Uncharted

Uncharted
  • 5.0 (12)
  • BUSINESS
  • UPDATED WEEKLY

Grow your business with advice from the best. Uncharted is a private collective of top-tier founders, funders, and creators — and on this podcast, our members share the unseen tactics and strategies that drive their success. It’s like you’re sitting next to them at an Uncharted event.

  1. Achieve More Without Burning Out, with Global Expert Dr. Taryn Marie Stejskal

    MAR 4

    Achieve More Without Burning Out, with Global Expert Dr. Taryn Marie Stejskal

    Burnout is the greatest danger to any ambitious founder. But with the right strategies, you can drive hard, grow fast, and preserve your sanity. Dr. Taryn Marie Stejskal explains how. She’s the founder of the Resilience Leadership Institute, was previously head of executive leadership development & talent strategy at Nike, and a recognized expert on resilience and burnout.

    53 min
  2. Tim Draper, VC Legend

    04/10/2025

    Tim Draper, VC Legend

    Tim Draper graciously joined us while traveling, so we appreciate your patience with any audio variances during the conversation. In this episode of Uncharted, legendary venture capitalist Tim Draper joins for a wide-ranging conversation that’s part masterclass, part manifesto. From backing 20+ unicorns and buying Bitcoin when no one else would, to founding Draper University and creating a global pitch show, Draper unpacks his philosophy, his aversion to bureaucracy, and why trust and freedom are the bedrock of innovation. He shares war stories from early DFJ days, reflects on the rise and fall of China’s entrepreneurial boom, and dishes out advice on where the smart money should go next. Fly-Flat.com/Uncharted for $250 off your eligible long-haul, international, business and first class flight FlyFlat reclaims up to 90% of their customers’ time on booking international premium travel via their 24/7 white-glove concierge service. They average 35% off long-haul, international, business and first-class flights, and offer savings as high as 80% off for one-ways and last-minute flights.

    55 min
  3. Kevin Lavelle, Harbor

    03/06/2025

    Kevin Lavelle, Harbor

    In this episode, we sit down with Kevin Lavelle, founder of Mizzen+Main and now the visionary behind Harbor, a company reinventing baby sleep technology. Kevin shares his raw, unfiltered journey of building a multi-million dollar menswear brand from the ground up, the highs and lows of startup life, and what led him to leave it all behind to tackle an entirely new industry. He opens up about the early struggles of entrepreneurship—maxing out credit cards, going years without a salary, and navigating the emotional toll of building a business. Now, with Harbor, Kevin is taking another bold swing, challenging the status quo in the baby monitor industry and introducing a first-of-its-kind remote night nanny service. He reflects on his fundraising struggles, the lessons learned from venture capital roadblocks, and why resilience and conviction matter more than ever. Fly-Flat.com/Uncharted for $250 off your eligible long-haul, international, business and first class flight FlyFlat reclaims up to 90% of their customers’ time on booking international premium travel via their 24/7 white-glove concierge service. They average 35% off long-haul, international, business and first-class flights, and offer savings as high as 80% off for one-ways and last-minute flights.

    44 min
  4. Hailey Swartz, Actual Veggies

    02/20/2025

    Hailey Swartz, Actual Veggies

    In this episode of The Uncharted Podcast, we sit down with Hailey Swartz, co-founder of Actual Veggies, the brand behind what many call the best veggie burger on the market. With over $12 million in revenue and 6,000 retail doors, Hailey shares how she built a category-defining brand in a crowded and competitive CPG landscape. We dive into the state of the vegetarian market, the unexpected lessons from launching during COVID, and how Hailey and her team hacked their way into retail with bold strategies and scrappy execution—including their unexpected launch on QVC. Hailey also opens up about the highs and lows of fundraising, the realities of scaling in grocery, and why staying disciplined and lean is the key to survival in the ever-changing world of CPG. Fly-Flat.com/Uncharted for $250 off your eligible long-haul, international, business and first class flight FlyFlat reclaims up to 90% of their customers’ time on booking international premium travel via their 24/7 white-glove concierge service. They average 35% off long-haul, international, business and first-class flights, and offer savings as high as 80% off for one-ways and last-minute flights.

    28 min
  5. Zach Resnick, FlyFlat

    02/06/2025

    Zach Resnick, FlyFlat

    In this episode of Uncharted, we dive into the hidden mechanics of the airline and points industry with Zach Resnick, founder of Fly Flat. Zach reveals the intricate world of airline loyalty programs, the financial alchemy behind mileage programs, and how airlines function more like fintech companies than transportation businesses. From credit card hacking in college to building a thriving business that helps executives and entrepreneurs fly first-class for less, Zach shares his journey and the insider secrets that make his company the go-to concierge for premium travel. Whether you’re a frequent flyer or just fascinated by the economics of air travel, this episode unpacks the hidden strategies that keep airlines afloat. FlyFlat reclaims up to 90% of their customers’ time on booking international premium travel via their 24/7 white-glove concierge service. They average 35% off long-haul, international, business and first-class flights, and offer savings as high as 80% off for one-ways and last-minute flights. Deals.Fly-Flat.com Get the latest deals from your home airport delivered to your inbox weekly. All FlyFlat Newsletter Deals are at least 50% off. Fly-Flat.com/Uncharted for $250 off your eligible long-haul, international, business and first class flight.

    46 min
  6. Katie Shea, Venture Capitalist

    01/23/2025

    Katie Shea, Venture Capitalist

    Katie, a venture capitalist, discusses her journey from founding a ballet flat startup to angel investing and now running her own fund, Divergent. She emphasizes the importance of early-stage investments, noting that her fund’s 30 million USD focuses on pre-seed deals at sub-10 million valuations. Katie highlights the significance of maintaining a small fund size, avoiding dilution, and building trust with limited partners (LPs). She also touches on the challenges of raising a fund during COVID-19 and the strategic decision to avoid follow-on investments. Katie’s approach is rooted in deep relationships and a focus on sectors like supply chain, healthcare, and marketplaces.

    34 min
  7. Uncharted Season 2 Premiere: A Conversation with Michael Loeb

    01/06/2025

    Uncharted Season 2 Premiere: A Conversation with Michael Loeb

    In the highly anticipated return of the Uncharted Podcast, we kick off Season 2 with a dynamic conversation featuring Michael Loeb, renowned entrepreneur and founder of Loeb.nyc. We delve into the transformative year since our last discussion, the current economic and political landscape, and the exciting future for Uncharted. This episode unpacks key insights into: The evolution of venture capital amidst fluctuating markets. Overhyped trends like AI and their real-world implications for startups. The critical role of entrepreneurship in innovation, job creation, and societal impact. Listeners will also get an insider’s look at the Uncharted ecosystem, a space where top entrepreneurs, founders, and creatives converge to collaborate and inspire. Michael shares heartfelt reflections on his vision for Uncharted, emphasizing the importance of advocacy, community, and fostering connections that lead to transformative partnerships. Whether you’re a seasoned entrepreneur or simply curious about the driving forces behind industry disruptors, this episode is packed with thought-provoking moments, actionable insights, and stories of perseverance. Download transcript

    33 min
  8. Tracy Holland, Founder, Investor, Executive Chairman, and Entrepreneur

    09/13/2023

    Tracy Holland, Founder, Investor, Executive Chairman, and Entrepreneur

    Tracy Holland is a founder, investor, Executive Chairman, and entrepreneur who is an authority on beauty and wellness with a global track record of incubating and launching brands. Tracy co-founded the HATCHBEAUTY brand incubator in 2009 and has since led highly successful development strategies and launches for popular brands including: Naturewell by Jewel, Nuance by Salma Hayek, BLISS color, FOUND Active, and Orlando Pita Haircare.

    1h 6m
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5
out of 5
12 Ratings

About

Grow your business with advice from the best. Uncharted is a private collective of top-tier founders, funders, and creators — and on this podcast, our members share the unseen tactics and strategies that drive their success. It’s like you’re sitting next to them at an Uncharted event.

Information

  • Creator
    Uncharted
  • Years Active
    2023 - 2026
  • Episodes
    23
  • Rating
    Clean
  • Copyright
    © Uncharted
  • Show Website
    Uncharted