Having been through the acquisition process four times—twice as a founder and twice as a startup executive—here’s my list of when (and if) to sell. Don’t take it literally.

Most startups never get a single good acquisition offer, ever.

So logic says, take the best good offer you get. It may be your last.

But we are founders. We aren’t always wired that way. It’s not why most of us do it, at least not once we have something.

So just to spur some thinking, my list of When a Startup Should Get Acquired:

1. Before You Fail / Run Out of Money / Etc.

   If you are slightly hot but with few revenues, or have something but not enough, sell while you still have time. Don’t wait until you have 30 days of cash left. Way too many startups wait too long in this scenario. It’s essentially impossible to sell your startup for any real money when you are out of money.

2. When the Team Isn’t Good Enough.

   Even if you are growing nicely and cash‑flow positive, and all the quantitative metrics look good… if the team isn’t good enough and can’t fix itself—sell if and when you can. Bad teams kill startups every day. Sell before then if you can’t fix it. Sometimes great individuals just don’t make great teams, and it can’t be fixed. It’s sad, but not uncommon.

3. When the Economics, to Everyone, Exceed Your Magic Number.

   I don’t know what your Magic Number is. But you will. It may be $1 billion. It may be $1 million. For Slack, it was $27 billion. The Magic Number isn’t rational, really, and can’t be 100 % explained on a spreadsheet. It is something that makes it all feel right. Sometimes there is no Magic Number, which is great, too. Sometimes you’ll never sell. But often, there is a magic number.

Image: A Twitter poll asks the question, “If you sold your company, would you sell it again?” The results are 59.5 % yes, 40.5 % no.

OK, that’s the easy part. The more interesting part is When Not to Sell. My Learnings:

1. Usually – Do Not Sell If You Are At Scale and Have a Great, Committed Team.

   In SaaS, if you are at $10 M+ ARR, growing nicely, and the team is killing it—just don’t sell. You don’t have to listen to me, but once you are at scale you can’t be killed easily. Why sell? You’ll keep adding value every year. Be honest about the team, and if you’re up for continuing to recruit and building an even better one.

2. Do Not Sell Just Because of the Competition, Unless They Are Truly Decelerating You and You Can’t Stop Them.

   There is always competition. Google threatens to kill you if you don’t sell? Whatever. They can’t kill you if you are growing. A hot startup nipping at your heels? That’s the way it should be. As long as you can hit your plan, it doesn’t really matter.

3. Do Not Sell Because You Are Tired—Or at Least, Try to Fix This First.

   This is the dirty “secret” of M&A. Many successful startups get acquired out of nowhere—despite traction, great customers, etc.—because the founders are exhausted after a long grind (the “5‑Year Walk of Death”). You get so tired after four years, stumble through the fifth, and then take an offer. Don’t let it happen. Bring in fresh blood, fresh capital, whatever it takes. I know of a top‑tier VC fund that specifically targets exhausted founders after five years, making crappy offers with a lot of secondary liquidity because they know it’s a weak moment.

You only get so many at‑bats.

Money is good. Take it. It gives you options and makes you braver, maybe, next time.

But even if you can go do another startup… you can only do so many. If you have something real, something good, something self‑sustaining, something unkillable—hard as that is—you’ve done something magical. You brought something real into the world. Probably, don’t sell.

And remember, if you do sell… it’s not yours anymore. That’s not good or bad; it just is.