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Podcast Notes: Exit Paradox - Episode with Dave Hersh
Episode Overview Host: Anastasia Koroleva Guest: Dave Hersh Title: Post-Exit Rebirth: Finding Self, Sovereignty, and Inexhaustible Fuel Sources Release Date: [Insert Release Date] Duration: [Insert Duration]
In this episode, Dave Hersh, a seasoned entrepreneur who sold his company Jive through an IPO 13 years ago, shares insights into life after a major exit, discussing his decade-long journey of personal transformation, identity crisis, and rediscovering purpose.
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Key Themes and Discussions
- Life After Selling the Company
- Initial Experience:
- Transitioning from CEO to chairman brought initial relief but later confusion as identity was lost.
- Faced existential questions about self-identity and purpose post-exit.
- Challenges:
- The emotional turmoil of losing the title and responsibilities of being a CEO.
- The pressure to redefine one’s existence outside of the company.
- The Existential Crisis
- 10-Year Journey:
- Dave describes it as a "deep reprogramming" and "rebirth," focusing on inner work.
- Emphasizes the importance of understanding one’s identity beyond entrepreneurial achievements.
- Inner Work and Transformation:
- Utilized methods like the Hoffman Process for deeper self-exploration.
- Discussed the struggle to balance ego and self-worth with the need for inner peace.
- Entrepreneurial Identity and Re-invention
- Identity Reconstruction:
- Highlighted the difficulty entrepreneurs face in detaching from their business identities.
- Acknowledges common pitfalls of trying to recreate past successes without personal growth.
- Finding Clarity:
- Describes how clarity often emerges through persistent inner work and acceptance of the liminal space between one's past and future selves.
- Transition to Venture Capital and Beyond
- Venture Capital Experience:
- Worked at Andreessen Horowitz but felt it didn’t suit his personality or values.
- Explored how venture capital often prioritizes rapid growth over sustainable practices.
- Transformative Business Practices:
- Advocates for acquiring and restructuring businesses to focus on their core strengths instead of broad, unsustainable growth.
- Current Philosophies on Success and Wealth
- Redefining Success:
- Success is now based on internal fulfillment rather than external validation.
- Emphasizes the importance of soulful work that nurtures both the individual and the community.
- Wealth as Energy:
- Views money as a resource that should support collective growth rather than individual enrichment.
- Encourages a shift in how businesses approach wealth and its distribution.
- Future Aspirations and Advice
- Next Generation of Entrepreneurs:
- Expresses optimism for the future, particularly regarding younger generations' spiritual maturity and awareness.
- Aims to guide new entrepreneurs in understanding the complexities and emotional aspects of running a business.
- Advice for Exited Entrepreneurs:
- Encourages focusing on inner work and self-discovery.
- Suggests patience in the journey of redefining one’s purpose after an exit.
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Personal Insights and Reflections
- Personal Fulfillment: Dave rates his fulfillment as an 8/10, highlighting ongoing growth and the importance of continuous inner work. He appreciates the journey of emotional depth and the richness it brings to life.
- Legacy and Remembrance: Wishes to be remembered as someone who understood the deeper elements of human experience and helped others navigate their paths effectively.
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Resources Mentioned
- Book: *Reignition* by Dave Hersh - [Amazon Link](https://www.amazon.com/Reignition-Transforming-Startups-Breakout-Winners/dp/1639090347)
- Website: [davehersh.com](https://www.davehersh.com/)
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Conclusion This episode of Exit Paradox delves into the profound inner transformations that occur after major career transitions, particularly in the entrepreneurial space. Dave Hersh's candid reflections on identity, purpose, and the meaning of success provide valuable insights for entrepreneurs navigating their post-exit journeys.
For listeners, the key takeaway is the importance of inner work in achieving true fulfillment and the necessity of redefining personal success and wealth in meaningful ways.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:25Dave Hirsch. He sold his company through an IPO 13 years ago, then spent several years with the VC firm Andresin Horowitz. These days, Dave is more fulfilled and productive than ever. He credits a 10-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. 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.
1:07The upslope is like the thrashing and the kind of, I got to do another company or I got to 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 BS. 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.
1:37Hello, David. Hey, how's it going? Very well. Very happy that you are joining me today. Thank you so much. Absolutely. Happy to be here. Really looking forward to digging into your life quite deep today. I hope you're ready. Always. 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? Yeah, that's right. 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.
2:21So 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 was 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.
3:12right thankfully you know what had happened was the company was uh originally an open source product that my two co-founders had developed and had a pretty big following and it was essentially threaded discussion so discussion forums and this was circa 2001 obviously and that was still a popular form of uh communication and collaboration on the internet so 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 of years and continued to grow the business there.
3:50Then 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. You know, it was 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. And 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.
4:35And 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 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 and over the next several years built up a new business essentially selling large companies on social collaboration technology and went you know probably zero to 55 60 million over the next three years uh which was obviously you know a tremendous ramp and kind of took it out of me as i'm sure you know a lot of your listeners would understand like that's that period of massive scale that is simultaneously wonderful and beautiful, but really can destroy you personally too.
5:39And it was at 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.
6:28And I went through so much. I really hope that my experience could be helpful to your listeners because there are stages and there are, you know, 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 and the challenges that I had in my own journey. I can't wait to find out all of it. So where do you start? The moment you were no longer a founder and CEO in your case, how did it feel? 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, you know, ripping a Band-Aid off and suddenly your identity is gone and you're no longer in the ebbs and flows.
7:34of 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 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.
8:27So I think it's, yeah, relieving for a little while and then the big questions start to emerge. 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 yeah so this is part of the challenge of the long run as that the the longer term journey is one where you recognize that all of these egoic conditions around you are false right All of 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. So that's kind of jumping to the conclusion.
9:16But 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 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.
10:13But the loss of a company 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, you know, in their 20s and 30s start to become the baggage that creates a lot of pain later, especially after you've had an economic event like that.
10:59So for me, I think the original question was, you know, what did I do? You know, so it started maybe the gateway for me was doing a thing called the Hoffman process, which is a popular. Yeah. Would you explain it to those who haven't experienced it? 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? Why am I this complex set of patterns?
11:45We do so much in life that is subconscious that just happens because it's, it's been programmed into us and we don't realize it. We think, oh, 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 and 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.
12:27And 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 a 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, you know, deep kind of break the horse down transformation that allows them to see the whole self as a complex system of patterns and processes.
13:29And that's what is keeping people stuck in the eddies of life, as opposed to flowing down the river and being happy to 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 gateway to doing a lot of other inner work that was meant to dismantle that egoic baggage that was keeping me stuck in pain. Amazing. Okay. So that was the gateway. What else did you do that was helpful or not helpful? Yeah. So, you know, I did do talk therapy throughout.
14:10There 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. The martial arts. Okay. Yeah. The belts were getting darker.
14:59Put 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 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 to 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 yeah absolutely 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 a that's an exhaustible fuel source right that can wear us out uh and you know as you've seen it can drive people into um you know states of depression or anxiety and um you know alcohol abuse there's all kinds of things that will come if you don't reconcile with it.
16:26And 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 our accomplishment helped me connect with. And that was a series of week-long intensives and a 10-week course called Masterclass that took place over you know, 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, in a beautiful way.
17:29So 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, you know, real transformation work, you say, well, I'm going to be a CEO again, I'm going to go do that thing again, that served me before.
18:17Yeah, 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 I 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.
18:53I'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 And just 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 yet I do see it happen a lot where that's the pattern. Uh-huh. So how long do you think it took you before you got to some point of clarity about what it is you really wanted to do or the direction you wanted to go in? You know, I think it was 10 years of struggle, to be honest.
19:47Yeah, yeah. You know, there were moments. I think there's a lot from people who exited more than 10 years ago that they say it's at least 10 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 a week 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. Yeah. they're entrepreneurs so they're very good at storytelling you know 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 yeah so it does different kind of work than what we're used to yeah i mean it's rare that i'd 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 yeah that would be the most enlightened approach.
21:10You 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, uh, which is about the beauty of the liminal, which is, you know, this, this limbo between old self and rebirth of the new self. And as entrepreneurs, we have this desire to fix, to solve, to, you know, come up with a new idea the you know 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 and that rebirth doesn't happen unless you sit in the underworld for a while and you know 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 you know succeeding on this scale who was leading people when you know are no longer in that position there is a long period to celebrate the death of that 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 if you 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.
22:32There'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 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 beautiful liminal space between old you and new you, and that you can't just be reborn.
23:19As much as entrepreneurs are going to be like, okay, now I'm this person, and I'm going to be a VC. I'm going to make investments, and that's going to 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.
23:57And 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.
24:36But 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, you know, 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 of the entrepreneurial mindset so i feel like i've been talking a lot so sorry i hope this is helpful that's the whole idea you should be talking a lot uh that's the whole idea so so i understand that you only had a few months after you left Jive and before you joined Anderson Horowitz.
25:45So when did you find that time and space in your head to do all this hard work? 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 the 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 um 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 uh 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.
26:37It was just kind of filling up space. Uh, I went to entries and Horowitz for a few years shortly thereafter, which was fascinating. And they're really, you know, uh, impressive group of people. And I love 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, uh, 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.
27:12And, 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 and 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. When you made this decision to take the VC route, what did you expect? I expected maybe to be a VC. I was like, well, this may be become my career path. I didn't know and seemed like, all right, well, I've been in this world for a while.
27:49I'm good at coaching and supporting entrepreneurs, but I have a family and I don't want to, you know, 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, um, family oriented, you know, what in the Vedic tradition, they call the householder period of life, that kind of 25 to 50 period where you're, um, you know, you, you're no longer the 20 something who is only focused on their own needs. You know, you now have other people to think about and you're very busy from that front.
28:32And so figuring out a way to balance it, I think venture capital tends to be a way that people who have had exits 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 would fit my personality, but I certainly had a lot of respect for the people who did go that route. 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? Like what it is exactly that you missed most during that time?
29:17I, at my core, am someone who has a hard time with the machinery of a larger system. It's where I just see the mechanisms that can create a lot of pain. Think about the book that I just wrote. It's about helping startups transform because they're stuck. Nine out of ten startups fail. 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 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 wannabe unicorn and turned it into something that's got more lasting value and is sustainable.
30:13So I think there was just a personality difference for me. I, you know, I'm not the shoot the moon. One out of 10 is successful and let's, you know, place our bets and make our money that way. I was like looking at all these entrepreneurs who were doing that and then, you know, failing and feeling bad about themselves. And, you know, 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.
30:53And 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. Here's what happens. Here's why it happens.
31:36Here'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 you know if there's a real business under the hood there are ways to restructure it and and and find a second act for your business so my personality was one where um to my financial detriment i cared deeply about people uh 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.
32:23And 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, you know, in terms of how much is out there. It used to be, you know, when I came into my career early on, it was maybe$8 billion a year in the U.S. of investment. You know, 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.
33:04And 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, you know, what's the pull that we're going to feel? And how are we going to, you know, 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 20, 25 years is that the money became the leader. The money was in the driver's seat as opposed to strategy and purpose. And so that was the thing that I had issues with and sought in my own tiny way to try to support.
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33:47So what did you do after you left VC? I did that regressive reversion thing I talked about before. I just started a company.
33:58yeah i made all the mistakes so that your 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 was like i'm going to figure out a company to start within 60 days um and i did that but that was probably not the best thing to do looking back and uh you know it was a nice experience i it was a year um and you know it was clear it wasn't going anywhere it was a bit of a science experiment uh technology wise and it was you know just too early for what the market was ready for and so i tried to pivot it and do a few things but it just was crushing me uh 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.
34:55And 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. And probably, you know, equivalent to a T-bill, but it 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. It was like, do I still have it in me? Like the venture didn't work. Investing doesn't work. I'm existentially, um, 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.
35:30But, um, you know, I think through that, I realized this is not my path, you know, to just start things from scratch again and to, you know, try to go that, that VC route. Um, 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. Yeah. You know, businesses that had been chewed up and spit out by the financial ecosystem, but still had something underneath that was of value. And yeah, and that kind of led me on my current path. What do you mean exactly when you say there was the true donors spat out?
36:14Meaning 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 the space. And, you know, we're going to invest in that hypothesis. is. 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.
36:54There'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 how do you define the core for me the core and i do have a definition of the book which i should probably pull up but it's the essence of it the book is not out no but i do i do have yeah the uh i didn't have the luxury to read it so i could the advanced copy it's still a month right it's still a month uh before it's out it's april 22nd yeah these are the advanced copies um and i just did the audio book around it yeah um 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 that'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 um is saying really going deep into what is that core and how economically productive is that core.
38:23And that's something I can start, I can work around that, but not every business has one. Right. And I think some struggle to find that, or it's too competitive, or, you know, they just really never get it off the ground or the fundamental economics don't work. It's not profitable, um, to, 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, you know, is productive for you economically, that's a core business. And so what I helped 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?
38:58There'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. There's a bit of form of theater to say that, you know, this is what our business is and we're growing at this rate, but that disconnect between what the board is pushing for 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, you know, selling your service to automotive companies, but so that's your core and they love you for what you do.
39:42But 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.
40:30However, 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. And so 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 you know amazing entrepreneurs like they built a spread this is back in 2010 so they built a spreadsheet because they were spreadsheet geeks for helping marketers understand the um their uh twitter basically their tweets right so what are the the marketing analytics behind you know 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 you know they were doing 600k in revenue before they took a dime of financing and and you know i was involved in their seed round and they just you know they kept you know doing that and then before they knew it the investors came along and then they raised eight 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, you know, doing great job selling a more advanced version of that original spreadsheet.
42:02It 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 strong a company as you can imagine. Right. And if you unpack, 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 yeah so it's the spreadsheet right it was still their core was still that thing that they created originally it was right still this like spreadsheet that was tracking tweets um and yet there was this like complex story around it of of um you know social media analytics and marketing analytics and and uh and that's where it obviously started to stumble and eventually the company was you know, sold in a less than ideal transaction.
42:55But, um, that happens a lot, you know, where there's the heart of a business, which is the thing that they are really the best in the world at doing. Um, but the growth imperative forces them to try to expand beyond that too quickly without really, um, harvesting that strength in a way that's going to create long-term, uh, health for the business. So if you can walk for a long time before you think about sprinting, that's the best path. 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?
43:37Is that your strategy? Yeah. Yeah, absolutely. 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 is 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.
44:14They 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 got to grow now, otherwise we're going to cut you loose. And 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.
44:58And 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 complimentary. It could just be continuing to grow, you know, 25 % a year, um, you know, within your core market. Um, but you're not forcing it. You're letting the business breathe and you're letting it, um, 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 get paid at the end of the day and hopefully enjoy the ride.
45:34And 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.
46:09It doesn't feel good for anybody and they're stretched too thin. And, you know, people don't like to lose and, you know, that can, that can be tough. And it's rare to find, you know, that 10 % company that does, you know, have a tiger by the tail and just literally can't stop growing. It does happen. But for the other 90%, you know, 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? So how much of your time and effort do you spend on those companies? How involved are you? Well, right now I'm selling off the older ones that I had.
46:47I 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 mobile iron and took it public. And now we're starting to look at companies that are slightly larger. Uh, we don't have a fund. We just, you know, uh, try to optimize for our happiness and the stuff that we love working on. So I'm now starting to look around for, uh, another buyout and it would be, you know, my background is software companies. And so it's companies in the five to 20 million, uh, revenue range, um, that just need a new lease on life.
47:20you know, that they're overcapitalized, not structured in the right way, have been pursuing the wrong strategy, um, and where I can help them find a better path and, um, 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, uh, speaking and consulting around the book is probably halftime. And then the other half is, you know, looking for companies and then working with those companies. So I would as chairman on any company that i've acquired uh 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 it's one company at a time for you 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 um you know solidly in place and you could maybe take on another project, but I wouldn't do too many.
48:19Uh, 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, I, 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. Uh, and I don't want that. I really want to make sure I maintain a healthy connection to what it's really like and and how it's changing because it is changing pretty dramatically right now so what made you think of writing a book i've always wanted to um i love writing uh there was a point after the dot-com collapse and i was kind of um struggling to figure out what was next i got into usc for screenwriting i was going to go get my mfa in screenwriting uh just because i love the idea of storytelling i just loved um you know know the art of storytelling and and that 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 revolutions and i said i always want to write a book i want to write a book um 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's like the best accountability it was like you know i want them to see me doing the thing I said I would do.
49:40Honestly, 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 going to write a book. I'm going to write a book. I'm going to do this thing. And so that helped. And I just loved doing it. You know, it was like waking up 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. Once I got into the process, I really enjoyed it. You know, now starting to sketch out book number two. how long did it take you to write the book um 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 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 uh you know any specific milestone of you got to get it out there on this time frame uh 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 you know because when I'd buy them I'd come in as CEO for a while just to you know during the clean-up 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.
50:58So Dave on a personal level how do you define success today comparing to how you defined it when you just started jive 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 yeah 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, um, for that to surface from within takes a lot of work, you know, easy idea, hard feeling, uh, to, to truly feel.
51:46So 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, and, and that's, um, 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, and meaningful ways, kind of all there is and that motivates you enough 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 it's you know my next book is is called right now called the eros advantage and eros is human desire it's 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 yeah they seem so small that they're irrelevant when you're pulled come where that that way i i i know exactly what you're 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 uh and i think that to me is the 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 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 bs there is no the ego is just lying it's just a it's like a evolutionary quirk that made humans the way we are, but it's not true.
54:14It's not real. 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. I'm doing that thing. and the voices have gone away. So you're thinking about money and wealth. How has that changed over time? Yeah, I mean, it changed pretty substantially. 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.
55:02It's just a form of energy that can be moved through the world in ways that can support the thriving of the people that 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, you know, use that money for their own ego purposes or, you know, other things. I just think that time is over.
55:45Like, 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, you know, 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 you know 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 you know 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 you know what 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 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 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, you know, souls who want to live better lives.
57:46And 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. And so 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. I think it's very needed. I think technology is way ahead of our understanding of our own psychology 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.
58:23Or we should all become more educated spiritually and psychologically. 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 color commentary for understanding what the future of businesses look like. So, yeah, couldn't agree more. How do you choose people you surround yourself with? Yeah, it's a good question. It kind of changed as I, as my, um, 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, uh, to, to just ground myself in me that the people I surrounded myself with changed a bit.
59:15just 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 that, 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 and strong ways are also starting to do more of this work. And, and, you know, that's, um, heartening to me that there's more of that.
59:54And so, but it's not like I just surround 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, um, 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.
1:00:35They 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. It's like the old me would have been like, it's a no asshole rule and I don't work with assholes. The new me, I think, would be like, well, why are they an asshole? What's going on? What's happening to them? And can I help? Is there something going on there? So, yeah, I would say I choose to spend time with, you know, people who at least where there's motivation to be the best they can be. And even if they're earlier in that journey, it's okay.
1:01:16You 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. 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 it kind of ripped it all apart and I showed up as an open, vulnerable, you know, broken down version of myself.
1:02:05And 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. Yeah, because essentially the process you're describing, what you did to yourself is not that different from what you're doing to those companies. 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.
1:02:41Right. 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. 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 transformations. What you said is much more brilliant way than I could have put it. Brilliant way 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. It'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 at it as a person.
1:03:26That's right. It's the same process. Absolutely. And I actually really love the trend that we are watching now, this creator economy, when people are giving 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 yeah exactly and it's beautiful to what people and find in that place and liberating themselves from all the junk uh of expectations from other 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 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 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 um more whole and sovereign quicker than our generation did i hope yeah 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.
1:05:04So I think the trend is actually quite good, quite hopeful. I'm very optimistic. 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's 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 and spiritual understanding and, you know, the state of the planet and the world.
1:05:45And so, yeah, I agree and look forward to seeing how it all plays out. Exactly. Let's hope that all the promises for longevity also lay out in our favor. Yes. We've learned enough to see all these generations. 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, maybe they'll figure it out somehow. Yes, exactly. So Dave, a perfectly fulfilling life, what is it for you? 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.
1:06:37Like 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. It's like, it's being there for all of it. Um, the Charlotte Joko Beck, the, um, you know, Zen philosopher writer, um, said that happiness has an opposite and joy doesn't. meaning if you're seeking happiness you're trying to push something away but you know when you're seeking joy you're just alive in all of it uh and i think for me that's that's fulfillment is it 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.
1:07:24It makes everything better. You know, the colors are brighter. The, you know, 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. So may I ask you, if you have to rate your fulfillment on a scale from zero to 10, where are you at? Ooh.
1:07:54um maybe i'm eight okay that's right especially 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 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 um wonderful for me just feels so different now um 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 10 because then if you get to 10 you're just saying like you know maybe you die at that point you're dead yeah 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 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 it's so subjective because i i got to know the person um 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.
1:09:17But 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. But the internal work of understanding yourself. 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 you know desire more and you see that inner work is a constant that it makes everything better and um you know and maybe you know i think in my life it's probably 15 of what i do is somehow related to some form of inner work you're writing a book i met 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 yep for sure so so what keeps you up at night my dog um getting too hot yeah i think that's you know i don't have as much of that anymore um you know i still like we'll get the financial stress you know that that lizard brain middle of the night thing um where you get little problems that seem like they're really big in the middle of the night, but to a much lesser extent than I used to, there's nothing, you know, I went through a divorce, you know, the last couple of years and that's obviously traumatic and can, um, you know, cause a lot of deep pain.
1:10:45It was, you know, very hard for me. Um, and, um, 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. 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, if you go through it exactly Exactly. As you said, you always come out a better person. Yeah, exactly. And you got to use that opportunity to do that.
1:11:28And 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, my factor of 10. So I will take the gifts that come with those, those life changes. It's that kind of suffering that brings joy at the end somehow. We just don't know how, when we go through it yeah okay i take my last question's been such an amazing conversation and thank you so much for opening up and going so deep and my last question is how do 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.
1:12:14So 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? 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. Great. I would love that too. Thank you so much for having me today and asking all these awesome questions. This is really fun and cathartic.
From the publisher
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.
Connect with Dave:
Website: https://www.davehersh.com/
Reignition - Book by Dave Hersh: https://www.amazon.com/Reignition-Transforming-Startups-Breakout-Winners/dp/1639090347
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(00:00:00) Intro
(00:01:21) Welcome
(00:01:33) Life After Selling the Company
(00:02:05) The Founding of Jive
(00:04:24) Changing Trends in Digital Communication
(00:05:14) The Challenges of Scaling Up
(00:06:02) Life After Leaving the Company
(00:08:16) Dealing with Identity Crisis
(00:09:12) The Hoffman Process
(00:10:46) The Art of Accomplishment
(00:13:20) The Long Process of Reinvention
(00:15:36) The Need for Inner Work and Transformation
(00:16:37) Overcoming Entrepreneurial Struggles
(00:18:01) Trying to Reconstruct Past Success
(00:19:26) Finding Clarity and Direction
(00:21:01) The Process of Transforming Identity
(00:23:00) The Liminal Space Between Old and New Self
(00:24:43) The Wilderness and Benefits of Being a Ghost in Between Worlds
(00:25:20) Transition from Jive to Andreessen Horowitz
(00:33:30) The Decision to Leave Venture Capital
(00:35:31) Acquiring Businesses and Understanding Their Core
(00:38:15) The Art of Identifying and Peeling Away Non-Core Activities
(00:42:30) The Transformative Power of Returning to Your Core
(00:43:55) Bounce Back Post Acquisitions and Restructures
(00:44:12) Experimentation for Growth & Financing
(00:45:24) Transforming into Purpose-Driven, Disciplined, and Strong Culture Businesses
(00:46:08) Building a business that matters
(00:53:00) Personal definition of success
(00:54:33) Choosing the right people to surround with
(00:57:29) Reimagining the idea of a company
(00:58:38) Personal transformation and rebuilding
(01:03:28) The trend of the creator economy
(01:04:52) Optimism for younger generations
(01:05:58) A perfectly fulfilling life
(01:06:32) Discussing happiness and joy
(01:07:26) Rating personal fulfillment
(01:08:33) Advice after selling a company
(01:09:16) Importance of inner work
(01:09:55) What keeps one up at night
(01:10:19) Discussing personal divorce
(01:11:33) How one wants to be remembered
(01:12:11) Anticipation for upcoming book




