Over 200 Units Before 30 Years Old with Dylan Osmon

August 24

49 mins

Episode Description

In this episode, we sit down with real estate investor Dylan Osmon to talk about what scaling a portfolio looks like when the business starts demanding more than one person can handle. Dylan shares the reality of owning more than 200 units while managing rentals, vacancies, construction projects, and staffing problems at the same time. He explains why hiring has become one of his biggest challenges, why core values matter more to him than experience, and what he has learned from trying to grow without always having the right team in place.

The conversation also explores how Dylan is building toward 1,000 units through a mix of new construction and value-add deals. He shares why simple, repeatable builds work well in his market, how doing more volume has helped him negotiate better construction costs, and why strong relationships with banks have become a major part of his strategy. Dylan also breaks down the decision between using in-house employees and subcontractors, including the hidden costs that can make the cheaper option more expensive once your own time and management are considered.

Dylan also explains why he stopped flipping houses and shifted his attention toward rentals, equity, and long-term cash flow. He talks about growing in smaller markets, protecting cash while still moving forward, and learning from mentors who are operating at a much higher level. More than just growing the number of properties, Dylan shares how his long-term goal is to build the right team and create a real estate business that eventually gives him more freedom, not simply more work.

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Key Topics:

-Why core values matter more than experience when building a team

-How new construction and value-add deals can work together to scale a portfolio

-Why strong banking relationships can change the way you finance real estate

-How to choose between in-house employees and subcontractors

-Why Dylan moved away from flipping to focus on rentals and long-term equity

-How mentorship can change the way you think about debt, growth, and investing

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