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Rogue Wealth

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by Kris Garlewicz

5.0(2 reviews)
10 episodes
Updated Daily
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Podcast Overview

Rogue Wealth is a podcast built for the business owner who refuses to play the “average amateur game.” If you’re leading a family business, building wealth, or simply trying to cut through the noise in a world moving exponentially faster, this show is your edge. Hosted by a wealth strategist who has “seen it all”—from messy partnerships to generational transitions—Rogue Wealth slows everything down so you can focus on what truly moves the needle. Each episode combines storytelling, tactical empathy, and a comprehensive approach to help you navigate the unique challenges of building, protecting, and passing on wealth. We cover it all: Family Business Essentials — governance, succession, family constitutions, and the founders’ code. Wealth Management Strategies — cash management, tax, risk, and legacy planning. Business Owner Realities — leadership, operations, decision-making, and crisis management. Lifestyle and Mindset — how to block out distractions and stay focused on the long game. What sets Rogue Wealth apart is accountability: you’ll hear not only from me, but also from the A-team of wealth professionals I bring to the table, all focused on one thing—your success. Because wealth isn’t built in chaos. It’s built in the quiet spaces, with discipline, clarity, and the courage to do things differently.

Language

🇺🇲

Publishing Since

9/29/2025

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Recent Episodes

Episode thumbnail for Deal Fatigue is a Weapon: How Sophisticated Buyers Engineer Your Surrender

June 11, 2026

Deal Fatigue is a Weapon: How Sophisticated Buyers Engineer Your Surrender

<p>Nobody warns you that deal fatigue is a weapon.</p><p>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.</p><p>Most founders take it. Not because they're weak — because they're exhausted. And that exhaustion was engineered.</p><p>In Episode 10 of Rogue Wealth, Kris Garlewicz walks through the full playbook: the four phases of a deal where leverage accumulates, six specific tactics used to grind down sellers, why family businesses are uniquely vulnerable, and the pre-engagement discipline that keeps you in control from day one.</p><p>If you're within five years of a business sale, this is the most important conversation you haven't had yet.</p><p></p><p>Chapters:</p><p>0:00 Introduction &amp; the scenario</p><p>0:18 Imagine this: 8 months into selling your business</p><p>2:03 Deal fatigue is not a side effect — it's a strategy</p><p>3:18 Rogue Wealth Rule #3: This is a contact sport</p><p>4:21 Part 1: The wave nobody is talking about</p><p>5:28 The counterparty: $3.7 trillion in PE dry powder</p><p>6:39 The imbalance of sophistication has never been greater</p><p>7:43 Part 2: The anatomy of the trap — 4 phases</p><p>8:42 Phase 1: The seduction (the IOI)</p><p>9:45 Phase 2: The letter of intent</p><p>10:44 Phase 3: Due diligence</p><p>11:44 Phase 4: The kill zone — the adjustments</p><p>14:38 Part 3: The six tactics</p><p>15:00 Tactic 1 — Timeline extension</p><p>15:35 Tactic 2 — Scope creep</p><p>16:02 Tactic 3 — IOI anchoring</p><p>16:32 Tactic 4 — Escalation of commitment</p><p>17:22 Tactic 5 — Using your own people against you</p><p>18:09 Tactic 6 — The re-trade</p><p>19:06 Part 4: Why family businesses bleed more</p><p>19:22 Layer 1 — The founder's identity is the business</p><p>20:17 Layer 2 — The family creates internal pressure</p><p>21:31 Layer 3 — The business suffers and buyers use it</p><p>22:16 Part 5: The defense</p><p>23:18 Defense 1 — Define success in writing before you engage</p><p>25:01 Defense 2 — Get your financial house in order</p><p>25:54 Defense 3 — Build your advisory team before you engage</p><p>26:52 The uncomfortable truth about banker incentives</p><p>27:48 Defense 4 — Align the family</p><p>29:09 The test for founders in the middle of a deal right now</p><p>31:19 The closing: generational wealth vs. a one-time event</p><p>33:29 Get Deal Ready: ProsperiFi.com</p>

Episode thumbnail for Forget WHY. Family Businesses Win on WHAT.

May 12, 2026

Forget WHY. Family Businesses Win on WHAT.

<p>Most family businesses don’t have a purpose problem. They have an execution problem.</p><p>In this episode of Rogue Wealth, Kris Garlewicz takes aim at one of the most celebrated ideas in modern business culture: Start With Why.</p><p>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.</p><p>What actually destroys culture is the gap between what leadership says… and what leadership allows.</p><p>What happens when high performers quietly carry underperforming relatives?</p><p>What happens when accountability changes based on last names?</p><p>What happens when everyone in the company knows the rules aren’t applied equally?</p><p>That’s where culture is revealed.</p><p>Kris breaks down why Apex family businesses operate differently, how clarity is built through observable behavior, and why “everyone knows the deal” may be the most powerful culture strategy in business today.</p><p>You’ll also learn:</p><ul><li>Why culture theater is destroying trust inside family businesses</li><li>The hidden danger of double standards in leadership</li><li>How top performers silently disengage before they leave</li><li>The “Rogue WHAT Stack” framework for auditing your culture</li><li>Why purpose without practice is just poetry</li><li>What separates Apex businesses from those trapped in mediocrity</li></ul><br/><p>This is a direct, unapologetic conversation about leadership, accountability, and the operational reality of family business culture.</p><p>Because culture isn’t what you say you stand for. It’s what you let happen.</p><p></p><p>Chapters:</p><p>0:00 - Introduction</p><p>1:36 - The WHY is a performance</p><p>3:15 - The family business twist</p><p>7:00 - The Observability, Consistency, and Conflict Tests</p><p>11:05 - The high performer vs. low performer truth</p><p>13:56 - The Simon Sinek counter</p><p>16:08 - A recent client meeting on culture</p><p>21:00 - Rogue Wealth Rule #9</p>

Episode thumbnail for Exit to Greatness: The 75% Misery Statistic Nobody Talks About

March 18, 2026

Exit to Greatness: The 75% Misery Statistic Nobody Talks About

<p>75% of business owners regret selling their company — and it’s not because of the money.</p><p>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.</p><p>Know what you're running toward before you run from what you've built.</p><p>If you’re thinking about selling, this episode is required listening!</p><p>Chapters:</p><p>0:00 - Introduction</p><p>1:05 - There's a 75% chance of misery in a year</p><p>3:45 - You're just the guy that used to run a company</p><p>7:30 - The "Exit to Greatness" Roadmap</p><p>13:30 - The job of a Financial Bodyguard</p><p>17:09 - Helping a client define their "next love"</p><p>19:15 - Actions you can do right now!</p><p>20:45 - Closing remarks</p>

10 total episodes available

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What is Rogue Wealth?

Rogue Wealth is a podcast built for the business owner who refuses to play the “average amateur game.” If you’re leading a family business, building wealth, or simply trying to cut through the noise in a world moving exponentially faster, this show is your edge.

Hosted by a wealth strategist who has “seen it all”—from messy partnerships to generational transitions—Rogue Wealth slows everything down so you can focus on what truly moves the needle. Each episode combines storytelling, tactical empathy, and a comprehensive approach to help you navigate the unique challenges of building, protecting, and passing on wealth.

We cover it all:

Family Business Essentials — governance, succession, family constitutions, and the founders’ code.

Wealth Management Strategies — cash management, tax, risk, and legacy planning.

Business Owner Realities — leadership, operations, decision-making, and crisis management.

Lifestyle and Mindset — how to block out distractions and stay focused on the long game.

What sets Rogue Wealth apart is accountability: you’ll hear not only from me, but also from the A-team of wealth professionals I bring to the table, all focused on one thing—your success.

Because wealth isn’t built in chaos. It’s built in the quiet spaces, with discipline, clarity, and the courage to do things differently.

How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

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