Successful Post-Exit Entrepreneur A.J. Wasserstein On How To Optimize Your Life For Happiness After Your Liquidity Event (#39)

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Steve Wells: [00:00:05] I'm Steve Wells.

Jeffrey Feldberg: [00:00:06] And I'm Jeffrey Feldberg. Welcome to the Sell My Business Podcast.

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Jeffrey Feldberg: [00:01:44] Welcome to episode 39 of the Sell My Business Podcast.

A.J. Wasserstein is the Eugene F. Williams Jr. Lecturer in the Practice of Management at the Yale School of Management.

Additionally, A.J. Is a private investor with a long-term orientation, interested in lower middle-market businesses and philanthropic organizations where he can be positively impactful by using his experiences, time, and capital. Mr. Wasserstein was the President of OneSource Water, the third-largest bottleless water service in the U.S.

OneSource water was sold to Water Logic, a U.K. based strategic acquirer in 2016. Previously A.J. was the founder and CEO of ArchivesOne, the third largest records management company in the U.S. ArchivesOne was sold to Iron Mountain after 17 years of operation. The U.S. Small Business Administration has recognized A.J. as the small business person of the year in Connecticut.

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

A.J. welcome to the podcast. We're really excited to have you with us today because you bring something that we've never talked about on this podcast before. We're going to talk about your exit and your success with that, and a huge congratulations, but you've done a deep dive into this paper that you wrote, this incredible case study: "What's Next: The Entrepreneur’s Epilogue and the Paradox of success." And you focused in on something that every single business owner goes through with life after the accident. But I know speaking for myself anyway, I never had that kind of heads up, which would have helped me tremendously, but one thing at a time, welcome to the show.

Why don't you start with an overview of what led you to your exit and how that went for you?

A.J. Wasserstein: [00:03:54] Sure. First Jeffrey, thank you so much for the invitation to visit with you and Steven. It's incredibly kind and gracious of you.  Appreciate the opportunity.

So, I started a business immediately after I got my MBA when I was approximately 24 years old. I ran that business for 17 years and we grew substantially during that holding period and absolutely loved it. I could not have been having more fun being an entrepreneur and a CEO and running a business, it was really exhilarating.

Somewhere along the way, I raised some institutional capital to continue our growth plans and we needed some external financing to increase the rate at which we were growing. We had some outside investors, so private equity firms and great folks. And we had them as shareholders for approximately nine years.

What's catalyzed our path towards an exit as we had an unsolicited, so an unprompted knock on the door from a potential acquirer that said, Hey, we, we might be interested in buying your business. And at that point, the private equity firm had been in for nine years, which in private equity years is a very long time.

And the private equity firms said, Hey, I got a great idea. Why don't we just hire an investment banker and test the market and see what happens? And I now joke that a private equity firm hiring the investment banker who tests the market is like going window shopping for a ring with your girlfriend.

And if you're window shopping for a ring with your girlfriend, you're engaged and you might as well be booking the church.  It's hard to put that genie back in the bottle. So, we hired an investment banker and they were absolutely fantastic. And we tested the market and went through a very structured process with multiple rounds of bids and auctions, blah, blah, blah.

The truth is once the numbers came back, it was really compelling for everybody involved. The private equity firm was looking for liquidity at that point.

It was a hard opportunity to pass up. So, that's what catalyzed the exit process and how we landed, where we landed.

Steve Wells: [00:06:29] A.J. here at Deep Wealth we talk a lot about an auction and how powerful that can be to increase the value for the exit.

And we also talk about the dangers of looking at someone knocking on your door and accepting that first offer. So, in your situation what happened? You had someone knock on your door. Did they end up staying in the process, going through the process?  How did that look and would you think they are offering the best deal had you not had an auction?

A.J. Wasserstein: [00:06:55] I don't think we thought that they were offering the best deal.   It just made us scratch our heads. When someone knocked on the door. They stayed in the process. I'm not sure they made it to the later innings, but they were in the process clearly.

Yeah, I think they just catalyzed us and made us realize, Hey, we're in a frothy market and maybe it would be worth testing the waters and seeing what the world looked like. And that's where we engaged professional support through an investment bank, which was fantastic. And they really ran them machine-like process,

Jeffrey Feldberg: [00:07:37] You're one of the few in the sense that most business owners, they get an unsolicited offer the prospective buyer knows that, Hey, I'm going to flash all this money in front of you. And most business owners, they see the dollar signs and they're thinking, why not?

I don't have to pay any commissions. I have someone right at the doorstep. I don't have to go through all the different steps. Let's just go with it. And it looks like some good dollars and Hey, I hit it grand slam to the rest of the world, even though they left untold millions of dollars on the table. And interestingly in your story is not just theory here.

It was the prospective buyer who did stay in the process, but ultimately wasn't the buyer who ended up purchasing your company through the liquidity event. So, many lessons that come out of that. For our community as you look back to your exit now, and you've had time to think about this and you've had reflections and you've been on doing other things, which we'll talk about, but as you look back to your liquidity event, what two or three things would you have done differently or even not at all, or maybe there aren't any, but if there are, what would those be?

A.J. Wasserstein: [00:08:46] What would I have done differently? So, I would start by saying I absolutely loved what I was doing, so it wasn't like I was burnt out. I was only 40 years old when I exited the business. So, it wasn't like I didn't have a lot of energy and enthusiasm. I felt like we were at the top of our game.

I was having a ton of fun. I could not wait for every day to start.  Look we took on the institutional capital and they were a wonderful partner. But I wish there was a structure or way we could run the business longer. I think we could have created a lot more wealth and I was having a ton of fun.

So, I'm not sure that it's really possible, but if there was a way to either delay the exit or prevent it for a bunch of years that would have been appealing to me.  What else would I have done differently? We hired a great investment bank. They were fantastic.

I feel like the support system and professional advisors we had were wonderful.  The company that wound up buying our business was the largest player in the industry. And we were the third largest player at that time in the industry, in the United States.

And I developed a business friendship with the executive team of the acquiring company over years and years. And at least once or twice a year, I would make a pilgrimage to Boston, Massachusetts, where this dominant industry player was located and I'd have lunch with the CEO or CFO.

And obviously, we were competitors, so it wasn't like we were buddies, but we talked about the industry, we talked about concerns. We talked about opportunities, we got to know each other and they wound up being the prevailing offer in our auction process.  We had to go through Hart-Scott-Rodino.

They had used some diligence. And I don't even remember how long the diligence window was, but 30 days, 60 days, somewhere like halfway through the diligence, I called the CFO of this company that wound up buying us and said, John, we're halfway through the diligence window aren't you going to actually do some diligence?

And what exactly are you going to do? Because I got a red circle around the date, on my calendar when I think we're closing. What exactly do you have to do? And he replied by saying, A.J., we've been diligence in you for about 15 years. We're ready to close whenever you want. So, I share that because even when you go through a successful auction process and you think you have the most attractive number you could possibly have, there are still a lot of miles between that verbal signaling and the wire hitting and diligence can derail a whole bunch of deals and planting the seeds with the most likely potential buyers, years and years in advance might serve an entrepreneur when they're actually going through the exit process and diligence. So, that was just like really de-stressing to me when I heard, Oh, we're ready to wire, whenever you're ready.

That was a great feeling.

Jeffrey Feldberg: [00:012:01] A.J. It's interesting. Two valiant points come out of what you just shared. And firstly, I know a lot of business owners are, let me just get some money into the company. I can grow quicker and I'll do all kinds of wonderful things. And don't necessarily look down the road of what that meant not to put words in your mouth.

What I'm hearing you say is left up to you. Perhaps you wouldn't have had that liquidity event at that point in time. And perhaps you would have kept on running the company, but because it wasn't just you and you're an astute businessman and you had partners and everyone has to get along and we have to make sure that we're living up to our responsibilities.

That really wasn't an option at that time. And words to the wise, to the community out there. There’re always two sides to a coin for every situation. And it's sometimes you don't have a choice and you need to move forward in a different direction. And that's just the way it is, but at least go in eyes wide, open.

And the second thing that stood out and in the nine-step roadmap, in the Deep Wealth Experience module, number two, we talk about know your buyer better than you know yourself. And we always like to say, never assume that it's going to be your competition who's going to buy you. Now, in your case, it was, and I'd like to share it with the community.

That's not always the case. And oftentimes it's not usually the case, but the one smart thing that you did and it really worked to your advantage, and I love your story is you made a point to reach out to people in the industry your competitors, and just talk with them and have them get to know you because you nailed it on a key point, not just in mergers and acquisitions, but both in business and in life.

Money's not the currency, it's trust. And over the years you built up trust with your future acquirer that just paid itself off in spades later on. So, that's terrific.

A.J. Wasserstein: [00:13:51] So, Jeffrey, just to amplify a little bit, I learned a ton from this large competitor, they were incredibly gracious and kind to me and generous with knowledge and teaching.

And they were a public company. So, there was lots of public information and I'm not naive to think they told me anything that was proprietary, but they wanted good participants in the industry and they were kind to help me understand how they were thinking and different dynamics in the industry.

I would like to think we paid that forward in the industry also where we helped other people in the industry. And look a dynamic, healthy industry where lots of participants thrive is better for everybody.  That was really neat. And I just want to be clear, I don't regret raising institutional capital. The private equity firm who was a shareholder in my business.

So, they were a fantastic partner and I have to be completely honest and objective. I would not have wound up where I did without their participation and support and guidance and relationship.  I wish we could play it for another 5 or 10 years. yeah, I do.  But that's not the way the game works.

So, I just want to be clear it's there, there was no regret. It was just can the game go on just a little bit more, it's all good.

Steve Wells: [00:15:13] I'm curious, you may not have much to say about this, but selecting the team is critical for most transactions.

And it sounds like you had a great experience and a great team. How did that come about? How did you find your investment banker and the other team players?

A.J. Wasserstein: [00:12:26] So, great example. The investment bank we worked with was RW Baird.

They're based both in Milwaukee and Chicago in the Midwest. And they were an absolutely great partner for us. So, I'll give a shout out to Chris Hildreth and Peter Kies.  They were our lead bankers with Les Cheek. They were the perfect size for us. So, they weren't a mammoth where we didn't matter and they weren't boutique and too small where we were way over their heads.

It was just a great relationship. They had inroads into tons of financial buyers who did not wind up being our market, but they were great people to talk to. And they also had inroads into tons of strategic buyers and they just ran a masterful process to make our business the best positioned and most desirable it could be.  Yeah, they just say a great job.

Now, that being said, I think a tip I would give to potential entrepreneurs is to figure out how you could be the best client ever for your investment bank. You want to be the easiest client. You want to be the first phone call that they return and you want them to be excited about your deal and project.

I'm still friendly with all those guys. They've been helpful in other parts of my life. And I would recommend working with them unequivocally for any entrepreneur that was thinking about an exit.  I got introduced to RW Baird through our private equity firm. So, we ran a beauty contest where we interviewed half a dozen investment banks and Baird was definitely the right fit on a lot of different levels.

One more tip I would make about investment banks and relationships and negotiations with investment banks. Be generous with fees. So, you want your investment banker working as hard as you can and fighting for that next marginal dollar, and being parsimonious with banking fees is short-sighted and foolish for the entrepreneur.

You want them to be thrilled with their opportunity and constantly feel like they're working for one more tick and not take a low-risk high probability outcome because there's not value for going for the bigger outcome. So, what lawyer, we worked with a guy by the name of Alex Temel and based in Boston.

He's fantastic. Sometimes lawyers can be deal inhibitors. So, they're great at figuring out why a deal shouldn't get done or all the problems in the deal. And of course, you need your lawyer and council to think like that, but you also want a legal partner who works on overcoming the obstacles and getting the deal to the finish line.

So, not a person that sees landmines and throws up his hands or her hands, but she's landmines and figures out how to go around them or go over them. And as a collaborator, not an inhibitor,  

Jeffrey Feldberg: [00:18:30] A.J. lots of nuggets in there. Let me circle back on one of the comments that you make and you're really preaching to the choir.

It's a page out of the Deep Wealth book as well. But from your perspective, what can someone do to become the best client ever for an investment bank? Or what did you do to have that happen?

A.J. Wasserstein: [00:18:51] Selling a business is an extraordinarily invasive process. It's really time-consuming, but when the investment bank asks you for data.

And then they're going to ask you for data spliced a different way, give it to them. You got to be on top of every request that they make and all the requests aren't going to be logical or in the time sequence that you want. But unfortunately, it's this crunch period in your life. And hopefully will give you financial independence and security and you have to do backflips when they ask for information.

You have to be accurate. You have to be precise. You have to be available. So, when they want to talk or they want to get you in front of someone, the answer is yes. When you're in front of someone, you got to be on, you have to be, 10X enthusiasm and really tell the story in the most dynamic way possible.

Our investment bank was kind, they coached us on presentation skills and telling the story and, giving enough information, but not drowning the listener in information but being the best client, you could be in taking their input and advice. They do it every day. So, they're the experts, not me.

They're the experts. And really listening to their guidance on how best to deliver the story.  The other thing Jeffrey is we really took ownership of the I'll call it the book the private placement memorandum, the confidential information memorandum, the offering memorandum, wherever you want to call it, I call it the book.

The bank wrote it. And we, I like to think we gave them lots of rich data. But when we got a draft of the book, we did not accept it. We ruthlessly edited the book as if it was our autobiography. Me, my COO, my CFO. And I asked the private equity firm to do it as well.

I'm not sure they learned it fully, this is your big one at-bat. And as much as I loved our partners at Baird, I wasn't fully delegating that book process to them. We really leaned in to make sure it was accurate and as compelling as possible. So, I think those are some of the tips to be the best client possible.

Don't push back when they're minor negotiating items, make sure you're focused on the big items, but not the little items.

Steve Wells: [00:21:22] Before we move on because I want to talk about after the exit and you've written some interesting material on that.

Is there anything else about the actual exit process incorporating your team or your clients or anything that you'd want to share that'd be a great help to people thinking about going through this?

A.J. Wasserstein: [00:21:40] Yeah. We had a really small, tight circle of executives in the company that knew about it.

So, this is jarring, so it's not something we wanted to share openly with all of our team members, because a deal could go sideways. It's really important if those key executives have not previously been incentivized towards a good outcome, either with stock grants or stock options, there, there's got to be a financial carrot for those key executives to make sure they're fully on board with what's going on and they're all in.

The only other thing which Stephen is to enjoy the moment. It's like your victory lap and your bow after the performance. It's such a special moment to tell your accomplishments and stories to a whole bunch of really smart, successful, sophisticated people.

And it's very validating.  There are a lot of mixed emotions, but we'll get to that. But there's also this sense of enjoying the special moment in the sun.

Jeffrey Feldberg: [00:22:41] In our 9-step roadmap at Deep Wealth in through the Deep Wealth, Experience one of the things that you're really highlighting the importance of, and it sounds like this was woven in from start to finish for you. We call it the winning mindset. That's step number four of the 9-step roadmap. And so, from enjoying the moment, becoming the best ever client of an investment banker, doing cartwheels and flips when you're asked for things, just to make sure that you're ready and you're there from a timing perspective, always being on, it sounds like you just zoned right in, Hey, we got to have the right mindset. It's going to help us. It's going to help everyone involved. It's going to get us across the finish line. And so congratulations on that. And it's something that we can't stress enough to the community that. It costs no more, both time and money for the right mindset, the positive mindset than the wrong mindset or a negative one.

So, now let's start to dial in on what you've been working on now, and you had the exit and you have some really interesting observations. And I know for myself, when you shared them with me offline, it resonated. And like I said, most business owners feel this. No one really talks a lot about that. So, you hide your exit, and what happened next?

A.J. Wasserstein: [00:24:03] So, it's really fascinating. The first thing that happens and this is totally autobiographical. I'm not saying I'm a proxy for everybody. This is just my story. Although it’s been confirmed by many entrepreneurs I connect with. The first thing that happens is there's a sense of relief.

So, you're running a hundred miles an hour for decades, and then you're running 200 miles an hour for that last mile sprint to get across the finish line. So, there's this sense of just breathing and release and a relief. One of my friends described it as he took the yoke off your back. The wire hits there's this just complete decompression coupled with this elation like this is your Super Bowl, World Series, New Year's Eve all wrapped into one.

So, there's this real high, that's validation. And then there's this weird malaise and darkness that sets in realizing that your baby's gone, this thing you loved and nurtured and cared for is gone. Your social interaction with professional colleagues very quickly attenuates.

It's just this really weird moment of going a hundred miles an hour to going to zero and it can be filled with bizarrely loneliness and isolation after the exit. And Jeffery and Stephen, my story was, we sold the business.  I stuck around for 60 days, 90 days, and that was it.

So, it wasn't like I was still working at the company that acquired us. It was a full separation after. So, the 90-day bridge took my photos out of the office and that was it. I went home. And that was a really weird moment because life goes on for. Everybody else. And your family, your kids your spouse. All the people in the company stuck around.

So, they all, changed uniforms, was working for a new owner, a new company trying to fit in and work their way. And my life was very different. Just complete sadness and malaise, loss and mourning. And the truth is I was incredibly confused.

I didn't know how to process what I was feeling. I felt very alone. My wife worked. So, she got up every day, went to work. The kids went to school every day and I was alone in the house and trying to figure out things. And that was hard. And I think what's so tricky about it is we get sold the story narrative both in business schools and in popular media that, being an entrepreneur, it's great which it is and build a business. And if you exit the business successfully what you live life happily ever after. And I was so waiting for my happily ever after, and it wasn't coming. And I just didn't know.

I thought there was something wrong with me. I didn't know what to think.  And everyone else is so happy for you.  I didn't feel like I could talk to anybody about what was going on in my head.

Steve Wells: [00:27:21] A.J., Jeffrey, and I can say we have experienced many if not all the same feelings are going through our exit.

And I'm looking at that. So, now that you've gone through what could you have done, or what could you have done anything to help you, in that transition that would've made it better or easier now that you know what is like on the other side?

A.J. Wasserstein: [00:27:41] I'm not sure I'm an expert despite having written about this and. I don't think Jeffrey, we got out there yet. My role now in life is I’m a faculty member at the Yale School of Management. And I teach courses in entrepreneurship, which is a wonderful encore career.  What do I wish I knew Stephen?

I wish I knew this for one. I wish someone told me while I was running a business that selling a business is an emotional rollercoaster. Just eyes wide open. I'm not saying it would have made it better, but it just cognizance. So, I have three kids and my youngest is a freshman in high school.

So, we're on the cusp of an empty nest.  I know an empty nest is going to be hard. It doesn't mean it won't be hard because of my awareness, but emotionally prepared, I was not prepared to deal with the emotions of selling a business. At the most simplistic level, Stephen, I wish I knew that It's not all good that there's this underbelly to success. There is this epilogue and paradox of what's going on after you sell the business.

Steve Wells: [00:28:49] Yeah. That makes sense. And I'm not going to put words in your mouth. For me, my identity was so wrapped up in the business and I think that's it's good, but some of it was unhealthy if that's really not who I am, and then after you've got this huge exit and all this money, then you're an expert in some people's eyes and you're a fool before, but you're the same person, so I find that interesting.

A.J. Wasserstein: [00:29:10] I think the three things that get disrupted in your life are structure, meaning, and identity.

So, when you have structure, you wake up in the morning and you work out, you drop your kids off at school. You go to the office; you say hello to everybody. You settle into your day and routine, or once a week, you have the executive team lunch. And once a quarter, it's the leadership team gathering and the quarterly board meetings and the industry conference and the investor dialogue. There's this rhythm and pattern to your day, week, month, and year when you're an entrepreneur and a CEO. And it's very comfortable. It's very gratifying to know that every Friday we have our executive team lunch and every Monday I meet with my COO for 30 minutes to kick off the week.

There's a structure that gives you rhythm.  You also have meaning, so you wake up every day and you're building, you're trying to serve customers. You care about team members. You interact with vendors and the banker.  You're building this living, breathing organism, and you have a purpose, you want to grow X percent this year.

You want to be the best in the market. You want to attract the best new hire, there's all this purpose and meaning to your life and the day. And you also have this identity you're an entrepreneur, you're a CEO. You work at ABC company. You're in the XYZ industry. There are all these things that give you this very satisfying, comfortable existence.

And Stephen, the question I dreaded most after selling my business is what do you do?  And that's such a common question in our society. It's not impolite. If you're at a barbecue or a cocktail party for someone to say, what do you do? And I could not answer it well, at all. You're retired.

Then they think you're unemployed or not employable. I just sold my business. Oh, you're a jerk. You’re bragging. I'm an investor. Are you a gambler? No answer felt right. And you lose all that identity. And I remember once when my kids said to me, Dad, what do you do?

You just hang around the kitchen all day and, it's very humbling  

Jeffrey Feldberg: [00:31:35] As business owners we're at the pinnacle of success that the vast majority of the population dreams about. We're there. We're living it. There's no pity party of, Oh, look at this. Look at this business owner, who just sold for untold how many millions? Oh. That poor business owner looks at what they're not doing and how they feel bad. I think as men we tend to hold things in a little bit more in sharing our feelings. And this is crossing onto the softer side of things that it may not be natural territory for men, in particular, to express these feelings and your friends are having a life. They're working, they're having their career. And no one wants to come and play with you in the playground because they're busy.

A.J. Wasserstein: [00:32:19] Yeah, there's no one to play with, where I live it's asynchronous and atypical for a 40-year-old person not to work. And no one knows how to process that.  Or I didn't know how to process it so that's very atypical.

Part of the compounding conundrum for a post-exit entrepreneur which we call PExEs (post-exit entrepreneur) in this case note is when it happens at a disproportionately young age, it's so much harder. So, if you sell your business and you're 65 or 75, there are probably other peers in your cohort who are going through similar life changes or retirements. But if you're 35 or 40 or 50, even that's very asynchronous and atypical.

Jeffrey Feldberg: [00:33:07] Now A.J., in your case note and I know you call it a note and everyone should absolutely read this. We'll have a link to it in the show notes. It's a little bit more than a note but it's well worth reading.

Now you have the What's Next Framework, which I thought was very thoughtful and insightful, and yeah. You start from six months to 24 months after the exit. There are four areas in the What's Next Framework. Can you talk to us a little bit about that of the process that we should be thinking through even before we exit, we know maybe there's a liquidity event a year from now five years from now, 10 years, whatever the case may be.

What's the What's Next Framework, the four different stages that we should be considering.

A.J. Wasserstein: [00:33:51] Sure. So, academics like to come up with pithy acronyms and the What's Next Framework is PROT. I'm not sure rolls off your tongue, but it's got a couple of consonants and one vowel, so it could be a word.  And it's a shorthand for pause, reflect, operationalize and think, and those are the three stages. I think that PExEs post-exit entrepreneurs need to work through to get to their new place.

And it's an iterative process, so I'll just highlight them at a high level. So, pause and this is something I fail to do, Stephen. So, when I was in my malaise and wandering darkness.

I thought the answer was do something. I'm a doer. I like doing things. So, I immediately tried to figure out what my what's next was. And I think the very best thing to do after an exit is nothing. And this is extraordinarily difficult for Type-A entrepreneurs that are doers and builders, stillness is hard.

But the very, very best thing to do is go through a process of mourning, go through a process of emotional decompression. Just be still and resist the temptation to make investments, buy cars, buy houses, start businesses, just do nothing. Walk, hike, chill, pick your kids up at school, drop them off at school, just be.

And really let go. And everyone's different, but depending on the size of your exit, I could easily paint a picture that you need to do that for 6, 12, 18, or 24 months. Just let go. And I think during that window, you want to seek solitude. You very much want to be alone and just let your mind wander.

Just decompress. I spoke to one post-exit entrepreneur. So, after he exited, he told me he went on a pilgrimage in Europe. He just walked alone and really let your emotions process and let the mourning and letting go settle in, but seeking solitude. I think it's also really worthwhile to connect with mentors and coaches, preferably life mentors and coaches, although a paid coach is not bad or a therapist is not bad. Those would be excellent but really connect with people who have seen you over long periods of time. Friends, parents, faculty members, neighbors, but people who can just listen. People who might be able to offer perspective. People who can let you emote I think the single most important thing in the Pause is to define if you previously haven't or reaffirm your values.

So, you're about to engage on this next chapter and journey. And unless you have a compass and roadmap, you don't know where you're going. So, Stephen, if you only define yourself as an entrepreneur, if that's your only measure, your only identity. And you're not a friend, a parent, a spouse, a community member, the range of possibilities becomes really narrow. So, what matters most to you and why is going to be really helpful as you move forward. And that's the screen and compass that I think is ultimately going to ground you and help you figure out what's next.  

Reflect, I think after you let go, you get across the first bridge. You need to begin to contemplate what's next and what the choices are.

The one piece of advice I would give in this chapter is to open up the aperture. Don't revert too quickly. So, the most common thing post-exit entrepreneurs do is do it again. They were good at it. It was comfortable. It had structure, meaning identity like it was all easy and they say let me go do that again.

So, pause. Think about all the things you could do. All the things you could do that are comfortable and uncomfortable. So, maybe it’s volunteer work. Maybe it's being a recreationalist. So, doing things that are. More pleasure-seeking but all the different things you could do a mentor of mine after he sold his business, went to divinity school.

Not to become a practicing religious leader, but really is a way to reorient.   But this is the moment to engage. And one of the exercises we propose is a hundred-year exercise. So, what do you want your story to be when you're a hundred years old? So, if you've been given this incredible gift, have no financial limitations, sometimes freedom, depending on where your kids are and your spouses, but you still have this blank piece of paper and you get to write your story.

So, what do you want your story to be when you're a hundred years old? And that's really intimidating. But going through that process and defining what you want your eulogy to be, what you want, your end story gives you purpose and intentionality and increases the probability that you'll be doing, the things you want to do as compared to slipping into a reverting to something unintentionally.

So, the other exercise in this reflection mode is what I called the What's Next Matrix.  I'm going to be a little geeky here. I apologize. But on the Y-axis write down all the things that you either want to do or don't want to do. I want to travel for personal reasons by I don't want to travel for work.

I liked being a leader, but I don't want employees I don't want P&L responsibility, but I want purpose and meaning. I want a rhythm to my day, but I want freedom with my time. So, however, wacky and contradictory the things you seek in your life, write down on the Y-axis. And I'll give all the listeners a hint.

Y is the axis that goes up and down. And on the X-axis, the horizontal axis, write down all the potential next chapter journeys and paths you could take so easily. Be an entrepreneur again, be a hired CEO, be an investor, be a professional volunteer.

Be a professional board person. On my list was to be a ski instructor. Be a teacher, be a professional speaker. Your recreational lists, but no dumb ideas at all. And then score the Y versus the X and try to bring some objectivity and quantitative analysis to which pathway might be the most fulfilling.

I love skiing, but it turned out when I did this, I don't think I'd be happy being a ski instructor. I think it would be really fun for a month. But I think being a ski instructor, wouldn't be intellectually engaging and challenging. It wouldn't give me a sense of purpose and leadership in some ways. Try to do that objectively.

So, let me touch on operationalize. This is the moment when I think you began to do trial probes and whatever pathway you choose going forward. I strongly recommend that you do it in a way that you could escape easily. So, if you want to go on a board, say, Hey, I'm so flattered. You'd like me to be on your board.

Why don't we do a six-month trial run? And I'll see how I feel after six months. And you can see how you feel after the six months, rather than locking in forever. Same thing with being a CEO or starting a business. Seek an escape valve if possible. I think in the operationalize, you really need to begin to think about wealth management.

I do not think What's Next is about wealth management, but you do have any responsibility to steward the wealth that you got. And I will say that being a wealth manager is extraordinarily different than being a wealth creator and that's a whole many people tripping. And then finally, I think in the operationalize for me, I want it to really wrestle with, do I want my life to be more about gathering or do I want my life to be more about serving?

In all honesty, being an entrepreneur in many ways was about me. It was about my ego accumulating wealth, then, being the center of a lot of things, which was wonderful, fun. But I really contemplated the next chapter, potentially being more about others I'm serving.

And then finally the think chapter, Jeffrey and Stephen, it's just really checking in.

So, you established your values, you have this freedom and flexibility periodically checking in and making sure you're happy. You're fulfilled. You're where you want to be. And if you have this incredible gift and luxury of crafting your own story in life, making sure that you don't settle. And in that thinking phase, if you're dissatisfied, figuring out how to pivot, and if you're satisfied, figuring out how you hold on.

Steve Wells: [00:43:00] You've hit it on the head, the nail again, that metaphor. And we have been through that and it's interesting to me you put a little bit of a timeline and I look at my life. Some of these things have taken years and your timeline was much shorter and that should have been, I went down some bad, not bad in a bad sense, but, slowly when I discover some of these.

But tell me a little bit about the timing of this.

A.J. Wasserstein: [00:43:24] Much longer than people think. In the case note, I trimmed back some of the timelines because when you talk about years and years it's too overwhelming to a reader or post-exit entrepreneur. But I think the letting go process can take years.

I think the reflection process can take years also. Operationalizing I think is a series of fits and starts. I think it's rare that people gracefully move from one chapter to the next and the thinking component is perpetual but you could easily paint a picture that this is five years or longer,

Jeffrey Feldberg: [00:44:02] For our listeners, I really encourage you to look at the case note, but in the case note, there's something called Figure 4, which is pre-exit and post-exit time allocations. You're out there and you're cranking and it's a pie chart and 80% of the time is professional.

And I think we could probably say maybe it could even be higher for some business owners. This thing here.  Just the other day we had a guest on the podcast and he said something interesting. And he said I focused so much of my early years on the business that I really put my family relations to the side.

And now that I'm getting up there in years, I've circled back. And he said this is really the one regret that I have for my entire career. And so it's interesting. And why I bring that up is if you look at the pre-exit and the post-exit, some areas which have 0%, or they might as well be 0%, things like spiritual or health or white space don't exist in the pre-exit or are minimal.

When you get to the post-exit, they could be anywhere from 10 to 20% of your time. And so if you haven't developed that ahead of time and now wham, you've had your exit, you're out of the company. You're no longer there day-to-day, that's a tough thing to do. And I speak from personal experience because I've walked that path and it's not a comfortable one.

So, talk to us about your own experience and what you're seeing out there speaking to business owners.

A.J. Wasserstein: [00:45:32] Sure. These are illustrative pie charts in the keystone, but the pre-exit one was probably pretty indicative for me, the vast majority of my time and mindshare was going to the business.

I'd like to think I wasn't a bad dad or a bad spouse, but I was a full-on entrepreneur. And if I was at one of my kid's soccer games, there's a high probability. I was on the phone. And that's not something I'm proud of that's bad but I think when you're in post-exit that you have this luxury of creating your pie chart.

And where do you want to allocate time to, and look I was talking to someone a day or two ago, and the person asked me what I do with my time now. And he was so prodding because it, in his years, it didn't feel like I was full time and I'm not, I want at least 30% of my time to be what I call white space.

I want to be flexible. I want to have the mind share and time when my kids ask me to go for a hike or play a game or do anything, the answer is yes. I don't want to be overcommitted. I won't be under committed. I want to have time for my health. I want to have time for my awesome wife of 27 years.

Yeah, I think you just need to prioritize and make sure that the post-exit time pie chart doesn't get sucked back into one professional commitment. It's not where I want to be, but everyone gets, make your own choices, Jeffrey. I'm not saying what's right or wrong.

Steve Wells: [00:47:03] Again, great advice. And I really would encourage people to read the paper and think about it. And I think it’s really good advice. I don't know if the entrepreneurs listen because they're so busy and they're working so hard, but they need to listen. But when you're going through the exit, this process takes a long time but the more you are prepared knowing this is going to be a transition like you said, and the more that you are identifying what your core values are and what is important and not try to do it in the middle of the battle, because it's going to be more confusing.

And go through that effort, I think is really valuable advice.

Jeffrey Feldberg: [00:47:40] Circling back to what Steve was saying, just now. You've done a brilliant job in one of the diagrams. You call it archetypes. And you have five different archetypes. And again, please take a look at A.J.'s case note. I can't stress that enough for the benefit for those that are listening. A.J. has put this into you, have the, I. The discoverer, the recreationalist, the investor, and the philanthropist.

And it's not that there's a right or wrong with any of those. It's helpful though, to know deliberately and intent fully, Hey, this really resonates with me. I'm going to go in this direction. And A.J. it would be terrific to have your insights on the archetypes and what you can share about that with our community.

A.J. Wasserstein: [00:48:26] I don't think these are the only archetypes Jeffrey, but these are very popular ones where there's a Do-It-Againer, I want to be a CEO again. I want to be an entrepreneur again. The discover. Someone who's seeking and figuring out what to do, and can't quite find it. The Recreationalist. That's the person that plays golf every day.

You take a once in a lifetime trip every month. The investor. I have a pile of money and my purpose in life now is going to make, be making that pile of money bigger. I'm going to spend most of my waking hours thinking about more wealth accumulation. And the philanthropist. And that's the I'm on the not-for-profit board, or I am giving away money.

None of these are right or wrong. And the truth is most PExEs post-exit entrepreneurs probably have components of each in them, but try and figure out if any of those archetypes resonate with you and which you gravitate towards and which potentially fit for you or in what proportions.

Steve Wells: [00:49:31] And I know for myself.  It's hard to be honest with yourself so many times I think I know the answers to those things and the farther I get down, I realize my motivations weren't as pure as I thought.  That kind of selfish self-centeredness and wanting to accomplish or having the accolades of being in that position.

So, I think that exercises are really important to try to identify, how do you envision yourself going forward? And there are some practical realizations. I know I set up a foundation before we exited. Some people think about charitable giving, so it gets into the transition of Wealth too.

And if you have some ideas about That there are benefits to identifying that before the actual event for lots of reasons. Taxes and otherwise,

A.J. Wasserstein: [00:50:14] Since you mentioned the word wealth. Something I figured out in my post-exit, was, it's not about wealth at all.

So, many people think post-exit, it is about managing your wealth and very quickly you can connect with a lawyer and they'll want to talk to you about this alphabet soup of various trusts and ways to structure and preserve and give and transfer wealth, it didn't resonate with me. So, I don't think it's about wealth, and depending on the size of your exit, if you already have a big pile of wealth and you're not happy, having more will not make you happier.

So, I think that this whole post-exit journey is figuring out what's your epilogue. So, there's this false narrative that your happily ever after you discover you're not. So, you need to have the epilogue. The movie and story in Entrepreneur Land always end with the exit, but there's an epilogue. Life goes on and finding your epilogue and figuring out how you create new structure, meaning, and identity is what it's all about.

And this is just my opinion. It's rarely focused on wealth. It's really focused on what you do with your time and what gives you joy and fulfillment and satisfaction.

Jeffrey Feldberg: [00:51:32] A.J., we could have an endless conversation here as there are so many avenues to go down and it's been an absolute pleasure speaking with you. As we begin to wrap things up, and I know Steve is waiting in the wings with our question that we'd like to ask everyone who comes on as a guest of the podcast.

But the one question before that, so many people go through what you went through, but you took it one step further. You sprang into action and you've put this beautiful case note together. I'm wondering, was there a pivotal moment or a seminal moment for you that you said, you know what?

I need to take this to the world and share it with my fellow “exiters” if there's such a word, who have gone through these liquidity events. what was that for you that had you do this terrific piece of work?

A.J. Wasserstein: [00:52:19] Look, I'm a geeky academic now. And one of the things I love about my role at Yale is I get to think and talk about all these fascinating business topics related to entrepreneurship.

And I can't even tell you how much I love my post-exit life now being a teacher is truly a gift. What I think is fascinating about this topic Jeffrey is that every student I have wants to be an entrepreneur and they're all chasing this rabbit and they don't know what it's going to feel like when they catch the rabbit.

So, I think it's really worthwhile in Entrepreneur Land to at least introduce to people what it feels like when you get everything you've ever dreamt about. And just being prepared and realizing it might not be everything that you hoped.

Steve Wells: [00:53:10] A.J. we always ask one question, but you know what?

It's going to be an easy question for you for a lot of reasons. One is, I think you've already answered a lot of it. And the other one is you deal with young students younger than us anyway. Which is about everybody. I am, I should say for me, So, here's the question. So, I got back to the future type question.

If you could go talk to the 18-year-old or the young A.J. and you've been through your life and you've done your exit, you've done all your things. You've had your family. What advice would you give your young self if you could go back there and tell him something?

A.J. Wasserstein: [00:53:46] I've written a lot about this topic.

I've written. Another case note, which is advice to graduating MBA students. I wrote a book for my kids. What's Next: The Young Adults Roadmap to Life, and that's not a plug at all. I've thought a lot about this and both those things I just referenced or what advice I would give myself

This sounds so silly, but the game is really about optimizing around happiness. And happiness to me is not a short-term sugar high. So, eating a hot fudge sundae is not happiness. Having deep, meaningful, personal relationships, learning a language, learning how to play an instrument is happiness.

And life to me is all about optimizing around happiness. And when you're a hard-charging CEO and entrepreneur, I think you can lose sight of that really quickly. You think the most important thing in the world is building a company or being the best company, the biggest company or the, the company worked the most.

And it's really all about figuring out how you find happiness in your journey in life.  The truth is I need to always optimize around that. I sometimes optimized around the wrong things. And wish I optimized around the right things.

And linking it to the conversation, Stephen, and I think if you're optimizing around the right things when you experience this massive dislocation of an exit, you might be better prepared because there are other components of your life that are vibrant and thriving. And if all your chips are on being an entrepreneur and all of a sudden, you're not an entrepreneur, that's hard.

But if more of your chips are on being an awesome spouse an awesome friend, a wonderful dad, and having other interests not just being an entrepreneur. I think when you exit it's a smoother and potentially easier transition.

Steve Wells: [00:55:37] Excellent. Excellent.  AJ people would like to find you, where would they do that?

And we'll publish information in the show notes as well.  

A.J. Wasserstein: [00:55:46] If you Google "A.J. Wasserstein Yale," you'll get to my bio page at the Yale school of management and that's got my email address and everything I've ever written for Yale.

Which, if I can make a self-deprecating joke, I always recommend people read what I write just before they go to sleep. So, they'll be guaranteed to get a good night's sleep or learn something, but you're a winner either way.

Steve Wells: [00:56:12] Listen, we really enjoyed speaking with you. Thank you for your wisdom. And I know you're going to be a real gift to our listeners. So, thanks again.

A.J. Wasserstein: [00:56:21] Thanks for having me, Jeffrey.

Jeffrey Feldberg: [00:56:22] It's been a lot of fun. Thank you.

A.J. Wasserstein: [00:56:23] Totally my pleasure.