Uncharted

How do founders stay calm, think clearly, and find answers faster when everything goes wrong?In this episode, host Jason Feifer talks with Gambit Robotics cofounder and former U.S. chess player Nicole Maffeo about the real mechanics of problem solving. They break down how great operators handle ambiguity, why patience is now a competitive advantage, how to “chunk” complex problems into solvable parts, and why losing well may be one of the most valuable entrepreneurial skills.

If you’re thinking about a pivot, a new venture, or a move into unfamiliar territory, this conversation will give you a smarter way to think about starting from scratch.

In this episode, Jason Feifer talks with Michael Louis, cofounder and CEO of the AI company Cerebrium, about what it takes to win in spaces you’ve never worked in before. Michael has built companies across blockchain, e-commerce, and AI, and he explains how he approaches every new market: by invalidating ideas fast, solving the next problem instead of obsessing over the long-term plan, building highly autonomous teams, and using relationships to accelerate learning and growth.

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.

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.

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.

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.

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.

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Fly-Flat.com/Uncharted for $250 off your eligible long-haul, international, business and first class flight.

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.

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:

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.

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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.