Will Caldwell is CEO of Dizzle.

Describe what you do in one sentence: “I email a lot.”

Age: 23

Degree, school: Bachelor’s and master’s in accounting from the University of San Diego

Location: San Diego, California

Social media: Facebook, LinkedIn, Twitter

What’s your favorite activity outside of work and why?

I love to kiteboard. I have been kiteboarding since I was 14, and the sport has enabled me to travel the world, appear in a Nissan commercial and meet amazing people from all walks of life. The rush you get from flying 30 feet over the water keeps the adrenaline flowing and my passion for the sport. I have found that same passion as an entrepreneur, and that is why I knew entrepreneurship was the path for me.


What’s your favorite classic piece of literature and why?

My favorite classic is “Hatchet” by Gary Paulsen. The book is about survival, and as an entrepreneur, running a startup in the simplest form is about survival. Much of what the main character, Brian, went through stranded in the woods correlates directly into the life of an entrepreneur.

Are you the first entrepreneur in your family?

Both of my parents are entrepreneurs. My dad is a fine artist, and my mom is a real estate agent. Both roles are incredibly hard to succeed at and require a vast skill set to excel in. Their influence has had a profound influence on my work ethic and drive.

Why’d you decide to start your company?

The concept behind Dizzle started while I was a junior in college. I was learning how to build mobile apps, and after building my first mobile app that eventually failed, my mom approached me asking me to build an app for her real estate business. Once I finished building her app that incorporate a trusted vendor list, other agents asked me if I could do the same for their business, which set in motion the concept behind delivering high-quality, individually branded mobile apps for real estate agents at an affordable price.

Describe a time when you felt particularly insecure about the future of your company. How did you bounce back?

During my master’s degree, I was at a crossroads about pursuing Dizzle full time. To make my dream a reality, I needed to find an investor or an alternative way to make a living. It was just not feasible at the time to bootstrap this business to profitability. I then reached out to San Diego serial entrepreneur James Brennan (also my girlfriend’s boss) on LinkedIn, thinking this guy cannot say no to a meeting with me. In honesty, I was just looking to pick his brain as a fellow entrepreneur and learn how to kickstart my business.

Turned out, Brennan used to be a successful mortgage broker and completely understood the value proposition my app was delivering. Fast-forward a few months, Brennan joined me as my co-founder and invested $250,000 to get Dizzle to the next level.

What would you describe as your company’s biggest victory since you joined it?

In December 2014, we finalized a partnership with the San Diego Association of Realtors to provide 100 free apps to their members. It has been our biggest deal yet since launching in July 2014, and as a San Diego company, we are proud to partner with the largest real estate organization in the county.

What’s been the biggest obstacle your business has encountered, and how have you dealt with it?

Recruiting technical talent has been difficult, as the demand for top engineers far outstrips the supply. As a young entrepreneur, it can be daunting to recruit and find these engineers knowing they have multiple offers from Apple, Facebook and Google. It really has come down to surrounding Dizzle with the right people and executing on what you set out to do. I have fortunately found great mentors who have played a tremendous role in putting myself and Dizzle in a position to recruit some of the best engineers in the business.

What puzzles you most about the industry?

The lack of performance-based marketing and analytics in the industry puzzles me the most. The industry spends close to $12 billion a year on marketing, and yet most agents cannot give you an ROI (return on investment) on their marketing spend. Transparency will be the future of real estate marketing as it builds greater client trust.

What is the most important lesson you’ve learned about building a business?

Surrounding yourself with the right team and people is by far the most important lesson I have learned. Anyone can have a great idea, but it takes an even better team to execute on that idea to make it a success.

What’s the most overrated real estate technology?

IDX is the most overrated real estate technology. We talk with real estate agents on a daily basis, and we rarely hear that consumers actively search on their site. Real estate data is everywhere, and consumer behavior is so prone to searching for homes on large Internet portals that changing this behavior becomes less and less likely every day.

How will the role of the real estate agent change over the next five years?

I believe the real estate agent will come to embrace the term “real estate professional.” Successful agents are more than someone who helps you find a house and negotiate a transaction. They become the go-to person for everything embodying the term “local expert.” As technology enhances the homebuying process, agents will need to expand their skill set into homeownership. Consumers will continue to demand a concierge level of service, and expanding an agent’s know-how falls in line with this macro trend.

What motivates you more: power or money?

Power. As a startup CEO, you need to be in position to leverage your strengths in order to get the job done. Convincing people to believe your vision is a full-time job, and at some point you need to have the power to put that idea in motion.

What is your biggest professional fear?

Running out of cash. Cash flow is everything for a business, and no matter what business you are in, you need cash to keep the lights on.

Whom do you respect most in the industry?

Ed Krafchow, chairman of the board at Mason-McDuffie Real Estate. When I first met Ed, I was blown away at his ability to break down the industry and analyze upcoming trends. He has been in the industry a long time and has seen the industry evolve into what it is today. He is one of those people who just “gets it.”

Would you like to participate in our leader profile series? Email amber@inman.com.

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