Brian Kosoy from Sterling Organization on how retail became investable again
Brian Kosoy is Managing Principal and Chief Executive Officer of Sterling Organization, which he co-founded in 2007 — a vertically integrated retail real estate firm, and one of the 10 largest private owners of shopping centres in the United States.
He started the firm directly into the financial crisis and spent the following fifteen years in a sector institutional capital was abandoning. Sterling now owns more than 80 centres across 14 to 15 million square feet.
Katie and Brian trace how retail arrived where it is — from the department store to the category killer to the smart phone — and where the growth is now: legacy grocery leases well below market, small shop rents with room to run, and boxes coming free for the first time in decades.
They also talk about why he believes that, by and large, cap rates on institutional-quality real estate assets follow capital flows rather than interest rates, and why he thinks his LPs are more his bosses than limited partners.
About Our Guest
Brian Kosoy is Managing Principal and Chief Executive Officer of Sterling Organization, which he co-founded in 2007. Sterling is a vertically integrated private equity real estate firm investing in retail and consumer fulfillment assets across the risk spectrum in major markets across the United States. The firm owns more than 80 shopping centres across 14 to 15 million square feet, and Green Street* ranks it among the 10 largest private owners of shopping centres in the country.
Originally from Toronto, Brian moved to the United States for law school and practiced in New York City, primarily representing retailers on lease transactions across the five boroughs before moving to the investment side. He sits on and chairs the investment committees for all of Sterling's investment vehicles.
*Source: Green Street Retail Outlook Report, January 2026
About The Re-Up:
The Re-Up is a podcast about the business of raising and allocating capital in private markets — and how that work can be done better. In private markets, a re-up is the decision to recommit to a manager's next fund: the ultimate signal of trust. Each episode is a candid conversation with the LPs, GPs, and advisors who have built exceptional track records — the conversations that usually happen over dinner after the conference, not the ones on stage. Hosted by Katie Fasken, founder of August Advisors, a Toronto-based placement firm connecting exceptional private investment managers with institutional capital.