other ideas seem so alluring and so compelling. And again, this is where our brain tricks us about grass is greener. I 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, oh, that sounds so neat. 


    Mike Pollack: [00:30:13 - 00:30:53]

    You forget how much expertise you have and how hard and how long it took you to acquire it. Again, earlier in this interview, 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 again. 


    Mike Pollack: [00:30:53 - 00:31:05]

    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. 


    Anastasia Koroleva: [00:31:05 - 00:31:48]

    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 skill, talent that can be applied across different industries, then it's fine. So 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? 


    Anastasia Koroleva: [00:31:48 - 00:31:53]

    And maybe that's why you feel so strongly about that. Am I wrong? 


    Mike Pollack: [00:31:53 - 00:32:20]

    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 my expertise is generally around human behavior. And I think sales and marketing and in a business context is fairly straightforward and bounded. I think about entrepreneurs who operate in the consumer space. 


    Mike Pollack: [00:32:20 - 00:32:47]

    And 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. 


    Mike Pollack: [00:32:47 - 00:33:12]

    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. That means the outcomes potentially are smaller. That means the failure is also 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. 


    Mike Pollack: [00:33:13 - 00:33:34]

    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. I think if I can do that, I'm very pleased to do that. 


    Mike Pollack: [00:33:34 - 00:33:57]

    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 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. 


    Mike Pollack: [00:33:57 - 00:34:54]

    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 now. 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, you know, 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. I think your comment about a network is very valuable. 


    Mike Pollack: [00:34:54 - 00:35:33]

    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. 


    Mike Pollack: [00:35:33 - 00:36:04]

    And 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. 


    Mike Pollack: [00:36:05 - 00:36:27]

    I think that part is very hard. So 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. 


    Mike Pollack: [00:36:27 - 00:36:40]

    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 a small lowercase genius associated with it, but I'm happy to stick to my lane and do what I can do inside of there. 


    Anastasia Koroleva: [00:36:40 - 00:36:59]

    It's so 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? 


    Mike Pollack: [00:36:59 - 00:37:40]

    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. The second layer is my team, and again, 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. 


    Mike Pollack: [00:37:41 - 00:38:16]

    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. 


    Mike Pollack: [00:38:16 - 00:38:37]

    And 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. 


    Mike Pollack: [00:38:37 - 00:38:52]

    Then 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. And there's moments where I see founders raising some amount of money. I'm like, wow, that's crazy. 


    Mike Pollack: [00:38:52 - 00:39:00]

    That should have been me. But 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? 


    Mike Pollack: [00:39:01 - 00:39:21]

    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. 


    Mike Pollack: [00:39:21 - 00:39:50]

    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, but I've just found let a lot of that go. I think the younger version of myself was much more active about status. I need to get to this level. I want to be the CEO of this. I want to do this. 


    Mike Pollack: [00:39:50 - 00:40:18]

    I think just the benefit of maturity and life and experience is recognizing that's all noise. If it doesn't matter to you, then it doesn't matter. 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 when you scroll through the pictures and you see somebody on their whatever, doing their whatever, an emotion you could feel is, I should be there, or why didn't I get invited? Or why don't I have that? 


    Mike Pollack: [00:40:18 - 00:40:42]

    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. 


    Mike Pollack: [00:40:42 - 00:41:09]

    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. That 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. 


    Mike Pollack: [00:41:09 - 00:41:33]

    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. 


    Anastasia Koroleva: [00:41:33 - 00:41:59]

    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 world, you'll 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. 


    Anastasia Koroleva: [00:42:00 - 00:42:09]

    And are you tempted to and not start the business quite yet while the children are so small? 


    Mike Pollack: [00:42:09 - 00:42:35]

    So, 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, we started our m and a conversation started in October, and then the business was sold in March, so maybe about five, six months. 


    Mike Pollack: [00:42:35 - 00:42:48]

    And I had a daughter in November. So, like a month into the m and 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. 


    Mike Pollack: [00:42:48 - 00:42:58]

    I don't remember that being that bad. It was very hard. Again, the m and A. M and A is a challenging experience. It's hard. 


    Mike Pollack: [00:42:58 - 00:43:20]

    And then having a newborn is its own challenge. And my co founder now has at this time, maybe seven or eight or nine month old, and he was asking me about, like, you know, at the time we were selling the business, how did I. 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 and we got through it. 


    Mike Pollack: [00:43:20 - 00:43:34]

    And maybe again, your comment about trauma, which I picked out a little bit, perhaps is accurate because my brain's totally hidden. It 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. 


    Mike Pollack: [00:43:34 - 00:44:15]

    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 me and my co founder, when we talk about what we want to do next, we spend 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. 


    Mike Pollack: [00:44:15 - 00:44:25]

    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 and do more emails. 


    Mike Pollack: [00:44:25 - 00:44:57]

    And 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. And 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? 


    Mike Pollack: [00:44:57 - 00:45:18]

    And 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. And I don't think, 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. I think it's doable. 


    Mike Pollack: [00:45:19 - 00:45:58]

    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, should I find that it's not sustainable or 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? I 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. 


    Mike Pollack: [00:45:58 - 00:46:07]

    And I think that's where the difference in being an, oh, you need a nanny. Oh, yeah, nanny. Yeah, exactly right. Yeah, all the resources, right. Yeah, yeah, exactly right. 


    Mike Pollack: [00:46:07 - 00:46:31]

    A nanny, all the resources, right. And that's where I think, 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. 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. 


    Mike Pollack: [00:46:31 - 00:46:44]

    And 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. 


    Mike Pollack: [00:46:44 - 00:47:16]

    When I look back at things I was doing, my co founder and I had a great conversation just a couple months ago. We were talking about we probably really only needed to do 30 or 40% of the things we actually did, but we needed to do them 60 or 70% harder. You just think about that idea of, again, I was always busy in the earliest days or even in our business, I was selling, I was writing spec, I was doing whatever. Again, if I'm really honest about it, was any of it really that good? Was I doing my best work? 


    Mike Pollack: [00:47:16 - 00:47:52]

    If I had just said, hey, instead of doing ten 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. 


    Mike Pollack: [00:47:52 - 00:48:21]

    And 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 wherever you need more support. 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. 


    Mike Pollack: [00:48:21 - 00:48:56]

    As an experienced person, I desperately ask for help all the time, everywhere I possibly can, and I have no shame in doing so. And 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? 


    Mike Pollack: [00:48:56 - 00:49:21]

    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. And 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. 


    Mike Pollack: [00:49:22 - 00:49:45]

    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 twelve months and I'll give you a more cogent, real answer on this one. 


    Anastasia Koroleva: [00:49:45 - 00:49:55]

    So talking about money, how does your relationship with money then the meaning of wealth change for you after you sold your business? 


    Mike Pollack: [00:49:56 - 00:50:26]

    So before I sold the business, I had moved to San Francisco. Now, almost ten years ago 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. 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. 


    Mike Pollack: [00:50:26 - 00:50:49]

    I didn't have access to it. I'd go out to dinners with people. And, you know, 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? 


    Mike Pollack: [00:50:49 - 00:51:06]

    How can we ever have a house? How can we ever. Im living in a rent controlled place. I mean, that helped sustain me for many years when we sold the business and our economics changed radically. I think our relationship with means and wealth changed as well. 


    Mike Pollack: [00:51:06 - 00:51:31]

    We 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 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? Carries a big burden on me. I don't necessarily feel that. 


    Mike Pollack: [00:51:31 - 00:51:57]

    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. And I think, you know, we, my wife and I have a really reasonable mindset where, let's 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. 


    Mike Pollack: [00:51:57 - 00:52:42]

    I don't think our ambitions or our aims are ostentatious or gross in that way. And so, you know, I'd say 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, and it's a strange thing how wealth is portrayed, particularly in America, right, that 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. 


    Mike Pollack: [00:52:42 - 00:53:15]

    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 from for wealth that I think about is, again, like the vehicle, it gives you optionality. It 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. 


    Mike Pollack: [00:53:16 - 00:53:42]

    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 make people scared or do all kinds of strange things. That, again, is peculiar to me. 


    Mike Pollack: [00:53:42 - 00:54:26]

    I don't know, I didn't, 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. And 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 now you're asking for the money, you're trying to do it, and it's a hard thing because many people are telling you no. 


    Mike Pollack: [00:54:26 - 00:54:55]

    And then there'd be this day where somebody 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 the, 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 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. 


    Mike Pollack: [00:54:55 - 00:55:20]

    I think the same is true when you accumulate wealth. The 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 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. 


    Mike Pollack: [00:55:21 - 00:55:51]

    And so I guess there 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. 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, but 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 to see some things along the way. 


    Mike Pollack: [00:55:51 - 00:55:54]

    And so in that way, it's been a wonderful thing. 


    Anastasia Koroleva: [00:55:54 - 00:55:57]

    Do you ever feel guilty about your financial success? 


    Mike Pollack: [00:55:57 - 00:56:22]

    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. I'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. 


    Mike Pollack: [00:56:23 - 00:56:41]

    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 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. 


    Mike Pollack: [00:56:41 - 00:57:06]

    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. And 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. 


    Mike Pollack: [00:57:06 - 00:57:44]

    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. 


    Mike Pollack: [00:57:44 - 00:58:17]

    I 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. 


    Mike Pollack: [00:58:17 - 00:58:38]

    So I feel very good that we're trying to use our means, again to leave things better than we started with them. And 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. 


    Mike Pollack: [00:58:38 - 00:59:01]

    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. 


    Mike Pollack: [00:59:01 - 00:59:07]

    If you're feeling guilt, go fix it. What are you waiting for? And so the answer to your question is, no, absolutely not. 


    Anastasia Koroleva: [00:59:07 - 00:59:09]

    What are the most important values for you? 


    Mike Pollack: [00:59:10 - 00:59:33]

    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. I think being authentic to who you are is a key value. 


    Mike Pollack: [00:59:33 - 00:59:56]

    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. That 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. 


    Mike Pollack: [00:59:56 - 01:00:14]

    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, ah, I'm so frustrated at you. 


    Mike Pollack: [01:00:14 - 01:00:43]

    How could you do this? 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 are doing or why it's so important. 


    Mike Pollack: [01:00:43 - 01:01:13]

    I think I now have, again, the privilege, the time to do that and the time to think about that with the next one. So 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. It's just, again, try and pay it forward any way you possibly can. I think about, as an entrepreneur, I like the, I like the Thomas Edison adage of his idea of failing his way to success. 


    Mike Pollack: [01:01:14 - 01:01:44]

    You know, I think, you know, 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 competence 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. I don't know if that's the cure all, end all, be all. 


    Mike Pollack: [01:01:44 - 01:01:55]

    But again, if you take that as a northernmost star, seems like a reasonable one. And so maybe, maybe that's a corollary to the third point, but that would say, that would be broadly how I would probably think about it. 


    Anastasia Koroleva: [01:01:55 - 01:02:02]

    Is spirituality part of how you perceive the world? What are your thoughts on that? 


    Mike Pollack: [01:02:02 - 01:02:40]

    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 experienced and seen things that are just bigger than me, bigger than humans, bigger. When 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. 


    Mike Pollack: [01:02:41 - 01:03:15]

    And when you see a team, like a high functioning team, whether it's as actors or 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. 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. 


    Mike Pollack: [01:03:16 - 01:04:01]

    And 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 spirits that exist broadly and the spirituality that collectively comes out of that. 


    Mike Pollack: [01:04:02 - 01:04:31]

    But 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. 


    Mike Pollack: [01:04:31 - 01:04:58]

    I think 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. And 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 a crap roll the dice, but you just got to keep playing the game. And I think that's. That's an exciting part of, you know, being in existence in the first place. 


    Anastasia Koroleva: [01:04:58 - 01:05:09]

    So 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? 


    Mike Pollack: [01:05:10 - 01:05:43]

    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. 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, I was burned out, again, broadly speaking, I think there's only a couple of reasons. 


    Mike Pollack: [01:05:43 - 01:06:04]

    Someone sells a business. 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. 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. And then the next question is after that. 


    Mike Pollack: [01:06:05 - 01:06:23]

    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. 


    Mike Pollack: [01:06:23 - 01:06:39]

    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 changed this, or, I'm happy to be an editor. It's real hard to be a creator. 


    Mike Pollack: [01:06:39 - 01:07:22]

    And so I think the blank canvas problem is real for anyone, anywhere who's making anything, whether it'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? And again, was it a trauma driven decision of, like, I need to get rid of this thing, I can't do it anymore? 


    Mike Pollack: [01:07:22 - 01:07:54]

    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. And I, 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? 


    Mike Pollack: [01:07:54 - 01:08:13]

    Why 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 spent a lot of time talking about what did you love while you were doing, when you were doing it? What was your favorite part? 


    Mike Pollack: [01:08:13 - 01:08:40]

    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 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 that moment. 


    Mike Pollack: [01:08:40 - 01:09:01]

    Right? Obviously, we're fine in the end. So I think I'd spend a lot of time doing that. And I think most founders, 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. 


    Mike Pollack: [01:09:02 - 01:09:33]

    And that's why 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 I think I'd spend more time talking about, what did you do before we didn't 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. 


    Mike Pollack: [01:09:33 - 01:09:50]

    If 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. 


    Anastasia Koroleva: [01:09:50 - 01:10:21]

    Yeah, sometimes they know the answer. Sometimes they have to fix 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 or BC. Right. Because they think, oh, that's the path that people around me seem to be doing. 


    Anastasia Koroleva: [01:10:21 - 01:10:36]

    But then you go to a different part 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. 


    Mike Pollack: [01:10:37 - 01:11:01]

    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. They become large philanthropists and support these organizations. 


    Mike Pollack: [01:11:02 - 01:11:26]

    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, I know something about startups, but I don't know anything about art. 


    Mike Pollack: [01:11:26 - 01:12:05]

    I don't know anything about how to structure a museum. And 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. 


    Mike Pollack: [01:12:05 - 01:12:26]

    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. Sure, maybe that brings you joy, but I've 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. 


    Mike Pollack: [01:12:26 - 01:12:54]

    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, I'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. 


    Mike Pollack: [01:12:54 - 01:13:29]

    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, been very hard to break out of that. 


    Mike Pollack: [01:13:29 - 01:13:58]

    And so 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 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. 


    Mike Pollack: [01:13:58 - 01:14:05]

    And stepping out of that lane is so scary. And I think that's hard. And I think that holds a lot of people back. 


    Anastasia Koroleva: [01:14:05 - 01:14:44]

    Yeah, no, absolutely. And 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 of 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 just commit to another ten or 20 years of a particular activity. 


    Mike Pollack: [01:14:44 - 01:15:14]

    I think that's a fair point. And I'd add to that that there's something that's peculiar about the tech space that I've encountered is many founders or people who get into technology. I'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. We'll get humans out of here. 


    Mike Pollack: [01:15:14 - 01:15:47]

    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. AI 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. 


    Mike Pollack: [01:15:48 - 01:16:08]

    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. 


    Mike Pollack: [01:16:08 - 01:16:42]

    And so I tend to think my skillset means I can work with humans on many different kinds of problems. I'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, or they're problems of technology, and if you can just help humans come together, you can do these amazing things. And so I think many founders aren't as excited. 


    Mike Pollack: [01:16:43 - 01:17:04]

    There are plenty. But many tech founders in particular aren't as excited to really understand the human element of things. And instead, because their expertise might be on the technology, they're like, oh, we'll 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. 


    Mike Pollack: [01:17:05 - 01:17:23]

    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? 


    Mike Pollack: [01:17:24 - 01:17:58]

    I think your point is fair, and 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. 


    Mike Pollack: [01:17:58 - 01:18:18]

    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, and 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. 


    Anastasia Koroleva: [01:18:18 - 01:18:40]

    I am enjoying this enormously, and I can talk to you forever. But I also realize, you know, I need to let. 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 ten, how would you rate your level of fulfillment? 


    Mike Pollack: [01:18:40 - 01:18:50]

    Fulfillment. Ten being I have everything I've ever wanted, ever. And zero being I have nothing. I have nothing I wanted. 


    Anastasia Koroleva: [01:18:50 - 01:18:53]

    Whatever you define it as, say, at. 


    Mike Pollack: [01:18:53 - 01:19:13]

    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. 


    Mike Pollack: [01:19:13 - 01:19:32]

    So, 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. 


    Mike Pollack: [01:19:32 - 01:20:01]

    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. So I'd say I don't know how anybody could ever actually be a ten. 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. 


    Mike Pollack: [01:20:02 - 01:20:04]

    Six, seven, eight. Maybe a good day. 


    Anastasia Koroleva: [01:20:04 - 01:20:09]

    Brilliant. And my last. How do you want to be remembered? 


    Mike Pollack: [01:20:09 - 01:20:27]

    Two answers. Number one, someone who told good jokes at the right moments in time. That would be. That's, like, the silly part of me. But the second one would be 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. 


    Mike Pollack: [01:20:27 - 01:20:32]

    And if I get those four things. But if I get, like, one or two out of the four, I'd say that's a victory. 


    Anastasia Koroleva: [01:20:34 - 01:20:44]

    Mike, thank you so much. It was absolutely amazing. And of course, we have to stop, but I hope we'll continue in our live conversation soon. 


    Mike Pollack: [01:20:44 - 01:20:58]

    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. 


    Anastasia Koroleva: [01:20:58 - 01:20:59]

    Thank you so much.


 
Anastasia Koroleva
Previous

Dave Hersh. Post-Exit Rebirth: How I Found True Freedom and Energy
Next

$100M-Net-Worth Retired Founder: Chasing Energy Instead of Money