Dear SaaStr: When Should I Sell My Startup?
Selling your company is one of the hardest decisions you’ll face as a founder. It’s not just about the money—although that’s a lot of it.
It’s about timing, momentum, and your long-term vision. And commitment.
1. Don’t Sell Too Early if You’re Growing Fast
A lesson so many founders have learned the hard way. If you’ve hit initial scale (say $1M–$2M ARR) and growth is accelerating, probably don’t sell unless the deal is very attractive. B2B revenue compounds, and once you’ve got momentum, it’s incredibly hard to kill a B2B business unless you mess it up yourself. If you’re growing 150%+ year-over-year with strong retention at this stage, you’re likely sitting on something much bigger than you realize.
2. But … Maybe Sell When You’ve Hit a Local Maximum
Sometimes, you’ll hit a point where you know you can’t grow much faster without significant changes—like raising a ton of capital, entering a new market, or building a new product. If you’re not ready to take those risks or can’t recruit the team to execute, it might be time to sell. But be honest with yourself: is this a temporary plateau, or are you truly stuck?
3. Good Offers Are Rare—Don’t Assume You’ll Get Another
A strong acquisition offer doesn’t come along every day. If someone’s offering you 10x the capital you’ve raised, or a life-changing amount of money, you should seriously consider it. But don’t sell just because you’re tired or burned out—those emotions can cloud your judgment. If you’re still growing and have happy customers, think twice before walking away.
You can see here below in our deep dive with Brian Halligan, Chair and co-founder of HubSpot, that they never got a great M&A offer. Never.
4. Think About Your Next Move
Selling your company isn’t just about the money—it’s about what you want to do next. Are you really ready to start over? Do you have another idea you’re dying to pursue? Or do you want to double down and see how far you can take this one? Remember, you only get so many shots on goal as a founder. Make sure you’re making the decision for the right reasons.
5. The Market Really, Rerallu Matters
Timing your exit with market conditions is key. If multiples are high and buyers are active, it’s a good time to sell. If the market is down, you might want to hold on and wait for a better environment—assuming you have the runway to do so.
When SaaStr Fund-backed Salesloft sold to Vista for $2.3 Billion cash at the very end of the 2021 boom, the investors were divided on when to sell. Half didn’t want to. But founder Kyle Porter knew this was the peak valuation in the space. He was right. The very next week, valuations crashed. And they haven’t recovered since.
Finally, my learnings here summarized: if your gut says sell, talk to your co-founders and think on it. But probably sell. If you gut says No Way, push on. It’s probably right.
And if you are in the middle? You probably should sell. And you probably will also regret it after at the same time. It just is what it is.
