Latest Episode
1607: How have you put your entrepreneurial GHOSTS to rest!? (COLLAB EPISODE!)
In this special Collab Week episode of Wantrepreneur to Entrepreneur, 10 founders come together to answer one deeply personal question:
Tell us about a decision or mistake that haunted you, and how you finally put that ghost to rest.
The ghosts in this episode include a strategy deck that walked out the door, funding turned down at the finish line, a six-figure funnel kept running out of attachment, and friendships that made hard calls even harder. It’s a wide-ranging, refreshingly honest episo
Recent Episodes
1607
Oct. 30, 2026
1607: How have you put your entrepreneurial GHOSTS to rest!? (COLLAB EPISODE!)
In this special Collab Week episode of Wantrepreneur to Entrepreneur, 10 founders come together to answer one deeply personal question: Tell us about a decision or mistake that haunted you, and how you finally put that ghost to rest. The ghosts in this episode include a strategy deck that walked out the door, funding turned down at the finish line, a six-figure funnel kept running out of attachment, and friendships that made hard calls even harder. It’s a wide-ranging, refreshingly honest episo
1606
Oct. 29, 2026
1606: This Educator-Turned-Founder is Saving Critical Thinking w/ Jordan Wolff
In a world grappling with the rise of AI, how do we protect the invaluable human skills of critical thinking, creativity, and authenticity? Jordan Wolff, a former educator turned founder, is tackling this challenge head-on. In this episode, Jordan shares his journey from the classroom to launching Typed by Hand, an EdTech company designed to champion authentic student work, not police it. This isn't just a conversation about education; it's a masterclass in building a purpose-driven, bootstrappe
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
Recent Blog Posts
Oct. 29, 2026
How RAYE Escaped Her Record Deal and Built a Superstar Career on Her Own Terms
Imagine spending years building something you believe in, only to have the people funding your dream repeatedly tell you it isn't good enough. Now imagine walking away from those people, taking your work with you, and building something bigger than…
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…