Freedom doesn’t come from a single lucky deal; it comes from stacking repeatable wins. John Brandon joins us to share how a childhood spent around apartment complexes turned into a 700+ unit portfolio, a hard-earned education in debt cycles, and a new focus on smaller, faster-moving multifamily that can outperform jumbo syndications.

We walk through the first 16-unit JV in Greenville, North Carolina—how under-$500 rents doubled after deliberate turns, why local knowledge mattered, and what changed once interest rates jumped. John breaks down a tough Baltimore exit where investors were made whole but sweat equity vanished, then explains the portfolio pivot: sub-50-unit deals with mom-and-pop sellers, tighter operations, and clearer value-add paths. You’ll hear how $600k in soft capital evaporated two weeks before close, why that pushed him toward JV structures, and how he uses LinkedIn and warm outreach to attract investors without becoming “the cousin with the stock tip.”

This conversation is also a masterclass in recurring revenue. John’s background in payments taught him to love predictable cash flow, which now shows up in apartments and a franchised insulation business designed for steady margins and simple operations. We compare GP vs LP roles in real estate syndications, unpack out-of-market investing due diligence, and detail the debt choices—bridge vs agency—that can make or break an otherwise solid plan. If you’re weighing small multifamily against big syndications, or eyeing a second engine with a Main Street business, this episode gives you a practical roadmap grounded in real numbers and real pivots.

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VCap Real Estate Podcast