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Insights · Article

Kevin Winters of CompanyMileage talks about financing his first company with 13 credit cards and having to paint their first CompanyMileage office themselves

By the Venturity Team July 2021 3 min read

Why did you start the business, what was the catalyzing event?

In 2006, I started a company called OffSiteCIO. But, by the summer of 2008, two things had changed. OffSiteCIO was struggling, and fuel prices skyrocketed. I had also made an investment into a pool business, Sparkle Pool, and they were scrambling to manage the rising fuel costs with their fleet. I helped introduce a bonus program that rewarded employees for using less gasoline. I realized that employees who were reimbursed for mileage could have easily inflated their reimbursement costs to receive 58 cents per mile. These two events led to my inspiration for CompanyMileage, which I quickly developed and launched in 2009.

How did you find your first customer?

It took a year to design and build the product before we began marketing it to traditional businesses in Dallas. We were spending thousands a month on direct mail advertisements and Google Adwords, but the end result was very few leads and even less customers. It wasn’t sustainable, so I stopped everything and began analyzing the data of our first few clients. We worked with a D&B lead generation company and reverse looked up the SIC codes for each of the new clients. I realized we had five unique industries that found us and began only targeting those groups. Today, we have over 100,00 users in those five industries.

Describe your first office/location.

The first offices for CompanyMileage were inexpensive. Since customers did not visit our offices, we took the space as it came. In fact, we painted our own offices.

What’s the most creative thing you did to get your business started, or kept it going through a tough time?

I was 25 when I started my first company, before CompanyMileage. I wasn’t married, and I didn’t have any kids. I needed startup funds, so I applied for 13 credit cards and kept a Lotus spreadsheet to track balances and available credit. When I got married later, my wife was a bit concerned when a credit card bill arrived just about every day.

I self-funded CompanyMileage and brought on two minority partners on sweat equity. It saved me from needing additional capital and also provided talent that I could never have afforded early on.

What’s something quirky or superstitious you do as CEO?

This is very nerdy. As a CPA, I have our financials completed on the first day of each month. 

What was your last job working for someone else? What was your favorite day job?

I worked for Sunshine Mining and Affiliated Computer Services. A little less than a year into my role at Sunshine Mining, the controller left, and the company was experiencing bankruptcy. I remember when the CFO approached me and asked if I had ever written a 10-Q before. My reply was, “I’ve read one” and he said, “good enough.” Not many NYSE companies had their 10-Qs created by a 23-year-old.

Leading the team at CompanyMileage has been the most enjoyable work I’ve ever done.

Where did you come up with the name for your company?

CompanyMileage isn’t the most creative names. I look for names that are self-explanatory. Being a CPA, creativity isn’t my background.

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