About this Video:

In this episode of The Vision with Execution Show, I had the chance to sit down with Jason Rogers—healthcare growth strategist, exited founder, and someone who’s helped generate over $150 million in revenue across healthcare organizations.

We hadn’t known each other long before recording, but I already felt a deep alignment with him. It probably started when I cold-called his cell phone instead of DM’ing him like everyone else. Old-school still works.

But what made this conversation special wasn’t just healthcare strategy. It was the honesty around what it actually takes to build something meaningful.

From Med Device Sales to Whale Hunting

Jason started his career in med device sales before moving into business development at UC San Diego Health. That perspective—inside a major health system—gave him insights most founders don’t understand.

The biggest one?

Decision-making inside large health systems is slow. Very slow.

If you’re selling into them, plan on a two-year sales cycle. There are layers of stakeholders, shifting leadership, budget resets, compliance hurdles. You don’t “close” health systems—you navigate them.

Jason dropped a line I loved:

“Hunt for the whales—but fish every day.”

Translation: Go after the big enterprise contracts, but don’t build your entire business around one deal that might take 24 months to close. Keep smaller revenue streams flowing while you pursue the whales.

We also talked about pilots—starting small within a massive system. Instead of trying to take over an entire hospital network, win two urgent care centers. Do exceptional work. Scale from there.

Quality first. Then quantity.

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The 5x vs 9x Multiple Conversation

One of my favorite moments in the episode was when I asked:

What makes a $5M EBITDA healthcare company worth 5x versus 9x?

Jason broke it down simply:

• Pure service company? Expect roughly 4–6x.

• Tech-enabled services with proprietary software? Now you’re talking 8–11x.

• Own IP? Recurring scalable tech? That’s where multiples expand.

It’s not just revenue—it’s defensibility and scalability.

If someone has a $3M EBITDA healthcare business and wants to grow or command a higher multiple, Jason’s advice was clear:

You either need capital—or you need whales.

At that stage, you’ve likely solved operational chaos. Now it’s about national accounts, strategic partnerships, or bringing in capital to accelerate growth.

And yes—we also touched on partnerships. Jason thrives in team environments. I loved his sports analogy: some people are tennis players, some are football players. Know which one you are before bringing in partners.

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The Mental Health Conversation Founders Avoid

We ended where things got real.

Jason shared that after exiting his company, he went through massive personal and professional losses. From the outside, everything looked fine. Internally, it wasn’t.

He admitted he used to cringe at the phrase “mental health.” Until he needed help himself.

What struck me most was his honesty: the pressure founders don’t talk about is the sacrifice.

You give a piece of yourself to build something meaningful. And sometimes that piece is your time, your peace, your family stability.

Entrepreneurship isn’t glamorous. It’s not overnight. It’s a 10-year “overnight success.”

Jason now prioritizes protecting his peace—morning quiet time, movement, presence with his family. That rhythm compounds positively, just like revenue does.

As a founder—and as someone who has walked through addiction recovery myself—I resonated deeply with that discipline. Mental health doesn’t maintain itself. It requires intention.

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This episode wasn’t just about EBITDA multiples.

It was about building big things without losing yourself in the process.

And if you’re in healthcare—especially scaling between $1M and $10M EBITDA—this one will hit home.

We’ll definitely be grabbing lunch soon. And I know this conversation is just the beginning.