“Building a holdco was the worst thing I ever did”

Hey folks,

Last March, I hosted a ton of amazing speakers at HoldCo Conference 2025. 

The talks were so great I can’t keep them to myself.

So we’ve put together a miniseries of magazine-style articles we’re calling HoldCo War Stories — and today, I’m sharing the first one.

This is from Walker Deibel’s talk. He’s the founder of Acquisition Lab and author of the classic business book Buy Then Build.

If you were there, you remember Walker’s opening line:

"Building a holdco was the worst thing I ever did."

Let's dig in.

Why Building a Portfolio Almost Killed My Business

From Walker Deibel's talk at HoldCo Conference 2025

"Building a holding company was actually the worst thing I ever did."

Walker Deibel’s confession, especially to a room of acquisition entrepreneurs, cut through the usual conference bravado.

It's not the message most attendees at Holdco Conference 2025 expected from someone who'd become one of the top 2% wealthiest Americans through acquisitions.

But Deibel's brutal honesty about his near-catastrophic mistakes offers hard-won lessons for anyone dreaming of building the "smallest Berkshire Hathaway ever."

The crisis began in 2018 when Deibel's star general manager at his manufacturing company called with devastating news. "Walker, I'm leaving you," the manager said. Within weeks, the dominoes started falling.

"Four weeks later, 40% of my company pulls up in pickup trucks and quits," Deibel recalls. "I'm talking welders. I'm talking salespeople. I'm talking people in the office. Like half the company quits in one day."

The timing couldn't have been worse. His largest customer at the distribution company was running an RFP on 700 products, threatening to leave unless prices dropped. His biggest e-commerce product was under attack. Problems at one company became correlated to his ability to execute at others.

"This is what I call the Swiss cheese model of accident causation," Deibel explains. "Once you start stacking all of these different things, problems at one company become correlated to your ability to execute on a different company."

Deibel had built what he calls a "horizontal holding company" instead of a vertical rollup. His disparate businesses—manufacturing, distribution, marketing, e-commerce—shared nothing. Different customers, suppliers, management teams, locations.

"I had gone out as a light bulb, but I failed at being a laser," he admits.

The result? He failed at everything a holding company is supposed to achieve: diversified risk, scaled operations, multiple cash flow streams. Instead, he was "stacking risk at the same exact time."

After clawing his way back, Deibel distilled his lessons into a conservative playbook that flies in the face of acquisition ambition. Some key principles:

Start with one. "I know you're ambitious. I know you just want to hurry up. Just do one," he insists. Focus obsessively on that first business as your cash flow engine.

Build equity first. "If you're still 90% leveraged and you haven't built up any equity yet, it's too early." His recommendation: spend 5-7 years building strength before expanding.

Pay more for quality. Find a company with minimum $1 million in adjusted EBITDA for your first acquisition. "Pay more for it. Because what you're paying more for is the ability to J-curve through volatility."

Master operations before allocating. "You cannot be CEO of more than one thing at a time. So please slow down."

The most successful companies—Apple, Microsoft, Facebook—spent decades perfecting their core business before major acquisition sprees. Even Berkshire Hathaway, the acquisition gold standard, completed just 52 deals in its lifetime compared to Apple's 100 in six years.

Unable to get more debt, Deibel pioneered what he calls "pizza by the slice" investing—fractional stakes in institutional-grade businesses. "You don't have to buy the whole pizza every time."

This approach eliminated the management burden while maintaining high returns. "I've actually made just as much money doing this style of investing as I have acquiring and running my own businesses."

For operators drowning in the complexity of multiple businesses, it's a sobering alternative to the holdco dream.

Deibel's message rings clear: "Pay attention to what is statistically likely. Just be conservative with how you're approaching it."

In a room full of ambitious acquirers, sometimes the hardest lesson is learning to slow down.

● Focus before you scale. Master one business completely before adding complexity. You can't be CEO of multiple things simultaneously.

● Build equity cushions first. If you're still 90% leveraged, it's too early to expand. Spend 5-7 years building financial strength.

● Pay more for quality deals. A $1M+ EBITDA business can weather volatility. Cheap, small deals stack risk instead of diversifying it.

Liked this?

The next one: How a NYC cab owner's "clever" legal structure backfired spectacularly - and became the precedent courts use to ignore your corporate protections.

Thanks,

Michael

P.S. All the war stories come from HoldCo Conference 2025. 

The stories are great. The live conversations are even better. 

Earlybird pricing for HoldCo Conference 2026 ends Sep 31. Get your ticket today.

_{Editor’s note: Any factual errors or misunderstandings in the article are Girdley Media’s, not the presenter’s.}