Most leadership advice sounds good on a slide deck. It falls apart the first time you have to make payroll with a negative bank balance, fire someone you care about, or walk into a room where everyone has already decided you are going to fail.

I have been in all three of those rooms. Multiple times.

Over the past two decades, I have founded, scaled, and led businesses through every kind of pressure imaginable. I took a startup from zero to $15 million in revenue. I helped grow another company to $35 million with 180 employees. I ran for Congress. I spoke at the Democratic National Convention. And today, as Regional General Manager at Great Day Improvements, I am turning around four underperforming markets across the Upper Midwest.

None of it was smooth. All of it taught me something about what leadership actually looks like when the pressure is real.

This page is the hub for everything I have learned, written, and spoken about on the topic of leading under pressure. If you are a leader facing tough decisions, a team navigating uncertainty, or an event planner looking for a speaker who has actually lived this stuff, you are in the right place.

1. Founding a Company at 24 and What It Cost Me

In 2002, I founded Penebaker Enterprises, a commercial roofing and sheet metal company in Milwaukee. I was 24 years old. I had experience in the trades, some early sales wins at Metal-Era where I grew a $350,000 product line to $1.5 million in a single year, and enough confidence to believe I could build something on my own.

What I did not have was a playbook for what happens when you are the one signing the checks.

The first year was brutal. I was selling, estimating, managing crews, handling permits, chasing receivables, and doing my own bookkeeping. There were weeks where making payroll meant I did not pay myself. There were months where a single delayed payment from a general contractor threatened to shut us down.

But the pressure taught me something that no business book covers: the difference between managing and leading. Managing is keeping the trains running. Leading is deciding which trains to build when you do not have enough track.

I wrote more about these early lessons in The 5 Leadership Lessons I Wish Someone Told Me at 25.

2. Scaling to $15 Million: The Real Story

Over the next nine years, Penebaker Enterprises grew from a one-person operation to a $15 million company with 50 employees. From the outside, that sounds like a clean growth curve. From the inside, it was a series of near-death experiences.

Scaling a construction business means every dollar of growth adds complexity. More crews means more trucks, more insurance, more workers’ comp claims, more scheduling conflicts, more personality conflicts, more opportunities for things to go sideways on a roof in January in Wisconsin.

The pressure points that nearly broke us were not the ones I expected. It was not competition or material costs. It was the internal stuff. Hiring the wrong project manager and losing three clients before I caught it. A foreman who was skimming materials. A key employee leaving and taking institutional knowledge with him.

Every one of those moments forced a leadership decision under pressure. And every one taught me the same lesson: the speed at which you diagnose a problem and act on it determines whether it is a setback or a catastrophe.

I go deeper into the specific scaling challenges in What Building a $35M Operation Taught Me About Leadership.

3. Leading Through Crisis: Lessons From the Worst Moments

After Penebaker Enterprises, I co-founded Roofed Right America. We grew it to over $35 million in revenue with 180 employees. It was the biggest thing I had ever built.

It was also where I learned the hardest lessons about leadership under pressure. Not from growth, but from conflict. A partnership dispute that made the business nearly ungovernable. Decision-making paralyzed by disagreements that should have been resolved early. And ultimately, my departure from a company I had poured years into building.

Here is what I took from that experience:

First, alignment beats talent. You can have the most talented people in the room, but if you are not aligned on values and direction, talent becomes a weapon that fires in every direction. I have seen billion-dollar ideas collapse because two leaders could not agree on the next quarter.

Second, the moment you stop being honest about problems is the moment they become permanent. In high-pressure environments, there is an instinct to paper over cracks. To tell yourself that a people problem will resolve itself. It will not. Problems that are not named out loud get baked into the culture.

Third, leaving is sometimes the highest-integrity move. Walking away from something you built is not failure. Sometimes it is the clearest signal that you understand what you will and will not tolerate.

I explored how these personal crises changed my leadership approach in What 36 Years of Silence Taught Me About Vulnerability in Leadership.

4. The Turnaround: Rebuilding Broken Teams

In December 2025, I took the role of Regional General Manager at Great Day Improvements, overseeing four markets: Chicago, Madison, Milwaukee, and Minneapolis. The region had problems. Falsified records. Staff resignations. Quality issues that had eroded customer trust. Previous leadership had left a mess that was actively getting worse.

Walking into a turnaround is different from building something from scratch. When you start a company, people join because they believe in the vision. When you inherit a broken operation, the people who are left are either survivors, skeptics, or somewhere in between.

My approach was simple but not easy: show up, be direct, and fix the things people can see. Do not start with grand strategy. Start with the broken window in the office, the unpaid vendor invoice, the customer complaint that has been sitting in someone’s inbox for three weeks. Small wins build trust. Trust buys you the credibility to make the bigger changes.

The pressure in a turnaround is different. You are not just leading, you are re-establishing the idea that leadership can be trusted. Every promise you make is measured against every broken promise your predecessor made. There is no grace period. You earn credibility in inches.

This turnaround experience informs a lot of my speaking on resilient leadership and team building. If you are dealing with a similar situation, book a conversation and I will tell you what I wish someone had told me on day one.

5. My Framework for Pressure-Tested Leadership

After two decades of leading through high-pressure situations, I have distilled what works into five principles. These are not theoretical. Every one of them was forged in a moment where getting it wrong had real consequences.

6. Speaking on Leadership Under Pressure

Leadership under pressure is one of my most requested speaking topics. I deliver keynotes and breakout sessions for corporate events, industry conferences, and leadership retreats. Audiences hear concrete stories from building $15M and $35M businesses, not abstract frameworks.

Typical formats include:

• Keynote (45-60 minutes): The full journey from startup founder to turnaround leader, with actionable principles for every level of the organization
• Breakout session (30-45 minutes): Focused deep-dive on one of the five principles, with Q&A and real-time application to your team’s challenges
• Panel or fireside chat: Candid conversation about the hard parts of leadership that do not make it into the company newsletter

See my full speaking topics and availability, or go straight to booking a conversation.

7. Related Articles

I write regularly about leadership, pressure, and the real experiences behind the lessons. Here is the full collection:

8. Frequently Asked Questions

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