Breaking the Barrier

Rob Hays sits down with Nick Madden to break down what it takes to lead when everything is on fire. Rob took over as CEO of the publicly traded Ashford Hospitality Trust in April 2020 — and within a weekend furloughed 93% of nearly 13,000 associates, ran 700-room hotels with three people, watched revenue fall almost 100% in two months, and defaulted on $4.5B of mortgages across roughly 130 hotels....

Scott Weeman sits down with Nick Madden to break down the addictions that quietly come with ambition — pride, control, and money — and the honesty it takes to name them. Scott is the Executive Director of Catholic in Recovery, the national nonprofit he built over the last decade around a combination of the 12 steps and the sacraments. He explains why “no one enters recovery on a winning streak,” h...

David Niccolini sits down with Nick Madden to explore a side of business few founders never see. After being invited to a founder table that included former Secret Service and U.S. Senate security leaders, David co-founded Torchstone — a risk-mitigation firm that's hit the Inc. 5000 multiple times — and later co-founded Evidentity, a data company that traced forced labor through global supply...

Nick Madden sits down with Rob Kaczmark to discuss the unexpected journey from getting fired from Catholic radio to building Spirit Juice Studios — a media company that now generates over 1 BILLION views and produces thousands of videos every year. Rob shares the behind-the-scenes story of the early failures, financial sacrifices, creative risks, and leadership lessons that shaped the company over...

Professional burnout is often the result of a lack of structural discipline rather than a heavy workload. In this episode, Nick Madden and Jeremy Aranda introduce the "3:30 Stop" challenge , a practical exercise in time-blocking that forces leaders to end meetings early to review the day and plan for the next. By creating this strategic margin, executives can transition from high-intensity work to...

Jeff sits down with Nick Madden to break down why culture and strategy are not separate things, the 7-question filter he uses before committing to any business opportunity, and what backward planning from a 3-year vision actually looks like in practice. Jeff draws from his experience helping lead an energy consulting firm through a turnaround that ended in a $300M sale, co-founding Undivided Life,...

As co-founder of Presidio, the first pro-life health insurance company in America, Bob Hogan is building a values-aligned alternative in one of the most complex and regulated industries in the country. Bob sits down with Nick Madden to unpack 100+ failed pitches, constant course correction, and what it takes to execute under pressure when nothing goes to plan. ► JOIN THE MOVEMENT: #BESENT Learn Mo...

Flip Howard sits down with Nick Madden to break down what actually drives long-term business growth without overcomplicating it. Flip explains why taking action beats waiting for the perfect strategy, how the right people can transform or break a company, and why most entrepreneurs overthink instead of simply executing better than their competition. Flip draws from building Lucid Private Offices t...

Tim Lyons sits down with Nick Madden to break down what actually makes a leader effective when the stakes are high. Tim explains why every organization needs skeptics (and how to use them), how to build a set of “no-BS buddies” for real feedback, and why a “personal board of directors” might be the most underused tool in an entrepreneur’s life. Tim draws from decades at Haggar Clothing, including...

What does it actually look like to build a business without leaving your faith at the door? This is your first look at Breaking the Barrier , real conversations with proven entrepreneurs and founders on leadership, failure, and the practical wisdom behind building with conviction.