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The Duality & The Dollar

with

Joe Orlando

President of Joseph Orlando Clothier, a men’s clothing store for over 40 years.

Listen to the Full Episode 

The Duality & The Dollar

From owning a bar at 19 to running a men’s clothing store for over 40 years, Joe shares how relationships, reinvention, and humility have kept him grounded through every business change.


What you'll Learn:

  • Why every business thrives on relationships

  • How to pivot when your market changes

  • What it means to start from zero every day

  • Lessons learned from decades of entrepreneurship

  • Balancing humility, gratitude, and success

Spotlight Conversation

A serial entrepreneur's journey is revealed, tracing his start from securing a $12,000 loan to open a bar at age 19; his core principle is that genuine appreciation for everyone, from CEOs to the homeless, is the ultimate key to staying grounded and achieving four decades of success.

Questions Randall is Wondering After This Episode

What if it were still possible to take out bank loans to start a small business? Instead of student loans? And why did that change? Both are unsecured loans, but one is allowed and the other isn’t.
What does “starting from zero” really mean in modern business?
How can we stay humble while chasing growth? What does reinvention look like in a rapidly changing market?

Memorable Quotes

"It's easy to focus on the glamorous side of running a business, but success also depends on unglamorous work life cleaning, accounting and hauling trash. You have to respect the nuts and bolts for it all to hold together."

About the Guest

medium-shot-woman-with-headphones_23-2149386584.jpg_ga=GA1.1.888384636.1732005982&semt=ais

Joe Orlando

Entrepreneur

President of Joseph Orlando Clothier, a men’s clothing store for over 40 years.

Find Joe:

Instagram
LinkedIn
TikTok
Facebook
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