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1556: This AI Founder Is Changing How You Get Dressed w/ Sebastian De Castro
Ever wonder how to take a personal passion and turn it into a high-tech, scalable business? Sebastian De Castro, founder of AI-powered personal stylist AskTailr, did just that, leaving a successful engineering career to solve a problem he was obsessed with. This episode is a masterclass in making the entrepreneurial leap, bootstrapping a startup with intention, and building a product that solves a real, recurring customer problem. Sebastian shares his methodical, evidence-based approach to produ
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1556
Sept. 1, 2026
1556: This AI Founder Is Changing How You Get Dressed w/ Sebastian De Castro
Ever wonder how to take a personal passion and turn it into a high-tech, scalable business? Sebastian De Castro, founder of AI-powered personal stylist AskTailr, did just that, leaving a successful engineering career to solve a problem he was obsessed with. This episode is a masterclass in making the entrepreneurial leap, bootstrapping a startup with intention, and building a product that solves a real, recurring customer problem. Sebastian shares his methodical, evidence-based approach to produ
1555
Aug. 31, 2026
1555: From $5 an Hour to an $82M Territory (And Why She Walked Away) w/ Digna Deleon-Morris
Digna Deleon-Morris shares her incredible journey from arriving in the U.S. from the Dominican Republic and earning $5.25 an hour, to climbing the corporate ladder and managing an $82 million territory, only to realize she was a "slave to corporate America." This episode is a masterclass in radical transformation, as Digna opens up about the 6-year internal battle to shift from an employee mindset to an entrepreneurial one, the devastating financial loss that forced her to learn how money really
1554
Aug. 30, 2026
1554: This is NOT a perfect podcast episode (something happened for the first time...)
Ever created something—a social media post, a proposal, an email—and hesitated to send it because it just wasn't "perfect"? This Solo Sunday, Brian pulls back the curtain on a first-time event in the show's 1,500+ episode history: a brilliant guest interview that will never see the light of day. In this transparent episode, Brian shares the story of why the episode was pulled and the profound lesson it sparked about perfectionism, impact, and the courage to "hit publish." This isn't just a story
1553
Aug. 28, 2026
1553: From Uber's AI Policy to Your Smart Home: The Future is Here w/ Dr. John Lunsford
Dr. John Lunsford, founder of Tethral and former AI leader at Uber, joins the show for a mind-bending conversation about the true frontier of artificial intelligence: our daily lives. John breaks down how the tech we’ve been promised for decades is finally here, moving beyond simple rules into complex, adaptive reasoning that can manage the "messiness" of human life. This episode is a masterclass for entrepreneurs on systems thinking, identifying billion-dollar opportunities in everyday problems
1552
Aug. 27, 2026
1552: The Minimally SELLABLE Product: Why Your MVP is No Longer Good Enough w/ Warren Johnson
If you’re an expert in your field with a game-changing software idea but no idea how to build it, this episode is your roadmap. We’re joined by Warren Johnson, the founder and co-CEO of Plexor Labs, who has cracked the code on turning domain expertise into market-ready products. Warren shares his incredible journey from a nearly two-decade career at Microsoft to becoming a substitute teacher and eventually graduating from Harvard with a master's in education, all of which shaped his unique appro
1551
Aug. 26, 2026
1551: The Hidden Data That Reveals a Leader's True Potential w/ Logan Yonavjak
Tired of making hiring decisions based on gut feelings and resumes that only tell half the story? This episode is your guide to a revolutionary new approach. We sit down with Logan Yonavjak, a two-time founder and CEO of The Readiness Engine, a company that's changing how we understand leadership. Logan breaks down the critical difference between "experience" (where someone has been) and "readiness" (where they can go). She reveals how her company uses AI and developmental psychology to analyze
Recent Blog Posts
Sept. 1, 2026
AriZona Iced Tea Founder Don Vultaggio’s Warning to Entrepreneurs: Know Your Costs Before You Raise Capital
There is a sentence from AriZona Beverage Company founder Don Vultaggio that cuts against much of modern startup culture: “The first can of Arizona I sold in 1992, I made a profit on.” And he didn’t stop there. “The last can I’m going to sell…
Aug. 30, 2026
Emma Chamberlain on Building Chamberlain Coffee, Trusting Her Gut, and Knowing When to Walk Away
Emma Chamberlain built her career by knowing when something no longer felt right. At 16, that meant abandoning the polished YouTube style she initially tried to imitate and making videos that actually sounded like her. Years later, it meant steppin…
Aug. 29, 2026
Seth Godin on the Psychology of Marketing: Stop Chasing Attention and Start Creating Change
For decades, Seth Godin has challenged entrepreneurs to rethink what marketing actually means. Not advertising. Not hype. Not interrupting strangers until enough of them finally pay attention. In a conversation with Dr. Michael Gervais on the Find…