Pickleball – The WIN Podcast

From Courts to Capital: What Pickleball Teaches Us About Investing (EP. 90)

By The-WIN-Podcast | September 30, 2025

Pickleball has exploded from a backyard game into the fastest-growing sport in America, and its journey offers valuable lessons for investors. In this episode of The WIN Podcast, Corey and Zed look at how the sport’s rapid rise mirrors trends in finance, from spotting opportunities early to understanding the importance of having a reliable partner.

We connect paddles to portfolios, exploring what pickleball teaches us about patience, risk, strategy, and long-term thinking. Whether you’re on the court or in the market, the principles are the same: play smart, stay adaptable, and focus on the bigger picture.

Resources

Corey’s Book

Connect

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

Winter Tennis Breakdown (Ep. 47)

By The-WIN-Podcast | February 13, 2024

What do tennis and finance have in common?

More than you might think!

In both fields, unforced errors can have a huge impact on your performance and outcomes.

This week, Corey Heimensen explores the concept of unforced errors in finance, draws parallels between tennis and decision-making, and dives into the psychology behind our choices. He also emphasizes the importance of learning from mistakes, avoiding overconfidence, and planning for the future.

Corey discusses:

Unforced errors in tennis and golf, and how they relate to mistakes made in the investing and finance world
The US Open, the crowd, and the drink called ‘Honey Deuce’
The importance of evaluating mistakes and learning from them in order to improve in various aspects of life
The importance of understanding and not underestimating the risks associated with investments and financial decisions
The dangers of overconfidence and the inevitable market downturns
The importance of managing taxes, ensuring cash flow, and weathering market volatility for long-term success
And more!