🎙️ Rise to Run Podcast – Episode 11: “Career Chaos, Dogs, and Dutch Last Names” Guest: Leora Opstelten

In Episode 11 of Rise to Run, Alan is back with his trademark unfiltered energy, joined by the fierce and funny Leora Opstelten—a career counselor who’s made it her mission to help veterans navigate the often brutal transition out of military life. If you’re a vet who’s ever felt like civilian life is harder to crack than a secret mission, this one’s for you.

Leora brings both heart and humor to the conversation, as she and Alan dive into her journey from growing up in the shadow of Stanford University to finding her stride in Los Angeles. From escaping the chaos of high-stress law firms to falling into the world of recruiting, her path hasn’t been linear—but it’s been deeply impactful. Along the way, we hear about her stubborn and lovable pittie-shepherd-husky mix, who doubles as a service dog and emotional support queen, and why her Dutch last name might literally mean “on stilts.”

The episode goes off the rails in the best way possible—touching on everything from ancient Jewish pyramid labor conspiracies to what it’s like dating a Jewish Marine she met on JDate (yes, seriously). Alan and Leora’s banter is hilarious, real, and at times, surprisingly deep.

This episode is a rollercoaster of stories, laughs, and real talk that hits home for anyone who's ever had to start over, love a stubborn dog, or figure out what the hell to do after life throws you a curveball. Buckle up—it’s a good one.

In this brutally honest and deeply heartfelt episode of Rise to Run, host Alan welcomes longtime friend David Oltman for a no-holds-barred conversation about life’s highs, lows, and everything in between. David shares his journey growing up on a Minnesota hobby farm, facing a tough childhood, and learning financial survival skills at an early age. From flipping hay bales to losing jobs during the 2008 recession, his path wasn’t easy—but it was real.

David opens up about losing some of the closest people in his life, including his brother, best friend, and mentor, and how those experiences shaped his perspective and purpose. Through laughter, military banter, and painful memories, he walks us through how those dark moments helped him build his own insurance agency and a life of meaning. The conversation dives deep into grief, grit, fatherhood, and the responsibility of being a leader both at home and in business.

Whether you’re in a tough season or on the verge of a breakthrough, this episode is for you. David’s story is proof that it’s okay to not have it all figured out—just don’t stop moving forward.

Press play. Because someone’s story might just be the thing that changes yours.

Precision, Purpose, and the Power of Brotherhood

In this emotionally raw and powerfully transparent episode, the host welcomes Julian, founder of Precision Wraps, to share a deeply personal and transformational story. From struggling through a painful childhood, addiction, and life-threatening moments to finding redemption, brotherhood, and purpose, Julian’s journey unfolds in real time with honesty, grit, and humor.

As the episode begins, the two veterans poke fun at their warm Florida weather while the rest of their Uncaged brothers freeze up north, setting a lighthearted tone before diving deep. Julian opens up about his early life in Ohio, his struggles with addiction, and the pivotal moment that sparked change: seeing a photo of his premature son while coming off an eight-day meth bender. From there, he recounts how he got clean, left everything behind, and took a leap of faith by starting his business with just $300 and a borrowed garage.

The conversation evolves into themes of self-worth, faith, fatherhood, and healing. Julian reflects on his relationship with his wife, Michelle, their hardships, and the grace she's shown him through it all. He credits the Uncaged community for helping him break cycles, rewrite his identity, and become a better man, husband, and father.

Together, they talk about the importance of surrounding yourself with people who hold you accountable, the healing power of telling your story, and building a legacy of strength and love. Julian’s vulnerability shines as he shares how close he came to ending his life, and how a quiet spiritual moment and the support of his community pulled him back.

By the end, Julian shares his vision for the next chapter: renewing his vows, showing up for his kids, building a half-million-dollar company, and giving time back to his family. This episode is not just about business or resilience — it’s about brotherhood, belief, and becoming the man you were always meant to be.

If you're struggling, this one’s for you.