345 Retired Founder

Jeffrey Feldberg: [00:00:00] Our next guest is anonymous online and on the podcast to protect his individuality with himself and his family, and goes by the social media handle, Retired Founder. Retired Founder is a middle class kid from the Midwest that sold his bootstrap SaaS business in three transactions, from 2017 to 2022, and retired in 2018.

 Happily married for 30 years with three great kids. His post exit journey has been different than expected. The retired founder didn't anticipate the deep sense of purpose and identity tied to his role as a founder and CEO. Today, Retired Founder operates anonymously online for privacy and authenticity, but glad to introduce his true self to anyone on the path.

Jeffrey Feldberg: His current project is building a Community of post exit post economic founders called Beyond The Finish Line. 

And before we hop into the podcast, a quick word from our sponsor, Deep Wealth and the Deep Wealth Mastery Program. We have William, a graduate of Deep Both Mastery, and he says, I didn't have the time [00:01:00] for Deep Both Mastery, but I made the time and I'm glad I did.

What I learned goes far beyond any other executive program or coach I've ever experienced. Or how about Bruce? Bruce says, before Deep Wealth Mastery, the challenge I had with most business programs, coaches, or blogs was that they were one dimensional. Through Deep Wealth Mastery, I'm part of a richer community of other successful business owners.

The idea shared forever changed the trajectory of the business and best of all, the experience was fun. And we'll round things out with Stacey. 

Stacey said, I wish I had access to the Deep Wealth Mastery before my liquidity event, as it would have been extremely helpful. Deep Wealth Mastery exceeded my expectations in terms of content and quality.

And you know what, my Deep Wealth Nation, why they're saying this is because Deep Wealth Mastery, it's the only system based on a nine figure deal. That was my deal. And as you know, I said no to a seven figure offer, and I created a system that we now call Deep Wealth Mastery that helped myself and my business partners, welcome from a different buyer, a different offer, a nine figure [00:02:00] exit.

So if you're interested in growing your profits, preparing for a future liquidity event, if that's two years away or 20 years away, and you want to optimize your post exit life, Deep Wealth Mastery is for you. Please email success at deepwealth. com. Again, that's success, S U C C E S S, at deepwealth. com. We'll send you all the information about Deep Wealth Mastery, otherwise known as Scale for Ultimate Sale. That's where you want to be. You want to be with other successful business owners, entrepreneurs, and founders just like you who are looking to create market disruptions.

And they want to lock in their financial freedom and have success and fulfillment. 

That's the 90 day Deep Wealth Mastery Program. It has your name on it. All you need to do is take the next step. Send an email to success at deepwealth. com.

Welcome to the Deep Wealth Podcast. Well, he's back. The retired founder is back on the Deep Wealth Podcast. For everyone in Deep Wealth Nation, today, we're going to be doing a deep dive on the retired founders. Not one, not two, but three liquidity [00:03:00] events that he had with his company. Let's For lessons learned and everything you'd ever want to know about being in that kind of situation.

And if you didn't listen to the retired founder in the original episode, where it was AJ Wasserstein talking about his new case study on the post exit life, 12 questions every post exit entrepreneur should answer, that's where the retired founder came on and he said, And for privacy reasons, we're keeping his real name out of it.

And when you listen to the episode with AJ, I was jokingly saying to AJ, Hey, my name is Jeffrey. Why don't we call our guests, Jeff, AJ, it'll be really easy for you. Jeffrey and Jeff, you can't get it wrong. And so for this episode, we'll go with tradition and we'll call our guests, Jeff. So Jeff, welcome back to the Deep Wealth Podcast.

Absolutely a pleasure to have you with us and for our new listeners in Deep Wealth Nation who haven't listened to that podcast yet, where you hit it out of the park with AJ. I'm curious. There's always a story behind the story. So Jeff, what's your story? What got you from where you were to where you ended up today?

@RetiredFounder: Well, thank you first, thanks for having me back on. [00:04:00] I'm glad to be here and, share my story and speak to your audience. I'm going to go back to my birth, but I'll get to today really quickly. So I'm a middle class kid from the Midwest. I grew up in a loving home, had a lot of advantages.

We weren't rich, but roof over our head. My mom stayed home. I went to public schools. I was a salesman by trade. I've been an entrepreneur for quite a while. The big hit that I had was a software company I started in 2003. And as a human, I've always been motivated by money. I was the kid that shoveled snow.

I was the kid who cut grass. I was the kid walking up and down the street selling whatever I could sell. I had a paper route. I was a telemarketer. I was a survey taker. I was a referee, an umpire, a lineskeeper. I did it all. Anything I could do. I was always been motivated by money. Started my company. In 2003, with the motivation of making money and doing good.

And it was the best option on the table. I'll stop, there at the founding of the [00:05:00] company. If you'd like, we exited 18 years later in totality, so I'm glad to go into any of the details. Inside of that.

Jeffrey Feldberg: Absolutely. We will. And you know, offline, Jeff, what we're talking about was how, and I really respect this, you value your privacy, not just for yourself, but for your family. And so for those that are out there that are listening, perhaps you can share not only why you're taking that stance, but also I feel it's a privilege.

I feel we are the most fortunate people in the world where you have financial means, but people outside your circle have no idea. You can just be anyone else walking down the street and you're not going to get that unnecessary attention or the paparazzi or all those other not so great things that come along with that.

So for the benefit of our listeners, what's going on with that?

@RetiredFounder: appreciate you asking. Yeah. Thank you. And I can tell you with a hundred percent certainty, nobody knows who I am. Nobody cares who I am. I'm not a fraud, but I'm also not famous and hiding. The reasons that I chose to be and choose to be anonymous three. The first is just to protect my [00:06:00] identity.

I'm retired, I don't have anything to sell, I don't need any personal attention, so therefore any attention is bad attention. I'm happy to exchange my ideas and love exchanging ideas with people, and when people talk, you know who I am. When people reach out, of course, I introduce myself as myself. The second reason, and maybe it's because I'm a coward or incapable of saying some things or not running my thoughts through a filter, but I've found being anonymous allows me to be completely authentic. And I think that's what raws people do. Maybe to my, Twitter account or to the, conversations that I have that I'll say anything.

I'm going to tell you things today my mom doesn't know. And to me, it's liberating to do that without having to think, oh, what happens if my sister listens to this? The third and final reason, there are probably more, but the third reason I'll list is, I tell stories sometimes about the people in the companies in my life, and it allows me to protect those.

I might tell you a story about a billionaire I know, [00:07:00] and it may not be that flattering, and if you knew who I was, you may be able to triangulate who that person was. Same goes for my old company, private equity partners, investment bankers, sales. Some things I have good to say, some things I have bad to say.

It's always going to be authentic, and it's easier for me to be this way. So thanks for accommodating.

Jeffrey Feldberg: Absolutely terrific. And thank you for the insights. And it gives a lot to think about for our listeners in Deep Wealth Nation. Hey, when you cross that finish line, where do you want to be? And as I like to say, different strokes for different folks. Maybe you want people to have a notoriety. You want people to know about you that you did this and where your net worth is at.

Maybe you don't, it's something to think about, but Jeff, let's go back to growing up and you've been very open and vulnerable just now and also in our previous episode. And so when you look at your business success today, all these years later, you went into business, you had no idea that you would likely end up where you did growing up the way that you did with your family in the really middle class kind of family [00:08:00] environment that you're growing up in, did that impact you in any way?

Did it make any. Perceived or real differences for you.

@RetiredFounder: I've asked myself that question, Jeffrey, and I wish I had a better answer. I've always been drawn to money. The only thing from my childhood where I could draw a line to that is my dad worked really hard. He was gone to the office he was a, worked a white collar job, mid level management at a firm, fabulous man.

Up early, home for dinner at 6. 30, 15 minutes to eat, and then he was working on papers. He was working. And I don't know if it was modeled to me that it must be important to work and make money. But it's always been an attractive to me and that's the best I can do to draw that line.

Jeffrey Feldberg: Fair enough. So being attracted to money, at least you called it for what it was, you owned it and you knew that was literally your currency. And so now when you're building your business, [00:09:00] firstly, to get you to the first liquidity event, when you look back at the business, what was unique to you or at Deep Wealth, what we say, some of your X Factors that really had you stand apart, that had the attraction of investors to come along and say, hey, yeah.

Let's take an interest in your company.

@RetiredFounder: we were a 15 year overnight success. So I don't have a handy list in front of me, but I had a technical co founder, so I was the CEO. my partner was the CTO and it was my money. So I was the majority shareholder and together, the, I mean, the first thing I would have to say was the hypothesis of the business proved to be correct.

was his idea. The idea was correct that there was a trend happening in, software and security software That, that was going to happen and he was right. Now, it didn't happen overnight. Our first year in business, we did 9, 920 of revenue and don't think I don't have a copy of [00:10:00] that purchase order because it came in on December 27th.

We worked all year, Jeffrey, for 9, 920 of revenue. So part of it was just staying in the race. we went from, 10 grand of revenue to 80 to 320. To 650 to a million. We broke even in our fifth year of business at a million dollars. So we stayed in the race and like marriage, the key to success is not quitting.

And boy, would I have loved to have quit the first few years. It was. It was hard, I mean, it was just hard and a lot of rejection and a lot of questioning. Is this going to work? Lot of sleepless nights throughout and a lot of I'll share one of my, quips with you for any of your, listeners that are starting a business that have a spreadsheet and they're projecting what's going to happen in the first year.

And it goes like this. If you're lucky, it's [00:11:00] going to take you twice as long and cost double what you projected to get halfway to your worst case scenario. when that happens, don't feel like you're special because it happens to everyone. There are a handful of stories people hear about Mark Zuckerberg starting Facebook in his dorm room and he's an instant billionaire.

It does happen, but people win the lottery too. And when you start a business. And it starts slow and you get kicked in the teeth, stay with it. And I would say that was probably the number one thing. And I can go into several others if you'd like, I don't want to, I don't want to take up too much time with that.

But I would say that would be the number one thing is know it's hard and you've got to stick with it.

Jeffrey Feldberg: And so Jeff, when the company is struggling, even dare I say failing, it's always a fine point. Do I continue moving forward or do I call it a day and find other greener pastures for me to put my focus on? And sometimes. In my example, I've done both. I've either stayed at it too long [00:12:00] or I've quit too early.

Now with Embanet, thankfully I did all the right things, although I made a gazillion mistakes and I jokingly say, half serious, really, if I had a dollar for every mistake that I did at Embanet. I wouldn't need my nine figure deal. I would have had way more than that. So for you, you know, 9, 920 year one, not really much to show.

It took you a few more years to start having things pick up. You're the 15 year overnight success. Like you're saying, what kept you in the game? Because I would suspect those around you're saying, Hey, Jeff, what are you nuts? Call it a day, move on, try something else. It's not working.

@RetiredFounder: That certainly would have been a rational suggestion and credit to my wife who, For whatever reason, never told me to get a job, always believed in me, stayed by my side and didn't quit. One of the things that was perhaps helpful and I should just pause real quick and say, if I would've gotten a credible job offer in year one and probably year [00:13:00] two, Gone with the wind. But the thing I would say to someone who's in the middle of it is you can't know and be confident about how things are going to play out. But you can be confident in your ability to deal with however things turn out. And I'm a salesman by trade. So, I always knew I could just pick up a bag and go back to sales.

And yeah, maybe we would have to sell our house or do something else. But you know, if you have your health and you have your partner, my wife in my case and confidence that you'll be able to, Find something else. It's okay. It's okay.

Jeffrey Feldberg: And was there a pivotal moment, Jeff, in the company's history where, okay, tough time still ahead, but yes, we've passed that point. It's green pastures ahead. We're now finally finding a rhythm. We're moving forward.

@RetiredFounder: Yeah, that was probably your, I wanted to quit the [00:14:00] first couple of years. Just get that out. Would have quit if I had a better opportunity the first couple of years. By the time we got to year four, we were still losing money. We borrowed a little bit of money because we could see breakeven ahead. And in the fifth year, we did a million dollars of revenue and we broke even.

And at that point, I felt like it was going to work. it wasn't until five years. one of the reasons if you wanted to. List decisions that were good and there were many that were bad, but among the decisions that were good was selling our software as a subscription, which everyone does.

Everyone does now in 2003, 2004, it was very novel. And it wasn't because we were futurists or super wise. It was because no one would give us a license. No one wanted to pay a hundred grand for the software for, two guys and a dog, but they would pay a thousand dollars a month. one of the other [00:15:00] taglines, I guess, that may be etched on my tombstone one day that also I think could be categorized as a good decision. And this works really well for subscription software for people starting out is the mindset of short term generous, long term greedy. And we knew we had confidence if we could get a customer, even if they were just paying a few hundred dollars a month.

We knew we could get more utilization, more benefit and then long term more license revenue. And it, almost always worked

Jeffrey Feldberg: And so Jeff, short term generous, long term greedy, short term generous in today's environment. What would that look like for you?

@RetiredFounder: well, for, I mean, I think for anyone listening, it would be, if you're confident in your product, don't let money get in the way of getting a customer. So, if I had a hot dog stand and I felt like I had [00:16:00] really good hot dogs. And I wasn't selling any, I might think, I'm going to give away hot dogs today because they're so good.

People are going to come back and buy them tomorrow. That's a lousy example, maybe, but in our world we had a customer that ran a process and ran us through the ringer to buy our software, a bake off among many other competitors. And we just killed it. We did such a great job and the funding for the project got full, pulled.

And we decided, and this was confidence in the team, was fortunate to be surrounded by great people. We said, I'll tell you what, the money's gone, but we're not, we're going to give it to you for free for a year. And at the end of the year, any reason, no reason at all, kick us to the curb. If it's working for you, keep it.

And it turned into a million dollar a year customer. it was our second biggest customer. and I don't mean to paint myself as being. Smart. That should be my company having confidence in the people to execute and confidence in the product enough to be short term generous.

Jeffrey Feldberg: Jeff, as you're describing that firstly for our listeners [00:17:00] in Deep Wealth Nation, if you're in startup mode, maybe you're in year two and you say, Oh my goodness, I got to get to year five or more. That's where Jeff got to before he got that momentum. It's a terrific strategy. And what's interesting in this economy, the freemium economy that's come out with all these apps and everything else.

It seems as though entrepreneurs have lost sight of the fact that free is good up to a point, but you got to be in business to be in business and you need to draw those lines. And so while it was very generous of you for the first year that you gave it away for free, it sounds like you drew a line in the sand.

Hey, do what you want with it for the first year, but starting year two, here's what the business model is going to look like. Is that how it went down?

@RetiredFounder: That's exactly how it went down. We were upfront about the, what it was going to cost, based on the number of, of licenses. I think they had an idea how much they would use it. I think we had confidence that they were going to use it more. And I mean, at the risk of being crass by the time we got to month six, was no turning it off. There was no turning it off. They relied on it. It was a [00:18:00] mission critical application for them. We could have, we didn't of course, but we could have doubled the price and they would have been a customer.

Jeffrey Feldberg: Terrific. Terms may change. Technology may change. The human condition doesn't. In the hardcore school of sales, what salespeople often call this is the puppy dog technique. And the story goes, hey, give the puppy dog to the family. Take the puppy home for a weekend, Friday. Take it home for the weekend, Friday, Saturday, Sunday, on Monday.

If you don't like the puppy, bring it back to the store and you'll have a full refund. No questions whatsoever. And rarely does the puppy come back because like in your case, they begin to love the puppy and wow, how can we live without this puppy? Life is so much better. And it sounds like you followed a very similar kind of path there, but with good intentions on your part and also reciprocity.

So Jeff, as you look to the success of your business. Where in this case, you gave it away for free for a year, or perhaps in other instances, [00:19:00] this whole thing about reciprocity. If I do something for you, that people feel bound to do something for me. Do you buy into that? Is it hocus pocus? Is there something to it?

Did you ever come across that in your other dealings?

@RetiredFounder: I think for the most part, we were pretty commercial. I don't think I can think of a counter case where we gave something away or tried to give something away. Or provided a favor services, a customization for a customer where it they didn't start using it and they said, you know what, we're going to pay you anyway.

So I think different industries, of course, have different people and different characters in the software business we were in. I think either it worked or you were gone.

Jeffrey Feldberg: Fair enough. And so Jeff, you're trugging along here. Things are moving nicely. So for the first liquidity event, can you set this up for us? How did that happen? How did it transpire?

@RetiredFounder: Yeah we were making good progress. I had very high percentage of my net worth wrapped up in. This company, I didn't have, I'd never sold any [00:20:00] shares. And so, I built an office building and owned a pretty big chunk of debt on that office building.

I had all my chips in the ring, all of them. And after, a certain number of years that it begins to wear on a person not all people, but it was beginning to wear perhaps. And in my case it happened to me March, 2017, my phone rings. And it is the business development, corporate development guy from our biggest competitor, our closest competitor.

And he said I'm interested in buying the company. I think we'd be a great fit. And I said, well, I'm terribly offended wouldn't even consider it. I'm insulted you even would ask, but as long as we're on the phone, how much were you thinking? And when he told me everything changed at that moment, it became real.

And everyone has a number in their head of what I need to be done. And this number represented what would be two X done for me. And we started a process that was how it started.

Jeffrey Feldberg: So the good old competitor reached out, it [00:21:00] opened your eyes to what was possibly there. And so Jeff, when you started the process, what did that mean for you? What did that look like?

@RetiredFounder: Oh, I wish I could tell you it was a straight line. And it wasn't I'm going to say we, I was the majority shareholder, but you know, there were other stakeholders involved in this. My, my partner and key employees. There was a consideration of, okay, we could just do this ourselves and sell to this company right here.

And now there was a consideration of maybe we should find a financial sponsor, a private equity partner, a venture capitalist, maybe we should, shop the company around. So, we bounced back and forth with other competitors, partners, maybe we should do a minority share sale, maybe a majority share sale, maybe all of it, and we bounced back and forth a lot. and I think that's healthy. Anyone that says, you know, I instantly knew exactly how this was going to play out. I dunno, maybe that happens, but I don't think it's typically a straight line. So we considered a lot of different options in the routes to go.

And I couldn't be happier with the one we ended up. Choosing.

Jeffrey Feldberg: And so this was, you brought in [00:22:00] an investment banker and ran a competitive process to find At that time, the winner of round one,

@RetiredFounder: That's exactly right. I had exposure to the private equity firm who I'd love the name because I love them. They're, they were just really good to me. And there's a reason that they've been so successful. But I had met some people from that group and had learned that they were actually incredibly smart and saw a lot of the things the same way I saw things.

So I had, my eye on one, but we did hire a banker to run a process. And for anyone, anyone listening that's in that position that might be thinking, I could save a little money by doing this myself. I wouldn't recommend it. I thought I knew what it would be. I thought I would send some spreadsheets.

I thought, we'd have a couple of meetings and maybe demo the product. And the investment bank we chose was a small boutique firm. Again, I wish I could name them, but I'm gonna not cause they were so great. Anyone contact me on Twitter at [00:23:00] retired founder. I'll tell you who it was.

They were playing a game that was so many levels deep that I didn't know existed. They were pitting one against another. They were just playing a game I didn't understand anything about. I'm a salesman. I thought, well, no one can sell this company like me, but I mean, it was truly impressive and we wound up with the right sale price with the right partner and the right terms.

Jeffrey Feldberg: and Jeff, the listeners can't see me, but I'm giving you a virtual high five because that's exactly what should be done. You bring on an investment banker, you have a competitive process. And like you said, you didn't do it yourself. If you were thinking, Hey, I can save some money. It's probably going to cost you more money than doing that.

But let me ask you this because so many business owners, when they get that phone call, They succumb to the phone call and they end up selling to the competitor or to the unsolicited bid. You could have, but you didn't. And you said, Hey, I had never really sold a company before. I was new to all this.

It must've been very tempting. What was it [00:24:00] that had you keep on keeping on?

@RetiredFounder: I'm glad you asked and I can't say one thing but I have to say this up, up front, the number that the competitor told me on the phone that fateful day, I thought, okay, that's going to be the number that would be the number they knew. They knew we were running a competitive process. They knew there were other competitors bidding. They knew there were multiple private equity firms bidding. And the banker told me, said, based on what this company is and their last round and this valuation and this person and the age of this fund, again levels of things I didn't know.

They said, they're going to bid this much. And it was about 20 percent below.

And I bet they stood on their tiptoes to get to that number, knowing that it was a competitive process. So that number they gave me was false. and I thank them for it.

Jeffrey Feldberg: And so for our listeners out there, my takeaway from what I'm hearing you say is, Hey, if you get that phone call. If you like the number that you're hearing on the other end, it's probably an even better number. Do the right thing, have a competitive process, surround yourself with the right advisors. How am I doing with [00:25:00] that?

@RetiredFounder: That's spot on. Don't fall into any of the traps. If you have a desirable asset, don't be in a rush, don't sign exclusivity. Don't give anyone an inside, track that excludes others. This is just my experience. Others may have, different experience, but in my view, you're crazy to not hire someone to help you sell your business.

Jeffrey Feldberg: And Jeff, I was exactly where you were at. What set me on my journey, I had that seven figure offer, very experienced buyer, knew exactly what he was doing, knew that it was well under priced, but also knew he was dealing with an inexperienced entrepreneur when it came to M& A.

And thankfully, like you said, no, ran the competitive process. That's where the nine figure deal came from. And Jeff, I was so naive when I came out of my deal. I thought I was more the exception than the rule because as entrepreneurs, we work so hard, we do such wonderful things. We change lives and make the world a better place.

Who would ever want to rip us off? And like, in your case, same thing [00:26:00] potentially happened there. I saw it happening again and again. And that anger that I had, that's really what was the beginning part of, okay, let's create what we now call the 90 day Deep Wealth Mastery to have people from start to finish, figure out how they can grow their profits, how they can prepare for a future liquidity event two years from now, 20 years from now, whenever it's going to be.

But not have any deal, have the best deal. So for round one, let's call it, where did that leave you with a company in terms of the percentage that you now own with a new investor?

@RetiredFounder: At the end of the first trade I owned, I believe it was about 25%. Of the company. I was in the 57 percent range to begin with, and then 25, and then down to single digits on the last trade.

Jeffrey Feldberg: And Jeff, with the next question I'm going to ask you, I'm actually thinking of step three in our nine step roadmap of the Deep Wealth nine step roadmap, future buyer, when you know you have not just any investor in your case, but the best investor, [00:27:00] that's what gives you the ROI. That's what pays the dividends.

So would it be correct in saying. You came out of round one with 25%. You selected who you felt at the time was the best investor. Sounds like it was private equity. Did they then lead the charge with what turned out to be another two liquidity events that you didn't know at the time, but what was waiting for you down the road?

@RetiredFounder: Yeah there's, a lot there. Do you mind if I hit the rewind button here, 30 seconds based on something you said about the process?

Jeffrey Feldberg: Absolutely. Let's

@RetiredFounder: I think this is something for any reason because we had such a big exit, anyone listening thinks, boy, this guy really had it figured out just, let me relieve you of that thought I did not the thing I wish I would have known in preparation for selling the business is this, at least companies in the business we were in are like a slot machine.

And the slot machine has these reels that spin, and of course your revenue matters. But in my business, what mattered was your gross margin, which I didn't really know, your growth rate. [00:28:00] And when the analysts came in and dug the company apart, it turned out we had excellent gross margin. We were close to 90 percent gross margins.

Our customer retention rate was world class, 117 percent net. And our growth rate was 20. Now if you think about a slot machine, that's like jackpot, potato. And the potato was our growth number, it was 20%. So if I had it to do over again, I would have understood those numbers. I would have, of course, managed try to manage margin and retention, but I would have been a little harder on the throttle because had we been 30%, 40%, 50 percent growth, that slot machine would have paid out a lot more.

So sorry about the, rewind, but I just think anyone, whether you're running a services business or a software business or a restaurant, whatever it is you're selling, boy, knowing what, if you're looking to sell, knowing those key metrics and really driving them is something I could have done better.

And I wish I would have done. sorry for the diversion. Would you remind me of the next question you wanted to talk about the partner? I think we had.[00:29:00]

Jeffrey Feldberg: Well, I'm going to get there, but I want to go down a rabbit hole that you just opened up and we're kind of all over the map, but there's a method to our madness here. And let me ask you this. When it comes to your third round, you did incredibly well. You were not only nine figures, you're high nine figures.

And so let me ask you this. At one point, does it really make a difference when you have a kind of success financially, materially, and otherwise that's coming in? If it was 20%, that number that you're referring to, or if it was. 120%. Does it really make a difference at one point once you cross a certain threshold?

And I ask that with no judgment. It's coming from a place of curiosity. Everyone is different. Everyone's currency is different of what matters to them and what that looks like. I'm just curious of where you are right now. Would it have really made a difference in the scheme of things? For your journey and where you've been and what you now know.

@RetiredFounder: that's a really good one. This should be the deep question podcast. In my case, I had a [00:30:00] number that I always thought if I could get to this number, I'm free. And when we sold the company, the first time I had a little more than two times that number. And based on the reputation of the partner we, selected. I had confidence, but not certainty that the equity I rolled would result in anything back at all. I was prepared. You know, I had to X, I was fine wound up about nine X of my number. And it's difficult because there's not a counterfactual to say, well, if you had bound up at one X or 2.

7 X, Would you be? The same. Does it matter? I don't know a single person that would object to having twice as much money as they have. I have enough. the best amount of money anyone can ever have. And that's enough. And the only person that can tell you have enough is you.

I'm not close friends, but I know a guy that has multiple billions of dollars, runs [00:31:00] a dozen or more And he told me directly when he dies, his assistants have specific instructions to have him cremated and put his ashes behind his desk. And at that point only, he would consider retiring and you know what?

God bless him. That's who he is. He does it well. I have a lot of love for the person but for me, I have enough. And so I like to think if I would have wound up with half as much, I would have enough. I'm not sure if that answers your question. It's a thorny topic.

Jeffrey Feldberg: Actually it does. And there's some really important takeaways for Deep Wealth Nation, because Jeff, what I'm hearing you say. And I'm going to go back to picking the right investor. How do you know which is the right investor or the buyer? But what I heard you say is we call them at Deep Wealth deal points and no fly zones.

What's a deal point? What's a no fly zone? Well, before you start your deal, before the pressure's on, before you're in deal fatigue mode. Exactly what you want and don't want. And in step three, future buyer, future [00:32:00] investor, we go through with our participants, the business owners, what those are.

And one of the deal points or no fly zones, Hey, I will not accept an offer. That's a dollar less than X, whatever X happens to be. And that in advance, or it could be a deal point. I will only move forward with an offer. If it's at X Factor. X plus a dollar, nothing less. And so from what I'm hearing you say is it was two X for that first round that came through and that gave you the confidence, okay, if everything just goes off the rails here, I made a mistake.

I chose the wrong investor and I don't get anything back for my 25 percent ownership in the company. You're already ahead of the game. Did I get that right?

@RetiredFounder: You got that right. Of course I was hoping,

To improve but yes. And I have, a lot to say. I hope we have time to cover selecting your, partner.

Jeffrey Feldberg: what we're going to talk about that right now, because right up front and spoiler alert for all the listeners, because you selected well, [00:33:00] that led to liquidity event number two and number three, where you were ratcheting up your success, your wealth, what the company was able to do. That wouldn't have happened though, if you had chosen the wrong investor at that time.

Who just blew up the company or didn't agree with you, or just made really bad decisions because we know oftentimes once a company is acquired. More times than not, they're not great statistics. The company doesn't succeed, it actually fails. And you hear about the business owners buying it back for pennies on the dollar.

So, listen, hindsight's always 20 20. But Jeff, you chose right. Congratulations. It served you very well. Did you know that at the time of what you were looking for that would make the absolute right investor? Or looking back now, you obviously know. What would you say to our listeners on, what do you look for?

What does that look like?

@RetiredFounder: I'd start with the people and I had an opportunity to meet some people prior to running the process [00:34:00] and have an understanding of this particular firm, but. I have heard of cases, and this didn't happen to me, but I've heard of cases where there are deal teams that are part of the acquisition and then a separate operating team.

So imagine you're dating and you get to know your soon to be spouse. And then at the altar, it turns out they're done and a new partner comes in. I wouldn't like that. So I think, it's really important to, and you got to go to war with these people. And if you don't like them that's a tough draw.

I think that's thing number one. And I'm happy to go through two and three, unless you want to, unless you want to double click on

Jeffrey Feldberg: on going. So it's the old bait and switch. Make sure whoever you're selecting that they're not there just to close the deal with you as the entrepreneur, but they're going to be there day in, day out during the liquidity event.

@RetiredFounder: Absolutely. And the stories, you know, I get to hear, I get to hang out with other founders and talk to other founders. It's such a fun place in a privileged place. A lot of what ends up getting [00:35:00] talked about. Afterword is not the jet airplane and the shiny car and the beach house. It's about feelings.

It's about how they were treated. It's about how their employees were treated. It's about promises made and broken. It's about everything but the money. And If you are, or your listeners are like most founders, you have a very close attachment to your company. You do not want to turn that over to the wrong person.

So, simple question, if we end up doing a deal, if you end up buying my company or investing in my company, Who are the people I'm going to work with on a day to day basis? Super important. Thing number two I would point out is understanding the difference between a venture capital firm and a private equity firm and understanding the difference between a fold in investment and a primary investment.

And I'll step through those real quick if you want, unless you don't want me to go there.

Jeffrey Feldberg: Absolutely. Because I know so many people, they throw these [00:36:00] terms around, Oh, venture capital, private equity in the same breath, and they're very different things. So. What do you want our listeners to know?

@RetiredFounder: I did too. was ignorant of this. I was always of the school that private equity and venture capital, almost, I used them interchangeably, really. Venture capital this. We're going to put a hundred astronauts in a hundred rockets. And one of you is going to hit the moon. Sixty of you are going to burn on the launch pad.

And 39 of them you're just going to kind of buzz around in low orbit and, some will crash and a few will be okay. And if you're okay with that, man, if you're okay with that, if you're looking to be that one that hits the moon, go for it. Don't be surprised if you have a start like we had, where you do 9, 920 of revenue the first year, that things are going to get ugly quick.

That's venture capital. Private equity was a measured approach to an existing proven business that had room to grow and improve. The [00:37:00] private equity firm that we partnered with had a similar goal to most of the other private equity firms, which was, we hope to make three to five times our investment in three to five years.

Which is not hitting the moon. It's taking something that's good and making it better, making it great. And the second half of that is the plan. To do that in our case, our plan was let's spend some money on sales and marketing because you're spending very little and improve on the growth of this business.

Remember the potato and the slot machine, our growth was only 20 percent a year and we were making 25 percent bottom line profit. And so the, plan was let's spend money. I wasn't constrained anymore by having all of my net worth in. The fold in investment is something I don't know that I would have seen coming, but, very common in private equity where they buy one primary company.

And then they add other companies to it. And if you're in that position to be a fold in investment and add on investment, I think they're called at [00:38:00] times, that's fine, but just be aware, you're not the rocket ship. you're added on to the rocket ship. And I think that's hard for founders and entrepreneurs.

If you wind up in that position where the acquiring company is really just trying to absorb and, pick up some of your people and all of your customers. So alignment, thing number two is I think probably equally important to people, which is do we have the same goal three to five times the investment in three to five years?

Yes. And do we have the same plan to get there? A lot of the horror stories I hear about people that sell to private equity are complaining that, well, they came in and they fired half the people and they cut costs and, we don't have free soda in the, Snack machines anymore, and they're just cutting it to the bone.

Well, what was the plan? Was that the plan? did you not discuss that? You should discuss this up front, because if, your goal is to, cut it to the bone and lever profits that way, that's great. Don't be surprised by [00:39:00] it. so knowing the, you know, the plan to create value, I think it's really important and agreeing with the plan to create value.

It seems to resolve a lot of the friction before it happens in my experience.

Jeffrey Feldberg: And Jeff, the word that is resonating with me, and you said it so eloquently for our listeners, alignment. And this is why, if I can toot our own horn here at Deep Wealth and our Deep Wealth Mastery Program, an entire step is dedicated to how do I know if this is the right investor or buyer and what we go through and the questions that we ask, the scorecards that we have, the process, the system that you go through, and so in your case.

It wasn't a ready fire aim. Hey, I know what I'm looking for. I know, generally speaking, what I want to see. Now, let's be smart about this. We have all these different offers coming in. I'm sure the pressure was on you. You had to choose. But you found the one, to your word, that was in alignment with you. And you took a bet.

No guarantees in life. But that bet Paid back a very high ROI. So let me ask you this [00:40:00] from the investor or the buyer that you've chosen from for liquidity event, number two, and number three, one of the benefits of choosing the right investor, which in this case, they're upfront with you, Hey, in three to five years, we want to have three to five times an ROI.

And that's really saying to you, we're not going to be here 10 years from now. If all goes well, there'll be someone else. We'll have our. Money back, our profits, and maybe you're there, maybe you're not, but they're up front about that. You knew that. And so let's talk now about investment bankers and advisors in general, but I'm going to focus on the investment bankers, often the quarterback of the whole M& A process for the liquidity event of getting things out there.

So how many investment bankers did you end up working with? Was it three investment bankers for the three different liquidity events or what was that like?

@RetiredFounder: The first one was one that I selected myself and the one that I had the experience with who again was fabulous. And I'd be glad to refer the second one was the sort of house council or banker that the private [00:41:00] equity firm used. And it ended up being the same. The same banker for the second sale and the third sale, I should mention, I didn't choose the second one.

I retired a year, roughly a year after selling the company the first time in 2018. And the second trade happened in 2020. So I was on the board, but I did not drive the second or third sale personally. I was celebrity guest appearance at best. A celebrity guest appearance.

Jeffrey Feldberg: And what's nice about this though, Jeff, because you chose right, which goes back to the investment banker that you selected, the team that you put around you, your deal points, your no fly zones, all those things that you put in place, your company was literally and figuratively the gift that kept on giving.

So maybe you showed up for some board meetings every now and again, or maybe they checked in with you, but it wasn't the heavy lifting. A year after the liquidity venture out of the company, you're now being informed about things. Am I getting that right? More or less, is that what it was like for you life after liquidity event?

Number one.

@RetiredFounder: hate to invite myself on another [00:42:00] podcast with you, but there was quite a bit there in the, with the second owner. you know, I chose to be on the sidelines. Everything went great with the first partner charts were going up into the ride.

I just got tired and I was ready to retire and turn the reins over to my, right hand person that had been with me for forever. And one of the mistakes I made just to make a quick path was in anticipation that I would be more involved and more valued and called upon. And I don't mean to sound like they, changed the locks in the office and turned a shoulder.

I could always walk in and have lunch and be the founder. When I turned over the reins, it was pretty clear that getting the founder out of the way. was part of the plan. I wasn't part of the equation. So my phone rang a couple of times, for my ego it was very disappointing to have lost that connection to the business.

The second buyer of the company was broke my heart, not financially they made my wallet, they broke my heart. They were very enthusiastic to have the founder [00:43:00] involved, asked how much time I'd be willing to put in really wanted to get to know me, really wanted to know everything. And that just wasn't true.

It wasn't true. I'm not sure why they said that, but they really didn't want to hear what I had to say or any advice or anything. And I wasn't showing up telling anybody what to do, but the things I knew about the business that I thought they should know and that they should have known, they didn't want to hear.

that was just my experience. And again, feelings Feelings are important, but I don't know any founder that sold their business that had a pristine escape from, exact right set of conditions.

Jeffrey Feldberg: And so again, I don't want to put any judgment on this and I wasn't there. Is it possible? I'm just speculation here that they were whispering these sweet nothings into your ear, hoping that, and it sounds like it worked, hoping that would have you cast a favorable impression of them. And give them the nod with the existing group.

Hey, this looks like a good group. Why don't we move forward with them? But they had no intentions of following through with that. Am I anywhere near that? Or is it just [00:44:00] anyone's guess or what was going on with that?

@RetiredFounder: Anyone's guess. I'd just be speculating. I mean,

Jeffrey Feldberg: And

@RetiredFounder: look, the most obvious answer would be they wanted me to be involved, but the ideas I had were so, dumb, they didn't want to hear them. But felt like, uh, Sherpa, the people that help guide people up the mountain.

And when I was in a board meeting one particular time before I had a very awkward conversation with the new owner, they were planning on sending a team to go climb this particular part of the mountain. And that particular part of the mountain looked really sweet from base camp. And I knew that because I tried to call on that thing 16 times.

And there's this big crevasse that you fall down. And I was just trying to tell them, like, I know that looks really good. And these are the reasons why you need to be very careful in doing that, including this giant pit that you'll never get out of. And they just didn't want to hear it. And so, at some point when you've sold, you've traded your company, you've traded your baby, your heart, your soul for money, you just have to accept that it's not yours anymore.

and by the way that investor, financially had a [00:45:00] fabulous outcome, which created a fabulous outcome for me. I don't have any hard feelings, but you know, one of the things I wish I would have known before was that really wouldn't be a big part of the story after the year or so after the first sale.

Jeffrey Feldberg: for our listeners in Deep Wealth Nation, please take note of this because so often when you bring in an investor or a buyer as the founder, the entrepreneur, after the dust has settled, many times. You're yesterday's news and it's a not invented here syndrome and there's new people, there's politics and they want to create their own legacy, their own reputation and get things out there and for better, for worse, you're just in the way.

And so many entrepreneurs and founders, Jeff, they don't believe us when we say, you've got to assume if there is a round two, you're not part of the company. That may be ownership wise, you are, but day in, time in, not happening, they're going to go on without you. And Jeff, my heart goes out to you. I've been there where after selling the company, I still had a small stake in the company [00:46:00] and not really welcome, to walk through the halls.

It's just a very. Weird, if I can use that word, feeling. People are kind of looking at you, not sure what to do. You have the old guard that you put in there and building them up. You have the new guard, but people are worried about their jobs and maybe talking with you or being too friendly with you could hurt them in their careers.

It's just awkward, not a great place to be. And for the listeners, you have to assume, Hey, I'm not going to be part of it. Other than ownership, owning stock in Apple, it's no different. I'll just hear about what's going on. And if the company does well, the stock will do well and my stock will do well. And off we go.

But it's one thing to hear it. It's another thing to live it. And it's tough. Seeing your baby going a different direction,

@RetiredFounder: Yeah. I'm glad you said that, and we can commiserate on that, that's a perfect segue. I think I've said there was three things I would tell people when choosing a partner and the third one for me I, I think this, I'm not sure if I'm speaking your vernacular correctly, but no fly zone for me was having a different class of stock [00:47:00] or a different economic.

Outcome than my partner. And we were in a position to get those terms. I know a lot of people sell their company with an earn out, and I can only imagine the compounding misery if you were the founder and you knew things and you had money riding on the outcome and you couldn't impact those decisions.

So as, as much as my tiny little heart is, still has a little broken spot in it that the founder wasn't that welcome. I was in a position financially where. I was going to get the same outcome as the owners and I hope they listened to me. It was in my interest and I thought their interest, but I wasn't in an earn out situation.

And I know sometimes that makes sense for people or that's the offer that's on the table, but to the extent possible, I would strongly recommend having your economic incentives in lockstep where it is impossible for one side to succeed without the other.

Jeffrey Feldberg: and Jeff, the, we call it the [00:48:00] E word. We don't even say it officially at Deep Wealth, the E word. So otherwise the earn out, it is banished at Deep Wealth. It doesn't exist for us. And like you, I didn't have the earn out. And for our listeners, I want you to imagine that you now have a new owner. And I'm just going to pick some numbers here that the earn out for you as the founder, it's 20 million over a set period of time.

So, the new owner now has a choice. Maybe the company loses a few million dollars in profits. But it saves paying you 20 million of an earn out. What would you take if you took the feelings out of it? There was no emotions, no humanity into it. It was, let me just do what's best for our shareholders or the investors.

Well, I'd rather lose a few million, but be up 18 million or 19 million than having to pay an earn out. Earnouts are for me, troublesome, challenging, buyers love them because it gives them so many options. And Jeff, to share a quick story as we commiserate here, once I walked away, when the new owners came in, they had a [00:49:00] different way of running things.

No judgment here, how they spent, what their run weight was, what that looked like, where they were putting that money. I had no say in that. And if I had an earn out, Well, there goes the earn out. I didn't, so whatever they wanted to do was fine because I knew at the big picture wise we all had really the same interest.

Let's just take this company to the next level. Let's do as best we can. If there was an earn out though, there would have been some complications, at least for me or some very hard feelings of how things are running. So huge takeaway. Thank you. And so I love your no fly zone. Hey, I want to have a type of stock that's aligned with the owner.

And by the way, Jeff, as I'm going down this path, different groups are different things, but I've heard from venture capitalists and private equity groups, when it comes to an earn out, as an example, they will take out a loan. Maybe they loan the company money and they're charging very high interest rates.

Now, right now, as we record this podcast, interest rates are high. Their interest rates are much higher and it's being [00:50:00] recorded against the company. The company's paying the interest to the venture capital or the private equity group, say goodbye to an earn out. So whatever the company sells for down the road, That new owner has not only benefited from three times, five times, whatever it's going to be, but also all that interest.

So you just never know how it's going to go. So I love, you know, fly zone of, Hey, I want a type of stock, a class of stock that puts me in the same league as the owner, where I'm not being penalized for this.

@RetiredFounder: absolutely. And apologies for using the E word. I would say, if that's your only choice or, you just have perfect alignment or something else, I wouldn't look down on someone for doing an earn out. It's not, but I would definitely look to have the same class of stock if possible.

Jeffrey Feldberg: It's terrific. And I take it you had a good team with you that really ensured, Hey, this message got across loud and clear. And if you want Jeff, if you want this deal, if you want this direction, that's what needs to be there. And ultimately it sounds like that's what was done.

@RetiredFounder: It was, that was a requirement.

Jeffrey Feldberg: Terrific. And then, so it sounds like for liquidity event two and three financially, you [00:51:00] did really well, but you're far removed from the company at that point.

And emotionally, it was hard for you monetarily. It was a good thing for you.

@RetiredFounder: That's exactly right. I had a pretty good idea of how things were going, the market when you're talking about, things that made the company successful, we can include good luck in that market. And because of interest rates we sold the business for seven times revenue.

The first time and 14 times revenue, the second time in uh, early 2022. So, go ahead and first of all, load up on good luck is a good thing to do. And then, And then second avoid bad luck and anyone running a business knows there's just one small thing can happen that you have no control over.

You could get sued by a giant company with a thousand lawyers. You could, in our case, we could have had one bad line of code that resulted in a breach that was unrecoverable. Things can happen. So load up on your good luck do your best to avoid the bad.

Jeffrey Feldberg: And Jeff, as you're saying that, I'm [00:52:00] thinking back to one of my very early mentors when I just got going and he said, Jeffrey, I will always choose being lucky over smart and how right he was in saying that. And so Jeff, when you look back, so many lessons learned, so many insights, what I'm hearing you say though, is you had alignment with the original buyer.

And because you chose well with that buyer, literally your company became the gift that kept on giving. Your financial net worth kept on increasing while you slept at night, relatively worry free. And I know I'm simplifying things. I'm sure there are things that came up, particularly early days and perhaps some issues here and there.

But big picture wise, your financial net worth kept on going up without you doing any heavy lifting because you chose right. And because it sounds like after liquidity event number two, You still kept some ownership in the company and that was put into liquidity event number three. How am I doing with that?

@RetiredFounder: That's exactly right. I never chose how much of the company to, of my own shares to sell is [00:53:00] a small fun fact. The company the initial private equity. Firm wanted 70%. So that number was solved. We had every employee had stock options, which we vested. And so every employee had an option.

That's not true. Some not all like line level employees had an opportunity to roll equity into the new thing, but many did. And some got to choose. My co founder sold 100 percent of his shares. When the first one came, I couldn't believe how much money it was and sold a hundred percent of the shares.

Others sold a hundred percent. Some sold fifty. I ended up just being the X. That the equation solved for just said, let everybody sell as much or as little as they want. And I'll take whatever's left over. And that wound up being about 25%. Same thing. Second time around there were fewer people with equity, but some people sold a hundred percent.

Some people rolled a hundred percent. Some people were 50, 50, and I was just the X that allowed to solve. And good luck lack of bad luck a good engine. We built a strong company. over time and yeah, I, [00:54:00] oh, I hate to say like making money in your sleep sounds like a bad infomercial, but you know, in effect, I got the benefit of the good partnership and the compounding over time and the growth of spending money in sales and marketing, which we just didn't spend that much money in sales and marketing and being able to go from a small sales and marketing budget.

I think we were spending 11 million in sales and marketing after a year of, You know, spending, I don't know, a few hundred thousand. So good things happen.

Jeffrey Feldberg: It's really a good new story all around. The key to it though, Jeff, to me, really the linchpin in all of this. You didn't have to sell because you had your two X, you're far better off. You knew your deal points, you know, fly zones. That's really the takeaway. That's why in step three, future buyer, we spend so much time on those things.

Deal points, no fly zones, who's going to be the best investor or buyer. So you knew, okay, I'm taking somewhat of a risk. It's perhaps a gamble. And if everything goes off the rails, you know what, I'm two times better than I would have been otherwise. Sounds really good to me. And it just took the pressure off.

Now, [00:55:00] imagine you had an earn out, things didn't go so well, or you really needed that money. And it just went up in smoke. That would have been a very different story, but it took the pressure off. And okay, sure. Things went off the rails. I'm sure you would have been kicking yourself. Ah, geez, I should have sold.

And look how much further I would have been ahead, but financially it wasn't hurting you. And there's a lot to be said in that particular strategy, which worked really well for you. And again, every deal is different. Every situation is different. Perhaps it doesn't work that well all the time, but it's a lot to think about.

@RetiredFounder: It worked out well, and I would advise that strategy. If you've got, confidence in the company, you've got confidence in the partner. Someone told me later from the private equity firm, That because I was willing to roll as much as I could, that was a very high confidence buying sign.

So imagine you're selling a company and you say, yeah, I'd like to stay on and work with you. I really like you. It's such a strong company. I'd like to cash out a hundred percent of my shares. Is that a company you would want to invest in?

Jeffrey Feldberg: Exactly, and for a lot of the listeners out there, they don't realize that [00:56:00] for a lot of investors or buyers, that's their no fly zone. That, absolutely not. They're not going to do a deal where the founder doesn't have some skin in the game, and it could be 10%, it could be 30%, something in between, a little bit more, a little bit less.

But they want to see that and it's something that they're always looking for in terms of, okay, yeah, this makes sense for us, or no, this doesn't make sense for us. And so it's a terrific point. So Jeff, before we go into wrap up mode, I mean, there's been so many nuggets of wisdom here that you've been sharing with us.

Looking back though, anything else that you'd want to share with our listeners? And perhaps it's a question I didn't ask or a topic that we haven't covered, or even a message that you want to get out to our listeners. You've gone through three liquidity events. The first one, you were incredibly active.

The next two is more from the sidelines, but you got a good taste of what was going on. What would you say to that?

@RetiredFounder: I don't think I have anything else to add on the sales side we could do an hour or more a week on, lessons learned, mistakes made. You asked about running a company and having the, secret [00:57:00] weapons that helped. I think deferred gratification is a really important one.

We didn't have an office until we could afford an office. we didn't have a lot of things until we could afford to have things, and I have seen people who get a little taste of success or have one good month or one good quarter, and they get out and over their skis, and they're I was always pretty conservative, but then I would also contrast that by saying, don't be so conservative that you end up leaving money on the table with that potato on the slot machine reel for growth.

So I don't know, a lot, lots more, but I think we covered the private equity side pretty well. And the rest of the stuff are just, rants.

Jeffrey Feldberg: Well, Jeff, let me ask you something because we both bootstrapped our company. And now when people know the story, they often ask me, well, Jeffrey, you bootstrapped the company. You've admitted yourself that when you bootstrap a company, it slows down the growth and the trajectory of the company. How much more successful, I'm asked, Jeffrey, how much more successful would Embanet have been if you would have had all those zeros in the bank account?

And Jeff, when I thought about it, [00:58:00] I came to the conclusion that if we would have been private equity back or venture back, we likely would have failed. I would not have had that nine figure deal because having access to that money, one of these things that we have at Deep Wealth, resilience trumps resources.

Now I didn't have a choice in the early days of Embanet. I couldn't write the check. Later on when we could write the check, because I learned about bootstrapping and that became part of our ethos, we always questioned, should we write the check? And more times than not, we shouldn't. And so I'm wondering for you, was it the same thing as you look back that the bootstrapping resilience trumps resources just because I can, doesn't mean that I should, and let's be really smart about this.

@RetiredFounder: Absolutely. When it's your own money and the choice is to spend it on something you're uncertain about. I think you're more likely to not make a mistake. And I agree with you wholeheartedly. If for some reason we would have had millions of dollars of venture capital, which happens to early stage software companies now with a prototype, we would have failed.

[00:59:00] We just would have we wouldn't have had enough data. We would have taken more risks, taken had more guesses that we moved forward with. I think that's a hundred percent true in our case.

Jeffrey Feldberg: So a lot to think about. And I know for some of our listeners, they'll give us seven reasons to Sunday, why bootstrapping isn't the way to go and all those other things. It's just, again, whatever works for you, whatever works for the personality. And you and I happened to come from the same page of bootstrapping was the only way to go.

But let me ask you this, Jeff, we're starting to bump up against some time. You've been very generous with your time and your insights. You've done this before, but it's going to be round two with a tradition here on the Deep Wealth Podcast, where I get the privilege, the honor of asking the same wrap up question.

And it's a fun one. I'll remind you again, when you think of the movie Back to the Future, you have that magical DeLorean card that will take you to any point in time. So now, Jeff, the fun part is tomorrow morning, you'll look outside your window. Not only is the DeLorean card there, Doors open, it's curbside, it's waiting for you to hop on in what you do, and now you're [01:00:00] going to go back to any point in your life, Jeff, as a young child, a teenager, whatever point in time it would be, what are you telling your younger self in terms of life lessons or life wisdom?

Or, hey Jeff, do this, but don't do that. What would it sound like?

@RetiredFounder: It's such a great question. And I was caught, flat footed by it last time. So shame on me for not doing better research. My answer last time, which was true, which was telling myself it was going to be okay. And for anyone who's in the struggle, I'm going to start with that. I'm just going to repeat that answer.

It's going to be okay. Be confident in your ability to handle whatever life throws at you and it's going to be okay. And if you end up. With a fortune and a great outcome, it's going to be okay, too. it's not all parades and roses. So this time I'm going to choose to set the clock on the DeLorean to July of 2022, which was the timeframe where I was.

Removed from the business about four years. I own four houses, a jet airplane. I had a place on the beach. I had a place in the mountains. I had a place in the desert. I had a place in the [01:01:00] city and I had all kinds of stuff. And I was preparing for this fabulous life of retirement with this wealth, and I hit a wall and I totally underestimated how much I was going to miss the structure and the purpose and the identity that came along with the My role as the co founder and CEO of my business and anyone who's still the struggle is maybe laughing.

I'll forgive anyone if you want to hit the delete button right now. But it's, I know that's hard to understand, and I know that's hard to understand because if you would have told me 10 years ago that you're going to be in the situation you're going to be in, and you wouldn't be whistling zippity doo dah, seven by 24, 365, I would have said, that guy's a moron. And when I hit that wall, I had to confront some really hard truths that this thing I'd been chasing my entire life was not a perfect [01:02:00] panacea of a life. To get to the question, the thing I would tell myself in July of 2022 is you are not alone. And from going down a rabbit hole AJ Wasserstein who I was on the, your podcast with, lucky to participate with him, wrote a paper that changed my life.

And I learned that there were a lot of other founders that sold their business and found themselves in this state of emptiness. and it's taken a long time. And I've met a lot of interesting people and it's another podcast, but I have developed the tools and the understanding for what, happened, what expectations I had that were wrong and what to do about it.

I know it's going to sound weird for someone that hasn't sold their business yet. I would say be prepared that you're going to miss the things that you're really, you don't think you're going to miss. So that would be my advice. You're not alone.

Jeffrey Feldberg: Be prepared, love that, and so when you're telling yourself, be prepared, would you add more to that or are you just going to leave it at the two words, hey, be [01:03:00] prepared?

@RetiredFounder: I would probably put a little more flesh on it than that. There is a structure to running a company that you take for granted. You have your daily standup, you've got your weekly staff meeting, you've got your, monthly financial review, your quarterly offsite, your annual plan, whatever it is, you have a Rhythm to your life.

And when you sell and when you retire, it's gone. And you may find yourself floating in space. The meaning and identity anyone will tell you is one of the more important things. To be attached to something bigger than yourself. And I was not prepared. To not be attached to something bigger than myself, because I thought I'd be rolling around with a big pile of cash and I would have all these toys and all these neat things, and I'd be doing fabulous things with interesting people in the winner's circle of life.

And it just isn't there. And it's important to be attached to something bigger than yourself, which is what I'm working on now. And then be prepared to, to, answer who you are. What is my identity? Now that I'm not a co founder, now that I'm not a CEO of this business that you may have heard of, [01:04:00] who am I?

And it's a process, so be prepared for that, and then know that you're not alone, because it's a dirty little secret of post exit founders you're going to go through this.

Jeffrey Feldberg: Terrific advice. And before we wrap up, Jeff, if I can put you on the spot, because I know when we had that episode with AJ, you were in the process of putting together a whole new community for post exit founders, entrepreneurs, business owners. How are you doing with that? Any updates?

@RetiredFounder: Yeah, thank you for asking, it's the group is called Beyond the Finish Line I don't know when this will record, there's a really hacky website at uh, btfl. org, and in this particular case I'm targeting post exit. Post economic founders, not the people that are going to go do it again.

Not the people that are still chasing wealth. Those that have the dogs that caught the car and found themselves dissatisfied. That's that group. I think there's application I'm told for many other people who have retired from a position, whether it's a mom or a police officer or an Olympic athlete, or [01:05:00] something where you have accomplished something and now it's over.

It's a really difficult transition to make for those reasons. So, that's what I'm working on.

Jeffrey Feldberg: Terrific. And again, as we wrap things up here, all this will be in the show notes. If a listener wants to learn more about the community or have some questions for you, where's the best place online that they can find you?

@RetiredFounder: that group is going to be the Beyond the Finish Line group is btfl. org. Most of the interaction I have with people, and I welcome interaction. I, love talking to people, especially founders. I'm on Twitter at retiredfounder. And I don't post daily, but I, do, post some things.

And I've met some really interesting people. And that's a great way. I've got my messages are open. So you can. Follow or send a message, whatever it is you do. I'm fairly new to the platform, but that's where you can find me.

Jeffrey Feldberg: Perfect. Well, for our listeners out there, it's a point and click. Everything's in the show notes. And Jeff, a heartfelt thank you for your vulnerability, for being so open, for sharing the good, the bad, the not so good that went along with all this. [01:06:00] For people that are now on the same path or just shortly behind you, but catching up with where eventually they're going to be.

Thank you so much for everything that you shared. And as we love to say here at Deep Wealth, may you continue to thrive and prosper or remain healthy and safe. Thank you so much.

@RetiredFounder: Thank you. 

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. What did you think? So with all that said and as we wrap it up, I have another question for you.

Actually, it's more of a personal favor. Did you find this episode helpful? Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

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So all that said. Thank you so much for listening. And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's continue this journey together. And from the bottom of my heart, thank you so much for listening to this episode.

And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. Thank you so much. God bless.