Ep #240: How This Family Run Business Has Built a Portfolio of 3,500+ Doors and Continues to Dominate the Kansas City Market — with Jesse Worcester

In this episode of the Real Estate Investing for Cash Flow podcast, Kevin talks to real estate and multifamily expert, Jesse Worcester. Jesse is the co-founder of Worcester Investments, a family owned real estate company based in Kansas City, Missouri. He also sits as director of fundraising for capital, building and maintaining investor relationships.

In this podcast, Jesse talks about the market in Kansas and why Worcester Investment decided to move their business from Oregon to the midwest. Jesse describes value investing and the intrinsic value of real estate dependent on things that can be controlled instead of speculation. He explains why he prefers a vertical structure to outsourcing property management and construction. Jesse also offers some perspective on hiring and management, and even recommends books that helped him develop his philosophy on real estate.



“The most boring average markets often times are where you’re going to see your greatest cash flows assuming it’s not a dying city.”

“In everything I’m doing, I want to be doing it thirty years from now so I don’t want to be betting on market timing, there’s a lot of risk factors that come into play when you’re speculating.”

“Most great deals come from two situations: someone making a bad decision or it’s just being a situation that’s very unique where a great deal is able to be had.”

“The driver behind the numbers of the property are the people who are working on the site whether they’re corporate officers or physically on the site.”

“Culture and for us, how we treat individuals has been the single best determinant.”



7:48 Jesse’s background and how his company started

14:18 Jesse explains why they choose the midwest

17:35 What exactly is value investing?

24:16 Vertical management structure of Jesse’s company

29:25 Jesse talks about deals

37:13 Importance of having good underwriting

40:09 On hiring and keeping talents

48:00 Jesse on simplicity

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