Aaron Rosenthal – Co-Founder, E-File.com

Aaron Rosenthal is director of marketing and founder of E-file.com. In 2016, E-file.com along with another of Aaron’s businesses, were ranked by the Jacksonville Business Journal as two of the top fifty fastest-growing companies in North Florida. In 2017, E-file.com was ranked as the 79th fastest-growing company in the country by Inc. Magazine.

How did the concept for E-file.com come about?
Another business of mine focused on lead generation in a few B-to-C verticals. One of them was tax preparation. The companies buying my leads were only interested in them from January 15-April 15. I had customers looking for tax preparation outside of these dates. Rather than look for someone else to sell those leads to, I started E-file.com.

How was the first year in business?
Even though I had some experience in the space from my lead generation background, I treated year one like a big beta test. Since the company was self-funded, we made lots of small “test” ad buys – when something worked then, I would push additional budget to that source. When something didn’t work, I would cut it, learn from it, and move on.

What was your marketing strategy?
E-file.com competes against tax software providers that spend hundreds of millions of dollars on branding and advertising. Going head-to-head is nearly impossible. We decided the best way for us to complete was by focusing on the simplicity of our product and also making sure we were priced extremely competitively. We utilized lots of coupons and discounts to help achieve this.

How fast did the company grow during the first few years?
In 2017, according to Inc. Magazine, we were the 79th fastest-growing private company in the US. By their calculation, we had a growth rate of 4,641%.

How do you define success?
Setting a goal and meeting it without compromising.

What is the key to success?
I like setting milestones that serve as checkpoints on the way to my goal. I expect to modify and revise the milestones periodically along the way to reach my goal. While I don’t mind changing milestones, I don’t like changing my goals. Once I set a goal, I know that it is where I am going and I just have to find the best way for me to get there.

What is the greatest lesson you’ve ever learned?
I sold (technically, it was a merger) my first business for stock in the acquiring company. The purchasing company made loads of verbal promises, but at the end of the day, most of them fell flat. These promises were the reason the deal looked so attractive, and the reason I was willing to walk away with stock rather than cash. I learned two things from this: 1) never rely on “verbal promises,” get everything in writing, and 2) when accepting stock in a private company, always understand the plan for getting your money back out.

What are some quotes that you live by?
I like to think that I treat those working for me, partners, customers, etc. fairly. I don’t ever want to be a business that mistreats someone for the sake of making a profit. So I guess the quote I try to live by is somewhere between the Golden Rule and Dr. Seuss’ quote, “A person’s a person, no matter how small.”

What are some of your favorite books?
I own two businesses and have three children, so I don’t get a lot of leisure time for reading, but I will say the The 4-Hour Workweek by Tim Ferriss sits on my shelf and is one of my favorites. Now, this is less about the content of the book and more about my story in conjunction to it. If you’re not familiar with the premise, Tim talks about working just four hours a week and the lifestyle behind it. Prior to the book, Tim was doing this with his own business where he sold a dietary supplement online. In order to help facilitate the business and work minimal hours, Tim out-sourced different components of the business to various companies. He had turned over the marketing and a lot of web development to the agency I was working for at the time. For years, I handled most of the online marketing/advertising for this business. When Tim talked about the book he was writing, I remember feeling like “Why am I growing someone else’s business? I should be out focused on my own.” This helped propel me into being a full-time entrepreneur and thus remains one of my favorite books.

Tell me about one of the toughest days you’ve had as an entrepreneur.
Last year, I made a decision to move away from a company who I partnered with to help provide E-file.com’s tax software. This company had been a very good partner over the years, and this relationship had been in place since E-file.com was first launched. With that said, I felt if E-file.com was going to keep growing, I needed to move on. The unnerving part of the decision was, I had just 60 days before the upcoming tax season. This left an extremely little margin for error, and if things did not go right, E-file.com could be left down for the entire tax season and it could jeopardize the business. The days working up to this decision were some of the most difficult I have faced, but once the decision was made, I did not allow myself to look back.

When faced with adversity, what pushes you to keep moving forward?
Today, my wife and kids provide me with all the motivation I need to work through any adversity. Before I had a family of my own, I liked to use everyone/everything that made me feel like I couldn’t do something. Memories of being told “You can’t do that” tend to stay with me, so I’d use them. I would ball up those feelings from anyone who ever told me this and then use that to help drive me whenever I needed an extra push.

What advice would you give to young entrepreneurs?
Two pieces of advice I would extend to young entrepreneurs are: 1) don’t wait for the perfect time, because you’ll be waiting forever. With that said, it is okay to hedge your bet. I built my first business while I was still working full-time. 2) Also, you’ll never work harder to make something succeed than when it’s your money on the line. Every one of my businesses started out self-funded. I rolled profits back into the businesses to help them grow and did not even consider outside investment before I had already built a viable business.



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Interviews are conducted for research purposes by author Jason Navallo for his upcoming book, Underdog.

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