From 10 single-family rentals with almost no cash flow to 1,500 units and a firm that's outperformed the market through the worst multifamily downturn in a decade — this week we sit down with Gary Jonas, CEO of The How Group, a Philadelphia real estate powerhouse spanning development, construction, and property management.
Gary walks us through the entire arc, starting with house-hacking his way into ownership right out of La Salle University in 1994 — a story that ends with him moving back in with his parents after his roommates couldn't handle living with a landlord who kept straightening up the house. From there he built up 10 single-family rentals and learned the hard way that owning real estate and getting paid by real estate are two completely different games. That lesson — equity isn't cash flow — is what pushed him to sell off those 10 houses and roll everything into multifamily, where the math actually worked.
He gets specific on how The How Group is buying distressed multifamily assets today for less than what they cost to build seven years ago, using a 50-unit building across the street from Manayunk's movie theater as a real, live example. He breaks down why he takes fixed-rate debt even when it costs more upfront, why he underwrites every deal assuming rents go down 10% instead of up, and the exact framework he uses to "bulletproof" a deal against interest rate swings, rent risk, and bad execution — the same discipline that let him protect every investor's principal through 2019–2023 while giving his own profits back to make it happen.
We also get into the real mechanics of running a 30-year business partnership with the same two guys — including a $500,000 loss on a failed technology investment that nobody blamed anybody for — and Gary's simple, slightly uncomfortable test for figuring out whether you're even wired to be someone's business partner in the first place. He closes out with why giving away his entire investment playbook for free, roadmap and all, has been one of the best business decisions he's ever made.
If you're building wealth through real estate, thinking about your first multifamily deal, or trying to figure out whether cash flow or equity should come first, this is a masterclass from someone who's done it at real scale — and been honest about what it cost him to learn it.
CHAPTERS
00:00 – Cold open: the giver vs. taker philosophy that built a real estate empire
02:15 – Sponsor: Property Management Redefined - https://gopmr.com/
03:40 – Meet Gary Jonas, CEO of @thehowgroup1496
06:10 – Buying his first property at 22 (and moving back in with his parents)
10:20 – The How Group's sweet spot: why 50–150 unit buildings
13:45 – Why 10 single-family rentals built equity but zero cash flow
19:00 – Equity vs. cash flow: the shift that changed Gary's entire strategy
24:30 – How Gary builds an investor roadmap from scratch
29:15 – From electrician's kid to mortgage company founder
34:50 – Inside The How Group: development, construction, and property management
39:20 – Buying below replacement cost: the Yarn Factory deal
44:10 – The 30-year partnership test (and the $500,000 mistake nobody blamed)
49:30 – Bulletproofing real estate: interest rates, rent risk, and execution
53:00 – Why Gary gives his entire playbook away for free
CONNECT WITH GARY JONAS
Website: https://howgroup.com/
LinkedIn: https://www.linkedin.com/in/gary-jonas/
YouTube: https://www.youtube.com/@Gary_Jonas
Investing with The Howe Group: investments@howegroup.com
CONNECT WITH BRICKS AND RISK
Bricks and Risk is a podcast dedicated to real estate, insurance, and building your business, hosted by Sean Mooney and Tim Garrity. Join us as we share our own business-building journeys along with wisdom from a network of local and national experts.
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