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This as-told-to story is based on a conversation with GumGum Advertising CEO Phil Schraeder, who’s had a successful side hustle appearing as a contestant on game shows. The piece has been edited for length and clarity.
I’m originally from a small town outside of Chicago. My brother, sister and I were on the swim team in the summers, which meant early 6 a.m. mornings. This was back in the ’80s, where after swim practice, you’d go outside and play with your friends until dark, but in the mornings, no one else was awake. So, when we got home from swim practice around 7:30 a.m., my mom would make us breakfast and put on the TV — and my siblings and I would watch game shows.
I became fixated on those game shows, ones like The Price Is Right and Sale of the Century, and I’d play them with my siblings. I’m super competitive. I love trivia and winning prizes.
Fast forward to after I graduated from college: I worked in Chicago for a short time before deciding that I needed to find myself. I wanted to come out of the closet. I felt very held back from my authentic self. I wanted a change, so I moved with a friend to Los Angeles.
When I arrived, all I had was my car and what I could fit inside of it. I had no job, and I was in credit card debt. I needed to figure out a way to earn money. Luckily, I’ve always been focused on accounting and finance. My background is in business. So, I wasn’t worried about being able to find a job, but I still needed a way to make ends meet in the short term.
That’s when I started a fun and unique side hustle: competing on game shows. I ended up going on The Price Is Right with Bob Barker — and won. I walked away with $900 in cash, an amusement park popcorn cart and a grandfather clock. I was like, Wow, this is incredible. Not only did I love the experience, but I was also living out my childhood dream. I also loved knowing that my family was able to enjoy watching me do it.
Even as I progressed in my finance career, ultimately becoming a VP, I continued with the side hustle and kept a pulse on game show opportunities. Because Los Angeles is the entertainment capital of the world, a lot of first-time game shows have their start there, and they look for contestants locally. So, it’s not that competitive to apply; it’s not a nationwide search.
When I heard about the new show Are You Smarter Than a 5th Grader?, I knew I wanted to apply. And, being a 29-year-old finance and business accounting professional from Chicago, I provided an opportunity for them to try out a contestant who wasn’t in the entertainment industry. Still, it was a long audition process. But I was invited on the show and given about 10 days to prepare.
I wasn’t going to squander the chance. I went to the kids’ homeschool store, and I bought all the third, fourth and fifth-grade books. I bought world geography. I bought measurements. I bought flashcards of the presidents. Every day after my life partner Wes and I woke up, I would study, then go to work. On my lunch break, I would study more. Later in the evenings at home, I’d study until I was falling asleep on the couch.
I ended up winning $175,000 on the show. It gave me a lot of financial freedom.
This side hustle provided other exciting chances to make money over the years. I also appeared on the Dick Clark Pyramid Show, where I won $22,500. I literally took the day off work, called my brother after I won and said, “Oh, that was a good day of work.”
But this sort of side hustle comes with some limitations, too. You can only go on so many game shows over the course of 10 years. Now, if the right opportunity presented itself, I’d consider taking it. I still love game shows and appreciate that they helped set me up financially, but at this point in my life, I’m in a different situation, so if I were to appear on one and win, I’d likely donate the money.
My game show side hustle definitely helped shape me as a business leader.
In the beginning, I was afraid that I might not be taken seriously as a seasoned executive business professional in finance because I enjoyed competing on game shows. But those were my own ideas about societal expectations and being boxed in, and it actually helped me realize that as a CEO and leader myself, I don’t want anyone to feel that their interests or side hustles negatively influence how they’re perceived professionally. We want to celebrate those interests and side hustles; we want to encourage them.
At GumGum, we’re in 20 countries and have over 500 people, so I’ve implemented what I call “starting classes”: whoever started in Q1 of this year would be in the Q1 2025 starting class. And I ask them a lot of questions. What are some people’s side hustles? What are they interested in? It’s amazing to watch everyone light up. There are DJs, macrame crafters, influencers and opera singers. Then, I think about how we can translate those passions into our culture and encourage and support each other in the community.
Related: How to Balance a Full-Time Job With a Side Hustle
From my experience on Are You Smarter Than a 5th Grader? in particular, I learned the value of listening to yourself and following that instinct. I was in a situation where I was unsure of the answer and had to decide if I wanted to risk it all and go with the kid’s answer. If the kid’s answer was correct, I could have won $300,000, but if it were wrong, I would have dropped down to $25,000. Since the kid wasn’t certain about the answer, I stuck with my own and kept the $175,000.
As it turned out, the kid’s answer was right, so I would have won $300,000. But it was still an important lesson in listening to myself — because although it would have felt great to win $300,000, it would have felt far worse to lose $150,000. In the end, I was completely fine with not winning more in order to protect what I already had. You need to stay true to what works for you and what you are comfortable with. Don’t think about what others might have or do, and then compare yourself.
My game show side hustle also taught me a lot about my personal motivations — and how those values can translate to leadership.
On Are You Smarter Than 5th Grader?, I received a surprise video message from my mom, who is an educator and my fifth-grade teacher. I get emotional on the show because my mom’s wishing me good luck. That moment made me realize that, yes, this is super fun, but whatever this is, it’s nothing compared to how lucky I am with the other aspects of my life. It reaffirmed what really matters.
When it comes to business, the most successful leaders are going to be the ones who can go very deep in humanizing us and themselves. I try to stay away from encouraging leaders to be “authentic” because the opposite of that is “inauthentic,” and I don’t think people try to show up inauthentically. They’re just trying to be more transparent.
So that’s my one big push, especially as it relates to the advertising industry: If you’re a leader in this field, the ultimate goal is connecting with someone deeply on an emotional level or a needs level. The best leaders need to show up prepared to do that every day.
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