Rogue Wealth

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 required listening!Chapters:0:00 - Introduction1:05 - There's a 75% chance of misery in a year3:45 - You're just the guy that used to run a company7:30 - The "Exit to Greatness" Roadmap13:30 - The job of a Financial Bodyguard17:09 - Helping a client define their "next love"19:15 - Actions you can do right now!20:45 - Closing remarks

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 was execution. Decisions. Iteration. Expansion. While others were dividing a shrinking pie, Paul and his team focused on making the pie bigger — even in a commercial real estate market many had written off.Together, they explore:Why clarity is a byproduct of action — not a prerequisiteThe pressure of leading a family-run business without an operating manualThe entitlement vs. imposter syndrome tension that few talk about openlyHow ego quietly becomes the greatest liability in growing organizationsWhy comfort is often the most expensive phase of a business lifecycleThe financial value of time — and how to actually prioritize itThis conversation challenges the instinct to wait for certainty and instead makes the case for decisive movement. Because in business — and in legacy — execution creates the answers you’re waiting for.Rogue Wealth Rule #7: Ego is the liability.If you’re leading a family enterprise, building something from scratch, or navigating growth in uncertain markets, this episode is a reminder: momentum beats perfection.Chapters:0:00 - Introduction1:58 - "Don't dismiss the good energy when you know it"7:10 - Working without a user guide17:38 - Intuition and experience are what matter most28:40 - The imposter syndrome37:37 - Capturing operational systems properly47:10 - Advice to your former self54:53 - Stop looking for clarity. Decide and do!59:20 - Closing remarks

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 enterprise value.They revisit the philosophy behind “Visibility” — why clarity inside your numbers, agreements, and structure creates optionality long before a sale ever happens.This conversation dives into:Why 100% bonus depreciation being permanent changes capital planning strategyThe real risks and leverage behind taking equity in lieu of paymentWhat private equity firms actually look for in founder-led businessesWhy noncompete language after a sale can define (or restrict) your next chapterThe power of multidisciplinary collaboration between legal, tax, and advisory professionalsKris reinforces Rogue Wealth Rule #6: “If you don’t understand the paper, the paper owns you.”This episode is about thinking ahead. About having the occasional conversations more often. About ensuring your advisors stay strategic — not just friendly. Because enterprise value isn’t built at closing. It’s built in preparation.Learn more about Emily Stubbs and her team at Visibility CFO and Tax Advisors: https://www.visibilitycpa.com/Chapters:0:00 - Introduction1:20 - The common roadblocks hitting business owners4:22 - Private equity is looking for this10:40 - Rogue Wealth Rule #616:23 - Taking equity in lieu of payment21:22 - Non-competes and post-sale realities27:15 - The emotionally misjudged moments30:20 - Closing remarks

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, long-term care, caregiver burnout, family conflict, and financial hemorrhaging — all unfolding while the person you love is still alive and decisions still have to be made.This is the episode your advisory team never mentioned.We explore why families don’t “rise to the occasion” in emergencies, why the government’s default plan creates chaos, and why most estate documents fail when incapacity lasts years instead of weeks. From the hidden toll of caregiving to the devastating impact on family businesses, this conversation reframes preparedness as protection — not pessimism.This is about running the fire drill before the smoke fills the room. Because communication isn’t just advice. It’s lubrication. And the hardest conversations are where the breakthroughs are hiding.Chapters:0:00 - Introduction1:47 - Communication is lubrication6:30 - Don't let your kids lose both parents11:00 - Define your plan and identify these key concerns17:18 - A client's life is turned upside down24:10 - Do your fire drill so you're prepared when something happens26:00 - Things you can do right now!28:15 - The critical choice you need to make

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’re saving, and how even simple, legal, IRS-approved strategies can unlock six to seven figures in wealth every year.From the Augusta Rule, to hiring your kids, to the power of corporate structure, advanced retirement plans, cost segregation, and energy credits — this episode is a masterclass in turning taxes from a burden into a business accelerator.If you are a family business owner, founder, or entrepreneur, the government has already written a 70,000-page playbook directing you toward tax-free wealth.The only question is whether you’re going to use it.Chapters:0:00 - Introduction2:05 - The Tax Code is a set of instructions on how to play the game3:45 - The Tax Code is actually your business plan6:38 - The Family Business Advantage9:30 - Advanced strategies your CPA forgot to mention12:30 - Rogue Wealth Rule #416:20 - Key takeaways19:50 - Closing remarks

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, leadership, and systems that separate legacy-building businesses from those treading water.This episode delivers clarity, challenge, and a call to action for any family-owned business ready to move from mediocrity to mastery.Chapters:0:00 - Introduction2:18 - The Family Business Performance Hierarchy5:38 - What it means to be a "struggling" business9:11 - Who are truly "Game Changers" in their industry? 12:09 - The Apex Family Business16:39 - Rethinking core business models to reduce distraction19:41 - Growth solves all problems22:01 - Closing remarks

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 often sitting across from you at the dinner table.Kris breaks down the frameworks used by successful family enterprises to transform dysfunction into discipline, and emotion into clarity. You’ll learn:How to define your family charter and core values — the unbreakable commandments guiding every decision.Why everyone is watching — how your behavior sets the standard for every generation that follows.What professional governance really looks like — and how to enforce systems that transcend last names.How to identify your “bodyguards and sounding boards” — the people who keep you accountable when decisions get emotional.Through powerful stories and real-world lessons—including the fallout of a $400 million family business collapse—Kris reveals how even the most successful families can lose everything when emotion overrides structure.

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 designed to distract, not empower. The truth? Even accurate information can derail your focus and become a hidden tax on your decision-making.In this episode, we’ll unpack:The Signal-to-Noise Tax — why not all inputs are equal.How to Build Your Personal Filter — the decision framework that protects your focus.Silence as a Skill — guarding your brain real estate from distractions.Why Today’s Rate of Change Demands Preparation — and how ignoring it puts your future at risk.Along the way, I’ll share real stories — from navigating messy partnerships to making bold investments when panic ruled the market — to show how discipline, focus, and silence create the space where wealth is built.If you’re ready to filter out the noise, stop reacting, and start moving the needle on what matters most, this episode will give you the tools to do it.Learn more at ProsperiFi.com, or schedule a Power-Up session to get your family business on track to excellence.Chapters:0:00 - Introduction1:00 - Noise paralyzes you from making decisions4:17 - Signal to Noise Tax6:28 - Rogue Wealth Rule #110:32 - Silence is a tough skill to utilize17:19 - Noise impacting a business partnership21:02 - Key takeaways23:11 - Closing remarks