Episode 743 | How to Sell Your Business Without Regret

Rob Walling:
I’m Rob Walling and in this episode of Startups For, the Rest, Of Us, my wife, Dr. Sherry Walling and I read chapter one of our new book called Exit Strategy, the Entrepreneur’s Guide to Selling Your Company Without Regret. This effectively will become the intro and first chapter of the audio book, so you get a free preview of the audio book to see if you might like it. The Kickstarter for this book closes this week on December 12th. You can of course go to kickstarter.com and search for exit strategy or you can follow the link in the show notes. It would be amazing to have your support. This campaign is not doing as well as the SaaS Playbook did, and so every bit helps, every pledge helps, and even if you are not thinking about selling your business today, I believe it is never too early to set yourself up for success, even if it’s months or years down the line when you decide to sell. 

And this book talks about all this stuff to think about before, during, and after. And the before section is super helpful even if you aren’t thinking about selling today. In addition, applications for the all new MicroConf Connect are closing today. December 10th. MicroConf Connect is our application only membership and we only open applications once per month to ensure everyone who’s accepted is onboarded together in a cohort and that we can give them the support they need. All members who sign up will have access to an Ask Me Anything with me on December 12th. If you miss the application date though, you can make sure to sign up for the wait list. We’re going to reopen applications after the new year. That’s MicroConf connect.com and with that, let’s dive into the intro and first chapter of Exit Strategy. You’re listening to Exit Strategy, the Entrepreneur’s Guide to Selling Your Business Without Regret. Written and narrated by Sherry Walling, PhD and Rob Walling,  

Dr. Sherry Walling:
Not PhD.  

Rob Walling:
Well done  

Dr. Sherry Walling:
Rob Walling Odd Blank Space.  

Rob Walling:
Thanks for pointing that out. This book has a forward by John Warlow, the author of Built to Sell and several other books about selling your company.  

Dr. Sherry Walling:
He’s a pretty smart person,  

Rob Walling:
Very smart. It was awesome to get his forward book is Copyright 2024 by Rob and Sherry Walling. There’s a lot of praise in here. John Warlow, Jason Cohen, Derek Sivers, JJ Virgin, Sam Parr. Ben Chestnut. I think we did good. I really appreciate everyone who wrote us a testimonial.  

Dr. Sherry Walling:
How much did you have to pay those people to say nice things about this book?  

Rob Walling:
Exactly. $0 and 0 cents. Did send an email to them though. Really appreciate  

Dr. Sherry Walling:
That. Thanks y’all for saying nice things about the book and reviewing the book. I mean, a bunch of them actually read the book.  

Rob Walling:
That’s the dirty little secret right of author blurb. Testimonials is most of those are just because someone and they don’t actually endorse the book, they don’t read it, but I get the sense that most or all,  

Dr. Sherry Walling:
Most of our people, this book,  

Rob Walling:
Yeah,  

Dr. Sherry Walling:
This book is dedicated to Genesis Riley Cook being her guardian parents taught us a great deal about going all in on love and letting go with grace. So let’s jump in. This is the introduction. The last days exiting your business with intention. It feels like I’m going through a divorce. This is the most stressful thing that’s happened to me outside of my wife getting cancer. Is it reasonable to feel like this is one of the most difficult parts of my life? These thoughts are not what you would expect to hear from someone in the midst of an event that will leave them millions of dollars richer, but we hear them all the time. Different wording, different dollar amounts, the same sentiment I’ve been working my whole life for this moment. Why is it so painful? Selling your company is one of the most fragile points in the life of an entrepreneur. 

It is a messy psychological process, often accompanied by an implosion of identity and emotional stability. It requires an extraordinary amount of focus over a long period of time. It disrupts your sense of meaning, your sense of accomplishment and your vision for the future. It’s extremely challenging for your personal and professional relationships. Exiting a business is a transformational experience that few people have Beyond the headlines and highlight reels, there’s sparse conversation about how to do it well. We have a few models to describe the nuts and bolts of the process, but none to guide the deeply personal aspects of a monumental deconstruction and reconstruction of one’s life. We call an exit transformational because it involves change at every layer of life. From the way you introduce yourself to how you begin each morning, what your bank account looks like and the fears that keep you up at night building and then leaving a business is emotionally similar to raising a child who heads off to adulthood and inadvertently fires you from the day-to-day tasks of parenting. 

You can do everything right and have a wonderful outcome for all your labor and still feel deep emptiness and disorientation. Like any good story, your business has a beginning, a middle, and an end. There’s the seed of a dream that kicks off the adventure. There’s the arc of the story complete with try fail cycles, emotional peaks and valleys and plenty of high stakes, and then there’s the big finale, the exit. You will exit your business. You might sell it. You might go public and get voted out by the board. When you don’t hit your quarterly targets, you might shut it down either by choice or because you feel the story arc has finished or because you run out of money. You might choose to step into retirement and hire someone to take over day-to-day operations. You might die and leave the spreadsheets and shipping deadlines to be decoded by your co-founder, COO or spouse. 

One way or another, your relationship with your business will end and although there are several ways this relationship can end, this book focuses on exiting via a sale. This is the exit most entrepreneurs aspire to achieve, one that warrants significant preparation and planning. Every founder knows this intellectually, but if you think about their exit until it’s too late and no one is prepared for how hard it’s going to be, the good news is that you get to shape the story arc of your company. You get to participate. Are you writing the story or is this story writing you? There are plenty of books about major life transitions from aging to divorce to empty nest. The sheer volume of self-help and practical guidebook speaks to how difficult and momentous these major midlife shifts are for the human psyche. However, few books prepare you for selling your company. 

Of course, exits are not nearly as universal as kids leaving home or the slow transitions of aging, but for the millions of people who identify as entrepreneurs, some kind of exit is inevitable. This significant and disruptive experience in the life of the business owner is not given the thought or attention that it deserves. Exits are complicated. They are financially and legally intricate. They are incredibly stressful. There are many relational implications. They also rearrange a founder’s identity in deeply felt and widely sweeping ways. No matter where you are in the process, it’s important to prepare yourself for your exit to achieve your optimal outcome. You must be mindful about setting yourself up for the exit trajectory most congruent with your goals. Exits are not magic. They don’t just happen one day when the money wizards stops off at your office with a wheelbarrow full of cash. They are usually the result of careful planning and thoughtful decision-making. Failing to prepare can result in many complications even if you do achieve your optimal outcome and sell to someone you trust. For buckets and buckets of money. A simple truth remains. Selling is one of the hardest experiences of a founder’s life.  

Rob Walling:
When we tell this to entrepreneurs, they rarely listen. They nod and they smile politely. They hear what we’re saying, but they don’t really listen. After all, every part of entrepreneurship has been challenging and if they’re going to sell anyway, what does it matter that it will also be hard. We’re not telling you this to scare you off. You already know selling will be hard even if you don’t yet know how hard and who better to prepare you for this difficult journey than a clinical psychologist specializing in entrepreneur mental health and a serial entrepreneur with 20 years in the trenches supporting founders through the full scope of the entrepreneurial journey.  

Dr. Sherry Walling:
Hey, that’s us.  

Rob Walling:
That is us. Between the two of us, we’ve seen hundreds of founders through their exits. Dr. Sherry has been helping entrepreneurs with their mental health relationships and big decisions since 2016. Prior to this, she spent 10 years helping people put their lives back together after trauma loss and major disruption. She has deep expertise in grief along with personal experience coming back to life after a significant loss. For more on this, check out her book Touching Two Worlds.  

Dr. Sherry Walling:
As the co-founder of MicroConf for TinySeed, Rob has worked with thousands of founders across all stages of business. He has also started six yes, six companies and gone through multiple exits including his successful and wildly stressful exit from Drip.  

Rob Walling:
Did you roll your eyes when you said six companies? Like each one of those took years off your life?  

Dr. Sherry Walling:
Yeah. I can name all of my gray hairs and wrinkles after the companies that  

Rob Walling:
After each of the companies, our first book for startup founders, the Entrepreneur’s Guide to Keeping Your Shit Together, how to run your Business without letting it run You helps you navigate the beginning and middle of your business’s story arc. This book is about nailing the big finale. In writing this book, we aim to shine a light on the path before you so you can see the challenges and pitfalls ahead. We can’t make those challenges and pitfalls easier, but we can prepare you to face them. Our goal is this to help you protect your family, your relationships, and your mental health while working toward the best possible exit for you and everyone in your company. This book offers frameworks to simplify the complex mental, emotional, and relational challenges of exiting. It draws on the combined wisdom of thousands of founders we’ve coached, talked to, laughed with, cried with, and advised over the years.  

Dr. Sherry Walling:
You’ll also hear firsthand lessons from Rob’s own experiences selling his companies and my experience during him on as well as insights gleaned from interviews with other entrepreneurs about their exits.  

Rob Walling:
Finally, we provide practical strategies to help you exit well. We will touch on the elements of a deal and some basics of negotiation, but this book focuses more on the space between your ears than the line items in the contract. For detailed guidance on deal structure and company preparation, see our resources at the end of this book for well-crafted, practical content about preparing your business for your departure. Whether you’re selling an e-commerce company, a children’s brand, a trapeze franchise, a consulting agency, or a software as a service or SaaS business, we’re here to help you prepare. Every exit is unique and there’s no such thing as a game plan that will lead you through all the steps. As the Spanish poet Antonio Machado wrote by Walking the path is made and when you look back, you’ll see a road never to be trodden again. No one can tell you how to walk the path, but we can equip you for the journey. Let’s get started.  

Dr. Sherry Walling:
Let’s get started. Section one of the hardest things you’ll ever do. Chapter one. Why is this so difficult? Julie Ellis and her three co-founders hadn’t intended to sell their beloved children’s label company Mabel’s labels, but when one of the largest companies in their space made a $12 million offer, the four co CEOs decided it was time the business structure of four co-founders with equal decision making power was starting to feel too slow for the rapidly growing company Julie told us in an interview, yeah, that makes total sense to me. For people making decisions is a lot. Plus, after 13 years of pouring all their resources into building the business, the sale would provide each of them with a nice nest egg for retirement. There comes a time when getting your money off the table starts to look pretty appealing. She said the timeline was aggressive less than six months from the first talks to the closing date, but the acquirer checked the boxes. 

Julie and her co-founders wanted checked. They were Canadian owned and would let Mabel’s labels keep running on its own rather than dismantling and absorbing it. It seemed like the perfect situation, but Julie quickly learned how exhausting selling a business could be. The exhaustion only grew as she went to work for the acquirer immediately after the sale and realized that the marathon finish of the acquisition was actually the starting line for a new kind of race. Six months after the sale closed, she left the business. She thought she would never leave exhausted and uncertain about her next direction. As entrepreneurs we’re always climbing for a pinnacle, Julie said, but there’s always another pinnacle after the first one and another one after that, and many entrepreneurs fall into the trap of dismissing or diminishing their accomplishments. We have an inability to find a plateau and rest on it. 

For a little while, said Julie. For Julie, the exit was a vast plateau. It should have felt like a victory, an opportunity to rest, but her entrepreneurial mindset was trained to keep pushing for the next accomplishment. Sitting on that plateau sparked an avalanche of new questions. Is this the best I will ever do? What will happen next? Was it a mistake? Even when an exit is going smoothly? The untold story is that many founders experience a significant mental implosion during and after the process. It’s possible for something very good to happen while still feeling a lot of emotional turmoil or conflict. These emotions can coexist. Talk to anyone who’s had a baby gotten married or started their dream job, and you’ll often hear that the joy was accompanied by a sense of inner disorientation. Exiting is an emotionally tumultuous event and it’s worth taking the time to prepare your mind as well as your business. We are not trying to scare you, but time and time again entrepreneurs have said how surprised they are that selling their company is so hard. If you go into it with eyes wide open to the challenges and armed with strategies to get through them, you’ll be miles ahead of someone who’s going into it with the magical thinking of signing some documents that yield a personal bucket of money and a room full of elated employees, friends and family members. So let’s start by digging deeper into the psychology of what makes this process so difficult.  

Rob Walling:
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Your business is your baby. Entrepreneurs are deeply connected to their businesses and a study of entrepreneurs, emotional experiences and neurological activation. Scientists used functional MRIs while asking entrepreneurs to think about an image of their business. They conducted the same experiment with parents asking them to think of an image of their child. When comparing the brain activity of both groups, they found remarkably similar activation patterns. Specifically the study showed that activity was suppressed in regions of the brain involved in critical assessment. Specifically, the study showed that activity was suppressed in regions of the brain involved in critical assessment, while it heightened in areas associated with the brain’s reward center. In real world terms, this means that entrepreneurs and parents experience a similar sense of delight and satisfaction when thinking about their beautiful, perfect, above average children or businesses. Whether we’re thinking about our children or our businesses, our perceptions are not entirely objective. Both entrepreneurs and parents tend to view their subjects with a positive bias rather than objective clarity. Running with the parent analogy, you may rationally understand that your relationship with your children will change as they mature. You may also know that the goal of parenting is to raise autonomous independent individuals who do not live in your basement. 

Our 8-year-old moved out, went to college and currently lives in our basement, so this one hits a little close to home.  

Dr. Sherry Walling:
Whoops, we might not be very good at this.  

Rob Walling:
You may even be emotionally ready for your 18-year-old to leave home to preserve everyone’s sanity. However, understanding this doesn’t make the transition any less emotional or challenging. It’s not so different with a business. If you’ve built it well, there will come a time when the business outgrows you, but neurologically speaking, entrepreneurs often don’t perceive a clear separation between themselves and their businesses. This means that no matter how you pride yourself on being, it’s incredibly difficult to see yourself and your business objectively during and after your exit. When you commit so much of your time and energy to the formation and growth of a business, it is perfectly natural for the business to become an extension of your identity. You intertwine yourself and the business and other people may see you and the business as intertwined. Those years of intertwining get unraveled in an exit, A topic we’ll explore in the latter half of this book, there are psychological pros and cons to thinking of your business as your baby. Generally speaking, it isn’t a great idea to tie your wellbeing to an external entity that is highly vulnerable. Just social media algorithms or the supply chain from China. Too much of your identity is wrapped up in things you can’t control, but regardless of whether or not it is optimal, the neural imprinting between a person and their business is substantial and consistent.  

Dr. Sherry Walling:
Another reason it’s difficult, you’re entering the unknown. Businesses tend to grow slowly. You have the seed of an idea and then spend months or years on your own building it into something people want. You create your team slowly refining your product and growing your company until you suddenly look around and realize you have 20 people working for you. And then in a move that can feel like it happens overnight, you begin an exit process. You find yourself in a new location, a new world. The sudden shift is disorienting to say the least.  

Rob Walling:
Here’s a quote from a post exit founder. As a first time founder, it’s scary. Giving up a business is going well and recognizing whatever good fortune that allowed you to thrive might not be repeatable.  

Dr. Sherry Walling:
It’s not just the suddenness of an exit that’s disorienting. It’s also the potential loss of your identity, direction, and purpose. Returning to psychology, if you consider the typical progression of human development, we see rapid changes in our early lives. We try on adolescent identities, a jock, a punk, a goth. Oh yeah, I like the breakfast club. We leave home for college, perhaps switch our career paths a few times. We enter into and leave intimate relationships. We establish ourselves professionally. We purchase homes and couches to cats in a fish tank. We might have children. We start companies. As we age, the rate of these life-changing events slows down. We can no longer move apartments in one afternoon with our cousin’s pickup truck. We grow comfortable with our stable lives and identities. Mature adulthood means that generally we know who we are and how our life operates, and then we face an exit and we’re thrown into the unknown once more because of the depth of the relationship between the entrepreneur and the business. This is not a casual unknown. It is a deep unknown, a fairly comprehensive recalibration of who we are and how our life works. Most dramatic life-changing events that happen in the middle of adulthood are traumatic, like a car accident, a divorce, the death of a parent. What comes after the can be daunting. The exit creates instability and unpredictability, and after years of leading and directing the path of your business, it requires you to surrender control. It can feel like going backwards.  

Rob Walling:
Here’s another quote from a post exit founder. It’s not often as a 43-year-old, I have a major life decision. Most of what we want at this point is predictability, and the uncertainty of what comes after this is daunting.  

Dr. Sherry Walling:
It can feel like you’re 18 again and wondering what the hell you’re going to do with the rest of your life.  

Rob Walling:
On top of all that, going through an exit is incredibly isolating. Think of it like an iceberg. The tip of the iceberg is the public perception of what you’re going through. Everything below the water is what you’re actually experiencing from the perspective of your employees. Team members and the public exits are seen as times of celebration. Pop out the champagne and the celebration emojis because now you’re a millionaire, right?  

Dr. Sherry Walling:
Which is the celebration emoji.  

Rob Walling:
There’s a confetti one, and then there’s one that looks like a bullhorn with confetti around it. I think if you type in colon confetti, oh, that’s in slack anyways,  

Dr. Sherry Walling:
Alright,  

Rob Walling:
And while that’s partially true because getting millions or tens of millions of dollars wired to your bank account is a pretty incredible moment, that’s only the tip of the iceberg. The rest is an incredibly nuanced experience that the founder goes through alone. You’re trying to make the best decision for yourself and your business processing a complicated multivariate analysis in your head, and often you might be legally barred from talking about what you’re working on. When I sold Drip, I experienced a barrage of congratulations. While mentally I was almost at my breaking point. This created a deep sense of disconnection because it was nearly impossible to talk about the realities of the exit due to non-disclosure agreements or NDAs and the dearth of people who could relate to my experience. Exiting is a low frequency event. There just aren’t that many people who’ve done it. Many other major life transitions are universal puberty, completing high school, choosing a life partner, pregnancy, the death of a family member, a child departing home and aging. They’re challenging shifts, but almost everyone has experienced them. There’s plenty of collective wisdom and guidance available to help you navigate these difficult transitions, not so with an exit. It’s a pretty small club and you have to work hard to find commiseration guidance and support as you enter this unknown territory  

Dr. Sherry Walling:
And there’s no blueprint. Another factor that adds to the feeling of isolation is that there’s no blueprint. Exiting is like a fingerprint. No two look exactly the same. As we mentioned, exiting is a low frequency event. It’s also a high variability event, which means that even the few other people in the world who have gone through an exit haven’t gone through your exit. If you and I both decide to sell our houses today, there’s a relatively standard process to follow. It’s a high frequency, low variability event. Sure each home is unique, but millions of homes are sold around the world each year. Even if you haven’t sold a house before, you probably know a dozen people who’ve been through the process and there are standard templates you can follow selling a business. On the other hand, each experience is unique. Maybe you’re part of a mastermind or run in entrepreneurial circles and even have other friends who are founders, even if that’s the case, and even if some of them had gone through their own exits, the chances that someone has gone through your exact scenario are very low. No one can hand you a blueprint for exiting your business. The number of variables is just too great and there’s never one right answer. When selling your company, your hand sketching your blueprint while the backhoe digs the foundation  

Rob Walling:
And all that got you here, won’t get you farther exiting well requires a new set of skills. During the course of running your business, you’ve learned how to build, how to sell your product, how to market, how to lead your team, how to build a profitable company. None of those skills apply to what you’re about to do. In fact, the main drivers that got you to this point, your passion for your product, your commitment to your team, your dedication to your business can stand in the way of a successful exit. Many entrepreneurs have difficulty making clear decisions during a sale because they care so much about their team and their business. You’ve spent years or decades building something incredible and developing the passion to run it. After all, everyone’s got the cutest baby right now. Not only do you have to go through one of the most difficult and isolating times of your life without a blueprint, but you also have to unlearn old habits and teach yourself a brand new set of skills  

Dr. Sherry Walling:
And it’s irreversible. If you hire the wrong engineer, you can fire them and find a better fit. If you develop a feature that turns out to be a dud, you can always scrap it and try something new. If you invest in a marketing approach that turns out to be a waste of money, you can also change course. Those are reversible decisions. You can make them relatively quickly without too much stress. Exiting your company though is irreversible. Sure, we’ve all heard of people who repurchased a company after they sold it, just like we’ve heard of couples who got back together after a divorce. But both situations are pretty rare. Because of this, it’s not a decision you should make quickly. It should stress you out. You should spend a lot more time thinking about it than you did thinking about who to hire for that engineering role. The decision is irreversible, so you should make damn sure it’s the right decision, except  

Rob Walling:
You can’t see the future, which means there’s absolutely no way to know if you’re making the right decision. All you can know is that you’re making a decision, which is hopefully the best decision you could make with the data you have. You can run various calculations and imagine what life might look like if you continue to grow the business for another 20 years versus selling it now and walking away with a specific dollar amount. However, you can’t actually know how any of these scenarios will ultimately turn out. We know founders who wish they hadn’t sold, founders who felt like they sold for too little, and founders who declined an offer that in retrospect was a once in a lifetime deal. There are many potential scenarios for regret. With the benefit of hindsight, they might have made a different decision. None of us can see the future though. The only thing you can do is make the best decision you can with the information you have right now.  

Dr. Sherry Walling:
So now let’s shift to six factors that shape how you feel about an exit and our experience working with entrepreneurs. Six factors strongly predict the emotional process of an exit. So we’ll discuss these factors throughout the book. The first one we want to talk about is motivations. The reasons behind your decision to sell the company significantly impact how the process will affect you mentally. Are your motivations purely financial? Are you seizing of lucrative market opportunity or strategic acquisition? Are you feeling called to shift into different or more meaningful work? Are you selling off one product to concentrate on the success of another, or are you selling somewhat reluctantly due to unexpected life changes, burnout, fatigue, or depression? When you understand your motivations, it helps clarify what a successful exit looks like for you regardless of your situation. It also helps you gauge the emotional reserves you have available for the exit process. Beginning an acquisition process while experiencing burnout is like running back-to-back marathons. It’ll be highly emotionally challenging. It’s crucial to be aware of your energy levels and core needs as you navigate the process.  

Rob Walling:
The second factor is tolerance for uncertainty. If you started a business, then tolerance for uncertainty is your bread and butter. But as we’ve mentioned, the level of stress and uncertainty during the exit process is a whole new ball game. Founders who have a high tolerance for uncertainty will have an easier time during their exit, but even if that’s you, it will require all of your coping skills to rise to the challenge. It’s worth assessing those coping skills. Now, take stock of the ways you tend to deal with uncertainty, both positive and negative, and create a plan for implementing or mitigating them during your exit.  

Dr. Sherry Walling:
The third factor is good old fashioned stamina. Exits take longer and are more complicated than anyone imagines at the outset. Even if you have a fantastic strategic buyer and the purchase price is agreeable and the details seem to be lining up, it always takes longer than it should. There’s a lot of paperwork. There are many people, employees or customers who need to be brought along strategically with thoughtfully crafted information. Pace yourself and prepare yourself mentally to run a marathon.  

Rob Walling:
The fourth factor is team psychology. The way an entrepreneur views their team is another critical factor. What is your relationship like with your team? Do you see them as family? Are they literally members of your family, friends from high school? Are they a curated workforce that you’re paying to do their jobs? How do you see responsibility to them when you’re setting yourself up to exit? Hopefully with a nice pile of money, your existing relationship with your team will significantly impact how you feel about exiting.  

Dr. Sherry Walling:
Number five, identification with the business. How closely do you identify with your business? Whether you built it from scratch over decades or have been running it only a few years? At least part of your identity is probably closely tied to your company. As you consider your exits important to find meaning and engagement in other areas of your life, your hobbies, family, community, and other passions. Exiting a company can feel like cutting off a limb, but founders who have found a meaning in other parts of their lives tend to have an easier time. The earlier in your business journey that you begin to separate yourself from your business, the better for you and for your business. You may want to ask, how well can this business run without me? The business may be more valuable. It almost certainly will be more valuable if it isn’t tied to you and you are healthier pre, mid, and post exit. If your sense of worth as a human being isn’t intertwined with your business.  

Rob Walling:
The six factor is a sense of what’s next. It’s easy for a founder to get so wrapped up in the exit process that they’re not thinking about what comes after. However, it’s healthier to start thinking about future plans and gently engage with those plans as early as possible. We use the word gently because rushing into a plan to offset the uncertainty can be problematic. Instead, approach it with a sense of exploration. Gently noodle through ideas. Don’t solidify them by pouring concrete. The question of what’s next can either haunt you throughout the exit process or serve as a north star that guides you into the next phase of your life.  

Dr. Sherry Walling:
So at the end of each chapter, we decided to make these little sections called making it real, and in ’em they’re kind of like practice assignments. These parts of the book where we want to translate the content of the book to something that you can actually use and apply to your life. So for this first chapter, the Making it Real section says, start your exit journal. Grab a notebook or open a password protected document and write down what a good exit would look like for you in this exercise. Practice active imagination. Close your eyes and imagine your last day at your company. Imagine some last act like locking your office door, closing your laptop, offering a goodbye hug to one of your team members. In your imagination, examine yourself. How old are you? What is your emotional state? How do you feel about this ending, this last act? And now let’s jump scenes. Imagine you are telling an old friend about the last day at your company. Imagine that you are happy, proud, satisfied that your exit went exactly as you’d hoped. What’s the story that you tell them? Who was the acquirer? What was the sale price? Where are you taking your loved ones for a celebration? Now, begin to imagine yourself in this scenario. It is one way to practice a not yet experienced reality,  

Rob Walling:
And we wrap up chapter one with a sidebar titled, think About Your Exit Before You Get Started. Ideally, you’ve been thinking about your exit since day one. A good exit strategy is like a prenup in a marriage, especially if you have a co-founder,  

Dr. Sherry Walling:
Hey, do we have a prenup?  

Rob Walling:
No, our net worth was like $8,  

Dr. Sherry Walling:
But I had a guitar.  

Rob Walling:
That’s true. $8 plus a guitar. Entrepreneurs who have never thought about it usually find themselves blindsided three, five or 10 years into a business when life circumstances change, they get tired of the business or they get an offer with a shocking number of zeros. Everyone exits. If you don’t plan for it early enough, you’ll find that your business isn’t prepared to go on without you once the day comes. And if you don’t think about yourself exiting, you’ll be emotionally jarred when you find yourself pondering. Now, what do I do with myself? In your mind? Begin to see an exit as a universal stage in the lifecycle of any entrepreneur. Make it the assumption, the default setting, not to get too dark about it, but a helpful analogy is thinking about exiting your business, like making sure your affairs are in order for the end of your life.  

Dr. Sherry Walling:
That is dark, dude. Nobody’s going to die.  

Rob Walling:
Nobody’s going to die.  

Dr. Sherry Walling:
Oh wait, whoops.  

Rob Walling:
People are depending on you to leave your business in good shape. If you suddenly need to leave, there’s no way around death. Taxes and exits. Have an ongoing open dialogue with yourself and the relevant people, even if it’s just a password protected document where you can jot down thoughts and explore your exit ideas from time to time. Whether or not you can visualize the end of your relationship with your company, start having that conversation with yourself today. Don’t wait until you’re forced into it without having enough time to think and plan. You might miss an opportunity because you were unprepared to seize it, and definitely don’t wait until you’re in the middle of stress and burnout to make some of the most important decisions of your business life. Though, if that’s you, we’ll walk you through that process too.  

Dr. Sherry Walling:
Hey, good job reading.  

Rob Walling:
Yeah, you too.  

Dr. Sherry Walling:
You read. Good.  

Rob Walling:
Thanks for joining me on the show. I know I grew up reading and writing and arithmetic and  

Dr. Sherry Walling:
Speaking English.  

Rob Walling:
Speaking English. Well, thanks for joining me on the pod here.  

Dr. Sherry Walling:
My pleasure. Thanks for writing a book with me.  

Rob Walling:
How’d it feel reading that first chapter? We have not read the book out loud. It really well.  

Dr. Sherry Walling:
I just gave a talk about the content of the first chapter, so I didn’t read the book, but I actually used some of the language verbatim, so I felt like, oh, I’ve have actually read this out loud before.  

Rob Walling:
Did you just say I haven’t read the book, the book that we wrote?  

Dr. Sherry Walling:
No, I haven’t read it out loud.  

Rob Walling:
Oh, got it.  

Dr. Sherry Walling:
I’ve read it multiple times.  

Rob Walling:
Like proofreading. Yeah,  

Dr. Sherry Walling:
Yeah. But I have not read it out loud. It’s not been the book that our children have requested for their night night pre-B bedtime story being as they’re 18 and 14.  

Rob Walling:
I think it felt good. It holds up. It’s always a different experience reading something out loud.  

Dr. Sherry Walling:
Yeah, I mean, other times that I’ve done this, I’ve really wanted edit things as I’m reading it, it feels clunky or like, no, that’s not how I want to say that. But I made a few little wording adjustments as I was reading, but generally speaking, I think the writing is quite good.  

Rob Walling:
Yeah, I’m the same. Every audiobook I’ve ever read, I have made edits to the manuscript as I’ve been making it because there’s just certain things that you find are clunky or I believe in the very read through the SaaS playbook, there was one sentence where it was missing the word not, and so I said the exact opposite. It was probably something like, you should definitely do B2C or something like that, and I was like, what has to be not, I cannot print this book. People think it’s an April Fool’s joke. So anyways, thanks for joining me on the show. Folks want to learn more about the book, where do they go?  

Dr. Sherry Walling:
Exit strategy book.com.com.  

Rob Walling:
See you next time.  

Dr. Sherry Walling:
Peace.  

Rob Walling:
Thanks to Sherry for joining me on the show today, and thank you for joining me this week in every week. This is Rob Walling signing off from episode 743.