Ep. 039: Lessons from the Leap: John Casmon on Leaving Corporate for Real Estate
In a candid conversation with Dustin Miles, multifamily investor, coach, and creator of the Multifamily Mastery program, John Casmon shared the journey that took him from corporate marketing roles to leading multimillion-dollar real estate ventures. His story is packed with insight for seasoned investors, aspiring entrepreneurs, and anyone curious about bold career pivots rooted in strategy, resilience, and community.
Breaking Free from the Corporate Mold
John began his career in corporate America, holding marketing roles at major companies like General Motors. Like many, he believed a “good job” meant stability—until mass layoffs and bankruptcies proved otherwise. The upheaval at GM and later at a Chicago marketing agency exposed how fragile traditional careers can be and sparked his search for financial independence.
Discovering Real Estate: The Spark and the Struggle
Real estate emerged as a recurring opportunity, even if the timing wasn’t ideal. “This was Detroit in the middle of the Great Recession,” John recalled—a hard place to start acquiring property. It wasn’t until he moved to Chicago that he took action, purchasing small multifamily properties.
The early days brought plenty of hard lessons: missteps in property management, unexpected tenant issues (including one who blamed ghosts for unpaid rent), and a crash course in problem solving. But those experiences built the foundation for everything that came next.
The Power of Mentorship and Community
Mentorship proved pivotal. After attending a high-pressure real estate seminar, John and his wife ignored the sales pitch and instead spent hours in the public library mapping out their vision. That intention led them to the right mentor—someone who opened their eyes to raising capital for larger deals.
It was a game-changing shift: “The next deal we did was actually 192 units… all through the power of syndication and networking.”
Relationships continued to fuel John’s growth. His podcast, conference networking, and willingness to ask better questions helped him build partnerships that accelerated his scale and confidence.
Asset Management: Being the CEO of the Property
John stressed that owning real estate isn’t passive. Asset management is where expertise shows up—or crumbles. He likens the role to being the CEO of a business: overseeing financials, ensuring the business plan is executed, and aligning teams around measurable goals.
Weekly calls with property managers, reviewing KPIs like occupancy and conversion rates, and pushing for clear action steps are central to his approach. His warning to investors: hiring a property manager doesn’t mean going hands-off.
“You are the CEO. You are accountable. This is not a set-it-and-forget-it situation.”
Coaching: Building Confidence Through Reps
John now coaches investors through his Multifamily Mastery program, blending one-on-one and group support. His philosophy is rooted in preparation: confidence isn’t something you pretend—it comes from doing the work repeatedly.
He draws a distinction between mentors and coaches: mentors show you a single path; coaches help you uncover your best path, shaped around your strengths and goals.
Investment Philosophy and Market Outlook
With a portfolio across Cincinnati, Columbus, Louisville, and parts of the Southeast, John focuses on value-add multifamily opportunities, emphasizing flexibility and long-term performance. He believes uncertain times can create outsized opportunities for investors willing to stay disciplined and strategic.
Final Thoughts
John’s passion for helping others is unmistakable. He encourages investors to download his free guide, Seven Questions You Must Ask Before Investing in Apartments, designed to help avoid common mistakes and approach deals with clarity.
This conversation wasn’t just a success story—it was a roadmap for navigating multifamily real estate with integrity, adaptability, and a commitment to continuous learning.
