HoldCo Builders How I Bought 30+ Businesses and Built a $195M HoldCo in My 30s | Chris Sparling Interview
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May 29, 2025 Chris Sparling, Co-Founder and Vice Chairman of Tiny, shares his journey of acquiring over 30 internet businesses. He discusses pivotal early lessons in capital allocation and the advantages of buying established companies versus starting new ventures. Chris also reflects on unique Canadian business advantages and the complexities of deal structuring. His insights from interactions with industry titans like Charlie Munger emphasize mentorship's role. This conversation is a treasure trove for aspiring entrepreneurs and investors looking for practical strategies.
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Early Investing Lessons From Dad
- Chris Sparling learned investing young by hanging out while his dad traded and later investing with him.
- That early exposure and people-pleasing shaped Chris's interest in capital allocation and finance.
First Day With Andrew
- Chris describes his first day working with Andrew: waiting on a street corner, an awkward basement suite, and uncertainty about keeping his bank job.
- That scramble marked the start of their long partnership and Tiny's origin story.
Analog Thought Experiments Guide Strategy
- Thought experiments helped Chris and Andrew reframe digital businesses as analog firms to reveal capital allocation dilemmas.
- That led them to become serial entrepreneurs and eventually prefer buying proven businesses over constant founding pivots.
