Revisiting 'Enlightened Entrepreneurship': How I Evolved from Founder to CEO
Lessons Learned A Decade On
Ten years ago, I published Enlightened Entrepreneurship, a book that captured my early experiences in building and scaling a company. At the time, I was in the last year of my 20s—full of energy, ambition, and the relentless drive of a founder. But I was still learning what it meant to be a leader. I had the hustle, but I lacked the patience, discipline, and perspective that only come with time.
Since then, I’ve led multiple organizations, navigated crises, scaled teams, and taught future entrepreneurs what it really takes to build something that lasts. Along the way, I’ve learned that being a CEO isn’t just about vision and execution—it’s about evolving, adapting, and, sometimes, unlearning the very things that made you successful in the first place.
Now, as I approach the end of my 30s, I find myself looking back at the thoughts of my younger self, curious to see how much I’ve changed. What did I get right? What did I miss entirely? And, most importantly, what do I know now that I wish I’d known then?
From Builder to Leader
As a founder, you live in the trenches. You do everything yourself because, in the early days, there’s no one else to do it. The business is an extension of your will, and your sheer force of energy can propel it forward.
But at some point, that stops working.
The company outgrows you. The skill set that made you successful in year one is suddenly inadequate in year five. Your job shifts from “doing” to leading, from executing to empowering. You go from being the scrappy underdog fighting for survival to the leader of an organization that others depend on.
This shift is one of the hardest transitions an entrepreneur faces. Many resist it. Some refuse to make it. They stay in the weeds, micromanage every decision, and burn themselves out. Or worse, they become the bottleneck that holds their company back.
I almost fell into that trap. But through experience (and a few hard lessons), I learned that leadership isn’t about being the best at everything—it’s about building the best team and getting out of their way.
Letting Go of the “Founder’s Ego”
One of the hardest lessons I had to learn was that my instincts—so valuable in the early days—weren’t always right as the company grew.
As a founder, you believe in your vision more than anyone else. You have to. That belief carries you through the rejections, the sleepless nights, and the near disasters. But that same conviction can blind you. You start thinking you have all the answers, that no one can match your intensity or decision-making ability.
The reality? If you’ve hired well, you’re probably not the smartest person in the room. And if you are, you’ve made a serious hiring mistake.
A CEO’s job isn’t to have all the answers—it’s to create the conditions where the best answers emerge from the team. That means listening more than talking, trusting the experts you’ve hired, and making space for dissenting opinions.
The best leaders I’ve studied—Marshall, Eisenhower, even modern business titans—weren’t dictators. They were facilitators of decision-making. They sought out diverse perspectives, welcomed disagreement, and focused on making the right call, not being right.
Decisiveness Over Perfection
One of the greatest shifts I made from founder to CEO was learning to balance careful deliberation with decisive action.
Early on, I obsessed over details, wanting everything to be perfect. But leadership at scale isn’t about perfection—it’s about momentum. A 90% right decision made quickly is almost always better than a 100% right decision made too late.
Great CEOs operate with a bias toward action. They gather enough data to make an informed decision, commit to a course of action, and adjust as needed. They don’t get paralyzed by uncertainty.
At B:Side, I’ve had to make tough calls with incomplete information, whether it was navigating regulatory shifts, structuring partnerships, or reshaping our internal culture. The key is not to fear making the wrong choice—it’s to build an organization that can course-correct when necessary.
The Hardest Skill: Leading Through Others
Perhaps the biggest challenge in evolving from founder to CEO is learning to lead through others.
Early on, I equated leadership with personal effort—if something needed to be done, I did it. If a decision needed to be made, I made it. That worked when the company was small. But as teams grew, that approach became a liability.
True leadership isn’t about doing—it’s about enabling others to do their best work. That means:
Hiring the right people and trusting them.
Creating clear priorities so teams know where to focus.
Holding people accountable without micromanaging.
Providing coaching and feedback that makes them better.
The best CEOs don’t run the company alone. They build leadership teams that can operate independently, freeing them to focus on strategy and long-term vision.
What I’d Tell My Younger Self
If I could go back ten years and give my younger self advice, it would be this:
Let go of control sooner. Your job isn’t to do everything—it’s to build a system that works without you.
Make decisions faster. Perfection is the enemy of progress. Gather data, trust your instincts, and keep moving.
Listen more than you talk. The best leaders ask great questions and create environments where the best ideas win.
Invest in people relentlessly. Your company is only as good as the people you hire, develop, and retain.
Stay humble. No matter how much you think you’ve achieved, there’s always more to learn. Seek out mentors. Read widely. Stay curious.
The Journey Continues
A decade into this journey, I’m still learning. Leadership isn’t a destination—it’s a lifelong process of growth, adaptation, and reflection.
What worked in my first company doesn’t necessarily work in my current one. The lessons I’ve learned today may need to be unlearned in five years. That’s the nature of the job.
But if there’s one thing I know for certain, it’s this: The best CEOs are those who evolve. They shed the habits that no longer serve them, embrace new ways of thinking, and continually refine their approach.
The question isn’t whether you’ll change as a leader—it’s whether you’ll do it intentionally.
And that, more than anything, is what separates those who succeed from those who stagnate.