I was on $100,000 Pyramid

I was on $100,000 Pyramid this week. This is a reflection of that experience.

I was on the season premiere of $100,000 Pyramid. Just saying that is surreal enough. Yes, this is really long and it'll have a few downer moments, but stay with me until the end for the (hopefully) heartfelt uplifting message. This was written in three distinct timeframes: first, within 12–24 hours after taping; second, one month later; and third, during the week of the airing.

How We Got Here & What Happened

For important context, I am writing this part less than 24 hours after the taping. I wanted to document my feelings right after everything happened. I will add a section at the bottom after the show airs as I'm sure my feelings may change or not feel as raw.

This experience was a dream come true for someone like me. I’ve spent my career creating experiences that make games and knowledge fun for others, but it’s been a lifetime bucket list item to be on a game show myself. I remember, back in high school, talking to my friend’s dad about how cool it would be to create a game-show-themed restaurant. I never did that, but trivia nights in restaurants became my way of bringing that vision to life.

Even though being on a game show was a dream, I didn’t actively pursue it for many years. Sure, I’d take the occasional Jeopardy! test and bomb it, but I always figured that show wasn’t for me anyway—too fast-paced, too detail-oriented. I enjoy marveling at those who are great at it.

In February 2023, though, I saw an application for $100,000 Pyramid and thought, "Why not?" I filled it out, filmed a video, and was stunned when I got a call just a few days later. I went through five sessions with different producers, getting more excited each time, but eventually, the calls stopped. I later got an email saying they’d gone with someone else. I was disappointed but understood—it’s the nature of the game.

Fast forward to November 2024. I was sick with pneumonia when, out of the blue, a producer called me. She told me I had done really well last time and they wanted to bring me back. Despite my illness, I was honored and thrilled to give it another shot.

The process to get on the show is long, detailed, and incredibly fun. The producers are phenomenal—they treat you like friends by the end of it all. One even told me during practice, after I slipped up and used a preposition, "You’re too damn good at this game to lose $50,000 because you said the word ‘in.’" I'm so grateful for the chance to have had a peek behind their curtain and to have played these games with them. Come tape day, they are your biggest fans. They want you to win. They are great at what they do and it shows.

I practiced obsessively. Over the last few weeks, I worked with 33 different people—friends, family, coworkers—many of whom didn’t even know what they were helping me prepare for. I’m so fortunate to have such an amazing network of people willing to help. My friend Casey would start all his phone calls to me with random words, trying to get me to guess the category. All these practice sessions were invaluable. I became a student of the game, analyzing trap words like “Monday,” “UFO,” and “Sidewalk.” You can't say "day," "object," or "walk" for any of those. I had a list of 200 such words that I practiced (thanks, Holly). At night, I would constantly interrupt my wife’s TV show watching asking her to take small breaks to practice.

I also worked on refining my focus, cadence, and speed, along with trying to predict actual categories. I preferred categories with words that started with certain letters—they make it easier to guide your partner toward specific guesses. That approach helped me in rounds like “Peanut Butter and Jäger” and the “Ex” category later on. My confidence grew as I nailed practice round after practice round. With every mistake, I learned and got better. Thanks to a little help from my friends, I felt prepared.

And then there was my friend and colleague Derek. Just days before taping, he decided to fly down from Seattle to support me. I know several others would’ve done the same if given the chance, but it meant so much to me that he showed up for what he knew was a once-in-a-lifetime experience. He didn’t even get to see my taping since it’s a closed set, but he made the most of his time and went to The Price is Right during my episode. I was really hoping for a great story about him winning a car while I was filming, but alas, that didn’t happen.

On tape day, I woke up at 4 a.m., terrified I’d oversleep and miss the car picking me up at 5:45. I woke up with a decent-sized cut on my forehead—courtesy of my wedding ring while sleeping. Not the best way to start the morning.

By 6:15 in the morning, I was at the studio, filling out paperwork, getting briefed, and mingling with the other contestants. We had to turn over all technology to the producers. Everyone was buzzing with excitement, and we quickly formed a bond, cheering each other on as people got called for hair and wardrobe. We even created our own little "Winner’s Circle" practice area with our chairs. I can’t wait to see how they all did. I regret not writing down their full names so I could connect with them after all is said and done.

We had three official practice rounds: one low-key with a producer, one in a simulator, and one on the actual set. I "won" all of my practice Winner’s Circles and did well on all my main rounds as well. When I was the first to go in the Winner’s Circle on the actual set, which was the final audition, I won with 23 seconds to spare on “Things Two People Do.” I jumped up, screamed, and took it all in. I felt ready.

But as the hours stretched on—9 hours since I’d arrived at the studio—I started to feel the tension creeping in. I told my producer I was working on my nervous energy just being regular energy.

As we waited in the final minutes outside to enter the stage, the producers noticed my calm demeanor and hoped I’d bring more energy when the cameras rolled. I assured them I would, but inside, I was focusing. My cool, collected practice sessions felt far away and that was a bit daunting. The friendly faces I had played with couldn’t help me now. This was the real deal. Hours and hours of practice led to this—a chance at 60 seconds in the Winner's Circle.

The thing about this game is the payout is great. You can win up to $150,000. That’s a big prize for game shows these days. But even just getting into the Winner’s Circle is likely to earn you close to $10,000, even if you don’t win.

Before filming, they had me rehearse my "figure skating" intro line about 15 times (my fault, not theirs - we were trying to get it just right), and even that was looping in my head. Truth be told, that was not one of the original three intros I gave them, but they liked that story, so they asked me to go with it.

I met my celebrity partners, Pete Holmes and Mark Duplass, before we started. I only got about 3-5 minutes with Pete and a quick handshake from Mark. Both were incredible—funny, kind, and clearly experienced at making contestants feel at ease. I couldn’t have asked for better partners. They apologized when they got something wrong when they didn't have to do so. They made me feel welcome and were excited to play. I also enjoyed seeing them interact with each other during breaks trying to help each other win in the Winner’s Circle.

While I had some clean sweep rounds, overall, I didn’t play my best. Far from it. I was capable of so much better. And that’s devastating. I was flubbing clues I’d normally get in practice in seconds. Or if I didn't flub them, I'd go about them much more awkwardly than I had practiced. I knew I'd need to get 19 or 20 each game to have a chance to move on. I can't remember exactly where I ended up in each game, but it was around 17 or 18. I guess we’ll see when it airs how bad it really was.

Horror movies are a blind spot for me, and in a rush with a couple seconds left, I confused Psycho with The Exorcist. Yes, I know the difference, but in that moment…yikes. I could see my hands shaking on the screen.

I also stumbled on a couple of Pete’s clues, probably passing too soon. I did this because I couldn’t see the clock nor did I know how many we had correct at that point. That definitely threw me off. The category did not help here either - words with three consecutive vowels. Even Pete joked about it.

And then there was "predator"—instead of saying something clear and simple like I did in practice when I had that same exact word, like "Chris Hansen’s To Catch a BLANK," I awkwardly tried to explain a child predator, leading Mark Duplass to say 'molester' on national TV, before a Hail Mary attempt with Nashville’s hockey team. It was an embarrassing moment, and knowing the Mystery 7 round had a trip to Peru on the line only added to my nerves. It was absolutely in my mind “don’t miss a trip to freakin’ Peru as the clues were being given” But I did. This and The Exorcist are the ones that gave given the most anxiety post taping.

But here’s the other thing about this game: you’re only as good as your opponent. My competitor, Juanita, was amazing. She played such a clean game. She won the maximum amount possible on the show. I was genuinely thrilled for her and even cheered loudly (probably too loud) as she headed to her second Winner’s Circle, yelling, "Go get it, Juanita!" She’s recently relocated to Hollywood to pursue acting, and her winnings will help her make LA home. I couldn’t be happier for her.

I’ll also take 1% credit for her win (besides my obvious main game flubs). Earlier in the week, I had a dream that we got to choose our celebrity partners from a bunch of them sitting at cafeteria tables. I told Juanita and the others about it in the green room, saying I picked Rachael Ray in said dream because she said we had "minion vibes." Sure enough, during Juanita’s Winner’s Circle, she said "Rachael Ray" as the second thing for people who cook food. That definitely brought a smile to my face.

Michael Strahan was incredibly kind to everyone. After the game, he shook my hand, told me I played great, and joked about our shared gap-tooth look, calling us "bold, confident men." That laugh helped ease the sting a bit.

Still, as I type this less than 24 hours later, I’m admittedly gutted. Yes, the money would have been life changing. I thought a lot about what I’d do with it. But it's more so that I know I’m a better player than what I showed. I'm sad. I feel embarrassed for not playing my best and for letting down the people who will be excited to see me on the show. I feel sad for blowing my shot at doing so much better.

I know that complaining about not doing well on a television game show is, in the grand scheme of things, completely ridiculous. It’s a game—one I was lucky enough to even have the chance to play. And yet, as I stood outside the studio before taping, I could literally see the smoke from the wildfires drifting through the sky, a stark reminder of real problems unfolding just beyond this small, controlled world of bright lights and buzzer battles. People were losing homes, firefighters were risking their lives, and here I was, stressed about missing a clue. It puts things in perspective, and honestly, I feel a little guilty even writing about it. But I also know that disappointment and gratitude can exist at the same time, and maybe that’s just part of being human.

Even though I was beyond exhausted, I could barely sleep a wink last night as I replayed all the what ifs. But it's important that I admit I played less than my potential. There's no excuses. I own my performance no matter how much it hurts in this moment.

Before I left, my youth baseball team gave me a basket filled with thoughtful gifts all with little notes: a Whatchamacallit candy bar for when I couldn’t think of an answer, a "Coach Mark" coffee mug, Michael Strahan beard oil, an autographed baseball by the kids, and a lot more. There was also a crocheted lucky duck in there that I made a point to take with me in the green room. It was a small but meaningful token, reminding me of the support and encouragement I had from my team. The duck wasn’t allowed on stage, and maybe that’s why things unfolded the way they did, or at least that’s what I like to think. I wanted to make those kids proud the way they make me proud when they put forth their maximum effort. As a joke before I left for LA, I bought a huge $6 plastic gold chain to wear to practice tomorrow. I probably won't do that now.

I was envisioning a watch party in my head the last few weeks. Now, I don't even want to do that as I'm wishing I could celebrate how much better I played instead of silly mistakes I made. Maybe (and hopefully) my feelings will change as we get closer to the airdate.

I'm definitely saddest for my kids, Parker and Theo. And I'm 100% misty-eyed as I type that part here in the airport. The hardest part will be pretending for the next couple of months that I might have won. Parker and Theo were so excited when I called them after the taping. For weeks, Parker’s been asking if we’ll go to Fenway Park to sit on the Green Monster or take a cruise “when” I win. Parker was really excited to film a video of me last week when it became official I'd be on. Theo would adorably try to play the game randomly in car rides. Five-year-olds on Pyramid are not great, but super funny. I’ll have to keep up the charade until the episode airs.

But, I know my obligation is bigger to them than winning money on a game show. It is my duty to raise them as kind and resilient individuals. I do hope one day they'll read this when they are older and are in a potentially disappointing spot of their own, cause we all have them. I hope this teaches them, it's okay to be sad about something, but there are bigger lessons to be learned in how you handle it.

Despite the sadness and disappointment, I’m proud that I tried. I created an opportunity for myself. I gave myself a chance. People in high places saw something in me and kept me moving along in the process.

More importantly, I stepped out of my comfort zone and faced a fear I’d avoided for years—the fear of failing publicly. I hope my kids and anyone reading this can take away a lesson: it’s okay to fail. It’s okay to try something hard and not succeed. What matters is getting back up, brushing yourself off and being proud of the journey that got you there. Take risks, embrace challenges, and cheer for others, even when they win and you don’t.

Perhaps being on the game show wasn’t the bucket list item after all. Maybe I just needed a really public way to show others—friends, family, my community, and my kids—that it’s okay to be uncomfortable when you just try. Just get yourself in whatever hypothetical game it is you're trying to play in your own life. Take the class, ride the bike, have the hard conversation, or make a new memory. Give yourself a shot. You deserve it.

This was hard. It wasn’t the outcome I wanted, but I’m glad I took the shot. And I won’t let this be the last time I try something scary.

To everyone who helped me prepare: thank you. I'm so grateful. To my family, my friends, my coworkers, and my kids: I’m sorry I didn’t do better. But I'm so grateful for your support and excitement. I’ll fail again, but I’ll face it with courage, knowing the incredible support system I have around me. And if you made it this far in the story, you're the real hero. Thanks for reading. Don't be afraid to put yourself out there and try something hard. In the meantime, I'll be watching The Exorcist.

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One Month Later: Reflections and Reality

It’s been a month since taping, and I’ve had time to sit with everything. Time has softened some of the sharper edges of disappointment, but I’ve also spent a lot of time unpacking why I felt so crushed by the experience in the first place. After all, this was a bucket list item. I accomplished it. So why did I walk away feeling so low?

After it was safe to reach out, I messaged one of my celebs on Instagram to thank him for his kindness and for being part of my dream. To my surprise, he replied within 10 minutes, reassuring me that I should feel great about how I played. He reminded me that it was my first time in the spotlight, and even though he’s experienced, he still gets nervous. The stress of the moment can really take a toll on performance. He said he’s done a lot of game shows and always jokes that you’re about half as smart up there as you are at home practicing, which was oddly comforting to hear.

I think the answer lies in the fact that I didn’t go prepared to lose. I went in confident, practiced, and ready to win. I never once entertained the idea that I’d play worse than I had in practice. But I did. And the gap between how well I performed in preparation and how I played under the lights was wider than I ever anticipated. At least in my mind. And I say that without having seen it on TV yet.

I wasn’t prepared for that. I wasn’t prepared for the letdown of not living up to my own expectations. I’ve been on stages before. I didn’t think I’d be impacted by the moment. But I clearly was. It was surreal, and even now, I couldn’t tell you exactly what all my rounds were—I just know I didn’t perform at my best.

Maybe part of it was how abruptly it ended. One moment, I was in the middle of this whirlwind, something I had spent months preparing for, and the next, I was being ushered out with half a turkey sandwich in hand, already being asked what I would do differently next time. It was jarring. So much time and energy had gone into preparing, and suddenly, it was just... over. It felt unceremonious in a way that didn’t match the weight of what it meant to me. I was in a car and off the lot within ten minutes of the taping ending. That contrast made it all the harder to process.

In the weeks that followed, I went through a real slump. For two weeks, I felt completely unmotivated. I ate like garbage. I beat myself up. I couldn't shake the thought that maybe my spot should have gone to someone who would have fared better. I felt like I threw away my shot. It’s not a game where I can just go try again the next day. The opportunity had been so rare, so special, and in that moment, I felt like I had wasted it.

But now, with some distance, I feel more gratitude than regret. I still wish I had played better, but I’m grateful for the experience. I’ve also realized that my response to this whole thing—the taping, the airing, the aftermath—is just as important, if not more so, than how I performed in the moment. A close friend reminded me that my kids (both my own and the ones I coach) are watching. I can show them what it looks like to take a hit and keep moving forward. To admit to yourself that you aren’t perfect, that you could have done better, and then go try again. And I will try again. It might not be a game show, but it’ll be something.

I also recently found out that my episode is the season premiere. That news hit with mixed emotions—excitement, nervousness, a little dread—but mostly, I’m happy to see how it all turned out and to finally be on the other side of it.

I wish I had been kinder to myself in the immediate aftermath. I wish I had given myself more grace. But at the end of the day, I took a shot. I stepped onto that stage and gave it my best in that moment. And I’ll keep doing that, no matter how many times I stumble along the way.

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The Airing: Getting on the Other Side of It

This week has been really hard and great at the same time. People are genuinely excited for me to be on the show and see how I do. That means a lot. However, when I hear people saying they can't wait to see how much I win, that definitely stings each time. It's not their fault. They don't know.

I got the okay to start promoting the appearance earlier in the week along with some official pictures. The pictures were a nice reminder of the fun of the day. I debated for a long time about a watch party, but I woke up on Tuesday and tried to stop feeling sorry for myself and decided I'd throw one and do what I do best - gamify this shit. So, I played the role of Michael Strahan hosting some games of Pyramid for people who were kind enough to attend. I wanted to make it fun for them as they’ve been so supportive.

It meant the world to me that 25 friends showed up for a late-night watch party to see my episode air—seriously, why 10 PM!? But despite the late hour, the energy in the room was electric come air time. I’ll never forget the roar of the bar when Pete Holmes introduced me and I appeared on the screen. That might be my favorite moment of this entire experience. I’m thankful I got that part on video.

I know everyone came hoping to watch me win. One person even joked, “You wouldn’t drag us all out here to watch you lose.” And that’s been the hardest part—everyone just assumed I had won. In the same way I prepared to go and win. But I’m okay with how it turned out. More than anything, I’m grateful—for the experience, for the support, for the messages, smiles and hugs that reminded me how lucky I am to have this incredible community around me.

One of the best surprises of the night was reliving the first round. I had completely forgotten that I went 7-for-7! The bar erupted again during that moment, and it was so much fun to see it play out. I forgot I actually had a few 7 for 7s.

The moments that stung right after taping—the ones I replayed over and over in my head (Exorcist, predator, Pete’s clues to me)—still gave me a bit of that “what if” feeling. But watching the episode, they flew by much faster than I expected. Time and perspective really do work wonders.

The first person I messaged after the episode aired was Juanita. I couldn’t have been happier for her shining moment. She played an amazing game, and I was so happy to see her succeed. Watching her Instagram stories this morning has been awesome.

At the end of the night, Theo (my five-year-old son) came up to me and said he was sad that we wouldn’t be able to go to Fenway Park to sit on the Green Monster anymore—that’s what he had been hoping for. That one stung, because I would’ve loved nothing more than to share that moment with him. He actually took the loss pretty hard the rest of the night. We’ll still get to Fenway at some point.

In the end, I didn’t walk away with the big prize, but I walked away with something better—memories, joy, and the overwhelming support of so many people, both near and far. That’s what truly matters. Thank you to everyone who reached out, who watched, who cheered. I’ll never forget it.

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Five Fun Facts About the Experience:

• The cardigan wasn’t mine—I’ve never worn a cardigan a day in my life. They asked if I’d wear it, and I had no issue with it. I didn’t even sweat in it.

• Even without a studio audience, there was still a warm-up comedian. He performed just for Juanita and me.

• There were no clocks anywhere. I had no idea what time it was until I left the lot. In total, I was on-site for about 10–11 hours.

• The season premiere intro was filmed at the very end, after they decided it was a contender to open the season.

• I went through an extensive background check—mostly because I have such a common name. At one point, I was asked if I was involved in about 25 different paternity cases across the country. (The answer was no.)