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The Toughest Sell: A Founder's Guide to Startup Exits by Derek Yan
English | February 21, 2026 | ASIN: B0GPJMBM6X | 203 pages | EPUB | 0.36 Mb
Near the end of 2021, my cofounder and I decided that it was the right time to sell our venture-backed Silicon Valley tech startup. We had six unsolicited acquirers simultaneously reaching out to buy our company. We had raised $13.5 million. Partnerships with the largest Android makers in the world. Over five million monthly users. A great revenue stream. We were so confident it would be a slam dunk that we hired bankers to run a competitive process.
It was not a slam dunk. It was more like the longest shot ever attempted.
After talking to over a hundred potential acquirers and rounds of due diligence, we got exactly one offer after nine months. All stock, from a struggling private company that mainly wanted our cash.
Along the way, we told our employees we were exploring a sale. Every 1-on-1 stopped being about product and became an M&A update. Everyone was now on the rollercoaster of M&A. We had to pivot the company, deal with layoffs and voluntary attrition, and recover from an almost impossible situation. I stopped sleeping. I nearly quit.
It took nearly four years. We made every mistake in this book before we finally closed a deal with a buyer who wanted us for the right reasons.
Across 53 chapters, The Toughest Sell covers every stage of the M&A process as I lived it firsthand.
Some of the lessons it took me four years to learn:
Bankers can amplify interest that already exists. They cannot create interest when there is none. Don't hire them until you have a deal worth negotiating.
Never give a number first. Whatever number you quote will be the ceiling, not the floor.
Don't tell your employees the company is for sale. We did. It nearly destroyed us from the inside.
Term sheets are non-binding for the buyer and binding for you. The power dynamic is never in your favor once you sign.
Valuation is based on emotion, not math. Your best leverage is your ability to walk away from the deal.
Inbound M&A inquiries cannot be engineered. We ghosted a $40 billion company and spent years regretting it.
Starting a business is like launching a rocket into space. Selling it is like landing that rocket back on its pad. If you're a founder going through this, this book was written for you.
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