

Dialectic
Jackson Dahl
Conversational portraits of original people, across technology, media, business, and creativity. By Jackson Dahl.
Episodes
Mentioned books

79 snips
Nov 17, 2025 • 2h 22min
33. TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler
John Coogan and Jordi Hays share insights as the creative minds behind TBPN. They dive into their journey from a tech-focused duo to a media powerhouse. Discussing how they thrive in an era of competition, they emphasize the importance of high-volume production and constant iteration. They borrow innovative ideas from outside tech, like sports and Hollywood, to keep content fresh. The duo also reflects on their partnership dynamics, targeting a niche audience, and the significance of advertising for quality media.

151 snips
Nov 5, 2025 • 2h 36min
32: Chris Sacca - Drifting Back to Real
Chris Sacca, an influential investor known for his early stakes in Twitter and Uber, dives into the world of climate tech with Lowercarbon Capital. He reflects on a transformative coast-to-coast bike trip and the meditative focus it brought him. Sacca emphasizes the value of weird founders, practical storytelling, and how risk often gets mispriced in venture capital. He discusses the necessity of honest feedback and how a non-sycophantic culture at Lowercarbon promotes innovation. Finally, he shares the existential excitement and fears surrounding AI.

85 snips
Oct 15, 2025 • 2h 4min
31: Gabe Whaley - Playing the Crowd & Outlasting the Hype
Gabe Whaley, co-founder and CEO of MSCHF, shares his journey from BuzzFeed intern to leading a viral creative powerhouse. He discusses how MSCHF's 'black box' approach adds mystery and value to their projects. The conversation dives into the complexities of audience engagement, the art of remixing culture, and the shift in meaning of wearable objects like the Big Red Boot. Gabe reflects on rediscovering creative euphoria beyond virality and highlights the importance of smaller audiences for lasting cultural impact.

336 snips
Sep 30, 2025 • 2h 17min
30: David Senra - The Clarity of Commitment
David Senra, a passionate podcaster and host of Founders, dives into the power of storytelling and how it shapes entrepreneurship. He discusses the importance of concise content, the emotional drivers behind founders, and the value of biographies as practical guides. Senra emphasizes commitment over introspection, advocating for relentless focus on one's craft and the art of clear communication. With insights on creating high-value episodes and the significance of service in podcasting, his energetic approach inspires listeners to embrace their entrepreneurial journeys.

199 snips
Sep 10, 2025 • 2h 21min
29: Billy Oppenheimer - Attuned to Clues
Billy Oppenheimer, a researcher and writer collaborating with Ryan Holiday and Rick Rubin, shares insights into his creative process inspired by the concept of 'looking for clues.' He discusses building an external brain for ideas instead of relying solely on memory and emphasizes the significance of inputs over outputs. Oppenheimer dives into cultivating patience, navigating mainstream influences while maintaining authenticity, and valuing the creative journey over immediate success. This conversation offers valuable lessons on perseverance, creativity, and embracing the mundane.

82 snips
Sep 3, 2025 • 2h 19min
28: Maxwell Meyer - Starships & Road Trips
Maxwell Meyer is the founder of Arena Magazine and a key voice on American values, technology, and capitalism. He critiques media clichés, arguing for a bottom-up approach to national identity. The conversation highlights the American spirit of innovation, particularly in the context of space exploration. Meyer emphasizes the need for tech companies to align with traditional values while exploring the complexities of capitalism. With passionate anecdotes, he advocates for durability in consumer choices and the importance of both grand visions and everyday entrepreneurial narratives.

79 snips
Aug 28, 2025 • 1h 49min
27: Mackenzie Burnett - Accounting for the American Dream
Mackenzie Burnett, co-founder and CEO of Ambrook, is passionate about bridging the worlds of agriculture and technology. She shares her journey from a policy-focused background to building software for rural America. The conversation dives into the importance of independent businesses for the American Dream and the challenges of combining sustainability with profitability. Mackenzie discusses the intricacies of agricultural accounting and her commitment to developing user-friendly financial tools that empower small farms, showcasing her dedication to supporting local communities.

224 snips
Aug 20, 2025 • 1h 59min
26: Cyan Banister - A Fool’s Dérive
Cyan Banister, an investor and artist known for backing SpaceX and Uber, shares her unconventional journey from a childhood on a Navajo reservation to becoming a successful entrepreneur. She discusses the profound impact of music on community and personal growth and emphasizes the importance of mindfulness and self-discovery. Cyan's concept of 'dérive' encourages a playful, childlike approach to life, challenging perceptions and promoting personal accountability. She explores the balance of wonder and responsibility, inspiring listeners to embrace curiosity while navigating adult complexities.

66 snips
Aug 13, 2025 • 58min
25: Reggie James - Our Infinite Mirrors (Live at FWB Fest)
Reggie James, a designer and entrepreneur known for his work on Hardware 2024, shares his innovative perspectives on technology as a reflective mirror of our values. He discusses how friction in design can enhance meaning and the ties between technology and our software cultures. Reggie delves into the narratives shaping cryptocurrency and critiques the accessibility issues in tech. The conversation wraps up with reflections on personal myths, American idealism, and the vision needed for radical innovation that challenges the status quo.

157 snips
Aug 4, 2025 • 1h 49min
24: Linus Lee - Engineering for Aliveness
Linus Lee, a builder and engineer at Thrive Capital, delves into the intersection of technology and humanity. He discusses how software can enhance individual agency and the need for equitable access. A fascinating breakdown of instrumental versus engaged interfaces reveals the importance of design in user experience. Lee advocates for tools that foster creativity over mere mechanization, while also exploring the evolving nature of AI. His insights challenge us to consider whether technology will lead us to a more human or a less human future.


