Who is the Real CEO of “YOU, Inc.”?

I’m not sure if this is a blog or a statement of purpose or a laundry list of experiences. For the reader, that probably amounts to a lame expectation of “choose your own adventure.”

Trust your gut.

Over the last 25 years, I’ve gone from an “N” of 75 to an “N” of 3 to an “N” of 2 to an “N” of…ONE. Steve Jobs has a great commencement address to the 2005 graduating class at Stanford where he talks about your ability to “only connect the dots looking back” to make sense of how your life is playing out in the present. I’ll link to it HERE. It’s obviously brilliant and worthy of 15 minutes of your time.

While I’m not interested in creating a computer hardware and software ecosystem or changing the music business, I do think there are some lessons in a few dots that litter my past.

Connecting My Own Dots

I grew up in a family business, Thompson Dental Company. The business was founded in 1899 by my great grandfather, James Perrin Thompson. I entered the business in 1995 when my father was President and CEO, and my grandfather was Chairman of the Board. The business had over 400 employees and 13 sales branches from Baltimore, MD through Orlando, FL. At a glance, you might judge that to be a successful business—and from an operational and financial standpoint, I’d agree. From an ownership and governance standpoint? Well, family businesses aren’t always inside what they appear to be from the outside. If I polled the audience to ask how many had ever heard their aunt call their father a “thief in the night” at a family meeting, my hope is that it would be zero.

The first dot here would be that families and businesses are dynamic entities that require an incredible amount of trust, communication and love to maintain and grow over time. We should all choose wisely when we make commitments, and we should do so with full awareness of how intermingled that can absolutely become – especially when we’re only one, small family together.

What Are the Odds…?

According to Cornell’s SC Johnson College of Business, “The average life span of a family-owned business is 24 years (familybusinesscenter.com, 2010). About 40% of U.S. family-owned businesses turn into second-generation businesses, approximately 13% are passed down successfully to a third generation, and 3% to a fourth or beyond (Businessweek.com, 2010).

You probably didn’t need a reminder about how hard it is to build a “legacy business” regardless of your field. While Thompson Dental Company successfully transitioned from its first to second generation owner, it never stood a chance of making it from second to third – let alone third to fourth. We were forced to sell the business to Patterson Companies in April of 2002 not for operational or financial reasons, but due to poor equity transition planning. Neither of my father’s two sisters, nor their husbands, nor any of their children worked in the business.

The second dot here would be that those of us who build growing businesses at some point will most likely want to bring on additional partners. Potentially some of us may have started businesses with founding partners. The dynamics of business ownership and the unrelenting challenges of entrepreneurship are all encompassing, so “non-operating partners” can create financial conflict that is unresolvable. Unfortunately for yours truly, this proved to be a repeatable pattern later in life. Note to self: the first time something happens, it’s a “learning experience”; the second time it happens, it’s “a YOU problem.”

The Value of Wisdom from Advocates & Mentors

My entry into Patterson Dental Company was bumpy and my continued employment was far from guaranteed. I guess my father felt like I needed to be sure I would be retained based on merit over nepotism. The right call for sure, but was incredibly agonizing for a 31 year-old. In the midst of that turbulence during the integration phase, I had one thing going for me. One person, actually – Randy Eckard.

Randy had been Thompson’s VP of Sales and had seen something in me at an earlier age when I was a software sales rep for the company. He “hired me away” from my hometown (so I could get out of the shadow of my father) and had brought me to Raleigh to build a small team that would sell, install, train and support the software platform the company was developing. We were massively successful. Randy saw firsthand what I was able to do and ultimately was able to build at an organizational level, so he threw his (relatively insignificant) weight behind me for a leadership position somewhere – anywhere – in Patterson.

For as successful of an acquisition and integration that Thomspon had been for Patterson, the Richmond, VA branch was an epic disaster. The branch had basically imploded under the legacy of nepotism, dishonesty, theft, and an insular culture of “me first.” What idiot was going to be dumb enough to take that job?

I’ll let Bob Dylan answer that: “When you ain’t got nothing, you got nothing to lose.”

At 31 years old, I became the new General Manager of the Richmond Branch of Patterson Dental Supply—a dumpster fire with a glass front door. The employees were so excited that several were heard to remark: “Oh great…they bought the old man’s company, and we inherited the kid.”

I was the youngest person in the branch by several years and was still able to remember some world history, notably a quote from Sir Winston Churchill: “If you’re going through Hell, keep going.” I was, so I would. After less than 18 months, I had turned over 60% of the people, started to create a culture of accountability and trust, and secured some solid sales wins. One person who took notice was Bob Foss, the award-winning, veteran General Manager in Baltimore – my “neighbor to the north.”

Bob had watched from afar how the prior regime had created a business only the mafia could admire, so when I became “an agent of change,” he quickly took me under his wing to teach me the best ways to run a branch and to be a respected operator in the company. I wasn’t that smart, but I was smart enough to listen. I also went to Baltimore to observe. They say, “success leaves clues,” but if you want to know the answer to the test, go ask the teacher who wrote it. And then stay after class to ask them what the answer actually means.

If I ever write a book, “The Value of Mentors” will be chapter one. And that’s the third dot. I wasn’t intentional. I wasn’t smart. I wasn’t humble. I was lucky. Being “the boss’s son” made me the third rail, if anything. Both Randy Eckard and Bob Foss were legends in their respective companies and leaders who didn’t need anything from me or my father. They both already had it all. They both took me under their wings because they saw something in me that others (including myself) didn’t see, then they helped give me a playing field to be great. I got lucky because Randy and Bob adopted me. Don’t rely on luck. Seek and find your own mentor who will share their experience and their wisdom to accelerate your learning curve.

The fourth dot is critical in the early stages of your career every bit as much as finding the right mentor can be: you often have to leave your hometown, your comfortable routine, your lifelong friends, and even occasionally a romantic interest to put yourself in the middle of a worthwhile opportunity. I moved from Raleigh to break away from the legacy of my youth (and my family…to a degree), then I left dear friends to move from Raleigh to Richmond to bet my ill-defined career on a turnaround that couldn’t fail any worse than it already had. Then I did it again, moving from Richmond to New York City. Relocating is turbulent and stressful. Do it while you’re young. I bet on myself several times because I thought the odds were in my favor.

Be Prescient and Stay Adaptable

I was in my late 30s, single and living a pretty good lifestyle in Manhattan. The business I was running was performing very well and I had been asked to interview for a few Director-level positions at the corporate headquarters…in Minneapolis. Keep in mind, I grew up in South Carolina. I gracefully bowed out of one particular role that would’ve been career-altering had I taken it. It did, however, force me to ask myself what I wanted out of this next stage of my career. And the answer to that was a combination of a return to the Southeast and the opportunity to run a smaller market.

Dot number five comes in the form of horizons. My parents’ generation were “the career employees” who worked for one company for 40 years and retired with a gold watch and a pension. That wasn’t going to be me, and it surely ain’t going to be you. The world we’re surrounded by and the markets we choose to serve change rapidly, and in an economically Darwinian kind of a way, we need to be the agent of change for both ourselves and our businesses. I chose to be the author of the last stage of my Patterson career by making a lifestyle change in hopes of what the next phase would become. Charlotte proved to be all of that as I met my (now) wife here and we started a wonderful family. Stability matters. So does being adaptable.

Are You Really in Control?

Charlotte was a business that was more akin to a rudderless ship for several decades, but I knew a lot about the market and most of the people, so it was a job where I felt I could make a difference. After only 14 months, the President and VP of Sales of the company basically threatened me with my job if I couldn’t turn it around – which is always nice to hear when the prior General Manager was in place for over 20 years. A year later we were runner up in Branch of the Year Honors. Hashtag “Vindication.”

A year later, I received a scathing performance review from my Regional Manager where almost every category was noted as “Needs Improvement.” Hashtag “Are You Kidding Me?”

It was at this point that I realized I was not going to finish my career working for Patterson. I simply couldn’t stand the thought of going to work every day with the sword of Damocles hovering above my head. In the corporate world, your career is decided upon by someone else…when you’re not present in the room. Dot number six is the reality that we all work for ourselves, only most of us don’t realize it. Over the next 3 years, I took the time and did the research to craft my exit on my terms from the company. And we won two Branch of the Year awards (and one more runner-up) over that same timeframe. Hashtag “Not-So-Humble Brag.”

What It Is vs. What It Was

When I left Corporate America in early 2017, I launched a start-up with four other founders that went on to become TUSK Partners. TUSK was at first an online brokerage platform for buying and selling dental practices (think “Zillow.com for Dentistry”). Brilliant concept. Lots of potential. Way underfunded. To use a tech term, we pivoted into a consulting and sell-side advisory firm that focused on group dental practices. We built out a tremendously successful, yet painfully traditional, people-driven advisory firm. Nothing “exponential” about it. The one thing we got right was timing. We built a brand at the point the market needed a resource, and we capitalized on it. And this is dot number seven: if yours is an emerging business or concept, timing matters more than the idea itself. For those who don’t believe me, watch Bill Gross’s TED Talk on “Why Startups Succeed.”

After four incredibly successful years at TUSK, including one global pandemic, one of my partners and I decided to leave the company to start a competing firm, Polaris Healthcare Partners. Every one of us looks back on our past and can hopefully take away some positives along with a few negatives around each of our experiences. Living the experience tends to cloud your objectivity, but time does help. For me, TUSK was a successful company, but unfortunately a failed partnership. Dot number eight comes from the learned experience of building dynamic, intense businesses with partners and how any misalignment in vision, expectation or risk can create insurmountable challenges. My advice is to take the time to explore all of the uncomfortable questions prior to becoming partners, then (much like a marriage) do everything you can to nurture the relationship over all of the businesses’ ups and downs.

How Many Dots Are Left?

As I round into my early fifties(ish), I’ve been able to aggregate my experiences from working in Corporate America along with my success as a full-fledged entrepreneur in two successful start-ups as well as my consulting with many group practice founders. These lived experiences have created some bank of practical wisdom that has helped me better understand this next phase of life and stage of my career. Dot number nine arrives in the form of a better understanding of the necessary congruency of the work we do and the lifestyle we lead with the people with whom we choose to surround ourselves. It’s every entrepreneur’s greatest aspiration to find joy, fulfillment and purpose in the work we do – which almost always found in work that serves others.

If in reading this, you find yourself thinking that the dots came faster and more frequently toward the end, you’re right. They do – which is dot number ten. As we become older, we hopefully become wiser. That growth in wisdom results in an emerging ability to better “read the tea leaves” and interpret the world around us. Your mental data bank of experiences creates greater connections, associations and interpretations…if you’re willing to give it time to percolate.

Dot number ten is that YOU are an individual with unique experiences, so take the time to nurture your creativity and mine your mastery. Accept the responsibility that you – and you alone – are the CEO of “You, Inc.”