How I Bought 30+ Businesses and Built a $195M HoldCo in My 30s | Chris Sparling Interview
How I Bought 30+ Businesses and Built a $195M HoldCo in My 30s | Chris Sparling Interview  
Podcast: Buyers and Builders
Published On: Thu May 29 2025
Description: In this episode of HoldCo Builders, I’m joined by Chris Sparling, Co-Founder and Vice Chairman of Tiny. Chris has helped acquire and scale more than 30 internet businesses and has deep insights into capital allocation, due diligence, deal structuring, and the psychology of long-term investing.We talk about how Tiny was built, the story behind acquiring AeroPress, thought experiments that shaped their early decisions, and what Chris learned from personal interactions with Charlie Munger and Bill Ackman. Whether you’re a business buyer, holdco operator, or investor, this episode is packed with timeless wisdom and practical frameworks.Thank you to our newest sponsor:Spacebar Studios: https://www.spacebarstudios.co/In Today’s Episode We Discuss:00:00:00 - Chris's backstory and early investing lessons from his dad00:00:58 - The pivotal moment meeting Andrew and starting their journey together00:02:55 - The “law firm” thought experiment and why it shaped their capital allocation mindset00:04:28 - Realization: Buying proven businesses is better than starting from scratch00:06:00 - How Chris became a shareholder in Tiny (not a typical path)00:08:53 - Avoiding bad businesses: wholesale transfer price risk and capital intensity00:09:25 - Sponsor: Spacebar Studios00:10:34 - Canadian location arbitrage and headspace advantage00:12:29 - Sponsor: Space Bar Studios — helping B2B companies scale growth without hiring a full team00:13:15 - The unfair advantage of Andrew’s online persona00:17:23 - Why founders choose to sell to Tiny: Speed, authenticity, and respect00:19:00 - 2-year dry spell in dealmaking and how discipline shaped their approach00:20:48 - Favorite structuring method: “Bird in hand” vs. “two in the bush”00:22:51 - How they acquired AeroPress from its legendary inventor00:25:04 - Fastest deal Tiny ever did—and why it worked00:27:22 - Buying “venture orphans” at deep discounts00:29:00 - Organic growth vs. price-driven acquisitions00:30:44 - How Tiny evaluates moats and pricing power00:31:58 - Siloing debt and managing risk through asymmetric bets00:33:36 - Would unlimited capital improve their investing strategy?00:34:55 - Lessons from Charlie Munger and playing the ultra-long game00:36:31 - Equity, ego, and how to prevent resentment in partnerships00:39:40 - The legendary $57,000 charity lunch with Bill Ackman00:43:13 - Meeting Charlie Munger: nerves, learnings, and shouting questions00:46:04 - Why advice from mentors can be dangerous00:49:11 - Chris’s decision-making framework: hell yes or no, relativity, gut instinct00:52:01 - A masterclass on incentives (with kid allowance examples!)00:57:29 - Are high-level meetings worth it—or should you just focus on the work?00:59:45 - What makes Bill Ackman special01:01:14 - Why nobody has it all figured out—even the shiny people online----------------------------------------------Subscribe on Spotify:https://open.spotify.com/show/6lr5bE3SNZF2uEE7Nb0DHhSubscribe on Apple Podcasts:https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724Follow Mikk/PrivatEquityGuy on Twitter: https://x.com/PrivatEquityGuy⁠⁠⁠Chris on Twitter: ⁠⁠⁠https://x.com/_Sparling_This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.