Keith Riddle – Mastering the Long Game
In the first episode of Chess Not Checkers, hosts Jordan Tampien and Keith Riddle dive into Keith’s journey from a new real estate agent to a seasoned entrepreneur. Keith shares how curiosity, calculated risks, and a mix of engineering principles helped him grow both in business and personally. They discuss shifts in the real estate industry, the mindset it takes to push through challenges, and the importance of thinking long-term.
Chess Not Checkers is a podcast all about playing the long game in both business and life, exploring how strategic thinking, patience, and calculated risks can lead to lasting success. Each conversation will dive into the stories of individuals who think beyond immediate rewards, focusing on the bigger picture and long-term impact. Whether it’s navigating the challenges of entrepreneurship, making mindful decisions, or creating a legacy, our hosts Jordan Tampien & Keith Riddle will be here to inspire you to take a step back, plan ahead, and make decisions that pay off over time.
00:00 – Introduction to Chess Not Checkers
01:02 – Meet Keith Riddle: The Journey Begins
02:16 – From Engineering to Real Estate
03:17 – Early Success and Market Dynamics
07:07 – Innovative Strategies in Real Estate
12:47 – The Power of Technology and Lead Generation
18:43 – Building a Real Estate Empire
26:00 – Diversifying with Investments and Flipping Houses
28:33 – Starting an Independent Brokerage
29:30 – Venturing into Development
30:33 – Mentorship and Synergy
32:07 – Navigating Market Challenges
32:43 – The Importance of Numbers
33:31 – Innovative Marketing Strategies
34:53 – Adapting to Market Changes
36:09 – Balancing Business and Innovation
39:17 – Taking Risks and Learning from Failure
52:48 – Managing Capacity and Capability
01:01:01 – Visualizing Success: The Power of Mental Rehearsal
01:02:28 – The Rucksack Race: A Mental and Physical Challenge
01:05:00 – Endurance Racing and Life Lessons
01:09:58 – Balancing Work, Health, and Personal Goals
01:16:34 – Annual Planning for a Balanced Life
01:21:08 – Reflecting on Success and Future Goals
01:24:47 – Playing the Long Game
