The Flywheel of Buying Businesses in a Single Region

September 11, 2025
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W

hen today's guest first tried to raise capital for his fund, "it was the easiest 'no' ever" from investors.

He was literally laughed at.

Doug Lepisto and his partner were raising a fund to build an ETA ecosystem in their local region.

They envisioned working with searchers to buy businesses based in Western Michigan specifically.

The target businesses would be in that area, the searchers would live there, and there would be a close association with Western Michigan University in Kalamazoo, where Doug is a professor.

The core idea was place-based and long-term.

As Doug put it to me, "If Brent Beshore, Warren Buffett, the search fund community, and a university had a baby, that's what we would be."

Flash forward, and Sleeping Giant Capital has done 7 searcher-led acquisitions, and they're raising a second fund, likely to be quite a bit larger than their first $34m fund.

There are many themes here, including:

  • How Sleeping Giant finds, vets, and trains searchers
  • What exactly searchers are signing up for here, and what are the economics
  • The non-concessionary nature of these acquisitions. That is, while it is impact investing, they do expect to generate market returns for themselves and their investors.
  • Could this model be viable in other regions?

And much more. Doug and I go deep on his model.

As you listen, ask yourself if something similar could be built where you are.

Here he is, Doug Lepisto of Sleeping Giant Capital. Enjoy.

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The Flywheel of Buying Businesses in a Single Region

Doug Lepisto has partnered with 7 searchers to acquire businesses strictly in Western Michigan. Momentum is building.

Key Takeaways

Introduction

Listen to the introduction from the host
W

hen today's guest first tried to raise capital for his fund, "it was the easiest 'no' ever" from investors.

He was literally laughed at.

Doug Lepisto and his partner were raising a fund to build an ETA ecosystem in their local region.

They envisioned working with searchers to buy businesses based in Western Michigan specifically.

The target businesses would be in that area, the searchers would live there, and there would be a close association with Western Michigan University in Kalamazoo, where Doug is a professor.

The core idea was place-based and long-term.

As Doug put it to me, "If Brent Beshore, Warren Buffett, the search fund community, and a university had a baby, that's what we would be."

Flash forward, and Sleeping Giant Capital has done 7 searcher-led acquisitions, and they're raising a second fund, likely to be quite a bit larger than their first $34m fund.

There are many themes here, including:

  • How Sleeping Giant finds, vets, and trains searchers
  • What exactly searchers are signing up for here, and what are the economics
  • The non-concessionary nature of these acquisitions. That is, while it is impact investing, they do expect to generate market returns for themselves and their investors.
  • Could this model be viable in other regions?

And much more. Doug and I go deep on his model.

As you listen, ask yourself if something similar could be built where you are.

Here he is, Doug Lepisto of Sleeping Giant Capital. Enjoy.

About

Doug Lepisto

Doug Lepisto
Doug Lepisto

Show Notes

Episode Transcript

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