Joe Fairless' Journey From Madison Avenue To An $85 Million Real Estate Portfolio

Ambition Today Kevin Siskar Joe Fairless

In keeping with last weeks' real estate theme, Episode 25 of Ambition Today finds us across the table from Joe Fairless, Real Estate Investor and Host of the Best Real Estate Investing Advice Ever Show.  Joe set his roots in advertising after a bit of soul-searching during his undergrad years at Texas Tech.  Fighting complacency, he left Madison Ave. for the allure of real estate investing and entrepreneurship, and was met with incredible success, with due credit to his persistence and work ethic.

Owing his early sense of drive to his start in landscaping, Joe Fairless has always had an entrepreneurial mindset.  After leaving his teenage lawn-mowing business, J&J Landscaping, Joe tried to cling to his high school football career by attending a junior college near his home town of Dallas.  After transferring, he went on to graduate with a degree in advertising and quickly rose through the ranks of executive marketing, while investing in real estate as a side project and finding passion in that venture.  Joe applied his trademark tenacity to his newfound love of investing and now controls approximately $85 million worth of rental property.  Kevin digs into the factors behind Joe's success, and much more:

  • The seemingly hidden on-ramp of landscaping as a teenage job to eventually invest in real estate.

  • Exploring passions during college to find what interests you.

  • Applying lessons from the corporate world to an entrepreneurial startup.

  • Leaving a comfortable job to pursue your real dreams.

  • How to break into the shark-infested waters of commercial real estate.

  • The 75/25 rule of listening/asking when approaching mentors.

  • Acknowledging your strengths.

  • Acknowledging your weaknesses and surrounding yourself with people who help make up for them.

  • The grit of making your ambition come to life.


Ambition Today Question of the Day™:
"As a thought leader, how does ambition play a role in your life?"

Quote Of The Episode:
"Don't get caught up trying to be everywhere at once, find the platform that makes sense for your skill sets and what you enjoy doing. Then own it."  - Joe Fairless

“Be different before being incrementally better.” - Joe Fairless


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