How I Bought 7 Businesses and Built a $34M Holding Company | Doug Lepisto Interview

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Operator-first, place-based PE done right. In this episode, Doug Lepisto (co-founder of Sleeping Giant Capital) breaks down how his team backed 7 searchers to buy 7 local companies, deploying a $34M Fund I and gearing up for Fund II.

We unpack the full playbook—how they source in-region deals, why they bet on the operator first, and the exact 10-10-10 searcher economics.

Doug shares how they structure boards, protect the downside, and build long-term, hold-forever companies with a university-powered talent pipeline.

Timestamps:
00:00 Intro (Sleeping Giant overview: place-based, West MI, Fund I $34M)
00:33 Doug’s background
04:41 Sleeping Giant timeline
06:18 Sponsor (CapitalPad.com)
10:32 Buffett, Brent Beshore, ETA/search, university model
13:42 Fundraising journey (easiest no, institutions vs HNW/FOs, strategy)
16:13 Ideal targets (shift to higher-quality $3 to $5M EBITDA businesses)
18:14 First acquisition setup
18:20 Sponsor (SpacebarStudios.co)
19:29 First acquisition story
21:41 Deal size (larger than initial target)
22:05 Seller rollover & post-close roles (case by case)
23:14 Operating lessons (protect downside, boards, emotions; big deal are better than many small)
26:25 Pipeline & selectivity (LOIs as the key KPI)
28:48 Operators-first vs deal-first (why back people)
30:32 The 8-week Acquire Course (1:1 coaching format)
34:56 Course throughput & outcomes
35:57 Searcher economics (10/10/10 vesting, salary/bonus)
37:58 Portfolio update & headwinds (tariffs, organic growth systems, board design)
40:27 Fund II focus (double down on place, build an enduring machine)
42:10 Defining long-term (25-year term, durable niches like metal components)
43:38 Liquidity in a long fund
46:04 Scalability (2–3 CEOs at a time; replication in other regions)
47:29 Place-based investing philosophy & macro trends
50:51 Quickfire (best advice and favorite book)

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