Aspirational Investing


Conventional wisdom in the financial sector suggests a compromise exists between above-market returns and impact. We aspire for more. In this series, we speak to fiduciaries at the vanguard, who refuse to compromise between these two objectives, innovatively pursuing top-quartile performance inclusive of their unique missions.  

E001 | Rudy Cline Thomas

In this episode, Mike sat down with Rudy Cline-Thomas, founder and managing partner of MASTRY, an alternative asset manager focused on venture capital, sports, real estate, and media.

As a producer, Rudy has been recognized for his work on “The Scheme,” a Sports Emmy-nominated documentary on HBO. He also founded The Players Technology Summit in partnership with Bloomberg. This event offers a platform for tech, venture capital, and sports communities to discuss trends in tech investing with leading athletes.

Rudy serves on several advisory boards, including those for Salesforce, Gucci, Jumia Technologies, Zuora, Fifteen Percent Pledge, Global Communities, and Providence College's Board of Trustees. He also co-owns the Leeds United Football Club (LUFC) and the Hapoel Tel Aviv Football Club in Israel.

Mike Miller, CIO | Published March 4, 2024

MM: What are you trying to achieve at MASTRY—what’s your vision?

RCT: It’s about bridging alternative markets and underserved communities, as someone who doesn’t look like the typical industry standard yet understands the essence of the capital markets and the effect they can have on such communities.  

The idea started because it was interesting and meaningful to me. The essence of this meaning is based on understanding what speaks to underserved communities in terms of change and social impact—finding where this impact can be most effective. Part of this community impact is cultural, and a lot of mandates are created by individuals that have no insight into underserved communities. I'm motivated to change these benchmarks.

We aim to identify exactly where impact can be best uncovered, where it’s most effective, and redefining the approach across the entire industry. What does that look like? It starts with identifying the segments of the market that speak to the community the most. 

I think sports and entertainment have an outsized effect, and from capital markets and institutional capital, we haven't looked at it as such, as a contributor to impact, especially paired with technology. Individuals that look like me haven't owned these platforms, but doing so can act as a vehicle of change and have an uplifting influence on our society. I think we haven't even scratched the surface yet.


MM: We frequently talk about investors as unique individuals, almost artists, with a blank canvas to paint a picture. What's your picture and what are the common themes in your brushstrokes?

RCT: First and foremost, I'm definitely an investor. I'm extremely curious—curious to understand in which directions capital markets are going but also about new technologies and platforms that change the way that we think about and do things in all the different facets of our lives.

This investment platform really speaks to my curiosity and all the different segments of it. A friend of mine recently said, don't work too hard; I said, I retired 20 years ago.  This is not work, being able to speak to your curiosity and all the different ways one can seek it in the world. That's exactly what the MASTRY platform is, which is in a way somewhat selfish, but again, firmly based on the pursuit of impact.


MM: At Crewcial, we've always prided ourselves on thinking outside of the box, and maximizing that advantage and impact that you can have when you think about this broad world of options. Yet, sometimes, it can feel as if the investment world keeps getting smaller and more homogenous; at least, that’s how some people tend to invest. But based on what you're doing, expanding the world we can tap into, what advice would you give us and me about how Crewcial can be better?

RCT: The two things that I believe initially brought us together are our shared intensity and curiosity. However, underlying that is a certain fearlessness. When you see things differently, and you're trying to create new things, it takes a certain level of risk and fearlessness—an understanding that you're going to be an outlier that needs to be communicated to your audience and potential limited partners. Building something others don’t always understand at first is going to test your mettle, but it’s about running through that fire and not worrying about it.

I don't find any joy in common thought with mass appeal for the most part. My curiosity leads me to thinking of ways of doing things that I’ve never seen before. When I got into venture specifically, it was a breath of fresh air, because until that point, I hadn’t been surrounded by likeminded individuals that thought of the world the same way.

That’s when I realized that this is where I had to be. And I've taken this concept of venture and applied that to how I think broadly about life.


MM:  Transforming lives by driving systemic change through investment outcomes is clearly a huge motivating factor in your life. Can you explain how you approach this strategically, from the top down or the bottom up? How do you pursue your impact?

RCT: I want to make sure that we understand that word means something different to all of us; we're all products of all our life experiences. My purview is different from yours and everyone else's. For me, it's a top-down approach and strategy. I'm always thinking about scale first— for example, what are the biggest platforms or influential mediums in our community? From a capital markets perspective, the arts haven't been identified as having the ability to affect specific impact. We've looked at infrastructure first because it's much easier to measure. Now we're seeing sports becoming very much fancied by the institutional markets; the returns have been outsized, you know, for the first movers there 30 or 40 years ago. But again, they haven’t been seen or used as social platforms. I can comfortably say, it's because no one from underserved communities has owned these platforms, and it doesn't look like it's going to happen anytime soon at scale. But that’s exactly where I want to go; identify, first and foremost these cultural platforms, and make sure that we have limited partners that understand they can create a return profile based on these platforms that affects the entire industry while bringing more people to the table. That's exactly what I want to do.

I think the first segment of this is identifying the cultural platforms. Once we've identified them, and created a system and thesis to make them more congruent to institutional capital, then it's about taking this step forward and investing in these segments. Even if I fail, it gives everybody empirical data to build on. What’s most important to me is that somebody has to take that step and build the systems.


MM: What advice would you give directly to people who have had a harder time accessing capital? By extension, what kind of advice would you give people about how you've been able to succeed?

RCT: I really think the opportunity is out there for all of us. At the time that I was interested in venture specifically, I was shuffling between Philadelphia, DC, and New York, I had no access to the venture markets whatsoever. It was something that I read about and was keenly interested in. This was 2009. I used to read a weekly write up at that time, TechCrunch. Mike Arrington had started it maybe about four or five years earlier. And it was the only publication I could read consistently that gave me insight on tech. I was fascinated with the stuff I was reading. They had a conference and it was quite expensive at the time. But this was the only entry that I knew of to access this market, so I paid for it. I went out to San Francisco, my first time, and I knew nobody, but I had done my homework. If I saw or ran into certain folks there, I would jump at the chance at introducing myself. That's how my journey started. It started with that curiosity, that grit, and no excuses. We live in a world where information is abundant, and access to information is abundant as well. Grit and no excuses can get you far. That’s how I got here.


MM: You used a word before, which I think we should come back to, fearlessness. I think a lot of people in this world never realized their potential because they are afraid of not succeeding. Yet, anything worth doing has a high probability of failure.

RCT: Yeah. You just have to accept that. It never gets any different. I think that's the characteristic of success, the lack of fear of failing, which is directly correlated to your potential.


MM: You have this vision, which I think is amazing, but the challenge is convincing other people to buy into your grand vision. Then you have to not only execute on it, but you have to face whatever storms come along the way Once you establish relationships with people based on such a vision, how do you keep them engaged and confident, especially during inevitable shortfalls along the way?

RCT: I think I'm still learning how to do that. I can't speak to myself as a leader; I'd be remiss to even think that I'm a good one. I think it’s about making sure that I try to take as much responsibility as I can, including my insecurities. I think what's really important is that I don't panic. At the end of the day, we're extremely blessed to be here where we are and doing what we're doing; that's also extremely important here. I have to control those expectations at all times.


MM: You're talking about transparency and honesty, which I think are incredibly important in leadership. You're accountable and honest. What I find frustrating is when some people set a goal, but upon failing to reach it, they'll change the ground. And that's not honest or transparent. If you're going to reach for high levels, you can't change the message or the goal, because then you won't have any credibility. Frankly, I think that you're not doing that, which is really important. The other important thing is laying out a vision that people can understand.  

I’ve got one more question. To use the American term, we're both very into soccer. I'm just the guy who sits in the stands. And you’re guy who owns a team in the English Premier League with Leeds United. Tell us what's happened, and what it’s been like to own your own club.


RCT: I'll be honest with you, it hasn't really set in yet. I do a really, really bad job of seizing different moments; I think it's probably one of my greatest weaknesses. I never really set out to specifically own a team, or even thought it was a possibility. We're in a precarious situation right now; the next three to four months are going to be extremely stressful. It’s more important to me that I have a family that can attend games. And it's brought us close together on a daily basis; that’s what I want this club to become, in terms of what it means for the community. The reason why I did this, broadly, remains to be seen, but having this platform and the right partners that understand what it means to me and to them is a blessing you can only dream of, and I don't take it lightly at all. You can get caught up in the wins and losses, and of course I'm surrounded by that constantly week to week. But you take two steps back and put it into perspective. What I want to do with this in the future is hopefully going to become a dream come true. I’m really, really excited about that.

At the end of the day, whether you're a corporate CEO, a startup founder, or you own a team, you're working in your community; you have the expectations of the people you're serving that you're subject to, and it's important to be very open and transparent with your expectations as well, so you can openly communicate and get feedback. I think it's important for us to change the approach to transparency in terms of what we're doing and how we're doing it, and making our communities a part of that.

What were some of the main successes of Crewcial Partners last year?

Summary: Most importantly, we maintained our long-term posture through an unfriendly market. Markets have a way of overreacting to events; however, our clients stayed on track and kept their public equity exposure at high levels. Our process ensured we never faced liquidity challenges or any issue that demanded we act in a short-term matter.

Lesson: A long-term bias works but requires discipline, diversification, and an understanding of expectations. Fundamentals and valuation—the price you pay for something— ultimately matters. Crises and difficult times have winners and losers. The winners are ultimately those with the strongest balance sheets, best business strategies, and the most capable manager teams; they win over the longer term because they're better than their competition.

What are your thoughts on sizing in the current environment?

Summary: It can seem contrary to human nature at times; the stuff that does well, you want to see become a bigger and bigger part of the portfolio.  However, you should be adding money to managers that have struggled but are poised to rebound, keeping in mind your longer-term return profile. Sizing is important and depends on a deep understanding of diversification and manager volatility profiles.

Lesson: Take advantage of the natural cyclicality within markets, selling at the peaks and buying the bottom is the way to long-term sustainable success. Be proactive when managers have a great year. When Crewcial has a manager that's up 100%, we ensure that we trim back 25-50% so the capital is ready to redeploy into out-of-favor managers with even stronger future prospects.

What are some of the areas that could be improved from 2023?

Summary: We are still trying to wrap our heads around the way markets are actually functioning; the gap between price and fundamental value seems as if it's become unbounded. This creates a problem of balance. If you're constructing a diversified portfolio, one of your underlying assumptions is that it will moderate volatility and some of the short-terms concerns; this should allow you to play offense when things are bad and a little defense when things are really good. But that falls apart if markets are creating high correlations that shouldn't exist between strategies. We’re still learning to better understand which conditions can and will create more of these correlation issues, so that we don't end up constructing portfolios that require truly extraordinary levels of patience to see through.

Lesson: Cultivate a better understanding of correlation among managers.  Thinking about managers based on the way they behave in different market climates is important. Prepare for various environments and build portfolios that are not going to have several seemingly distinct strategies reacting to the same market environment. Diversification is ultimately always your friend.

What are some of the insights you’ve gained from your latest year of travel?

Summary: Being back on the road has been one of the great events of 2023. It’s rewarding to physically sit down with people, whether in Europe, Asia, South America, Africa, or the United States, and really hear what they’re seeing on the ground, what they’re doing in their portfolios, and the real-world implications, because markets aren't necessarily the real world.  Being reminded how different people see the world differently is immensely important as an investor.

Lesson: Preferable options exist outside indexation; opening up to a global perspective broadens one’s ability to consider truly impactful diversification. The goal is to find differentiated thinking wherever it is.  We're not looking for investment managers, we’re looking for thoughtful, engaged people who invest.

What does history tell us for “Magnificent Seven” index funds going forward?

Summary: The index has reached a very high level of valuation concentrated in a group of unbelievably dominant companies.  However, while no one is arguing that Apple is a bad business, there is a price for everything and this price seems too high right now. From the 60s through the 00s, people felt the same about many companies that didn't prove to be very good investments. One way to illustrate this is to look at the top five in late 90s, which included Cisco, Intel, General Electric, Microsoft, and IBM. If we exclude Microsoft from the equation, these are all still pretty powerful businesses but they have not been good stocks to own. It’s the inevitable nature of impermanence. We can almost guarantee ten or 20 years from now, the current names will be around, but they probably won't be the most popular or dominant names in the market.

Lesson: Design portfolios to capture the broader economy; while well-constructed portfolios will always have allocations to bigger names, entire swaths of the economy are growing at a much faster rate than these brand-name businesses and are currently being overlooked by investors. Capture long-term opportunities today cheaply.

What is Crewcial excited about for 2024?

Summary: First, ESG, which has unfortunately become a very controversial subject. However, at the end of the day, it's a powerful risk framework; from our perspective, we need to be able to arm both our clients and our research team and consultants with better information on this subject and approach, as it’s a complicated topic.  We can't make it simple, but we can identify very specific variables at the portfolio company level to transparently consider which managers and portfolios have a higher level of risk around material environmental, social, and governance issues that affect their viability as good investments.

Second, another big change at Crewcial was our formation of an investment committee. We’re doubling down on our approach, allowing talented team members to focus on what they understand best and follow their passions as investors, but we’re now taking those passions and directing them into somewhat of a more formalized process. It's based on tracking, monitoring, and ensuring individuals get the training they need to scale and fully capture the bigger picture to find the best managers, no matter their initial backgrounds upon entering the firm, while pairing complementary skillsets to bring out the team’s full potential.

Lesson: Don’t be afraid to be different while embracing the fundamental rules of finance. Identify the full scope of everyone’s areas of strength and play off each to build a greater whole. Embrace idiosyncrasies and preferences while being open and honest with feedback and assessments. We do not treat our investment team members as analysts, rather as investors cultivating an owner’s mindset. We're trying to find ways to capitalize on differentiated perspectives to ultimately uncover the difference between market price and fundamental value; seeing things differently, and cultivating an environment in which such perspectives can range openly, is a critical element of that.

We don’t just want the usual suspects from the same handful of schools, we want to expand our collective perspective to include more women, ethnically diverse individuals, and people of all persuasions from different parts of the country or with different educational or experiential backgrounds—talented people come in all shapes and sizes. A diverse team of diverse perspectives is intended to capture the overlooked points of view necessary to uncover the next great idea.


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