Why Slow and Steady Wins in Healthcare Real Estate with Dipesh Sitaram

Real estate does not have to produce a home run every time to make sense.

For Dipesh Sitaram, years of investing across different real estate sectors led him back to the field he understood best: healthcare.

Dipesh has spent 20 years in healthcare. That experience gave him a close look at how practices and surgery centers operate, what their real estate needs look like, and why many healthcare tenants are willing to sign longer leases.

He tells Dave that the COVID period became a real litmus test for him. While he watched other areas of real estate struggle, his experience in healthcare looked different. Healthcare tenants kept paying rent and business carried on.

That helped shape a simple philosophy: real estate is a long game.

Dipesh is not focused on speculative deals that need huge appreciation in a short time. His preference is the kind of steady approach he describes as hitting doubles rather than expecting a home run every time.

He also walks through one of his favorite properties, a 20,000 square foot Midwest surgery center. After revitalizing the building, the tenants saw enough value in the improvements to enter into a long term lease. The property remains in the portfolio.

In This Conversation

• Why Dipesh focuses on healthcare and healthcare adjacent real estate
• What his experience in hospitality, multifamily, and condos taught him
• Why COVID became his personal test for real estate stability
• How revitalizing a surgery center helped strengthen the tenant relationship
• Why higher interest rates, lower tenancy, and higher operating costs created problems in multifamily
• Why investors should study both the property and the operator
• Why subject matter expertise, experience, and a clear exit plan matter to Dipesh

About Dipesh Sitaram

Dipesh Sitaram has spent 20 years in healthcare and brings that operating experience into real estate. His current holdings are mainly specialty surgery centers, with investments concentrated in the Midwest and Central Texas.

He describes his approach simply: slow and steady wins the race.