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Why Most Startups Fail—and What Real Entrepreneurs Do Next

Entrepreneurship Simplified

Release Date: 04/16/2025

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Entrepreneurship Simplified

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So here’s the thing...

Most people talk about entrepreneurship like it’s this glamorous, straight shot to success. But if you’ve ever actually started something, you know it’s more like a rollercoaster with no seatbelt. 

In this episode, I sat down with my friend Doug Milbauer, who’s been through it all: 11 startups, multiple industries, wins, losses, pivots, and plenty of “What was I thinking?” moments. 

Doug shares how he went from dropping out of college to jumping into real estate in Austin during a boom, then starting businesses in places he didn’t even fully understand yet. Some of them took off. Others? Crashed hard. We talk about what happens when a business looks good on paper but completely falls apart in real life. And more importantly, what you do next. 

We hit on some real stuff here. Like why educating the market is so expensive (and risky), how most people aren’t actually willing to do the work, and why you should not compete on price unless you own the whole supply chain. Doug also opens up about the times he should’ve walked away sooner, but didn’t, and the cost of holding on too long.

If you’ve ever felt the sting of a failed idea or the pressure of making your business work because your identity is wrapped up in it, you’ll feel this one. This conversation isn’t just for entrepreneurs, it’s for anyone who’s ever taken a big risk, fallen flat, and had to ask, “Now what?”

💥 What happens when the dream doesn’t work

📉 Learning to say “no-go” before wasting time and money

💡 Ideas are great, but only if people actually want them

🚫 Stop giving CPR to dead business ideas

EPISODE HIGHLIGHTS:

00:00 - Introduction

00:58 - Doug’s background and entrepreneurial experience

02:45 - Starting, scaling, and losing two businesses

06:47 - "How hard could it be?” – Starting a construction company

09:04 - Hitting the jackpot: The dream business model

10:36 - Reflections on emotional and financial resilience as serial entrepreneurs

15:36 - The risks of spending your whole runway teaching customers they have a problem

20:58 - Why product-based startups, especially without funding, are incredibly risky

24:13 - Doug and Keith share personal experiences of clinging too long to a failing idea

26:40 - How entrepreneurs can detach their self-worth from their ventures

27:52 - Doug’s biggest lesson in entrepreneurship

ABOUT OUR GUEST:

Doug Milbauer is the Director of the Coastal Bend Business Innovation Center and an Assistant Professional Professor at Texas A&M University–Corpus Christi. With over 35 years of experience in entrepreneurship, sales, marketing, and management, he has founded ten startups across various industries and led two intrapreneurial ventures, including one with a NYSE-traded company. Milbauer holds a BBA in Marketing from the University of Texas at Austin and both an MBA and an MS in Entrepreneurship and Organizational Behavior from the University of Texas at Dallas. He is currently pursuing a PhD in Entrepreneurship. Before joining TAMU-CC, he taught at institutions such as Stephen F. Austin State University, UT Dallas, Texas Christian University, and the University of North Texas. His vision for the CBBIC is to foster entrepreneurship and venture creation among students, faculty, and the Coastal Bend communities.

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If you enjoyed today’s podcast, don’t forget to subscribe, rate, and share the show! There’s more to come, so we hope to have you along with us on this journey!