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Press resources for Exit Strategy, by Rob & Sherry Walling
About Exit Strategy
Short SUMMARY
SELL THE BUSINESS. STICK THE LANDING. WE’LL SHOW YOU HOW
While many entrepreneurs start companies, only a select few achieve a successful exit.
Dr. Sherry Walling, a clinical psychologist specializing in entrepreneur mental health, and Rob Walling, a serial entrepreneur who has secured life-changing sums in multiple exits, have teamed up to provide you with a roadmap for navigating this treacherous terrain, offering a rare combination of practical savvy and emotional nuance that can only come from a true understanding of the journey.
Exit Strategy will teach you:
Frameworks to Plan Your Exit: Practical steps to prepare you not just for landing your dream deal but for the often overlooked emotional rollercoaster.
Strategies to Protect What Matters: How to safeguard your relationships, mental health, and financial stability to ensure you sell without regrets.
Wisdom from Those Who’ve Done It: Insights and real-life lessons from founders who’ve successfully (AND unsuccessfully) managed their own exits.
Don’t be left wondering ‘what if’. Follow this step-by-step guide, avoid million-dollar mistakes, and set yourself up for thriving in the next phase of your life.
LONG SUMMARY
SELL THE BUSINESS. STICK THE LANDING. WE’LL SHOW YOU HOW
While many entrepreneurs start companies, only a select few achieve a successful exit.
Dr. Sherry Walling, a clinical psychologist specializing in entrepreneur mental health, and Rob Walling, a serial entrepreneur who has secured life-changing sums in multiple exits, have teamed up to provide you with a roadmap for navigating this treacherous terrain, offering a rare combination of practical savvy and emotional nuance that can only come from a true understanding of the journey.
Exit Strategy will teach you:
Frameworks to Plan Your Exit: Practical steps to prepare you not just for landing your dream deal but for the often overlooked emotional rollercoaster.
Strategies to Protect What Matters: How to safeguard your relationships, mental health, and financial stability to ensure you sell without regrets.
Wisdom from Those Who’ve Done It: Insights and real-life lessons from founders who’ve successfully (AND unsuccessfully) managed their own exits.
Don’t be left wondering ‘what if’. Follow this step-by-step guide, avoid million-dollar mistakes, and set yourself up for thriving in the next phase of your life.
This Book is a Must If:
You want to avoid million-dollar mistakes when selling and don’t want to be left wondering, ‘What if’
You’re struggling with the emotional toll of letting go and worried about what comes next.
You want to protect what matters most—your relationships, well-being, and legacy.
Three Pillars for a Successful Exit
Section 1: One of the Hardest Things You Will Ever Do
From confronting the reality of letting go of what you've built to understanding the factors that shape your feelings about selling, this section equips you with the insights to begin your exit journey with clarity and purpose.
Section 2: The Nuts and Bolts of Getting It Right
A deep dive into the mechanics of deal-making, from identifying the right buyer to deal structures and negotiations. It also addresses the importance of having a strong support team and practical strategies to minimize the impact on your mental and physical health.
Section 3: After the Ink Dries
The immediate and long-term opportunities that come with exiting your business. Practical guidance on managing newfound wealth, reinventing personal and professional identities, and nurturing relationships affected by the transition.
About the authors
Short biOS
Rob Walling is a serial entrepreneur who has built six companies (five bootstrapped, one funded). He’s been teaching founders how to build, launch, and grow startups for nearly two decades.
He runs the original community for bootstrapped SaaS founders, MicroConf, and the first bootstrapper-friendly accelerator, TinySeed. He’s the host of the Startups for the Rest of Us podcast and has written four best-selling books about startups.
Dr. Sherry Walling is a clinical psychologist, speaker, award-winning author, and mental health advocate specializing in the unique challenges faced by entrepreneurs.
With a PhD in clinical psychology, Sherry has completed research fellowships at Yale University School of Medicine and the National Center for PTSD. Her books, The Entrepreneur’s Guide to Keeping Your Sh*t Together and Touching Two Worlds, and her ZenFounder podcast, offer deep insights into managing stress, growth, and grief, particularly in the entrepreneurial world.
FULL BIOS
Rob Walling is a serial entrepreneur who has built six companies (five bootstrapped, one funded). He’s been teaching founders how to build, launch, and grow startups for nearly two decades.
He’s written three best-selling books about startups: The SaaS Playbook, Start Small, Stay Small, and The Entrepreneur’s Guide to Keeping Your Sh*t Together, and more than 100 essays about starting startups.
In 2010 he started a podcast with Mike Taber, which became one of the most popular startup podcasts on iTunes, called Startups for the Rest of Us. It has shipped every week since then and now has nearly 750 episodes and 15 million downloads.
In 2011 he cofounded MicroConf, the largest community for non-venture track SaaS founders.
He founded Drip, an email marketing tool that allows a user to send emails to their audience based on user behavior, in 2012. It was acquired in a life-changing exit by Leadpages in July 2016. He led the Drip product team, out of Leadpages’ Minneapolis headquarters, until April 2018.
In October 2018, Walling announced that he was starting the first startup accelerator designed for bootstrappers, called TinySeed.
Walling has become known as a supporter of self-funding or bootstrapping software companies that turn a profit, instead of raising funding from venture capitalists. He has invested in more than 210 companies and has been quoted in dozens of major publications, including The Wall Street Journal, Forbes, Entrepreneur, and Inc. Magazine.
Dr. Sherry Walling is a clinical psychologist, speaker, award-winning author, and mental health advocate specializing in the unique challenges faced by entrepreneurs.
With 30,000+ hours of consulting experience, she has helped thousands of founders and leaders recover from burnout and navigate the hardest moments of their careers. Besides her consulting work, she creates experiences to reconnect with play, joy, and aliveness. These include in-person retreats, group coaching experiences, and the Touching Two Worlds Circus Shows.
She hosts the ZenFounder podcast, which has been called a “must listen” by both Forbes and Entrepreneur Magazine and has been downloaded more than 1,000,000 times. She is also the host of Mind Curious, a podcast exploring psychedelics and innovation in mental health care.
Her best-selling book, The Entrepreneur’s Guide to Keeping Your Sh*t Together, combines the insight and warmth of a therapist with the truth-telling mirth of someone who has been there. Her award-winning memoir Touching Two Worlds explores new strategies for finding wholeness in the aftermath of loss.
Dr. Walling is an expert in trauma, stress, and burnout and her research has been published in academic journals such as the Journal of Traumatic Stress. She is a graduate of the University of California, Davis and Fuller School of Psychology. She has a PhD in clinical psychology and master’s degrees in both psychology and theology and she completed research fellowships at Yale University School of Medicine and the National Center for PTSD in Boston.
Sherry speaks on stages all over the world on topics such as burnout, grief, entrepreneur mental health, and the life-saving value of a good hobby. She also worked as a mentor in several start-up accelerators including Lunar Startups, Beta, and TinySeed.
For press inquiries, please get in touch at rob@startsmall.com and SHERRY@zenfounder.com
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Praise for the work of Rob & Sherry Walling, PhD
I sold my business for $22M but it was as devastating as putting my baby up for adoption. So lonely without guidance. I wish I had this book then. It wonderfully captures the big decision and guides you through it. Buy the book now, too early instead of too late.
— Derek Sivers, Founder, CD Baby | Author of "Anything You Want"
I wish I had this book before I sold my last company. 17 years later, having bought and sold companies of all sizes, I can see that all the insights are exactly right. Not just the useful technical stuff, but the personal emotional stuff. This is the knowledgeable therapist that everyone needs.
— Jason Cohen, Founder, WP Engine
Rob and Sherry, two of the few people I’d take advice from, walk you through the highs, lows, and everything in between with a detailed guide to help you prepare for the big exit. From the emotional rollercoaster to the must-know practical tips, this book is a checklist you'll want by your side before making any moves.
— Sam Parr, Founder, The Hustle (Sold to Hubspot)
Reading Exit Strategy felt like having a candid chat with someone who knows exactly how intense and taxing these transitions can be—and how to make them less painful. The real-life stories from founders mixed with expert advice help navigate not just the nuts and bolts of selling, but also the emotional whirlwind that comes with it. Whether your exit is a long-awaited dream or a sudden necessity, this is your go-to guide for regret-free selling.
— Erik Huberman, Founder and CEO, Hawke Media
Selling your business isn't just about negotiating the terms. I've seen too many entrepreneurs crack under the pressure of not knowing what to do with their post-exit life and their new pile of money. Rob and Sherry Walling don't just show you how to sell your business right—they guide you through what comes next. 'Exit Strategy' helps you understand how to navigate this new stage of your life, ensuring your financial and personal success continues long after the deal is done.
— Jordan Harbinger, Creator, The Jordan Harbinger Show
Dr. Sherry Walling has created a must-read for every entrepreneur with Exit Strategy. This book is the ultimate roadmap for navigating one of the most emotionally complex and financially critical moments of your entrepreneurial journey—selling your business. Dr. Walling digs deep into the emotional struggles we often overlook, from the identity crisis of letting go to the anxiety of entering the unknown. I’ve been there, and let me tell you, the lessons in this book are priceless. Whether you’re just starting to consider an exit or are already deep in the process, this book is your guide to doing it without regret. Exit Strategy empowers you to protect both your heart and your wallet while setting yourself up for your next big adventure—an absolute game-changer.
— JJ Virgin, 4x NYT Bestselling Author, 3x Inc 5000 Founder
As an entrepreneur, your business is more than just a venture—it's a part of who you are. Sherry and Rob Walling understand what it takes to navigate a business exit, tackling the tough decisions and the emotional rollercoaster. Their guidance helps you stay grounded and keep your emotional well-being strong, especially if things become high demand. Let their experience support you.
— Emily Fletcher, Founder, Ziva. Author of the WSJ Best Seller “Stress Less, Accomplish More”
Nailing your exit isn't just about the deal—it's also about not losing yourself in the process. Because what’s the point of a successful exit if you’re too burned out to enjoy it? This book helps you to consider not only the business but also the life you’ll lead after the sale.
— Dan Martell, WSJ bestselling author of “Buy Back Your Time”
Like Bo Burlingham's Finish Big, but more concise and easier to digest. Every maker-turned-entrepreneur should have this book on their nightstand as soon as they hit product/market fit. Even if you're not thinking about an exit yet, this book will prepare you for when that time inevitably comes.
— Giacomo 'Peldi' Guilizzoni, Founder and CEO, Balsamiq
Exit Strategy is a fantastic overview of everything that goes into selling your business. It does a great job of illuminating many of the considerations in the sales process that I only discovered through trial-and-error. The book is one of the best ways to prepare to sell your business.
— Adii Pienaar, 3X Founder (2 exits): Cogsy, Conversio & WooCommerce. Author of “Life Profitability”
Selling your company involves so much more than just the logistics. What are the "right" reasons to sell? And how are you supposed to deal with the crazy psychological ups and downs after the sale closes? This book covers the whole process from daydreaming about selling to what to do with the money. A must-read for anyone thinking about selling.
— Laura Roeder, Founder, Paperbell
I foolishly missed a chance to sell my first company and, many years later, experienced a life-changing exit. I wish I'd had Sherry and Rob's superb collection of advice before both of those events. Founders—please read this book. I promise you'll come out wiser, happier, and very likely wealthier for it.
— Rand Fishkin. CEO of SparkToro and Snackbar Studio. Founder of Moz (sold in 2021)
I’ve supported hundreds of entrepreneurs through hundreds of millions of dollars in business sales, and this is the resource I wish had existed for both them and me when I sold my last business. From evaluating whether it’s the right time to sell, to navigating the complexities of the transaction, and even dealing with the emotional ups and downs that follow, this book feels like having Rob and Sherry by your side as trusted mentors every step of the way. Having been fortunate enough to call Rob and Sherry friends, I am now excited to gift this book to every entrepreneur I meet who is considering an exit, so they can benefit from their deep knowledge and compassion during what can be a life-altering experience.
— Chris Yates. Founder, Rhodium Network
This beautiful and much-needed book demystifies the technical and emotional process of selling your business. Read it before you start and discover a wise, inspired roadmap to improve your business and life outcomes. Your journey as an entrepreneur has been existential. When you exit, you must continue to play “the great game of business” until the last check clears. At the same time, you must process a major loss and start your personal transformation into an unknown future. This book provides the ounce of prevention you require to do both without being damaged, and the applied practical insight you need to succeed. Coaches, consultants, therapists and mentors will want to share this book with clients. Many stakeholders in our shared innovation ecosystem will be grateful to Rob and Sherry for creating this invaluable resource with so much enduring value.
— Michael A. Freeman, M.D., Founder, Econa. Faculty, U.C. Berkeley Psychology
Sherry and Rob Walling have knocked it out of the park with this one. They’ve laid down the blueprint every entrepreneur needs to make a clean, smart exit—no sleepless nights, no regrets. From timing the sale to negotiating like a pro and figuring out what’s next, their insights are gold. This book is your go-to guide for moving on without looking back. Trust me, if you're ready to level up and let go, you need this.
— Joe Mechlinski, New York Times Best Selling Author, CEO of SHIFT
As an entrepreneur, I started, scaled, and exited six of my own companies. I now mentor entrepreneurs on the exit journey, so I understand all too well the high stakes and slim margins for error. 'Exit Strategy' by Sherry and Rob Walling is an essential part of the toolkit for any founder aiming for a great exit, and a brighter future beyond the close. Make this book a go-to resource to avoid the common pitfalls and set yourself up for the successful next phase of your career.
— Mac Lackey, Founder, ExitDNA
No one warns you about the emotional roller coaster that often comes with exiting a business. Sherry and Rob lay it all out, the highs and the gut-wrenching lows. This is a conversation that we need to bring into the light to let others know they’re not facing this alone.
— Mike Brown, Founder, Unbreakable Wealth
Exit Strategy is not just a practical guide, but an emotional lifeline for entrepreneurs facing one of the most challenging decisions of their lives. From the first page, I was captivated by how deeply the insights resonated with some of my own experiences. This book sheds light on the untold emotional journey of selling a business—the doubts, the fears, and the unexpected sense of loss, and all of the tactical parts that accompany it. I wish I had a book like this when I was considering going through the process. It would have given me the clarity and reassurance I needed to navigate the emotional rollercoaster and realize that feeling isolated, uncertain and doubtful is far from uncommon. Sherry and Rob’s guidance makes you feel seen, understood, and prepared—not just for the sale itself, but for the complex emotions that come with it. This is a book that every entrepreneur should have by their side.
— Jessica Aiello, Founder, iYellow Group. Creator, Three Circles