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.

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.

If you're within five years of a business sale, this is the most important conversation you haven't had yet.

Chapters:

0:00 Introduction & the scenario

0:18 Imagine this: 8 months into selling your business

2:03 Deal fatigue is not a side effect — it's a strategy

3:18 Rogue Wealth Rule #3: This is a contact sport

4:21 Part 1: The wave nobody is talking about

5:28 The counterparty: $3.7 trillion in PE dry powder

6:39 The imbalance of sophistication has never been greater

7:43 Part 2: The anatomy of the trap — 4 phases

8:42 Phase 1: The seduction (the IOI)

9:45 Phase 2: The letter of intent

10:44 Phase 3: Due diligence

11:44 Phase 4: The kill zone — the adjustments

14:38 Part 3: The six tactics

15:00 Tactic 1 — Timeline extension

15:35 Tactic 2 — Scope creep

16:02 Tactic 3 — IOI anchoring

16:32 Tactic 4 — Escalation of commitment

17:22 Tactic 5 — Using your own people against you

18:09 Tactic 6 — The re-trade

19:06 Part 4: Why family businesses bleed more

19:22 Layer 1 — The founder's identity is the business

20:17 Layer 2 — The family creates internal pressure

21:31 Layer 3 — The business suffers and buyers use it

22:16 Part 5: The defense

23:18 Defense 1 — Define success in writing before you engage

25:01 Defense 2 — Get your financial house in order

25:54 Defense 3 — Build your advisory team before you engage

26:52 The uncomfortable truth about banker incentives

27:48 Defense 4 — Align the family

29:09 The test for founders in the middle of a deal right now

31:19 The closing: generational wealth vs. a one-time event

33:29 Get Deal Ready: ProsperiFi.com

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 actually destroys culture is the gap between what leadership says… and what leadership allows.

What happens when high performers quietly carry underperforming relatives?

What happens when accountability changes based on last names?

What happens when everyone in the company knows the rules aren’t applied equally?

That’s where culture is revealed.

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.

You’ll also learn:

• Why culture theater is destroying trust inside family businesses
• The hidden danger of double standards in leadership
• How top performers silently disengage before they leave
• The “Rogue WHAT Stack” framework for auditing your culture
• Why purpose without practice is just poetry
• What separates Apex businesses from those trapped in mediocrity

This is a direct, unapologetic conversation about leadership, accountability, and the operational reality of family business culture.

Because culture isn’t what you say you stand for. It’s what you let happen.

Chapters:

0:00 - Introduction

1:36 - The WHY is a performance

3:15 - The family business twist

7:00 - The Observability, Consistency, and Conflict Tests

11:05 - The high performer vs. low performer truth

13:56 - The Simon Sinek counter

16:08 - A recent client meeting on culture

21:00 - Rogue Wealth Rule #9

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 - Introduction

1:05 - There's a 75% chance of misery in a year

3:45 - You're just the guy that used to run a company

7:30 - The "Exit to Greatness" Roadmap

13:30 - The job of a Financial Bodyguard

17:09 - Helping a client define their "next love"

19:15 - Actions you can do right now!

20:45 - Closing remarks

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:

1. Why clarity is a byproduct of action — not a prerequisite
2. The pressure of leading a family-run business without an operating manual
3. The entitlement vs. imposter syndrome tension that few talk about openly
4. How ego quietly becomes the greatest liability in growing organizations
5. Why comfort is often the most expensive phase of a business lifecycle
6. The financial value of time — and how to actually prioritize it

This 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 - Introduction

1:58 - "Don't dismiss the good energy when you know it"

7:10 - Working without a user guide

17:38 - Intuition and experience are what matter most

28:40 - The imposter syndrome

37:37 - Capturing operational systems properly

47:10 - Advice to your former self

54:53 - Stop looking for clarity. Decide and do!

59:20 - Closing remarks

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:

1. Why 100% bonus depreciation being permanent changes capital planning strategy
2. The real risks and leverage behind taking equity in lieu of payment
3. What private equity firms actually look for in founder-led businesses
4. Why noncompete language after a sale can define (or restrict) your next chapter
5. The power of multidisciplinary collaboration between legal, tax, and advisory professionals

Kris 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 - Introduction

1:20 - The common roadblocks hitting business owners

4:22 - Private equity is looking for this

10:40 - Rogue Wealth Rule #6

16:23 - Taking equity in lieu of payment

21:22 - Non-competes and post-sale realities

27:15 - The emotionally misjudged moments

30:20 - Closing remarks

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 - Introduction

1:47 - Communication is lubrication

6:30 - Don't let your kids lose both parents

11:00 - Define your plan and identify these key concerns

17:18 - A client's life is turned upside down

24:10 - Do your fire drill so you're prepared when something happens

26:00 - Things you can do right now!

28:15 - The critical choice you need to make

“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 - Introduction

2:05 - The Tax Code is a set of instructions on how to play the game

3:45 - The Tax Code is actually your business plan

6:38 - The Family Business Advantage

9:30 - Advanced strategies your CPA forgot to mention

12:30 - Rogue Wealth Rule #4

16:20 - Key takeaways

19:50 - Closing remarks

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 - Introduction

2:18 - The Family Business Performance Hierarchy

5:38 - What it means to be a "struggling" business

9:11 - Who are truly "Game Changers" in their industry?

12:09 - The Apex Family Business

16:39 - Rethinking core business models to reduce distraction

19:41 - Growth solves all problems

22:01 - Closing remarks

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.

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 - Introduction

1:00 - Noise paralyzes you from making decisions

4:17 - Signal to Noise Tax

6:28 - Rogue Wealth Rule #1

10:32 - Silence is a tough skill to utilize

17:19 - Noise impacting a business partnership

21:02 - Key takeaways

23:11 - Closing remarks