The Toughest Sell A Founder's Guide to Startup Exits
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Foreword

It was the morning of May 15th, 2024—my mom’s 60th birthday. Instead of being focused on planning a birthday message, all my attention was consumed by a single email I had been anxiously awaiting. After years of careful planning, meetings, and countless sleepless nights, I was expecting an acquisition term sheet from a $40 billion market-cap private company. They had originally wanted to buy my company back in 2021. My cofounder Borui and I made the mistake of ghosting their founders after a positive first meeting. And soon the market soured and although we had strong inbound interests and hired professional bankers to help negotiate deals, the only offer we received was a full stock deal from another struggling startup that wanted all of our company cash and other income producing assets. Nearly three years later, in January 2024, as a last ditch hail mary, we reinitiated contact, this time they were again leaning in, and a term sheet felt imminent.

We had done days worth of product and technology due diligence with our team. Their founders and execs have spoken highly of us throughout the process. They even gave us a valuation range and asked if that aligned with our expectations. It was, even though it was on the lower end of what we had to hope to sell for. They had everything they needed to make an offer. Our last meeting had been perfect, we spent a good chunk of the meeting talking about potential relocation logistics and good spots around their headquarters to settle our families. Our main point person reassured us that the offer was being finalized; we just needed to wait a little longer for him to check-in with another stakeholder. However, in the weeks leading up to May 15th 2024, that reassurance turned to radio silence. Each passing day without news deepened my anxiety, leaving me sleepless for days on end, obsessively checking my phone throughout the night. I even had a dream where I flew 16 hours to their office for a meeting but could not check-in because all of the doors were locked shut.

That morning, after a grueling swim at the YMCA, my Apple Watch buzzed mid through my dead hang on a horizontal bar. I immediately let go to read the message from my watch, my heart racing. As I scanned the email, my heart sank—it was not the definitive yes or no I expected. Instead, it was a vague long-winded email that said they needed more time and more stakeholders needed to be pulled in. In an instant, my hopes shattered. A bunch of things flashed in my mind—our team, our board, and even my family had mentally committed to this deal. Yet now, the stark possibility of winding down our once-promising startup, which had raised over thirteen million dollars and partnered with major industry players, felt brutally real. I stood silently, numb with exhaustion and defeat, asking myself, “What now?”

This moment encapsulates the harsh reality of startup mergers and acquisitions. If you are reading this book, you have likely faced similar pressures, expectations, and emotions. But Let me first say: congratulations. Starting a company and getting to the point of considering an exit places you among a select few who have achieved extraordinary things. However, make no mistake—finding a buyer for your business will be among the most challenging endeavors you'll ever undertake.

Starting a business is akin to launching a rocket into space; successfully selling your company, though, is like safely landing that rocket back on its launch pad—far more challenging and fraught with risk. A single misstep can erase years of effort and sacrifice. When startup founders say that the journeys’ highs are really high, and the lows are really low - this is what they are talking about. Hopefully, this book is your guide to navigating that perilous yet potentially rewarding journey.

There's a well-known saying in the M&A circles: "Companies are bought, not sold." Unlike raising funds, selling your business demands the buyer to be deeply convinced that your company is the missing piece to unlock the next level of growth for their business. The market for acquiring businesses is drastically smaller than that for raising capital or finding customers. Many entrepreneurs mistakenly approach selling their company like pitching investors, yet it is fundamentally different and infinitely more complex.

My cofounder and I tried to sell our company starting near the end of 2021, desperately wishing a book like this existed at the time. We thought our strong market position, financial stability, and numerous inbound inquiries would make our exit straightforward. Instead, it took almost four exhausting years before we finally secured the right buyer. Along the way, I learned that most companies actively seeking a buyer rarely find one, and the skills required to sell a business differ greatly from those required to build one.

Few reliable resources exist to guide founders through the complexities of selling a business. The hard truth is that deliberately engaging in an M&A process often leads to disappointment or failure. However, the experiences and lessons shared in this book can help you avoid common pitfalls and significantly increase your odds of a successful exit.

This book hopes to offer candid guidance, vivid personal anecdotes, and practical strategies based on hard-earned experience. My desire is that the lessons learned from my own rollercoaster journey—filled with anxiety, fear, despair, and ultimately a moderate success—will resonate deeply with you and provide meaningful support.

Your entrepreneurial journey is extraordinary, filled with challenges and achievements few ever experience. I sincerely hope that this book will help you land the outcome that you desire and deserve, let’s begin.

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