Q&A with Thomas Ascher: On Market Structure, Innovation & the Future of Electronic Finance
One of our greatest differentiators at Centana is the strength and diversity of our network. Beyond our own track record and expertise, it’s the operators and advisors we work with, an exceptional group of industry leaders who provide invaluable context, perspective, analysis and support to our portfolio companies. This trusted network is core to how we partner with teams and help drive growth.
To celebrate this, we have launched our Q&A series featuring conversations with members of Centana’s Advisory Board. These accomplished executives act as thought partners, support our portfolio, and bring decades of operating and industry experience to the table. In each installment, we will share their insights on leadership, innovation, and their views on the ever-evolving landscape of financial services, fintech, and related enterprise technology.
In our second installment, we sat down with Thomas Ascher, who has been part of our Advisory Board for more than eight years. Tom continues to support Centana and our portfolio companies with his deep expertise in derivatives, market structure, electronic trading, and guiding innovators who continue to apply technology and transformation to the world of electronic markets and trading.
We’re excited to share Tom’s story, and we hope you enjoy it as much as we enjoyed the conversation.
Q: You’ve been part of Centana’s Advisory network since 2017. What originally drew you to the firm, and what continues to excite you about its portfolio and thesis today?
I got involved with Centana because the relationship came first: I’d known Ben for a long time, and I’d seen how he thinks and how he shows up over time. That matters in this business. You can learn a lot about a firm by how it builds trust and how it behaves when no one is watching. What also attracted me was Centana’s investment thesis, which is partnering with growth-stage companies modernizing the financial services ecosystem and creating long-term value-add change.
What continues to excite me is the consistency of the thesis and the quality of the people around the table. Centana tends to spend time with founders early, stay close to the space, and then lean in when the timing is right. And as markets keep digitizing, the opportunity in “plumbing” and infrastructure only gets bigger — there’s real work to be done, and it’s the kind of work I enjoy supporting.
Q: You were a pioneer in electronic trading and derivatives long before today’s market structure took shape. What first sparked your interest in, and what convinced you this was the future?
Pioneer is an overstatement, but I’ve had the privilege of working with some true pioneers and the pleasure of contributing to some transformational ventures. My interest in electronic markets wasn’t some grand master plan: it started with a curiosity of markets as a kid, and from there grew as I pursued opportunities. Early in my career, I saw firsthand at the Chicago Board Options Exchange, working alongside Ben’s Dad, Aron, no less, how much trading still depended on manual processes and legacy technology. A lot of the institutional inertia across markets was – and often still is – about entrenched stakeholders hanging on to lucrative franchises. Why not bring a laptop into the pit? My personal adoption of better trading tools was less out of frustration with how inefficient traditional systems were and more about trying to make myself more efficient, but away from the pits, the seeds of change were planted.
I’ve always found the concepts underpinning markets captivating: auctions, price discovery, the way information moves. Once you see that software can improve quoting, access, and consistency of execution, it’s hard to unsee it. It was impossible to miss what good software brought to the table, err, I mean pit. That’s what convinced me: not a single moment, but the steady realization that the future would belong to electronic systems that could instantly handle complexity at scale. The true visionaries were already imagining real-time markets on customers’ phones.
Q: From your senior management roles at the International Securities Exchange to shaping listed-derivatives innovation, you’ve helped transform how markets function. What leadership lessons and strategic principles guided you through those shifts?
A big leadership lesson for me is that building a market is never just a technology project: it’s a diplomatic odyssey. You’re aligning incentives across participants who don’t naturally agree, and you’re doing it under regulatory scrutiny. I’ve done plenty of what I jokingly call “boots and shovel diplomacy,” because sometimes the real work is simply bridging worlds and getting stakeholders to the same table.
Another important realization is understanding that most markets are, at their most basic, some form of auction, whether it’s buying and selling cattle or sophisticated derivatives. Strategically, I’ve always believed in being clear about what problem you’re solving and then earning trust through execution. Whether between buyer and seller in an auction or sophisticated market infrastructure, reliability and integrity are everything. The platforms that endure are the ones that combine strong design with strong relationships and a willingness to do the hard, unglamorous work of building credibility.
Q: How do you typically engage with Centana’s portfolio companies, and where do you find you can be most impactful as an advisor?
I try to engage the way I would have wanted an advisor to engage when I was operating: practical, direct, and in service of what the team is actually trying to accomplish. Sometimes that means pressure-testing a strategy, sometimes it’s making introductions, and sometimes it’s just helping a founder think through how the market will react to a product decision. Sometimes the most important feedback might not be welcome, so it’s critical to earn the trust required to consider what that is.
Where I’m most impactful is usually at the intersection of market structure and the final product. Regulated, institutional environments have long memories and high standards, so positioning and sequencing really matter. I can help teams avoid force-fitting a playbook that worked elsewhere, and instead adapt that proven playbook to the context they’re operating in.
Q: You’ve transitioned from operating landmark platforms to advising high-growth innovators. What perspective do you now share with founders that you wish you’d had earlier in your own leadership career?
If I could go back, I’d tell my earlier self to listen more closely – sometimes to simply just shut up and listen. I’d tell myself that leadership is a lot less about trying to be the smartest person in the room and more about becoming an operator who can translate vision into execution. I’ve seen this repeatedly: the founders who can articulate the vision clearly and then build the organization and the habits to deliver on it, are the ones who actually change industries.
I’d also say: stay contextually sensitive. Don’t assume what worked in one market will cleanly drop into another. Learn from adjacencies, yes, but don’t do a force fit. Some of the biggest mistakes (and best lessons) come from ignoring the details that make a market behave the way it does.
Q: Innovation in capital-markets infrastructure often meets friction, from market incumbents to regulatory frameworks. What stands out as the most important skill for leaders driving change in entrenched industries?
The most important skill is building – make that earning – permission — and that comes from credibility. In capital-markets infrastructure, “move fast and break things” does not always win the day. You have to bring regulators, incumbents, and customers along, because the system is designed to protect stability.
That means leaders have to be “aggressively patient” and deliberate: they need to communicate well, understand incentives, and earn trust through consistency. Regulatorily, it takes time. Leaders also need to acknowledge that they are not going to do it alone: to earn buy-in you need to identify critical constituencies and find champions and advocates within each. If you can manage that process without losing momentum or integrity, you have a real chance to drive change in an entrenched industry.
Q: Electronic markets transformed speed and access. As AI reshapes financial infrastructure, where do you see the most meaningful impact in the near term?
AI is already ingesting, parsing and reaching actionable conclusions from the massive data sets being spewed into and out of the markets, but some of the most compelling use cases are far less sexy and anything but unique to this space; AI coding tools are collapsing time to market. Product managers historically have had to write out a spec, then work with engineers, who then write the code. This generation of AI coding tools is, for the first time, empowering people to use plain language to become coders. What that means is a product manager can literally compress the entire product cycle, bringing in engineers at the end to refine and finish the product. That is massively different than before, and far faster and more powerful than anything we’ve seen to date.
At the same time, we have to be honest about what “good” looks like. In market infrastructure, it’s not enough to be mostly right. The systems have to not only be an improvement, but integrate and work seamlessly without any knock-on effects. There is no prize for crossing the finish line first with the wrong results.
Q: Fintech founders often operate inside rule-bound, risk-sensitive environments. Where do you see early-stage teams underestimating complexity, and how can they build credibility in regulated markets?
Early-stage teams often underestimate how much regulated markets run on trust, not just technology. You can build something impressive and still struggle if you haven’t thought through governance, controls, and how your product behaves in edge cases. In this world, credibility is a mission critical feature.
The way to build that credibility is to respect the environment you’re entering. That means investing early in compliance and operational rigor and being able to explain your system: not just sell it. When a team can do that, institutions lean in, because they can see you understand the responsibility that comes with operating in a risk-sensitive ecosystem. At the same time, there can be a tendency to overlook one particularly important constituency: regulators. It is important to remember that regulators are critical stakeholders, and that it’s important to make the case that what is being proposed will make the market some combination of safer, more resilient, and more competitive. The best market solutions solve something for the greatest number of constituents: it’s rarely the same thing for each stakeholder.
Q: Beyond AI and automation, what broader trends in market structure and financial innovation are you watching most closely over the next five years?
Beyond AI, I’m watching how market structure continues to evolve as electronic systems reshape where liquidity forms and how it moves. There’s ongoing change in how venues compete, how products are listed and traded, and how the ecosystem adapts as complexity increases. I’m also paying attention to what’s underneath the hood: the less-visible layers that underpin asset classes, that support counterparties entering into those markets, that follow regulatory frameworks, and so on.
Some of the bigger innovation challenges I see coming are platforms and software that provide opportunities to protect people from themselves, whether in trading, investing, gaming, or simply trusting electronic systems to do what they say they can do. You want your customers to survive and, ideally, thrive. That’s not always the case on some platforms.
Q: You’ve flown a fair amount over the years, both in the back of Boeings and on your own. Tell us a bit more about your time in the air, and what led you to that passion?
Flying started for me as pure fascination — the systems, the discipline, the challenge — and it turned into a real passion. One of the funny things about it is that it often doesn’t feel like you’re going fast until you’re close to the ground, and that’s exactly when you can get yourself into trouble if you’re not careful.
What I love is that it demands presence. It’s technical and procedural, but it also rewards good judgment. For me, it’s a perfect analogical counterweight to markets: the stakes are real, the feedback is immediate, and the learning never stops.
Q: You’ve known Centana partner Ben Cukier for a long time. When did the two of you meet, and have you ever taken him flying?
Ben and I go back a long way — we first met on the CBOE floor, when I was a market maker in my 20s and Ben was in high school. He came to the floor to clerk for his dad. We’ve always stayed in touch. Over time the relationship has grown into a genuine friendship, both professional and personal – they are often one and the same in our business. I’ve always appreciated Ben’s curiosity and his ability to take in complex information and then zoom out to the big picture.
And yes, full disclosure: Ben has flown with me. I’ve taken him up to Vermont, and he did great. Honestly, I think he’d be an excellent candidate to pursue flying himself: the temperament and the discipline are there!
Important Disclosures
The views expressed in this Q&A are those of the interviewee in her personal capacity. The views expressed in this Q&A are those of the interviewee in her personal capacity. References to portfolio companies are provided for illustrative purposes only and do not constitute investment advice, endorsements, or guarantees of future performance.
