November 6, 2015
When Will Caldwell came back from a semester studying abroad he was getting set to enter his junior year at the University of San Diego (USD). There was a slight problem, though: he was freaking out because he was an accounting major and realized he hated accounting. In fact, this was the first step on an entrepreneurial pathway that would take him through a roller coaster of success, failure, and the ultimate founding of the popular real estate platform Dizzle.
He had a friend who was paying close attention to mobile apps just when they were getting popular, in 2011. Caldwell thought that if these other kids could make dynamite apps, he could too. So, he signed up for an online class at Stanford, but he wasn’t trying to learn how to code. Rather, Caldwell was hunting for a developer to help him bring his ideas to life.
Ultimately, the plan worked out well and he ended up connecting with some overseas developers to build out his first app. Long story short, it fell flat on its face. But Caldwell learned some valuable skills about app building that he put in his pocket and took with him to his next project.
“My first app flopped, but through the whole process of learning to build, my mom watched and then said she wanted an app,” says Caldwell. “She’s in realty, and her top competitor had just gotten an app.”
His second project, Dizzle, turned out much better and is still going strong today. However, it’s pivoted a lot. For example, the first iteration Caldwell built for his mom was packed with features, but only had one really meaningful feature that ended up guiding the future for Dizzle: a personal vendor list.
Put yourself in the shoes of a real estate agent for a moment. People are constantly asking for your recommendations for dog walkers, termite inspectors, and all of those services that are 100 percent necessary when buying a new home.
“That was the most popular feature at first, and what I learned is that these vendors love real estate agents because they’re constantly meeting new people and referring new business directly back to them,” says Caldwell. “It’s a goldmine of leads.”
Caldwell ended up taking this early iteration of Dizzle to market and even managed to get paying customers. However, his Achilles heel was that he didn’t know anything about incorporating. It definitely made the transition from full time college student to full time entrepreneur difficult, but Caldwell is the type to fail often, fast, and forward (all good things).
“I had to make this work one way or another,” says Caldwell. “The most important takeaway was the network I built. When we finally went to market with a polished version of the app, we got great responses.”
Another one of the pivots for Dizzle came when one of the big customers decided they wanted to use Dizzle for a different purpose. Effectively, the San Diego Association of Realtors brought forward the idea for an affiliate program where vendors can pay to reach realtors. Caldwell quickly caught onto the strategy behind the idea: these vendors would pay much more to connect with realtors than realtors would pay for software.
“All those things required to get a deal done for any home that’s selling, that’s a huge market,” says Caldwell. “I thought that if we could help vendors meet agents in an efficient way they’d pay a lot of money. My hypothesis has turned out to be very true.”
Finally, everything lined up for Caldwell and he’s been able to run steadily with Dizzle ever since. To date, he’s signed about 200 key companies to the platform, and if he can keep the momentum going his revenue estimates hang around the $500,000 to $1 million per year mark. Caldwell also just locked down the largest Century 21 in the country, in San Francisco.
It’s all too brilliant. In addition to the access vendors get to realtors, the average home owner spends about $14,000 to renovate and personalize their home withing 90 days of buying.
“It’s such a no-brainer for anybody who understands real estate,” says Caldwell. “We’re the company that’s laser focused on the post-sale window when consumers are spending the most money they’ll ever spend on their home on average.’
Caldwell has one of the most Zen philosophies I’ve come across in the industry. Naturally, the San Diego mentality has a little bit to do with it, but he’s also an incredibly accomplished, professional kite surfer in his downtime.
“If the wind is good or the surf is good I don’t want to be tied to a desk. I work a lot, but I don’t have to answer to anyone and if I need to be on the water I can be on the water,” says Caldwell. “Creating a culture and place for others to work like that is cool too. Money is nice but it only goes so far. It’s more about creating a great product.”
It’s that mentality which helped him take second place at the 2014 USD V2 Pitch Competition, and it’s what will continually drive him towards success. I wouldn’t want to be the one to stand in his way further down the road either: he’s the epitome of the move fast and break things mentality. Respect.
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