Students For Liberty has a new COO: Will Riddle.
He spent the last decade at Prison Fellowship, where he rose from Director of Field Operations to SVP of Strategic Initiatives. He oversaw 280,000 constituents, a team of 70, and a $10 million budget. Before that, he spent a decade at IBM as a Business Transformation Manager, leading global deployments across more than 60 countries.
He was slammed on his first official day; “drinking from a firehose,” as he put it. But he still gave me 45 minutes to ask everything I could think of. Here’s our interview, edited lightly for clarity.
Q: So, who the hell are you and why should I care?
A: I sometimes introduce myself as “The Mystery Man.” I seem to show up at the most unexpected times and places. I guess you could say I’m a Riddle.
More seriously, though, I was raised in Central Florida; my dad worked for NASA at the Kennedy Space Center. We watched every launch growing up. In fact, I was there in person when the Challenger blew up. I ultimately worked there for two summers, then went to school, had a great career at IBM, and then at Prison Fellowship. And I’ve had a lifelong passion for freedom.
Working in ministry, I saw firsthand that part of the reason people’s lives fall apart has to do with policy and how we incentivize people to do things. There is a deep connection between how you help individuals and how you help the whole society. The free market has answers for both.
Q: What are some similarities and differences between your previous jobs and this one?
A: One similarity is from the perspective of human freedom: We all aspire to manage our own lives and our own freedoms. People I worked with at Prison Fellowship are very early in that journey, but we’re all pursuing full autonomy.
Another similarity: Our core values were humility, collaboration, excellence, and holistic restoration. You can probably guess how I felt when I saw SFL’s HOPE values.
And then, at IBM, I had teams all over the world. So when I saw how diverse the SFL staff is, I knew it was going to feel like home. The job posting said they were looking for someone to build the culture and manage distributed teams, and I was like, “Well, that’s exactly what I do.” Everything I’ve done in life converged for this role.
Q: Who’s your favorite Batman villain?
A: You want me to say The Riddler, right? Well, instead I’ll tell you my favorite overall Batman character: Robin. Because I like to be the wingman. Not necessarily getting all the credit or spotlight, but always ready with support to make sure the superhero gets his man.
Q: Why on earth, of all the places you could’ve lived, did you choose *checks notes* Tulsa, Oklahoma, where it is currently *checks notes* a million degrees?
A: It all has to do with the ring on my finger. My wife was looking for a fresh career. We played 20 questions about her next step, and narrowed it down to academia. She started working at Oral Roberts University in Tulsa. So I moved there for her.
I’m spoiled; I’ve lived in Kansas City, Cincinnati, Boston, Durham, North Carolina … those have all been amazing places. I like Tulsa, too, but what I like most about it is Jaime Riddle.
Q: You studied at Duke. Were you a Cameron Crazy? [Editor’s note: Duke University’s basketball team is generally one of the best in the country, and their student cheering section is generally one of the rowdiest and craziest in the country. They play at Cameron Indoor Stadium. Hence: Cameron Crazies.]
A: I love Duke Basketball, but to be a TRUE Crazy, and to get the best tickets to the best games, you have to camp out for, like, 6 weeks in the wintertime. I was a little too focused on school to go to those lengths, but I was a resident advisor, which helped me get tickets.
Q: Why take this job?
A: At Prison Fellowship, I was able to work at something I was passionate about. Now that I’ve had that experience, I never want to do something I’m NOT passionate about. But I felt like I had achieved everything there that I could, so when this job came open, I knew immediately: It fit me super well. It was a no-brainer to apply.
Q: Have you always been a libertarian?
A: I would say I’ve always been pro-freedom, but it was the 2008 election that really got me more politically involved. I began to see the hyper-politicization of our government, and that it was moving toward socialism. I started proactively looking for ways to be involved. We volunteered on a congressional campaign, started showing up at various events, and even did some homegrown activism in school choice.
When I started working with people on the street in recovery ministry, I became even more convinced that everything flows from personal responsibility. So while some might look at my resume and wonder how it all fits together, to me it’s completely consistent: I’m in this because I care about people.
Q: So where do you place yourself within the movement?
A: I’m careful with labels because everyone has slightly different understandings of what they mean, but I think you could comfortably call me a classical liberal. If you want to know how I think in terms of political economy, I would just say pick up Thomas Sowell. I pretty much love anything he writes. My favorite book of his is The Vision of the Anointed: Self-Congratulation as a Basis for Social Policy.
Q: Who’s your all-time favorite libertarian? Wrong answers only.
A: [Laughs.] Whoever was really running the Biden administration. Joseph Stalin a close second.
Q: What do you see as your first order of business?
A: The very first one is to get to know everybody. They say personnel is policy. Everything flows from having the right people and having the right relationships with the right people. I want to get to know the team, what their aspirations and frustrations are, and build great relationships.
From there, we’ll look at: Are there some things that I can help with, as a central source for addressing pain points? Wolf shared a lot with me about the core values and the kind of culture he wants, and building the culture he’s imagining. There’s already a culture of innovation and entrepreneurship, so I want to build on that, too.
I taught a class in India once, when I was with IBM. The way people answer questions I posed to the classroom is just so creative and self-organizing: Everyone starts speaking at once, there’s no hand-raising or anything … and then out of the 35 people or so, eventually just one person completes the answer and the others know to stop. It’s a self-organized solution to chaos. It’s very libertarian, and I think very SFL.
Q: Speaking of international travel, now that you work for a global team again, where’s the one place you’re most looking forward to visiting?
A: I have to confess: I’ve never been to continental Europe. I’ve been to the UK, but never to the continent, so I’d like to start there. I also have a deep-seated curiosity for some obscure places, like Kamchatka and maybe Lake Baikal.
Q: Do we have students there?
A: Not yet …
Q: What’s your all-time favorite riddle?
A: My daughter, Abigail Riddle.
Q: Touche. Alright, last one: What’s the most interesting thing you haven’t told me yet?
A: Man, tough one. You know that game Two Truths and a Lie? Well, one of the “truths” I usually go with is: I’ve been to prison in 20 states. People think that’s the lie, but it’s true!
Another cool thing is that when I was a little kid, my grandma took me to the top of the U.S. Capitol. We even got to go out on the balcony, which is typically exclusive, but my grandma was important in politics in her little county in West Virginia, so she was able to make it happen.
Looking out over D.C. stuck with me for life. It gave me a desire, and helped me realize that we’re incredibly fortunate to live where we live. And ever since then, I’ve had a lifelong passion to defend freedom.
