#329: Why Your First Deal Doesn’t Need to Be a Home Run with Justin Dragone

In this episode of The Multifamily Wealth Podcast, host and investor Justin Dragone shares the story of his first real estate deal—a three-unit property in Manchester, New Hampshire, acquired in late 2023. Though not a 'home run,' the deal served as a foundational experience that helped him gain confidence, learn the ropes of property management, and build momentum for future investments. Justin financed the $500,000 purchase with a 75% LTV conventional loan from a local bank, made minimal improvements post-closing, and hired a property management company due to the 60-minute commute from Boston. The property appreciated to $650,000, allowing him to refinance and pull out half his equity to fund a larger seven-unit deal. The episode emphasizes that first deals don’t need to be perfect—just functional and confidence-building. Justin debunks myths about young investors facing financing hurdles, explaining that local commercial lenders prioritize the asset over borrower history, making it accessible even for early-career investors with solid credit and a down payment. Key takeaways include: Your first deal doesn’t need to be a home run—just a working deal that builds experience; local banks often offer more flexible underwriting than conventional mortgages; managing a small property remotely is worth the cost of a property manager; and the real estate journey begins with execution, not perfection. The episode concludes with a strong message: focus on raising the floor of risk, not chasing outsized returns on your first deal.