I Didn’t Listen To My Boss. Here’s The Crazy Thing That Happened.

We’re All CEOs Here | A Gravity Payments Series (Part Ten)

In early 2014, I was hired on as the second member of Gravity’s Marketing team. Coming from a traditional company back in Minneapolis, it was strange to me how everyone operated at Gravity. Many of my peers around me were moving fast and getting things done in a way that was efficient and hugely beneficial to the company. I wanted to be part of that.

I was so fascinated by this curious culture. There was no hierarchy, no budgets, no permission needing to be asked, no hand holding, and complete and full autonomy. We were all the CEOs here.

Growing up in a small town in rural Minnesota, I was deeply inspired by Gravity’s mission – to help the little guy. I believed in it so much, I wanted to shout it from the rooftops. I wanted everyone to know how great Gravity was, so I was constantly trying to find ways to add value.

I had some free time during lunch one day and started looking up different awards I could apply Gravity for. The company was so different and unique that it’d be an obvious way to get our name out there. I stumbled upon Entrepreneur Magazine’s annual Entrepreneur of the Year Award. While looking through the criteria for applying, each bullet point was everything Gravity and our CEO, Dan Price, stood for. I knew I had to apply him for the award.

Dan was young and completely changing the game in credit card processing. He didn’t want to make “screw you” money and he cared deeply about our clients and making sure our team was as successful as possible. And he never asked for anything in return. So, I submitted an application with hopeful optimism, and waited for the response. I got an email the next week saying Dan had been selected as one of the top ten finalists. A special committee would be narrowing it down to the top five based on an essay. I wrote up an essay about why I thought Dan was deserving of the award, submitted it, and patiently waited for another email.

Several weeks later, Entrepreneur emailed me saying Dan had been selected as one of the top five finalists. I was surprised, but not fully shocked. Gravity and Dan were just doing the right thing for small business owners, so it didn’t blow my mind that others saw that, too. Then I read the sentence in the email saying in less than five business days, we had to create a one minute video. This video would be used in an online voting contest.

I told my boss in order to move forward, we needed to turn around a video…and fast. We had limited resources, capability, or experience on the Marketing team to accomplish even a halfway decent video. But, I was determined.

I knew of someone on our Deployment Team named Wyatt who could edit videos. So, I walked over to Wyatt’s desk and casually asked if he’d be able to help. I warned him of the timeline and he said he could make it work. Success!

I approached my boss again and told him my plan. He said he’d connect with Dan.

The next day, they both told me they didn’t think we should pursue the award. They thought it would take too much time and that we’d lose focus.

I pushed back.

There was no way I was going to let this opportunity slip away. I replied, “It won’t take that much time. I won’t let it get in the way of anything else we’re doing. And even if we don’t win, at least we’ll have a video we can use on the website.”

There was silence.

“How are you even going to get this done?” they asked.

“I asked Wyatt in Deployment if he’d help. He makes videos on the side and he said he’d be able to get it done in our timeframe.”

There was even more resistance, but finally they caved ending the conversation with a “fine”.

It was now up to me to make sure this was a success. So, we created an outline of exactly what we wanted the video to communicate, came up with interview questions for Dan, and planned out B-Roll footage.

We sat Dan down on a couch a few days before the video was due.

“What should I say?” he asked.

I simply said, “Tell your story.”

Twenty minutes later, the interview was done. Wyatt got the video edited and sent off to Entrepreneur by their deadline, while still working his full-time job.

The video was finally pushed live on Entrepreneur’s website for public voting. When I saw who we were up against, my stomach dropped. One of the entrepreneur’s was the CEO of Imgur. I thought, “There is no way we’re going to beat that guy. They get millions and millions of views to their website every single day.”

I clicked out of the online voting website heartbroken, but at least happy we had made it into the top five. That would give Gravity a little bit of a marketing boost.

Then something crazy happened. I came back the next day and we had almost ten times the amount of views than any of the other finalists. By the end of the voting period, we had received more views than all of the other videos combined. I thought we might have a shot, but it was still up to a special committee to determine who would get the coveted title.

Several weeks later, I got an email in the middle of the night. The first word?

CONGRATULATIONS!

I quickly skimmed through the rest of the email not believing what I was reading.

….winner…..Entrepreneur of the Year….Dan Price.

I shot up in bed, reread the email more thoroughly, and dropped my phone.

HOLY CRAP. DAN JUST WON.

I immediately sent out an email to my boss, Wyatt, and Dan. Then fell back asleep. I mean, it was 3:02 AM.

The rest was history.

A few months later, Dan sent Ryan and me a text with picture of him on the cover of Entrepreneur Magazine. We were floored. We were excited about the win, but never imagined he’d be on the cover.

Over the course of the following months, the magazine cover provided Gravity with a level of exposure we never imagined.

About a year later, my boss told me that though he was resistant to submitting a video for the award, he thought it’d teach me a lesson about failure and prioritizing my time. He ended with, “I’m glad you didn’t listen to me.”

Sometimes you have to stick to your guns. Do the thing you know in your heart and gut is right, even when there’s resistance. It can be scary going against those at the “top”, but if you are 100 percent passionate about what you’re doing, do it with all your heart.

I firmly believe in everything Gravity stands for, so it wasn’t a stretch for me to think others would dig our mission and vision, too. And to think, all of that never would have happened had I listened to the CEO of the company instead of the CEO of myself.


Hayley is on the Marketing team at Gravity Payments. For more stories from our “We’re All CEOs Here” series, check it out here.

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