Why Boring Wins in Real Estate With Alan Fruitman
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Episode Description
On this episode of the On The Rise Podcast, host Jeremy Dyer talks with Alan Fruitman, founder of 1031tax.com and president of Real Estate Foundation, who has spent 33 years specializing in single-tenant, triple-net-lease real estate. Alan explains why chasing yield means chasing risk, and why quality — the best location and a national-credit tenant like McDonald's or Chase — builds lasting wealth. He breaks down why truly passive income is real, how to avoid the emotional trap of the 1031 exchange's 45-day window with his "green light day" strategy, which tenants are AI- and Amazon-proof, and why "boring" singles and doubles beat swinging for home runs. A grounded conversation on preserving wealth.
Summary
A niche built early became a 33-year career.
Starting in 1993, Alan differentiated himself by helping out-of-state owners sell property. Those clients led him into 1031 exchanges, then to a client's question — "can you help me buy a triple net property?" — that redefined his entire career.
Chase quality, not yield.
Alan's core principle: "When you chase yield, you're chasing risk; when you chase quality, you're chasing longevity." The best-located property tends to get better over time, attracting top-tier tenants and sustainable, rising rents.
A quality tenant in a great location is the recipe.
Joe's Burger Shop offers a higher yield but takes a second-tier location; McDonald's or Chase takes the best location and brings far stronger credit. Pairing a national-credit tenant with a premier location is a repeatable formula for long-term success.
Truly passive income is real.
The biggest misconception, Alan says, is that people "don't believe it exists." Under an absolute triple-net lease, the tenant pays all taxes and insurance and handles all maintenance — even replacing the roof without telling the landlord — making it 100% passive, unlike apartments or shopping centers.
The 45-day window is a worst-case scenario, not a plan.
Investors who wait until day 40 or 45 of a 1031 exchange to choose a replacement get rushed into bad decisions. The two things you need are time and information — and both come from working with a specialist long before you sell.
Act on the "green light day."
The signed sale contract means little; the magic date is when the buyer's contingencies are removed and the deposit becomes nonrefundable. Alan negotiates a large gap after that day, lines up replacement properties in advance, and aims to close well before day 45 — making the exchange "bulletproof."
Pick AI- and Amazon-proof tenants.
Location is permanent; the harder question is who survives. Amazon can't hand you a $10 meal while you're driving, and can't put tires on your car — so restaurants and tire stores endure. (Electric cars even burn tires faster, increasing demand.)
Boring wins — aim for singles and doubles.
Alan's baseball analogy: swinging for the fences might land a home run, but triple net is a reliable single or double that keeps you from striking out. Consistent passive income beats chasing the shiny high-flier.
Resources
Book: The NNN Triple Net Property Book
Website: https://1031tax.com/
