Justin Kennedy and Toby Cobb.
Toby Cobb and Justin Kennedy
Co-founders and co-managing partners; co-founders and co-CEOs at 3650 REIT and Grass River Property
Toby Cobb was born and raised in the Magic City as the son of famed diplomat and real estate developer Chuck Cobb, but rather than follow in his father’s footsteps, Cobb opted instead for the investment banking route following graduation from Southern Methodist University. For most of his early career, that decision naturally landed him 1,300 miles north in the Big Apple.
Cobb was eventually tapped to co-lead Deutsche Bank’s U.S. commercial real estate division in the late 1990s, which at the time was practically nonexistent. It was at Deutsche that Cobb connected with fellow lead Justin Kennedy, who would become his business partner. The duo essentially built Deutsche’s global lending platform from scratch, which eventually comprised 1,000 employees, 18 offices worldwide and over $30 billion of loan originations per year by the time the pair left the company in 2010.
While Deutsche had its troubles during the financial crisis, it made it through to the other side. “We are perhaps most proud of the way we left it — intact and healthy, since we successfully hedged their book,” Cobb said.
Following their stint at Deutsche, Cobb and Kennedy became co-CEOs at real estate services firm LNR Property, just as the firm was flirting with bankruptcy after the Great Recession. In under three years, Cobb and Kennedy righted the LNR ship, culminating in LNR’s 2013 sale to Starwood Capital for $1.3 billion.
That same year, Cobb and Kennedy founded a new Miami-based development firm, Grass River Property, which focuses on adaptive reuse and transit-oriented projects. Grass River has owned roughly 2 million square feet of properties since its inception, including about 60 percent of the retail storefronts in Coconut Grove, as well as Cocowalk, a more than 200,000-square-foot, mixed-use project in Coconut Grove that Grass River redeveloped in 2020, according to the firm.
In between all that, a few years after founding Grass River, Cobb and Kennedy somehow found the time to establish 3650 REIT with fellow partner Jonathan Roth. The nationwide alternative lending and special servicing firm has had $16 billion in loan originations to date, as well as, amazingly, zero loans that are not current on principal and interest payments, according to Cobb.
“3650 is the culmination of my and my partners’ careers in real estate lending and investing,” Cobb said. “It has been, for sure, the most rewarding career experience yet.”
