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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
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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
1599
Oct. 21, 2026
1599: The End of Copy-Paste: The Future of AI in Business w/ Curtis Boortz
Overwhelmed by a daily flood of 100+ emails, Curtis Boortz decided to solve his own problem by building a custom AI tool. That tool evolved into ForthWrite, an AI platform that drafts emails in your authentic voice, directly within your inbox. In this episode, Curtis shares his incredible journey from finance professional to solo tech founder, revealing how he transformed a personal pain point into a scalable SaaS business. This episode is a masterclass for any entrepreneur looking to leverage A
1598
Oct. 20, 2026
1598: Rewire Your Business: How to Stop Escalating and Start Executing w/ Rachel Honoway
Are you tired of feeling like your team is constantly distracted, solving the same problems over and over? In this powerful episode, former C-suite executive Rachel Honoway reveals how to break the cycle of "creative avoidance" and rewire your organization for true alignment and explosive growth. She shares why most leadership teams aren't nearly as aligned as they think and provides a simple exercise to expose the gaps immediately. For any wantrepreneur or entrepreneur who wants their team to m
1597
Oct. 19, 2026
1597: Beyond Mindset: The Nervous System Secret to Entrepreneurial Growth w/ Shervon Laurice
Feeling stuck, burned out, or hitting the same revenue wall year after year? This episode is your permission slip to stop searching for the next "perfect" strategy. We sit down with Shervon Laurice, a licensed psychotherapist and transformational coach who reveals why your biggest business breakthroughs have nothing to do with your marketing plan or sales funnel. She explains that real, sustainable growth comes from developing your inner world—regulating your nervous system, consciously shaping
1596
Oct. 18, 2026
1596: Every time I do this, I make more money (even though it's SIMPLE and BORING!)
As Q4 kicks into high gear, the pressure is on to launch new products, create flashy promos, and find new customers to finish the year strong. But what if your biggest opportunities aren't in what’s new, but in what’s old? In this Solo Sunday episode, Brian shares his all-time favorite, most effective, and deceptively simple strategy for generating massive momentum: the reactivation campaign. Forget overcomplicating things. Brian breaks down why reaching out to past prospects—even the ones who g
1595
Oct. 16, 2026
1595: How do you get through LEAN SEASONS in business? (COLLAB EPISODE)
In this special Collab Week episode of Wantrepreneur to Entrepreneur, eight founders come together to answer one deeply honest question: Take us back to a lean season in your business. How did you get through it, and how do you prepare differently now? Some are in a lean season right now. Some are still learning from their first one. Others have watched their busy seasons and slow seasons flip on them. It’s a wide-ranging episode about relationships, pipelines, cash, self-care, and why the best
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Oct. 22, 2026
The Hidden Cost of Winning: What Ray Dalio and Toto Wolff Teach Us About Leadership, Failure, and Success
What happens when one of the world's most accomplished investors sits down with one of Formula 1's most successful team leaders? A surprisingly vulnerable conversation about failure, self-awareness, and what it really takes to build something extrao…
Oct. 21, 2026
Sparking Creativity: Rayne Chapman on Turning Inspiration into Action
Rayne Chapman transformed her creative chaos into Neat, a dedicated library that empowers creators to turn inspiration into reality. In this Wantrepreneur to Entrepreneur Spotlight, Rayne shares how her journey from Meta to entrepreneurship was fuel…
Oct. 20, 2026
Lovable Co-Founder Anton Osika: How to Build a Profitable AI Business Without Coding
What if the biggest obstacle to starting a business wasn't your technical ability anymore, but your ability to recognize a problem worth solving? For decades, aspiring entrepreneurs faced an uncomfortable reality: having a great software idea was r…