Latest Episode
1605: From Art Director to Tech CEO: The Power of Solving Your Own Problem w/ Rayne Chapman
Rayne Chapman, a creative director turned tech founder, joins the show to share how she transformed a personal frustration—the lack of a good way to save online inspiration—into a thriving business called Neat. This episode is a masterclass in building a product with deep intentionality, driven by genuine user needs rather than just adding features for the sake of it. For any entrepreneur or wantrepreneur, this conversation is packed with insights on how to leverage your unique background, use c
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1605
Oct. 28, 2026
1605: From Art Director to Tech CEO: The Power of Solving Your Own Problem w/ Rayne Chapman
Rayne Chapman, a creative director turned tech founder, joins the show to share how she transformed a personal frustration—the lack of a good way to save online inspiration—into a thriving business called Neat. This episode is a masterclass in building a product with deep intentionality, driven by genuine user needs rather than just adding features for the sake of it. For any entrepreneur or wantrepreneur, this conversation is packed with insights on how to leverage your unique background, use c
1604
Oct. 27, 2026
1604: This AI Assistant Knows Your Team Better Than You Do w/ Masumi Nakamura
In a world buzzing with AI advancements, Masumi Nakamura is focused on the one thing technology often overlooks: the people. After 25 years as a top engineering leader at giants like Cisco and PayPal, Masumi realized the biggest challenges weren't in the code, but in the complex human dynamics of a team. In this episode, he introduces askMyu, his private AI assistant designed to navigate the "people side" of work. This isn't about replacing jobs; it's about enhancing our most human skills. For a
1603
Oct. 26, 2026
1603: Are You in the Weeds? How to Think Strategically + One Level Higher w/ Mark McSweeney
Mark McSweeney, a 30-year veteran of the association and nonprofit world, shares powerful insights on governance, strategy, and leadership that apply to any business. He reveals the universal patterns of success he's observed across countless organizations and breaks down why even the most unique businesses face similar challenges. This episode is a masterclass in strategic thinking, teaching you how to get out of the "weeds," facilitate better conversations, and ask the kind of questions that l
1602
Oct. 25, 2026
1602: You'll get PUNISHED as the FINISHER... (AI took this episode over!)
Every entrepreneur loves the superhero story: the founder who swoops in at midnight to fix the crashed server, write the perfect sales copy, and hold the whole business together. But what if that superhero is actually trapped in a cage built from their own competence? In this special Solo Sunday, Brian is unplugged and spending time with his family, so two AI hosts take over the feed. Nobody on Brian’s team prompted or directed them. They chose to turn the microphone around and dissect Brian’s o
1601
Oct. 23, 2026
1601: Just when you think it FLOPPED, here's how it can work out... (COLLAB EPISODE!)
In this special Collab Week episode of Wantrepreneur to Entrepreneur, 8 founders come together to answer one deceptively powerful question: Think back to a flop or failure you’ve had in your business. How did it end up feeding something that worked? This episode covers ad campaigns that flopped, teams scaled too fast, AI projects that got ahead of the technology, a contractor who never delivered, an expo full of the wrong audience, a deal lost on the two-yard line, and a lot more. Together, th
1600
Oct. 22, 2026
1600: From Army Officer to AI Founder: A Masterclass in Mission-Driven Entrepreneurship w/ Nils Olsen
Nils Olsen, a former Airborne Infantry Officer, is rewriting the rules of defense technology with his AI-powered startup, Six Tango. In this episode, Nils shares his incredible journey from the front lines to founder, revealing how he took a problem he experienced firsthand in the military and turned it into a groundbreaking business. He unpacks the "Moneyball for the military" strategy, showing how data can uncover hidden opportunities in any industry. This episode is a must-listen for any entr
Recent Blog Posts
Oct. 28, 2026
Envisioning the Future: How Mark McSweeney Redefines Strategic Planning
Mark McSweeney's journey from wantrepreneur to entrepreneur is a testament to the power of intentional leadership. With over 30 years as an association executive, Mark founded Envisioned Future to help nonprofits harness their collective talent thro…
Oct. 27, 2026
How John Lee Turns AI Content Into Income: His Social Media Monetization Strategy
Imagine creating a five-minute AI video that attracts 1.2 million views and generates more than 4,000 leads for your business. Now imagine that video doesn't feature you. It doesn't feature an employee, an influencer, or even a real person. It fea…
Oct. 26, 2026
Beyond the Glass: Jack Defay's Strategy for Interactive Museum Experiences
From scanning ancient artifacts to creating immersive museum experiences, Jack Defay's journey is a masterclass in innovation and accessibility. As the founder of Museum Scan, Jack transforms static exhibits into interactive, multisensory adventures…