13 Acquisitions and Going from Private Equity to Permanent Capital | Chris Rolls of PieLab Capital

Chris Rolls is the founder of PieLAB Capital, a holding company with nine portfolio companies built through 13 acquisitions. After building and selling multiple businesses, Chris entered private equity to learn the investing side of the game. But he eventually became convinced that the traditional PE model forces investors to sell their best businesses too early. That realization led him to build a permanent capital holding company inspired by Berkshire Hathaway, Constellation Software, TransDigm and the Swedish serial acquirers. In this conversation, Chris explains how PieLAB sources deals, why private markets offer advantages over public markets, how he evaluates recurring revenue businesses, lessons from growing Detector Inspector, and the three primary levers he uses to create value after an acquisition. Timestamps: 0:00 From Entrepreneur to Investor 3:03 Trading Operational Help for Private Equity Experience 5:01 Why Chris Abandoned the Traditional PE Model 5:25 Discovering Constellation Software & Serial Acquirers 8:43 Why Private Markets Beat Public Markets 13:05 Building Australia's First Serial Acquirer 14:59 The Challenge of Permanent Capital & Investor Liquidity 16:24 How Detector Inspector Grew Into an Industry Leader 17:08 Why Chris Loves Compliance Businesses 20:41 The Three Levers of Value Creation 23:00 The Pricing Power Playbook 25:27 Using AI to Reduce Costs & Improve Operations 33:03 Why Every HoldCo Needs an AI Champion 41:07 Bolt-On Acquisitions vs Platform Acquisitions 43:38 Building a HoldCo for the Next 30 Years 46:06 Work-Life Balance, Curiosity & Long-Term Success This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.