The Original Investor - How Ruth Reffkin’s Belief Helped Robert Reffkin Build Compass

A conversation with Robert Reffkin, Founder & CEO of Compass, and Ruth Reffkin, educator, entrepreneur, and the woman who taught him that kindness is a competitive advantage.
A Note from Liza:
Some conversations stay with you long after they’re over.
This was one of them.
Like many people in real estate, I’d admired Robert Reffkin for years. His story is extraordinary, but what always fascinated me wasn’t Compass or the scale of what he built. It was something much more personal.
Every time Robert spoke about success, he spoke about his mother.
Not as a footnote but as the reason. That made me curious.
Who was the woman who raised one of the world’s most influential entrepreneurs? What values shaped him long before Compass existed? What kind of mother teaches a child to dream without limits while also insisting that kindness matters just as much as achievement?
So we invited them both.
What unfolded was a conversation about far more than business. We talked about resilience, single motherhood, reinvention, mentorship, generosity, and the quiet decisions that shape a family for generations.
One of my favourite moments comes when Ruth describes the nightly affirmations she spoke over Robert as a child. Another is hearing Robert explain why, from the very beginning, he wanted Compass to be built by kind people.
I hope you enjoy this conversation as much as I did.