Nathaniel Broughton – Founder of Eligibility.com

I make a short list of things to do in Text Edit, then do them. Then I make another list. It keeps me on task and could not be more simple.

Nathaniel Broughton is the founder of Eligibility.com and PolicyZip, an online insurance agency specializing in life insurance. He previously founded Spread Effect, SuretyBonds.com, LakeRentals.com and Plus1 Marketing. He frequently lectures on entrepreneurship at the University of California-San Diego, and San Diego State University. He lives in La Jolla, California with his young family.

Where did the idea for Eligibility.com come from?

I’d previously worked in a few verticals that were tied to government benefit programs. All of those programs have “eligibility” guidelines. Eligibility.com was a natural choice to build out, and allow us to have plenty of options to find verticals to work for lead generation. When searcher is looking for eligibility answers, they’re early in the process of becoming a customer for any service that goes along with the benefit program.

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

I work out early, hang with my family for breakfast and then bike to the office. I make it productive by sitting in my little corner of the office and working from a simple “to do” list all day.

How do you bring ideas to life?

We have a great core team of people. My partner and I have worked together for 10 years, and the other guys have been here for 5 years. Everything is a team effort.

What’s one trend that really excites you?

I suppose I’m excited that more and more people over the age of 50 are comfortable doing business online and over the phone. The internet is how we connect with potential customers, and the more people search and understand it’s safe to work with a remote company, the better.

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

Inbox zero. No email sits in my inbox for long, without going to a folder or list of actions. I can’t believe people try to navigate hundreds of unread emails.

What was the worst job you ever had and what did you learn from it?

I worked 2 days with Labor Ready in high school. It wasn’t that bad of a job, just manual labor. I learned I want to be the guy hiring the labor. Not the labor itself.

If you were to start again, what would you do differently?

I certainly didn’t appreciate the difficulty of starting a successful business when I was in my twenties. It would be nice to go back to my 21-year-old self and tell him to calm down.

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

I make a short list of things to do in Text Edit, then do them. Then I make another list. It keeps me on task and could not be more simple.

What is one strategy that has helped you grow your business? Please explain how.

We’ve always developed custom software to manage our businesses. Notepads and Excel files, and even off-the-shelf CRMs are limiting. If you want to provide the most efficient service to your customer, and if you want to maximize your chances at profitability, build custom software to manage every aspect of your business.

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

I’ve dumped money into a handful of partnerships and startups that I’m still hoping will return to my bank account. It seems unlikely. I learned not to be impressed by anecdotes that have nothing to do with if a business will be profitable. I also learned to take it slow. Don’t feel pressure to make an investment today under the fear that the opportunity will pass you by.

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

It’s called Driveway Hologram. You put a little hologram device in your existing car and it projects a hologram of a car of your choosing around your car. Want to have a Bentley? Half the fun is letting that thing sit in your driveway for people to see. Now you can!

What is the best $100 you recently spent? What and why?

I spent $2 on a baseball sticker book for my son. That purchase was worth infinitely more than most of the things I’ve spent $100 on lately.

What software and web services do you use? What do you love about them?

I love the core stuff. Gmail. Dropbox. CamScanner+? That’s a unique one, I suppose. Take pictures of documents with your phone and it turns them into PDF’s.

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

I always recommend Jerry Weintraub’s “When I Stop Talking, You’ll Know I’m Dead”. He died last year, unfortunately, but his stories of hustling to the top of the entertainment world as a concert promoter and movie producer are fantastic.

What people have influenced your thinking and might be of interest to others?

From my generation, I like Ryan Holiday. I think my friends Brent Beshore and Gabe Lozano are both thoughtful writers and business people. Google those guys. They’re all thought leaders that will be around for a long time to come.

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