45 years → 15 lessons → Millions in mistakes

Most birthday reflections focus on what you've learned. I'm more interested in what those lessons cost me.

The expensive insights that required tuition payments in time, money, relationships, or all three. The mental models I had to earn the hard way because I was too stubborn (or too systematic) to take anyone else's word for it.

These aren't borrowed from books or Instagram quotes. They're the frameworks that actually changed how I operate—in business, relationships, and life.

Some might seem counterintuitive. Others might challenge conventional wisdom. All of them were expensive to learn.

Here's what 45 years of building taught me:

1. The ultimate form of commitment is the elimination of all other options.

There's no more obvious example of this to me than picking up and moving our family to Baja. For years, I dabbled in various side hustles—blogs, projects, low-commitment partnerships—under the idea that optionality is good.

But none of them went anywhere, and it's because I wasn't fully committed to any of them. I hedged, kept my options open, and when things got difficult, I fell back to homeostasis.

It wasn't until my wife and I made the bold decision to uproot the family, leave my corporate track and the C-Suite behind, and start from scratch on a remote Mexican beach that I made shit work. Why? Because I had to. When I hit a rough patch or roadblock, I had no choice but to figure it out.

Looking back, I can say with absolute certainty I wouldn't have stuck it out if I'd kept my options open. I would've distributed my time, diluted my attention, been distracted, and turned back to the easier options I had at the time.

Whether or not I'm willing to burn the boats is a test I apply to determine how committed I am to something. Half-commitment is expensive—it costs you time, energy, and results. When I finally eliminated my escape routes, my focus sharpened and my results multiplied.

2. Don't confuse confidence with competence.

When I transitioned from the corporate track and C-Suite to remote consulting, there was a lot I didn't know. So I did what I do anytime I'm stuck: looked around for help. I hired coaches, consultants, joined masterminds and programs, and invested well over $200k in advice.

Here's what this taught me: the amount of confidence, number of followers, and popularity of content is not correlated to real expertise or experience. Some of the worst "online business" advice I got came from the person who offered the most definitive, absolute, and confident-sounding advice.

By most accounts, they had experience where I didn't, had a big following online and sounded like they knew what they were talking about. I took advice that set me back months, if not years.

Later that program got exposed as a dumpster fire of a business online, but I still managed to squeeze a huge ROI out of my investment by internalizing this lesson: Posturing, popularity, and presentation style makes a message more believable, but it doesn't make it accurate. So pay careful attention to discern between the two.

The most expensive hires, partnerships, and decisions I've made were based on confidence rather than competence. Now I look for proof, not performance.

3. If you start anything assuming it'll be hard, everything is easier.

Six years ago, when I started my consulting business, I was starry-eyed and optimistic. I figured I'd land a couple of high-end clients, work 20 hours a week, and drink margaritas the rest of the time.

What I learned was that you can find a couple of clients that way, but it doesn't make for a very good business. To build something real as a one-person business operating entirely online and remotely required learning how to define my target market differently, position myself in a crowded digital space, package and deliver services remotely, promote myself online, write proposals that sold without face-to-face meetings, and connect all the technology pieces to make it work.

Frankly, it was way harder than I ever expected. But I discovered it was exactly as hard as it needed to be—my expectations were the problem, not the actual events.

So when I launched MSP Sales Partners this past January, I was very deliberate about setting expectations that it was going to be hard. There were going to be challenges, unknowns, and issues to deal with—even with the head start of the prior six years.

While the launch has gone incredibly well, there have been a series of challenges that aren't problems only because I expected them to be problems on the front end. If you temper your optimism and simply expect it's going to be a pain in the ass, the experience of getting there will be far easier—and your probability of actually finishing is a hell of a lot higher.

4. If someone you knew consistently broke promises to you, you'd lose trust in them. The same thing happens when you break promises to yourself.

When I was younger, I let myself go. I was smoking a pack of cigarettes a day, overweight, and in the worst health I'd ever been. I'd constantly tell myself I was going to change things—quit smoking, eat better, start working out. And I consistently broke those promises to myself.

Over time, I quit trusting anything I told myself I would do, which is the rational response to somebody who constantly lies to you. What I didn't realize was that I was in a cycle that compounds for better or for worse: the more promises you break, the less you believe your own goals, the less committed you are to achieving them, the less likely you are to achieve them, the less you trust yourself the next time you set a goal.

I eventually hit a turning point and got my shit together. Started with small changes in how I ate, then bigger changes, then light exercise, which eventually transitioned into racing triathlons and what I still maintain today—a seven-day-a-week workout regimen.

What I've come to learn is that making and keeping promises to ourselves, no matter how small, allows us to build trust in ourselves. We start to actually believe when we set a goal that we're going to achieve it, which motivates us to take action. Recognizing that breaking that promise is going to erode trust keeps us committed to the goal, which ensures we hit it, which builds trust for next time.

Sometimes to turn things around, we just need to make and keep a couple of small promises and build on those.

5. Getting used to feeling like a beginner is the single easiest way to become an expert.

Building businesses in both corporate and entrepreneurship taught me that building a business is just a series of learning how to solve the next problem. And the skills required to solve the last problem aren't necessarily related to the skills needed for the next one.

You may need to hire an integrator—but learning to hire a good integrator is a skill. You may have a constraint on delivery and need to systematize or productize that process. You may need to move to a new marketing channel or medium. Solving any of these problems is a skill in and of itself.

It's easy to get stuck in the "I've got plenty of experience" trap. I see it a lot with experienced founders or people with strong track records in a particular domain—allowing that track record to create an unwillingness to admit that while you're an expert in one area, in this particular challenge, you're not.

Having the humility to acknowledge that and commit to learning how to solve it requires starting over as a beginner, over and over again. But if you pretend you know everything, you never really learn the skill, because admitting you don't know is required to learn the actual thing.

The moment you're comfortable being the worst person in the room, you unlock exponential learning. Ego is expensive—it keeps you from asking the questions that would save you years.

6. You can only truly optimize for one variable at a time.

Trying to optimize for multiple variables has been the single biggest source of frustration and stagnation in my business life.

Early in consulting, I swung back and forth between trying to maximize sales in the short run versus scalability in the long run. The challenge was that the easiest and most expensive things to sell were not only the most difficult things to scale—they were the most demanding to deliver. Maximizing for sales in the short run was actually the worst way to transition to a more scalable business model in the long run.

More recently, I've experienced the same thing with MSP Sales Partners as we determined whether to prioritize growth or product improvements. 5 years ago, I would've said, "Let's do both." But having tried that over and over again, I know trying to do both means doing neither particularly well.

We've made a deliberate decision to prioritize product improvements and limit growth to only the amount needed to facilitate that. It goes against every fiber of my being to slow sales down, but sometimes you have to slow down to speed up.

Pick one variable, win at it, then move to the next. The moment you try to optimize for everything simultaneously, you optimize for nothing—and create unnecessary frustration in the process.

7. We're like torpedoes en route to a target—we hit the end goal through a series of micro failures and course corrections.

This is actually a concept I read in Maxwell Maltz's book Psycho-Cybernetics, where he explains that a torpedo is almost never technically on track. It has a final destination in mind and corrects its course each time it goes off course, which is most of the time. So it hits its target one corrective measure at a time. One mistake at a time.

Building my business from Baja was the perfect example of this torpedo navigation in action. I had to fail my way through internet providers, office spaces, service offerings, marketing strategies, technology platforms, and more to operate the way we do today. But each failure got me a little closer to where I wanted to be.

Which underscores a really important concept: the person most likely to build the best of anything—career, product, business—is the one most likely to get started, make mistakes, learn from them, and iterate their way to success.

Action leads to insight more than insight leads to action. And obsessing over it "being good enough" is the number one cause of it never truly becoming good enough. Because the only way to achieve perfection is through a series of making and correcting a lot of mistakes.

This reframe changed everything. Instead of seeing setbacks as failures, I started seeing them as navigation data. Every "miss" was just information telling me how to adjust my aim.

8. Learning how to earn more is a more valuable skill than developing the discipline to save.

Early in my executive career, I had an aggressive profit number to hit with a lot of money on the line in my annual bonus. We were coming down to the wire and I had a choice to make: start cutting expenses, or sell more.

I went all in on more sales in what everyone who was part of this will remember as the infamous "Q4 Blitz." Not only did I not cut expenses, I increased them. I raised commissions and added a temporary staff role to help.

The result? We set a record that quarter, hit our target, earned our bonuses, and found a couple of strategies we kept for years as new sources of revenue—strategies that accounted for seven figures in new revenue over the next several years.

This experience revealed something crucial: when you're focused on what you can save, you're operating with a fixed pool of money. When you're focused on growth and earning more, the sky is the limit.

I've found the same thought process to be helpful personally as well as in business. It's not that keeping what you earn isn't important—it most certainly is. But while developing fiscal discipline is valuable, the skill of learning how to earn more trumps it. You can only save from what you earn, and if you can figure out how to earn 10x more, it'll automatically result in saving more. That doesn't work the other way around.

9. The most dangerous salesperson is one armed with deep conviction for what they're selling.

If you want to guarantee your next sales hire is going to be a rockstar, hire someone who passionately cares about the market you sell to, the work you do, or how you do it. Someone with a sense of conviction—in the customer, the problem they have, the product you sell, the process you use, or something along those lines—is going to bring a level of commitment you can't train.

They'll work harder, challenge prospects more, and overcome objections better because they truly believe the customer needs to buy what you sell. Their work ethic, body language, and tonality will be stronger than anything you can train.

This is why I succeeded as well as I did at the U.S. Chamber for as long as I did. I cared about the mission, and I hired people who did, too. But no matter what you sell, even if it feels like a commodity, you can find people who bring more to the table than technical skills. Even if it's a passion for sales or having personal experience with the problem you solve.

Tap into that conviction, and you'll tap into more growth. Technique can be taught. Scripts can be memorized. But genuine conviction? That's what transforms conversations and closes deals that shouldn't close.

10. Hard decisions now, easy life later.

Experience has shown me that avoiding discomfort in the short-run guarantees discomfort over the long run.

I can avoid the pain of a 30-minute run I don't want to do, but I have to live with the nagging feeling every day of being overweight and not doing something about it.

I can avoid firing a well-liked employee who's underperforming, but I'll endure daily subpar performance that affects the entire business.

When you optimize for short-term comfort, you ironically create perpetual long-term pain. It creates what I call "avoidance debt"—where avoiding temporary, more intense discomfort adds up and compounds, beginning to affect other aspects of your life and business.

Worse, it eats at you internally because consciously or unconsciously, you know you're avoiding these things out of fear. It eats away at your confidence while also leading to suboptimal performance, which only increases your frustration.

But on the other side of hard decisions is an easy life. The difficult conversation that clears the air. The workout that builds strength and confidence. The business decision that eliminates ongoing problems.

Make the hard decisions now so you can live easy later. The alternative is making easy decisions now and living hard forever.

11. Most people's "failures" occurred on the road to success. They just gave up too early.

A couple of years ago, I had significant traction in my sales audits and fractional work, earning multiple five figures for audits and retainers with revenue share that accounted for over $50,000 a month. But I couldn't scale that offering—or so I thought.

It would always require my execution, and that felt like I'd just built another job. So I pivoted into teaching people how to do what I had done. While I had great success there, it was clear I had to work a lot harder for less money.

I had an epiphany while working with a new adviser: it wasn't that the audits or fractional work couldn't be scaled. It was that I didn't know how to do it. The answer wasn't pivoting away from what I was doing—the answer was leaning further into it, doing more of it, so I could figure out how to scale it, instead of assuming I would stumble across something that was already "scalable."

Since pivoting back into my sweet spot, we've gained product-market fit and significant traction on a new and scalable offering, and we continue to systematize the audits, making them both more efficient to deliver and more effective for the customer.

The takeaway? I simply quit too early. I took the resistance and interpreted it as a wall. I've seen this pattern in coaching more than 200 founders over the past couple of years. More often than not, we're on the right path—we just haven't gone far enough or aren't going fast enough. But trying to start a new path isn't necessarily the answer.

12. Winners will find a way to win. The easiest way to predict whether someone will succeed is to look at their track record.

After coaching more than 200 founders over the past couple of years and observing the people who had the most success, I became convinced that as a coach I wasn't necessarily changing outcomes as much as I was changing timelines. I was helping them hit their targets faster.

Looking at everybody who hit huge milestones—their first million-dollar year, their first sales process without running calls themselves, their first inbound lead generation system working—they all had a track record of figuring it out and finding a way to win before we ever met. These were people who already had a stellar track record throughout their life and career. I have no doubt everyone who was winning was going to win anyway—I just helped them do it faster.

I've found the same thing to be true in my own life. I've gone through different seasons from politics to private equity to remote consulting to true entrepreneurship, and when I go into something new, I never doubt whether I'm going to find a way to make it work. I know that if someone else has figured it out, I can too. It's just a matter of the amount of work I'm willing to invest and the intensity I'm willing to bring—the outcome isn't going to change.

So when I'm looking for people to join my team, people to partner with, or even who my next case study is likely to be, their track record is a pretty true indication of what you can expect from them in the future.

I learned to bet on patterns, not potential. People who consistently find ways to win will find ways to win for you too.

13. Run towards pain if you want to accelerate the growth of yourself and your business at the fastest rate possible.

We are hardwired to avoid pain, but pain is actually a great indicator of a source of growth. Almost every time something is consistently painful for me—like figuring out how to scale an offer, finding a way to simplify our tech stack, or learning how to finally hire the right person into a role after repeated failures—it was an indication of an area I needed to grow, something I needed to develop as a person or businessman.

Rewiring how we think about pain—thinking about it as a source of muscle growth rather than something to be avoided, and looking at it as something to run towards instead of away from—really facilitates the fastest growth.

Because whether you want to tackle that challenge or not is irrelevant. It needs to be tackled. The question is: are you going to endure the pain of getting through it to get to the next level?

The things I avoided because they were hard were exactly the things that would have fast-tracked my success. Comfort is expensive—it costs you growth.

14. Starting a business from scratch will reveal more about your weaknesses and limitations than a decade on the couch with a psychologist.

Nothing has stretched me like entrepreneurship. It's the most aggressive form of self-development I've ever experienced.

You think you're building a business, but what you're really doing is bumping up against every personal limitation you didn't know you had. Insecurity, imposter syndrome, need for control, communication gaps, mindset blocks—all exposed and amplified under pressure.

For example, I'd never considered myself a people pleaser, but I remember staring at my calendar one day, completely booked with calls that were eating into family time while revenue stayed flat. I realized I was saying "yes" to things that weren't moving my business forward because I wanted to please others at the expense of my own priorities. That wasn't a tactical problem—it was a personal one.

Over and over again, I've found that every time I hit a ceiling in the business, I was hitting a ceiling in me. Because starting at zero means you'll have to figure a lot of things out on your own in the early phases. None of us started with a fluent understanding of marketing, sales, operations, human resources, or administration. Learning these things—or even learning how to hire people who already know them—is all a matter of developing new skills and identifying our limitations and weaknesses, then putting in the work to shore them up.

Your business can only grow as fast as you do. Entrepreneurship is the most expensive form of personal development you can buy. But it's also the most effective.

15. Few decisions will have a greater impact on your potential than who you choose to be your partner, where you choose to live, and who you choose to surround yourself with.

Before I started my executive MBA program at SMU, they called all the spouses and partners into a meeting of their own. They explained what the expectations would be over the next two years—because everyone in the program was already a senior manager or executive with responsibilities, and adding the MBA workload was only going to make things more demanding.

After the meeting, my wife told me there were two spouses in tears because they weren't clear on what they had signed up for. But SMU knew something I would only learn with experience: if your spouse or partner is supportive, it's a superpower. If not, they're an anchor.

In my case, there's no question where my wife falls. I've had her support leaving a high-paying, steady role for a risky private equity turnaround. She had confidence I would figure it out when we moved to Mexico and started over. And as I've built my business over the last several years, I've had the luxury of focus, concentration, and flexibility to work as hard as I need to make things work. That's why my wife is a superpower.

I've found my environment to be an amplifier in much the same way. The people around me either help me expand my horizons, raise my game, and make me a better person and businessperson—or they're holding me back.

Who you pick to be your spouse and where you pick to call home are some of the most highly leveraged decisions you can make for personal and business growth. Environment is everything. These choices create the context for every other decision in your life.