Dave Hersh. Post-Exit Rebirth: How I Found True Freedom and Energy
Episode - 26
Dave Hersh. Post-Exit Rebirth: How I Found True Freedom and Energy
Dave Hersh. He sold his company through an IPO 13 years ago, then spent several years with the VC firm Andreessen Horowitz.Today, Dave is more fulfilled and productive than ever.He credits a 10-year existential crisis that led to his “deep reprogramming” and “rebirth.”Today he talks to us about finding true self, sovereignty, and inexhaustible fuel sources.
What We Discussed:
00:00:00: Introduction to Wilderness of the Unknown
00:00:11: Dave Hersh and His Background
00:01:33: Going Back to Dave's Company Journey
00:06:14: Dave's Experience Post-Exit
00:09:00: Exploration of Identity Struggles
00:11:01: On Hoffman Process
00:13:12: Dave's Experience with Art of Accomplishment
00:16:22: Discussing the Process of Transition and Transformation
00:19:26: The 10-Year Struggle and Its Impacts
00:22:06: Importance of Letting Go of the Past
00:23:16: Navigating the Entrepreneurial Wilderness
00:25:20: Transition from Jive to Andreessen Horowitz
00:27:23: Expectations from the Venture Capital Route
00:29:02: Personality Differences and Impact on Career Paths
00:33:30: Moving on from Venture Capital
00:35:52: Acquiring Stuck Startups and Identifying Their Core
00:37:00: Importance of Understanding Your Core Business
00:39:31: Challenges of Scale and Growth in Business
00:43:05: Acquiring and Restructuring Businesses based on their Core
00:44:31: Thoughtful Experimentation and Strategic Growth After Understanding Market Pull
00:44:47: Business Growth Strategies
00:48:35: Introduction to Writing
00:50:49: Definition of Success
00:54:32: Evolving View on Money and Wealth
00:57:44: Importance of Surrounding With Right People
01:02:25: Alignment of Business Activity and Personality
01:03:17: Emergence of the Creator Economy
01:04:32: Discussion on millennials and their work motivations
01:05:54: Question about personal fulfillment
01:07:26: Rating personal fulfillment
01:08:33: Advice for someone who recently sold their company
01:09:55: What keeps one awake at night
01:10:59: Reflection on divorce and personal growth
01:11:42: How one wants to be remembered
01:12:11: Anticipation for upcoming book
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Dave Hersh: [00:00:00 - 00:00:11]
For true transformation to happen, there needs to be this willingness to accept the wilderness that we're walking into and that it is unknown. And that rebirth doesn't happen unless you sit in the underworld for a while.
Anastasia Koroleva: [00:00:11 - 00:00:36]
Dave Hirsch, he sold his company through an IPo 13 years ago, then spent several years with the VC firm Andreessen Horowitz. These days, Dave is more fulfilled and productive than ever. He credits a ten year existential crisis that led to what he calls deep reprogramming and rebirth. Today he talks to us about finding true self sovereignty and inexhaustible fuel sources.
Dave Hersh: [00:00:36 - 00:01:22]
If I'm doing what I'm on this planet to do, and I can feel that it is touching the people around me in meaningful ways, kind of all there is. I surround myself with the people who are soulful, who are trying to do the work and show up in the fullest version of themselves possible. The upslope is like the thrashing and the kind of, I gotta do another company or I gotta make more money, and I'm this person in the world, and now I gotta advance my brand. And it's like all this kind of egoic thrashing and pain that you got to go through, but the downslope is going, oh, that's all b's, all. This identity is ultimately something that you realize doesn't matter, but you can't get there without all of the work along the way. Hello, Dave. Hey, how's it going?
Anastasia Koroleva: [00:01:22 - 00:01:26]
Very well. Very happy that you are joining me today. Thank you so much.
Dave Hersh: [00:01:26 - 00:01:28]
Absolutely happy to be here.
Anastasia Koroleva: [00:01:28 - 00:01:32]
Really looking forward to dig into your life quite deep today. Hope you're ready.
Dave Hersh: [00:01:33 - 00:01:33]
Always.
Anastasia Koroleva: [00:01:33 - 00:01:43]
I'm really interested in what happened to you after you sold your company, which in your case, happened 13 years ago. Am I right?
Dave Hersh: [00:01:43 - 00:01:44]
Yep, that's right. Yeah.
Anastasia Koroleva: [00:01:44 - 00:02:05]
So it took you quite a while to build jive software, and then you ran it up to its ipo, and then you left. And I would love us to go back to that moment. So you tell me a little bit about the company, why you started it, why you sold it, and then we'll go deep into what happened after that.
Dave Hersh: [00:02:05 - 00:06:37]
So we started jive under very adverse conditions, which was my first day to go meet the co founders was September 11, 2001, in New York City. So, yeah, you can imagine that was a strange time. All of us were following our significant others to grad school out in the New York area. And I had worked with the technical founders at a previous startup and was on my way to the city when the world changed. So it was maybe the week after that, we finally got together in person to talk about what we're going to do with this company. But it's very clear that we were going to not have traditional venture funding as part of our trajectory, because that just wasn't available at the time. Thankfully, you know, what had happened was the company was originally an open source product that my two co founders had developed and had a pretty big following, and it was essentially threaded discussions, so discussion forums, and this was circa 2001, obviously, and that was still a popular form of communication and collaboration on the Internet. So there are a lot of people that knew the product, and I came in to help them turn this open source application into a fully functioning company. And revenue was going to be really important because we were going to have to bootstrap it. So we built it up in New York City for a couple years and continued to grow the business there, then ran into the scale challenges that come with New York City being very expensive, hard to find engineers, and moved it out to Portland, Oregon. We grew it in Portland for a few years, and to great effect. Portland was a wonderful town, had a lot of talented developers and salespeople, the things that we needed to build a bootstrappy company. And over the course of the next several years, so this is 2004 to 2007, we built it up again, continuing to bootstrap it. Then we built this really healthy, profitable. It was probably a $12 million business at the time. And this was along the time that Facebook came part of the national consciousness, and people started asking questions about, how do we take these ideas behind Facebook and apply them to what we do at work. So we saw this really big opportunity where the whole nature of digital communication and collaboration was changing. And because of our background in the space, we had a good lead. And then we have a lot of other companies coming online. And so we decided to raise venture capital at that point. And what it meant was building out a whole new product for this space and really having to end of life the old products. And so we did that, and over the next several years, built up a new business, essentially selling large companies on social collaboration technology, and went probably zero to 55, 60 million over the next three years, which is obviously a tremendous ramp, and kind of took it out of me, as I'm sure a lot of your listeners would understand. That's that period of massive scale that is simultaneously wonderful and beautiful, but really can destroy you personally, too. And it was this point that the board said, we want to take this company public. And I, you know, having done it at that point, for eight and a half, nine years, was reticent to be a public company CEO. And it was a really difficult place because I had young kids at home and I was never at home. And it had gotten pretty difficult to manage both home and work life at that point. So I became chairman of the company as we got it ready to go public, and it went public in 2011 and stepped away from the company entirely in 2011 so that I had a little more flexibility with what I did. And that began that process, that odyssey of post economic thrashing and searching, and I went through so much. I really hope that my experience could be helpful to your listeners because there are stages and there are psychological transition points that one goes through after an experience like that. And I did all that. I messed up a lot. And so hopefully people can learn from the mistakes that I made for the challenges that I had in my own journey.
Anastasia Koroleva: [00:06:37 - 00:06:48]
I can't wait to find out all of it. So where do you start the moment you will no longer see or founding CEO, in your case, how did it feel?
Dave Hersh: [00:06:48 - 00:08:15]
I think the initial stepping down from CEO into chairman was relieving because I was so exhausted from working so hard to get it to that point, but also very confusing in that it's ripping a band aid off and suddenly your identity is gone and you're no longer in the ebbs and flows of the life that gave you purpose for a long time. So I think there's a natural response, which is just relief and being able to let go for the first time in a while. But after, you know, a month or two, that starts to become confusing. And that's when some of the insecurity and doubt will creep in and a lot of the existential questions around, if I am not that, who am I? And what do I do to regain a sense of place in the world? And identity. And identity is obviously something very important to founders and entrepreneurs. So when you suddenly don't have that toehold or the infrastructure of what it is that makes me who I am, it can be very, very confusing. So I think it's, yeah. Relieving for a little while, and then the big questions start to emerge.
Anastasia Koroleva: [00:08:15 - 00:08:26]
Absolutely. So how did you deal with it? Identity? Let's focus on that issue first. How long did it take you and what were the things you tried?
Dave Hersh: [00:08:26 - 00:10:53]
Yeah, so this is part of the challenge over the long run, as that the longer term journey is one where you recognize that all of these egoic conditions around you are false. All this identity is ultimately something that you realize doesn't matter, but you can't get there without all of the work along the way. That's jumping to the conclusion. But for a recently exited founder, you have to go through this process, and you have to have these struggles around identity. And there probably is going to be a little bit of thrashing. The things that were most helpful to me along the way, which I eventually figured out was just doing deep inner work and reprogramming a lot of the patterns and provisional identities and ways that I was being told, you know, who I was by society. That took a lot of deep reprogramming, which is not an intellectual thing. And I think entrepreneurs tend to rely on the mind as the mechanism for getting out of a situation that they're in that can serve them really well, at the same time that the identity of a CEO can serve them really well to succeed in the world and give them drive. But the loss of a company and a role, or a role inside that company, or both, will prompt a lot of pain. And that pain is going to hopefully drive a series of deeper investigations into self that will create the sense of peace over the long run. In other words, entrepreneurs over identify with their companies, and that can be good for the motivation it creates, for the fuel and the fire, and for them to create something out of nothing. However, those same strengths that got them to where they are in their twenties and thirties start to become the baggage that creates a lot of pain later, especially after you've had an economic event like that. So for me, I think the original question was, what did I do? So it started, maybe the gateway for me was doing a thing called the Hoffman process, which is a popular.
Anastasia Koroleva: [00:10:53 - 00:10:59]
Yeah. Could you explain it to those who haven't experienced it?
Dave Hersh: [00:10:59 - 00:13:42]
Sure. Yeah. So I did Hoffman, maybe 2016, and I think that was a really powerful gateway into a series of inner work, which was meant to dismantle this egoic scaffolding that was causing a lot of the pain. Hoffman is very good at, what I would say, excavating your root structure. So basically understanding, why am I the way I am? You know, why am I this complex set of patterns? We do so much in life that is subconscious, that just happens because it's been programmed into us, and we don't realize it. We think, this is just who I am, without really saying, well, why is this who I am? Why are these patterns there? Where do they come from? Which ones are serving us? Which ones are no longer serving us? Which ones are creating challenges and creating a lot of the pain? So Hoffman's very good at looking back to why those patterns exist, where they came from, in reflection of the families that we came from, the societies that we came from, and then seeking to reprogram those responses in very healthy ways. And it's done through emotional, you know, and somatic work and a deeper connection with something larger than yourself. And so words are going to get in the way, right? People would say spiritual, they will say God, they will say soul, but, you know, it doesn't really matter. It's going to say different things to different people, just, you know. But the point is, it works. If you can tap into that deeper sense of resonance with a larger system that you're a part of, whether it's through scientific understanding or spiritual connection, it does work. And so I think Hoffman is very good for people who haven't done a lot of work, who need a deep, kind of break the horse down transformation that allows them to see the whole self as a complex system of patterns and processes. And that's what is keeping people stuck in the eddies of life, as opposed to flowing down the river and being happy. They get stuck in eddies, and they don't always know why. And just relying on the intellect to get yourself out of that eddy rarely works. So that's why talk therapy is good, but it's not going to change the game. And so for me, Hoffman was the. The gateway to doing a lot of other inner work that was meant to dismantle that egoic baggage that was keeping me stuck in pain.
Anastasia Koroleva: [00:13:42 - 00:13:49]
Amazing. Okay, so that was the gateway. What else did you do that was helpful or not helpful?
Dave Hersh: [00:13:49 - 00:14:38]
Yeah, so, you know, I did do talk therapy throughout. There was. There's a group that I got involved with several years ago called the art of accomplishment, which the name is very different than the actual work you do, but it's meant to meet people where they are, with a, you know, people who are achievers, people who are seeking to be their best selves and to, you know, create in the world and do things on a larger scale. So art of accomplishment was maybe taking the, you know, yellow belt of the Hoffman process and advancing to blue or green. I don't remember how the belts went, but it was taking it up a level.
Anastasia Koroleva: [00:14:38 - 00:14:39]
Martial art.
Dave Hersh: [00:14:40 - 00:15:43]
Okay. Yeah, the belts were getting darker. Put it that way. Yeah. And I'm colorblind, so I, you know, take that with a grain of salt. But it was taking that even further, you know, whereas Hoffman was looking back at, you know, how I became the way I am. Art of accomplishment was doing a lot of work to shift how I showed up in the world. And so being able to not only reconcile with voices in the head and limiting beliefs, but to truly live more soulfully, more essentially, and ultimately, you know, the irony of all of it is that it makes you way more productive and way more focused on a deeper fuel source. Meaning the early companies we do, the fuel for the fire may be more egoic in nature. We're trying to prove ourselves through the company. We have insecurities. We're trying to earn love. We're trying to prove that we're good and that we're worthy of, you know, the love that we seek.
Anastasia Koroleva: [00:15:44 - 00:15:45]
Yeah, absolutely.
Dave Hersh: [00:15:45 - 00:19:10]
That which is. Yeah. And that creates a lot of drive and motivation, and it's amazing. But the hope is that eventually, that's an exhaustible fuel source. Right. That can wear us out, and, you know, as you've seen, it can drive people into, you know, states of depression or anxiety and, you know, alcohol abuse. There's all kinds of things that will come if you don't reconcile with it. And so the hope for someone who's got an entrepreneurial drive and who cares about creating in the world is that they find a way to tap into a deeper fuel source, an inexhaustible fuel source. And I think that's the one that Ari of accomplishment helped me connect with. And that was a series of week long intensives and a ten week course called Masterclass that took place over maybe 10 hours a week of work and a lot of partner work. So I've continued to do their work, and it's led me to other modalities as well. And that's been one that's really helpful to that process of tapping into that deeper, inexhaustible fuel source so that what I create in the world now is much more me, is not something that I'm over identified with and is just coming from a place of passion and, you know, can continue to flow for me in a beautiful way. So this is 13 years later. Right. And so I. It took a long time to go through that process, and some of these things, I do not know, were available to me. And, you know, I spent a lot of time stuck in those eddies. I was depressed. I was anxious. I was thrashing around trying to recreate what I once was. I think Jung calls that a regressive reversion, where when you enter the wilderness after a death of your old self, you get really scared in that wilderness, and you want to go back to what you were before. Right. As opposed to continuing to go through it and doing real transformation work. You say, well, I'm gonna go be a CEO again. I'm gonna go do that thing again that served me before. Yeah, right. And then I'll know I'll be loved again. Then it'll all feel okay. And it's probably okay to try that. And I certainly tried that multiple times, you know, even when I was aware of it and saying, I think I'm doing this thing, which is trying to be who I was before, I would still do it because I didn't know what else to do. And so I think it's worthy of trying that out to see how it fits. And maybe you can try to approach it from different angles. But think for entrepreneurs, and I see this happen a lot, what they do is I have money now, and that's amazing, but I don't have identity anymore, and I don't have purpose, and I don't have a connection to this community. I'm not climbing a mountain with people in the way that I once was. And so let me try to find a way to reconstruct that. But it's really hard when you've changed your economic equation and the situation has changed. Doing the same thing again does not really support the human need for growth and transformation. Right. So I rarely see that work with entrepreneurs, and, and yet I do see it happen a lot where that's the pattern.
Anastasia Koroleva: [00:19:11 - 00:19:26]
So how long you think it took you before you, you got to some point of clarity about what it is you really wanted to do or the direction you wanted to go in?
Dave Hersh: [00:19:26 - 00:19:30]
You know, I think it was ten years of struggle, to be honest.
Anastasia Koroleva: [00:19:30 - 00:19:31]
Yeah. Yeah.
Dave Hersh: [00:19:31 - 00:19:34]
You know, there were moments a lot.
Anastasia Koroleva: [00:19:34 - 00:19:59]
From people who exited more than ten years ago that they say it's at least ten years. It was the same for me. I had my first exit 13 years ago, like you, but you probably also know that people who just exited, they expect that weeks or months later they'll get to the point of complete clarity and new purpose and all of it. And it doesn't happen. It takes a while.
Dave Hersh: [00:19:59 - 00:20:25]
Yeah. They're entrepreneurs, so they're very good at storytelling. I see a lot of entrepreneurs that I help and coach that have woven a complex and beautiful narrative around where they are, but it belies what's really going on, which is that it's going to take a while and you're going to struggle. Right. And the intellect is a powerful salesperson.
Anastasia Koroleva: [00:20:25 - 00:20:30]
Yeah. So it does different kind of work than what we're used to.
Dave Hersh: [00:20:30 - 00:25:15]
Yeah. I mean, it's rare that I meet the entrepreneur who's, you know, had the exit, who comes in and goes, I don't know. I'm going to struggle for a while, and I'm going to learn to love the struggle, and I don't have answers, and I'm just going to, you know, try to die to self and go as deep as possible. It's rare that I hear that, but that would be the most enlightened approach. You know, there's. There's a book that I read early on called transitions by William Bridges, and it was written in the seventies, and it's a beautiful book, which is about the beauty of the liminal, which is this limbo between old self and rebirth of the new self. And as entrepreneurs, we have this desire to fix, to solve, to come up with a new idea, the brilliant thing. But there is, for true transformation to happen, there needs to be this willingness to accept the wilderness that we're walking into and that it is unknown. Rebirth doesn't happen unless you sit in the underworld for a while. And I may be using terms that are alienating to some of the entrepreneurs. But what it means is that old you, the CEO who was succeeding on this scale, who was leading people, when you are no longer in that position, there is a long period to celebrate the death of that version of yourself, to grieve it, and to go through the process of letting go of that old. And there may be other elements of that identity, too. Like, you know, your family member or you're this, you know, you're a friend in these ways, and you support your family in these ways, there's a lot of these egoic, provisional identities that we assume along the way. So when you have a big dramatic event like that, like, you know, exiting your business, the best thing to do is to really ritualistically die to that old self, find a way to say that part of me is no longer, and I love that part of me, and it's beautiful. But for me to enter a new phase of life that is more deeply connected to who I really am, I am going to have to go through a period where I don't know what's really happening. And that's what the book was about. It's about this, this beautiful, liminal space between old you and new you, and that you can't just be reborn as much as entrepreneurs are gonna be like, okay, now I'm this person, and I'm gonna be a vc, I'm gonna make investments, and that's gonna be my new thing that's not really doing anything substantial. It's not fixing the inherent problem. So I think it's the hardest thing for entrepreneurs to do is to go into this wilderness and just say, I don't know. I don't know how long this lasts. I don't know what is going to be entailed in this. I just know that I seek true joy and I know that that comes from a willingness to die to all of these ideas about who I am and to that former version of myself. And only when you truly grieve it and let go and exist in this liminal place for a long time do you start to get these little signals of, what is that me, you know, these little pulls around energetically. I want to do more of this. And this feels right. And you start kind of slowly moving out of the wilderness because you get these little bits of light and you go, okay, there's something over there, let me follow it. And that's a beautiful place to be. But you really have to immerse yourself in the unknown for a while, right? Because when you're in the thick of it, you have the blinders on and you just know, like, we're climbing up this mountain, we're climbing up this mountain. But when you have the blinders on, it's very difficult to be attuned to signals that will pull you in new directions that are more uniquely you. And this is, again, the hardest part for any entrepreneur. So that book is really helpful for me to understand what that liminal place really looks like and that you can't force rebirth, you can't force transformation. What you can do is just continue to immerse yourself in the work and continue to walk through this wilderness and learn to love being in that middle ground and being a ghost in between worlds. But when you are a ghost, you're subject to all these, you know, frequencies and signals and ideas and people and energy that you wouldn't have access to if you were staying in that mode of the entrepreneurial mindset. So I feel like I've been talking a lot. So sorry. I hope this is helpful.
Anastasia Koroleva: [00:25:15 - 00:25:34]
That's the whole idea. You should be talking a lot. That's the whole idea. So I understand that you only had a few months after you left Jive and before you joined Andreessen Horowitz. So when did you find that time and space in your head to do all this hard work?
Dave Hersh: [00:25:34 - 00:27:18]
Yeah. So I think right afterwards, you know, I had probably four months, someone told me one time that you need one month for every year that you hit it hard. That was a rule of thumb. I don't know if that's true or not. I think, having recently gone through a divorce, that there's a similar pattern or, like, you just, you know, there's a timeline that seems to make sense. So I think, you know, after four months or so, I started getting creatively anxious and wanting to do more. And so I just, like, a lot of people, got involved in incubating companies and advising and sitting on boards and investing and, you know, doing a lot of that post economic founder type of stuff. But it just seemed like a flurry of activities that weren't making me happy. It was just kind of filling up space. I went to Andreas and Horowitz for a few years shortly thereafter, which was fascinating. And they're really, you know, impressive group of people. And I loved being there. It was not my happy place. I was more of a blue collar, you know, startup guy. Like, I liked building profitable companies and bootstrapping and, you know, just doing a good day's work and letting the work speak for itself kind of thing. And so I'm, you know, I was kind of looking at, like, you know, here's a great software company. We can grow it and earn five times our money, and, you know, we can help them. And, you know, and they were looking at bitcoin economies and, you know, asteroid mining and things that were well beyond my skill set. And so I really loved it, learned a lot. But it was probably not the, you know, the best fit for me, but was good to do for a while, and I wouldn't. That was part of my wilderness, right? Just to try different things and to be in these different environments.
Anastasia Koroleva: [00:27:18 - 00:27:23]
When you made this decision to take the VC route, what did you expect?
Dave Hersh: [00:27:23 - 00:28:41]
I expected maybe to be a VC. I was like, well, this made me become my career path. I didn't know and seemed like, all right, well, I've been in this world for a while. I'm good at coaching and supporting entrepreneurs, but I have a family, and I don't want to get back in the 80 hours a week of craziness, traveling all the time, entrepreneurial mode. And I think that's really challenging, right? Is that the age that people often sell their companies coincides with the age where they're becoming more family oriented. In the vedic tradition, they call the householder period of life, that kind of 25 to 50 period where you're. You're no longer the 20 something who is only focused on their own needs. You now have other people to think about, and you're very busy from that front, and so figuring out a way to balance it. I think venture capital tends to be a way that people who have had an exit can or investing in some capacity, and it's a needed resource. Other founders need help from more experienced investors. So I tried it on for size. I just didn't think it fit my personality, but I certainly had a lot of respect for the people who did go that route.
Anastasia Koroleva: [00:28:41 - 00:29:01]
So what it is exactly that made you decide not to go that route? I understand you're more of a kind of startup guy, but I wonder, is it creativity, problem solving, what it is exactly that you missed most during that time?
Dave Hersh: [00:29:02 - 00:33:30]
I, at my core, am someone who has a hard time with the machinery of a larger system. It's where I just see like the mechanisms that can create a lot of pain, right? If you think about the book that I just wrote, it's about helping startups transform because they're stuck. Nine out of ten startups fail, and in the venture model, they make their money on one out of ten startups. And that was just anathema to my values and personality, because there's a lot of blood, sweat and tears in these companies that isn't going anywhere. And I just didn't like those odds. And so I just got in this mode of acquiring stuck startups as experiments to run almost to see how you can transform them, how you can take a company that was a one of a unicorn and turned it into something that's got more lasting value and is sustainable. So I think there was just a personality difference for me. I'm not the shoot the moon, one out of ten is successful, and let's place our bets and make our money that way. I was looking at all these entrepreneurs who were doing that and then failing and feeling bad about themselves. There's like a lot of energy being put towards this rapid scale model that is just not right for every company. So I don't have a problem with venture capital so much as I have a problem with the state of venture capital and how much is being raised and how much it's assumed to be the right path for companies. And so I wrote this book as a means to try to help that waste problem, that a lot of companies just feel like that's the only path they can go down, is to raise venture capital. And you know, if you did and got stuck, that there's no path forward, you just have to liquidate. So the book is intended to help companies who do feel stuck, but is also a way to try to enlighten newer entrepreneurs about the risks involved in trying to grow that quickly and what the psychological blind spots underlying those decisions really look like. And so I'm just trying to lay out the path. Like, here's what happens, here's why it happens. Here's why entrepreneurs who are in that egoic state tend to want to raise money too quickly, try to grow too quickly, and here's how it causes downstream issues. And if you have gotten into that problem, it's okay. There are ways to, if there's a real business under the hood, there are ways to restructure it and find a second act for your business. So my personality was one where, to my financial detriment, I cared deeply about people, very heart driven. And I wanted entrepreneurs to just see a different path and to see what the eddies that they're going to run into would be and how to avoid or recover from those eddies, those ways of getting stuck. And so, yeah, venture capital, I think, was just ultimately maybe not really aligned with my personality and what I cared about, my values, my background. But I do have a lot of respect for the people who do it. And so it's not a thing against venture capital per se. It is problematic in terms of how much is out there. It used to be, when I came into my career early on, it was maybe $8 billion a year in the us of investment. 2021 was like 330 billion. And so it's become the expected path. And it's a bit of a tail wagging the dog problem where people say, okay, we need to go raise a seed, and then we got to get these metrics so we can raise an a, and then we got to get these metrics so we can raise a b, which is just, that's not how you grow a business. The business is like, what do customers need? And what's the real, what's the pull that we're going to feel and how are we going to optimize for changing the world in our small way, and that the money is just in support of that. But I think what happened over the last 2025 years is that the money became the leader. The money was in the driver's seat as opposed to strategy and purpose. That was the thing that I had issues with and sought in my own tiny way to try to support.
Anastasia Koroleva: [00:33:30 - 00:33:34]
So what did you do after you left VC?
Dave Hersh: [00:33:34 - 00:35:52]
I did that regressive reversion thing I talked about before I start the company again. Yeah, I made all the mistakes so that your listeners and other people I talk to can avoid them. Yes. I was like, I don't know what to do. I'm going to start a company. I literally gave myself a timer. I think I even publicly put it out there, which is like, I'm going to figure out a company to start within 60 days. And I did that, but that was probably not the best thing to do. Looking back and, you know, it was a nice experience. It was a year and, you know, it was clear it wasn't going anywhere. It was a bit of a science experiment, technology wise, and it was, you know, just too early for what the market was ready for. And so. So I tried to pivot it and do a few things, but it just was crushing me trying to figure out what to do and how to save the team. And I have a hero complex, so I'm constantly trying to figure out how to save things, which is something I had to reconcile through these experiences. And so. But we sold it to another company, more of an acqui hire type scenario, and then that company got sold. So it actually ultimately made money for the investors, probably, you know, equivalent to a t bill, but didn't make money when all was said and done. So at least there was that. But I tried it, and I needed to do that. I think was like, do I still have it in me? Like, the venture didn't work, investing doesn't work. I'm existentially in pain and don't know what to do. And I had to do something. I had to create movement in some way. And so it was good and I got to hang out with friends and try something. And, you know, it could have worked. But I think through that, I realized this is not my path to just start things from scratch again and to try to go that VC route. It didn't feel right and my heart wasn't in it in the same way that it was the first time around. So that was the point at which I started looking at acquiring these businesses, businesses that had been chewed up and spit out by the financial ecosystem, but still had something underneath that was of value. And that led me on my current path.
Anastasia Koroleva: [00:35:52 - 00:35:59]
What do you mean exactly when you say that? We chewed on and spat out, meaning.
Dave Hersh: [00:35:59 - 00:36:55]
Investors come in and make an investment with a particular thesis, a strategic thesis about a company that it's going to go after this market. And the data shows us that it has a high likelihood of succeeding and disrupting this space. You know, we're going to invest in that hypothesis. And so they push really hard for growth and, you know, weaknesses are exposed in that process, and it doesn't hit the growth numbers, and the market doesn't play out the way expected. And so these companies oftentimes, you know, it just doesn't work, and the company's not meant to be. Right. There's nothing. There's nothing there. There's no core. And the book talks a lot about, you know, really understanding what the core of a business is, because that is the source of whether you can succeed or fail is understanding your core. And it's hard to do in the moment, but so vitally important to the success of the company.
Anastasia Koroleva: [00:36:55 - 00:36:57]
How do you define the core?
Dave Hersh: [00:36:57 - 00:37:02]
For me, the core, and I do have a definition of the book. I probably pull up, but it would. It's the essence of a.
Anastasia Koroleva: [00:37:02 - 00:37:03]
The book is not out.
Dave Hersh: [00:37:03 - 00:37:08]
No, but I do. I do have. Yeah, the, I didn't have the luxury.
Anastasia Koroleva: [00:37:08 - 00:37:11]
To read it so I could ask the advanced copy.
Dave Hersh: [00:37:13 - 00:37:13]
Right.
Anastasia Koroleva: [00:37:13 - 00:37:16]
It's still a month before it's out.
Dave Hersh: [00:37:16 - 00:42:13]
It's April 22. Yeah. These are the advanced copies, and I just did the audiobook around it. Yeah. So it. This is, there's a whole section around reorganizing around your core. So understanding, like, what the core of your business is, and to answer your question, it's really the, it's the essence. What are you, the best in the world at doing? That's really your core. What is it that you do that nobody else can do? And even if it's a tiny market, you know, if there is something you do that your customers could not live without and couldn't find anywhere else, that's a core. And for me to acquire a business, which is, you know, what I do now is saying, really going deep into what is that core and how economically productive is that core? And that's something I can start. I can work around that. But not every business has one. And I think some struggle to find that, or it's too competitive, or they just really never get it off the ground, or the fundamental economics don't work, it's not profitable to do what they're doing. But if there is something that your customers can't live without and they're willing to pay in a way that is productive for you economically, that's a core business. And so what I help to do in a lot of these companies is because what happens is the core gets obfuscated and covered by a lot of bad decisions around scale. Right. There's such a push for growth. And what happens is that the founders and leaders try to make the company look more advanced or further along than it is in board meetings. It was a bit of form of theater to say that this is what our business is and we're growing at this rate. But that disconnect between what the board is pushing forward and where the company really is creates a false narrative that forces bad decision making in the companies. In other words, you may be really good at selling your service to automotive companies, but so that's your core, and they love you for what you do, but in order to grow, you quickly expanded into manufacturing and, you know, some healthcare companies and, you know, but you're not as good at those. But when you're presenting the picture to the board, you're not really showing it in such a way where they understand the nature of what you're the best in the world at. It is more seen on the macro scale of, you know, the numbers. So it's kind of a showing this peanut butter, you know, picture of what a company is and what the numbers are because they want to advance more quickly than the reality of what's going on versus if you just said no, we're going to take the next two years, we're going to really crush automotive, and we're not going to grow as fast as you like. However, in doing that well, we're going to establish a beachhead market that is going to allow us to really move into adjacent markets in a more powerful way. But if you do that too quickly, you're just going to muddy the waters. And that initial beachhead market is not going to be as happy as they could have been, and they're not going to support you, and they may churn more quickly. I think that's what happens for a lot of these companies is what I see. There's a story in the book that I talk about a company called simply measured out of Seattle, and amazing entrepreneurs. They built a spreadsheet, this is back in 2010, so they built a spreadsheet because they were spreadsheet geeks for helping marketers understand their Twitter, basically their tweets. So what are the marketing analytics behind tweets and for connecting with other people out there and really understanding the conversion rates and that sort of thing around Twitter, it was a really amazing spreadsheet. And they did, they were doing 600k in revenue before they took a dime of financing. And I was involved in their seed round and they kept doing that. And then before they knew it, the investors came along and then they raised 8 million to go try to do it on a larger scale. And then, you know, then they raised 20 million, like a year later. And suddenly, when they were this really productive team of five salespeople who were doing great job selling a more advanced version of that original spreadsheet, it was awesome. When there were 20 salespeople trying to sell this marketing analytics platform to, you know, to the market and competing against much larger companies, suddenly it was not. That's strong a company, as you can imagine. Right. And if you unpacked, if you actually peeled away that company and what they were showing to the board, you'd probably know what you'd find, like what's really selling.
Anastasia Koroleva: [00:42:13 - 00:42:14]
Yeah, so the.
Dave Hersh: [00:42:14 - 00:43:05]
It's the spreadsheet, right. It was still, their core was still that thing that they created originally. It's still this, like, spreadsheet that was tracking tweets, and yet there was this, like, complex story around it of, you know, social media analytics and marketing analytics, and that's where it obviously started to stumble. And eventually the company was sold in a less than ideal transaction. But that happens a lot where there's the heart of a business, which is the thing that they are really the best in the world at doing, but the growth imperative forces them to try to expand beyond that too quickly without really harvesting that strength in a way that's going to create long term health for the business. So if you can walk for a long time before you think about sprinting, that's the best path.
Anastasia Koroleva: [00:43:05 - 00:43:22]
So when you acquire those companies, do I understand you correctly, that you look for those that have this core, but that core is hidden by all these bad decisions and unnecessary features and all that stuff, and then you strip them down to their core, is that your strategy?
Dave Hersh: [00:43:23 - 00:46:19]
Yeah, yeah, absolutely. You know, there's usually got to be a play to run, right? And if it's a case where they try to go too big too quickly and they're just overcapitalized and unprofitable, then you're shrinking it down to a place where the company's putting more cash in the business, you know, through operations. And that is like a pressure release valve for the team. Now, you have to let some of the team go, obviously, and you have to restructure things. But what happens afterwards? It doesn't take too long to get to a place where people just feel like they're putting points on the board, they feel like they're winning again. And to be a profitable business is a sigh of relief. And it opens up time and space to thoughtfully experiment with growth as opposed to feeling the push of, you gotta grow now, otherwise, we're gonna cut you loose, and that's a. That's a much better place for a company to be. And then you can start feeling the pull of the market, as opposed to pushing on the market something that they don't necessarily need because you're frantically trying to grow. So that's definitely part of it for me, you know, is figuring out what is the core here, and how do we optimize around that core and then thoughtfully experiment over time with growth. And once you understand the pull, then you can finance the business accordingly. It doesn't have to be venture. You know, it could be debt. It could be acquiring another business that's complementary. It could just be continuing to grow at, you know, 25% a year, you know, within your core market. But you're not forcing it. You're letting the business breathe, and you're letting it find its ideal destiny in the world, and you have the time and space to do that. And in a way where everybody can win, you know, where everybody can to get paid at the end of the day and hopefully enjoy the ride. And so it's. Yeah, it's what I do is, you know, take these wannabe unicorns and turn them into businesses that Warren Buffett could appreciate, you know, that have. That are streamlined around their core. They're healthy, they're purpose driven, they're disciplined, they have strong cultures, and where people feel good about their success. It feels really good. When you have a core, when you are the best in the world at something that's good, that feels really good. And even if the market you're serving is small, those are wins, right, versus a company that's frantically trying to succeed on a lot of fronts and failing at it just doesn't feel good. It doesn't feel good for anybody, and they're stretched too thin, and people don't like to lose, and that can be tough. And it's rare to find that 10% company that does have a tiger by the tail and just literally can't stop growing. It does happen. But for the other 90% of us who aren't in that rarefied air, of those 10%, how do you build a business that matters, and what does it actually look like, and what's the real path?
Anastasia Koroleva: [00:46:19 - 00:46:26]
So how much of your time and effort do you spend on those companies? How involved are you?
Dave Hersh: [00:46:26 - 00:47:42]
Well, right now, I'm selling off the older ones that I had. I did a number of them just on my own. They were smaller and relatively experimental. And then a couple of years ago, I teamed up with a guy named Bob Tinker, who was like me, who founded a company called Mobileiron and took it public. And now we're starting to look at companies that are slightly larger. We don't have a fund. We just try to optimize for our happiness and the stuff that we love working on. So I'm now starting to look around for another buyout, and it would be my background is software companies. And so it's companies in the five to 20 million revenue range that just need a new lease on life that they're overcapitalized, not structured in the right way, have been pursuing the wrong strategy and where I can help them find a better path and, you know, where there's a good purpose behind what they're doing. So right now, you know, getting the book out there and starting to do more speaking and consulting around the book is probably half time, and then the other half is looking for companies and then working with those companies. So I would act as chairman on any company that I acquired, which means I spend, you know, a healthy portion of my time rolling up the sleeves and helping them. But it's not a full time job. So, yeah, call it half and half.
Anastasia Koroleva: [00:47:42 - 00:47:44]
It's one company at a time for you.
Dave Hersh: [00:47:44 - 00:48:33]
Yeah, maybe two, because, but, yeah, I do one, and then at least that first year, you're spending a lot of time with them, and then it maybe starts to level out a little bit as things, you know, get more, you know, solidly in place. And you could maybe take on another project, but I wouldn't do too many. And, you know, again, yeah, you want to be really heavily involved. And I think for me, even writing the books and doing that kind of thing, it's good for me to keep a foot in the real world of business so I don't feel too removed from it. You know, I think it could be easy for me to be, you know, just kind of drift into the ether of ideas, and I don't want that. I really want to make sure I maintain healthy connection to what it's really like and, and how it's changing, because it is changing pretty dramatically right now.
Anastasia Koroleva: [00:48:33 - 00:48:35]
So what made you think of writing a book?
Dave Hersh: [00:48:35 - 00:49:50]
I've always wanted to. I love writing. There was a point after the.com collapse, and I was kind of struggling to figure out what was next. I got into USC for screenwriting. I was going to go get my MFA in screenwriting just because I love the idea of storytelling. I just loved, you know, the art of storytelling. And I was always drawn to it. And then maybe it was 2017, like that or something. I was at a. It was New Year's Eve, and I was with my kids, and we were talking about New Year's resolutions, and I said, I wouldn't want to write a book. I'm gonna write a book. And I was like, once I did that, once I said that in front of my kids, I was like, I can't go back on that. It was like, the best accountability. It's like, you know, I want them to see me doing the thing I said I would do. Honestly, they probably did not even remember. They had no idea they did that. But in my mind, I was like, I told my kids I was gonna write a book. I'm gonna write a book. I'm gonna do this thing. And so that helped. And I just love doing it. You know, it was like waking up in early on weekend mornings, you know, and cranking out content. It just. It was fun for me. I don't know why. It was a weird, weird thing. But once I got into the process, I really enjoyed it, you know? Now starting to sketch out book number two.
Anastasia Koroleva: [00:49:50 - 00:49:53]
How long did it take you to write a book?
Dave Hersh: [00:49:53 - 00:50:41]
It's probably five years, because I hadn't done it before. Yeah, I know. It was a long time. Plus, I was CEO of different companies, and I was very busy during the day. And so it was a combination of, I hadn't written a book before, and so the first drafts were terrible, and I had to keep, you know, cranking out that way. There wasn't really a, you know, any specific milestone of got to get it out there on this timeframe, pushing me. And so I think those combinations. So when I let go of the CEO jobs that I had in the companies that I was coming in, because when I buy them, I'd come in as CEO for a while, just during the cleanup process, and once I didn't have any of those, I was able to dedicate more time and space to wrapping it all up and finally getting it to a place where I could get it out there.
Anastasia Koroleva: [00:50:41 - 00:50:49]
So, Dave, on a personal level, how do you define success today, comparing to how you defined it when you just started jive?
Dave Hersh: [00:50:49 - 00:51:02]
All right, I'll start with the simple answer. The simple answer is, it used to be based on what others thought, and now it comes from within. And that, to me, is the essence of all of this stuff. It's an easy thing to say. Very hard to feel.
Anastasia Koroleva: [00:51:03 - 00:51:04]
Yeah.
Dave Hersh: [00:51:04 - 00:52:11]
It takes a long time to truly feel sovereign, right. Where all of the happiness I need all of the, you know, feelings of I'm good enough, and I'm doing everything in a beautiful way in the world. For that to surface from within takes a lot of work, you know, easy idea, hard feeling to truly feel. So I think that's what's changed for me. And I know that if the work I do is coming from a more soulful place, is coming from that thing that is uniquely me and is helping people, and I can feel the way I'm serving the world. I can feel that from other people. And that's, you know, then I'm that success. I couldn't think of anything else. Right. It's just, that's why I'm on this planet. If I'm doing what I'm on this planet to do, and I can feel that it is touching the people around me and meaningful ways kind of all there is.
Anastasia Koroleva: [00:52:11 - 00:52:13]
And that motivates you enough.
Dave Hersh: [00:52:13 - 00:53:00]
Like, way beyond what money or fame or, you know, anything else would have motivated me for before. Like, it's. Again, it's an inexhaustible fuel source. Right. It's your soul. You know, my next book is called right now called the Eros advantage. And Eros is human desire, that thing that propels us forward in life. And so when you are propelled forward by something so deep within you that it's not even a choice, it just. It's happening naturally. Once you tap into that deeper fuel source, all the rest of that noise goes away, and a lot of that pain and insecurity and doubt and thrashing just starts to go away. So it. It feels very different.
Anastasia Koroleva: [00:53:00 - 00:53:08]
Yeah. They seem so small that they're irrelevant when you're pulled somewhere that. That way. I know exactly what you're talking about.
Dave Hersh: [00:53:08 - 00:54:26]
Yeah. And you still have things like money, stress, or, you know, that. Like, you know, making payroll or what. You know, like, those things still are stressful, but in a very different way. Like, you just kind of see it for what it is. And I think that, to me, is the downslope of this post exit founder conundrum. You know, there's this. The upslope is the, like, the thrashing and the kind of, I got to do another company or I gotta make more money, and I'm this person in the world, and now I got to advance my brand, and it's like all this kind of egoic thrashing and pain that you got to go through. But the downslope is going, oh, that's all B's. There is no. The ego is just lying. It's just a. It's like an evolutionary quirk that made humans the way we are, but it's not true. It's not real. You know, my essence is not CEO guy that everybody knows. My happiness is not dependent on people seeing me that way. And so when you get on the downslope and you start to tap into that deeper fuel source, everything goes away, and it just starts to feel so much better. I never question the success anymore. I'm just doing what I'm meant to do on this planet. And then every day it's like chopping wood, you know, I'm doing that thing, and the voices have gone away.
Anastasia Koroleva: [00:54:26 - 00:54:32]
So you're thinking about money and wealth. How has that changed over time?
Dave Hersh: [00:54:32 - 00:57:48]
Yeah, I mean, it changed pretty substantially, you know, where. Whereas before I saw it as the metric that defined success and how well I was doing in the world, now I just see it as energy. It's just a form of energy that can be moved through the world in ways that can support the thriving of the people you come in contact with. And I think that there's something there for companies. I think there's a future state where companies learn a little bit more about how to use equity and wealth creation and money as an energetic resource that supports the collective thriving of the people involved, as opposed to wealth in the hands of a few who then become powerful people and, you know, use that money for their own ego purposes or, you know, other things. I just think that time is over, like it. And so a lot of this work, and again, that downslope period is saying, if I'm taking care of my family and all of the basic needs, I don't need that much. And so how do I reimagine wealth and money as a means to support more people being on this journey of feeling alive and feeling connected? And how do we reimagine the idea of what a company is not as just a means of making a few people wealthy, but as a system of human growth? How do we reimagine the idea of how a company can support collective well being for its people as well as the planet? And we're starting to see the early signals of companies like Patagonia and others that are doing really interesting things along those lines. So I think it's a thread that I'd like to keep following, is what is the future? And that's what the next book's kind of about, in a way, is what is the future of humans in what's the future of companies as it relates to humans. As AI takes over the means of production jobs, you know, we're no longer like people, just processing data and information that's being done by other systems that humans have to elevate to what humans are good at, which is empathy and connection and curiosity and love. Right. And these things that imagination and creativity, like, that's what humans are going to be needed for in the future. So we kind of have to reimagine what companies look like and how you support collections of people who are more human and not just, you know, tools to process information, but, you know, systems of people with, you know, beliefs and identities and souls who want to live better lives. And I think it's a unique opportunity that we have as AI starts to do more of the actual work to reimagine how humans are going to be in these companies. I find that whole area of subject matter fascinating, and that's what I want the next book to be about just for my own purposes of learning about it. And hopefully it's helpful to a few people out there.
Anastasia Koroleva: [00:57:48 - 00:58:12]
I think it's very needed. I think technology is way ahead of our understanding of our, our own psychology of nature. I think we need more philosophers and psychologists right now than anybody else to help us figure out how to live in this new world with AI, or we should all become more educated spiritually and psychologically.
Dave Hersh: [00:58:12 - 00:58:33]
I agree wholeheartedly. My father was a philosophy professor. He's retired now, but he's been helping me with the book. It's been really fun to work with him on it. So getting, digging into Jung and depth psychology and, you know, philosophy as a. As the kind of color commentary for understanding what the future of businesses look like. So, yeah, couldn't agree more.
Anastasia Koroleva: [00:58:33 - 00:58:37]
How do you choose people you surround yourself with?
Dave Hersh: [00:58:37 - 01:01:18]
Yeah, it's a good question. It kind of changed as I. As my, as I. As I crested that, you know, midlife, painful post exit, you know, difficult period, and immersed myself in a lot more inner work to just ground myself in me, that the people I surrounded myself with changed a bit just naturally, you know, that you're doing more work with these people, and if you start to show up as a vulnerable, open, loving, empathetic, kind, curious version of yourself, you start to attract people into your orbit who have similar ways of being. And there are also a surprising amount of people, you know, it's not relegated to the land of hippies anymore that, you know, there's a lot of people in very powerful positions that I've been doing this inner work with who are changing the world in strong ways. They're also starting to do more of this work. And, you know, that's hardening to me that there's more of that. And so, yeah, but it's not like I just around myself with people who are successful or doing that. I surround myself with the people who are soulful, who are trying to do the work and show up in the fullest version of themselves possible. And, you know, but the interesting thing is, it's not like I eschew my old friends or say, well, they don't get it, and I'm not going to hang out with them anymore because I've gone through this change. What happened, interestingly enough, is that a lot of the people who maybe hadn't done as much inner work but I had been friends with for a longer period of time started to come to me as to help them through that process. They saw what happened to me and I became this conduit for them to get past the pain and to find inner work that connected with where they were in life and what they needed. You know, it's like the old me would have been like, you know, it's a no asshole rule, and I don't work with assholes, you know, and, like, the new me, I think, would be like, well, why are they an asshole? What's going on? You know, what's happening to them? And can I help? Like, is there, you know, something going on there? So, yeah, I would say I choose to spend time with people who at least where there's motivation to be the best they can be and even if they're earlier in that journey. Okay. You know, I love that. Yeah. So anybody who feels like they're on the path is, you know, where I spend a lot of time. And the tribe that has come into my orbit as a result of doing all this work has been nothing short of amazing.
Anastasia Koroleva: [01:01:18 - 01:01:19]
Yeah.
Dave Hersh: [01:01:19 - 01:02:04]
You know, whereas before, when I was in that egoic, you know, entrepreneur state, I pushed people away because I was, you know, frankly, probably hard to be around. And I was, you know, focused on my own success and, you know, winning and all these things that were programmed to think are important early on and that pushed people away once they kind of ripped it all apart. And I showed up as an open, vulnerable, you know, broken down version of myself. And when I say broken down, I mean in a good way, spiritually kind of taken down to the studs when I showed up in that way that the tribe showed up. They were there all along, I think. But I was able to connect with them for the first time. You know, in a way, that was really me.
Anastasia Koroleva: [01:02:04 - 01:02:34]
Yeah. Because essentially what you. The process you're describing, what you did to yourself is not that different from what you're doing to those companies. You. You found your own core, you understood your own core. You cleared out all the junk. Right. And then you're rebuilding from that core, but based on completely different principles. Right. So I can see how your business activity now is much more aligned with your personality and your level of understanding of who you are comparing to before.
Dave Hersh: [01:02:34 - 01:03:12]
That's exactly right. You nailed it. And I, you know, I talk about that in the talk. I said, like, the company transformation is very similar to personal transformation. So what you said is much more brilliant way than I could have put it. Brilliant ways to put it than I could have. But it's that same thing. Yeah. It's like there is an essence to you. There is a thing that was there when you were five years old that's still there. And if you can, you know, whittle away all of this clothing and baggage and barnacles and plaque that got in the way of that essential self and get back to what is uniquely you, what you are the best in the world. That is a person. That's right. It's the same process.
Anastasia Koroleva: [01:03:12 - 01:03:44]
Absolutely. And I actually really love the trend that we are watching now. This creator economy, when people are given so much of themselves to the world and they see themselves as the products they can give to the world, because those who do it really well, it always comes from this place of understanding and accepting themselves as these unique beings. Because you're totally right. We're always the best in the world of being us. Right? There's no competition.
Dave Hersh: [01:03:45 - 01:03:46]
Yeah, exactly.
Anastasia Koroleva: [01:03:46 - 01:03:55]
And it's beautiful to watch people and finding that place and liberating themselves from all the junk of expectations from other.
Dave Hersh: [01:03:55 - 01:04:32]
People, it's a really good way of putting it. And, you know, there's a shadow side to those creators, obviously. But I hope that, you know, this next generation, you know, my kids generation, I just feel like they're growing and learning at a much faster clip than we could. You know, they're obviously prey to a lot of difficult things like social media and, you know, comparison and, you know, and the anxiety and mental health issues are going way up. But I do hope that it's maybe breaking them down faster so that they can emerge more whole and sovereign quicker than our generation did. I hope. Yeah.
Anastasia Koroleva: [01:04:32 - 01:04:51]
But if you look at the millennials, which is basically the generation between us and our kids, despite all the criticism that generation is getting, I find them much more spiritually mature than our generation or the generation before us. So I think the trend is actually quite, quite good, quite hopeful.
Dave Hersh: [01:04:52 - 01:05:35]
I'm very, oh, very much so. Yeah, me too. No, I agree wholeheartedly. I've written the first chapter of the next book, and I talk about the, I have, like a Maslow hierarchy of work motivations, and you can kind of see from the greatest generation up until Gen Z how our reasons for going to work and what we got from them have advanced along this continuum that is taking us to a much more soulful place. And so I'm definitely, you know, a fan of, you know, how more advanced younger generations are in spiritual understanding and, you know, the state of the planet and the world and. And so, yeah, I agree. And look forward to seeing how it all plays out.
Anastasia Koroleva: [01:05:35 - 01:05:43]
Exactly. Let's hope that all the promises for longevity also play out in our favor. Yes, we've long enough to see all these generations.
Dave Hersh: [01:05:43 - 01:05:51]
Yeah, exactly. Now that we've destroyed the planet for them, maybe they can help us live longer to see it recover between AI and our kids.
Anastasia Koroleva: [01:05:51 - 01:05:52]
Maybe they'll figure it out somehow.
Dave Hersh: [01:05:52 - 01:05:54]
Yes, exactly.
Anastasia Koroleva: [01:05:54 - 01:05:58]
So, Dave, a perfectly fulfilled feeling life, what is it for you?
Dave Hersh: [01:05:58 - 01:07:26]
I think it's just kind of what we've been talking about, where it's, if I am whole to the point where all of what I need can come from within, that allows me to be back in the world in a way where I feel like I can give up my gifts, where I feel like I'm connecting and feeling alive. Like, to me, that's it. It's just that feeling of being alive. And it's not, you know, pushing away negative emotions or anything, like, it's being there for all of it. The Charlotte Djoko Beck, the Zen philosopher writer, said that happiness has an opposite and joy doesn't. Meaning if you're seeking happiness, you're trying to push something away, but when you're seeking joy, you're just alive in all of it. And I think for me, that's fulfillment, is that every day I feel alive, I feel fully in life. And that may include a lot of tears and anger and shame and other things, but I'm witnessing all of it. I'm moving it through, and you're just present and there for all of it. It makes everything better. The colors are brighter, the intimacy is better, the food tastes better. It's just like everything is better and more alive when you're in that state of being. And so I think that's what I seek and try to model as best I can.
Anastasia Koroleva: [01:07:26 - 01:07:33]
So may I ask you, if you have to rate your fulfillment on a scale from zero to ten, where are you at?
Dave Hersh: [01:07:33 - 01:07:40]
Oh, maybe I'm eight.
Anastasia Koroleva: [01:07:40 - 01:07:43]
Okay, that's very fine. Especially.
Dave Hersh: [01:07:43 - 01:08:18]
Yeah, like, I still have room. Yeah. There's still things I know I need to work on. I'm. I'm not as enlightened and in that. That kind of sovereign space as I know I could be. But the, like, how far I've come in the last five years has been so wonderful for me. Just feels so different now that, you know, I don't have those voice in the head, pain, anxiety anymore. So I feel like I've come a long way, and I hope that I never get to ten, because then if you get to ten, you're just saying, like, you know, maybe you die at that point.
Anastasia Koroleva: [01:08:18 - 01:08:19]
You're dead. Yeah.
Dave Hersh: [01:08:20 - 01:08:32]
Yeah. Like, if you're truly actualized, it's just you can die, right. And you can never stop growing. So I don't think I'll ever get there, but if I can maintain eight to nine, I think I'm doing pretty well.
Anastasia Koroleva: [01:08:32 - 01:08:41]
Brilliant. So if you talk to someone who sold their company recently, within the last two, three years, what would you tell them? What's your advice?
Dave Hersh: [01:08:41 - 01:09:11]
It's so subjective because I got to know the person and I often don't give advice. I really just, you know, unless they ask for it. The Zen tradition, they say people have to ask for advice three times before you get. So I really just kind of sit with them and, you know, if they ask for experiences that I've had, things like that. But if I were to broadly say or kind of give advice to myself when I was in that phase, it would just be, do the work. Just throw yourself at the work.
Anastasia Koroleva: [01:09:11 - 01:09:13]
But the internal work of understanding yourself.
Dave Hersh: [01:09:14 - 01:09:44]
Yeah, the inner work. Yeah, sorry, sorry, yeah. Do the inner work. And whatever modality you are drawn to and what that will hopefully do is open up the door for more and so that you desire more and you see that inner work is a constant, that it makes everything better. And maybe, I think in my life, it's probably 15% of what I do is somehow related to some form of inner work.
Anastasia Koroleva: [01:09:44 - 01:09:54]
You're writing a book I made. When would give you a structure to do that inner work? And maybe that's why you also enjoy it so much. Because you enjoy doing that inner work.
Dave Hersh: [01:09:54 - 01:09:55]
Yep, for sure.
Anastasia Koroleva: [01:09:55 - 01:09:57]
So. So what keeps you up at night?
Dave Hersh: [01:09:57 - 01:10:52]
My dog getting too hot? Yeah, I think that's you know, I don't have as much of that anymore. You know, I still like, we'll get the financial stress, you know, that lizard brain, middle of the night thing where you get little problems that seem like they're really big in the middle of the night, but, yeah, to a much lesser extent than I used to. There's nothing, you know, I went through a divorce, you know, the last couple years, and that's obviously traumatic and can, you know, cause a lot of deep pain. It was, you know, very hard for me, and, you know, those. Those are just gut wrenching things, and you have to kind of go through it, not around it. So, you know, life does throw things your way that do force a lot of pain. And so I think it's really just about how you deal with that pain now that changes.
Anastasia Koroleva: [01:10:52 - 01:11:08]
Yeah, I had the divorce, too, so I can very much relate to it, and I feel lots of empathy for you. But I also think, like, an exit, if you process it properly, as if you go through it exactly as you said, you always come out a better person.
Dave Hersh: [01:11:08 - 01:11:24]
Yeah, exactly. And you got to use that opportunity to do that. And I did. I mean, the last couple of years that I've gone through with that, like, I've been the most transformative I've ever been through, you know, by a factor of ten. So I will take the gifts that come with those life changes.
Anastasia Koroleva: [01:11:24 - 01:11:30]
It's that kind of suffering that brings joy at the end. Somehow we just don't know how when we go through it.
Dave Hersh: [01:11:30 - 01:11:31]
Yeah.
Anastasia Koroleva: [01:11:33 - 01:11:42]
Okay. I think my last question has been such an amazing conversation, and thank you so much for opening up and going so deep. And my last question is, how do.
Dave Hersh: [01:11:42 - 01:12:10]
You want to be remembered as someone who saw the deeper side of what was going on? Someone could see under the hood and help people as a result. So, to me, that's always been the thing that I feel most drawn to, is, you know, what's going on under the surface, and how do we use that awareness to change what's above the surface?
Anastasia Koroleva: [01:12:10 - 01:12:23]
Brilliant. Dave, you obviously have so much to give and so much to share, and I really can't wait for your book to be published so I can read it and hopefully we can discuss it at some point. I would love that.
Dave Hersh: [01:12:23 - 01:12:29]
Great. I would love that, too. Thank you so much for having me today. And asking all these awesome questions is really fun and cathartic.
