The most frustrating purchase of his life

In 2005, Judd thought he was on the career path he’d be on forever. With a CS degree and a strong interest in UX design, he landed at a digital agency as a product designer, back when websites still felt new and apps didn’t exist.

When the agency brought IKEA on as a client, Judd and his team launched a chatbot named Ask Anna, one of the earliest examples of conversational UI at scale. Then the agency won Target’s business, and Judd got to help them break away from Amazon’s infrastructure and rebuild their e-commerce platform from the ground up. In 2009, he was promoted to a manager role and moved from New York to LA to lead the agency’s West Coast presence.

Two years later, in a committed relationship with his future wife, and ready to put down roots, he decided it was time to buy a house.

What should have been a meaningful milestone turned into a mess. The process of working with brokers felt unnecessary, opaque, and full of friction. In a competitive market, Judd and his wife were using every tactic they could think of to find their new home. They were constantly searching Zillow, Trulia, Redfin, and even Craigslist, cross-referencing listings, and texting them to each other. One night, he spotted a new listing, toured it the next morning, and tried to make an offer. But his broker insisted Judd’s wife see it first. Judd remembers thinking, “What do I even need this person for?”

Judd realized that the homebuying process was stuck in the past, where everyone was pushed to use a traditional full-service broker charging a standard fee, with no better options.

The experience was so infuriating, Judd became consumed with finding a better solution. He was even open to leaving his steady agency job to work on an idea full time. “It felt like a pretty risk-averse decision,” he says. “Worst case, I could go back to the thing I already knew how to do.”

Building the foundation for Open Listings

Over the next few months, he reached out to two close friends with engineering backgrounds, including Alex Farrill, who would later become his co-founder at Deferred, too. Alex had also recently bought a house and was appalled at how painful the process was. At first, it was casual conversations. What if buyers could search, tour, and make offers entirely online? What if brokers only stepped in when needed, and buyers kept more of their money in the process? The more they talked, the more the idea took shape, until both friends agreed to join Judd. They worked nights and weekends, doing what they could around their full-time jobs.

Even though they’d felt the pain points firsthand, they wanted to validate that others experienced them too. They interviewed buyers, mapped the buying journey from start to finish, and surfaced the friction points that came up over and over. Out of that work came their hypothesis: people wanted a self-guided, digital-first experience, with expert support on demand, and a lower buyer agent commission. They started building and soon named it Open Listings.

Still, they weren’t sure how big it could get. “If we could sell a few homes, we could scrape by,” Judd says. “Either it was going to go just okay and we’d be shitty real estate agents, or it was going to scale.”

The Open Listings team started looking around for resources that would help guide them as first-time founders. They landed on YC as a force multiplier, offering capital, speed, strategic guidance, and a vibrant peer network.

Getting into the W15 batch gave them more than just funding, it gave them a framework for how to operate. “YC taught us how to build a company,” Judd says. “To understand what really matters, focus week to week, and nothing else.”

Joining Opendoor over Series B

By 2018, they’d built a strong foundation. Open Listings had expanded to five states, transacted $2B in residential real estate, raised multiple rounds of capital, and grown to a team of 45. The product was working, customers loved it, and the team was hitting its stride.

They were considering a Series B raise when another opportunity popped up in Judd’s inbox. It was a message from Eric Wu, a fellow YC founder Judd had met during his batch, who had since gone on to start Opendoor with Keith Rabois and two others. When Opendoor, a real estate platform for buying and selling homes, IPO’d in 2020, it’s market cap was $18B.

Judd and Eric had stayed in touch over the years, comparing notes since their companies were in the same space. Opendoor focused entirely on the seller side of the market, making it faster, simpler, and more predictable to sell a home without a real estate agent, and now it was looking to shore up the buyer side of its offerings. Eric floated the idea of having the Open Listings team join Opendoor, rather than going out to raise a Series B.

Judd and his co-founders saw that combining forces would give them access to a massive user base and the resources to expand their impact. It would also allow Judd to stay focused on what he loves doing: building. Raising a Series B would mean stepping into an executive role he was much less excited about. “Early on, I realized I don’t like managing executives and looking at this growth model and squinting to make sure our CAC is good in these channels,” Judd says.

In 2018, Open Listings was acquired by Opendoor. Judd and his team went on to run buyer operations inside the company, heading up reselling homes purchased by Opendoor, capturing buyer-side commissions, and helping improve the company’s unit margins. They also led a mortgage product to increase attach rates and deepen customer value. But after three years at Opendoor, Judd was missing the startup life.

Leaving Opendoor to fight foreclosures

After COVID, millions of Americans entered mortgage forbearance, a temporary pause on payments that helped them avoid default. But many people didn’t understand the terms, thinking they’d been granted a pass on their payments, when really the debt was still there, accumulating.

By 2021, these homeowners were back on their feet, employment had rebounded, and their homes had appreciated. But their credit had taken a hit, which locked them out of refinancing or restructuring options. They were stuck, sitting on equity they couldn’t touch and facing foreclosures.

Judd saw an opportunity to build something that could provide a way out. He left Opendoor and teamed up with his pal, Aaron LaRue, who had been a product leader at one of Open Listings’ main mortgage partners, Clara Lending. Judd and Aaron had worked together to create a unified pre-approval and touring experience. The two started scoping out a shared equity model designed to keep people in their homes. The product, which they called Balance Homes, allowed a financial partner to buy 80% of the home while the homeowner kept 20% and continued living there. They could buy back the home at any time. “It was like turning your home into a rental that the occupants co-owned,” Judd says. “They remained the homeowner in every other sense.”

Balance Homes helped around 80 families avoid foreclosure. About a quarter bought their homes back within two years. “It was a win, win, win,” Judd says. “For the families, for the business, and for the portfolio.”

But rising interest rates pushed their cost of capital from 8% into the mid-teens. The model couldn’t scale, and in 2023, they sold the portfolio to EasyKnock.

To Judd, Balance Homes was a chance to build something meaningful, but also a lesson in the limits of good intentions when the economics don’t work. The experience made something else clear: knowing when to walk away can be just as important as knowing when to start.

Another firsthand frustration becomes Deferred

Judd had walked away from Balance Homes, but he wasn’t done with building companies.

The idea for his third company came while he was going through a 1031 exchange, a tax provision that lets real estate investors defer capital gains by reinvesting the proceeds into new property. The process was archaic, and a deja vu moment from when Judd bought his first house. “It’s the sleepiest file cabinet business you’ve ever imagined,” Judd says. “We looked at it and we were like, this is actually just a fintech business.”

Two problems stood out immediately. First, a 1031 exchange required manually filling out stacks of paperwork, collecting signatures from multiple parties, and chasing down the same documents again and again. Most of it happened over email or even fax, with little transparency for clients about the status of their transactions. Judd knew automation would speed up and simplify most of it. Second, the economics were skewed against the customer. On a typical deal, traditional 1031 intermediaries charged a $1,500 fee but held the customer’s large lump sum for months, earning tens of thousands in interest when a high balance exchange was involved. Deferred’s model eliminates the fee, shares interest on large transactions, and automates the work to make exchange officers far more efficient.

Judd turned to two people he trusted most to help him work on this new idea. By this time, Alex had left Opendoor and was ready to build something from scratch again, and Aaron was also looking for a new challenge after selling Balance Homes. Together, they mapped out the plan with the confidence of founders who’d been through it before. “We just sat down and said, this is an industry where, if we build a unique offering and run these experiments, it will work.”

Learnings as a three time founder

Now on his third company, Judd’s operating style is almost unrecognizable from when he started.

At Open Listings, he could spend hours obsessing over details that, in hindsight, had little impact on the outcome. Now he moves quickly through those decisions, confident in what matters and what’s just noise. “The first time you spend all your time trying to understand things like equity plans,” he says. “The second time, you just say: here’s the spreadsheet. Let’s go.”

Efficiency is the default. Meetings are rare, communication is direct, and tools are simple. “We try to do as little work-about-work as possible,” he says. The cadence follows the same YC playbook he learned years ago: pick the most important thing each week and work on it.

Now, with more experience, he knows how long growth bets take to pay off and acts early to maximize the return. When something shows signs of working, he pushes it to the limits. It’s not about spending freely, but about moving fast when the evidence points to growth.

Judd also works with more balance, structuring his days, working out, and avoiding burnout. “I still work like a maniac,” he says, “But I try to be healthier. It’s more sustainable now.” Part of that sustainability comes from keeping his identity separate from Deferred’s. “With your first company, everything is tied up in it,” he says. “Now, I work just as hard. But I’m not as worried.”

Playing infinite games

Today, Judd has stripped away the noise and stayed focused on the parts of the job that matter most to him. He still stays up late, going back to his design roots to find ways to improve experience and capabilities for customers. “It’s probably a thing I’ve done over and over again for the last 10 years,” he says. “Designing dashboards and tools to help someone do their job better.”

Deferred is still following the roadmap the team created at the beginning, and the work feels sharper and more deliberate than anything he’s built before. The company is growing steadily, fueled by a clear mission and a model that rewards execution over endless reinvention.

Even as Deferred does well, Judd keeps his view beyond this chapter. He works just as hard, but without the pressure of believing everything depends on a single outcome. The lessons from three startups, how to focus, how to execute, how to choose your own version of the job, will carry into whatever comes next. “You realize your career is long. This is only one of many things you’ll build.”