Latest Chapter in Oakley’s Story is Helping Other Startup Execs Tell Their Own

After serving as CFO for three Triangle startups with $100M+ exits, Tim Oakley tries to share his experiences through his Thrivers Integrative Mentoring Program.

Tim Oakley is on a roll. You get the sense that he usually is.

For someone who began his professional life as an accountant and has spent the bulk of it as a CFO, he comes off as more revivalist preacher than number-cruncher. Holding court on a recent afternoon at the Unscripted Durham hotel, the third-generation Durhamite lays out his business and life philosophies in a seemingly effortless stream.

“We want to bring together the missionary and the mercenary, the heart and the sword,” he says at one point.

At another: “Our motto is basically how to crush it in business without losing your life… The question I get people to ask is, What’s the vision to want to do this piece? What’s the rallying cry?”

Later: “We focus on mind, body, heart, vocation. Look at your story—what chapter are you in? What do you want the next chapter to look like?”

And finally, on his hometown: “Durham is a redemptive story. There are a lot of warts to work out, but I love the vibe. We need to deal with the messiness. I’m trying to be in that story, to do my part to love and lead well.”

The “Thrivers Quadrant” is a visual that Oakley uses to demonstrate the appropriate balance of missionary vs. mercenary.

In the story of the Triangle tech startup scene, Oakley is now trying to do his part through his Thrivers Integrative Mentoring Program. Part coach, part counselor, part corporate consultant, Oakley has a half dozen or so execs from Triangle startups with annual revenues of at least $1M enrolled in the 15-month Thrivers program. The Thrivers members’ companies are a virtual who’s who of what’s hot in Triangle tech, including Teamworks, First, StrongKey, and Smashing Boxes.

“Obviously, business success is a key goal,” says Mitch Heath, the Chief Growth Officer of Teamworks and a Thrivers client. “But execs also want to be physically fit, mentally strong, spiritually attuned and enjoying healthy relationships with their family and friends… I have been working with Tim for over a year and no one really offers a program akin to this one.”

The Thrivers participants meet once a month as a group for four hours, where they are encouraged to share their professional and personal issues. Everyone signs a nondisclosure agreement to help the honesty flow. Oakley brings in speakers ranging from businesses figures like Steve Nelson, the former CEO of Silicon Valley unicorn Carbon; to Luke Powery, the Dean of Duke Chapel, to discuss spirituality.

Members can also meet one-on-one with Oakley for up to three hours a month for individual coaching. Says Oakley, “It’s everything from your cap table to contracts, from your kids to your marriage.”

As much as they might rationally understand that a well-balanced life will help a startup exec lead a better business, though, it’s hard to picture most C-suiters spending such significant time and money to get a few self-help tips from someone without impressive business experience. That’s where Oakley’s track record with successful startups gives him unusual credibility among the corporate-coaching crowd.

From CFO to Counselor

Oakley served as CFO for three Triangle startups that generated exits of more than $100M—Opensite (2000), iContact (2012) and Appia (2015). In the latter two cases especially, Oakley served alongside talented young founders like (Ryan Allis and Jud Bowman, respectively) who could benefit from an experienced hand.

“I’d generally come in as an operating CFO,” Oakley says. “The right fit was a company with a good idea, with maybe a half-million to $5M in revenue, looking to grow. My role was attracting talent, attracting partners, and growing the business. And I’ve always owned HR.”

Even while working as a CFO, Oakley earned a Masters in psychology and then a certification in health coaching from Duke, which stresses integrative health—a holistic approach to wellness focusing on body, mind, and spirit.

Oakley has turned Thrivers into his fulltime gig with the help of his partner, Vance Brown, a close friend going back to their days at Durham’s Northern High School and a successful entrepreneur in his own right. Brown is the Founder and Chairman of Cherwell Software, which recently raised $172M from KKR. Oakley also teamed with Brown at Cherwell for a stretch.

“Vance was valedictorian in high school, and let’s just say that I was not,” says Oakley. “He and I have been living out this model for 25 years. It’s all about transparency and living out your values.”

Oakley is clearly an expert at living those values—and life—out loud.

About Pete McEntegart 14 Articles
I've worn many hats, but my current chapeau* is as Managing Editor of GrepBeat, a media startup covering the Raleigh-Durham startup community. Sign up for our Tuesday-Thursday email newsletter at grepbeat.com. Hope to see you around the Triangle! (*chapeau is French for "pretentious")