In this episode of No Suits Allowed, Connor speaks with Derrick Christy, a self-made entrepreneur whose journey spans from mowing lawns and running a cleaning company in high school to founding one of Indianapolis’s most respected mortgage and real estate enterprises. Derrick opens up about his early years, selling a small cleaning business, taking a corporate job at Prudential to earn his insurance and investment licenses, and ultimately launching his own mortgage firm in the early ’90s. He recounts the pivotal decision to buy his first 60,000-square-foot office building in 1998, the bold leap into a $26 million retail acquisition in Florida, and the stress test of the 2008 financial crisis, sharing candid lessons on cash management, cultivating strong banking relationships, and the importance of maintaining reserves when the unexpected hits.
Throughout the conversation, Derrick outlines how he built his real estate portfolio to nearly 17 properties today, all while simultaneously growing Horizon Property Group (managing retail, office, and multifamily assets), an independent insurance agency, and a mortgage banking operation. He delves into the strategy behind each business line, highlights the value of choosing the right partners and team members, and explains how he balances risk, keeping overall loan-to-value below 50% and maintaining corporate cash cushions. He also speaks to the mindset and daily disciplines that have carried him forward: from disciplined goal-setting and time management to the wisdom he draws from Proverbs, Stephen Covey’s “7 Habits,” and the power of unrelenting faith and purpose.
Connor and Derrick close the episode with practical advice for any entrepreneur feeling burned out or tempted to pivot too soon: nail one business first, write your goals, guard your time, and never lose sight of why you started. Whether you’re a first-time founder or a seasoned investor, Derrick’s story proves that persistence, sound financial controls, and a clear “why” can turn risks into lasting success. Stay tuned for more real-world lessons on No Suits Allowed, and be sure to subscribe so you never miss a behind-the-scenes look at how today’s top executives keep it unfiltered.
Timestamps
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