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The Wantrepreneur to Entrepreneur Podcast
Latest Episode

1409: Solving a Broken System: The Origin Story of Heirloom, the “TurboTax for Probate” w/ Davis Wilkinson

Davis Wilkinson, co-founder of Heirloom, shares the deeply personal story of how watching his mother navigate the estate settlement process after his brother’s passing inspired him to leave big tech and build a solution. This...

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1409: Solving a Broken System: The Origin Story of Heirloom, the “TurboTax for Probate” w/ Davis Wilkinson
March 13, 2026

1409: Solving a Broken System: The Origin Story of Heirloom, the “TurboTax for Probate” w/ Davis Wilkinson

Davis Wilkinson, co-founder of Heirloom, shares the deeply personal story of how watching his mother navigate the estate settlement process after his brother’s passing inspired him to leave big tech and build a solution. This...
Listen to the Episode
1408: This NASDAQ CEO’s Secret to Staying Power in a World of Shiny Objects w/ Jolie Kahn
March 12, 2026

1408: This NASDAQ CEO’s Secret to Staying Power in a World of Shiny Objects w/ Jolie Kahn

In this powerhouse episode, we sit down with Jolie Kahn, the CEO of NASDAQ-listed AVAX One, who masterfully bridges the worlds of traditional finance, corporate law, and the cutting edge of cryptocurrency. Jolie shares the en...
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1407: Lead People, Manage Resources: The Simple Rule That Changes Everything w/ Abrahm DiMarco
March 11, 2026

1407: Lead People, Manage Resources: The Simple Rule That Changes Everything w/ Abrahm DiMarco

Ever feel like you weren't "born" to be a leader? This episode will change your mind. We sit down with Abrahm DiMarco, a West Point graduate and 20+ year Army veteran who has turned a lifetime of high-stakes leadership experi...
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1406: The AI Revolution Is Offline: Why Your Laptop Is More Powerful Than The Cloud w/ Josh Hipps
March 10, 2026

1406: The AI Revolution Is Offline: Why Your Laptop Is More Powerful Than The Cloud w/ Josh Hipps

In a world obsessed with cloud-based everything, Josh Hipps is pioneering a different path: the "sovereign AI" revolution. Josh, the founder and CEO of Neutron Tech, shares his incredible journey from the Air Force Academy an...
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1405: Quitting A 6-Figure Tech Job Looks Crazy On Paper, But Here’s Why He Did It w/ Isaiah Centifanto
March 9, 2026

1405: Quitting A 6-Figure Tech Job Looks Crazy On Paper, But Here’s Why He Did It w/ Isaiah Centifanto

Isaiah Centifanto is the ultimate example of an entrepreneur driven by curiosity and a desire to help others. He takes us on his incredible journey from a small town in Montana to the Air Force, to becoming a cloud architect ...
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1404: You get to choose...
March 8, 2026

1404: You get to choose...

Ever find yourself caught in a loop of "Is this even going to work?" It's a question every founder asks, from day one to year ten. In this Solo Sunday episode, Brian gets vulnerable and pulls back the curtain on the most impo...
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Recent Blog Posts

How Alex Cooper Built a $100M+ Media Empire Beyond Call Her Daddy
March 14, 2026

How Alex Cooper Built a $100M+ Media Empire Beyond Call Her Daddy

When most people think about Alex Cooper, they think about Call Her Daddy — the wildly popular podcast that became one of the most recognizable brands in modern media.But what many people don’t see is the CEO behind the microphone.Be…

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The Privacy Game-Changer: Shikha Soneji on Making Digital Consent Understandable
March 13, 2026

The Privacy Game-Changer: Shikha Soneji on Making Digital Consent Und…

Shikha Soneji’s journey from academic researcher to AI innovator is a testament to resilience and vision. As the founder of ConsenTerra, she’s reshaping how we understand digital consent, bridging the gap between complex legal jargon and…

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Amjad Masad’s Radical Bet: A $1B Company Built by One Person Is Closer Than You Think
March 12, 2026

Amjad Masad’s Radical Bet: A $1B Company Built by One Person Is Close…

In an interview on Silicon Valley Girl, Replit founder and CEO Amjad Masad made a prediction that would have sounded absurd just five years ago:“In the next few years.”That’s his answer to when a solopreneur could build a b…

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Reviews

Fabulous podcast

"If ever I need a pep talk and a quick pick me up I can count on Brian. He’s so personable and his energy is so catchy. He shares a wealth of information. Love this!"

KDBabs | March 12, 2022

Amazing podcast!

"This podcast is awesome!! I am just about to start my business, and this podcast has been giving me the motivation, inspiration, confidence, and tools to move ahead. Brian is fun and engaging and pre…"

laurjf | Dec. 23, 2021

No nonsense and straight to the point!

"Whenever I need a burst of motivation or clear direction on how to grow my business, Brian always delivers. I can’t decide on which weekly episode is my favorite... the fact that episodes are varied …"

jennis2021 | Feb. 24, 2021
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