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I’ve learned from working with investors over the years that everyone arrives at real estate differently. Some people spent years building a business before buying their first investment property. Others inherited a portfolio that’s been in the family for generations. Some are investing for cash flow today, while others are thinking about what they’ll pass on years from now. Those different starting points usually shape the way people invest.
I’ve worked with second and third generation property owners who were stepping into a family business. They inherited not only the buildings, but also the investment philosophy that came with them.
I’ve also worked with first time investors who had no interest in following someone else’s playbook. They were building a portfolio from the ground up based on their own goals.
Neither approach is better. They’re simply different.
One client comes to mind who owned a successful operating business and wanted his real estate to support it. Instead of buying investment properties for the sake of owning real estate, he focused on mixed use buildings where he could operate his business on the ground floor while generating rental income from the apartments above. For him, the property wasn’t just an investment. It became part of his business strategy.
I’ve worked with other investors who would never consider that approach. They’re looking for larger value add opportunities, properties that need repositioning, renovations, or operational improvements because that’s where they see the greatest opportunity to create value.
The interesting part is that both strategies can be successful.
The difference isn’t the property. It’s the investor.
That’s why one of the first conversations I have with clients isn’t about square footage or cap rates. It’s about what they’re trying to build.
How involved do you want to be? What role should this investment play in your portfolio? Are you looking for steady income, long term appreciation, redevelopment opportunities, or something that complements another business you already own? The answers usually make the search much more focused.
I’ve also noticed that investors sometimes become attached to a single market because it’s familiar. If you’ve spent your career investing in New York, it may be difficult to imagine opportunities elsewhere. At the same time, another investor may be looking across multiple markets because that’s what fits their strategy.
Neither perspective is right or wrong. The important thing is making sure your portfolio still reflects where you want to go, not just where you’ve been.
Markets change. Neighborhoods evolve. Businesses grow.
The investors who continue building over the long term are usually the ones who take the time to step back every so often and ask whether their portfolio still aligns with their goals.
Those are some of my favorite conversations because they’re rarely about a single transaction. They’re about where the next chapter of the portfolio is headed.
xoxo,
Cyn
