20 Under 40: Robert Bierbaum
Meet Robert Bierbaum, 29, CEO at Old Oak Properties and one of our 20 Under 40 Class of 2026 recipients
AS CEO OF Old Oak Properties, Robert Bierbaum represents the third generation guiding the family-owned company’s legacy of excellence in residential living and community building. Raised on job sites and leasing floors, his lifelong immersion in the business shaped a people-first leadership style rooted in authenticity and growth. Today, he is steering transformative projects — including the landmark Legacy Village development — while championing philanthropy, partnerships and purposeful city-building that continues to shape London’s future.
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What is your biggest career achievement so far, or the thing that you’re most proud of?
This past fall, Old Oak broke ground on Legacy Village, the largest development in London’s history. Having the opportunity to work with my brother and bring my father’s vision of Legacy Village to life has been incredible.
When you’re not working, what are you most passionate about?
I love to try and maximize each moment in my life. That means I’m always trying to be doing something. I find London and the programming which takes place in this city — be it parades, events, cultural festivals — is quite good. If it’s a new experience, I’m down for it!
“If your actions feel inauthentic, you need to reevaluate what you’re doing — or how you’re doing it”
On a desert island, what’s the one gratuitous item you’d have to have?
I guess a wine opener isn’t all that useful without the wine?
What advice would you give your younger self?
Listen to the wisdom of others while following your intuition. If your actions feel inauthentic, you need to reevaluate what you’re doing — or how you’re doing it.
What’s the best movie or show you’ve watched lately?
Sinners hands down. It’s a genre of its own!
What’s your guilty pleasure?
My love for decaf espresso. I don’t drink caffeine, but I will go out of my way to find good decaf coffee, sometimes having two or three in a day.
What’s left for you to do, professionally or personally?
At 29, there’s a lot more for me to do. My boat is barely out of the harbour with a wide ocean ahead! I still have lots to learn, lots to explore and lots to experience. I am sure I will make many memories and make a lot more mistakes. But that’s the way we learn to do better and be better next time. 
Interview by Kieran Delamont / Photos by Reid Lucier