Seven years after Slow wrote its first check, Sam sits down with Teamshares CEO Mike Brown as the company prepares to go public. Mike’s core insight is simple: America has millions of durable, cash-flowing small businesses, but no great long-term owner. After buying and operating electrical contractors himself, he realized the opportunity wasn’t another marketplace or PE roll-up, it was building a permanent holding company that acquires great businesses, gives employees ownership, and never sells. Today, Teamshares owns 92 businesses generating roughly $60M in EBITDA. The conversation explores why most roll-ups fail, why capital allocation is the true operating system of the business, and why the traditional private equity model may be running out of steam. Mike closes with an ambitious goal: grow corporate EBITDA from $19M to $100M by 2027 and create a forever home for thousands of small businesses.

Chapters

00:00 Episode Teaser Featuring Mike Brown, Teamshares CEO

01:11 The Teamshares Origin Story

04:48 From Wall Street to Buying Small Businesses

10:47 Why Going Direct to Sellers Didn’t Work (The FSBO Problem)

13:18 Buying at Scale, The Teamshares Model

15:27 92 Acquisitions and $60M EBITDA, Lessons Learned

18:26 Why Generalist Hires Didn’t Work

19:08 Building a Leadership Pipeline

23:46 The Internal YC, Community Across Portfolio Companies

27:42 How Technology Powers 92 Businesses

28:08 “Will This Business Exist in 50 Years?”

32:21 Why Most Roll-Ups Fail

37:30 The Road to $100M EBITDA

39:51 The Long-Term Vision

40:58 Capital Allocation as a Competitive Advantage

42:34 Decentralized Leadership, Centralized Capital

46:16 Why Private Equity Fails Small Businesses

49:25 Going Public, What Comes Next

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Important Disclosures and Disclaimers:Teamshares has entered into a definitive agreement for a business combination with Live Oak Crest Acquisition Corp. (“Live Oak”), a special purpose acquisition company. In connection with the proposed transaction, a registration statement on Form S-4 (the “Registration Statement”) has been filed with, and been declared effective by, the U.S. Securities and Exchange Commission (the “SEC”). This podcast does not constitute an offer to sell or the solicitation of an offer to buy any securities. For important information about the proposed transaction, including where to find the Registration Statement and other legal disclaimers, please refer to the press release available at https://www.businesswire.com/news/home/20260527344175/en/Teamshares-Announces-S-4-Effectiveness-in-Anticipation-of-Nasdaq-Listing.Clarifications:

Teamshares currently has 93 operating subsidiaries. Additionally, Teamshares has had documented revenue declines and business closures. A full reconciliation of non-GAAP measures to the most directly comparable GAAP measures, as well as Teamshares’ audited GAAP financial statements, is available in the Registration Statement. Investors should review the full set of assumptions and risk factors accompanying these metrics in the Registration Statement.