Dear SaaStr: I Just Sold My Business for $130M. Should I Stick Around?

Dear SaaStr: I just sold my business for $130M, and now I’m debating whether or not to stick around. 

First off, congrats on the $130M exit—that’s a huge milestone. Selling a business is a massive achievement, but deciding whether to stay or leave post-acquisition is a deeply personal and strategic choice.

I’ve been there myself twice, including after selling EchoSign to Adobe, so let me break it down for you.

But if I had to summarize it all into one piece of advice, it would be this: Play Another Card. 

If you aren’t sure if you want to stay post-acquisition, that’s OK.  Maybe it’s time to move on, even if you leave a lot of money behind.  But stay one more quarter.  Try one more time.  That way, when you go, it won’t be out emotion, or confusion, or frustration.  And you won’t have any regrets.

Pros of Staying

1. You Can Ensure Your Vision Lives On — To Some Extent
   If you’re passionate about the product and the team, staying allows you to guide its future. Acquirers often have their own priorities, and without you, the product could drift from what you envisioned. Staying gives you a chance to protect what you’ve built and ensure it thrives in its new home.

2. Learn From the Acquirer — Yes, It’s Possible 🙂 
   Working within a larger organization can be an incredible learning experience. At Adobe, I got to see how a $10B+ ARR business operates at scale, and that knowledge was invaluable for understanding at least how so many BigCos really work when they buy B2B products — and when they buy start-ups. If you’re thinking about starting another company someday, this can be a great way to level up.

3. Financial Upside
   If part of your deal includes earn-outs, stock, or performance bonuses, staying could mean a significant financial upside. Walking away too soon might leave money on the table.  You may not care at the time.  But I find most founders care later when they walked away from big retention packages.

4. Stability and Resources
   After years of grinding as a founder, staying in a larger organization can feel like a break — to some extent.  Not totally, but to some extent. You’ll have more resources, less stress, and the world won’t all be on your shoulders —something most founders aren’t used to.  Your results will be more “best efforts” based than hit the plan or die.

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Cons of Staying

1. You’re Not the Boss Anymore
   This is the hardest part. Once you sell, it’s not your company anymore. Decisions will be made that you don’t agree with, and you’ll have less control. For many founders, this is frustrating and demotivating. Ben Chestnut of Mailchimp famously said he knew he’d be irrelevant the moment he sold, and that’s something to think about.

2. Cultural Misalignment
   Big companies move slower, have more bureaucracy, and often don’t share the same scrappy, entrepreneurial culture you’re used to. If you’re not ready for that shift, it can be a tough adjustment.

3. You Might Be Ready for the Next Thing
   If you’re already thinking about your next startup or venture, staying might feel like you’re delaying the inevitable. Many founders find it hard to stay motivated once the thrill of building something from scratch is gone.

4. Burnout
   If you’re burned out from the journey, staying might not be the best move. Even in a less stressful role, you might find it hard to re-engage if your heart isn’t in it.

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How to Decide

Ask yourself these questions:

• Are you still passionate about the product and team? If yes, staying might make sense. If not, it’s probably time to move on.
• What’s the financial upside of staying? If there’s significant money tied to your continued involvement, weigh that carefully.
• What’s your next move? If you already have a clear vision for your next venture, leaving sooner might be the right call. But if you’re unsure, staying for a year or two can give you time to figure it out while learning and earning.

When I sold EchoSign, I stayed at Adobe for a while, but if I’d had a more supportive boss, I would have stayed longer.  Probably I should have, looking back.  It was a mixed bag—I learned a ton and helped grow the business, but I also missed the autonomy of running my own company.

If you’re still undecided, consider committing to a short-term plan—say, 12-18 months—and reevaluate from there. That way, you can see how things play out without feeling locked in.

Play one more card, at least, before you go.  Too many make an emotional decision.  Which is understandable.