Episode 740 | My New Book! The Entrepreneur’s Guide to Selling Your Business Without Regret

Rob Walling:
Welcome to Startup For, the Rest Of Us. I’m your host, Rob Walling, and in this episode I sit down with Dr. Sherry Walling to talk about our new book Exit Strategy, the Entrepreneur’s Guide to Selling Your Business Without Regret. The Kickstarter for this book launches today. If you want to back it or you’re interested in checking out the tears and seeing all the amazing copy that Leanna Pat wrote for us, head to exit strategy book.com. I hope you’ll consider backing this book. I talk about it in the conversation, but I’m really proud of the end product of what we put together, and we put a ton of time into it. We interviewed a lot of entrepreneurs across different business types. It’s not just about selling SaaS, it’s about selling for the most part, any kind of business. And I’m really excited to get this into the hands of folks like yourself, entrepreneurs who may be thinking about selling, who may be in the midst of selling or who have sold and are trying to think about what’s next. Or even if you are not thinking about selling today, having this knowledge in your head as you build your business can only help you. So exit strategy book.com, it’d be amazing if you decide to back the Kickstarter. And with that, let’s dive into our conversation, doctor, Dr. Sherry Walling. Thanks so much for joining me on the show.  

Dr. Sherry Walling:
My pleasure.  

Rob Walling:
So we wrote a book, another book, this one’s called Exit Strategy, and I think a couple clarifications right off the top. It’s not just about selling SaaS, it’s about selling any type of company. We interviewed folks who sold agencies.  

Dr. Sherry Walling:
Yeah, professional service companies, a sort of chain of gyms, brick and mortar businesses. This book was really born out of my conversations with clients over the years who said things like, this is the hardest thing that’s ever happened to me, or I feel like I’m going through a divorce. And that’s not limited to SaaS. The challenge of this process is pretty universal for entrepreneurs going through it.  

Rob Walling:
And since the book focuses so much on the mental, the emotional, the psychological, the without regret part of before selling, thinking through should I sell, what’s it going to look like during selling? Oh my gosh, this is a pressure cooker, as you said, it’s the hardest thing I’ve ever done. And then the after recovering working for the acquirer, what to do next. Those things apply broadly across pretty much any type of business that is not just a, if you have look, have a little 10 K side project or some tiny little thing. Is it this agonizing? No, but this is about having a bigger exit and maybe having a team and that kind of stuff. And that applies to a lot of different types of businesses.  

Dr. Sherry Walling:
It’s about the story of building a business that becomes very valuable and sellable. People offload apps here and there or do things on a pretty small level, but this is the story about when you build something that is part of you and you put all of the blood, sweat, and tears into making something that’s very valuable, and then what it feels like to go through the process of selling it, of releasing it, putting your life together afterward.  

Rob Walling:
And there were a lot of really good books about selling your company. John Warlow has one art of selling your company to Andrews wrote before the exit Bo Burham wrote Finish Big. So I guess what’s our unique take? It’s two part question. Why did we decide to write this in the first place? And then what is our unique take that you think we bring to the topic?  

Dr. Sherry Walling:
I mean, I think the pairing of you as a serial entrepreneur and me as a clinical psychologist is really unique. I think there’s a lot of nuance and mental sort of analysis in this book that is different, or at least we are adding something pretty significant to the conversation when we think about the kinds of processes that people are going through when they’re going through a major transition in the middle of their professional lives. You’ve also been on the front row of hundreds of exits at this point in your work in TinySeed and through your connections with MicroConf. And so I think the number of reps that you and I have done together from very different perspectives is unique and really shapes what we’re offering in this book.  

Rob Walling:
And and I, it felt like we were having similar conversations over and over where you were like, Hey, one of my clients is thinking about selling or going through the sale process or has gone through the sales process and this is happening. And I’m like, well, didn’t that happen to someone else? Or that did happen to a friend of mine that I know through MicroConf. And it was like we would get asked questions of like, well, what books should I read or what resources are there around this topic? And it kept being like, well, obviously there’s these good books, but they don’t have maybe the very specific opinions that you and I have about how to try to do this well from a mental health perspective and realistically without Regret is in the subtitle for a reason.  

Dr. Sherry Walling:
I think what’s also interesting is that not only have we been in this sort of consulting seat in las, but we’ve been through an exit. You’ve been through it directly with Drip, and I’ve been through it as your partner, as your significant other. And I think that’s a piece that is often overlooked in business books is the relational impact of some of these transitions, not just on the founder, not just on the founder and their team, but on their family. And this book isn’t a heavy, heavy focus on that, but it is woven through in its, I think really shaped by our experience of having done the reps ourselves and then done them on behalf of other people.  

Rob Walling:
Yeah, there’s definitely a running thread through this book of A, how difficult this process actually is, and B, how much of a toll it takes on not only the founder, the entrepreneur, but on the people around them, their family, significant other, and so on,  

Dr. Sherry Walling:
And that it doesn’t have to be that way. So the default setting is this is hard and can be surprisingly destructive, but it does not have to be that way. So I think that’s the point of the book is to help offer the ability for people to open their eyes, look to see what’s happening, do some self-assessment, and then have some tools to help make more aware and more intentional choices about how they go through this process.  

Rob Walling:
And if someone’s starting a business today and they’re not going to sell it here in the next 12, 18, 24 months, I still feel like there’s value in experiencing this journey alongside the entrepreneurs that we interviewed for the book. What did we enter? 15 people, 20 people. I mean, we did a lot of, it wasn’t just out of in my head. I mean, we did a ton of legwork to pull it in, and there’s a lot of stories, a lot of quotes.  

Dr. Sherry Walling:
I think this book is actually about how to have a healthy relationship with your business, and that’s where it’s relevant to anyone at any phase of their entrepreneurial journey. I think it would be a super great book to read at the beginning because it talks about this balance between going all in and being very careful and very attentive to what the business needs from you and how to protect it well, and how to think about your team and also on the other end of the spectrum, this de-identification between your selfhood and the business that you’re running. And if you can strike that balance well early in your business, I think you are just set up for success in a lot of ways, not just in your exit, but in your mental wellbeing and balance throughout the course of the journey.  

Rob Walling:
And the book’s not out yet. And the reason we’re talking about it today is the day this episode goes live, our Kickstarter for this book goes live. And so folks can head to exit strategy book.com and there’ll be a link there where they can go straight to the Kickstarter page and they can back the book. We’re going to have it in three formats. We’re going to have a hardcover run like I did with SaaS Playbook where we have an offset printer. It’s just amazing. It’s like the same printers who print for any big publisher. And so the quality of the book is just really outstanding.  

Dr. Sherry Walling:
Do you have it there with you? Yeah, I was like, I should have it in my, this is  

Rob Walling:
A digital, I have a digital copy of it that is a print on demand version, but it’s so neat to finally have it here in my hands. And it’s a meaty book. It’s a couple hundred pages, right? 250 pages or so. But with the Kickstarter, we’re going to have an audio version that you and I are going to read together. Isn’t that  

Dr. Sherry Walling:
Sweet? It’s going to be adorable.  

Rob Walling:
It’s going to be so adorable.  

Dr. Sherry Walling:
I’m sure we won’t have any arguments about it.  

Rob Walling:
Nope. During I’m going to leave you, Josh, please edit a lot of any arguments out, but I do like to riff on the audiobook. We haven’t recorded it yet, but that’s something I’m looking forward to doing with you is kind of riffing on different things. And then of course we have an electronic, like a PDF epub version, but in addition to that, we’re offering things that we’ve never offered before, right?  

Dr. Sherry Walling:
All kinds of opportunities to hang out with us either in some q and a sessions where you can come and ask questions about your business, your exit, things that you’re thinking about to one or both of us. I think we have an option where both of us are involved all the way to the opportunity to come to beautiful Minneapolis in the summer and do a founder retreat with the two of us together. So the dates and all the details about that are on the site, but I am personally really excited about doing it that way and the kinds of interactions that it allows us to have with people that we might not necessarily bump up against in our day-to-day lives.  

Rob Walling:
Yeah, I would agree. At one point on this very podcast, it was probably 2021, I did a call for anyone who is in the middle of an exit or really on the cusp of an exit. If you’re thinking about selling, just email me and I will send you a 20 minute zoom link and I’ll zoom with any and everyone who’s going to do it. And part of that was I wanted to talk to more founders who were doing it. But the other thing is I said, this is one of the most important moments slash transactions of your life. And I talked to so many people who were like, I’m going to sell this. I started this kind of listening to the podcast and thought it’d be a little side project, and I got an offer for $9 million, and I was just like, what? And so I had these great conversations and part of those anonymized and everything going to the knowledge bank of writing this book, but I realized through those conversations even more the need for this. You and I’ve been talking about writing this book for three, four years at this point, and it took us, what about a year and a half, I guess, to get it all put together?  

Dr. Sherry Walling:
Yeah, it was such a fun process. There’s obviously lots of different ways to write books, but because we spend so much time talking to each other, podcasting and things like that, I really enjoy the process of having a really detailed outline and then going chapter by chapter and basically recording audio of it and transcribing that and then turning that into the written word. So I think it’s a fun way to collaborate together. And so there really is a mixture of both of our voices in really every chapter, even though some chapters are more based on my expertise and others are based more on your expertise, there’s still this weighing in and question asking of the other person, which I think helps it to be a much better product because you have thoughtful questions that are guiding the development of content.  

Rob Walling:
Yeah, I’m super, super proud of this book. I think it turned out really well, potentially, I hate to say it, but almost better than I could have expected when we started, which is how I like  

Dr. Sherry Walling:
Wow, look at you in the low expectations.  

Rob Walling:
I know, but I like having, I don’t know. I like it when it’s an end product and it’s like, yeah, I know this is dialed in. Something that I really like about the book, as I said earlier, there’s the before, the during and the after your exit. Those are kind of the three sections we have. And one part of the before chapter two, when is it time to go? And we look at external and internal cues for thinking about when you may want to exit. And I remember putting this chapter together, and one of the things that is interesting is that you and I have seen so many people sell that these things just kind of rolled. It was like, let’s brainstorm. Why do people sell? Boom, boom, boom, boom, and then run this list by other people I know who’ve sold. Are we missing any of these? So I feel just really good about the list we put together. Some of the external cues we mentioned are, you’ve built something amazing, the business needs more capital, you’re no longer the best person to run the business. The competitive landscape shifts a change in life status, and another opportunity arises just to give folks an idea of the kind of, and then we dive obviously deep into each of those and how those might come about and how to think about them if you’re in that situation.  

Dr. Sherry Walling:
And also assessing what are helpful motivations to sell and where are, so we talk about some of the internal cues like existential restlessness or energy levels, some even burnout, and when maybe those things lead you to want to sell because you want out, but they’re not always the best for you in the long run or the best for the business. And so thinking through just how to be an observation, an observer of your own mental internal process, and then what to do if you maybe want out, but don’t necessarily, it doesn’t make sense to sell right now. So we sort of dive into some of those options.  

Rob Walling:
And in typical Dr. Walling fashion, this is something I’ve never done in my books. We have making it real at the end of each chapter where it’s like, look, I just told you a bunch of really interesting things and now there are questions to think about and to journal and to take action on. So  

Dr. Sherry Walling:
In my last book Testing two worlds, I worked at the traditional publisher and they really pushed me on this. They were like, your stories are great. Thank you for the wisdom, but what do we do about it? And I, frankly, the challenge of helping people really apply it to their specific situation. So it’s all fine and good to absorb content, but if you can’t do anything with it, then it’s really not in your best highest service. So we’ve worked pretty hard on those sections to give you at least some journaling prompts and thoughtful questions that will help you to go deeper with some of the content that we’ve presented.  

Rob Walling:
And throughout the book, we try to set expectations of what an exit might look like. And I find that we were repeated over and over so much that eventually we had to take it out at a certain point of we just can’t keep saying this, but this is really hard. This is going to be really hard. Isn’t this really hard? That really hard? That felt like a message of the book. Why do you think that we have to say that so often?  

Dr. Sherry Walling:
It’s such a dream outcome. I think the stories that persist on social media or Twitter of the founder who sells for a huge bucket of money and rides off into the sunset or starts a farm in Austin, but it has this glow to it, and I just think that it is kind of giving birth. It has a great outcome. Babies are great, but it’s a grizzly bloody messy process. And because we’ve so glorified the end result, I don’t know that we collectively as an entrepreneurial community have told the truth about the process.  

Rob Walling:
And I think, I know for me, a chunk of the entrepreneurs that I talk to, the founders I talk to who are about exit, I’ll tell them it’s going to be really hard. And I’ve had people tell me, yeah, not for me. It’s not going to be hard for me and then come out together.  

Dr. Sherry Walling:
I got it. I’m not attached to my business. I’m rational. I’m objective.  

Rob Walling:
This won’t be hard.  

Dr. Sherry Walling:
I’m not that worried about it.  

Rob Walling:
I’m so prepared. And then come out the other side like, oh my gosh, you were right. And it’s like, I know it really is as hard.  

Dr. Sherry Walling:
It always, it starts relatively simply. I mean, the wonderful story is somebody gets an LOI and you agree quickly on the terms and it just feels like it’s going to be smooth sailing. But inevitably there’s some series of disruptions in the deal that require sleeveless nights and long conversations with lawyers. And it’s just the way it goes  

Rob Walling:
Inevitably is pretty much my experience. And the interesting thing is as entrepreneurs, we do hard things and we think as you said, that it’s like we can logic our way out of it or that we can just, we’ve done hard things in the past and I know that I can do it, but you get in this position where it’s like, all right, I’ve signed this letter of intent for $10 million and we’re going to close in 45 days, 45 days. I could do anything for 45 days. And then suddenly you find that you’re like, whoa, there is a lot of uncertainty here. And whoa, there are a lot of people that are kind of pissing me off here with the pushback on the thing and asking for the stuff. And you start to get in your own head. People start sleeping. There are entrepreneurs who you can’t sleep so stressed about it. And then you get towards the end and everything’s up in the air still.  

Dr. Sherry Walling:
And then it’s not 45 days, it’s 50 days, it’s 60 days. It’s the lawyers on vacation. Yeah.  

Rob Walling:
And so that is something we talk about. We have, I mean obviously there’s what, 14 chapters in the book and only two of them are really about deal structure and deal points because again, there are really good books like the Art of Selling Your Company that cover that type of stuff. So the vast majority of the book is thinking through whether to do it and how to do it well, and then how to be on the other side and ask what’s next. But I really like in chapter seven, it’s called collateral Damage, minimizing negative Impact. And we talk about minimizing negative impact to your mental health, your physical health, your family, your team, your company, and the deal itself. And then we have specific strategies for that. It’s learn how to time travel, take on an exit project, go on that vacation, let your partner in on your emotional state and other things. A lot of those came from you. I mean, I was pulling out the, here’s all the collateral damage it can do, but really the strategies for how to minimize those or how to stay healthy, a lot of that comes in your voice, a lot of your work.  

Dr. Sherry Walling:
It really is a challenge to construct some internal buffers around your own anxiety, especially for entrepreneurs who have often used their anxiety or their agitation as fuel to get things done. But in this process, you can only get done what is on your to-do list in that moment. And then you are waiting on all of these other people, on the buyer, on the broker, on the whoever else. And so it’s a really abrupt, difficult lesson in holding agitation and anxiety when there’s nothing really effective to be done with it because there are things that are happening or that you have to wait for that you can’t control. And so a lot of these strategies are around what to do with that energy, frankly, how to not let it eat you alive and not let it spin out of control in a way that hurts the people around you and leaves you trying to push the deal forward or being thoughtless or reactive because you are uncomfortable and agitated.  

Rob Walling:
I like that you bring up that point of there are things outside of your control that you just can’t do anything about. Because again, as entrepreneurs, as founders, we start companies, some of us because we want to control everything. And suddenly you’re in the middle of a process where it’s like some clown shoes, lawyer on the other end, as you said, is on vacation or is taken four days to turn things around and you’re like, dude, this is $10 million. This is the biggest thing of my life. This is my life. But it’s just another day for them. It’s just another deal.  

Dr. Sherry Walling:
Just another email.  

Rob Walling:
And we talked through in chapter 10, we have the 3:00 AM what ifs. And all of these quotes are things that you and I have either heard from entrepreneurs or we heard in the interviews as we talked to entrepreneurs, things like, what if my team falls apart? What if the deal falls apart? What if I’m not up for this? What if this deal is my only chance? What if I take a bad deal? And there are more, there are a lot of 3:00 AM what ifs. Another thing that I don’t think is talked about enough is life after the exit. We have a chapter called Purgatory that is sad. It’s about working for the acquirer and reporting to a boss. You lose control of your team, of your company, but there are also a upsides to it as well. And that was something that I am really glad we covered.  

Dr. Sherry Walling:
I think this question of life after the exit is maybe some of the content that I’m personally most proud of that feels like a real contribution to this conversation around exits that I just haven’t seen dealt with as thoughtfully and as carefully as we’ve dealt with it. And I think coming from my life as a psychologist, there is this deep appreciation for what it means to be going through a really significant life-changing developmental disruption at a time when your peers aren’t going through that exits are such extraordinary events, they’re just not commonly occurring. And so it’s like getting divorced or sending a kid to college or watching your parents pass away. It’s this major reworking of your identity and what you do during the day and what matters to you. But you’re not doing that along with your peer group. You and I know lots of people whose kids are going to college because that’s the age group that we’re in. And so this idea of going through a major developmental transition alone is pretty unusual and kind of extraordinary in the human experience. And so I think giving people some grounding in that, some understanding and some perspective about why this reworking of your entire life midstream is so challenging and then what to do about it, how to avoid the isolation and how to avoid the kind of spin out that can happen when people lose perspective about just how significant this transition is.  

Rob Walling:
Yeah, I like that you call that out. A lot of people have kids who go to college. A lot of people have a parent who passes away. A lot of people get married, get divorced, have children, whatever. There’s a lot of events that completely can turn your life upside down. And so few people sell a company and so few people, I mean almost no one else is selling a company when you are. And what’s interesting is during the sale, again, there is only so many people you can talk to. We do have a whole chapter on support team and how to put together people to support you, but afterwards, there can be this sense of, shouldn’t I be happy now? Hey, my company was really stressing me out. I don’t have to work on that anymore and I have this huge pile of cash in the bank, but now I’m unhappy. We have this expression whining on the yacht. It’s like you can’t just go on Twitter and say, man, sold my company for $10 million. Life sucks. And I’m so sad every day  

Dr. Sherry Walling:
I’m so bored and lonely.  

Rob Walling:
Totally. Even if that’s really the case. And we talk a lot about that of first day of the rest of your life, like how to recover from this and how to find a peer groups. There are other entrepreneurs who’ve gone through this  

Dr. Sherry Walling:
And to re-anchor into meaning you’re getting a second act, you’ve built something, you’ve gone through the whole journey and then sold it. And it is an immense opportunity to use the phrase that from David Brooks to climb a second mountain to do something else that is interesting and meaningful and valuable to you and to your family and to the world around you. But people have a complicated relationship with that. Sometimes people rush, they can’t tolerate this in-between space, the patients of really considering what’s next. So they buy a company before they’ve finished selling their other company, we tell this story in the book, or they get so churned around about what to do next that they spend years spinning their wheels, not doing anything. So this conversation about what to do next is really important because it does help people re-anchor to what they want their lives to be about in this next iteration.  

Rob Walling:
And we talk about it in, well, we talk about purgatory of, Hey, you’re working for the acquirer still, where it’s this weird in-between of I’ve sold, I have this money, I don’t control the company anymore and I got to figure out now how to be an employee. But then once you do have that break, assuming you move on from that at some point after an earnout, then we talk about how to recover, how to rest up, how to physically recover, connect with yourself and as you’re saying, take stock of the past, embrace the present and look ahead and ask yourself what’s next and with what’s next, there are a couple traps we call out that we’ve seen over and over. It’s the prove I can do it again, trap and the sail away forever trap. Why do people fall into these same traps over and over?  

Dr. Sherry Walling:
It’s so deeply part of us, this story that we create about who we are because of the business that we’ve built. And so the proof I can do it again is about, look how good at entrepreneurship I am. Look how creative look, how it’s just look who I am based on this outcome that I can create. And the pressure to try to do it again just as to reinforce your perception of your identity and then the sail away forever. Ever trap is a little bit like, I don’t need any of it. I’m just going to go retire on a beach in Mexico, which is also not true for the vast majority of entrepreneurs. It’s not an accurate read of themselves. So it’s about needing too much to be an entrepreneur in the prove. I can do it again, sense or not having a proper respect or reverence for how deeply you are a maker and a creator in the sail away forever trip. So finding your balance between those two edges of the spectrum.  

Rob Walling:
And of course, we also, I like this chapter title, what do you Do with a big pile of money? We talk about how money reduces your circle appears and how it changes your friends and your family relationships and even romantic relationships. So obviously this is not a book on specific investing advice, but we do dabble a little bit in that as well. I really liked one quote in that chapter where a founder said, I had all this money and traditionally I’d been investing in index funds and just kind of following the basic financial advice that you would do. And now I had all this money, so I invest like a rich person and started making risky bets and investing in private equity and this stuff that’s not necessarily, it’s like you still Vanguard Index funds or Schwab index funds are still really, really good, even if you have 10, 20, $30 million that you need to invest.  

Dr. Sherry Walling:
Well, again, that speaks to this identity piece, right? I was a scrappy founder and now I’m someone with a big bank account. So doesn’t that mean that I act or hold myself in this different way that my identity shifts now that I’m a rich person or now that I’m a post exit founder? And that’s not necessarily true. Your identity is your identity. You can weave it through these changes, but we have this idea that we put on these certain roles and then act accordingly to those roles. And so I think the theme of the book really is about being able to step back and to see your pull to some of those default settings, and then the ability to choose whether that setting really fits or doesn’t, whether there is a way that rich people invest or not.  

Rob Walling:
And then to cap us off, I’m not going to tell the story, I’m just going to tease it, but one of the cringes stories in the entire book is when you ran over my original Andy Warhol in your Porsche,  

Dr. Sherry Walling:
That did happen,  

Rob Walling:
And I’m going to leave that there. I’m a person who does not identify as a rich person, and yet there you go. That actually happened. So in order to hear that story, you’re going to need to go to exit strategy book.com, back the Kickstarter, and we look forward to getting this book in your hot little hands. Dr. Walling, thanks so much for joining me on the show. Folks want to keep up with you. They can follow you on X Twitter at sherry walling and zen founder.com is your home on the internet, and you have a newsletter that you send out every week as well as a podcast called Zen Founder. Thanks again for joining me.  

Dr. Sherry Walling:
My pleasure. See you in the kitchen.  

Rob Walling:
Thanks to Dr. Walling for joining me on the show. And thank you for joining me this week and every week, exit strategy book.com. If you would like to pick up your hardcover copy, this is the only hardcover printing we will do after these ship. We will then have print on demand paperbacks from Amazon. So if you want to get the fancy schmancy version, these look really good. Honestly, again, I’m really proud of what we put together. Head to exit strategy book.com. Thanks so much for joining me this week and every week. This is Rob Walling signing off from episode 740.