Picture of Carin Oliver
Carin Oliver

How I Became An Accidental Entrepreneur

Approx Reading Time: 1 minute 

I never intended to be an entrepreneur. Although, it’s probably where I was always headed, given that I love helping others and solving complex problems that seem insurmountable. And really, entrepreneurship is not much more than a healthy dose of intellectual curiosity and the ability to be comfortable with discomfort.

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My parents worked the same jobs for decades, and it was inconceivable to them that anyone would leave a reliable job. So, I had limited entrepreneurial models in my life and didn’t have a burning desire to work for myself at the time. 

I was happy working as an account executive at a Beverly Hills entertainment public relations firm. It was in a penthouse on Wilshire Blvd., with a rooftop deck and panoramic views of Los Angeles. Kinda swanky. 

But then, what felt like a once-in-a-lifetime opportunity called. 

A colleague I had previously worked with recommended me to the creators of a dinner theatre concept. We had a great discussion about their project. I was psyched. I ran to the President’s office of the PR firm and excitedly told him about this great new business opportunity. 

He was not impressed, and their budget was literally only $500 under the agency’s monthly retainer requirement. I begged, I pleaded, but he wouldn’t budge. 

Devastated, I started to pick up the phone to call the creators back to tell them that the agency wouldn’t be pitching the business. But then a co-worker distracted me, and thankfully, those five minutes changed the trajectory of my life. It gave me a few minutes to come to the conclusion that I wanted to pitch the business myself. 

I returned to my boss’s office and told him my plan: I wanted to pitch the business, and if I got it, I would resign. 

He laughed in a pissed-off way while throwing a tennis ball at the wall inches from my head. Literally. 

He wasn’t concerned that I would quit because he believed there was no way they would hire me without the weight of the agency behind me. I was pitching against some of the biggest PR firms in Los Angeles for this business. 

My competitive gymnastics training kicked in at that moment. I didn’t care that I would be completely alone, going head-to-head with teams of pros from two publicly traded mega agencies. 

I’d already faced down the Chinese on a 4-inch beam 4 feet off the ground in a packed gymnasium. These were two legendary creators in a cozy Orange County conference room. What could possibly go wrong?

The creators were the late former president of Disneyland, Jack Lindquist, and Jim Garber, a former Vice President of Marketing for the Walt Disney Company. They agreed to let me pitch the business without the support of my employers. 

It was time to get to work. 

But first, I had to tell everyone about my plan—a bad idea. No one was as excited as I was about this incredible opportunity. There were as many objections and ‘why-nots’ as there were people I shared my story with. Everyone cautioned me not to get too excited. 

With each response, my long shot seemed further away, but I was convinced I was the only one with the exact experience they needed to succeed. 

I was a woman obsessed with using my PR skills on their project. I had four days to put together a smokin’ pitch. 

I knew that if I was going to win the business, I would have to adopt an unconventional strategy while maintaining grounded tactics. 

I worked through the nights, hyperventilating for most of it. But I never wavered in my belief that I was the right person for the job. 

The day arrived. I fought traffic down to Orange County and barely arrived in time. It was hot; I was sweating just walking from the car to the building. 

I heard two men laughing in the blessedly air-conditioned office as the elevator doors opened. Everything is going to be okay. I’m feeling calm and confident. 

They welcomed me into the conference room and told me I was the last to pitch. 

Everyone has a different idea of whether being the last or the first pitch gives you better odds of winning the business. Being the last gymnast to compete frequently provides a competitive edge, so I considered this a good sign. I felt as confident as possible while still slightly sweaty, this time from nerva-excitedness. 

I dove right into my pitch. 

It’s going well. We were talking strategy. I’m beyond thrilled to have this high-level conversation with two legends. I’m getting giddy. 

But then disaster strikes. 

About halfway through my pitch, Jack gets up abruptly, thanks me, and leaves. 

My world spins off its axis. 

I’m 5’2”, but I think I shrink to under 5 feet. My chin feels like it’s barely over the conference room table. 

Jim Garber gamely sits through what I imagine must be the worst pitch of his life. I soldier on, but I’m devasted. 

One thing I can tell you with 100% confidence is that when a key stakeholder leaves the pitch, you’re absolutely not going to get the business.  

I decided that Jim Garber was the nicest man on the planet to sit through my horrible presentation.  I wanted to speed it up but couldn’t get my mouth to comply; everything felt like it was moving in slow motion. You know those nightmares where you can’t scream or run? That’s what’s happening to me during the second half of this pitch. 

All the energy had been sucked out of me. I worked through the night on this presentation; the anticipation, the heat, and, of course, Jack walking out have sapped all my brain’s capacity. 

We wrapped up. I thank Jim profusely.

I spent the weekend working out obsessively to distract myself from what was coming on Monday. I must tell my boss (and all my friends) that he was right. I didn’t make the cut. 

Surprisingly, my boss told me to keep my faith. I thank him for being kind as I slink back to my office. 

Three days later, Jim called me, and I’d won the business! I was beyond thrilled and stunned—relieved. When I asked Jack later why he left the pitch, He said he’d heard enough; he had decided to hire me. And besides, he had a tee time. 

Then, it hit me like a ton of bricks. All my emotions around the presentation paled in comparison to realizing that I had just quit my cushy job in a plush office, hobnobbing on red carpets with celebrities. I joined my parents in wondering what the #%ck I had just done. 

But then it dawned on me for the first time that I’m an entrepreneur, and I can decide which clients to take based on passion. For the second time that week, my world shifted. This time, for the better. 

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