Chess Not Checkers
Chess Not Checkers
Podcast Description
Welcome to Chess Not Checkers, the podcast that teaches you how to play the long game in both business and life. Hosted by Keith Riddle and Jordan Tampien, we dive deep into strategic thinking, exploring how the best minds think several steps ahead. Each episode features guests from a variety of fields — real estate, business, health, wealth, and more — who share their stories and the unique mindset that’s propelled their success. Whether you’re building, growing, or establishing your business, this show offers valuable insights to help you think smarter and act with purpose.
Podcast Insights
Content Themes
The show focuses on strategic thinking, entrepreneurship, and personal growth, with episodes exploring topics such as business adaptation, work-life balance, and long-term planning. Examples include discussions on the entrepreneurial mindset with guests from various industries, including real estate and digital marketing, offering lessons from their unique journeys.
Welcome to Chess Not Checkers, the podcast that teaches you how to play the long game in both business and life. Hosted by Keith Riddle and Jordan Tampien, we dive deep into strategic thinking, exploring how the best minds think several steps ahead. Each episode features guests from a variety of fields — real estate, business, health, wealth, and more — who share their stories and the unique mindset that’s propelled their success. Whether you’re building, growing, or establishing your business, this show offers valuable insights to help you think smarter and act with purpose.
In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien are joined by Justin Avey for a different kind of conversation—breaking down the good deals and the bad deals that shaped their careers.
Instead of focusing on a single project or business, the three dive into the real stories behind some of the biggest wins and toughest lessons they’ve experienced in real estate and development. From projects that turned into unexpected successes to deals that dragged on for years with setbacks, contractors, and surprises, nothing is off the table.
Keith shares the story of a South Hill project that became a long, stressful journey before finally turning around. Jordan reflects on the ups and downs of redevelopment and large-scale projects, while Justin brings his own perspective from the construction side of the business.
Good Deal / Bad Deal is an honest look at what it really takes to stay in the game. Behind every successful investor are the deals that nearly broke them—and the ones that made it all worth it.
Disclaimer
This podcast’s information is provided for general reference and was obtained from publicly accessible sources. The Podcast Collaborative neither produces nor verifies the content, accuracy, or suitability of this podcast. Views and opinions belong solely to the podcast creators and guests.
For a complete disclaimer, please see our Full Disclaimer on the archive page. The Podcast Collaborative bears no responsibility for the podcast’s themes, language, or overall content. Listener discretion is advised. Read our Terms of Use and Privacy Policy for more details.