I am relentless about being a slave to only one master; and that means being in the moment all the time about the company you are running. You must live it.


Jason Kulpa is the driving force behind Underground Elephant. He architects business, technology and product road maps and manages high level strategic partnerships. He brings 13 years of web traffic monetization experience, spanning multiple product and industry channels. Underground Elephant has been highlighted on the Inc. 5000 list of Fastest Growing Private Companies for four consecutive years. In 2012 and 2013, the National Association of Business Resources recognized UE as one of the Nation’s Best & Brightest Companies. UE is also a two-time winner of the San Diego Business Journal’s Best Places to Work in San Diego.

In 2014, the American Business Awards honored UE with a Gold Stevie for its corporate social responsibility initiative, “Serving those who serve our Community.” Underground Elephant has also been a long standing supporter of the San Diego Police Foundation. The company has provided donations to the SDPF in order to fund the adoption of two police dogs for the SDPD K-9 Unit.

Jason is a two-time winner of the Most Admired CEO Award by the San Diego Business Journal in 2010 and 2014, and is an Ernst and Young Entrepreneur of the Year semifinalist. He is also a member of the Young President’s Organization, and the Young Entrepreneur Council. Jason is also dedicated to the San Diego community, and has worked to establish San Diego as a technology hub by planting his company’s headquarters downtown. Over the the course of three years, he worked with BASILE Studio to design an innovative office space in one of East Village’s oldest warehouses. The space recently won an Orchid Award for Interior Design from the San Diego Architectural Foundation. Jason attended Arizona State University and Harvard Business School in Cambridge, Massachusetts.

Where did the idea for Underground Elephant come from?

The idea for Underground Elephant came about while sailing off the island of Lanai – I manifested the entire process from start to exit. It took about an hour for it to make sense, but it was then it all happened… everything.

What does your typical day look like and how do you make it productive?

The day starts the night before when I prep from 8pm – 10pm. I use an organization application and make a list of important items. Then I review my calendar and start visualizing the next day. At 6am when I wake up, I make a cup of coffee and check my phone for emails. From about then until 7am I am on my home computer, then I drive to work where I use that time for calls. I get to work at about 7:30am and then I am in meetings or working through ideas with managers. My goal is to be more and more people-centric, discovering people-challenges before they happen. Lunch is at my desk, and rarely do I leave the campus for a meeting or event. At the end of the day I head to the gym, and then home for family time. It’s important that I bring the same passion and enthusiasm home as I do to work each morning. So I make an effort to have energy, and be creative when pulling into the driveway. I might be a pirate, or co-explorer with my three-year-old boy and it will take a clear head. That is until 8pm, when it all starts again.

How do you bring ideas to life?

Over the last few years I have changed my approach to executing on ideas. Before I would react when they occurred, often sending an ad hoc email. Now I take a more structured and restrained approach by forcing myself to wait. That gives whatever concept I am hatching time to cook often sitting somewhere quiet to think on it. If it’s complicated and later in the evening, bourbon helps.

What’s one trend that excites you?

Amazon’s entrance into the food services business excites me, and grocery stores will go the way of the shopping mall. Enjoy your demise, chilly frozen-food isle.

What is one habit of yours that makes you more productive as an entrepreneur?

Prep is everything, and the secret to life. There was a reason you got homework as a kid, so why stop because your an adult? Take twenty minutes an evening to think about what you need to do the next day, and you will be surprised how much it pays off.

What advice would you give your younger self?

I would have taken better care of my body and mind as a younger man. Fitness and diet only became part of my routine in the last five years, and makes things harder than they have to be today. Start running, and thinking about what you put in your body. Both will make you better later.

Tell us something that’s true that almost nobody agrees with you on?

I don’t believe in luck, but rather you get what you think you deserve. That is more important than thinking good things will happen. They won’t unless you believe that they will, which means more certainty.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I am relentless about being a slave to only one master; and that means being in the moment all the time about the company you are running. You must live it.

What is one strategy that has helped you grow your business?

Avoid looking at things with a biased lense based on data that might not be totally accurate. Sometimes things can be both right and wrong at the same time limiting opportunities. Challenge all your assumptions at least once a year to keep growing.

What is one failure you had as an entrepreneur, and how did you overcome it?

I’m embarrassed to say it but I didn’t pay attention to the balance sheet, and focused too much on profit and loss statements. This led to a shortage of cash, and pressure on the business even though the company was making money. My advice is to own all the numbers, not just the sales and marketing.

What is one business idea that you’re willing to give away to our readers?

Ketchup and Mustard in the same bottle. I am sure this hasn’t been invented, and it would save a lot of time at baseball games.

What is the best $100 you recently spent?

I gave a tip to the manager at a restaurant who got our ten-person business group a great table on a busy night without a reservation. We had a wonderful evening and were able to advance the business conversation while the managers and staff made us comfortable.

What is one piece of software or a web service that helps you be productive?

Evernote – I use it a few times a day to keep organized and to prep.

What is the one book that you recommend our community should read and why?

48 laws of Power by Robert Greene is a powerful look at emotional intelligence and can be helpful managing.

What is your favorite quote?

“If you strike a king, make sure you kill him.” This Emerson quote reminds me that you must go all-in on whatever you do, and being committed is important. Otherwise you leave yourself open to exposure especially from powerful adversaries.


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