This is a transcript of the podcast episode Spencer Gareiss, Roberta Vassallo and the sports assets trading platform featuring the chief product officer (Spencer) and chief legal officer (Roberta) of /mkt and Julie DiMauro, the head of regulatory content (North America) for GRIP in New York.
[INTRO]
Julie DiMauro: Greetings, and welcome to a Global Relay Intelligence and Practice, or GRIP, podcast. I’m Julie DiMauro, the head of regulatory content for North America, speaking from our New York City office.
I’m thrilled to introduce to all of you our guests for the program today, Roberta Vassallo and Spencer Gareiss.
Spencer is the board director, chief product officer, and CEO of Blockchain Market, the blockchain marketplace investing in athletes and tokenized securities.
Roberta Vassallo is /mkt’s chief legal officer.
I cannot do either of their bios any justice, so I’m going to have each of them expand a bit on their great experience before we kick off the program and talk about their endeavors in investing, innovation, and compliance. Spencer, can you kick things off for us?
Spencer Gareiss: Sure thing. Thanks so much, Julie. I’m here with the Global Relay team, calling in from Texas. I started my career at Vanguard in fund management, and then in 2021, I went to Robinhood. I was a product and engineering leader at Robinhood for four and a half years. Co-founded Robinhood Derivatives, LLC, built futures and prediction markets zero to one with the team. Prediction markets became Robinhood’s fastest growing business in history. We did over 200 million in revenue our first year.
Then I built equity shorting with the team. I launched futures in the UK. Then co-founded Robin Adventures LLC and was working on the RVI [Robinhood Ventures Fund] IPO. We were doing late-stage private placements in enterprise software and Fintech companies. Then I left in December 2025, joined the /mkt team, as you mentioned, leading product engineering here and CEO of the broker dealer forward slash financial, waiting for our FINRA license.
I also write about startups in my newsletter at startupspotlight.org. I’m publishing my first book of mental models. By the time the listeners hear this, it’ll be live. Mental Models on Amazon.
Thank you so much, Julie. Glad to be here.
Julie DiMauro: Congratulations to you, and thank you, Spencer. Roberta, please.
Roberta Vassallo: Oh, I cannot compete with Spence, but I’ll try. I am in San Francisco. And I am the chief legal officer here at /mkt. I started my career back in 2009 at FINRA after a couple of years in private practice doing commercial and corporate law. I moved to FINRA enforcement and then stayed about five to six years.
And then I moved to the SEC in the Office of Compliance Inspections and Examination in the San Francisco office, where I was in charge of doing the examinations of investment advisors, investment companies and venture capital. And then after about seven years, I went to the Federal Deposit Insurance Corporation at banking regulations so that I kind of had a full umbrella of regulatory from securities laws to banking.
In my last couple of years at the FDIC, I focused on fintech companies partnering with banks. So therefore my interest in the Fintech, but also when I was at the SEC, I was part of the team that did the examinations of the venture capital firms when the first issues with custody and the digital assets came out. I’ve been in fintech for quite a while and now January I started with /mkt.
Julie DiMauro: Terrific. We’re so pleased to have you both on and to talk about fintech and this company in particular and the innovative products that you’re launching. So let’s get going. Can you tell us, Spencer, about /mkt? What’s it all about? What does it seek to accomplish? And how does its services and products compare to traditional asset backed securities or royalty trusts?
Spencer Gareiss: Yeah, great question, Julie. So, /mkt is an alternative asset trading platform that supports sports assets. So today there’s no access for the retail investor cohort to invest in sports teams, whether that’s NFL, NBA or MLB, the big three or other smaller sports minor league teams. You can invest in athletic departments and you can invest in athletes. People have sports-betting prediction markets. You can go to games. You can buy jerseys, but you can’t actually invest in the sports assets. So that’s the problem that we’re solving.
We’re allowing sports assets to be invested in by retail investor fans. And on the other side, this is great for the owners of teams or athletic department leads because they have an exit ramp and can provide a liquidity event. In doing so, they’re allowing the retail public to invest in their organizations. That’s what we’re building here. Really exciting, at the corner of sports and finance.
Julie DiMauro: It sounds exciting. Now, what you need, though, before you can get going, right, is regulatory approval. And Roberta, this is where you come in. I want to ask you about seeking registration at both the SEC and FINRA. As a CLO of a pre-revenue fintech issue or going through regulation A+, how do you approach building a compliance infrastructure from scratch? Not just for the SEC filing, but for broker-dealer oversight and the ongoing reporting obligations that come after qualification.
Roberta Vassallo: Sure. Great challenge. And /mkt is doing something novel. So, you know, I want to make sure that people understand the regulatory framework that we chose and the reasons why we chose it. Regulation A essentially is what I call a middle path between a full IPO, the initial offering, and a private placement. So it was created by the JOBS Act to make it easier for smaller companies, including, you know, startups, to raise capital from the public.
And so not just from the wealthy accredited investors, you know, but from everyday people. And in particular, tier two specifically allows us to raise up to $75 million from both accredited and not accredited investors. So meaning that anyone can participate, not just the wealthy. In exchange to that type of access to the public, we’re subject to the SEC oversight. And we have to file, you know, the offering statement.
We have to have it reviewed and qualified by the SEC. And then, of course, we have to file the ongoing annual and semi-annual report, just like a public company. It is a regulated public offering, just with a lighter touch.
And even if it’s not a full IPO, it is the type of structure that help to have the protections, you know, built in for the investors. And for market, that was the right choice because our mission is to, what Spencer said, is to open up the athlete investment. We want fans, we want communities and everyday investors to be able to participate and not just the institution.
Building the compliance infrastructure means thinking kind of in layers, like you said, Julie, and the offering itself has to be qualified by the SEC before a single dollar is actually raised. And then the broker-dealer layer through our FINRA, member forward slash financials, you know, handles the customer relationship and the suitability. And our partner, tZERO, they provide the trading and the custody infrastructure on the back end.
But what makes our approach interesting, kind of to finish up and to answer your question, is that most startups nowadays try to avoid the regulation as long as possible. You know, we actually went toward it for lack of a better word because we believe that it is, you know, the only way to build something that actually will last in this space.
Julie DiMauro: Absolutely. And it gives you a lot more credibility in the marketplace. Absolutely. Just a related question for you, Roberta. The road to becoming a broker-dealer involves other dynamics, right? From pricing to team composition, how do you determine what those features look like?
Roberta Vassallo: Yeah. So our FINRA application and the FINRA new member application, also known as the FINRA NMA [New Member Application], is very rigorous by design. And FINRA, they want to know that you have the right people and they want to know that you have the right system and that you have the right capital before you’re even allowed to hold any customer funds or execute any type of security transactions.
So for us, that means showing that our compliance program is real and it’s not just, you know, on paper, that our principals have the right licenses and Spencer has a lot of them. So we’re really proud of Spencer. He’s a great asset for us. And, you know, clean regulatory histories and that our business model is clearly sustainable. So pricing and team compositions are certainly part of the conversation. So basically FINRA wants to see that the economics make sense and that the people running the firm know what they’re doing.
Julie DiMauro: On the private placement side, Roberta, a non-public unregistered sale of securities to institutional investors or accredited individuals, what needs to be demonstrated to the regulators in that area?
Roberta Vassallo: Now, do you got to allow me a little bit of time because this is, you know, one of my favorite topics, right? So please excuse my lengthy answer.
So in a private placement under Reg D, we are raising capital without registering the offering with the SEC, but that doesn’t mean that anything goes right. So the SEC has very specific rules about whom you can sell to and how you can find them. And there are two main, let’s say, flavors. There’s the rule 506(b) that is the traditional private placement. It is unlimited capital, but you cannot advertise or generally solicit to the public.
You have to have what we call the preexisting relationship with your investors. So you can include up to only 35 non-accredited investors. Rule 506(c), which is what we are doing and market is newer. It came out with the Jobs Act and it allows you to advertise and generally solicit, which is a big deal for companies like us, you know, trying to reach a broader audience.
The catch is that every single investor must be accredited. And you as a company or we as a company have to take reasonable steps to verify that. We cannot just take their word for it. But in both cases, so the core application is the same. So the investor protection without full public disclosure. You need to demonstrate that your investor, so the company has to demonstrate that the investors meet the accredited investor thresholds and that none of the covered person or the key personnel of the company have any disqualifying bad actor events and that our disclosure documents tell the investor the truth about the risk.
So the regulators essentially ask one question, which is what I ask myself all the time when I was at the SEC. Did you sell this to the people who can afford this or can afford to lose, to lose anything? And did you tell them the truth? Basically, those are the main two questions that we need to answer. There’s a lot of due diligence involved in this process, though. Lots of due diligence and we’re very good at it. We take it very seriously and market.
Julie DiMauro: I can tell. And Spencer, I am really fascinated by this novel financial marketplace here, tokenized athlete-earning securities. How do you approach the legal characterization questions involved with your enterprise that have no direct precedent?
Spencer Gareiss: Yeah, great question, Julie. We’ve approached this from the beginning as a securities business. That’s why we went with the introducing broker dealer and placement agent licenses. We felt like those activities were supporting what we wanted to accomplish. And then, of course, the instrument itself, the HOWEY test has been around for a long time. Our team is very familiar. We felt a simple HOWEY test defined our product as a security.
And then when the CFTC and SEC came together recently and defined the five different types of products, it was abundantly clear that we did have the one that was considered a security. So we’ve got a digitally native token, but the instrument itself is still considered a security and regulated as such. And that’s why we do the qualified offerings and the filings with the SEC. And that’s why we work with FINRA and are working on getting our FINRA license.
Julie DiMauro: That makes sense. But let’s go to the CLO, Roberta, for her take on that!
Roberta Vassallo: That was already perfect. Exactly what I was going to say. I can add that athlete income securities do not have a direct precedent, like you said, in case law or because I was the SEC, I have to say there are no action letters, no precedent, no-action letters. So what we did is we built the analysis like Spencer said from first principles. We went back to the HOWEY test. The novelty here, I want to finish what Spencer said by saying it’s not the legal characterization because we determined that under the HOWEY test, they are securities. It is the asset class itself that was different.
So we stuck with what we knew the regulatory regime was. And we just had to link the new asset class itself to what we knew that the regulatory regime was.
Julie DiMauro: Absolutely. Now, Roberta, I want to go back to something that you said to me before and get both of your responses to it. You said the law is always behind the market and someone needs to go first. Is that part of the premise behind your enterprise, going first but doing so with proper oversight and guardrails?
Roberta Vassallo: You know, when you spent almost 20 years like I did as a regulator at SEC, FINRA and the FDIC, you see this pattern kind of over and over again. A new market emerges, investors move fast, and the law itself scrambles to try to catch up. Sometimes this works out, sometimes it doesn’t. We might all remember what happened in 2017, 2018 with the ICO, the initial coin offering. Billions were raised, almost no regulatory framework. And a lot of people, frankly, got hurt.
The law eventually cut up and I was at the commission when the SEC eventually stepped in and said, hey, they took the position that most ICO tokens were securities under the HOWEY test, meaning that they should have been registered or sold under the exemption. But the damage was already done by then. So what we are doing at /mkt is different. We looked at the athlete income securities and we asked ourselves, is there a way to build this that doesn’t wait for the law to catch up?
So that’s why we did. And the answer was yes. So HOWEY has been the test for the security since, I want to say 1945, 1946.
So it’s not ambiguous when you apply it honestly to what we’re doing. So athletes have careers, investors are buying a share of that career’s financial output and that’s a security, full stop. So going first for us doesn’t mean going rogue. You know, it means being the company that shows regulators, show investors and the market that this class, this asset class can be done right with proper disclosure, with proper broker-dealer oversight, which is what we’re doing with the application to FINRA, with proper custody through our partner tZERO and the proper ongoing reporting. So we’re not asking for forgiveness later.
We’re asking for qualification now. And honestly, this is harder. It takes longer. It costs more, but it’s the only way to build something that actually survives.
Julie DiMauro: That makes sense. Spencer?
Spencer Gareiss: Yeah, I thought that was great. I think the true test for if you’re really innovating in the financial marketplace is if the regulators are having to shape their regulation around what you’re doing as a business. And that’s what I’ve been doing my entire career. I think the second thing is that I’m really passionate about is the velvet rope that’s around so many investment products shouldn’t be there. And I’ve spent my career taking down the velvet rope so that retail can walk that path as well. And that was futures. That was futures in the UK.
We filed the part where the first retail brokerage launched futures to the UK demo. UK clients had never had access at the retail-evident futures until we launched it. Prediction markets. As soon as the CFTC rule change happened, we actually shifted mid futures build to prediction markets and launched that first. Equity shorting. Hedge funds have had access to equity shorting forever. Well, when we launched equity shorting, it was removing that velvet rope so that the retail public can have access to that investment product or strategy.
And so the thesis is the same here. We truly believe that retail should have access to sports assets. If you’re a billionaire, you can buy a sports team. You shouldn’t have to be a millionaire to buy a sports team. And so that’s why we’re doing what we’re doing and unlocking access to the retail public. And we believe in doing it the right way. And so to Robbie’s point, structure it in such a way that meets the current requirements and then use the foresight to structure it in a way that it’ll last regardless of rule change. So that’s where we are.
Julie DiMauro: Absolutely. And where you are is doing it now with an administration, right, that is open to innovation and to greater access to more people, to more investors and an opening of marketplaces. Seems like you’re doing it at the right time as well. How does that play a factor?
Spencer Gareiss: Yeah, look, timing is everything. If NIL wasn’t the case, if teams weren’t, you know, being more open to outside investors, if social media didn’t have the virility, if you didn’t have, you know, these alternative asset marketplaces that are emerging, right? There’s marketplaces for different segments, whether that’s wine watches, art, right? We believe there should be a centralized marketplace for every alt segment. There isn’t one today for sports. And so we think the timing is right. You know, you’re seeing salary caps in the WNBA going up 7 times.
You’re seeing new leagues emerge, whether that’s pickleball, right, or something else like Slamball. And that’s really exciting in the sports space. And fintech has been doing amazing for the past decade. So we think, you know, the infrastructure is there, the timing is right. You know, it couldn’t be better.
Julie DiMauro: Absolutely. Spencer, just to dovetail a little bit on that, as a fintech firm, you’re using technology. How specifically are you leveraging artificial intelligence to deliver results without burning through your cash, which must be hard, and while monitoring the possible risk that AI can introduce, some of those novel risks that it can introduce?
Spencer Gareiss: Great question, Julie. Our team uses AI a lot, and I think it’s a massive force multiplier. You know, anecdotally, I built our active trading user interface, which is about 15% of the technology, right? 85% is back-end infrastructure, connectivity with the exchange, all of that stuff. But I built that UI [User Interface] in one day in a coffee shop using Figma Make. That used to take me and a team of five product designers, you know, three months to put together all of those screens, wireframes style, even with Figma.
So with AI, you know, that condensed the five-person, three-month task into a solo task, and I was able to do it in four to eight hours in a coffee shop. And so across, you know, the entire spectrum of our business, that’s been the case. We’ve built out an AI driven underwriting tool that we’ve actually also productized and could sell it to agencies and teams. And really, instead of hiring 10 underwriters and paying them six grand a year to underwrite all these sports assets, we’re using technology to create more robust, accurate underwritings in under two minutes. And so those are just some of the examples of how we’re using it to condense timelines and save money.
Julie DiMauro: That sounds great. Roberta, anything on that?
Roberta Vassallo: Well, keep in mind that not everybody can do it in a coffee shop like Spencer. It’s him. He was just thinking that. I’m just going to say that’s just all I wanted to add because people may think, oh, I can do it too.
Julie DiMauro: Ha, quite true! Roberta, for a company that’s generating public interest before its offering is qualified through social media, press, athlete announcements, how do you manage the line between building brand awareness and crossing into offers of sale before the SEC has qualified your offering statement?
Roberta Vassallo: Yeah. Thank you, Julie. This is very important and is one of the most practically important questions in our world right now. So under Reg A plus rule 255, you’re actually allowed to engage in certain pre-qualification communication with the public. And this is what the SEC calls testing the water. But there are very, very specific rules about what you can do or what you can say or what you cannot say.
And this is something that at /mkt, we had to instruct our younger marketing people on what to do because, you know, our marketing people, they’re all like, let’s go get them. Let’s go do it. We have to be very careful about what you put out there.
For instance, you cannot make offers of sales. You cannot quote a price. You cannot create the slight impression that the offering is already live. What we can do is simply generate interest, build a community, educate the community on what’s coming and somehow communicate our vision, the vision of the company.
Every piece of external communication, social media, press release, athlete announcement, everything has to go through a very specific compliance review before it goes out. And when I say compliance review, I mean, has to go through me, has to go through our CCO, has to go through Spencer, has to go through Marcus CEO, Ben Turner. So there are a lot of levels of review. So we take to this line is real and we take it very seriously.
Julie DiMauro: Now, can you both walk me through a little bit like where you are in the timeline? So what can we expect maybe in the summer and the fall? What are the next goalposts?
Spencer Gareiss: Sure thing. Yeah, good question, Julie. We are most importantly waiting for that FINRA broker dealer license. So we had the FINRA demo, which is a huge milestone for the team on Wednesday. That’s where we’ve got to show FINRA. What does the platform look like? You know, does it meet the expectations? The response is really positive. We’ve got the, you know, big comment letter that’s typical, right?
A big package. I think it was 83 artifacts or so. It’s, it’s essentially an exhaustive list of what they can ask for. And this is, this is what Roberto was mentioning. The bar is very high, right? This is where a lot of people fall off. They make it hard to climb. So we’re going through that. There’s a six-month requirement. So we filed and received substantially complete response from FINRA on May 6th.
So by November 6th, legally they have to either approve the BD or reject it. And we think it could be much sooner. The white house recently put out guidance advising the SEC and CFTC and other organizations to support fintech growth, to not be more liberal, but be more understanding and expeditious with respect to getting people, you know, through the machine, if you will. I feel bullish on, you know, getting that license, of course, no later than November 6, but potentially sooner. And while that’s happening on the reg side, since technology is in a great place, we’re really just pushing on business development.
We’re working with a lot of issuers, different teams, athletic departments, figuring out what are their capital needs. And then how can we structure an instrument that really serves their purpose, which is where the, that revenue participation note that we’ve discussed or the royalty certificate.
Essentially, these issuers are getting money via our platform from their investors without it hitting the cap table, without it hitting debt covenants. Because it’s not a classical equity or debt instrument, it’s really a gross income encumbrance. So we’re, we’re just structuring things as well as we can with those issuers and making sure that that deal flow is really sound so we can bring really close to the public when we go live with that BD license.
So expect us to go live this year, expect some really interesting offerings, both on the athlete side and on the institutional team side. I think it’s going to be really interesting and we’re excited to see how the retail investors respond to it.
Julie DiMauro: Fantastic. Roberta, I want to ask you a little bit about your career trajectory, especially since you and I go back in time and I’ve known you serving at some of these agencies that you described – FINRA, SEC and FDIC. How was it to go from US regulatory agencies into working at a startup, so from regulating to being regulated?
Roberta Vassallo: That’s true, Julie. We go back, we go back a while. That’s right. You know, honestly, being a part of these agencies for so many years was probably the best preparation I could have had. You know, when you spend so many years at the SEC and FINRA, basically sitting across the table, you know, from, from, from companies like mine and going through exactly what /mkt is going through, you develop a very, very clear picture of what regulators are looking for and not only what they’re looking for, but what flags are raised. Right.
So the transition itself was not as dramatic as I thought it was going to be, because the underlying mission is basically the same, investor protection and market integrity for, for regulators. And of course for us too. The difference is that now I am building the systems rather than reviewing it. When I was at the, at the agency and I’ll, and I, I say, you know, having been on the other side, uh, makes me a much more demanding compliance architect. I think that Spencer would probably agree with that. I know exactly what a regulator would ask.
And I make sure that I have those answers before they do. And that means sometimes being, I call myself a Debbie downer when you know, with the team, because we’re all excited about saying, I’m like, well, we gotta be careful with that, you know, because I’ve been there and I know that three questions will be asked, issues will be raised and, uh, I want to anticipate it. Fantastic.
Julie DiMauro: Spencer. I want to ask you about your background. It includes a wealth of product creation and tech engineering components in your current role and at Robinhood. What made you want to take that experience in co-found /mkt and how do you want users to experience /mkt from a product and tech aspect?
Spencer Gareiss: Really good questions and blessed and fortunate for the past experience. Right time, ight. And thanks to everyone who poured into me to get here. I wanted to take the leap of faith because I had been an intrapreneur, which is an entrepreneur that works within formal organization, right? Not a true, not a true entrepreneur. You have some safety nets, right? You, the firm has capitalized the overhead is not something that you need to organize or bear the financial burden of being an entrepreneur for me was a test to see if I had the, you know, the intestinal fortitude and the chops, if you will, to do it myself, or was I successful because of the team that I was surrounded with at Robinhood?
You know, at times I thought anyone could be successful in this group, you know, just by association. So it was really a test. If, if my success was a derivative of the Robinhood crew or if I, you know, had, had something special. So I wanted to take that leap and Ben Turner founder and CEO, you know, we shared a lawyer and the lawyer had, had told Ben, Hey, you should talk to Spencer and see if a lead product in engineering. Ben’s idea was ambitious and crazy enough for me to take that, take that leap of faith. I wouldn’t have, you know, I had built prediction markets already at this point, which was crazy and successful.
So I wasn’t willing to do anything that wasn’t substantially crazy. A new asset class, groundbreaking alternative asset trading platform. It checked the boxes, you know, from a narrative standpoint and I had faith in the team. So here I am and we’ve been having fun building.
Julie DiMauro: Absolutely. That’s great. Now I want to ask each of you to answer this question, what you’re most excited about in the second half of 2026. And you kind of alluded to that Spencer and giving us the timeline, but also just for inspiration for other people out there who might want to be entrepreneurs and start up something innovative. Why is this a great time for tech finance ventures like yours? What would you tell them?
Spencer Gareiss: Keep building the future, stay positive. You know, there’s lots of challenges to overcome. I would say build what’s true to you. The dollars that VC firms are posting, the trends in media, all of these things are ever changing. And so you could find yourself on an, on a never ending treadmill of chasing what’s hot.
I think, you know, like Robbie described our regulatory stack, right? It was built to last forever. If you build to your passion and what you truly are convicted on rather than what you think is, is popular or hot. I think that’s how you build a company that you can own and operate for 30 plus years, which should be the goal. You know, if you’re founding something, of course you could exit. That’s a beautiful moment for any founder, but it’s such a hard road that.
When you start, it has to be something that you’re willing to do for potentially 20 years, if, if you’re going to even start. So keep building the future.
Roberta Vassallo: I couldn’t have said it any better. I certainly, what I’m excited about is the FINRA approval and the qualification that is coming up to that we’re working on. So those are certainly the two milestones that take /mkt from a company with a vision, I would say to a company, you know, with a live offering. So the second half of 2026 is when that foundation that we started now, you know, starts to show what, what it was built for.
Julie DiMauro: And words of wisdom to anyone that might want to follow in your footsteps, some either going from private industry into something tech startup type of infrastructure, or maybe going from a regulatory agency, a public agency. What would you say to them?
Roberta Vassallo: Well, for me, take the, take the leap of faith. It is a, it is a wonderful way to grow as a, as an attorney in my case, as a, as a professional, and it’s a wonderful way to challenge yourself. Like I said, it was the best for, for me, it was the best move being at an agency, at a regulatory agency certainly gives you, you know, the best kind of background and, and experience to be successful now in this new venture.
Spencer Gareiss: I’ll echo that too. I want to encourage the government workers, agency workers, right. Whether that’s SEC, FINRA, CFTC, NFA, etc., to continue to lean into helping builders in fintech. I’ve seen a trend of, you know, the public force moving into private and supporting startups in fintech. And it’s really matured the regulatory posture of Fintech startups over the past 10 years, because those professionals are in those organizations.
So, you know, as a fintech builder who relies on people like Roberta, keep being open to the startup space, the upside’s massive, and we really need you so that we can continue to build innovative companies, you know, with correct regulatory stacks. So thanks for all of the public workers who are shaping the future of regulations, and I hope to see you on the quote unquote dark side.
Julie DiMauro: I love this. This is great. Great energy. You compliment each other so well, which is lovely. I’m very energized by what I’ve heard, and I’m sure our listeners feel the same way. So thank you so much, Spencer Gareiss and Roberta Vassallo, both from Blockchain Market for being on the GRIP podcast program today.
Please come back and share more exciting news with us at the end of the year.
Spencer Gareiss: We will. Thank you, Julie.