From Startup Failure to “Buy Then Build”, Walker Deibel’s Speech at ACHIEVE Summit

Walker Deibel’s ACHIEVE Summit speech did not disappoint. But he didn’t come selling fantasies. For nearly 57 minutes, the audience listened as he spoke of often unknown truths about the startup path – and why it’s not always as alluring as it seems.

His story starts in the early 2000s during business school. He and his team licensed early 3D tech (years before 3D became mainstream) and built a point-of-purchase advertising concept around it. It was working. They had momentum. They had attention. They even had a massive potential customer — “it rhymes with Walmart,” he said.

Then the month he graduated, the license got pulled.

“And the whole startup went from big momentum to complete failure in a single day,” Deibel told the room.

Basically, the tech owners wanted to go chase Hollywood-level opportunity instead of building with “three MBA students in St. Louis,” as Deibel joked on stage, putting his palms out. Overnight, the business was dead.

So he did what a lot of ambitious people do next. He doubled down. And he tried again.

He built a SaaS company with serious credentials. A proven team. Oversubscribed funding. A top accelerator. A Microsoft executive recruited as CEO. Betas inside “over half a dozen public companies.”

And still, it failed.

“16 months later, we had no paying customers,” he said. “No product market fit. And we were completely out of cash.”

That was the moment his thinking changed.

Deibel realized that startups are often a terrible vehicle for the life people say they want — referring to what usually is income, impact, leadership, and real wealth. The odds are ugly. Even “smart” teams fail all the time. And when they fail, you can waste years building something that never becomes sustainable.

So he asked a better question: if the goal is to build a business that works, why not start with one that already works?

He started noticing something most people overlook: the “boring” businesses were the ones quietly producing cash flow. They already had customers. They already had product-market fit. They already had operations running. They weren’t guessing.

That’s when the “Buy Then Build” idea clicked.

Instead of trying to invent demand, you buy a company that already has it — then you improve it through better leadership, smarter strategy, and modern tools.

Deibel eventually bought his first company in 2006: a book printing business. He ran it for seven years, then sold it. He used that experience and capital to keep going — buying and building across multiple industries, including distribution, manufacturing, and e-commerce.

His message at ACHIEVE was clear. And that was simply that ownership doesn’t have to start from scratch. You don’t need a Silicon Valley-style swing to build something meaningful. In a lot of cases, the fastest path to stability and upside is buying a proven business.

And then, of course, being the person who takes it further.

About the Southland Development Authority

The Southland Development Authority, a not-for-profit economic development organization, is committed to driving equitable and sustainable economic growth in the south suburbs of Chicago. Through innovative programs, strategic partnerships, and impactful direct investments, the SDA is building a vibrant, inclusive economy that drives wealth growth for individuals, businesses and municipalities. Combined with the benefits of the South Suburban Land Bank and the Monarch Fund, the SDA serves as a model for regional development.