Yahya Mahmud describes how he and his wife built wealth through real estate and private lending after starting out as a middle-class couple. He discusses systems, hiring for ownership, and the role of character and risk in investment decisions.
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About the guest
Yahya Mahmud. Yahya Mahmud is a seasoned real estate investor with over 25 years of experience and runs his own single-family office. He started a business in 2017, scaled private lending backed by real estate, and sold part of the business in 2024.
Key takeaways
- Mahmud says his tech and consulting background shaped his focus on systems and sustainable infrastructure that could improve without constant attention.
- He and his wife used a disciplined decision framework, refining it over time rather than making hasty choices.
- He says the business gained momentum when they hired people who act like owners and let them make decisions within clear frameworks.
- Mahmud describes moving from buying, flipping, building, and renting real estate to private lending after a 2015 lending opportunity. They scaled lending in 2017, focusing on private credit backed by real estate.
- He takes a wide view of what multiplies effort: people, time, networks, capital and resources can help an entrepreneur move faster than building everything alone.
- He says he underwrites character before the deal, looking for honesty, shared values, and a willingness to take responsibility when problems arise.
- For lending due diligence, he looks for property security and covenants, walks properties, and considers how long it would take to recover principal if a loan goes wrong.
- His barbell strategy looks for small, risk-adjusted exposures that may produce higher yields while keeping risk contained.
- Mahmud says first-generation family offices may be more hands-on and cautious because their wealth reflects their own work, while later-generation offices may rely more on systems and advisers.
- When presenting an investment, he recommends explaining the risks and mitigation plan, not just the potential return.
Best quotes
"I think what a lot of people overlook is return on leverage and that's what coming from a tech background helped me differentiate cuz I was always thinking of systems."
"we were very very disciplined with the decision-m process."
"Our our business snowballed when we started hiring for ownership."
"So how do you continuously leverage, right? And your return on leverage is exponential and sometimes infinite because you can't build everything yourself."
"when I'm allocating capital, I'm judging and I'm underwriting character before the deal."
"But more importantly in the lending business, it's not about putting the money out. It's about getting the money back then some."
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