Building a network of mentors, with Cadre’s Ryan Williams
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I went down to Atlanta with my roommate, visited his neighborhood, and his neighborhood was completely ravaged by foreclosures. Ryan Williams was still a college student when he saw firsthand the impact of the 2008 housing crash. There was the idea and the opportunity right there. I said, well, what if we could start buying some of these homes? They're neighborhoods we know. They're people and communities that may have been prone to subprime predatory lending.

Ryan saw a way to help the community and gain experience as an investor.

This week, he shares how he founded a company to take on entrenched competition in the real estate market, what he learned when that business was swept into the spotlight, and why he eventually decided to exit. You've got to have incredible talent at every position. It's like this huge push. There are fires burning when you're going out. Can you believe it? Such an idiot. And then you go back to, this is totally going to be amazing.

This is Masters of Scale. I'm Jeff Berman, your host.

Ryan founded Cadre in 2014. It's a tech-powered commercial real estate investment platform. And that may not sound like the most exciting thing you've ever heard about, but he sold the business recently. It's a sweat-driven story of an entrepreneur who started way back when he was a teenager.

Ryan, welcome to Masters of Scale. Thank you for having me. I'm excited to be here. Great to have you here. Like a lot of our guests, you started your entrepreneurial journey early. Can you tell us about your first forays into being an entrepreneur? Yeah, absolutely. My, um,

earliest days were in Baton Rouge, Louisiana, which is where I was born. And Baton Rouge is a city that's divided and historically has been divided physically and economically. But despite those divisions, what I saw at least was opportunity and a lot of people who were making the best out of challenging situations. And so when I think about entrepreneurship, that's sort of the lens that I always saw the world through, which is there's always going to be barriers. There's always going to be

challenges ahead of you, you know, but I saw so many examples of people prospering despite that adversity and figuring out creative ways to address some of the challenging circumstances they were in.

And so for me, entrepreneurship is really a state of mind. I had so many endeavors that didn't work out. I actually tried to start a local sort of bait and tackle shop up selling worms to people and that didn't work out largely because no one knew who this little kid was trying to sell this kind of product. And so the first real venture was my personalized sports apparel business where I was selling these custom headbands and wristbands. And again, born out of a pain point, couldn't afford the Nike or the Adidas or the Jordan headbands and wristbands.

How old are you when you do this? I was 13. Okay. Yeah. And so I went to local wholesale garment district. I bought, you know, these terrycloth headbands and wristbands. Initially, they were just for me because I wanted to have some kind of design or logos that looked somewhat like the Nikes of the day. But then teammates said, where'd you get these? And I, you know, obviously didn't let them know what my connection was, but I told them, you know, I could...

provide same kind of access to them and you know maybe charge a little bit of a markup and that's what i did and actually made decent money i mean hundreds of dollars but it uh showed me that there's a market here and i found a local embroiderer decided to start customizing these headbands and wristbands i'd ask you know what's your favorite you know slogan or your team name or your number

reach out to my embroiderer within 24 hours, have custom embroidered headband or wristband. And I actually started really growing the business throughout the state and throughout the region and caught the eyes of a nonprofit called the National Foundation for Teaching Entrepreneurship or NFTY, which is based out here in New York.

They said, you know, we heard about this business you have. Would you be interested in applying to our national business plan competition? You can win a grant and come to New York City. And did you like go on Google to figure out how to do a business plan? It must probably be like Alta Vista, whatever the search engine was at the time. But I brought the only suit I had.

which was the Sudabweird Church, and ended up going through the pitch, the presentation, won first place, won a $10,000 grant. And most important for me was I got access to mentors who saw more in me than I saw in myself. And it was their urging that led me to apply to Harvard, which was, you know, a huge inflection point, first one in my family to go. From there, you know, things really took off for me.

So let's talk about CADRE. If you could explain in simple terms, what is CADRE?

Cadre is a technology-driven real estate investment platform. I started the business to democratize access to real estate and ultimately alternative investments. And it's a platform where people can log in, they can invest in either single real estate properties or in portfolios that our team curates for them. And the idea behind Cadre came to me after spending time sitting at some of the most well-known institutions, Blackstone and Goldman Sachs.

seeing how much money and wealth was being created, but for a relatively small part of our global economy and questioning, you know, why is this the way of the world? Why can only the 1% of the 1% benefit? And so I decided to build a business that would be akin to a blackstone, but with a tech stack behind it for the masses.

It's a platform so that if you're an investor who can't afford a $20 million building or $100 million building, whatever, you can actually do fractional ownership similar to buying into the stock of a company. Exactly. One of the companies that they arrived a couple of years before us, but that I spent a lot of time with early on was Robinhood.

And so in many ways, Robinhood was able to do in the equities market. We aspired to do in the alternative space as well. Yeah. And so the origin of the idea, I appreciate the inspiration and being able to see at Blackstone and Goldman how much wealth is created for the one one hundredth of one percent. But why real estate? Why this direction? What was the spark of inspiration for you on this? To know why real estate got to go back to that those college years.

financial services, venture capital, private equity. I started doing a ton of research on those spaces. So what I recognized quickly was that there really wasn't a way for undergraduates, especially those who didn't come from the finance world, to get smart in these spaces. And real estate really resonated with me because I never owned real estate. My family didn't growing up.

but it was always around me. And so I had a curiosity about it. And so the more time I spent learning about it, the more I realized that it was the most important asset class to own to build long-term wealth, yet very few people were able to actually own it, especially people such as myself. And so it was a curiosity. I built a curriculum. I recruited some Harvard Business School professors to teach the curriculum, which, again, hindsight was crazy. Just to be clear, you are a freshman at Harvard. Yes.

This is a very much a fish out of water in terms of like, this is all very new for me. I'm not seeing the things that I want to learn. So I'm going to do the research myself, develop a curriculum, and then I'm going to just show up and hang out outside the door of the Harvard Business School professors until I find one who says, I like it. Yes. Yes, that's right.

That's right. Fearlessness. And, you know, it's interesting because, again, it goes back to what my grandfather said. What's the worst thing that can happen when people say no? And a lot of people did say no. But, you know, I've been in the entrepreneurial world. I was used to being rejected. Right. People said no to your worms at the bait and tackle shop. And they said no to almost every other concept that I thought of. And it takes, you know, as an entrepreneur, a really, really strong will. And so I knew all I needed was two to three professors who would say yes to

We believe in this concept and we think others should be able to learn some of these concepts so that they can go off to real estate careers and have the same opportunities that people who come from that network. So this was the kernel of the idea for Cadre? This was the kernel of my passion in real estate. So this was where I found and I learned...

how lucrative real estate could be is a professor named Arthur Siegel, who's a renowned HBS professor in real estate who taught the real estate curriculum I developed. And I'd spend time with him after class and he would always say, "Ryan, the best way to get into real estate is to get into real estate." And it's nice to have the theory, it's nice to understand cap rates and all the concepts,

you're not really immersed in it until you actually are investing or owning or a part of a real estate firm. And so that just stuck with me, you know, and I was like, I'd love to figure out how to get involved. The next year was a great financial crisis. And so, you know, I believe that

Timing is everything. And that period of time presented a lot of challenges for so many people, but also opportunity. And so in the midst of the great financial crisis, I went down to Atlanta with my roommate.

visited his neighborhood and his neighborhood was completely ravaged by foreclosures. - Full of subprime. - Subprime, I mean, his own home was up for being foreclosed on had gone through the short sale process. And so there was the idea and the opportunity right there. I said, well, what if we could start

buying some of these homes, they're neighborhoods we know, they're people and communities that have had a hard go at life in a lot of ways and may have been prone to subprime predatory lending. Let's give them a second shot at the American dream and raised money from some classmates, bought a few homes, rented them back out to people in the community and ended up selling back one of the homes to one of the previous owners

Made three times our money. And from there, my passion for real estate really blossomed. We started buying more homes, thousands of units we acquired. Now, this was sort of my night job. My day job was working in finance to pay off my student loans. And I got to a point where I had enough belief and conviction in the understanding of real estate to say, you know what, now it's time to take the next step.

step in my journey. What was that inflection point? Was there a moment where you said, okay, I've got enough confidence. I'm far enough along where I can leave finance and go do this. After, after my first year at Blackstone, um, in their real estate private equity group, I saw what they were doing. Thousands of homes, you know, on a weekly basis, I was buying one or two, maybe on a quarterly basis. And so I was like, I didn't necessarily have the same level of

belief that the investing that we were doing was going to accrue to the benefit of the community. The same way that if I were to have invested in a community, I'd know I care about both doing well and doing good.

For a lot of people in this situation who made it to Harvard, have made it to Blackstone. I mean, we're doing pretty well right here. And you've got this drive and you've got this idea. They might say, I'm going to be an entrepreneur. I'm going to do this at Blackstone. I've got the security of Blackstone behind me. What gave you the confidence and the impetus to say, I'm out, like I'm going to go do this on my own and not do this here?

I decided that, you know, I'd done well enough financially. I wasn't going to optimize just for the next dollar. And instead, I want to have an impact. And also, I thought a lot about, you know, if I didn't go out and build this kind of business, you know, I'd regret it down the line, number one. But number two, someone who may not have the same goals and mission, you know, in terms of promoting self-determination amongst the underserved, which is kind of like my founding principle. And I always said, like, you know, in order to get unconventional outcomes, you have to do unconventional things.

So you're at Blackstone, you see this opportunity and what are the steps you have to take to actually jump, you

The next step for me was to figure out how do I build an MVP? How do I build a product where it's easy for people to log in and invest in real estate projects? So my second year at Blackstone, by night, I was building out my business plan and building out the first version of the product and an MVP. Did you have a technical co-founder? Are you coding? I don't want to hype up how dynamic it was, but they were very immersive, dynamic wireframes. But yeah, the first version of the product and the platform I built, the first...

actual asset was an asset that I was able to secure vis-a-vis a relationship with Jared Kushner, who was one of my earliest partners as well. And then the investor base, those who were buying fractional stakes from my network and then from friends and family who I'd gotten to know as well over the years. So we kind of built proof of concept.

And at the time, too, this idea of technology, which is hard to believe because this was 2014, but the idea of technology changing real estate was still crazy to a lot of people. PropTech, FinTech, these were still slogans and phrases that people sort of laughed at. And so in a lot of ways, we were very early, which is probably one of the reasons why the folks at Blackstone were supportive that I was not going to a competitor and instead

you know, was taking this moonshot. But I think in a lot of ways, it was eating at some of the core principles of the business at the time. More with Ryan Williams on his decision to exit Cadre in just a minute. The Lobatical is for any employees who have been with us for five years to take a vacation. They get a week of extra PTO. They get to pick anywhere in the world that they want to travel. And we allow that to happen for them.

That's Brooke Wright, Capital One business customer and chief people officer at Local, a change marketing company that works with huge corporations in order to facilitate meaningful communication between C-suites and their frontline. We wanted to celebrate them for the time they had invested with us. We liked the idea of a sabbatical, and so we made it us. It's the Lobatical. Local practices what they preach, caring for their employees with the same rigor they instruct their clients to enact.

My day-to-day is focused on making sure that we're living out the same principles that we're guiding our clients on inside of their large corporations. How you take care of your employees is a direct correlation to your customers' experience with your brand or product. The Lobatical is just one of the ways that local ensures their employees feel appreciated and cared for. And feeling appreciated is a principle that is shared by their partnership with Capital One Business.

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I want to tell you about one of my favorite podcasts that isn't one that we make. It's from New York Magazine, and it's called Pivot. Pivot is hosted by tech journalist and dare I say friend, Kara Swisher, and NYU business professor, Scott Galloway. Every Tuesday and Friday, Kara and Scott break down the major stories of the week in tech and business and politics and more. I always get razor sharp insights, both from the

bold, occasionally crazy predictions, and yes, lots of bickering and bantering with Scott occasionally throwing in the inappropriate remark. I encourage you to listen and follow Pivot wherever you get your podcasts. Welcome back to Masters of Scale. You can find this conversation and more on our YouTube channel. I wanted to hear more about how Ryan built Cadre's client base. He had a much more complex offering to market than, say, a consumer product.

The B2B, which is really what I think we are more of in the B2B2C business as well, it's a very different playbook, especially when the underlying industry is one that is used to everything being analog, offline, relationship-based. And so my approach to scaling the business was a little counterintuitive, which was start at the top.

of the customer pyramid, if you will, like with the most sophisticated, discerning, analog, offline potential partners, but also the ones that have the most gravitas and the most trust. What's an example? Goldman Sachs. Good example. Right, exactly. And so you think of Goldman, you think of this behemoth, and you think of this institution that is

relatively slow moving in the scheme of technology companies. You think of, you know, a lot of domain understanding and expertise and investing. And what I wanted to do is build a moat around some of these highly sophisticated partners from a distribution standpoint, get them to buy into the concept, get them to distribute our product to their clients. And from there, I thought you could then go down the kind of

customer pyramid, if you will, to a wider range of investors that maybe didn't have all the quote unquote sophistication, all the infrastructure that someone like Goldman had, but would look at Goldman as a social proof point. So that meant the sales cycles for getting some of these partners to bring their clients onto our platform to invest were much, much longer. So as an investor at VC, you've got to be willing to understand that this is more of a marathon than

a fast marathon, it's not a sprint. And the rewards from a lot of that investment early on in building an infrastructure that is trusted, credible, that has all the safeguards you would want in place, that's a well-curated platform, will pay dividends down the line. And so after a lot of conversations with folks like Goldman and JP Morgan and Ford Foundation, some of these bigger institutional clients,

We ended up winning a few contracts and we were able to strike some partnerships in less than two years since I started the business with some of the biggest names in the financial services world. And once we've got those investors to say, you know what, this is a really unique way to give our clients access to real estate at smaller fractional bite sizes with liquidity, then being able to go to independent advisors.

and direct to individuals became infinitely easier. But the muscle that at least we had to be able to build was we needed to have a really clear playbook for these longer sales cycle meetings and engagements where we knew what meeting one was going to need to look like to hook these investors on the concept of what we were looking to do, the value proposition. We knew that we were going to need to meet them in person because it was very much relationship business. We had one shot at

technology demos and giving them a view into what this would entail because there was already skepticism. And then there's an ongoing client relations management side of this as well, where we had to bring on domain experts who could cultivate those relationships. And so we spent the first few years building a highly concentrated base of significant whales, if you will. I like to use a fish and whales analogy. And we were able to get those investors

to say, yes, we believe in this business, we believe in the product. And it really differentiated the brand. Were the Goldman's committing minimum dollars to be invested as part of these deals? And then they were passing on the opportunity to their clients and they just knew that they could fill up to that number. So what we did with Goldman, which as far as I know, hasn't been replicated, we secured a $250 million commitment from Goldman, you know, the institution. And then they had about 1,000 salespeople

sub-advisors and clients beneath that commitment. And those were the individuals that ultimately owned fractional stakes in the properties or the portfolios that we built for them. And so I would say it was really building that critical mass of high impact, large enterprise-like clients that gave us the ability to then open up access to a wider range of folks from a position of trust.

One of the most unexpected challenges Cadre faced was around media attention it received during the first Trump term, because one of its earliest investors was Jared Kushner, who suddenly had a role in the White House, which might have created conflicts of interest.

We got a lot of attention. It wasn't necessarily for what I thought the reason would be. And I guess taking a step back, Josh and I were in school together. It was a couple of years ahead of me. And Jared had been really supportive in one of my real estate businesses and also on a personal level. And so I got to know them in a very different context than the world has seemingly gotten to know them. They were still relatively early in their careers. And so when I was thinking about partners and thinking about the kind of people I wanted to work with,

Those two, off the bat, checked every box. And so my experience with them has been incredible. I never anticipated the geopolitical focus on the business. And I always made it clear to Jared and to Josh that I had certain principles and values. And those values are, for me, values I would never forget.

and I would never concede on in any way, shape or form, respect, integrity, transparency, empathy. These are all things that I was raised with and in all my experiences and in times with them, there was a genuine respect for those values. We didn't always agree on everything. And I don't even think Jared and Josh agree on everything. But what we did agree on was we wanted to do what was best for Cadre and to move the business forward because it was a company we all had a deep passion for.

And so, you know, that led to, you know, everyone in a lot of different ways making selfless decisions. You know, Jared extracting himself from the business when he went down to D.C. when he had, you know, brought so many of his relationships under the tent. Josh encouraging me, you know, to find my voice and speak truth to power when there were things that I saw that I didn't agree with.

especially in light of George Floyd's murder in 2020. And I would say overall, our company and our team grew from that experience and from having so many politically connected partners, because it wasn't just Jared and Josh. We also had the Soros family, who was one of our biggest backstop partners, and Mark Cuban, who I communicated with on a weekly basis. So we had the whole full political spectrum, but Jared and Josh were there from the early days. And for me, my relationship with

them preceded, you know, all the media focus. How did you deal with some of the negative attention that this has brought to you? The first thing I would say is I was very naive about the media world. You know, I probably in hindsight could have gotten ahead of some things earlier, but you know, you can spend all your time managing media and then, you know, the business suffers. And so I had some incredible mentors who I went to whenever there was a story on the horizon. Who were some of those mentors? People, uh,

like Vinod Khosla, who I would talk to. And Vinod was great in that he gave me this advice that still resonates with me today, which is the most important thing

attribute in his mind of an entrepreneur is who do you listen to for what advice? And that's a muscle as well, right? It takes time because early on, you know, it's sort of a trial and error. You listen to one person who gave you certain advice on one concept or theme and you realize it was not the right person to listen to. And so what I did was I built, you know, I guess a little cadre, if you will, of advisors around me who I knew would be great, you know, for certain challenges.

And Vinod was super helpful as it related to managing the team and keeping everyone focused in-house while there were media stories surrounding the business. I spoke and spent a lot of time with Michael Ovitz as well. And seen his share of controversies he's had to deal with. Right. And Michael was great as well with making sure I kept my head on straight. And I focused on the main thing, which was media.

making sure our business continued to scale and achieve product market fit. And then I actually talked with Josh Kushner a lot as well too. And Josh had a very unique perspective, obviously being in his seat, but was incredibly supportive throughout. And so again, I consider myself really fortunate that

You know, despite all of the craziness that came with being a CEO and a founder, plus at that time, I had this network of people around who cared about me. One of the things I learned from that experience is you can never over-communicate to your key stakeholders. And so I had to get in front of it. I had to stand in front of the company and say, hey, you know, tomorrow this is going to be something that's out. Here's the truth of the matter. Let's stay focused.

I'm carving out six hours of my day for one-on-ones. If anybody wants to talk with me about, you know, anything that's bothering them or they're excited about, I'm here for you. And that was like a leadership evolution that I had to develop. And it sounds deeply consistent with your personal values, transparency, openness, right? And, you know, you were creating opportunities for yourself to talk to the people you wanted to get to. And you're giving that opportunity to your team to say, I'm here. Right.

The list of advisor names is just a who's who. Is there a secret that you want to pass on to people about how to build that level of a set of advisors?

What I would say to people that want to build that kind of cohort of domain experts, it's got to be a symbiotic relationship. You know, there has to be something you're bringing to the table. You can't come with your hands open every single time asking for something. So for me, you know, as I thought about some of the investors, other than investing in the business, which is great, it was also keeping people focused.

close to certain themes and trends that I saw in real estate or alternatives, you know, sharing with them insights that I saw that might be helpful for them, sharing perspectives about other founders, you know, that were emerging that I had gotten to know that I thought would be interesting for them to get to speak with. And then just making sure, you know, you deliver on what you say you're going to do. So for me, it was following up the communications, whether those were

weekly email updates on how the business was doing, asks that I had of people, but then also insights I wanted to share. It was just about being consistent and ensuring you held yourself accountable as well in those dynamics. And then to the extent that you deliver on one of those engagements, it becomes like a snowball. And this person says, oh, I really would love to connect you to this person and this person. And before you know it, you've been able to build a really strong group around you. But I think so often,

people look at those dynamics as transactions in a lot of ways because they're like, okay, what can I actually bring? And there's a lot, you know, that, you know, people can share that you might not necessarily think is valuable to hear. But, you know, some of these folks

folks who are in kind of high places actually enjoy learning about. Yeah. So you mentioned landing the Cadre plane in a way that was successful for your investors and your stakeholders. Why did you decide to sell the company? So it was one of the toughest decisions I've ever had to make. It was challenging because I think that in so many ways, your identity can become inextricably linked with what you do in your profession. And for me,

I saw that certainly happening. So when I started the business, the vision was democratizing alternative investments. Real estate was the beachhead product. The pandemic was sort of a shot in the arm in that it showed me the importance of

and diversification. And so the question for me was, how do I most efficiently diversify our business such that we have multiple business lines that can endure any market condition? So there are two paths that we could take. One was we could go out and we could raise additional capital to build other mini cadres, you know, a credit and a,

private equity and farmland and infrastructure, or we could partner. And the building path, in my mind, was a much longer path. It was a more expensive path, just given where the markets were. And it was a less certain path in a lot of different ways. The partner path was really interesting because we had so many inbounds from

large institutions that were interested in what we were building and doing in acquiring the business. And we had interest from other fintech and consumer tech platforms as well. What I wanted to optimize for was a partner that could allow us to diversify our product offerings as well as our distribution.

and a partner that had mission alignment. Because yes, we could go work with, you know, you name your big institution, but you know, at the end of the day, it's not necessarily a guarantee that why I started the business would be what they were. You may be selling your soul along with your company. Exactly, exactly. You probably are. And so fortunately for me, I'd engaged with company Yieldstreet

many, many moons before I got to know the founders really, really well. And we both had alignment on the mission. We both cared about broadening access to alternatives. They took a different approach. They focused much more on the retail investor base from the outset. They focused much more on sort of credit and debt oriented products, but it was a perfect complement. And so after spending some time with

the founders, some mutual shareholders and investors. We agreed to join combined forces and technically sell the business in what at the time was the largest transaction of that year in FinTech land.

I'm proud of the team who really led a lot of the blocking and tackling of getting what was a complicated transaction done in an environment where there really wasn't much M&A happening. I'm really grateful for all the investors that believed in me and had conviction despite some saying, stay the path, stay standalone. But it had been a decade since I started Cadre. This was a really great way for me to leave an impact on the market and ultimately

fulfill the promise of why I founded the business. So what's next? So landed that plane. I'm just starting to think about take off for my next journey. It will be a company that is at the cross section of financial services and technology.

I'm spending a lot of time now speaking with potential clients, customers, doing all the fun due diligence, as well as prospective investors in the business. I'm excited about applying the learnings. A lot of people are like, Ryan, aren't you going to take some downtime? And it's actually somewhat therapeutic to be able to apply the learnings from decisions I made that worked out and that didn't into what's to come next. And I want to focus on working people that I...

I share values with that I care about that have the same incentives, you know, as I do in terms of, you know, financial as well as mission, you know, and build on what I've been able to do. But I'm an entrepreneur through and through. And to your point earlier, that's where I feel most fulfilled, that zero to one phase. And, you know, I love to,

be in the midst of ambiguity and absorb it. And to me, that's the essence of entrepreneurship. No, we can't wait to have you back on to talk about the new thing. Can't wait as well. Great. Thanks so much for being here. Thanks for having me. Appreciate you. Thank you. Ryan's resilience and drive have already helped him scale one business from scratch. His story is a testament to the power of building and nurturing a network. When you sit in person with Ryan, you can feel this energy.

It's different with some entrepreneurs than others. He exudes it. You want to root for him. You believe in him. You're excited about whatever he's talking about. I can't wait to see what he does next and hopefully have him back on Masters of Scale to talk about it. I'm Jeff Berman. Thank you for listening.

We've grown exponentially since we opened 10 years ago. We initially started with, I think there were 10 of us, maybe, total, which is just completely ridiculous. That's Jillian Field, Capital One business customer and co-founder of Union Market, a popular neighborhood market and cafe in Richmond, Virginia. With her growing success, now with 45 team members, Jillian has always kept sight of what really matters.

We felt since we opened that having some sort of employee appreciation event was really important to us. Every year, Jillian holds a company-wide celebration to show her staff how vital they are to the success of Union Market. Recently, she used points from her Capital One business card to host her employees at Busch Gardens Theme Park for a day of fun with family and friends.

We buy all of their tickets as well as their plus ones. It's a lot of fun and definitely a great team bonding experience. Capital One really has been great over the years. It's so easy. We could apply these points to supplies, masking tape and Sharpies and ticket receipt paper, but we like to retain them for our employees. That's been really important. To learn more, go to CapitalOne.com slash business cards.

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