Chapter 9Prepare for the Most Likely Case of No Acceptable Offer

It was near the end of the summer in August 2022 when the last plausible lead finally came back with an offer sheet—and it was a complete non-starter. The terms were so bad that everyone would have been better off if we’d simply returned our cash balance to investors and operated independently indefinitely. Everyone else had already said no.

That day, it finally hit me: we might not sell this company. Not this quarter. Maybe not ever.

It wasn’t a dramatic realization—no shouting, no meltdown—just the slow, heavy feeling of gravity returning after a year spent chasing something that never materialized. For months, I’d been living in deal mode: back-to-back meetings, rehearsed pitches, bankers promising that “next week could be the one.” And now, there was only silence.

If I’m being honest, I thought it was going to be easy. When we first started responding to inbound inquiries in September 2021, we were convinced we’d have a term sheet by Christmas. We had more than five inbound M&A conversations with major industry leaders and roughly twenty additional prospects through banker-led outbound. We were profitable, had strong partnerships, and had even hired bankers to manage the process. Everything pointed to momentum—until it didn’t. Month after month, each promising lead fizzled into a polite “we’ll circle back” or “timing isn’t right.” Instead of building products and delighting users, we spent nearly a year chasing meetings that went nowhere, building custom demos that no one remembered. By the time we realized none of it was going anywhere, the damage was done.

I was reviewing that final term sheet with Borui over Zoom. He stared at the screen in the same quiet daze I felt. “We just wasted a year,” I said. He nodded.

That was the moment I realized what no one tells you about M&A: most exits don’t happen.

For every acquisition headline you see, there are a hundred stories like ours—companies that try, wait, hope, and eventually move on. Finding a buyer isn’t the norm; it’s the outlier. The real work, if you want to survive the process, is preparing for the most likely case: that no acceptable offer will come.

The hardest part was facing the team. We’d been so confident that an exit was imminent that some employees had exercised their stock options early, anticipating a payout. When it became clear that no deal was materializing, we had to make the brutal decision to do another round of layoffs and pivot to an entirely new product. That was one of the lowest points of my career.

It taught me a simple but painful truth: you can’t set deadlines on something you don’t control. Founders love to say things like “we’ll find a buyer by summer” or “we’ll close this quarter.” But M&A doesn’t follow startup timelines—it moves at the pace of bureaucracy. Even when everything goes right, an acquisition requires dozens of internal approvals from finance, legal, product, and engineering teams. Every “yes” spawns three more meetings. Every signature takes weeks. The idea that you can enforce a deadline is a fantasy. When you pressure a buyer with an arbitrary date, you usually end up with one of two outcomes: a rushed, unfavorable offer—or no offer at all. The better approach is to remove the clock entirely. Let the relationship develop organically. The right deal happens when both sides are ready; forcing it rarely ends well.

So what happens when you’ve talked to every potential acquirer, followed every lead, and still can’t find anyone willing to issue a term sheet? There are really only two paths forward: continue building, or wind down gracefully.

If your company is generating positive cash flow, staying independent isn’t the worst outcome. You can buy out your investors with existing cash or future profits, bring in a professional CEO, and reorient the business as a lifestyle company. Once you remove the pressure of hyper-growth, you might find a different kind of freedom—the kind that comes from running a profitable, sustainable business without outside expectations. It’s not glamorous, but it can be deeply rewarding.

One of the most difficult contingencies, however, is trying to go back to business as usual with the same governance structure after a failed M&A. Once you’ve publicly committed to selling, the psychology inside the boardroom changes. If you were pressured to sell by investor board members, it almost becomes a one-way door. Even if you can’t pull off a deal, expectations have been set. The right thing to do in that case is often to provide some form of liquidity for the investors—either through existing company cash, a new fundraising round, or, if none of that’s feasible, by stepping down and letting someone else reset the narrative. Personally, I found it nearly impossible to continue operating under the same board dynamic after failing to deliver an exit when liquidation was what they expected. Once that trust line breaks, continuing on feels like paddling against the current.

If your company isn’t cash-flow positive, the decision gets even harder. You’re burning money, and the runway is shrinking. The question becomes not “can we survive?” but “should we?” Many founders hang on, convinced that a miracle round or last-minute acquirer will save them. Occasionally it happens, but most of the time, the responsible move is to confront reality. Winding down gracefully isn’t failure; it’s leadership. Return any remaining capital to your investors, treat your employees with dignity by offering severance, and help them find their next opportunities. The majority of startups fail. There’s no shame in accepting that. What matters is how you fail—on your own terms, with integrity intact.

It took me years to make peace with that truth. During the process, I kept telling myself that every company that tried long enough would eventually find a buyer. But time isn’t always the cure. Sometimes markets change faster than you can adapt. Sometimes buyers simply stop buying. And sometimes, no matter how well you’ve executed, there’s just no fit. Accepting that reality isn’t defeat—it’s maturity.

The good news is that this clarity gives you control. Once you stop chasing phantom timelines and start planning for contingencies, you can make clear, grounded decisions: how much to invest in the next product cycle, how to communicate with your team, and how to protect your own sanity. Setting “no offer” as your baseline doesn’t mean you’ve given up—it means you’re running the company grounded in reality, not what you wish would happen.

And once you’ve accepted that possibility, only then can you start thinking clearly about what comes next—what the company is truly worth, what you’re willing to walk away for, and how to evaluate an offer if one finally arrives.

That’s where we go next.