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.

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

Chris Smith is the founder and CEO of Ohana Real Estate Investors, an investment firm dedicated to the hospitality and residential sectors, where he has invested more than $4B since inception.

He started the firm in 2009 around a contrarian idea: that the operational complexity of higher-end hotels is not a risk to avoid but the opportunity itself.

Katie and Chris talk about why he treats hospitality as real estate first with an operating business on top, what the demand and supply data say about the luxury segment, why he favours resorts over cities, and how Ohana underwrites its exit before it buys.

He also explains what a set of car keys at 16 taught him about earning a re-up.

About our Guest

Chris Smith is the founder and Chief Executive Officer of Ohana, an investment firm dedicated to the hospitality and residential sectors. He is responsible for all of the firm's business activities and its strategic direction. Under his leadership, Ohana has invested more than $4B across hospitality and residential real estate since inception.

Before founding Ohana, Chris was an Investment Officer at Comprehensive Financial Management (CFM), a leading family office, where he was responsible for the real estate portfolio. He is a member of the Young Presidents' Organization (YPO) and the Urban Land Institute (ULI), a Chartered Alternative Investment Analyst (CAIA), and previously served on the board of directors of Montage International and on several advisory boards for Special Olympics International. Chris holds a Bachelor of Arts from Amherst College.

David Wong is Group Chief Investment Officer of CIBC Global Asset Management, where he leads the investment team across Canada and the US for over $398B in assets. As head of Total Investment Solutions, he also oversees more than $100B in managed solutions.

He has more than 27 years of experience, beginning as a research analyst at Russell Investments.

Katie and David talk about where private markets fit inside a bank-owned platform, why Canadian investors remain underexposed to alternatives, the regulatory ceiling that shapes how much can go to privates, and what it takes to earn a re-up at scale.

He also explains the free coffee test — and why performance is only part of what a manager sells.

David Wong is Group Chief Investment Officer of CIBC Global Asset Management, where he oversees the investment team across Canada and the US and sits on the firm's executive leadership team. In that role he leads the management of over $398B in assets spanning managed solutions, fixed income, equities, and alternative investments. As head of the Total Investment Solutions team, he directly oversees the portfolio management of more than $100B in managed solutions, and he is a member of the CIBC Family Office Leadership Team, providing institutional asset allocation advice to ultra-high-net-worth individuals and families.

David joined CIBC Global Asset Management in July 2011, serving as Managing Director, Investment Management Research and later as Chief Investment Officer, Managing Director and Head of Total Investment Solutions before taking on the group CIO role. He has more than 27 years of industry experience in New York and Toronto; before CIBC, he was a Senior Research Analyst at Russell Investments, covering a broad spectrum of fixed income strategies for institutional and retail clients. David holds an Honours Bachelor of Commerce from McMaster University, is a CFA Charterholder, and holds the Financial Risk Manager (FRM) designation from the Global Association of Risk Professionals. He serves on the boards of the CIBC Foundation and the Oakville Community Foundation, chairing and co-chairing their respective investment committees.