Matt Strippelhoff: How Do You Turn Crisis into Innovation?

21st Century Entrepreneurship

Matt Strippelhoff, partner and CEO of Red Hawk Technologies, is a seasoned entrepreneur, and we spoke about navigating the emotional and professional storms that come with unexpected setbacks. Matt shared how a single January morning in 2017, during a foggy drive along the Ohio River, became the defining moment of his career:

"I thought I was having a panic attack for the first time in my life."

Within weeks, his top three clients—representing the majority of his company’s revenue—called with devastating news: budget cuts, cancellations, and mergers. Faced with the unthinkable, Matt had to make difficult decisions, including layoffs. However, this turning point paved the way for profound innovation and growth.

Here’s what we learned:

1. Client Concentration Risks: If most of your revenue comes from a handful of clients, your business is on thin ice.
2. Innovation Born from Pain: As Matt puts it, "Until you go through some level of pain and suffering, you may not truly innovate." The crisis forced his team to rethink their approach entirely.
3. Shifting the Software Narrative: Instead of selling software projects as finite solutions, Matt reframed them as long-term assets with ongoing value.
4. The Power of Support Systems: Matt credits the Entrepreneurs Organization for being a lifeline: "Spending time with people who've been through challenges like this before is extremely helpful."

We also discussed how operational constraints can lead to freedom, using Matt's unique "tech innovation workshops" and simple ROI tools designed to guide mid-market companies through key decisions:
"If your purchase decision is based purely on cost, nothing’s worth investing in because all you see is pure cost."

Matt’s story is a powerful reminder that even the darkest moments can lead to exponential growth. If you’ve ever questioned whether you're the right person to lead your company through a crisis, this episode offers both empathy and actionable insights.