Wealth Management Archives – ProsperiFi

Cinematic photograph of a person inside a glass jar, focused intently on what's in front of them, unable to see the label affixed to the outside — visual metaphor for the cognitive blind spot business owners face when they refuse outside advice.

Entrepreneurship Family Business Matters Wealth Management

You Can’t Read The Label From Inside The Jar

My buddy runs an exotic car business. Expert level technician, great salesman, and a decent…

Kris GarlewiczApril 24, 2026

Family Business Matters Investment Insights Wealth Management

Your Favorite Financial Institution Just Put a Slot Machine Next to the Teller Window

And they're calling it "investing." Don't believe them. My grandfather built houses. Poured foundations himself.…

Kris GarlewiczApril 16, 2026

Deal fatigue is the weapon.

Family Business Matters Wealth Management

Deal Fatigue Is a Weapon. They’re Counting on You Not to Know That.

There's a moment in almost every major business sale where the founder looks across the…

Kris GarlewiczApril 9, 2026

Risk Management Options

Investment Insights Wealth Management

“Sell in May and Go Away” Is Broken – Why Process Trumps Panic

“Sell in May and Go Away” Posts Another Fail Refuse to Let Anecdotes Destroy Your…

Kris GarlewiczJune 5, 2025

Family business leaders breaking through performance barriers and aligning around growth.

Family Business Matters Wealth Management

Family Business, Unchained: Why Most Family Businesses Plateau – and How the Elite Rise Past the Noise

As a family business owner, you don’t need more ideas. You need fewer obstacles. The…

Kris GarlewiczApril 15, 2025

The Illusion of Permanence and Investing

Investment Insights Wealth Management

Trump’s April 2025 Tariffs: How Investors Should Respond | ProsperiFi

Navigating the Latest Tariffs and the Illusion of Permanence While I generally consider myself a…

Kris GarlewiczApril 4, 2025

Managing Social Security

Wealth Management

Understanding Social Security: Facts Over Fear

Election season brings many hot-button topics and debates. Social Security is one of them. Over…

Kris GarlewiczMay 16, 2024

The 2019 Inheritance Checklist

Wealth Management

The 2019 Inheritance Checklist

Inheriting a large sum of money can be exhilarating. After the initial excitement wears off,…

Kris GarlewiczAugust 5, 2019

Your Inheritance, Your Happiness

Wealth Management

Your Inheritance, Your Happiness

Giving makes us feel good inside. From giving someone a compliment to making a large…

Kris GarlewiczJuly 22, 2019

Inheriting a 401(k)

Wealth Management

Inheriting a 401(k)

What You Need to Know Inheriting a 401(k)Picturing an inheritance, it can be easy to…

Kris GarlewiczJune 23, 2019