Rogue Wealth

Nobody warns you that deal fatigue is a weapon. After eight months of due diligence, document requests, management presentations, and timeline extensions — the buyer comes back with adjustments. The headline number is down. The earnout expanded. The working capital peg moved against you. Most founders take it. Not because they're weak — because they're exhausted. And that exhaustion was engineered...

Most family businesses don’t have a purpose problem. They have an execution problem. In this episode of Rogue Wealth , Kris Garlewicz takes aim at one of the most celebrated ideas in modern business culture: Start With Why. Because in family businesses, the “WHY” is rarely the issue. Legacy, pride, stewardship, generational impact — most founders already know exactly why they do what they do. What...

75% of business owners regret selling their company — and it’s not because of the money. In the latest installment of Rogue Wealth , Kris breaks down why exits often lead to identity loss, purpose vacuum, and family disruption — and what the 25% who thrive do differently. Know what you're running toward before you run from what you've built. If you’re thinking about selling, this episode is requir...

Most entrepreneurs believe clarity comes first. It doesn’t. In this episode of Rogue Wealth , Kris sits down with Paul Rosenthal, Managing Partner at IHC, to unpack one of the most dangerous myths in business: the belief that you need perfect clarity before you act. Paul’s story doesn’t start in a boardroom. It starts in a garage 15 years ago. What followed wasn’t a perfectly mapped blueprint — it...

Most business owners focus on revenue, growth, and operations. Very few focus on the paper. And that’s where enterprise value is either protected… or quietly destroyed. In Episode 6 of Rogue Wealth , Kris Garlewicz sits down with Emily Stubbs, Director of Legal Solutions at Visibility CFO & Tax Advisors, to explore how legal precision and tax strategy work together to build real, durable enter...

Most families believe they’re prepared for a crisis. They’ve signed the documents. Checked the boxes. Completed the estate plan. And yet, almost none of them are ready for the disaster that actually comes first. In this episode of Rogue Wealth , Kris dismantles the dangerous myth that death is the real emergency. The true crisis is the three to seven year marathon before it — cognitive decline, lo...

In this hard-hitting episode of Rogue Wealth , Kris Garlewicz tears apart one of the biggest myths in family business: “The tax code is designed to take your money.” Wrong. It’s designed to reward specific behaviors — and family businesses are the single most advantaged group in the entire system. Kris breaks down how the tax code actually works, why your CPA is probably costing you more than they...

A struggling family business isn’t always a product of circumstance—it’s often a reflection of choice. In this episode, Kris Garlewicz breaks down The Family Business Performance Hierarchy —a five-tier framework that helps you diagnose exactly where your organization stands today… and what it takes to climb higher. From “Obsolete” operations to “Apex” performance, Kris explores the mindset, leader...

In this episode of Rogue Wealth, host Kris Garlewicz tackles one of the most destructive—and least discussed—forces in family business: emotional friction. Building on Episode 1’s theme of Blocking Out the Noise, this conversation exposes the emotional tax that quietly drains productivity, clarity, and growth. The toughest consultant your business will ever face isn’t a Wall Street analyst—it’s of...

Welcome to the inaugural episode of Rogue Wealth , the podcast built for leaders, entrepreneurs, and family business owners who are serious about building and protecting real wealth. In this first conversation, we’re diving into one of the single biggest wealth killers of our time: noise . From market updates, social feeds, and endless “productivity hacks,” the constant barrage of information is d...