What if the biggest risk to your family's wealth isn't the market?

What if it's the person receiving it?

In this episode of Rogue Wealth, Kris Garlewicz tackles the uncomfortable truth behind multigenerational wealth: families can spend decades preparing their assets for their children without adequately preparing their children for the assets.

Drawing from more than 20 years working with family businesses and his own experience raising six kids, Kris breaks down the principles he believes help create capable next-generation stewards.

Inside the episode:

• Why generational wealth can fail long before the transfer

• Raising winners instead of dependents

• Why comfort can become a liability

• Teaching kids to earn before they receive

• Why consistency matters more than intensity

• Connection before correction

• Teaching responsibility through the household economy

• Why family business successors should learn the business from the ground up

• Respect as the price of admission

• Intentionally building grit

• Kris's five-book "family syllabus"

• Why your children may be your largest multigenerational asset

You can create the estate plan.

You can fund the trust.

You can transfer the business.

But you cannot wire character.

Build winners. Not dependents.

Subscribe to Rogue Wealth for more conversations about family business, wealth, leadership, legacy, and making decisions differently.

Chapters:

00:00 – Winners, Not Dependents

01:28 – Why Generational Wealth Really Fails

03:42 – Comfort Is a Liability

05:03 – Axiom #1: Raise Winners, Not Dependents

08:33 – Axiom #2: Don't Raise the Bar. Hold It.

11:33 – Axiom #3: Connection Before Correction

14:59 – 5 Ingredients for Building Future Stewards

17:00 – The Household as the First Free Market

18:14 – Preparing Kids for the Family Business

20:37 – Building Grit on Purpose

24:42 – Kris' Family Syllabus

30:34 – You Can Wire Money. You Can't Wire Character.

What if taking responsibility doesn't mean accepting blame?

In this deeply personal episode of Rogue Wealth, Kris Garlewicz shares the seven words that changed how he shows up as a father, husband, business owner and advisor:

“It’s not my fault, but my responsibility.”

Kris explores the difference between fault and responsibility, how misplaced guilt can create paralysis, and why family businesses are particularly vulnerable to these patterns.

A personal story with implications for leadership, succession, family wealth and legacy.

Chapters:

0:00 — 7 Words That Saved My Life

2:00 — When Extreme Ownership Goes Too Far

2:55 — Fault vs. Responsibility

4:28 — Why “Why?” Can Keep You Stuck

4:53 — The Research Behind the Idea

8:00 — The Leadership Trap

8:54 — Extreme Ownership ≠ Extreme Fault

9:31 — How Fault Shows Up in Family Businesses

14:47 — The 4-Step Responsibility Protocol

16:05 — Responsibility vs. Authority

17:20 — Say It Out Loud

17:44 — The Legacy at Stake

18:36 — The 7 Words That Changed Everything

19:25 — Viktor Frankl: A Final Recommendation

Everyone dreams about finding the next NVIDIA, Amazon, or Tesla.

Very few investors know what to do after they find one.

In this episode of Rogue Wealth, Kris Garlewicz, Founder of ProsperiFi and your Financial Bodyguard, breaks down one of the biggest misconceptions in investing: growth investing isn't about chasing hot stocks. It's about creating a repeatable framework for identifying long-term opportunities, managing risk, and protecting your wealth once those investments begin to compound.

Kris walks through the four pillars every investor should understand:

• Why growth investing deserves a place inside a diversified portfolio

• The different ways to execute a growth strategy without falling victim to FOMO

• How sophisticated investors manage risk while allowing winners to continue compounding

• Tax strategies that can help preserve life-changing gains instead of letting the IRS become your largest investment partner

Along the way, Kris shares why most business owners are exceptional capital allocators inside their businesses but often neglect the same discipline inside their personal portfolios.

If you've ever wondered what to do after an investment doubles... or grows 3,000%... this episode gives you a practical framework for thinking beyond the next trade and toward generational wealth.

Because growth investing isn't reckless. It's systematic.

Chapters:

0:00 - Everybody Wants the 3,000% Winner. Now What?

2:15 - Why Growth Investing Belongs in a Diversified Portfolio

5:48 - Growth Investing vs. Value Investing

10:26 - Spotting Structural Trends Before Everyone Else

15:42 - DIY Investing vs. Hiring a Growth Manager

21:18 - Why Business Owners Struggle With Their Own Portfolios

26:54 - Managing Risk Without Killing Returns

31:40 - How to Know When to Trim Your Winners

36:25 - Covered Calls, Income Strategies & Portfolio Management

41:12 - The Tax Mistakes Investors Make on Big Gains

47:10 - Don't Let Taxes Dictate Your Investment Decisions

51:45 - Rogue Wealth Rule #11: Momentum Is Your Friend

54:10 - Final Takeaways & Building a Repeatable Investment Framework

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.

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

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 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

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 - 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

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:

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

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:

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

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 - 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

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 - 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