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Join me, Nik (@CoFoundersNik), as I sit down with Robert Leonard (@therobertleonar), a real estate investor, entrepreneur, and podcast host with over 15 million downloads, to talk about the crossroads between real estate investing and small business acquisition (SMB).

In this episode, we explore one of the biggest questions for aspiring entrepreneurs:Should you build wealth through real estate or by buying a small business?

Robert breaks down both paths, drawing on his experience as a CFO in the home services industry and as a multi-property investor. He shares how he started with house hacking, why it’s the best low-money strategy for beginners, and why he’s now selling off his rental portfolio to reinvest in higher-growth business ventures.

Robert also explains the mindset shift that helped him move from being an investor chasing properties to a founder building scalable cash flow. His take on risk, leverage, and capital allocation will completely change how you think about building wealth.

Questions This Episode Answers

Is SMB acquisition or real estate investing better for beginners?

What is house hacking, and how can it fund your business?

Why is buying a small business often a better move than owning a few rentals?

What’s the difference between wholesaling and subject-to investing?

Which home services businesses are truly recession-proof?

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This week we covered: