Tech Executive Kevin Korte Exposes The Brutal Truths That Make Or Break Entrepreneurial Success

What If Everything You Knew About Leadership Was Wrong?

The host of The Deep Wealth Podcast and post-exit entrepreneur Jeffrey Feldberg speaks with Kevin Korte.

When you think of tech leadership, you probably imagine Silicon Valley, flashy titles, and boardrooms packed with buzzwords. But Kevin Korte doesn’t play that game—and what he shares in this episode will shake the foundation of how you lead and grow your business.

Kevin is a tech executive who operates on his own terms. As a global board member and President of Univention North America, he runs a U.S. company from across the Atlantic, mentors entrepreneurs, champions open-source technology, and challenges centralized tech powerhouses.

This isn’t a talk about trends. It’s a wake-up call about what really makes or breaks success—and why most entrepreneurs are leading in isolation, chasing the wrong metrics, and sabotaging their own companies without realizing it.

The Brutal Isolation of Leadership

“Leadership is lonely,” Kevin says bluntly. “You’re at the top, and no one really gets it. Your friends and family love you, but they’re not in it. Your team? You can’t dump your fear on them. So what do you do? You go silent—and that’s a killer.”

This silence is one of the most dangerous patterns Kevin sees in founders. It's not just about being alone—it's about being stuck. When you can't share the weight of decisions, you stay reactive. You repeat mistakes. And eventually, you burn out.

Kevin’s answer? Mentorship—but not the kind that tells you what to do.

“A great mentor doesn’t make decisions for you. They walk with you. They challenge your thinking. And they ask: what did you learn, and what will you do differently next time?”

The First Time Kevin Had to Fire Someone

It took Kevin six months to fire his first employee—a decision he now knows should have taken one.

“I was terrified. I didn’t want to make the wrong call. But I had the CEO of our group walking with me, not forcing my hand, just supporting me,” he recalls.

That experience shaped his entire leadership philosophy: make the hard calls, but make them from a place of growth, not ego.

Most entrepreneurs wait too long to fire. Not because they don’t know what to do—but because they’re afraid of what it says about them. Kevin exposes this lie and offers a reframing: firing someone might be the first step toward being the leader your company actually needs.

Why Kevin Stepped Off the CEO Track

Kevin could have stayed in the traditional executive lane, climbing the corporate ladder. Instead, he pivoted.

Why? Because his true strength wasn’t in managing teams of teams. It was in strategic thinking, board-level insight, and helping founders make better decisions—especially when the stakes are high.

“One of my top KPIs if I were leading again? Find someone to replace me. Grow them. Make myself obsolete.”

That’s the kind of radical, ego-free leadership that separates great companies from the rest.

How AI Is Changing the Game—and What Founders Get Wrong

Let’s get one thing straight: Kevin doesn’t buy into the AI hype. But he doesn’t ignore it either.

“AI isn’t magic. It’s a tool. If you don’t know the problem you’re solving, AI won’t help you—it’ll distract you,” he warns.

He compares the rise of AI to the dawn of the internet. In the beginning, everyone saw utopia. Then came surveillance, monopolies, and burnout. The lesson?

“Use AI to eliminate busywork—not connection. You can automate scheduling. You can’t automate trust.”

And if you're an entrepreneur who's already feeling behind? Don’t panic. Kevin’s advice is clear: start with a problem, not a tool. Solve something real. Then scale with the help of smart automation.

The Metric That Really Matters (And You Won’t Find It On a P&L)

When Kevin invests in or joins a board, he asks one question:

How many customers are brought in by other customers?

That’s it. Because no matter your revenue, if you’re not creating advocates, you’re building a leaky bucket.

Another metric he swears by? Team morale.

“We love measuring computers. We forget that our greatest resource is human. Do your people believe in the mission? Do they trust leadership? If not, you’ve already lost.”

This approach turns traditional leadership on its head. Instead of obsessing over financial forecasts, Kevin looks for energy, alignment, and momentum. These are the real indicators of scale.

The Red Flags That Make Investors Walk

If you want Kevin’s money or time, you need to show one thing above all else: honesty.

Even a hint of dishonesty will get him to walk. And he's not talking about major fraud, he’s talking about posture, evasion, and the fear-based positioning that many founders unconsciously display.

Another red flag? Lack of strategic thinking.

“I’ll ask for financial projections—not because I believe the numbers, but because I want to see your thought process. Can you think in problems, solutions, and what-ifs? That’s what matters.”

Founders who wing it rarely grow. Those who reflect, model, and iterate? That’s where the magic happens.

The Unspoken Truth About Asking For Help

One of Kevin’s most fascinating insights has nothing to do with tech. It’s about how entrepreneurs ask for help or more often, don’t.

He points out that people who grew up with financial security tend to ask for favors without guilt or over-apologizing. They just ask. Confidently. Directly.

But entrepreneurs who didn’t grow up with wealth often over-explain, bargain, or don’t ask at all.

“If you want to get better at business, practice asking for small favors. Start with friends. Offer value. Build the habit.”

Because in the end, business is about relationships. And if you can’t ask, you can’t scale.

The Future of AI, Leadership, and Human Connection

Looking 5 to 10 years out, Kevin sees massive shifts coming—especially in regulation, digital sovereignty, and the role of global platforms.

But no matter how the tech evolves, one truth remains:

“You can’t replace human relationships. AI can take notes. It can’t care.”

This is why Kevin believes in open source, in digital freedom, and in leadership that prioritizes clarity over control. Entrepreneurs who lean into these truths will build the companies of the future.

Final Thoughts: Kevin’s Advice To His Younger Self

If he could go back, Kevin wouldn’t give himself a business lesson. He’d go back to being 10 years old and say:

“Don’t let teachers—or anyone—demotivate you. They’ll be gone soon.”

That advice holds true for entrepreneurs today. Don’t let doubters, fear, or self-imposed limits derail your mission. Learn from failure. Lead with intention. Surround yourself with people who’ve been there—and build something that matters.

Listen Now And Discover What Actually Works

This is the kind of episode that rewires how you think. If you're tired of surface-level leadership tips and ready for real insight that moves the needle, Kevin Korte delivers.

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Because the difference between surviving and scaling? It's what you know and what you're willing to face.

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