✍🏽 Landon’s Loop #148

What’s in the Loop:
🎙️ Chicago Futurist Vol. 9 with Edward Woodford, Founder & CEO of zerohash
👼 Chicago Needs More Angel Investors
📅 4 Events in Chicago This Week
🚙 My Interview with Fox32 about Waymo in Chicago
🎙️ Chicago Futurist: Edward Woodford, Founder & CEO of zerohash

Edward Woodford founded zerohash on a simple thesis: if value is going to move on new rails, someone has to build the infrastructure.
Today, zerohash allows platforms to launch stablecoin, trading, and tokenization products while abstracting away custody, compliance, and settlement. The infrastructure supports millions of end users globally.
When approached with a multi billion dollar acquisition, Edward chose to keep building.
Here’s our conversation:
What problem were you originally obsessed with that pulled you into digital assets
EW: I’ve always been drawn to market structure and solving structural problems in financial systems, particularly the ones most people self select out of because they’re complex and unglamorous. The parts of finance that matter most are often the least visible, clearing, settlement, and how value moves beneath the surface.

When I was at MIT, I was exposed to Bitcoin through a class taught by Christian Catalini. What struck me wasn’t trading or speculation. It was the idea that the way value moves could be redesigned. That felt like a rare moment where a foundational layer of finance might change. It was clear to me that blockchains represent a step change in infrastructure, a fundamentally new way of moving value globally.

zerohash went through multiple names and iterations before becoming what it is today. What was the earliest version of the company trying to do, and what did you get wrong at the start
EW: Like many early companies in the space, we initially thought the opportunity was in a D2C trading platform. We started by trying to build an exchange for institutions, because at the time that felt like the obvious opportunity.
Customers quickly told us they didn’t just need another venue - they needed everything behind it: custody, compliance, settlement, licensing, and connectivity. They wanted infrastructure that allowed them to enter the space without having to build it themselves. Once we shifted our focus to that layer, the direction of the company became much clearer.
That pivot also shaped our long-term thesis. We came to believe that blockchain technology wasn’t just about a new asset class - it was about rewiring how value moves globally. Trading is one small piece of that. Stablecoins, payments, treasury and tokenization turned out to be large and complementary opportunities, and today they represent a significant portion of our business.
You argue trust is the real moat, not the technology. What does trust mean at enterprise scale
EW: Trust at enterprise scale is built through execution, not messaging or marketing. It means systems performance reliability under stress, assets settle when they should, regulators understand the framework, and partners know risk is managed appropriately.

Technology can be replicated, but trust compounds slowly over years of consistent performance. In fintech, especially, you cannot “fail fast” in the way many technology companies can, because licensing, regulatory engagement, and institutional relationships take time to build.
The upside is that once trust is established, it compounds. Some of the largest and most complex financial institutions in the world work with us today because we invested early in building that foundation. In our world, we don’t sell to engineers first - we sell to risk committees.
Every major network scales once interoperability takes hold, and stablecoins are entering that phase today. What does true interoperability look like in practice for money, and who benefits most when that transition completes
EW: True interoperability means that value moves across networks as seamlessly as information moves across the internet. Users and businesses shouldn’t need to think about which chain, ledger, or payment rail is being used - that complexity should be abstracted away.
Early SMS is a good example. Initially, you could only text people on the same carrier. Once networks connected, usage accelerated dramatically. Blockchain networks are entering a similar phase.

When interoperability is achieved, the biggest beneficiaries will be businesses and consumers, because capital becomes more efficient, payments become faster, and global connectivity becomes the default.
When markets move or cultural moments spike demand, money velocity suddenly matters. How do partnerships with Kalshi change the expectations users now have about how fast money should move
EW: Technological innovation has conditioned us to expect immediacy. People increasingly expect financial systems to behave like the internet - real time, 24/7/365, and global.
When people can fund an account, transact and withdraw instantly around events that matter to them, that becomes the new baseline expectation. Financial infrastructure historically optimized for batch processing and settlement cycles measured in days. Increasingly, the expectation is real-time movement of value, 24/7, and platforms that enable those experiences accelerate that shift.

You walked away from a multi-billion dollar acquisition. What did you see in the next two years that made independence the rational bet
EW: We’ve been approached numerous times by serious acquirers. What keeps us independent is the belief that we can build more in the next two years than we have built over the last 8.

It feels like the industry has reached an inflection point. Stablecoins, tokenization, and institutional adoption are accelerating, and the infrastructure layer is becoming increasingly important. As an independent company, we believe we can have materially more impact.
Chicago is a market structure city, from grain pits to derivatives to electronic trading. How has building zerohash here shaped the way you think about financial infrastructure
EW: Chicago has a deep institutional understanding of how markets function at a structural level. There’s a long tradition here of clearing, settlement, and risk, the plumbing of finance, not just the products built on top of it. That perspective is invaluable when you’re building infrastructure, where the hardest problems are often operational, regulatory, and structural rather than visible to the end user.

There’s also a certain grittiness to Chicago and a culture of builders who are comfortable doing difficult, unglamorous work over long periods of time. Infrastructure businesses are built that way. They require patience, discipline, and a long-term view.
Chicago has an opportunity to be a major center for shaping how these systems operate. The city has a strong tradition in market design, financial engineering, and risk management, and those skills translate directly to building the next generation of financial infrastructure.
We want to play our part in attracting the best and brightest builders, operators, and thinkers in financial infrastructure to come to Chicago and build with us. Cities that lead in new eras of finance do so by attracting talent and fostering collaboration, and we believe Chicago is well positioned to play that role in the years ahead.

How can Chicago’s tech ecosystem improve
EW: Stronger connectivity between founders, investors, financial institutions, and operators would accelerate innovation.
Cities that lead in new industries tend to create tight feedback loops between builders, capital, and customers, and that’s an area where continued progress can make a meaningful difference. We need to be better at showcasing talent - something I am working on is zerohash financially support “startup on the mart”, where founders and builders can showcase their work on one of the biggest screens in the world. I want to help change the dialogue that every big announcement has to be announced on the Coasts.
For example, when we raised our Series D last year, the natural rite of passage was to head to New York for TV interviews and photographs with the NYSE and Nasdaq showcasing our raise on their big screens.

What’s your favorite metric to follow on the business
EW: I focus on metrics that reflect real economic activity rather than assets sitting idle. In stablecoins, there’s often a tendency to focus on AUC, assets under custody, which is money at rest.
What matters more to me is TPV, total payment volume, because that shows money in motion. It tells you how frequently customers are actually using the infrastructure and whether it’s solving real problems. Stablecoins are gaining traction in instant account funding, merchant settlement, payroll, remittances, and B2B treasury flows. The common thread is velocity and utility. Those are best measured through usage and volume, not balances.
Edward wrote a children’s book called “Stablecoins for Babies” All profits go to the Reading Is Fundamental literacy organization
👼 Chicago Needs More Angels
If we want more breakout startups here, we need more early believers.
One of Chicago’s biggest gaps is deal access. Strong founders are building, but many potential angels sit on the sidelines because they lack access, context, or community.
That’s why I recommend Angel Squad, a global community of 2,000+ angel investors across 50+ countries built by Hustle Fund. I started my investing career there before moving into VC full time. It gave me real deal flow and a network to learn alongside.

Angel Squad provides vetted startup opportunities, events, and a community of investors.
The Chicago Angel Squad group meets quarterly, bringing together local operators and investors who want to back the next generation of founders.
📅 Who’s Hosting This Week
🚙 Waymo Arrives in Chicago
Since December, I’ve been tracking Waymo’s expansion to Chicago.
As of last week, they’re finally here.
Waymo is in Chicago training and collecting geographic data with human drivers as they lay the groundwork for broader deployment.
I’ve ridden Waymo in four cities, and I can confidently say this is a big win for Chicago. I spoke with Fox 32 about why Waymo coming to Chicago is such great news for our city:


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