335 AJ Wasserstein And Retired Founder

Jeffrey Feldberg: [00:00:00] Well, hello, Deep Wealth Nation, and welcome to another episode of the Deep Wealth Podcast. This episode is a fun one. We have a round table with myself and two other post exit entrepreneurs on everything you want to know about the post exit life, but you probably don't, and you wish you would have. But with this episode, we're going to do a deep dive and all that ahead of time so that you can be the benefactor of it.

Let me introduce our two guests. One of them is no stranger to the Deep Wealth community. It's AJ Wasserstein. He was on episode 39 and he's back again. He wrote another fabulous case note, which we're going to talk all about, but for the new members of Deep Wealth Nation. 

AJ Wasserstein is the Eugene F. Williams Jr. Lecturer in the practice of management at the Yale School of Management. His research, writing and teaching concentrate on search funds, entrepreneurship, programmatic acquisitions, and small businesses. AJ received the Faculty Teaching Excellence Award for outstanding teaching in elective courses at the Yale School of Management in 2022 and 2024. [00:01:00] The US Small Business Administration has recognized AJ as the small business person of the year in Connecticut.

AJ wrote a book on young adulthood that was a gift to his three children. The book's title is What Matters Most: A Young Adults Roadmap to Life. 

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.

His current project is building a [00:02:00] 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 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 [00:03:00] the only system based on a nine figure deal. That was my deal. And as 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 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 E 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, you [00:04:00] heard it in the official introduction. This is a post exit entrepreneur round table, whether you've exited, whether you're thinking about having an exit, this is everything you want to know, but probably don't know and should. We're going to have a lot of fun today.

We're welcoming back AJ Wasserstein, a friend of the Deep Wealth community who's been on before, has been really writing some prolific articles. We'll talk about that. And we also have a new guest. And for privacy reasons, this guest, who in the social media circles goes by Retired Founder, wants to keep his life private for himself and his family.

And we thought just to pick a name, we'll just pick my name Jeffrey, but we'll call him Jeff. So it's easy for AJ. So AJ, you can't go wrong either way. Jeffrey or Jeff, no other names to remember. We'll get the privacy check there. Easy to remember name, and we'll have a little bit of fun with that. So all that said AJ, first, let's start with you because it's been a while. You were back when we were double digits in terms of episode numbers. We're now triple digits. We're surpassed the 300 mark and we're [00:05:00] closing in on the 400 mark, but a lot's been going on with you.

So for our community members, particularly our new community members, what's been going on with you as I like to say, what's your story? What got you from where you were to where you are today?

A.J. Wasserstein: Yeah Jeffrey, thanks so much for inviting me back. I'm flattered. Great to talk to you again. 

I'm a former entrepreneur, so I built two business services businesses, and after exiting both of those, had an opportunity to shift into academia, and now a faculty member at the Yale School of Management, and I Write, research, study, teach, think, talk about all sorts of entrepreneurial topics and small businesses.

And one little niche y topic I'm so fascinated with, which Jeffrey, you and I have spoken about many times, is what happens to exit entrepreneurs. So all my students want to be entrepreneurs. They all want to be successful entrepreneurs. They all want a blockbuster. [00:06:00] Exit. But I think it's a really interesting question to think about what does life look like after an entrepreneur exits?

And I hope that's what we talked about today.

Jeffrey Feldberg: Terrific. And AJ, for our listeners, I mean, your journey, your first, you're being very modest. Yes, you're an entrepreneur,

A.J. Wasserstein: That's always a good way to be, right?

Jeffrey Feldberg: well, I suppose, but you had a terrific exit. You built some fantastic companies. You really made a difference out there. You had a prolific exit. And so you've been on all sides of this.

And I know back in our original episode, and we'll have a link in the show notes. In your words, you said, Jeffrey, I had this wonderful exit, but I never found my happily ever after. And that's really what began this journey and you wrote this terrific case note. And now what really took this conversation on this episode on was you came up with another follow up to that.

Absolutely love it because you asked a dozen questions to consider after selling your business. And AG, if I can take a little bit of license with that, a dozen questions to consider [00:07:00] even before selling your business, that's how important I think this is. And so we'll get there. But now let's go to our guest, Retired Founder.

And for the purposes of this episode, we're just going to call you Jeff. So retired founder, AKA Jeff, what's the story behind the story for you? What brought you from where you were to where you are right now today?

Retired Founder aka Jeff: Hey Jeffrey. Thanks. Yeah. Thanks for having me. And AJ, thanks for sharing the stage. I'll try to fill up the void of modesty here by bragging as best I can about what I've done. I'll roll back to birth, but I'll get to today in less than a minute.

Jeffrey Feldberg: Wow.

Retired Founder aka Jeff: I'm a middle class kid from the Midwest, went to public schools, been married 30 years, have three adult kids.

I'm 55. And my entrepreneurial journey started when I was A kid delivering papers all the way through starting a SaaS company. That we ended up selling for about 615 million that was in the third the third transaction with great private equity partners. I stormed into retirement thinking every day was going to be a great luxury and vacation and [00:08:00] hanging out with interesting people.

And was shocked to find out the universe cared zero, zero about my bank account and how well things were going financially. When I found AJ's case note from Yale and AJ, just, I'm going to take a side out here to thank you for writing that paper because it was truly transformative for me.

I hired a coach named Rick Eigenbrode, who's one of the authors of that paper, who helped me unpack the things I was going through and why I was so disappointed and a bit angry and frustrated. So, I've been working to replace the sense of identity and meaning and purpose that I had as the CEO of a software company.

that's where you find me today.

Jeffrey Feldberg: Interesting. Jeff, only 615 million. Come on. I think you got a, Pick your shins up there and, and only, you know, make it that much bigger. I'll jokingly say, that's wonderful.

Retired Founder aka Jeff: Thank you. I told you I'd filled the modesty void that AJ left. It was a fabulous outcome. One of the things I've observed from other friends who have Exited businesses. They end up talking a lot about more about their [00:09:00] feelings than the dollars. So even people who exited for spectacular amounts of money end up disappointed somehow that somehow they weren't recognized or someone didn't get treated fairly, or they had to like myself, fire their co founder or something that went along the way.

So the money is great, but that's the thing you're focused on prior. To the transaction. Once you get on the other side of the transaction, it's more about the feelings than the dollars.

Jeffrey Feldberg: Absolutely. And so AJ, for yourself, because I know after your experience, you went through your own journey and. For our listeners out there, come on, whoever feels sorry for someone who really has more money and time than they know what to do with all these zeros in the bank account, but they're bored at home sitting in their pajamas.

No one wants to come out and play because they're living their lives. And AJ, that was something like or that journey was very similar for you. You went through something like that. And eventually you found yourself at the Yale School of Management, and that's where your first case note, what's next?

The Entrepreneur's Epilogue and the Paradox of Success. You put that [00:10:00] wonderful piece together with your co authors and got that out there. But again, for the benefit of our listeners and to really build off of what Jeff was saying, what was your journey like in terms of the emotions, the feelings, because you climbed the mountain, you took your moon shot, you went to the moon, and now it's the day after, what's going on?

A.J. Wasserstein: Yeah. Initially, I think there's sort of elation because push this boulder to the top of the mountain. You get across the finish line. There's all these celebratory events and emotions. And but for me personally. And I've discovered this talking with lots of other exit entrepreneurs, I think there's often a sense of loss this sort of baby that you built and nurtured and shepherded over decades is all of a sudden gone you lose structure, meaning, and identity, so there's no rhythm to your day anymore, doesn't matter what time you get up, and You sort of confuse what your calling and purpose is in life.

And when you're a CEO or an [00:11:00] entrepreneur, you sort of identify as, hey, I'm the leader of the ABC company. I'm in the XYZ industry. And you're, so I have this, Persona, for better or for worse, that's sort of anchored and centered on your professional role. And when you exit business, all that evaporates.

And I was really confused. I was lost. I might even say I was depressed. I don't know if I knew that language or understood what that meant, And as Jeff said earlier, no one cares. My wife was still working. My kids went to school. My friends had jobs and I sort of didn't know what to do with myself.

And it took me a lot of time just to create space between the company, the exit and moving forward and sort of decompressing, letting go of the past, trying to figure out what the future was. And that was an emotional process for me.

Jeffrey Feldberg: And for both of you, and by the way, AJ and Jeff, everything that you've both mentioned, I've been there as [00:12:00] well. Count me in, because I know for me, no one ever talks about this. You don't really read about it. And my focus was crossing the finish line. The next day, the day after wasn't even top of mind. I just wanted to get through this experience, this thing called a liquidity event.

It really is a marathon, it's very long. It's financial security on the line, your independence, your legacy, the company's success, the next chapter. All that pressure is built up that to think about next days or next steps afterwards, didn't come to me. And really that happened at my own expense. It was huge mistakes that happened afterwards.

And very similar to both of you, depression, perhaps feeling down, you've, Kind of gone like what the astronauts said, they landed on the moon, did something never, no one else had ever done before, in our case, something that we'd never done before. And then you get back and it's life as usual, but it really isn't.

But I want to pick up on what some of our listeners might be saying to themselves, because for all of us on this call, imagine a listener who's saying, let me get this straight, guys. You had a fabulous exit. You have all these [00:13:00] zeros in the bank account. You can do whatever you want to do. The phone's not ringing off the hook.

You don't have to answer a gazillion emails. You don't have the pressure. You can sleep in. You can go wherever you want to go, buy whatever you want to buy. And you're not happy. You're bored. Give me that problem because I'll gladly take that relative to where I am today. What would you say to that narrative, to that listener?

Retired Founder aka Jeff: First of all, I would be in violent agreement with that listener had I been in their position. There's no way I would have anticipated the post exit ennui that fell upon me and I believe. to both of you as well, the world has an expectation of you that you're going to do something bigger and better next.

And deep down for me, in my experience, that was a draw, but it was something I was also drawn to. Terrified to pursue if you picture a spectrum of, okay, now that I've sold a company for this much, or now that I've accomplished this thing, certainly I'm obligated to go do something bigger and better [00:14:00] next time.

Maybe we can work on climate change or hunger. On the other end of the spectrum is living a life of comfort and luxury where nothing gets accomplished. It's terrifying to think about either end of that for me is being comfortable and Living a basic life of luxury, sleeping in, all the things you mentioned, not being obligated to answer emails.

It sounds terribly compelling, but I think on my deathbed, for me, that would not be enough. On the other side, I'm well aware how hard it is to start something from scratch and how easy it would be to quit as soon as it got hard. it can be a bit paralyzing to sit in the, middle of those spaces.

Jeffrey Feldberg: Absolutely. Jeff, as you went through that, From the early days. when did it dawn upon you? Hey, this is a different chapter. This is very different. This is nothing like I imagined. Oh my goodness, what am I going to do now?

Retired Founder aka Jeff: Yeah, this is embarrassing, actually, it took so long. It was three years, almost four years into retirement where I hit a wall, I had purchased four houses because I felt like [00:15:00] I needed to have one in the city and in the desert and in the mountain and on the beach. Of course, I bought a jet I was just spending a lot of time preparing for this fabulous life that I was going to lead.

And then when I got through all of projects and the possessions, I realized, A, this wasn't ever going to make me happy. And I was out of things. To do, and B, I didn't have the energy to go pursue this this vague dream of happily ever after. There was no one, guess the analogy I use is I saved up for all these years to buy the car of my dreams and I got it and it was so much better than I thought it would be, but I didn't have anywhere to go or anyone to ride with.

Jeffrey Feldberg: And again, for our listeners out there, Jeff, who are hearing you talk about this, they're saying, wait a minute, you've got a private jet. You have a house on the four different seasons, so you can be wherever, whenever. And that wasn't enough. That didn't fill you up. That didn't buy you the happiness and the happily ever after.

What's going on with that? What would you say to that listener?

Retired Founder aka Jeff: I would say I understand if you're rolling your eyes and how ridiculous it sounds. Now, let me beam you into [00:16:00] actual moments of a person that has four houses and a plane. The fourth house on the beach you haven't been to in three months you show up, you get in at 10 o'clock, you open the door, everything is broken.

Everything is broken. Salt water eats houses. The smoke detector's beeping. The garbage disposal smells. There's a weird note on the door the Wi Fi doesn't work. And you're wondering, what the hell am I doing? Why did I do this? When you own an airplane, it sounds really great. 

You're just going to pop in this thing and jet away with friends to cool locations. Well, your friends have jobs. They can't just pick up and go to Bermuda on a minute's notice. Also because you're trying to offset the costs of your airplane. You have it in a charter fleet and maybe I'm in Scottsdale, Arizona, but the plane is running between New York and Boca making, making you money.

Now you've got to summon the plane and have it come to you and then have it sit there while you're on the beach. Also, someone broke your tray table. Which for some odd reason costs 17, 000 to fix, and one of your pilots is [00:17:00] sick. So the spreadsheet you may put together, and I don't want to talk about planes.

People talk about planes way too much, but I'll just try to save anyone the angst. You can torture a spreadsheet to tell you anything you want it to confess to about owning a plane, but the cell you can't fill out is what is the value of head trash? And in my experience, it was much greater. Then fuel, hangar, pilots, repairs, training, GPS, any of the other things are pale in comparison to head trash.

And I guess just to sort of sum up, and I'm sorry for the long winded answer, things don't bring happiness. People and purpose bring happiness. Things are nice.

Jeffrey Feldberg: Well said, Jeff. And for my benefit, perhaps benefit of the listeners, when you say head trash, what do you mean exactly by head trash and what does that mean to you?

Retired Founder aka Jeff: It means that the thoughts that invade your space that could be thinking about what do I want to do today? How do I maximize the value of this life that I've created? That's being on [00:18:00] offense. It's having a goal. It's moving toward it. It's working with people you like and trust in pursuit of something important.

That's being on offense and that's moving forward. Every time the phone rings. And the landing gear has a problem on your plane. And for some reason, that's 110, 000 and the parts not in it's trash. It's trash in the head that is not being used. I have a limited CPU. So my CPU is now trying to figure out, well, how are we going to get this landing gear part or the landing gear?

How am I going to replace the smoke detector in in this foyer? That's 30 feet high. It's non productive time. that extends up. I'm just talking about houses and plans for me. That's extended to making a bunch of investments that I probably shouldn't have made tracking down K 1s, wondering what's happening with a founder that disappeared, all of the things that you think will bring you joy actually net out to negative, a lot of them in my experience on the spectrum of joy and pain.

And they're not things you would have expected to bring more suffering than joy.

Jeffrey Feldberg: So what would be things, Jeff, in your case, [00:19:00] you do these things to what you thought would bring you happiness, but it's these very things that are bringing you down. They're not having you in that happy place. You're dealing with all these issues, these problems, these headaches. Your mind is wrapped around that instead of the more important things.

Retired Founder aka Jeff: I think that's exactly right. And again my, experience, one of the big flaws in my retirement plan was thinking I would have high quality opportunities finding me. I thought, my company would want to have my input on things. They really didn't. I thought that I would be, active with nonprofits and that's difficult as well for a founder to be able to just check money at something or be able to operate it in a space that's more slow and bureaucratic. So all of it uh, enlightenment in an ongoing process.

Jeffrey Feldberg: Yeah, I get you there. I've been there and sadly done that as well. And AJ, what about yourself? So as you're hearing Jeff talk about this, what's going on through your experiences, through your lenses, your journey that got you from the post exit in the early days to where you are now, what was going on as Jeff was talking?

A.J. Wasserstein: Yeah, well, there's this psychological term called the Arrival Fallacy. [00:20:00] So we've probably all experienced this where you sort of pine and desire something and then when you achieve it, in, in this conversation, the exit, it's often not as good as we built it up to be. So there's this sort of anticlimactic. feeling to capturing the goal, the what drives many people, certainly me, sounds like it drives you and Jeff as well, is the pursuit of the goal the diligent work, the teamwork, the collaboration, the incremental progress towards achieving something. It's sort of about the journey and actually winning the goal or capturing the goal is Now, it's not as much fun or satisfying or fulfilling. I think this sort of post exit phenomena is sort of this dark secret, a little bit of an underbelly of the entrepreneurial story. so entrepreneurship this having moment in all sorts of circles and I'm guilty as an academic of Chattering about the virtues of [00:21:00] being an entrepreneur and media celebrates entrepreneurs but there's this sort of underbelly of what happens after you achieve what you want, you're successful, you exit.

And it's always sort of this implication of happily ever after. And I'm not saying it can't be happily ever after, but it's a different happily ever after. It might be sort of not what you expect, but the notion of. Living a Life of Leisure. was talking about toys and luxury homes and experience.

Look, I'm a huge fan. That's called a vacation. And it's wonderful for a week or two weeks or maybe even a month, but that's not a lifetime. So, I wrote my first paper. I think I wrote this on what's next. Saturday is an awesome day of the week when there's Monday through Friday. If every day is Saturday.

It's not so special. And when you're a post secondary entrepreneur, you can structure your life for every day to Saturday, and that might be the perfect answer for six [00:22:00] months, a year, or even five years, but at some point you need Monday through Friday. You need some purpose. need to be pushing the boulder up the hill again.

You need to find your second column and it might not be the same thing. It might not be as big. It might be different. But you sort of need to wake up in the morning with a purpose and an identity and know who you are and living a life of leisure isn't that. So you need to find that next calling and that takes introspection.

Intentionality and time.

Jeffrey Feldberg: Well said. And the human condition at its very best, we get what we want, and then, well, maybe there's more, maybe there's other things that are going beyond that, and I suppose it would be like, and both of you can say, Jeffrey, you're on base or off base, if you happen to like steak, and every now and again you go out, you have a terrific steak, but now you're having steak every single day, every single evening for dinner, you're having steak, at one point it's going to be, oh my goodness, I have to have steak again?

I'm bored of that. So welcome to the human condition.

A.J. Wasserstein: What's so disorienting about [00:23:00] being a post-exit entrepreneur, I think Jeff hit upon this when he talked about his friends couldn't play with him because they all had jobs, you're going through something asynchronously, so you're sort of this odd duck, and most places in America, people in their 20s 30s, 40s, and 50s, wake up and go to work.

And when all of a sudden you don't either have to go to work or you're in a situation where you're not going to work, a weird place to be. When all your friends sort of are in a sort of what I'll call a normal mode, and you're in this So, if you're in that weird post exit mode, it makes it really hard to go through that process without a cohort.

Jeffrey Feldberg: Absolutely. And AJ, in the what's next case note that you put together, what really resonated with me is the ritual that we build. We all have seasons and in the business, we know more or less what I'm going to be doing, not only on the day, the week, the month, the quarter of the year, it's more or less planned out because we have these rituals.

We know who we're going to be speaking with, [00:24:00] the people that we're spending time with in the office, the team members, they're not just employees, a lot of them are friends and we know what we're going to be doing. And then when you take that away, You now have this vacuum, this absence. So, AJ, I want to ask you though, the What's Next, the case note, for me, that was really well done.

It could have finished right there and that could have been it, and that would be wonderful. What was it that had you come up with a dozen questions to consider after selling a business?

A.J. Wasserstein: Yeah, so I was talking with a friend who was preparing something for a YPO group, Young Presidents Organization, and a couple of those folks had exits and were, So figuring out and struggling what to do with their next chapter. Most of them were slightly older than I was when I first exited. I was 40 years old when I sold my first company.

But they're sort of thinking about their third chapter of life and in preparation for that call, helping this friend. I thought of a whole bunch of questions that I [00:25:00] wish I asked myself after I sold my business and my friends gave me positive feedback that these were worthy questions to consider.

So after talking with this person I turned it into a case note and Hope it helps people. So look I want to be clear. I don't want to speak for Jeff. I can only speak for myself. Time and wealth are really wonderful gifts, especially if you have health. But so no sympathy for these post exit entrepreneurs but I'm trying to create some body of work that helps people.

them understand where they are and move forward in a very positive, constructive way and make the most of the blessings and gifts that they both earned and were lucky enough to walk into. So these dozen questions to consider after exiting a business are hopefully some thought provoking themes that will help people Get through this post exit malaise quicker, [00:26:00] better, more elegantly, and with more purpose than I did.

Jeffrey Feldberg: Absolutely. And again, for our listeners in the show notes, we'll have links to both the case note for what's next. Also, AJ's latest, a dozen questions to consider after selling a business, to go through that and sharing with both of you. And again, looking at your own experiences, looking at how I would give myself.

Not only in F, if I were rating myself on my post exit experience of my lack of preparation, what I didn't know, and all the mistakes that came afterwards, it was just a terrible experience. I could only hope, I can only hope that the younger Jeffrey Who would have had the opportunity to read both case notes, which weren't obviously there at the time.

But I can only hope that if they were there and I had read them, that it would have put me on a very different path. Now can't change that maybe in a multi universe that's happened and terrific, but in this life anyways, didn't happen. And as I shared on many episodes, some of the mistakes, my biggest mistakes came post exit, not pre exit.

And it took me many years to clean those up. [00:27:00] In fact, still cleaning some of those up, even though the exit is really a distant memory. So AJ, before we put it back over to Jeff. When you look at the dozen questions, this may not be a fair question to ask you. It may be asking you to choose your favorite child, but from the dozen questions, is there one question that really stands out for you?

And again, our listeners click on the link, you can see all 12 of them, and there's an incredible job of taking each one and explaining it. But AJ, to put you on the hot seat, is there one that really resonates more than the others?

A.J. Wasserstein: I don't know if that's fair, Jeffrey. So if you gave me four, can I take four? That would focus on this effort.

Jeffrey Feldberg: Love it. Yeah. Let's pick your top questions. Yeah.

A.J. Wasserstein: Okay. So I think shifting from exit into this post exit, thinking about what your eulogy is going to be. So if you're lucky enough to have time, wealth, and health in your thirties, forties, and fifties, so project forward, what do you want the summary of your life to be?

I think this is a fascinating question. I don't know if we're going to talk about Jeffrey you're our [00:28:00] guide. But many post exit entrepreneurs dedicate themselves to accumulating more wealth. And I think it's really fascinating to think, how would life be different if you had twice as much money or five times as much money?

I think figuring out what your new scorecard is. We all operate with scorecards in life. Some are personal, some are professional. But when you're a post sex entrepreneur, it's not about being the biggest company. It's not about X dollars. It's not about winning that new customer. What's your scorecard?

And then two more being cognizant about how you're the same and different than you were 25 years ago. So I became an entrepreneur when I was 24 years old. And despite having the same name and roughly the same face and body, I'm a very different person than I was when I was 24 years old.

So what new skills, what new emotions do you have? And this really focuses on Are you capable of being an entrepreneur and CEO again in your 50s or 60s which many people aspire to? [00:29:00] Then finally, this Japanese notion of ikigai.

So what is your ikigai? And that's this Japanese concept of what is your reason for living? And being on vacation is not a reason for living.

Jeffrey Feldberg: Absolutely. All about purpose. So if I'm looking at that, AJ, and again, for our listeners in the show notes, when you look at the article or the case note, it's question one, what do I want my eulogy to be? Then you went on to question three, what is my scorecard now? Then question 11, how am I the same and different from who I was 25 years ago?

And then question 12, what is my Ikigi? From that Japanese concept. Love that. And if you picture a Venn diagram of all these different areas overlapping, it's where they all overlap. That's a sweet spot for you. What's going on there. So AJ, why those four questions? You could have picked any other number of questions from the 12.

What is it about those four collectively?

 I don't get paid by the word, but sometimes I feel like I have a lot to say because my wife [00:30:00] and kids won't listen to me. But I think those questions were the essence of the post exit entrepreneur experience. But sort of this, if you have the luxury of designing your life, any way that you want, you have this blank piece of paper and, every post exit Entrepreneur is different, but if are largely no financial constraints, how are you going to build your life?

A.J. Wasserstein: So do you want that life to be? And your eulogy sums it up. So what people say about you at the end of the day is a reflection of the choices you made and the person you are. And can only speak for myself, but if people are speaking about me in the past tense, I hope it's not, hope it's not about my role as an entrepreneur as an investor, as an educator.

I, I don't want it to be those parts of my life. I hope it's about my role as a husband, a father, a friend the person I was, the character I had, [00:31:00] how I helped people, how I made people smile and laugh. Probably not as funny as I'd like to think I am, but maybe but really capturing the.

this is this David Brooks notion of, are you building a life of accomplishment or a life of character? I don't want my story to be about accomplishment. I want it to be about character. So, if you have the luxury of designing your life any way you want, what are you orienting around? So, then the whole money thing yeah, I just think it's really interesting when people figuratively won the lottery and they wake up the next day and say, I want more.

And how is that really going to change your life? And is it introducing complexity or simplicity? Is it really going to make you happy? I mean, if you're not happy with 50 or a hundred million dollars, I'm not sure you can be happier with 150 or 200 million dollars. so why are people dedicating so much time?

Then the, the scorecard, like, what's your operating metric when you wake up? [00:32:00] Just being cognizant of how you're the same and different 25 years ago and then this, what's your reason for living and purpose, the Ikigai thing.

Jeffrey Feldberg: And one other question, AJ, and then Jeff, we're going to put it over to you for some questions as well. When you're looking at these four questions in particular, your younger self, had you asked those questions before you even began the exit process, do you think you would have found your happily ever after or some version of that to avoid the journey that you went through?

What do you think?

A.J. Wasserstein: Yeah, Jeffrey, I cringe at my younger self sometimes with such unbridled ambition and focus on building a big business and all that type of stuff. I'm not sure that was the healthiest scorecard or the healthiest version of who I am. Yeah I think the trick is when you're thinking about selling a business, you're so wrapped up in the business, you're running the business, which is a full time job, you're trying to exit the business, which is a full time job, you're filled with ego, bankers, lawyers, buyers, everybody's fawning you to sprint through [00:33:00] the finish line and you're full of yourself.

I'm not sure you're ready you're in a place where you can begin to think about the next chapter and what the epilogue is all about. Maybe the most enlightened and progressive entrepreneurs are, I wasn't I didn't think about any of that, I was just so focused on running the machine and getting across the finish line in the best possible way.

So yeah I wish I mean, I've written some of these things, Jeffrey, and I've spoken about this to various groups because I wish. Someone made me aware that the exit wasn't about the financial stuff, the estate planning stuff, the 20th item in the purchase and sales agreement. It was really about, as Jeff said earlier, the emotions, the feelings, the next calling, and I was completely unprepared.

So, I wish I had some of this stuff. I didn't find it. I'm not sure I was ready for I hope some of the work [00:34:00] I've created is helpful to other people.

Jeffrey Feldberg: And so Jeff, you're hearing us talk and AJ is sharing his thoughts. Perhaps you had a chance to reflect on some of that on your journey and where you are today. So what are your thoughts? I mean, from the dozen questions that are there and having gone through them yourself, what's your narrative?

Having looked at those questions, would they have made a difference for you? Would they not? Does one or two or three or four, in this case, resonate more for you than some of the others?

Retired Founder aka Jeff: Yeah. I, want to ask if we could turn this into a six hour podcast, cause I'd love to have AJ follow up on everything he just said. And I want to acknowledge this is a journey and AJ, you're you're so much farther along path but I'm on the path. So thank you for sharing. I know it's been extremely valuable for me and I know it's going to be valuable to Jeffrey's listeners.

So I've made a few notes. To bring up one of them is the question, why are you still working? Why are you still chasing money? I've come across, and I [00:35:00] don't have the answer for this one, but I've come across so many people that have so much more money. And I'm not judging, but they choose to spend their time with a family office sitting behind a desk with a big pile of cash like Scrooge McDuck.

And they're trying to build it higher and higher. And God bless them. If that's what your purpose is in the world, it just, it wasn't mine. I would also say to those who have found joy playing golf every day. or doing something that's recreational and they love it every day. I have a deep hatred of these guys.

So let me just say it out loud. This is why it could be anonymous. I hate you guys that can play golf. You play every day. And then you play nine extra holes and then you sit and have a drink and you talk about the shot you hit and the one you wish you hit and what time we're playing tomorrow. I hate you guys, but I didn't fall into that particular camp.

talking about scoreboards for a minute, I haven't figured this out, but I think it's absolutely true. One of the things, maybe the [00:36:00] thing I missed most about my prior life was working toward an important objective with people I liked and respected and trusted. it's really hard to replace that, especially with golf.

What are you guys doing? Come on. But directionally, a scoreboard, not a scoreboard, but an indicator for me is energy. So rather than thinking about things with a dollar sign. I think about things that give me energy and that take energy from me. If you're energetic about pulling weeds in the yard, that's so much better than being unenthusiastic about sitting on a board that's solving homelessness for me, believe.

So that's the direction of a scoreboard I try to use. you guys have just touched on a bunch of other things. You've both used this idea of About crossing the finish line, and I'm working to set up a group of post exit, post economic. Entrepreneurs, which I'm using the title Beyond the Finish Line.

So shameless plug [00:37:00] for btfl. org, which should be online here within a few days, probably by the time this posts and I could go on and on I've picked up a few really interesting nuggets, I think from AJ's work and from the other work that I've done, if it's useful, I'd be glad to share them, but I don't want to hog the air here.

Jeffrey Feldberg: Well, some terrific insights there. I'm going to put my thesis out there and both of you can agree or disagree. And AJ, as you know, offline, I've spoken about your case note, absolutely loved. And we built that into the 90 day Deep Wealth Mastery or Scale for Ultimate Sales system. And we actually take the post exit, which is actually step number 10 in our nine step roadmap.

And we make that the very first starting point. The journey when you're going through Deep Wealth Mastery, because we say, why don't we take not the final exit? I mean, the final exit is when we all leave this earth, but the business exit, if that's the final exit in business, potentially, why don't we start there and then work backwards, but put that up at the front and our thesis has been, and we've seen this and you can both agree or disagree that if we know about this ahead of time, [00:38:00] we can begin the process of experimenting and trying out post exit activities now.

Geez, I really like that one. Oh, that one I couldn't stand. Jeff, that would be your comparison to golf. Man, I tried that golf. I cannot do that. That's definitely not going to be post exit for me. Let me find something else to fill my time. That by the time you get to your post exit, You have a ritual, you have a momentum.

AJ, from the case note, I've filled up some of that white space. And I'm going to welcome white space. It's not going to be a new and foreign concept to me. So with that in mind, and again, you can agree or disagree with that, but I'm wondering, and we'll never know the answer to this question, but your best guess, if you would have had the dozen questions, if you would have had the what's next, case note, would you have, built your business, your processes, even the liquidity event differently, knowing what's ahead for you in the post exit?

Would that have made a difference for you or not at all?

Retired Founder aka Jeff: I'm going to give you the honest answer. No, I would have thought oh, I'm reading about this person that is beyond the finish line, made all the [00:39:00] money, and somehow they're unhappy. My honest assessment is I would have thought, what a moron. Put me in that person's position, hand me the wallet, let me show you how this is done.

 I will say answer your question a little sideways, had that information, perhaps the information I would have, benefited from was this concept of your life as a mosaic. So if you think about your life as one big picture that represents your life when you're working and running a company, there's this great big tile in the middle and it's, it's.

Retired Founder, Jeff founder, CEO of this software company that you probably haven't heard of, this is who I am. This is what I do. It's a giant tile in the middle. And yeah, there's other tiles on the side. Of course, you've got your friends, your family, your hobbies, but when you lose that, it's more than white space.

It's a big gaping hole. And part of the work I did was understanding this and giving permission to replace that big gaping hole with other tiles that serve. [00:40:00] The big picture. And it's okay. And it's okay that one of the things in golf is part of my life. Skiing is part of my life. Hiking is part of my life.

I'm still seeking and, AJ has done a great job of this, finding his role as a professor is maybe a medium sized tile that becomes your purpose, but it does not have to be curing cancer.

Jeffrey Feldberg: Interesting. So the honest answer, and you've been very open and transparent, Jeff, is sure, perhaps I would think about that, but it really wouldn't make a difference. I would get to it after I did my liquidity event. Once I started the post exit life, I had to begin the work, and that's what would really work best for me.

Am I getting that right?

Retired Founder aka Jeff: You're absolutely right. I'd love to give you a convenient answer that yes, I wish I would've read AJ's paper. So, had no idea was going to be spending a couple of years uh, honestly, I think speculating for other founders can, you know, have their own, their own viewpoint on this, but knowing myself, I would have said that guy's a idiot. watch me, go.

A.J. Wasserstein: Jeff, I apologize for insulting you, but you're not the first person to have called me an idiot. So, so if you want [00:41:00] that title or claim, it's not yours. 

Retired Founder aka Jeff: you both understand that DNA of a founder, am I off base on that? That someone would have been enlightened and said, you know what? I am going to spend more time being present for my kids because I'm not going to need all this money, or I'm not going to struggle with purpose and identity.

Yeah. It's it's just not something that's part of the wiring disagree if you think I'm off base.

A.J. Wasserstein: don't think you're wrong, Jeff, you can still encourage people to think, contemplate, consider and hear the stories of people who have traveled in their same path and are further down the road. It doesn't mean they're ready. It doesn't mean they're going to embrace or accept, but you planted the seed.

Look I teach in one of my courses, I do the, what's next, a sense about Entrepreneurs who have exited and what that feels like for entrepreneurs. And students have a hard time sort of reconciling what that is. sort of, I don't have grandchildren. I'm unaware that either of you have grandchildren, but [00:42:00] it's sort of like when people tell you how great grandchildren are, Well, until you have your own grandchildren, it's hard to really understand what that means.

And so when I teach this to my MBA students I'm just planting the seed. I'm just exposing them to the ideas and concepts and material. And when they're ready to grab that tool in their toolbox, they'll know the tool exists. might not fit them yet, but at some point, maybe they'll grab the tool.

It no differently that for sitting CEOs or entrepreneurs that you can introduce the tool to them, the concept, they might not be ready, but that's okay. When they're ready, they'll know it's there.

Jeffrey Feldberg: That's interesting, you know, as both of you are talking about this so for myself, I feel preparing in advance and that's just how I work. And what I love about all this, we're all unique.

We're very different. What works for me won't work for someone else and vice versa. So Jeff, you're sharing, Hey, yeah, give me these questions ahead of time. I don't think it really would have made a difference. I'm on the opposite end of the spectrum on that. Yeah, give me these questions.[00:43:00]

Absolutely would have made a difference. And I don't know if it would have changed the liquidity event in any way. It would have changed some of the time that I allocated leading up to the liquidity event in terms of preparing for the day after and the post exit life. And so some food for thought there for the listeners, but that's the beautiful thing about this.

Know yourself. Know your personality, what works, what doesn't work, and then make it your own and apply it. And AJ, let me put that back to you to put you back in the hot seat for just a moment of, had you known these questions, younger AJ, somehow the present day AJ transplanted these questions and you had this while you're still building the business.

Would it have made a difference for you? Would you have done anything differently?

A.J. Wasserstein: don't know. I'd like to think I would have at least considered and contemplated, but my vision for post exit life I don't know, Jeff, maybe every post exit entrepreneur goes through the cycle where they think they want to be on boards. They want to make investments. Maybe they want to start another business but it was very commercially centric.

[00:44:00] And there were a bunch of activities that were adjacencies to being a CEO. And I tried a bunch of those. And just saying for me, they weren't all very fulfilling. Being a CEO felt really fulfilling for me. just felt like I was orchestrating this organization and As Jeff said earlier, you're working towards a goal with people you like, care about, trust, and so this machine moving forward and people are developing.

And I mean, that was just really satisfying in an emotional and intellectual way. And being an investor or a board member, like That never felt the same for me. Like, as a CEO, I felt, some ways, I felt it was very much about me, but in other ways, it felt like I was serving, because I was creating this culture with opportunities for team members, and they were thriving and growing and felt really good about everything we were doing.

That was neat. And now I'm just super lucky finally found a place in my post exit journey as an [00:45:00] educator where I feel like I'm serving students which is a tremendous privilege and luxury. And also through my writing, I'm reaching all sorts of people around the world and hopefully being a positive influence in serving them through the stuff I write.

But I'm not sure I was ready for that initially. thought, My initial perception of what post exit life was yeah, it was more along investing, boards, business, and,

that was my initial take. And not that there's anything wrong with it. It just wasn't the quite perfect fit for me, no different than what is saying about golf.

I'm not a golfer, but Jeff, mean, you might very much enjoy playing golf once a week. You just don't want to play it 10 times a week.

Retired Founder aka Jeff: That's right. And I just want to clarify from a prior point I am calling myself an idiot. The prior version of me 10 years ago would have looked at me going through this struggle and called him an idiot. You, the authors of the paper were the enlightened [00:46:00] group that helped this idiot become 

A.J. Wasserstein: I'm your idiot peer, Jeff. That's fine.

Retired Founder aka Jeff: Okay, no you're so far ahead of me I continue to be impressed with you. And just to follow on and using the mosaic concept, maybe that's an exercise that, that might be interesting for an entrepreneur pre exit. Who's still not going to listen, but to think about, okay, what does happily ever after really mean?

How does that manifest after the six months where you've, you've eaten all the steak using Jeffrey's point, you've, you've been on a boat, you've been on all the four seasons you want to be in. You've done all this stuff, like what happens then? What happens on a Thursday, five years after you exit?

And if I would have put together my theoretical mosaic. I would have thought a few of the same things that you mentioned. One, that I would sit on boards. I never really thought about it, but it's just something people say. Well, people are going to want you to sit on boards. Well, guess what? Awful.

It's absolutely awful to me. It's right there in the title. Sit. Sit. Sit on a board. [00:47:00] So you're in a room for seven hours of PowerPoint. And you're watching other people do stuff. I'm again, just my experience, your mileage may vary, but I'm a founder. I want to do stuff. I don't want to watch other people do stuff.

And I certainly don't want to have seven hours of PowerPoint in my day. It It was miserable. The nonprofit thing is another example. I would have thought I'd have a big tile in my mosaic to give back. And so for me, we found it relatively unsatisfying to just write a check. as uh, Rick says, you know, they, they want your time, your talent and your treasure.

But in reality it's your treasure and then they want your friend's treasure as well. And that's okay. That's how those exist, but they also operate at a speed and a level of organization and bureaucracy. That's very frustrating for a founder. And then finally the investing thing, which I thought, boy, I'm really going to enjoy investing in early stage Companies.

It just wasn't true. definitely my ego was out of whack here thinking my knowledge would be valued. But in reality, you're just writing checks for lottery tickets that probably aren't going to cash. So by [00:48:00] the way, I'm on a quest to consolidate my 40. I have about 40 different investments into a handful of index ETFs.

And they never call me, they never send me a K 1, they never do a capital call. And I think I'm going to be happier with that.

Jeffrey Feldberg: So true. When AJ giving you feedback as a post exit entrepreneur, the case note, the 12 questions in the absence of that, and Jeff, to your point, the myths, the social programming that I bought into was after selling a company, after getting to a certain financial level, you sit on boards, you become a big time philanthropic individual, you manage your own money and yeah, you have people around you, but you're really responsible for doing all those things.

And those are, to your point, Jeff, all the things. I don't really like, it doesn't really move the dial for me, but I thought that's what's expected of me. And that's the role that I should begin to fill, even though that's nothing to do with me. And so for our listeners, when you go through the case notes, in many ways, it's going to expand your horizons of what you can and quote unquote [00:49:00] can't do to really whatever's going to make you happy.

Whatever is going to have you give and continue to give your gift to the world, these are the tools that are going to be able to help you do that. And you don't have to buy into the traditional monologue and social programming, which is often wrong of what's expected of you. And that's what I found really powerful about that. So, having said all that, I'm sure we've confused the listeners in some ways of what they should and shouldn't do, and hey, really do what you want to do, and here's some guidelines for you. Having gone through your own post exits, and having had the benefit of AJ's penmanship, him and his co authors, of these two terrific case notes, Jeff, maybe start with you.

What would be your thoughts, insights, advice, or wisdom, pick anyone or all the above for our listeners coming out of this episode? How should they be viewing what they're doing right now, their post exit, based on what you know, where you've been, but also where you haven't been as a result of our discussion?

Retired Founder aka Jeff: Great question. I think AJ is right to have planted the seed and been thinking about more specifics of how you're going [00:50:00] to fill your day with meaning and purpose. The other thing that seems so obvious, but was a big unlock for me and I'm not that bright, I guess, cause it took several years to get there was to recognize the subroutines.

That were happening in my brain that made me successful as the CEO and founder of a security software company that were killing me. Post exit. I'll give you an example. One of the things you need to do as a CEO of a security software company is find things that are wrong and fix them right away. That seems valuable, right?

If you're an investor in that company, that seems valuable. Now go on vacation with that guy. Now get into The suite at the four seasons. And instead of looking at the ocean, you're trying to figure out where the rattle is coming from the air conditioning unit or something. It's miserable. I was an optimizer.

I had to have everything done just right. I was good at deferred gratification. I was great at moving through the thing that I was doing as quickly as possible so I could get to the next thing. [00:51:00] I've got a list of 15 of these I won't torture you with, but it was valuable to me to recognize, Oh, that's that subroutine that I used for 30 years.

Building, building wealth, and I need to shut that thing down to the extent that I can. I would also add in the concept separately I think AJ touched on this or Jeffrey, you touched on this of optimal complexity. Having nothing is too little, but having 40 different investments and a whole bunch of, things you're having to track and administer and maintain there's a spot in the middle there.

And I think a lot of us overshoot it on one end or the other.

Jeffrey Feldberg: Absolutely. And Jeff, to your point, and again, coming out of post exit, I didn't have AJ's wonderful insights and wisdom and case notes. I was just falling in line with what was expected of me. Believe it or not, I had this huge nine figure exit. But to me, it was imposter syndrome. I didn't feel I was worthy.

When I was at social events, Oh, Jeffrey, what do you do? Well, I want to say, I sit at home in my pajamas all day [00:52:00] and I just kind of bored, not doing a heck of a lot. That doesn't get the right kind of attraction . So on that side of things, it's just feeling like, okay, how am I going to prove myself?

And Jeff, to your point, maybe I should start a company. Maybe I should start another market disruption. Maybe I should work on the next billion dollar exit. Since I've had this one, Why not go big or go home as the saying goes, and really not having the bookends of doing it the right way, the healthy way for next steps and post exit.

But let me put that on pause. So AJ, back over to you as far listeners, they've been listening to our fireside chat with the three of us, what would be one or two things that you want them to take away from this of what we spoke about, or maybe what we even haven't spoken about, but they should know about this.

A.J. Wasserstein: Yeah, I think the biggest mistake most people make after they exit a company is

So the most important thing from my field research, my personal experience, after you exit a business, is to resist the temptation to getting on [00:53:00] boards, starting a new business, buying new homes, changing your personal, life, the best thing to do is Nothing. Just be pause, take a sabbatical.

If you could meditate, if you could walk and think, but just let go. Celebrate the event, mourn the loss, but resist the temptation to do anything while you're still very raw and vulnerable. So, That's sort of just pausing. And some ways, after a big exit, there's a moment when people want you to be on boards and make investments and not for profits and that's all very flattering. And you're susceptible to grabbing anything because you sort of feel like, oh, I'm not sure I like sitting in my pajamas all day at home. But signing up for things with a long tail in a moment of vulnerability might not be the best thing to do. So pausing, I think, is really important.

And then exploring these questions these dozen [00:54:00] questions that we've written about. I think really defining your values In the first note, this what's next, Jeffrey, I wrote about pause, reflect, operationalize, think, but reflecting is defining your values, talking with mentors, coaches.

Professional resources about what you're about, what your path and game plan can be figuring out different career arcs what that might be figuring out what your IKIGAI is is important, and then operationalizing, I think, these It's really helpful if you could take trial probes, so dip your toe into something without overcommitting.

So if you do want to be on a board, that's awesome. Say, hey, I'm going to come to two board meetings, and then after two board meetings, let's reevaluate. I might say it's not for me, or you could tell me it's not for you, but have a graceful off ramp before you over Commit. Most board terms are pick whatever, three years, five years, whatever.

So, unless you [00:55:00] want to be a jerk, you're sort of stuck. And figuring out a trial probe could be real helpful. But the single most important thing, Jeffrey, is probably pause. Do nothing. Let time elapse. And I'm not advocating for do nothing forever, but three months, six months, three years, whatever it takes you but, pause And really let that exit experience process.

Jeffrey Feldberg: It's really words from the wise for the wise. And Ajay, as you're saying that, you draw me to actually the conclusion in the 12 questions. And I'm going to quote what you wrote. To discover the new calling, post exit entrepreneurs need to engage in deep self examination. They should consider a broad array of possibilities and focus on what they might want their eulogy to be.

If more money is what they want and what their ikigai is now, these might be daunting notions, but with abundant time and capital, it's a genuine gift to be able to architect a life in any desired manner. Although not easy, this is a worthwhile process to invest energy into to get right. And it's really, [00:56:00] AJ, words well said that you and co authors put into that, and it's some terrific advice.

So let me ask both of you this, before we go into wrap up mode, if there was one action item, and AJ, you maybe have just shared what that one action item is, the white space, take some time, pause, but if there's one action item coming out of this episode Before a listener goes into their next call or meeting or activity, if they could do one thing, perhaps low hanging fruit, low effort, high reward, what would that be?

Retired Founder aka Jeff: I think I'd, sum it up by saying, get on offense. When you have an exit, you have this vague idea of this life of leisure and vacation, which we've identified as false, and you may find yourself on defense. And what I mean by that is evaluating the opportunities that come to you. Here's a, maybe a company that's interested in having you on the board or someone that's interested in you investing, or someone wants a, check.

And you end up getting not pushed around, but you end up on defense. You're [00:57:00] in reactive mode thinking, well, do I want to do this? Maybe I want to be on this board. Maybe I want to participate in this nonprofit. When you're on offense, you've got to have your, Goal line. And this is part of what we talked about.

We're using sports analogies a lot beyond the finish line and the scoreboard and all that, but it's harder than it sounds. You might have a vague notion of it. Well, I'm going to do work for nonprofits. Okay. Well, that's great. Which one and how much are you going to allocate your time and your, treasure and your, talent to that?

And being very specific about what those goals are and moving toward them rather than just bouncing back and forth for the opportunities. And opportunities will find you, but being very intentional about what you're trying to accomplish with your precious life and the treasure in front of you is harder than you think, especially when you get specific about it.

Jeffrey Feldberg: Well said. AJ, how about yourself?

A.J. Wasserstein: Yeah, so I'll just double down and say that being a post [00:58:00] exit entrepreneur truly is a gift and a blessing, and for people to realize and embrace that opportunity time and wealth it's a rare combination that most people won't enjoy or experience, and to embrace that opportunity intentionally and purposefully, so specifically action.

Step as much as it might make Jeff gristle, I would encourage people, before they exit, while they're talking to their estate lawyer, while they're talking to their investment bankers, while they're still planning the exit to try to think about what post exit life is going to be. not plugging the work I've done To read, but if you want to read my stuff, read it.

It's on my bio page but talk to other post ex entrepreneurs who were three, five, 10 years ahead of you about their experiences and what they felt whether they were optimizing around more money or more emotion but really try to learn from the people who have traveled the path before you and avoid some of the mistakes that they've [00:59:00] made.

Jeffrey Feldberg: Well said. We can learn so much from people that have been there, done that, take decades of experience, and whether it be a conversation or it's a memoir, whatever the case may be, we can learn so much from that. So that said, it's a terrific segue for the wrap up. Now, AJ, you've already been through this.

Jeff, you're new to the Deep Wealth community and there's a tradition here on the Deep Wealth Podcast where every guest, we ask the same question. It's a fun question. Let me set this up for you. When you think of the movie, Back to the Future, you have a magical DeLorean car that will take you to any point in time.

So AJ and Jeff, the fun part is it's tomorrow morning. You look outside your window. Not only is the DeLorean car there, the door is open, it's curbside. It's waiting for you to hop on in, which you do. And you're now going to go to the younger self. So maybe it's AJ and Jeff, when you're a child, a teenager, whatever point in time that would be, what would you tell your younger self in terms of life lessons or life wisdom or, hey, do this, but don't do that?

A.J. Wasserstein: I probably would go [01:00:00] to my early twenties, mid twenties when you're sort of coming of age and beginning your own independent life. And I would tell myself that not to worry so much, it's all going to be fine, and enjoy every single moment, it goes by blindingly quick, and it's really about your most intimate relationships with your spouse, your kids, your family, and your friends, and Really to optimize around that and if you wind up with a little bit more money or a little bit less money you'll pale in comparison to having great relationships both physical health and health with the most important people in your life.

Jeffrey Feldberg: I love that. So AJ, I'm hearing you say, enjoy the journey. It's all about the health and the relationships along the way. Well said. Jeff, how about yourself? 

Retired Founder aka Jeff: much as I need to dial a specific date into the dashboard of that DeLorean, it's the message and that message carries back all the way. And the [01:01:00] message is it's going to be okay. You don't know how this is going to turn out. You don't know what the world's going to throw at you. It's going to be okay.

And if everything goes wrong, have confidence in yourself that you're going to be able to work it out and it's going to be okay. And if you happen to get lucky and exceed your wildest expectations. It's going to be okay also. It's not going to be perhaps as fabulous. It's going to be okay. Maybe a little better than okay, but I think that's the message because any founder who's been on this journey knows it's lonely.

It's hard. There are days where you don't think you're going to make it and there's days where you question everything that you're doing. And it's going to be okay.

Jeffrey Feldberg: Jeff, what I like about that, really at the best of times, at the worst of times, it's going to be okay and it's setting in a consistency. You could be the top of your game. Well, it could perhaps be even a little bit better, but hey, it's still going to be okay. It's all going to work out. Oh my goodness.

How am I going to make it through to tomorrow? Hey. [01:02:00] Take a breath. It's going to be okay. Some terrific advice. And as we wrap this up, and again, it's all in the show notes, for the listeners, if they want to reach out and get in touch, AJ, with yourself, where's the best place that someone can find you online?

A.J. Wasserstein: If you go to the Yale School of Management website, you can find my bio page there and feel free to email me if I could be helpful or supportive.

Jeffrey Feldberg: Terrific. And Jeff, aka Retired Founder on Social Media, if someone wants to reach out, see what you're up to, where's the best place?

Retired Founder aka Jeff: My Twitter X account is Retired Founder is probably the easiest. I have messages open and I'm new on that platform just a couple of months, but that's a good spot. And for those listeners that are not rolling their eyes, for the listeners that are shaking their head, like I'm one of these, I'm one of these people.

I am working on a community, a safe place to, to talk about post exit. Anxiety and the things we go through and that'll [01:03:00] be beyond the finish line or btfl. org, which will be stood up here hopefully in the next few days, probably by the time this drops.

Jeffrey Feldberg: Terrific. And again, for our listeners, it doesn't get any easier. It's a point and click. It's all in the show notes. Well, gentlemen, a heartfelt thank you for your insights and your wisdom today. And as we love to say here at Deep Wealth, may you both continue to thrive and prosper while you remain healthy and safe.

Thank you so much.

A.J. Wasserstein: Jeffrey, thank you for being so gracious and inviting me.

Retired Founder aka Jeff: Thank you, Jeff. Really enjoyed being here and AJ, thanks for sharing the air with a person far behind you on the path. 

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. What did you think? Was that a deep dive on the post exit life or what? 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.

Are you ready for it? The dramatic pause. I'll just wait a moment. Drumroll, [01:04:00] please. Subscribe. Please subscribe to the Deep Wealth Podcast on your favorite podcast channel. When you subscribe to the Deep Wealth Podcast, you're saving yourself time. Every episode automatically comes to you, and I want you to know that we meticulously craft Every one of our episodes to have impactful strategies, stories, expert insights that are designed to help you grow your profits, increase the value of your business, and yes, even optimize your post exit life and your life right now, whatever you want that to look like.

And every time you subscribe and a fellow entrepreneur subscribe, it's a testament to how together, Yes, we are. We are changing the social fabric of society. One business owner at a time, one liquidity event at a time. So don't let the momentum stop here. Subscribe now on your favorite podcast channel.

You'll never miss an episode. You'll be the first to hear from the top industry leaders, the innovators, the disruptors that are really changing and shaping the business world, and maybe you're commuting, maybe you're at the gym, maybe you're taking a well deserved break that we spoke all about on this episode.[01:05:00]

The Deep Wealth Podcast, it's your reliable source for the next big idea that could literally revolutionize your business. So once again, please hit that subscribe button, stay connected, inspired, and ahead of the curve. And again, your next big breakthrough moment, it might just be one episode away. Maybe it was even this episode.

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.