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Leading in the B-Suite™

Ryan Williams

“There’s Been An Awakening, And It Can’t Be Ignored Anymore”​

July 13, 2021

Ryan Williams, the co-founder and CEO of Cadre, a real-estate investment platform, shared powerful lessons with me and Rhonda Morris, the chief human resources officer of Chevron, for our interview series with prominent Black leaders. Subscribe here for future Leading in the B-Suite interviews.

Morris: Who were important influences early on that shaped who you are today?

Williams: I didn’t really have a lot of folks who looked like me or who had my business background. Where I’m from, there just weren’t many examples of people who charted a path similar to what I am doing today. When I think about who influenced me to strive for more, to prosper in the face of adversity, to take chances and see more of myself than I even saw, I think first and foremost of my grandfather.

He grew up in Baton Rouge, in the Jim Crow South. His grandparents were born into slavery, and despite all the challenges he faced — not having access to resources or opportunity — he was a pioneer and somebody I looked up to. He was a preacher of one of the largest AME (African Methodist Episcopal) churches in New Orleans and was the first president of the Louisiana Teachers Association and one of two leaders tasked with helping ensure integration occurred throughout the state of Louisiana in the late 60’s and early 70’s.

He died when I was relatively young, but I spoke at his funeral in front of hundreds of people. I would spend time after school with him, and he shared lessons with me about how I was going to have to work seven times harder than anybody else. He encouraged me to take chances and not let the constraints on me stop me from excelling.

And my grandfather always made it clear that education was the way out. I was always told that I should try to get as many degrees as possible, because you’re going to need them when people inevitably start doubting your credibility and legitimacy. It’s one of the reasons why, despite a lot of people telling me that it was going to be a long shot, I decided to apply to Harvard.

I was surprised when I got in, but a lot of it was based on some of the things I did outside of class in high school, like starting businesses. There were a lot of people I grew up with who were just as intelligent and talented, but who maybe didn’t have the people who believed in them that I did, and who maybe didn’t have a couple of the breaks that were critical for me.

Bryant: What was it like going from Baton Rouge to Cambridge?

Williams: I believe it was W.E.B. DuBois who said he was “in Harvard, but not of it.” He didn’t have that pedigree, that background. I relate pretty strongly to that. For me, it was a culture shock going to Harvard in many ways. And frankly, during my first year there, I didn’t entirely know if I was going to make it. It was really, really tough.

But in my second semester, when I briefly considered leaving, I found a group of guys — also Black students at Harvard — who had some shared experiences and passions. That was critical for my own wellbeing and for my confidence. Harvard was the first time I was part of an academic institution where I saw people who looked like me who were excelling academically and thriving.

Up to that point, the reality is that, for the most part, I thought I was an exception and I thought there really weren’t that many folks who looked like me who were thriving at the highest levels. And my community, in some ways, reinforced that. Growing up, it wasn’t thought of as cool to do well academically or to start businesses. So, I found that community within Harvard, and it became a source of strength.

I was able to be myself. I was able to be open and vulnerable. We had shared challenges and successes and it created a deeper connection and a deeper trust where I could tell one of my roommates, “Look, I’m struggling in this area. How did you get through this?”

When I was with my friends, it was a productive, safe space.

We wanted to help each other, and we made a commitment to each other that we would graduate and we’d thrive and stay close and connected after Harvard. We all saw that our individual and collective success were inextricably linked. And we’ve done that. Two members of that group ended up becoming my business partners.

Before I met those friends, my first roommates were the ones that were just assigned to a room. Neither had grown up with much diversity, let alone lived with a Black person before. It was intimidating for me. We didn’t have much in common.

And one roommate even made unfounded accusations about me stealing certain things from them. Sometimes there’s this duality in the professional world, as well, in which you have to try to navigate multiple worlds. I didn’t know how to do that early on, and it was stressful and emotionally taxing. But when I was with my friends, it was a productive, safe space.

Morris: Where did your entrepreneurial drive come from? 

Williams: I’ve always had this mindset of seeing challenges as opportunities, and a lot of it comes from my upbringing. I was always taught that you have to be grounded in reality. You can hope and you can strive for more, but you can’t deny the way things are before you start thinking about changing the paradigm in some way.

The first example of this for me was a sports-apparel business I started when I was 13. I played sports growing up and wore headbands and wristbands when those things were still cool. I didn’t have a lot of money to buy a Nike or Adidas or Jordan headband or wristband, but I found a wholesaler who was selling terry cloth headbands and wristbands for 50 cents or a dollar each. I initially just bought them for myself.

My teammates asked me where I bought them, and I said, “Well, I can get you some as well. It’ll cost you $1 or $2,” which was less than what the brand-name gear cost. Then I had the idea to personalize these headbands and wristbands.

I found a local embroiderer who was willing to stitch logos and slogans on them. We started a partnership, and I built a website to sell them. We were doing thousands of dollars in monthly sales as I was going into my junior year of high school. The business kept growing, and I exited the business during my freshman year at college.

It built that muscle so that I could go from asking “why?” or “what if?” to developing a hypothesis, a solution, and then build a business. But you have to be persistent and believe in what you’re doing. It also taught me that it was okay to be unconventional and to be different. Most people I knew, especially from my background, weren’t building businesses. That taught me that it’s possible to take the path less traveled.

Bryant: Can you share what are some of the headwinds you have faced in your career because of your race, and what are the tailwinds that have helped you navigate them?

Williams: When I was starting Cadre, I would go to meetings with VCs and investors and people would ask, “Where’s Ryan?” Other times there were questions about my background, my experience, and people doubting certain things about my journey, and even about my time at Harvard.

A lot of that skepticism just comes from ignorance, and people not used to seeing folks who look like me in positions that I’ve been in. A lot of people, especially investors, have historically ascribed more risk to people who don’t fit certain molds or certain profiles of “success.” But my background in many ways has provided some real tailwinds, as well, because I’m used to a lot of adversity.

You have to believe that it’s possible to change the status quo.

I’m used to being the only person who looks like me, and when you’re trying to tackle an industry like real estate and democratize access to real estate — an industry that’s been an old boys’ club for a while — you need a different perspective and resilience. You have to believe that it’s possible to change the status quo.

Morris: We’ve been having the same conversation about race for decades. What’s different now and where are you on the optimism-versus-pessimism scale?

Williams: I am optimistic. What happened over the last year with the murder of George Floyd wasn’t just some random spontaneous combustion. There are deep-seated inequities that have been right under the surface for centuries and it took one event to raise that collective awareness so everyone could see exactly what was happening.

There was a long period when people were “snoozing” on issues of race and equity. But ignorance is not going to change the fact that at some point you have to wake up and acknowledge our reality. I do think that the public-private support is encouraging. I also think people are increasingly open-minded, increasingly willing to try to understand the “other.”

I believe that there’s going to be more empathy, more compassion, and more action. The alternative isn’t sustainable. We can’t afford to close our eyes to these disparities and inequities for another 30, 40 or 50 years.

Morris: What advice would you give to young Black professionals who wonder when they should confront people when they face micro-aggressions, and when they should let them go?

Williams: Context is everything. You have to be aware of the environment and the circumstances when things like that happen. And situations are nuanced and it may not always be the most constructive thing to confront a perceived micro-aggression in the middle of a meeting. That’s just a reality. But there’s been an awakening, and it can’t be ignored anymore.

This dynamic would generally lead me to say that more confrontation is better, because silence isn’t acceptable anymore. The question is how you do it. I believe that we should be using those moments as learning and teaching opportunities. It doesn’t do much good to purposefully try to hurt somebody and win points. Instead, try to share and educate.

It doesn’t do much good to purposefully try to hurt somebody and win points.

I’ll give you an example. A few years ago, I met with an investor to raise some capital. He made a comment in the context of challenging me on a few points related to our business. The comment was at worst racist and at best ignorant. I was compared to an animal.

I could have, in that meeting with everybody there, said that this is out of control and wrong and accused this individual of being racist. I don’t think that would have been productive. It would have felt good, and I wanted to do that, but it would have put him on the defense to deflect or try to counter what I was saying.

Instead, I caught up with him after the meeting and explained why his words were damaging, hurtful, and wrong. We didn’t ultimately end up moving forward with this investor, but I think he grew from that conversation. The more we can work to a place of shared understanding and compassion and non-judgment, the more likely people will be to hear and heed feedback.

Bryant: Any final advice you can share that you would give to young Black professionals?

Williams: I have two younger brothers, so they hear a lot of advice from me, whether they like it or not. The biggest piece of advice that I would give folks — especially if they don’t come from a background of privilege, wealth, and opportunity — is that in order to get unconventional outcomes, growth or rewards, you have to take unconventional risks, and you have to be willing to fail.

One of the challenges I always faced early on was a fear of failure because I didn’t have a Plan B or something to fall back on. What I recognized, even when I did fail, was that I was able to recover. I was able to grow and learn, even though it was painful in the short term. I learned so many lessons from taking risks and pursuing business ideas in industries where there weren’t a lot of people who look like me.

Ultimately, life is so short, and you really have to think about how little time you have to go out and make your mark on the world and make an impact. If you don’t take risks and you have regrets later, that will be a tough pill to swallow. More than ever, there are more opportunities and ways for you to get connected to people to start a business.

Even if you don’t knock it out of the park or achieve the outcome you were hoping for, I guarantee you’ll learn a lot more by taking that that risk than by doing something more conventional. I look at my life and my career thus far, and sometimes I pinch myself because of where I am and what I’ve been able to achieve with the investment and belief in me from others.

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