Meet TC: CFO, Dad, Swimmer

  • Published:
    Sep 28, 2022
  • Category:
    Apprentice All-Stars
“I’m a strategic, forward-thinking operating finance executive with over 25 years of industry and corporate experience in a broad range of industry sectors.”

Get to Know TC

What motivates you? For me, life isn’t just about looking at the hill that needs to be climbed and charging up it. It’s also about pausing to reflect on the best path forward — leveraging the best tools and people for the occasion — to not only solve problems, but also to make the journey part of the fun.

What’s your work superpower? I’m inherently creative in how I approach workplace challenges. In addition to being focused on analytics, I’m also mindful of the importance of maintaining a broader sense of empathy and inclusion. Being married to an artist/author appears to have rubbed off on me…

What’s your non-work superpower? Being active. To me, exercise is a form of therapy, which is why I participate in distance events such as triathlons, marathons, centuries — you name it! Just make sure that Advil and a bag of ice are handy…

And back in the day, I managed to achieve All-American status competing in swimming at the NCAA Division I level. But, arguably, my greatest achievement outside of work… was marrying up!

Heather Ross, TC’s wife, has dragged him onto television multiple times in connection with her successes as an artist and an author. It’s clear to all (read: TC) that she’s the more interesting of the two…

Where do you like to travel? I’m an avid traveler, and have circumnavigated the globe more times than I can count — mostly done in my 20s! I’ve also lived in a number of different places in addition to the Catskills, including Manhattan, Brooklyn, Barcelona, Chicago, San Francisco, and London.

One of my most memorable trips was when I spent six months in Southeast Asia traveling through Cambodia, Vietnam, Thailand, and Australia. Best of all though, we are fortunate in that we have an off-the-grid getaway in Vermont — a favorite go-to!

When TC and his family are in Vermont, the closest cell signal is in Canada… if it even exists.

How do you spend your free time? In addition to training, my favorite way to spend time is with my family. I have a curious and precocious 11-year-old daughter, an artistic and clever wife, and four adopted pets (two of which we saved from the streets of Puerto Rico). I don’t love all my pets equally, but don’t tell them that! Oh… and I should mention Wordle…

TC and his family posing with what looks to be an epic BBQ.

Looking Ahead: A Day in the Life of TC

When you’re building scalable operations, you have to always be looking ahead. I’m constantly asking myself questions such as: “What’s around the corner?” and “Where will we be — the company and the industry — in six months, in twelve months, in two to three years…?” 

You can’t just solve today’s problems in a silo; you have to think geometrically by contemplating next-level problems as well. This requires a balancing act — crushing today’s hurdles while setting ourselves up to crush tomorrow’s as well.

TC and his family enjoying the natural beauty of the Catskills.
“Life is much about learning and identifying what’s important. And then juggling those priorities every day. Sticking with the analogy — being excellent is not always about keeping every ball in the air all the time. That would be great, but it's simply not sustainable. Rather, excellence is about ensuring we are well positioned to pick up a dropped ball after only one bounce. If you’re not willing to let a ball drop on occasion, you’re not positioning yourself to learn as much.”

Fun Facts About TC: Rapid Fire Edition

We asked, TC answered. Here are some fun facts about TC:

When did you realize you wanted to pursue a finance career? I spent the first 15 years of my career as an advisor. I made the leap of faith to become an operator when I realized how tech can be used to solve some of the biggest problems I faced as an advisor. Once I jumped over that line, there was no turning back.

What about finance inspires you daily? The order and insights it brings about every day.

What’s the title of your autobiography? CFO Dad.

TC and his daughter spending some quality aquatic time in the lake.

Where were you before joining Apprentice? At a healthcare tech company with a similar north star: to improve the healthcare system by leveraging technology. During my tenure, we were able to grow the company 5x in 2 years. Prior to that, I was with a Big Data Analytics SaaS company; during my tenure we were able to grow the company 10x.

What excites you the most about joining Apprentice? There are four pillars that excite me about joining Apprentice. These include:

  1. Our investment thesis — the opportunity to create value
  2. Our people!
  3. Mapping my skills to needs of the company at this stage of growth
  4. Apprentice’s mission of making a lasting impact on healthcare for all

What about our brand mission resonates with you most? Improving the healthcare system by making therapeutics more affordable and accessible through cutting-edge technology.

Best piece of advice you’ve ever been given? Life is much about learning and identifying what’s important. And then juggling those priorities every day.

If you had a time machine but could only use it once, would you go back in time or into the future? Where and when would you go? I would go into the future; just far enough to see what life brings my daughter’s way when she’s full grown. Oh — and a glimpse of how the markets have behaved wouldn’t be too bad either…

Looks like TC’s daughter shares his love of swimming — like father, like daughter!

TC's Pets: Meet the Menagerie

It wouldn't be a Spotlight without some adorable pet photos to round things off! So without further ado, meet the dogs and cats of the Fleming household:

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