01 May Built to Sell: Why He Regrets Selling for 3.5X EBITDA
Boris Berenberg bootstrapped Atlas Authority, an Atlassian partner that resold Jira and Confluence to mid-market companies and built apps on top of the platform, to high seven figures in revenue with 18% net margins, then sold to private equity in May 2022.
A year later he wrote a blog post titled “I regret selling my startup” that went viral inside the exited founder community. On this episode, you discover how to:
Spot the three buyer buckets that show up in any informal market test
Avoid being valued on trailing twelve months when your business is hockey sticking
Mentally write rolled equity down to zero before you sign
Recognize “dragon mode,” the psychology that turns a windfall into a second job
Run the 30-value stack rank exercise that reframed Boris’s entire regret
Decide between cash flow and wealth before you sell, not after
Consider the option Boris never seriously weighed: hire a CEO instead
