Would you sell your startup today for $30M?
Every Monday at Techstars Boston, inside a cramped glass-walled room at the Cambridge Innovation Center, we had a ritual: Each CEO faced the same question.
“Would you sell your startup today for $30M?”
(This is us, bright-eyed on day one of Techstars Boston Accelerator 2013. Look at those baby faces.)
It sounds absurd when you’re sleep-deprived, pre-product-market fit, and surrounded by founders convinced they’ll build the next unicorn. But it’s not hypothetical. This room of founders has since seen everything from complete wipeouts to wild billion-dollar exits.
So what happened in our Monday meeting?
Week 1: 3 out of 14 CEOs said they would sell their company right now for $30M. 11 of 14 CEOs said no.
Week 14, the last week of the program: It flipped. 11 out of 14 CEOs said they would sell their company right that moment for $30M. Only 3 of 14 CEOs said no.
Let that sink in.
Same companies. Same founders. Just 90 days and a little reality check later.
Why?
Building is brutal. Every “win” reveals a bigger mountain ahead. Unicorn visions fade through a gauntlet of customer churn, poor decisions, indecisions, and fundraising woes.
I won’t reveal who said yes and who said no the the $30M question, but our class had a who’s who of incredible founders:
Nikita Bier built and sold two companies: tbh to Facebook and Gas to Discord.
TJ and Elliot sold PillPack to Amazon for $1B.
Jay and Mark’s valuation at Synack was recently $500M.
You won’t find a perfect roadmap here, just one truth: Startups get harder, not easier. You just get better at solving problems.