Why “No” in M&A Usually Means “No Forever” | Saa Str AI

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“Time kills deals.” Everyone says it. Few people internalize what it actually means.

On 20VC x Saa Str a little ways back, we were discussing Open AI’s acquisition of TBPN. The outreach happened in January. Fidji was new as head of apps, thought it would elevate Open AI’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 about who was sitting in the chairs at Open AI.

Noah Waisberg picked up on this on Linked In and nailed the framing: “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.”

Saa Str Had Two M&A Offers Fall Apart When the Buyers Themselves Got Acquired

We’ve had acquisition interest in Saa Str over the years. Two of those conversations got serious enough that we were working through terms and structure. In both cases, the deals fell apart for the same reason: the companies making the offers were themselves acquired before we could close.

New parent company comes in. New priorities. New leadership. The executive who wanted to buy Saa Str is now reporting to someone who has no idea what Saa Str is and doesn’t care. The deal isn’t killed because anyone decided it was bad. It’s killed because the person who wanted it done no longer has the authority or the mandate to do it.

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. And in a world where management turnover at tech companies has accelerated dramatically, the shelf life of a “yes” keeps getting shorter.

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

This is the math that founders and M&A targets need to run. 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 budget authority, and the same strategic priorities 12 months from now?

At most tech companies in 2026, that number is somewhere between 5% and 20%.

That’s not because these are bad executives. It’s because everything is changing so fast. AI is reshuffling org charts. Companies are rebooting their management teams (as Open AI 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. Not because the acquirer changes their mind about your company. 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.

This applies to liquidity windows too. When Open AI employees get a tender offer at $820 billion, the alert reader should take it seriously. Not because Open AI is doomed. Because liquidity windows close. And when they close, they might not open again for years.

Rory put it well on the show: “It’s back to the liquidity window comment. When the window opens, take it seriously, because it might not open again for a while.”

The same is true for every deal in B2B. 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.

Move fast. Because in M&A, the guy often just isn’t there next year.

Have a question for Dear Saa Str? Submit it at saastr.ai/ai-mentor.

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Key Takeaways

• AI VC AI Mentor: Digital Jason + Amelia AI Startup Benchmarking

• AI Agent Playbook Free e Books

    e Book: Hiring a Great VP of Sales
    e Book: Raising Capital
    e Book:  The First $1m ARR
  

• University All Posts Podcasts The Top CROs VC Fundraising Top Videos Q&A Best of Saa Str #1 Bestselling Book Search Everything Join the Community

• Free e Books

    e Book: Hiring a Great VP of Sales
    e Book: Raising Capital
    e Book:  The First $1m ARR
  

• AI Annual 2026 Events Overview Sponsors

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