4 Reasons Every Entrepreneur Should Start Their “Career” at a Proverbial Gas Station

Originally published on Fast Company

It started over a decade ago when I was a 15-year-old microwaving gas station food and endlessly scrubbing diesel off of the concrete slab beneath the avocado green fuel pump. Fast forward a few years and I’d been a dishwasher, a pizza delivery driver, a door-to-door salesmen, a shoe stocker, a clothes folder, a cold caller, a boat cleaner, a lawn mower, a cell phone dealer, and a house painter. Each of these jobs taught me something, but as I get older I realize more and more how much they’ve played a role in who I’ve become and the perspective I carry with me day in and day out.

There are four things in particular about my years in these jobs that I felt groomed me for the entrepreneurial community I’m proud to be a part of today: perspective, empathy, customer service and understanding how to be lead by non-leaders.


Meet scenario one and scenario two. Scenario one is a junior in high school. While all of his friends are hanging out at the grocery store parking lot, (which in high school is considered “a blast”), scenario one finds himself staring at what must be a 13-foot high stack of dirty dishes. Six hours later, hands raw and soggy, scenario one leaves knowing that tomorrow the stack will be just as tall and dirty. At the same time, scenario two is also a junior in high school and is hanging out at the grocery store parking lot with friends.

Fast forward a couple years to college. Scenario one is now 19, a freshman, and after finishing up class heads home to throw on a headset to start making cold calls. For every 100 calls, scenario one normally gets a “yes” which equates to $15, cash in hand. Meanwhile scenario two, also 19 and a freshman in college, is studying at the school’s cafe with some friends. They’re trying to finish quickly so they can head over to one of the dorms for an outdoor movie.

Another three years go by, and scenario one is a college grad working at a coffee shop. $12/hour with tips, not a bad deal. Scenario two, also a year out of college, is taking a year to find himself by traveling through Europe. Pretty awesome.

And finally, we’re at age 25 for both scenario one and scenario two. Coincidentally, they’ve both found themselves at the same company with the same job. Scenario one is thrilled. Why? It’s a salaried position, weekends are free, paid time off and sick days are a part of the package, working remote is fair game, and he is working on things that feel strategic and important. He earned this job and is proud of it. Scenario two, meanwhile, is feeling okay about the position. Sure, there are benefits and weekends, but he’s a smart college grad, of course he has benefits and weekends. And some of the people on the leadership team are really difficult to work with. It’s definitely not the worst job, and actually pays pretty well, but probably won’t be a long-term thing. There must be better opportunities out there, after all this is only his first job.

Perspective is shaped by world view and world view is shaped by history. Both of the histories depicted in the two scenarios above are good. These are not impoverished people, they’re both average in their own right. But scenario one is able to see things in a job that scenario two can’t possibly see. Little things like benefits, weekends and sick days should be appreciated, but if you’ve never experienced anything else than the standard is just different. I’m proud to be a member of the scenario one tribe. To the scenario two’s reading this article, you’re still awesome. Just take a step back, maybe go shadow someone in a job that lacks some of the privileges you’re accustomed to, and appreciate the little things. It might make your pain points feel less significant.

So how does this apply to entrepreneurship? Chris DeVore, founder of Founders Co-Op, says it best: “As every founder knows, building a business is mostly unglamorous work. For every day you get to sign a big deal or earn a glowing writeup in the press there are literally hundreds more full of disappointed customers, disgruntled teammates, paperwork hassles and taking out the trash. Nothing helps you appreciate both the good days and bad as an entrepreneur than having been a cog in someone else’s machine.”

Empathy and Understanding

“Being an employee, especially at a company with low wages/not-so-great benefits, is a wonderful way to build empathy. It’s not just the personal experience, but the connections you build to your coworkers and customers. You have the opportunity to develop relationships with people you are unlikely to meet in the startup and technology worlds and to appreciate their struggles in a way that going straight from college to technology jobs cannot show you,” said Rand Fishkin, co-founder/wizard of Moz.

The Shell Station I worked at was close to an oil refinery, and so at certain times during the day our customers were primarily tradesmen. Hands stained a charred black, they’d come in for a refill on their Big Gulps, (or the Shell equivalent), and a pack of marlboro ultra’s. At first, I was intimidated by the bunch. They were loud and crass, and different from what I was used to. And then one day, everything just sort of changed. There wasn’t a magical moment or anything like that, I just developed an appreciation for them. They worked long hours and often didn’t start their shifts until late at night. Their seemingly crude personalities became endearing, and they paid more attention to me then the customers I would have expected to identify with. Eventually, these were the customers I looked forward to seeing.

This is just one example, but a meaningful one. Not only did I learn about the problems that refinery workers face, (lots of room for innovation there), but I also learned how to communicate with a once-foreign demographic of people. I know that I’m walking the “generalization” line here, but if you’ve been there you understand. Empathy is the ability to walk in someone else’s shoes, and to comprehend their struggles and triumphs as if they were your own. Work at the proverbial gas station and I promise you’ll be able to empathize with a much larger group of people.

Customer Service

People are weird and difficult, and the only way to get past it is to expose yourself to it over and over and over again. Delivering pizzas or knocking on doors to offer “free house-painting estimates” are just a couple of exposure techniques, but in my opinion will better prepare you for the customer development/service aspect of a startup than anything else. For a while you’ll feel like you’re never going to learn to appreciate those whom you don’t understand. And then one day, on your 600th delivery to a person who always answers the door stark naked with a cigarette stuck to their lip, you’ll fall in love with what some would call crazy. We’re all unique, (corny or not), and once you understand that people are always just people, you’ll be able to work with anyone in a whole new way.

As an entrepreneur you better know how to work with and relate to customers. Reading books on customer development and surveying people at the mall aren’t bad, but go work at the proverbial gas station for a month and you’ll see what I mean.


Simply put, some people aren’t built to work at the proverbial gas station. I’m one of those people, and when I hit my early 20’s and found myself at a coffee shop, I decided I was ready to cross over to the other side. I’ve spent the past 5 years since working hard to ensure that I never have to look back. Drive fueled by world view is a force, and can push you to work harder then you ever thought possible.

Fight is something every entrepreneur needs to have, and these jobs bring a whole new meaning to the word.

“The foundations for great work ethic and drive are set early on. In my experience, people who have excelled in fast pace, customer service type roles early in their work history have a set of values that help them excel in their careers later in life. Jobs that require you to work long hours, always have you striving to be more efficient, and force you to keeping customers smiling no matter what set the tracks for great characters of leadership, communication, and of course, hustle,” said Marc Nager, CEO/Co-Founder of UP Global.

Learn to be lead by non-leaders

Earlier in the article, I talked about scenario two and how they had a hard time working with some of the companies leadership. I’ve experienced this at every company I’ve worked for, (post gas station-esque jobs), and find myself laughing almost every time. (I use the word almost with intentionality, there are always exceptions.) In order to be the leader of a funded startup company, you need to be able to impress investors, a wise bunch, enough to write you a check. There’s a board of directors watching your every move. You’re fighting against people with education and more importantly experience. Put in another way, there’s more intentionality around who is selected to be on the leadership team of these companies.

Brad Feld wrote a piece a while back about his first job and how washing potatoes got him fired, where he sums this point up perfectly. “My boss never did anything to create a context in which we were motivated. It wouldn’t have taken much. And, if she had, respect – and motivation – would have followed. At 15, I learned what it was like to be on the receiving end of a boss who had no idea how to create an environment in which the people that worked for her were motivated. I’ve carried that experience, and the resulting insight, to every subsequent thing I’ve been involved in.”

Now You Know

If you’re reading this, whether you relate more with scenario one or scenario two, you’re likely too late-stage to go back to a place where working at the proverbial gas station makes sense. So what are you supposed to walk away with here? Hopefully, you’ll walk away with a little perspective, with a desire to better empathize with those around you, with a yearning to understand your customers beyond the five minute surveys you give them each time you update your product/service, and with a realization that you’re probably luckier than you think to be working with and for those you’re working with and for. The world is a rough and tumble place, even in the context of the first-world-problems we’re discussing here, and it’s important that we all constantly take proactive steps back to actually see what we’re looking at.