Regulation is a Contact Sport
In this episode of FinTech Focus TV, Toby sits down in New York with Stan Yakoff, Co-Founder at RegLabs.ai, to explore a subject that many financial institutions fear, misunderstand, or underestimate: regulation. What begins as a conversation about compliance quickly evolves into a discussion on sport, technology, education, and the mindset required to survive in a rapidly changing digital trading landscape.
Stan describes working across nearly every continent with one exception, joking that “hopefully one day” he’ll get a chance to engage the penguins in Antarctica. During those years, Stan built first-line and second-line risk and control systems from scratch. He estimates that he handled more than a thousand regulatory inquiries and twenty-four regulatory exams, moving between markets, asset classes, and challenges. Somewhere along the way, he stopped asking how to respond to regulators and started asking how to anticipate them. His goal: predict the worst day a firm can have, long before it arrives, and build systems so that day never comes.
The FinTech, AI and Crypto Landscape: Why Compliance is More Than Protection
Toby probes the conversation toward the external forces shaping the modern financial system. Today’s financial markets are a dense intersection of technology and innovation. Artificial intelligence is accelerating at a pace that changes expectations on a monthly basis, and digital assets continue to reshape regulatory frameworks as TradFi and DeFi inch closer together. Stan acknowledges that the crypto and digital asset world has forced regulators to react, evolve, and rethink their previous structures. The AI boom has done the same, introducing new standards of scrutiny, market behaviour, and potential misconduct. To operate in today’s financial ecosystem, businesses must do more than interpret past regulatory action. They must predict what is coming.
For Stan, this is where RegLabs.ai was born. He believes that regulatory problems cannot be solved at surface level. They must be studied in depth, with the same analytical precision used in competitive sport. He compares the environment to modern sports organisations, which analyse performance before players ever step onto the field. They examine risk, patterns, and probabilities, then adjust strategy. In markets, he sees the same pattern emerging. Today, firms can no longer wait for regulators to intervene; they must anticipate how regulators will examine them, where weaknesses will appear, and what an enforcement action might look like if they do nothing. He explains how that view is not theoretical, but deeply practical. He has lived it through more regulatory interactions than many legal teams see in a lifetime.
From Elite Trading Firms to Building RegLabs.ai
Stan details the turning point that shifted him away from institutional roles and into entrepreneurship. He had watched countless new business initiatives inside financial institutions stall because of compliance ambiguity. A bank could take eighteen to twenty-four months to move a project forward. A smaller, leaner firm might take nine to twelve. The culprit was rarely technology. It was uncertainty around the regulatory frameworks governing that technology. When you dissect the problem like an athlete or coach reviewing a loss, patterns emerge. Firms spent months simply trying to figure out how compliance would treat new activity, how regulators might react, and which risks mattered most. Stan realised that if he could demystify this process and predict the high-risk areas ahead of time, he could shorten the go-to-market cycle dramatically. That would not just protect firms. It would drive revenue faster and earlier.
He challenges the way compliance is perceived. People treat it like a cost centre, a burden or an obstacle to innovation. But Stan argues that if compliance is executed intelligently, it becomes a revenue accelerator. It prevents delay, protects expansion, and removes strategic uncertainty. More importantly, by anticipating regulation early, firms avoid the surprise factor. There is no 4:30 PM email ending in “.gov” that suddenly throws the business off course. When that knock does come, the firm is ready because it has already modelled the scenario.
RegLabs.ai is his attempt to systemise that approach at scale. The platform collects regulatory information globally and analyses it using the mindset of a practitioner. Stan notes that if a firm operates across jurisdictions, it may need to manage eight hundred to twelve hundred different regulatory data inputs, ranging from speeches to risk alerts, enforcement actions, thematic reports, filings and more. Each of those inputs matters because it signals what regulators care about. Stan and his team collect, organise and study these datapoints with the same methodical discipline he once applied to trading organisations. They examine what went wrong in enforcement cases, why it went wrong, and how regulators reacted. Like sports, where performance is often defined by the mistakes a team learns to avoid, compliance is shaped by the lessons that organisations fail to internalise.
The Educational Mission: Preparing the Next Generation of FinTech Leaders
Beyond the commercial mission, Stan has spent seven years teaching at Fordham Law School. His class on trading, risk management, market structure and regulation exposes students to real-world experience, not textbook theory. He wanted to give students insight into what life will be like inside a trading firm or a top-tier law practice, particularly as AI continues to reshape legal and compliance work. Fordham embraced the idea and gave him the runway to build an innovative curriculum. Rather than teaching abstract law, he equips future lawyers, CCOs and risk professionals to understand regulators like engineers. They must learn not just the rules, but the behavioural patterns and decision-making frameworks behind them.
He summed it up clearly: when he was writing the syllabus, his focus was on the skills students will actually need the moment they walk into the job. He describes a classroom environment where students witness speakers like Paul Atkins, former SEC Chairman, or attend major crypto and blockchain symposiums. They get exposure to the realities of regulation in practice. They understand the problems trading firms face and how compliance teams must navigate them.
Stan emphasises a favourite expression among educators and athletes alike: “be the change you want to see in the world.” He explains how many students suffer from poor-quality teaching, and how that experience drives people to teach differently. He is trying to create a pipeline of future practitioners who are both technically capable and pragmatically aware, professionals who understand the market they are entering.
Data, AI and the Philosophy Behind RegLabs.ai
When Toby presses further into the mechanics of RegLabs.ai, Stan explains that the platform is not just a fancy dashboard. It is built on twenty-five years of regulatory data, covering one hundred and fifty-five regulators across more than thirty countries and ten languages. The platform simulates how regulators examine firms across roughly six hundred and forty different compliance and risk topics. This allows institutions to automate risk assessment, prepare for examinations, and study what fines or enforcement actions might look like on specific issues like AML.
This is also where Stan draws a line between serious engineering and superficial AI. He criticises the trend of using black-box models on poor-quality data. Many companies shortcut the foundational work and then act surprised when their AI initiatives collapse. Stan treats data like bricks in a pyramid. You lay them one by one, carefully and scientifically, because small deviations can destabilise the entire structure. He says the biggest mistake firms make is skipping the bottom-up discipline and then throwing AI at the top. Without a foundation of clean, organised, practitioner-relevant data, the entire implementation becomes fragile. When he smiles and says he did the analysis “with a smile,” he acknowledges that few others would. But that is the difference between a product that works and a product that looks attractive but fails when regulators make contact.
Founders Helping Founders: A New Culture of Collaboration
The second half of the discussion becomes surprisingly reflective. Toby asks what Stan has learned in his first nine or ten months of entrepreneurship. Stan explains that the biggest surprise was discovering how many founders quietly share similar problems. They often operate in different verticals, but their clients, pain points and strategic dilemmas are connected. When he speaks to a financial services institution struggling with regulatory change management, he might also hear frustration about market data. Stan will then suggest another founder solving that specific problem, because if someone appreciates his analytical approach, they will likely appreciate that founder’s solution too.
He rejects the idea that startups must be insular. Many new founders put their heads down, obsess over burn rate, and operate in isolation. They adopt a “me, me, me” mentality out of fear, thinking that survival depends on doing everything alone. Stan argues that this is the slowest and loneliest path. In modern financial technology, there is no single enterprise platform that solves everything. Solutions are a tapestry. The firms that win are the ones that work together, share networks, and understand when to pass the baton to a specialist.
Toby connects instantly with this mindset. As the CEO of Harrington Starr, a business deeply embedded in FinTech recruitment, he has seen hundreds of founders risk everything only to fall victim to distraction. He recalls his own experience early in the company’s life, when they pursued work that sat slightly outside their lane. It diverted attention from the core FinTech recruitment strategy and cost months of momentum. That lesson remains embedded in how he advises founders today. The biggest mistake he sees is spreading capability too thinly, trying to do everything, rather than becoming exceptional at one thing.
Stan agrees, citing trade surveillance vendors who claim to provide holistic solutions. They merge trading and communications surveillance but only achieve mediocrity in both. Regulators, like Olympic judges, grade each discipline separately. You can win gold in one category and still fail the overall competition if another core discipline collapses. Stan's solution is to build depth over breadth. RegLabs.ai solves a single problem exceptionally well and will not chase new categories until the foundation is strong. When asked if the platform will eventually cover congressional bills or legislative processes, Stan says yes, in due time. Not now.
Why Regulation is a Contact Sport
Throughout the conversation, sport is a recurring theme. Stan describes regulation not as bureaucracy but as a physical impact. You get hit. Repeatedly. If you do not learn from those collisions, you get hit harder. Athletes review performance, identify mistakes, and adapt. Traders and compliance teams must do the same. The only difference is the consequences. In markets, the punches land in the form of fines, investigations, operational freezes and reputational damage. The only way to survive is to anticipate contact, brace, and counter.
Stan shares how often founders ask if RegLabs.ai can be used to make bets. The question makes him laugh, but the analogy is not far off. If you understand regulator behaviour as deeply as a quant analyses spread betting, you can predict the probability of enforcement and act accordingly. It is a competitive advantage. It is data-driven risk management. It is Moneyball for compliance.
When Toby asks who should reach out to RegLabs.ai, Stan lists an almost comical array of institutional categories. Trading firms, investment banks, hedge funds, private equity, capital markets, energy companies, state and commercial banks, insurance firms, and even money service transmitters. Then he pauses, knowing how exaggerated it sounds, and laughs that “we are going to start a song at this point again.” But behind the humour lies an important truth. Compliance touches every vertical of the financial ecosystem, and modern regulation does not care where a company is located. The UK, EU and US now pursue extraterritorial policies. If a business touches their markets or their people, it is in scope.
RegLabs.ai also works with large law firms. These firms look at the system not just as technology, but as a “golden source” for regulator behaviour. Stan says it is refreshing to be contacted by people whose email addresses do not end in “.gov,” joking about the tone of previous interactions where requests were authoritative, exhaustive and urgent.
The Future of FinTech Regulation: Anticipation Over Defence
This episode makes one message clear: regulation is no longer defensive. It is proactive, predictive and strategic. Compliance has transitioned from a burdensome department to a critical enabler of growth. The businesses that understand this win faster, launch quicker and scale without fear. The businesses that react late invite disaster.
In markets defined by AI, digital assets, cross-border business and competitive hiring, anticipating regulation may be the most valuable capability a FinTech company can possess. Teams that understand compliance become more attractive to investors, regulators and prospective employees. They avoid the career-limiting consequences of mismanagement and build cultures of resilience, transparency and foresight.
As a FinTech recruitment partner to the industry, Harrington Starr sees this evolution firsthand. Firms are no longer hiring compliance professionals simply to tick a box. They are hiring risk managers, regulatory technologists, data scientists and legal strategists who can anticipate contact before it arrives. Like elite athletes, these leaders understand that survival depends on readiness, discipline and preparation.
Stan’s journey, from tennis courts to trading floors, to the classroom and now to advanced regulatory simulation, reinforces a central truth. FinTech is not just a technology sector. It is a competitive arena. Regulation is not paperwork. It is a contact sport.
