Podcast

Zen and the Art of Real Estate Investing with Jonathan Greene

289: Finding a Better Way to Build Cash Flow with Jon Wells

On this week’s episode, Jonathan welcomes Jon Wells, a real estate matchmaker, syndicator, and longtime realtor with A Better Way Realty and managing partner at Alpha Network—for a candid look at what actually builds durable wealth.

Jon traces his journey from early “fix-and-flips” to higher-conviction “fix-and-holds,” and ultimately to group homes leased on commercial-style terms. He explains why patience, operator quality, and underwriting discipline matter more than shiny objects, and how aligning with the right partners turns headaches into hands-off income. As the conversation unfolds, they unpack contractor pitfalls, slim-margin flips that turn into flops and the relief of triple-net-style leases where the business, not the landlord, handles the day-to-day. Jon shares why he prefers renting large, lightly modified homes to sober-living/mental-health operators (versus carving up houses), why meeting new operators is the hardest part of this niche, and how option agreements can create shared upside. They also dive into passive vs. active choices, due-diligence checklists for syndications, and the value of investing in what you truly understand. Listeners will come away with a calmer, longer-term lens: start with who you trust, de-risk with questions that reveal how an operator thinks, and don’t mistake speed for progress—especially when cash flow and sleep-at-night returns are the goal.

In this episode, you will hear:

Why slim margins turn flips into long, stressful holds—and how to avoid it
The group-home model Jon uses: bigger homes, egress and safety upgrades, and commercial-style leases to vetted operators
Triple-net thinking for residential assets: fewer calls, clearer responsibility, steadier income
Trust and due diligence: the questions that de-risk syndications and funds—and when “no answer” means “no deal”
Why investing in what you actually know (and who you truly trust) beats chasing neon “opportunities”
How to choose between passive and active plays based on temperament, skills, and season of life

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