Serial entrepreneurs don’t have the luxury of being micromanagers. For new founders, it can be tempting to take an overly hands-on approach; like a parent with a new baby, they can feel as though they need to swoop in for every missed step and hiccup, or else the company might topple over. They install themselves as a central pillar in their venture’s design, making sure to have a chair at every long-term strategy session, short-term project and daily team meeting. In doing so, though, the founders cement themselves up within the business — and cut themselves off from any chance of leaving to pursue other business interests or grow.


Serial entrepreneurs don’t have the time or professional bandwidth to hover over their company and resolve day-to-day concerns. If they tried, the sheer amount of work would inevitably overwhelm them within a few days. Instead, they need to build and staff the company in a way that empowers it to succeed without their direct intervention. This idea might seem intimidating to some new or overprotective founders, especially if they feel as though only they can lead it effectively. But here’s the issue with an “if you want something done right, do it yourself” mentality — it’s based on a faulty assumption that the entrepreneur always knows best.


The entrepreneur does not always know best. I’ve found that the best way to build a business is to assume that you don’t. If you hire the most talented people you can find, give them structure and support, and trust that they will surpass your expectations, they almost certainly will. More than a few studies have shown that a critical leadership style only ever leads to disengagement, low morale and poor performance. Micromanagement indicates a profound distrust in the team’s ability to succeed; left unchecked, it can undermine staff confidence and prevent them from pursuing innovative ideas or enjoying their work. The hard truth of the matter is that a serial entrepreneur can only be effective if they take a step back and trust that the company will continue to achieve even after they leave to pursue other interests.


As a serial entrepreneur myself, I lived these lessons firsthand. I started my first post-college business — a bar and restaurant in South St. Louis — when I was in my mid-twenties and on break from the band I was in at the time. Within a few years, I had syndicated the business and raised over $100,000 for expansion. At the time, it would have been reasonable for me to make the restaurant my only business priority — but I had other ideas that I wanted to pursue. After five years, I sold the business at a profit, gave my investors a good return on their contributions, and went onto the next idea.


From that point on, I had the drive to break into all industries that interested me. Over the next three decades, I started ventures in banking, food, baseball, leasing, real estate, business, brokerage, supplies, pharmacy, automotive, management services, aggressive intervention services and educational software. Some might say that my portfolio is a little eclectic, but I wanted to pursue my interests. I believed that I could leave my mark on those sectors by providing better products, services and experiences than anything else on the market. I’ve been blessed enough to see those hopes come true — although success certainly didn’t come without hard work.


You see, serial entrepreneurs won’t achieve anything if they are only marginally better than the competition. They need to be significantly better. Take Byrd & Barrel, my chicken-centered restaurant in St. Louis, as a case study. When my partner Bob Brazell and I started building the business, we did so with the intent of serving the best chicken in St. Louis. We blended the convenience and affordability of fast-casual dining with Bob’s culinary thoughtfulness and creativity, and the results paid off — local magazines regularly cite Byrd & Barrel as the best place for chicken in the city.


Here’s the point: I’m not a fried chicken chef. I don’t know which ingredients in the buttermilk and dredge make the half-bird platter so good; I don’t know how to mix up Byrd & Barrel’s jalapeno malt vinegar sauce. Bob does — and as the partner with business savvy and entrepreneurial expertise, it’s my job to make sure he has the business structures and support he needs to deliver perfectly-fried results. That, in micro, is the role of a serial entrepreneur — to build the business, hire the best people, and walk away when appropriate knowing that they will achieve success.


If you want to be a successful entrepreneur, you need to approach every business with humility. You won’t know all the quirks of the industries you break into; you won’t have all of the answers. But, if you genuinely care for and support the people you hire to run your ventures, you will find a way through setbacks and celebrate achievements together. In my experience, finding success in serial entrepreneurship is always an exercise in trust and letting go.