Author

Jessey Kwong
Pebble Co-Founder
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From Wholesaling to Passive Income: How He Did It
Jul 3, 2025
Podcast
What happens when you combine cold-calling grit, creative deal structuring, and a mission to serve others through real estate? James Michener went from working a cubicle job to building a diversified investing business that includes wholesaling, flipping, lending, and long-term rentals — all before hitting 35. Jessey sits down with James to unpack the pivotal moments, mindset shifts, and real-life tactics that helped him stack momentum (and income) year after year.
James doesn’t hold back. From his early days knocking doors and working out of his car to structuring joint ventures and subject-to deals, you’ll hear how he turned simple prospecting into million-dollar opportunities. He walks through his personal systems, how he filters motivated sellers, and why paying off half his rental portfolio was one of the smartest moves he ever made.
If you're feeling stuck on where to begin or how to scale, this conversation delivers both inspiration and execution. Whether you're on deal #1 or #100, James’ no-fluff approach to building a real estate business will help you rethink consistency, data, and what it really means to build a life of freedom.
In this episode:
How James turned cold calls into a million-dollar deal flow
Creative structures like wraps, seller carrybacks, and joint ventures
The mindset and routines that built long-term momentum
What James would prioritize if he were starting from scratch today