Your Company Culture is Toxic Because You Hate Yourself (And Other Fun Truths from a Recovering Lawyer)

Guess what!? I know what you're thinking. "Karl, I clicked on this because I need help scaling my healthtech/medtech/SaaS company, not because I need therapy."

Plot twist: They're the same thing.

Last week I sat down with Chris Kenny—a recovering lawyer (his words, not mine) turned executive coach who's spent 35 years helping successful people figure out why they're still miserable despite having all the things.

And holy shaet, did we get into it.

The Three Questions You're Avoiding

Chris works with the kinds of leaders who have everything checked off their list. The McMansion. The Tesla. The kids in college. The board seat. The exit strategy. They're not worried about making payroll—they're worried about why they wake up every morning feeling like a fraud.

Sound familiar? Yeah, I thought so.

Chris boils it down to three deceptively simple questions:

1. Am I living authentically? (Translation: Am I actually being myself, or am I just playing CEO dress-up?)

2. Am I cultivating meaningful relationships? (Translation: Do people actually like me, or do they just like my budget approval?)

3. Am I making the world a little better? (Translation: Would I be proud of this at my funeral?)

Now, before you roll your eyes and mutter "woo-woo bullshaet" under your breath, stay with me.

Why Your Leadership Team Keeps Quitting (Hint: It's You)

Here's the thing nobody wants to say out loud: If you're walking around feeling like an imposter, pretending to be someone you're not, that anger and resentment doesn't just live in your head. It radiates. It cascades. It infects everything.

Your direct reports feel it. Your customers sense it. Your significant other definitely knows it.

Chris sees it all the time with the owners of privately held companies. The leader sets the tone for the entire culture. If you're miserable, congrats—everyone else gets to be miserable too. It's like secondhand smoke, but for emotional dysfunction.

The good news? The inverse is also true. When leaders start actually giving a shaet about these three questions—when they start taking daily, incremental actions to live more authentically, build real relationships, and make a positive impact—life gets better for everyone in their orbit.

The Most Important Relationship You're Ignoring

We talk a lot about customer relationships, employee relationships, stakeholder relationships. H2H, baby. Human to human.

But Chris dropped this truth bomb that made me sit up: The most critical relationship you're neglecting is the one with yourself.

You can't build authentic connections with your team if you don't have one with yourself. You can't create a healthy culture if your internal culture is a dumpster fire. You can't lead others if you won't lead yourself.

And here's the kicker—most leaders avoid this work because it's uncomfortable. It requires being brutally honest about your shortcomings. It means acknowledging that maybe you're the problem. It's easier to blame the market, the competition, the economy, the latest algorithm change.

But guess what? You have complete control over this. Not your churn rate. Not your CAC. Not your runway. This? This you can actually fix.

Redefining Success (Because Your Current Definition Sucks)

Chris asked me to consider this: What if success isn't just another $100K on the bottom line? What if success is building a company that reflects the best of who you are? A company where everyone who interacts with it—employees, customers, partners—has a better shot at answering "yes" to those three questions?

Mind. Blown.

This isn't about ignoring the X's and O's. You still need revenue. Profit matters. The business has to work. But what if we expanded our definition of "working"?

What if we designed our companies to not only serve the market and hit our numbers, but also to help every human involved live more authentically, build meaningful relationships, and make the world a little better?

That's not woo-woo. That's competitive advantage in a market where everyone's burned out, nobody trusts anyone, and good people are leaving in droves.

The Ripple Effect of Not Being a Hot Mess

Here's what happens when leaders do this work:

They show up differently. They treat people better. They make decisions from a place of alignment rather than anxiety. Their teams actually want to come to work. Retention improves. Customer relationships deepen. The culture transforms.

And suddenly, all those "soft" metrics start moving the hard ones. Because shocker—humans perform better when they're not drowning in toxicity and inauthenticity.

The Daily Practice (For Those Who Actually Want to Change)

Chris's approach isn't some one-and-done workshop. Every single day, you ask yourself:

• What actions can I take today to live more authentically?

• How can I make my relationships more meaningful today?

• How can I make the world a little better today?

Small steps. Incremental progress. Building the habit muscle. And then one day you realize you're excited to go to work. You're proud of what you've built. You don't feel like a fraud anymore.

That's when you know it's working.

Why This Actually Matters for Your Business

I know, I know. You came here for growth strategies and customer retention tactics. But here's the truth: If you're trying to scale a company while being fundamentally misaligned with who you are, you're building on quicksand.

The leaders who win in this chaotic, disruptive market aren't just the ones with the best tech or the biggest funding rounds. They're the ones who've done the internal work. The ones who can build authentic human connections. The ones who create cultures where people thrive.

Want to reduce churn? Start with your own internal churn. Want better stakeholder relationships? Start with the stakeholder in the mirror. Want a company culture that doesn't suck? Start with your own.

It's not complicated. It's just hard. And most people won't do it.

Which means there's a massive opportunity for those who will.

Watch the Full Episode

This is barely scratching the surface of my conversation with Chris. We went deep on what it means to operate as a "conscious leader," how to navigate the discomfort of self-reflection, and why this work is especially critical for founders and owners of privately held companies.

If you're a leader in B2B healthtech, medtech, or SaaS and you're tired of feeling like something's missing despite all your success, you need to watch this episode. Chris has a way of cutting through the bullshaet and getting to what actually matters.

[Link to full episode]

Because at the end of the day, no matter if your business is B2B or B2C, it's really H2H. Human to human.

And that includes the human leading the charge.

P.S. Chris mentioned his most challenging client is his wife Debbie. Which honestly checks out. The people closest to us always hold up the biggest mirrors. Also, he has a 150-pound dog named Max. I didn't ask if Max helps with the executive coaching, but I'm assuming yes.

Karl Pontau hosts The Human Connection Podcast, where we talk about the stuff that actually matters in business: the humans running it. Because whether you're B2B or B2C, it's really H2H, human to human. Subscribe so you don't miss the next episode where we probably say something that'll make your HR department uncomfortable.