Why “No” in M&A Usually Means “No Forever”

“Time kills deals.” Everyone says it. It is especially true in M&A.

On 20VC x SaaStr a little ways back, we were discussing OpenAI’s acquisition of TBPN. The outreach happened in January. Fidji was new as head of apps, thought it would elevate OpenAI’s brand, pitched it internally, and got the green light. It took a few months to close. By the time it did, the entire management team that championed the deal was already changing. The COO moved to special projects. The CMO stepped down. The CRO left. Fidji herself took a leave of absence.

That deal would not happen today. Not because anything changed about TBPN. Because everything changed at OpenAI.

Sometimes the market changes. Sometimes a competitor moves first. Sometimes something breaks inside your company. And sometimes the executive championing the deal leaves, loses influence, or shifts priorities.

SaaStr Itsele Had Two M&A Offers Fall Apart … When the Buyers Themselves Got Acquired

We’ve had acquisition interest in SaaStr itself over the years. Two of those conversations got serious enough that we went through all the meetings. In both cases, the deals fell apart for the same reason: the companies making the offers were themselves acquired.

Deals don’t just die because someone says no. They die because the person who said yes leaves, gets reorged, gets acquired, or simply moves on to the next priority.

The VP Who Wants Your Deal Has a Single-Digit Chance of Both Being There in 12 Months And Having the Same Priorities

When a VP or SVP at a large company champions your acquisition, ask yourself: what are the odds this person is in the same role, with the same authority, and the same strategic priorities 12 months from now?

At most bigntech companies, that number is probably less than 20%.

Companies are rebooting their management teams (as OpenAI just demonstrated). Acquirers themselves are getting acquired. Strategic priorities that made sense in January look completely different by April.

I saw this pattern repeatedly at Adobe too. Every senior executive got a “big chip” (a billion-dollar deal that could move the needle) and a “small chip” (a $50-200 million deal they could pursue without too much scrutiny). The small chip deals were the ones most vulnerable to champion risk. Nobody got fired if the small chip deal didn’t work out. But nobody fought to keep it alive if the champion left, either.

The TBPN deal was a small chip deal. Sam probably spent five minutes on it. “Is this the one you really want to do this year, Fidji? Then just do it.” That’s fine when the champion is there. When they’re not, there’s nobody to push it across the finish line.

The Practical Lesson: Default Yes to Good Deals. At Least as a Framework.

If you’re a founder and you get an attractive acquisition offer, take this seriously:

The deal that’s on the table today may never come back. Because the human being who wants to buy you changes roles, loses budget, gets a new boss, or gets distracted by a different priority.

“Not now” almost always means “not ever” in M&A. The acquirer won’t tell you that. They’ll say “let’s revisit in Q3” or “we love this but the timing isn’t right.” What they mean is: the window is closing and I don’t know if it will reopen.

When someone wants to buy your company, partner with you, or write you a big check, the clock is already ticking. Not on due diligence. On whether the champion who loves you will still be in the chair when the paperwork is ready to sign.

In M&A, the guy often just isn’t there next year.