Buying over building? The rise of entrepreneurship through acquisition

I remember thinking when I was younger—why would I ever want to work for a small business in my hometown when I could join a tier 1 consulting firm and solve complex problems across the globe, or land at a high-flying tech company and ride the equity rocket to early retirement?

Flash forward to today, and what many talented people “Bucked” is now one of the fastest growing trends.  

The shift we’re seeing across our customers, candidates, and talent circles? The rise of entrepreneurship through acquisition.

Just this week, here’s who I’ve spoken with:

• A former beverage entrepreneur who just secured real backing to roll up laundromats
• The #2 exec at one of the fastest-growing tech unicorns (2020–2024), now building a holding company of “boring businesses”
• Three freshly minted MBAs (Booth, Kellogg) turning down McKinsey, Bain, and BCG offers to launch search funds
• A seasoned vertical SaaS operator looking for their first acquisition
• Two execs who’ve already ridden at least one tech IPO, now funding a talent pool to buy mid-market companies
• A good friend — 100+ startup investments deep — who just bought a gelatin manufacturer

Not really—once you unpack the economics.

A Stanford study showed that MBAs participating in search funds saw average pre-tax IRRs of 35.3% and 5.2x ROI on aggregate.

Put that next to the return profile of the best venture firms targeting 3x returns (25–35% IRR) or the S&P’s 10-year return of 11.3% (excluding dividends), and the math starts to tell a compelling story.

Why the Shift? A Few Key Drivers:

1. PE Has Laid the Blueprint

   Founders of PE firms have quietly made a killing in the last 10–20 years buying and scaling middle-market companies. Shore Capital, for example, has grown to over $9B AUM in just ~15 years deploying this exact strategy. They’ve shown what’s possible—and talent is watching.

2. “Get Rich Quick” Media is Everywhere

   You can’t open a feed without someone claiming they made 7 figures through a side hustle or a business acquisition. That narrative is reshaping ambition. Today’s top talent wants uncapped upside, autonomy, and ownership—not just prestige.

3. The Boomers Are Handing Over the Keys

   Roughly 10 million Boomer-owned businesses will transition over the next 20 years, representing nearly $10 trillion in assets. That’s a generational opportunity. And it’s colliding with a wave of talent ready to buy, operate, and grow.

4. Roll-Ups Are Softer and Sexier Now

   Consolidation used to mean ruthless cost-cutting and soulless finance games. Not anymore. Companies like Lyra Technology (the largest MSP roll-up globally) are showing owners there’s a better exit—one that feels like legacy, not loss.

5. AI Makes Streamlining Easy

   Modern operators are bringing AI-powered workflows into traditional businesses and unlocking value on day one. The cost savings are real, and they hit the bottom line fast.

6. Multiple Arbitrage Is Real

   Buy a business at 3–8x EBITDA, layer in modern tech, improve operations, and you’ve got a shot at expanding margins and re-rating the multiple. That kind of arbitrage—once reserved for software—is now up for grabs in Main Street America.

Bottom line

The best talent isn’t always chasing brand names anymore. 

They’re finding smarter ways to deploy their time, capital, and energy—on their own terms. Autonomy, upside, and ownership are the new currency. And the wave is just getting started.

As you think about your next move, remember, you have more options than you might think… If you’re interested in this strategy give me a shout and I’ll try and set you up with a few friends who deploy it well or are backing world class talent.

Personally - I’d buy a roofing company if I wasn't trying to change the talent game right now… Love a great cedar shake roof!