21 Hats Podcast Dashboard: A Grand Experiment in Buying and Building Small Businesses
18 snips
Jan 23, 2026 
Michael Brown, co-founder and CEO of TeamShares, runs a company that buys small firms and converts them to employee ownership. He discusses scaling a public holding-company model, why they plan to go public while keeping long-term ownership, lessons from buying 90 businesses, low failure rates and high retention, and how employee ownership and practical AI shape outcomes.
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Early Failures Came From Tiny, Owner-Dependent Deals
- TeamShares' failure rate is very low at about 1.5% per year and failures were concentrated in very small acquisitions.
- Early missteps included trying to run small restaurant roll-ups and owner-dependent contracting companies that had high key-person risk.
Build Real-Time KPIs And Software
- Monitor weekly operating KPIs and react early to slippage instead of waiting months for financial reports.
- Build software and reporting so you get near-real-time visibility rather than a 90-day lag.
Multiple Factors Drive Low Failure Rate
- The low failure rate stems from multiple factors: mission-driven team, conservative underwriting, simple business selection, leadership hiring, and employee retention.
- Employee ownership aligns people with profits while TeamShares absorbs acquisition risk.
