I had CEOs at two SaaStr Fund portfolio companies turn down M&A offers last year.
Both offers would have made them nine figures. Personally.
Let me say that again: $100m+ each as founders. The kind of money that means generational wealth. Never work again. Every material problem solved forever.
They both said no. Both have founded epic start-ups, but in many ways, it’s still early.
Here’s What I Told Them Both — Seriously Consider It. No Regrets.
I told them to seriously consider the deals.
Not because I didn’t believe in them. Not because I thought they should sell. But because I’ve seen too many founders carry regret like a weight around their necks for the rest of their careers.
The founder who sold too early and watched the acquirer 10x the business. The founder who didn’t sell and watched it all crater two years later. Both of them still thinking about it a decade on.
No Regrets, my friends. No Regrets.
That was my only advice. Whatever you decide, make sure you can live with it. Make sure you’ve pressure-tested it from every angle. Make sure your family is aligned. Make sure you’ve really sat with the alternative future.
And then decide.
They Both Said Thank You, But No
And here’s the thing — I would have been equally proud of them either way.
Taking a nine-figure exit isn’t weakness. It’s not “giving up.” For most founders, it’s the rational, life-changing, legacy-securing choice. There’s no shame in it. Zero.
But they both looked at what they were building, looked at where the market was going, looked at the team they’d assembled — and decided they weren’t done.
Not even close.
The Legends Who Said No
These two founders are in rarefied company. Over the years at SaaStr, we’ve had the privilege of hearing some incredible stories from founders who faced the same decision.
Ryan Smith, Qualtrics: $500M → $8B
Ryan told me the story at SaaStr Annual. In 2012, Qualtrics was doing about $50 million in revenue when they turned down a $500 million acquisition offer. The first media interview Ryan ever did was with Julie Bort at Business Insider, who basically said: “Do you know how much money that is? You just turned that down?”
Ryan admits she scared him. He had doubts.
But here’s what he told me about the decision: He got in the car with his wife afterward, and she said, “Ryan, you don’t need a bunch of money and I don’t want you home more.”
That was it. They kept building.
Six years later, SAP acquired Qualtrics for $8 billion — a 16x multiple on that original offer. Ryan now teaches a case study at Stanford about that decision.
Aaron Levie, Box: $600M → $4.4B
Aaron and his three co-founders were in their mid-20s when Citrix came calling with a $600 million offer in 2011. After years of cold-emailing investors and pitching Fortune 500 companies from a garage, the idea of that kind of money was “extremely tempting.”
Aaron describes the decision as “volatile” — months of sleepless nights, freaked out, second-guessing everything. The four founders even went to a hotel in Half Moon Bay for an off-site to debate one question: What do we want to do with our lives?
They realized: if they sold now, they’d probably start another company and eventually end up in the exact same situation. They concluded this was a once-in-a-lifetime moment to build something much bigger.
Box went public in 2015 and is now worth over $4 billion. Aaron, at 40, has been CEO for nearly 20 years.
When Saying Yes Is the Right Call
Not every story is about saying no. Some of the smartest founders I know took the deal — and it was absolutely the right call.
Ben Chestnut, Mailchimp: $12B After 20 Years of Bootstrapping
Ben built Mailchimp for two decades without taking a single dollar of venture capital. No outside investors. Just profits reinvested into growth. By 2021, they were doing $800 million in revenue.
When Intuit came calling with $12 billion — the largest acquisition of a bootstrapped company in history — Ben was ready. He’d been getting informally advised by Intuit co-founder Scott Cook for years. He knew the time was right to take Mailchimp from “Act 1 to Act 2.”
Ben told me: “I wanted Mailchimp to join Intuit so we could create one growth platform for small businesses everywhere.”
That’s not giving up. That’s knowing when you’ve built something that can go further with the right partner.
Kyle Porter, Salesloft: $2.3B — Perfect Timing
Kyle is one of our SaaStr Fund portfolio companies, and his story is a masterclass in knowing when to say yes.
He founded Salesloft in 2011 and went through multiple pivots — from job change alerts to contact scraping to finally cracking sales engagement. A decade of will, determination, and grit.
By late 2021, Salesloft had crossed $100 million in ARR with 50% annual growth. Vista Equity came calling with a deal that valued the company at $2.3 billion — a 23x revenue multiple.
The board was split. Times still seemed good, and they wanted to push on for an IPO and an even bigger exit. But Kyle was 100% clear the timing was Now. It was the right deal in a space about to undergo massive change. He convinced the investors to all say yes. The deal closed on December 23, 2021.
Two weeks later, the market crashed. SaaS multiples compressed by 70-80%. Companies that had been trading at 20x+ suddenly traded at 5x. If Kyle had waited for an IPO or held out for a higher price, the outcome would have been dramatically different. The IPO window slammed shut for the better part of 4 years.
Kyle had zero regrets. He’d built something extraordinary, found the right partner at the right time, and captured generational value for himself, his team, and his investors. He later transitioned to Chairman and eventually moved on to his next chapter.
That’s not luck. That’s a founder who understood the market, understood his leverage, and had the wisdom to recognize when the window was open.
The Cautionary Tale Nobody Talks About
Here’s a story that haunts me.
In one of my very first investments, the founders turned down a $50 million acquisition offer. The company eventually sold for nearly $1 billion — a 20x multiple on that original offer.
Sounds like a triumph, right?
Except the founders made approximately the same amount they would have walking away from that original $50 million deal years earlier. Liquidation preferences stacked up. Later investors got their returns first. The math worked out almost identically.
And here’s the part that really gets me: One of the founders passed away before the exit.
I think about that a lot.
The glamour of pursuing a unicorn exit often masks the brutal reality of what it takes to get there. Sometimes the “smaller” win that puts millions in your pocket today is worth more than the theoretical bigger win years later.
The Beast Mode 2.0 Rule
Here’s what I’ve learned after watching hundreds of these decisions play out:
You have to go into Beast Mode 2.0 to say No to a strong M&A offer. Otherwise, say Yes.
What do I mean by that?
If you turn down a life-changing exit, you can’t go back to operating at 80%. You can’t coast. You can’t “see how things play out.” You just turned down guaranteed generational wealth for the possibility of something bigger.
That demands a different level.
Beast Mode 2.0 means:
- You’re recruiting harder than you ever have
- You’re shipping faster than you ever have
- You’re in the market more than you ever have
- You’re more obsessed with customers than you ever have been
- You wake up every day knowing you left nine figures on the table — and you’re energized by that, not haunted by it
If you can’t commit to that? Take the deal. Seriously. There’s no judgment.
But if you can commit to that — if turning down the money actually makes you more driven, not less — then you might be one of those rare founders who’s built for the long game.
What I’m Seeing Now
Both of these founders tripled down after saying no.
They didn’t take a vacation to “decompress from the process.” They didn’t quietly start exploring other options. They came back to their teams and said: we’re going bigger.
More aggressive hiring plans. More ambitious product roadmaps. More intensity in every customer conversation.
They’re more driven now than before the offers came in.
And man, it’s a thing to behold.
The Framework for Your Own Decision
If you’re ever in this position, here’s how I’d think about it:
Say Yes if:
- The number truly changes your life and your family’s life
- You’re not sure you have another gear
- The market dynamics are shifting against you
- You’re tired in your bones, not just having a hard quarter
- You’d spend the next five years wondering “what if I’d taken it”
- You’re at a Local Maximum — the absolute peak of your leverage
Say No if:
- You genuinely believe you’re just getting started
- The offer makes you angry because you know what this thing is worth
- You have a clear, credible path to something 5-10x bigger
- Your best people would be devastated if you sold
- Turning it down puts fire in your belly, not fear
- Your spouse says “I don’t want you home more” (h/t Ryan Smith)
Neither answer is wrong. But you have to be honest with yourself about which founder you actually are.
Most Of Us Are Lucky To Ever Get One Great M&A Offer
Most of us are lucky to ever get one great M&A offer. Most VCs who have seen it all will quietly tell you to almost always take a good deal — even if they’d prefer their portfolio companies hold out for more.
But every now and then, you meet a founder who looks at a nine-figure number and sees it as a ceiling, not a finish line.
Those founders are rare. And when they say no and then triple down?
That’s when you know you’re watching something special.
No regrets either way. But Beast Mode 2.0 is something to behold.
