All Episodes

April 17, 2025 22 mins

When it comes to investing, are you picking winners or just playing favorites? In this episode, Ryan breaks down how our emotional biases, gut instincts, and misplaced confidence can sabotage even the best financial intentions.

Using bracket-building and sports betting as a metaphor, Ryan explores how chasing individual stocks is a lot like guessing tournament upsets: unpredictable, addictive, and often disappointing.

Here’s what we cover in this episode:

🧠 Why emotional investing leads to poor decisions

📉 The surprising odds of stock-picking success

📈 Why diversification still beats “gut feeling”

⚠️ The hidden risks of being loyal to one stock

📚 How real market data can reframe your mindset

 

Retire Pilots - https://retirepilots.com

 

Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/

 

Pilot Tax - https://pilot-tax.com/

 

The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Mark as Played

Advertise With Us

Popular Podcasts

Cold Case Files: Miami

Cold Case Files: Miami

Joyce Sapp, 76; Bryan Herrera, 16; and Laurance Webb, 32—three Miami residents whose lives were stolen in brutal, unsolved homicides.  Cold Case Files: Miami follows award‑winning radio host and City of Miami Police reserve officer  Enrique Santos as he partners with the department’s Cold Case Homicide Unit, determined family members, and the advocates who spend their lives fighting for justice for the victims who can no longer fight for themselves.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.