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 

Show Notes & Links

Connect with Boris on LinkedIn

Boris’ Blog

Curious what your business is worth? Book a free call with me here.

Definitions

Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.

Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.

Roll Over Investor: A rollover investor, in the context of selling a business, refers to an individual or entity that rolls some of their proceeds from the sale with the buyer. This strategy allows the seller to defer capital gains taxes and potentially leverage their expertise or resources in a new venture.

About Our Guest

Boris Berenberg is a New York-based technology entrepreneur, product leader, and startup community builder. He founded and bootstrapped Atlas Authority, scaling it to a global team of 15 and thousands of customers before successfully exiting through an acquisition. With over a decade of experience in the Atlassian ecosystem, Boris has worked with major organizations including Spotify, Uber, and Zenefits. He’s currently the CEO of z0.ai, where he helps customers deploy AI agents to support non-technical users.