Episode 243: Medical Exits and Mortgage Notes: Court Koshar on Surviving 2008 and Thriving Today
Summary
In this engaging episode of "My Life As A Landlord," Dr. Jennifer Salisbury sits down with Court Koshar to explore his fascinating journey from medical practice to private real estate lending. They dive deep into Court’s origin story, discussing how his early property purchases evolved into a thriving private lending business that weathered the 2008 financial storm. The conversation covers the mechanics of his roughly $13M first fund and the ambitious plans for a $50M second fund, highlighting the strategic shifts a forthcoming $5M bank facility will bring. Listeners will also get a sneak peek into the value of high-level masterminds, peer networking, and even some cutting-edge ideas on using isolated AI bots for marketing and security. It is a must-listen for novice landlords, mom-and-pop owners, and larger investors looking to understand the resilience and opportunities in private lending.
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This Week’s Blog Post:
Welcome back to My Life as a Landlord. In this episode, I sit down with Cort Kochhar, someone who knows a thing or two about making major life pivots and building serious wealth. Cort transitioned from a successful medical practice straight into the trenches of real estate and private lending. He started buying rentals at 18, did flips while he was in medical school, built and sold businesses, and eventually scaled back medicine after selling his practice. Today, he still works at Mayo Clinic in Phoenix a couple days a month, but most of his life is focused on real estate and private money lending.
Starting in Real Estate at 18
Cort grew up in a small town in Wyoming and knew early on that he wanted to become a doctor, but at the same time, he wanted to learn how to invest. At 18, while attending the University of Wyoming, he bought his first property because he figured if he was going to pay rent, he should pay rent to himself and have his friends pay him rent. That first house hack worked, and he continued buying rentals everywhere he lived while moving around for college and medical training. Looking back, one of his biggest lessons was understanding tools like the 1031 exchange earlier so he could have consolidated properties instead of eventually owning properties across ten states and filing ten state tax returns.
From Medicine to Private Money Lending
About eight years ago, Cort sold his medical practice to private equity, and the experience wasn't what he hoped it would be. Around the same time, his neighbor Damon Cusick was also exiting a trucking company through a private equity sale. Both were in their 40s, too young to retire, and trying to figure out what came next. They talked about everything from franchises and furniture stores to growing Cort's bakery, but ultimately settled on private money lending. They started with their own money from their private equity exits and grew from a couple million dollars to about $13 million in assets under management, with a goal of reaching about $25 million by the end of the year.
Underwriting the Property and Knowing the Operator
Cort and Damon primarily lend to professional Midwest flippers working with single-family properties and up to four units. Their cap is 65% ARV loan to value, and Cort says they underwrite the property much more than the borrower because they want to know that if a deal fails, they could flip that property themselves. At the same time, when Cort talks about being an investor, his advice comes back to knowing the operator. No matter how good or bad a deal looks on paper, he believes you need to know who is behind it, trust them, or spend the time doing your due diligence to really get to know them.
Learning, Systems, and AI
One thing Cort and I absolutely agree on is the importance of continuing to learn. Medicine taught him how to learn and become a lifelong learner, and that has carried directly into investing and business. We talked about investing in education, learning from experts, and using AI to build better systems. Cort is working on AI agents for marketing and processing so his business can continue to scale without adding more people for repetitive work, while also being very aware of security because of the private information they hold on investors and borrowers. We also talked about how quickly AI changes and how these tools can help articulate the details we need inside our systems.
Invest in Yourself and Keep Learning
As we wrapped up, I asked Cort what he would tell somebody coming out of high school who is thinking about a career, real estate, and how scary all of this can feel. His advice was to find something that interests you and excites you at least a little bit, and then be willing to invest in yourself and your learning and never stop. Things can be scary at first, but with enough practice and hard work, they can become routine. From buying his first property at 18 to medicine, flips, businesses, private lending, and 1912 Capital, Cort's path has certainly had plenty of pivots, but learning and continuing to grow have been there the entire way.