Season 3 of Uncharted: Your Sidekick for Life continues to pull back the curtain on stories that challenge, inspire, and occasionally slap you in the face with perspective.
Episode 8 introduces us to Matthew Thomas, an entrepreneur and mentor whose journey began with a clear path in mind, only to discover that life’s most meaningful moments often come from the detours we never planned.
“Sometimes I think we can get so focused on a single path that we forget to ask ourselves… do we even want to go there?”
Growing up in Mustang, Oklahoma (neighbor to Garth Brooks’ hometown, because of course), Matt was the quintessential "good kid"—Eagle Scout, straight-A student, laser-focused on getting into the Air Force Academy. He wanted to fly. There was just one problem: his eyesight had other plans. It turns out, dreams are harder to chase when you can’t see where you're going.
But Matt didn’t realize that until it was too late. He had built his entire identity around the goal of becoming a pilot, so when reality hit, it wasn’t just his vision that blurred—it was his sense of self. He tanked his first year of college, burned through scholarships, and found himself working at a nuclear power plant in Arkansas. Not exactly Top Gun material.
“That job was my wake-up call. I realized if I didn’t get my act together, my only future would be punching a clock in a place I didn’t love. And I couldn’t stomach that.”
So, Matt pivoted. He went back to school, switched his focus to mechanical engineering, and worked 20 hours a week while taking 18 hours of classes. He learned a hard truth: hyper-focus can be just as dangerous as aimlessness. Having a North Star is great—but not if you’re walking off a cliff to reach it.
But here’s where the story takes its turn from "grit and grind" to something more human. Matt’s life didn’t really open up until he stopped trying to control it.
It’s the same realization Becky Henderson spoke about in the first episode of Uncharted: Your Sidekick for Life. The episode began with a simple yet piercing question: “Do you want to live a life where you continuously try to predict, micromanage, and anticipate the future?”
Becky explained how the fear of the unknown traps us in rigid mindsets, convincing us that control equals safety. But Matt’s story stands as living proof of Becky’s insight—it’s often the moment we relinquish control that life opens up in unexpected, beautiful ways.
A friend, Burgundy Kelly, invited him to visit New York. It was his first time in a city that big—8 million people, food he couldn’t pronounce, cultures he’d only read about. It hit him like a freight train: There’s more out here. So much more. Within months, he had a job in Brooklyn—two hours each way on the Long Island Railroad—because once his aperture widened, there was no squeezing back into the narrow view of his small-town upbringing.
That openness became his superpower. He didn’t plan his career so much as stumble into it, one opportunity leading to the next. He took an MBA at UT Austin, not for the degree, but because someone cornered him and said, "You have to take this class with Jack Long." Jack, a no-nonsense entrepreneur in flip-flops and a surf shirt, ran a side-course out of a Sunday school room, handing out Harvard business cases in a three-inch binder and making students sign a contract: show up prepared, or your $400 deposit gets cashed. "I spent more time on that class than the ones I was actually paying for," Matt laughs.
But it paid off. Jack didn’t preach—he asked questions, poked holes, made Matt think. And more importantly, he showed Matt that entrepreneurship didn’t have to mean gambling everything in Vegas. It could be thoughtful, calculated, purposeful.
When Matt co-founded AcademicWorks, it was Jack’s vote of confidence that sealed the deal. "If you go do this, I'll back you," Jack told him. And he did.
Today, Matt pours his energy into mentorship—because, as he puts it, "If only 10% of people have mentors, how many lives are we leaving on the table?" Through the Entrepreneurs' Organization (EO) Accelerator, he helps founders scale from $250K to $2 million, not by giving advice—“That just turns into blame when it doesn’t work”—but by sharing experiences. Peer-to-peer mentorship, like a 12-step program for business owners, minus the coffee and folding chairs.
“When you hear someone else’s story, you don’t just get their solution—you get permission to rethink your own.”
Matt’s story reminds us that life rarely follows a straight line. Sometimes the best opportunities show up when you’re least prepared—like a nuclear power plant in Arkansas, or a random class in a church basement. The real question is: when the detour presents itself, will you be too focused on the path you planned to take it? Listen to "From Engineering to Entrepreneurship with Matthew Thomas"
Matthew Thomas is an Austin-based entrepreneur and mentor with a focus on EdTech and SaaS startups. He co-founded AcademicWorks, a platform that streamlined scholarship management for educational institutions, later acquired by Blackbaud (NASDAQ: BLKB). Since then, Matt has advised and invested in startups like Earthly Labs (acquired by Chart Industries) and Crave Retail. He also works with the Entrepreneurs' Organization (EO) Accelerator, helping founders scale their businesses. When he's not mentoring, you'll find him running around Lady Bird Lake, balancing his love for marathons, homebrewing, and Nutella.
Natalie Peyton: Peyton studied theatre and film in Australia, New York and LA and performed stand-up on the “three coasts.” She honed her podcast executive skills over the last 4 years developing and producing dozens of podcasts and even hosts a children’s mindfulness bedtime program. If you would like to listen to her work, here it is: Snoriezzz
Leon Vanstone: Leon brings his curiosity and sharp interviewing skills to the table, facilitating insightful discussions with our mentors, extracting valuable lessons and insights to empower listeners on their own path to growth and achievement.
Dan Dillard: Dan, with his thoughtful approach and engaging style, delves into the minds of our mentors on the podcast, crafting compelling interviews that uncover the wisdom and experiences driving their success and impact.
This blog was written by Anais Schmidt, one of the hosts of the Uncharted Podcast. Anais is also an aspiring musician. When not in her studio, she tours Europe with Monte Mai.
If you would like to join the conversation email us at anais@foundingup.com
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