How I Bought 30+ Businesses and Built a $195M HoldCo in My 30s | Chris Sparling Interview

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 dad
00:00:58 - The pivotal moment meeting Andrew and starting their journey together
00:02:55 - The “law firm” thought experiment and why it shaped their capital allocation mindset
00:04:28 - Realization: Buying proven businesses is better than starting from scratch
00:06:00 - How Chris became a shareholder in Tiny (not a typical path)
00:08:53 - Avoiding bad businesses: wholesale transfer price risk and capital intensity
00:09:25 - Sponsor: Spacebar Studios
00:10:34 - Canadian location arbitrage and headspace advantage
00:12:29 - Sponsor: Space Bar Studios — helping B2B companies scale growth without hiring a full team
00:13:15 - The unfair advantage of Andrew’s online persona
00:17:23 - Why founders choose to sell to Tiny: Speed, authenticity, and respect
00:19:00 - 2-year dry spell in dealmaking and how discipline shaped their approach
00:20:48 - Favorite structuring method: “Bird in hand” vs. “two in the bush”
00:22:51 - How they acquired AeroPress from its legendary inventor
00:25:04 - Fastest deal Tiny ever did—and why it worked
00:27:22 - Buying “venture orphans” at deep discounts
00:29:00 - Organic growth vs. price-driven acquisitions
00:30:44 - How Tiny evaluates moats and pricing power
00:31:58 - Siloing debt and managing risk through asymmetric bets
00:33:36 - Would unlimited capital improve their investing strategy?
00:34:55 - Lessons from Charlie Munger and playing the ultra-long game
00:36:31 - Equity, ego, and how to prevent resentment in partnerships
00:39:40 - The legendary $57,000 charity lunch with Bill Ackman
00:43:13 - Meeting Charlie Munger: nerves, learnings, and shouting questions
00:46:04 - Why advice from mentors can be dangerous
00:49:11 - Chris’s decision-making framework: hell yes or no, relativity, gut instinct
00:52:01 - 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 special
01:01:14 - Why nobody has it all figured out—even the shiny people online

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https://podcasts.apple.com/us/podcast/holdco-builders/id1695713724

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This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.