Uncharted Your Sidekick for Life

In this special episode of Uncharted, we sit down with Dr. Bobby Robbins—physician, educator, and higher-education leader—to explore what modern university leadership requires in a rapidly changing world. Dr. Robbins is currently a Visiting Distinguished Fellow at the Hoover Institution at Stanford University. He previously served as President of the University of Arizona and President & CEO o...

In Part 3, Léonie Weerakoon shares her clearest advice for the next generation: stay curious, ask questions, and give yourself permission to evolve. Léonie talks about building resilience inside real-life constraints, why authenticity is a long-term advantage, and how to think about career decisions without treating them like permanent life sentences. Dan connects it to a powerful Gen Z insight: w...

Part 2 of 3 • Mentorship What if mentorship isn’t one person… but a lifetime of elders, cultures, mistakes, and questions? In Part 2, Léonie Weerakoon explains how her cultural upbringing and traditions from travels to  storytelling shaped her view of learning, why most of her early “mentors” were men (and what that disconnect taught her), and how travel became her real teacher. She also talks abo...

Part 1 of 3 • The Map Léonie Weerakoon grew up between continents—and it shows in how she thinks, builds, and moves. In Part 1, Léonie shares her global upbringing (Austin, Vancouver, Luxembourg, Sri Lanka, New York), her early creative roots in fashion and design, and the unexpected academic detours that made her both an artist and a scientist. She also tells the origin story of how she ended up...

Part 3 of 3 • The Takeaways. Neal closes the series with the lessons he wishes he’d known earlier: risk, belief, failure, translation, and keeping your creative spark alive. Co-hosts: Natalie Peyton Neumann & Dan Dillard.

Part 2 of 3 — Mentorship. Neal unpacks the mentors who shaped his path—from harsh early bosses to the advisors who helped him bet on himself and move across the world. Co-hosts: Natalie Peyton Neumann & Dan Dillard.

Part 1 of 3 — The Map. From dyslexic kid in Northeast England to engineer, comedian, and Cisco’s higher-ed “translator,” Neal Tilley shares the early twists that shaped everything that came next. Co-hosts: Natalie Peyton Neumann & Dan Dillard.

Part 3 — The Takeaways with Amber Gunst Failing forward under scrutiny, the right kind of vulnerability in leadership, guiding teams through layoffs/furloughs with care, mental-health habits (walking meditation, therapy when it counts), favorite reads, and Amber’s 45/15 deep-work cadence. We cover: • Failure under scrutiny & resilient self-talk • Vulnerability vs. venting in leadership • Crisi...

Part 2 — Mentorship Advice is cheap; mentorship is earned. Amber breaks down how she built a “board of brains,” asks busy leaders for targeted help, and structures warm introductions so people actually respond. We also get into negotiation prep—including the gender dynamics no one explains—and how to pick which advice to ignore. We cover: • Advice vs. mentorship (and how to ask) • Warm intros that...

Part 1 — The Map From small-town Michigan and first-gen college to sales with an English degree, Amber Gunst moves to Austin during a recession, builds networks at the Chamber, and—within 11 months—steps into interim CEO at the Austin Technology Council. We talk about:• Why English → sales actually works• Building warm networks in a new city• Betting on commission is better than base• Jumping from...

From Cold War Poland to Detroit factory floors, from teenage radio news to helping launch cable-TV greats and then building hit video games ( Civilization , Origin/EA), Fred Schmidt’s path is anything but linear. Now an Austin entrepreneur behind Wild About Music, Austin Rocks, Toy Joy, and Yummy Joy, Fred shares practical wisdom for a screen-native generation. We cover: Luck = preparedness × oppo...

From stage-loving six-year-old to event producer at 22, to new mom navigating metastatic thyroid cancer, to founder of Alchemy Juice and mentor to a 600-member business community—Carly Brown (@carlyloveskale) is a masterclass in courageous pivots. We cover: Mindset > mechanics: “Jump, then build the parachute.” From facilitating the stage to standing on it. Healing, sovereignty, and starting Al...

Natalie Peyton Neumann sits down with Dwayne Goetzel—attorney, father, creative thinker, and someone who’s navigated career choices without a roadmap. They talk about growing up in Kerrville, the unexpected moment in Germany that pushed him toward law, and how hard truths early in his career helped him grow into a trusted expert in intellectual property. This episode covers mentorship, money, pers...

Join Natalie Peyton Neumann as she dives deep with Shawn Livingston, former Airman turned I Am Redemption podcast host. From childhood dreams of WWE wrestling to a heartbreaking car accident, disillusioned military service, heroin addiction, prison, and 4 felonies—Shawn unveils every low point. But the real transformation begins when recovery, running, and community intersect. Hear how ultra‑runni...

What if your whole life changed in a single night? For Johnny Goudie, it happened at a Cheap Trick concert at age 13 — and he never looked back. In this episode, Johnny shares how he turned heartbreak, hustle, and a love for melody into a decades-long career in music and podcasting. With raw honesty and sharp insight, Johnny reflects on how a mentor saved his path, why consistency beats talent, an...

What do you do when you’ve made it… but still feel the pull to do something that matters more? Ashish Gupta spent 20 years in finance — investment banking, hedge funds, venture — before pivoting into social impact and edtech. Now, he’s helping millions of children learn to read in both English & Spanish through Amira Learning. But getting there meant letting go of a comfortable path, redefinin...

What do you do when you don’t know what you want to be? If you’re Matt McDonnell, you grab a duffel bag, live on sailboats, study law, launch startups, and raise capital — all while chasing curiosity instead of credentials. Matt’s journey is anything but linear. From backpacking in the Adirondacks to pitching investors in Austin, he’s built a life on the belief that you don’t have to follow the ru...

In this episode, we sit down with Holly Tachovsky, a serial entrepreneur who built and sold multiple tech companies, including BuildFax. Holly shares how early rejections, survival-mode decisions, and unexpected insights (like the billion-dollar secret behind “roof age”) helped shape her success. We talk about: How to build a business without a business degree Why mistakes are the best teachers Ho...

In this episode, we talk with Samantha Jansky—co-founder and Head of School at Ascent Academy —about building a new kind of education. Samantha shares how her own mentorship journey shaped her work today, from studying political science to launching a learner-driven school where kids create business plans by age six and set their own goals daily. We dive into entrepreneurship education, parenting...

Season 4 of Uncharted Your Sidekick for Life  launches with Jeff Davidson—entrepreneur, mentor, and Co-Founder of Camp Gladiator, one of the fastest-growing fitness companies in the U.S., built after Jeff’s wife Ally competed on NBC’s American Gladiators. Jeff shares the early wins, the tough lessons (including a pair of matching Corvettes), and the resilience it takes to build something real. Tog...

In our Season 3 finale, we sit down with Andrew Tull—tech entrepreneur, connector, and passionate mentor—for a conversation about aligning your life with purpose. From founding global ventures to curating intimate “gatherings of friends,” Andrew shares why giving back, listening deeply, and choosing your board of advisors with intention can transform your path. We also talk about starting business...

David Christie joins the Uncharted Your Sidekick for Life crew to explore the deep connection between storytelling and human growth. From listening to John Maxwell tapes as a teenager to becoming a mentor and speaker himself, David shares how his journey was shaped by intentional mentors, emotional breakthroughs, and a relentless curiosity to grow. In this conversation, we talk about: Why storytel...

In Episode 10, Dan, Natalie and Gloria sit down with Paige Velasquez Budde—CEO of Zilker Media—for an honest, insightful conversation about modern leadership, the power of mentorship, and why your digital first impression matters more than ever. From her early days as a touring teen musician to co-founding a purpose-driven marketing agency, Paige’s journey is a masterclass in owning your narrative...

In Episode 9, Dan, Natalie and Gloria are joined by JP Newman, CEO of Thrive FP and host of Investing on Purpose . JP brings a refreshing take on entrepreneurship, mentorship, and what it means to build with intention. From hustling as a kid in LA to navigating a whirlwind career in Hollywood—and growing a $2B real estate portfolio, JP’s story is full of unexpected twists—and deep lessons. He shar...

In Episode 8, Dan and Natalie sit down with Matthew Thomas , a seasoned entrepreneur, investor, and mentor who helps early-stage companies scale through Entrepreneurs’ Organization (EO) and peer-to-peer mentorship . Matthew shares his journey from a small-town Oklahoma kid with a dream of attending the Air Force Academy to becoming a business leader . He talks about the mentors who changed his lif...