In this powerful episode of Burning the Ships, I sit down with Wendy Coles, whose story is a raw, inspiring example of resilience, resourcefulness, and redemption. From a troubled relationship with her mother and running into legal trouble at 18, to raising four kids, rebuilding her life, and eventually finding freedom through real estate and service, Wendy’s journey shows what it means to keep moving forward—no matter the storm.
We dive deep into her early struggles with identity, her time on the run while pregnant, and how she turned setbacks into stepping stones for growth. Wendy also shares how she discovered her true heritage later in life, how real estate investing gave her the stability she always sought, and how giving back through Chair the Love (a charity that delivers wheelchairs worldwide) has reshaped her purpose.
This conversation is about more than real estate—it’s about storms, strength, and the courage to step into who you’re meant to be.
Key Talking Points of the Episode
00:00 Introduction
01:27 JJ’s Joke of the Week
02:32 Wendy’s background: strained relationship with her mom, identity struggles, and introversion
05:33 Meeting Eddie, stolen cars, jail time, and learning she was pregnant at 18
08:20 Running away to Canada while pregnant, fear vs. fearlessness, and life on the run
13:08 Homelessness, shelters in Buffalo, and the decision to turn herself in
17:17 Jail, probation, teen motherhood, and the burden of a felony record
19:25 DNA test reveals her true identity—meeting her Filipino father and half-siblings
25:28 Raising Jocelyn, honesty about her father, and building family bonds
29:27 Balancing kids, divorce, and survival as a single mom with sales jobs
35:10 Marriage, entrepreneurship, running a sports training facility, and parental validation
40:28 Closing the facility, husband’s health issues, and pivoting into real estate
42:35 From flipping to buy-and-hold: building long-term wealth and getting licensed despite felonies
45:16 Managing rentals, short-term rentals, and self-managing tenants successfully
49:09 Discovering Chair the Love: providing wheelchairs, mission trips, and real estate mastermind connections
59:03 Health, habits, and staying youthful at 54—honesty about struggles with food and workouts
01:03:11 Storms as opportunities: why challenges clear the path for something better
Quotables
“Storms destroy what isn’t solid and reveal what is.”
“Most kids won’t remember the money you made, but they’ll remember the time you spent.”
“Getting uncomfortable is where the best results in life come from.”
Links
Chair the Love
https://www.facebook.com/CTLFlorida/
Wendy Coles
https://www.facebook.com/wendy.r.coles
608B Capital
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