Johnathan Trimble is a real estate investor and team leader at Executive Asset Properties, a Keller Williams team he built with his business partner, Jim. Together they've built a portfolio of more than 200 flips, rentals, and syndication units. But behind the business success is a story of setbacks, resilience, and a chronic illness most people never see.

Johnathan's parents loaned him the money for his first flip. It flooded. It was broken into. Two trees fell on the property. The listing hit the market three months late, sat without selling, and ultimately lost $26,000. His parents offered to forgive part of what he owed them. He paid every dollar back anyway, because a deal is a deal.

That was only the beginning.

A commercial real estate career disappeared during COVID. A $40,000 mentorship turned out to be a scam. A promising investment deal was rug-pulled before he earned a dollar. He and Jim accumulated nearly $200,000 in credit card debt building Rehome KC before eventually launching Executive Asset Properties at Keller Williams.

All the while, Johnathan was quietly battling ankylosing spondylitis, a hereditary autoimmune disease that attacks the spine and joints. For years he woke up several times every night in debilitating pain, hiding it from almost everyone. It wasn't until meeting a life coach with the same diagnosis that he discovered how much mindset and gratitude could change the way he lived with the disease.

In this episode, Johnathan and host Genevra Collins discuss why "other people's money" completely changed his view of investing, the $40,000 mentorship scam and the deal that fell apart before it began, the first flip that seemed destined to fail and why he still paid his parents back in full, living with ankylosing spondylitis and finding hope beyond medication, and why real success isn't avoiding problems, it's learning to be okay when 90% of things go wrong.

Whether you're building a business, investing in real estate, or carrying a battle no one else can see, this conversation is a reminder that resilience isn't built when life is easy. It's built by continuing when it isn't.

Follow The Red Chair for new conversations every Wednesday with host Genevra Collins, featuring entrepreneurs, leaders, and people whose stories challenge the way we think about success.