Our first guest is Robert Reffkin, founder, chairman, and CEO of Compass International Holdings, the multi-billion dollar company that now leads the largest residential real estate network in the world, spanning more than 120 countries and bringing together iconic brands, including Sotheby's International Realty. But that is not why I invited him. I invited him because every time I hear Robert talk about success, he talks about something else: his mother. Her resilience and her sacrifice, her unwavering belief in what was possible helped shape the leader he would become. And that is what today's episode is really about. Not just building a great company, but building a great life. Not just achievement, but gratitude. Not just ambition, but the people who make our ambitions possible. Later in the episode, you will also meet Ruth Reffkin, whose own story of reinvention, purpose, and continued impact is every bit as inspiring. I'm Lisa Kaufman, and this is Smart Women Big Deals.
Hello, Robert. Welcome to Smart Women Big Deals. Thank you so much for being here and for being so supportive of our podcast from the very first time we spoke about it in Toronto. It's great to see you again and I can't wait to see you at the G&
Same here. So, let's get started. When people speak about your success, they always speak about Compass. When you speak about your success, you almost always start talking about your mother, Ruth Reffkin. Tell us why that is.
Well, look, my mom, to me she's a superhero. She was a single mother. She was disowned by her family for an interracial relationship. And it was really just the two of us. And I saw her just make so many sacrifices for me. I saw her dream big for me. I saw her believe in me when we applied to high school or college. And even just think, I said we applied, right? She was just with me every part of the way. And she was an entrepreneur. She has been an agent, life insurance agent and then real estate agent my entire life. And I just saw her as an entrepreneur who had rejection in certain parts of her life professionally or personally but just kept moving forward. And seeing her as an entrepreneur every day made me want to be an entrepreneur.
Yes. And also she was a broker. She's been a broker for over 30 years and she has a team, the Ruth Reffkin team and yeah, it's amazing to watch.
In your best-selling book, No One Succeeds Alone, which I recommend to every aspiring entrepreneur. I loved it. You talk about several mentors who changed the trajectory of your life. Can you tell us about them?
One of my mentors which I'd really highlight is a gentleman named Vernon Jordan. He was actually on more Fortune 500 company boards than any person ever. He's on so many boards that they had to call it a new rule called the Vernon rule where you can't be on over a certain amount of boards for public companies at the same time. And he was Bill Clinton's best friend. He worked in, he was head of the transition committee which brought all of the appointees on in Bill Clinton's first term. He worked at an investment bank where I was working there and he also was a senior adviser at a major law firm. And so he really, he was political and in business and he told me a few things that I'll never forget, many actually, but he said, 'Robert, may your dreams be your only boundaries.' First principle of the entrepreneurship principles, the Compass International Holdings entrepreneurship principles is dream big. Your dreams are going to be the cap to your potential. You'll never be bigger than your dreams. So you have to dream big. It kind of comes from that. The second thing he shared, he said, 'Robert, I encourage you to apply to be a White House fellow,' which I did, where 11 professionals in their late 20s to early 40s every year are selected to work as a senior adviser to a different secretary in the government. So, Secretary of Treasury, Secretary of State. I was a senior adviser to the Secretary of Treasury. It's a one-year program and every day you have lunch with a different global leader. It's a great program. He said, 'Robert, I believe all young professionals should get exposure to both the public sector and the private sector because the skills you'll develop, the experiences you have, the relationships that you attain will be transferable to either sector you choose.' And I think that turned out to be true.
Totally agree. Your mother once shared that when you asked her to help recruit agents for Compass, you told her you wanted people that were kind. Now, that really resonates with me. I love it. But that is not the way most CEOs speak. Why was kindness so important to you from the very beginning of Compass?
I think for me it was just like I didn't want to be around people that aren't kind, right? We had all these incredible investors, like 11 billionaire families, more than 10 big real estate developers. And I asked their agents if they would consider, you know, launching this company with me. And they said in order to launch this company that they would want to see a broker who's a top 10 broker that has experience in both new construction and resale who would bring credibility. And so I asked them all to give me three different names and there was only one person on everyone's list. It was a gentleman named Leonard Steinberg. He is really collaborative, very very kind, very giving to others and it became clear to me that brokers are looking for a culture that's collaborative and so it's always been really important to me. I think it's good on a human level, but also important on a professional level. You may not, you may by saying no to the wrong person. You may have less, you know, people today, but you have more tomorrow. I call them energy vampires, right? People that suck the energy from others. You just can't have those kinds of people around.
I can't agree with you more. That's the way I grew my company, too. But there are not too many of us that believed in that all the way back then. When you look back on your life, what is the smartest big deal you have made? One that might have or might not have anything to do with your career.
Well, I mean, I'm absolutely certain it's my wife.
I knew you were going to say that.
Yeah. I mean, it's and I think I didn't understand how important it was at the time. I would not have been able to sustain myself at Compass International Holdings all these years if it wasn't for her. I would not be, I mean just so much would not have happened. She's an executive coach by practice. She worked at Goldman Sachs before but she really, she's a professional coach in entrepreneurs and so she's a thought partner. She's a coach. She goes to open houses with me every Sunday to support.
Love that. And you bring your kids, too, which I think is fantastic.
We're all in, right? We the real estate professionals, you're the client. We work for you, not the other way around. And it's my obligation to build a company that can help you grow your business. So you have more income to support your family and also more time to be with your family.
I love that. Well, Warren Buffett did say that the most important decision you can make as an entrepreneur is who you marry. So you did very well obviously. You famously ran 50 marathons in 50 states to raise money for charity and on top of that you brought your mother along as your race manager. How did that come about?
So I was 25 when I started. It was five years, one a month and you know, one in every US state and I was at Goldman Sachs and I wanted to give back and I was very frustrated. I felt like people weren't giving back as much they could, as much as they should, and I wanted to raise money for nonprofits that help students that are young realize their dreams. So, I created this idea of calling it Running to Support Young Dreams. It's running to support young dreams dot com. And I announced to everyone, I'm going to raise a million dollars to support these different nonprofits, some that I went through as a student when I was younger and a charter school I founded and a nonprofit I founded called New York Needs You that helps students who are first in their families to go to college across all different types of backgrounds. It helps give them the career development, college support and two summer internships to realize their dreams. So that was the idea. But I'll never forget when I decided to do it. I sent this email out to everyone in my network and one person wrote back, a very successful person at McKinsey, a company that I started at out of college. He was a top three person there. He said, 'Robert, you know, you're raising money for 50 marathons. That this is great, but what if you get injured and you can't finish? You're raising money and what if you get injured and you could fail?' And I'll never forget like that idea, the idea that you can fail and to not try something because you can fail. It's just that is, you know, I see it sometimes on, you know, in the company people scared of failure and that's why they don't try things. Like it kind of shows you that the biggest barrier to your talent and your dreams it could be yourself because you're too scared to try something.
But that's a typical way, I hate to say it, that a lot of management consultants think because they don't build anything, they come in and get hired. So no offense to McKinsey but I've known a lot of people that have worked there. Just letting you know.
Might be controversial, but it's true.
So, I want to go back to the marathons because it took you how many years? Four years to complete that.
It took four years to do 49. I was going to do the fifth one, and then there was Hurricane Sandy in New York, so I had to delay it. It was 5 years, but I was doing one a month for that period of time.
Wow. And your mother was at almost all of them, but I heard that she was bummed out that she missed out on Hawaii, right?
Yes. Yes, that was a long.
You have to take her back to Hawaii. I think you owe her that.
What is something your mother did that seemed completely ordinary at the time, even when you were a child, that turned out to be one of the greatest gifts she ever gave you?
I mean, it's kind of the similar theme. I think she gave me the gift of believing anything is possible, right? I'll give you an example. We applied to, we got a book, we saw it on TV. He had said billions of dollars get wasted every year for what is it, for scholarships, and buy this book because people aren't applying and not all the scholarships got applied for. And so we bought the book and it had, I don't know, thousands and we looked at everyone that seemed like it could fit my background. I'm Jewish, I was black, I'm from California, I was a DJ so I was entrepreneur and we applied for all of them. It was hundreds and I think we only got, there's like seven or so, maybe a little more but we got those right. And so she taught me through countless examples like that. It's not the shots that you miss, it's the shots that you get. It doesn't, and you can't get something you don't try for. It doesn't matter if you fail. Like I literally do not care at all about failure at all. I mean the history of Compass, you can look at the outside like all like this happened, that happened, that happened. But or even my life like you, I applied to dozens of colleges. I only got to one that I want to get into which is Columbia. I applied out of college to a lot of different places. Only gotten to a few. One was McKinsey at a same kind of thing at business school. It doesn't matter all things you don't get. It's just you got to try.
Well, she was an entrepreneur and entrepreneurs, this show originated because I wanted to show that entrepreneurs learn more from their failures than anything else and they learn and they pivot and they never give up. And that is an example of your mother's life, of resilience, and of what you've done, too. So, it's been a real pleasure. I know you're super busy. So, I'm gonna let you go and I look forward to seeing you at the G& I'll be there for sure.
Okay. Thank you so much, Robert. Bye. We got you in and out because I knew you had a short amount of time. I could have talked to you for another hour.
I'm really glad to have done this and I can't wait to see you and thanks for your leadership and your passion and positivity. You're such a great person and role model. My mom loved spending time with you also. So, thank you.
And now it's my great pleasure to introduce you to Robert's mother, Ruth Reffkin.
Ruth, welcome to Smart Women Big Deals. I am so happy you're here.
Thank you so much for inviting me. I'm really looking forward to our conversation.
I've been looking forward to it as well. You have lived an extraordinary life filled with purpose and reinvention. And not to mention that you inspired your son Robert to create a multi-billion dollar startup called Compass. But today I really want to explore the story behind the story of Ruth Reffkin. Shall we get started?
Okay. Tell us about the family you grew up in.
Well, I was born in Jerusalem in Israel in 1945. They raised me very Jewish but not religious. We came to America in 1952, moved to the Upper West Side of Manhattan, and that's where I grew up. So I spent all my childhood up until I went to college living on the west side of Manhattan and I went to a school called Ramaz School which was considered to be a modern orthodox yeshiva. My father was, even though he left the traditions in a lot of ways he also kept a lot of the traditions and it was a very patriarchal household. He was a very authoritarian father and I was actually kind of scared of him. He never raised a hand to me but when he raised his voice I got really scared and so I grew up kind of in a very limited way, you know, even though I grew up in New York City I didn't have a lot of freedom to explore. So I was very curious about the outside world.
What type of little girl were you?
I think I was always kind of very willful and that was part of a problem in my family. That was defined as being bad. As I grew up, I became rebellious, but even when I was younger, I just wanted to do what I wanted to do. I know I threw a lot of tantrums when I was young.
And but I was also very curious. I was really curious about the world. For a while I thought I was going to be a scientist. I was very interested in how things worked. And I also, I was friendly. I liked people. I wanted to have friends. Having friends was very important to me.
I had an older sister. She was two years older than me. She was the ladylike one and I was the tomboy, so we were very, very different from each other. But I loved her very much. She was a good sister to me until as we got older things got separated out in my family. We could talk more about that later, but she was 2 years older than me. I always wanted to be her. I always wanted to be able to do all the things she could do. I wanted to be part of her teenage group, you know. I was pretty typical younger sister that way.
How did you end up in Berkeley, California?
Well, so that's what happened after I left home. So once I left my parents' home, I started the process of trying to become myself, figure out who I was, what kind of life I wanted, what my belief systems were and when I graduated high school in 1963, so went right straight into the 60s and I embraced all of it. I did just about everything you can imagine one would do in the 60s and got myself into a little bit of trouble but I also met somebody wonderful who I married back then and so in 1969 we went to Woodstock and a few months later we went to Berkeley California and I think a lot of it was because that's what everybody was doing then. We wanted to leave the dark cold hard life in New York City for California dreaming, you know, there was the song, you know, and off we went.
So, you were the flower child of the 60s then.
I wasn't as much of a flower child. So, there was a differentiation back then between the people who are political leftists and the ones who are just kind of hippie-dippy flower children. I was always very political. I was very much a leftist. I was very much against the war. I marched for civil rights. And I became a feminist. I became very much involved in women's liberation, going to meetings, marching, demonstrating, all that stuff. So I was more on that side. There were what we call the hippies and then the yippies.
Okay. Tell us about your journey as a single mom.
So we moved to Berkeley in 1969. Robert was born in 1979. So those 10 years were very very formative in my life. Now I was pretty much far enough from my parents that I wasn't just operating in rebellion. I was more trying to become who I wanted to become. I had solid friendships and relationships that I was developing.
Right. But you were married when you arrived in Berkeley, right?
We were married. I was married to Gene Reffkin. That's where we have our last name from.
And together with three other friends, four other friends, well, three, the five of us all together, we bought a house. It was a fourplex. It was a wreck, but we bought it and we turned it into the house that supported many of us in many ways for the years to come. And so that gave me a lot of stability, my relationship with Gene gave me stability, my friendships, but also my marriage changed during those years. So we end up realizing that we were more brother and sister than husband and wife and we were fortunate enough that we were able to allow our relationship to transition in that way without anybody getting hurt actually. So during that time I had few relationships which ended up with a relationship with Robert's father which was honestly one of the stupidest things I've ever done in my life. He was not a good candidate for parenthood or even to be in a relationship but there was a very negative relationship. It was very dysfunctional. He was abusive. So when I found out I was pregnant with Robert, I was actually in the process of breaking up with him. And I had had two previous planned pregnancies that I miscarried. But when I got pregnant with this pregnancy, I thought, 'No, there's no way in the world I should have a baby with this guy.' And so I wasn't going to. But then at the last minute, I changed my mind. And I decided as I said to my friend half jokingly, I want to kill the father, not the kid, you know. So, and I didn't kill him. And I didn't kill either. So, I had Robert. And having the house and now having a child changed me profoundly. I had responsibilities. I had more stability. And I became more ambitious as a person. You know, I wanted to provide a lot for my son. So, you know, those 10 years, like I say, very formative. A lot of things happened. I came out of it with a very much stronger sense of who I was and what I wanted to make of my life.
Did that affect the relationship with your family?
Well, so Robert's father was black, which is why Robert's half black, half Jewish, and I like to say all black and all Jewish, but my parents were not amused from where they came from. And actually, they cut me off totally. I was disowned and disinherited. My father never talked to me again until the day he died.
After he died, my mother and I developed somewhat of a relationship, but she refused to meet my son and she never met him until the day she died.
Was it because, you know, the father wasn't Jewish or because the father was black?
Well, they would claim that it was because he wasn't Jewish, but you know, I know that if he'd been the child of a black Jew they would not have been pleased either. So, Robert was raised, he was born around 47 years ago and times were much different then for biracial kids. What was your worry while he was growing up?
Well, you know, I had the same worries that any mother of a young boy of color in America has. I was very realistic about it. I didn't come to that decision, you know, like I said, I almost didn't have him because I was worried about all that. So, I made a commitment in having him that I had to raise him in the way in which he would be able to survive and thrive in America. Living in Berkeley, California was probably one of the best places to do that. Berkeley has always been a very liberal town. I knew I wasn't moving to Mississippi with him, you know, but still, you know, racism is racism everywhere in the world. And we had a lot to overcome, but what I wanted for him is to not be angry, to have a positive sense of himself both as a Jew and as a black man in America. And I worked real hard on that. There were a lot of things, very conscious decisions I made to make that happen.
He has spoken about at times feeling like he didn't belong to any community. How did you help him with that?
Well, it was easy for me to be Jewish and to give him all that. To make sure that he had especially black male role models in his life was very important. I did that through friendships and again very consciously, you know, I had to reach out, make myself vulnerable sometimes, people didn't want to befriend us but I did find and develop a community around us that was very diverse. I also made sure, you know, you make plans for your kids. Where do you send them to school? Where do you send them to camp? All that and it was always very conscious in terms of the diversity of the people that he'd meet. You know, you can't protect your kids from everything, you know.
But I think that there's a lot of benefit that he gained from that as well because Robert now, if you see him in the world, he can really operate in just about any environment. He knows how to make himself heard and to listen and to understand. He's very culturally sensitive. You know, he really wants to understand the people around him, where they're coming from. He's very respectful of differences. You know, Berkeley, a lot of people laugh about it because it's almost, you know, a cliche in a certain way, but it is a town that's on the one hand very politically correct, but also it means that people do mix and get to know each other and have a value system in which I think somebody like Rob is able to thrive in the long run.
Well, people often speak about him as being incredibly resilient, and that probably has a lot to do with the way you raised him in that environment.
Well, I believe in resilience a lot for myself. I'm very resilient. Consciously so, you know, I made decisions in my life including having Robert, my parents turning their back on me which meant that I had to function in certain ways in order for us to survive well and that resilience is a key to that. You can't just let everything get you down.
Did you ever believe in Robert more than he believed in himself when he was a teenager or a child?
You know, I'm not sure if I could say more, but I do think that a lot of his self-confidence was very purposefully I injected in him.
I at a certain point in my life I became very aware of the power of affirmations.
Personally for myself there's a great book by Louise Hay, How to Heal Your Life and Yourself I think is what it's called, whatever, but she talks a lot about affirmations. What really clicked in me which I carried over to my parenting was she said that, you know, watch what you listen to the last thing before you go to sleep at night because whatever you take in at that point your subconscious mind takes in in an unfiltered way. It doesn't know how to say yes or no to judge it. So for instance she says don't watch the news, you know, because your subconscious thinks the world is constantly at war. You know that. So I started giving Robert affirmations as I was tucking him into bed at a very young age. And one of the things that she said which I really took to heart is an affirmation has to be in the present. It can't be you're going to be happy. It has to be you are happy because otherwise you're always going to be and you never get there. So I told him a lot of things about himself that he has and is entitled to and belongs. I mean a lot of that every night and I really believe it took hold.
I say affirmations every morning. I say my prayers, meditate and I say and sometimes write them down too. They work. They totally work. The parents' voice saying that to a young child as you tuck them in at night is incredibly powerful because even as adults we carry our parents' voices inside of us. And I know I carried very negative voices because I was told that I was a problem, that I was a bad person, that I was going to always be in trouble. My father used to tell me, 'You're going to end up in the gutter.' Literally, he'd say to me, 'You're going to end up in the gutter.' So I still carry some of that inside of me. I mean all these years later I remember the tone of voice with which he said it. So I definitely did not want Robert carrying those things.
Was he ever rebellious? Did you ever have to use tough love with him?
I had to use tough love but not necessarily because I believe in tough love period. As a sales manager I was a tough love sales manager. I think the world is tough too.
I mean the world, it's tough out there, you know. It's tough out there. You have to be tough. You have to work hard. The person who does better is the person who works harder. You might have gotten rejected today. So what? You may get rejected tomorrow. What are you going to do about it? You know, so I was that way as a parent as well. You know, I gave him a lot of love and support, but I also wanted to tough him up, you know, I didn't want to soften every blow for him. So as a child, you know, up until he reached his teenager years, you know, like many parents, he loved his mother so much and all of a sudden he didn't love me so much anymore, you know, and you know, when they're young, they think you know everything and at a certain point they think you know nothing.
And he, you know, he was never a bad kid. He wasn't rebellious in the sense that he did negative things, but he was always a willful person like I was. I think he got that from me. And I very consciously did not want to pound that out of him the way my father wanted to get it out of me. I wanted him to keep his will. You know, I was a teacher of young children way before I even had Robert. And I used to say to parents, the most dangerous behavior problem is no behavior problem. It's those little kids, especially the little girls who sit there and they never do anything wrong and they never fight back. They never say no. And then as adult women, they don't say no and they don't know how to stand up for themselves. So I really believe in the importance of that. So I sure got that in spades when he was a teenager. But I got to say now and I admit that to him now looking back a lot of times he was right. You know I think parents say no too much. May I tell a little story about that?
