Uncharted Your Sidekick for Life

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, redefining success, and learning to trust som...

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 rules to make something real.In this e...

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
  

• How real mentorship looks more...

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 for independence, what real mentorsh...

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. Together with his wife Ally, he success...

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 businesses, teaching kids about money, and ...

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 storytelling is critical in financial ser...
  

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. She shares how mentorship shaped h...

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 shares his Four Dimensional Wealth framew...

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 life, the lessons he learned from his care...

In Episode 7, Dan and Natalie sit down with Darlene Fiske, a PR and communications expert who helps luxury hospitality and wellness brands shape their stories and connect with audiences. As the founder of The Fiske Group and Swell, the Agency, Darlene has spent years mastering the art of storytelling, brand strategy, and media relations.

She shares her career journey from Yellowstone National Park to running a top PR agency, the po...

In Episode 6, Dan and Natalie sit down with JP Singh, an attorney, entrepreneur, and former neuroscience researcher, to talk about mentorship, career strategy, and how to create your own opportunities. From working with renowned neuroscientist David Eagleman to launching his own practice, JP shares how he used his three-step formula—add value, demonstrate competence, and ask for what you want—to carve his path to success. If you...

Join us for Episode 5 of Uncharted as we sit down with mother-daughter duo Laura Masters and Savannah Ringard for a powerful conversation on mentorship, personal growth, and forging your own path in life. Savannah shares her journey of stepping away from traditional education to travel the world, while Laura offers insight as both a mother and a mentor on the importance of trusting the process.

Savannah, also known as the "Austin Fa...

In founding_up's Uncharted Your Sidekick for Life Season 3, Episode 4, Dan, Natalie, and Leon sit down with Marcus Metzger, Executive Director of HICAM and lifelong “maker.” 

From building forts and coding websites as a kid to running a 15,000-square-foot creative incubator in NYC, Marcus shares how embracing curiosity, resilience, and mentorship shaped his journey. They dive into the power of hands-on learning, the importance of cr...

Season 3, Episode 3, with Tim Donohue—Through candid stories about failure, resilience, and mentorship, Tim highlights the importance of building a strong foundation of values like teamwork, discipline, and respect. He encourages young listeners to embrace failure as a learning opportunity and to stay curious and adaptable in the face of life’s transitions.

Tim also discusses the pivotal role mentorship has played in his life, both ...

In this inspiring episode of Uncharted: Your Sidekick for Life, we sit down with Rick Archer, co-founder of Overland Partners and a pioneer in designing spaces that transform lives. Rick shares his amazing journey—from his early love for art and architecture to pivotal moments of self-discovery and creating some of the most meaningful projects in the world. Whether it's the iconic Lady Bird Johnson Wildflower Center or centers ...

In this powerful kickoff to Season 3, we sit down with Jeremy Jenson, founder and CEO of Encore Search Partners a nationally renowned executive search firm. Jeremy shares his inspiring journey from humble beginnings to leading a multi-million-dollar business. Along the way, he reflects on the lessons he’s learned about failure, mentorship, and building a life of purpose. Whether you’re looking for entrepreneurial inspiration, insig...

In the Season 2 finale of Uncharted with Mike Millard, we sit down with Mike Millard—venture capitalist, mentor, and founder of Pitch-A-Kid—to explore the art of navigating challenges, embracing failure, and creating meaningful impact. Mike shares his journey from corporate strategy to venture capital, offering insights into the power of mentorship, building resilience, and thinking big. Whether you’re an aspiring entrepreneur or a...

In this episode of Uncharted: Your Sidekick for Life, we sit down with Hugh Forrest, Co-President and Chief Programming Officer of South by Southwest (SXSW), to explore his remarkable journey in shaping one of the world's most iconic festivals.

From SXSW's grassroots beginnings in Austin to its evolution as a global showcase of innovation, creativity, and collaboration, Hugh shares invaluable lessons on persistence, mentorship, and...