How I Won It All on The $100,000 Pyramid

ABC/Lou Rocco

I won $150,000 and an all-expenses-paid trip on The $100,000 Pyramid. Here’s how I did it.

I grew up loving game shows and — like a lot of kids who spent afternoons at grandma’s or watched Pat and Vanna at dinnertime — I always dreamed of playing on one.

Games like Jeopardy! or Who Wants to Be a Millionaire? were always my favorite. I loved that they rewarded smarts, not just luck.

This week, my dream finally came true and on another show I love that rewards thinkers: my episode of ABC’s The $100,000 Pyramid aired and, well, I did good.

Though shoutouts to Cheryl Reinwand, who still holds the all-time Pyramid winnings record. She earned her $150,800 and a trip to Fiji across multiple episodes back when the show would bring successful contestants back in the ’80s. And to Angela Watkins, who pulled the same trick on the same night, literally the episode after mine.

The experience gave me a lot to talk about and I’ve gotten a lot of questions from people about the process. So, figured I’d get some content out of this and here we are: my Pyramid story.


To be honest, my dream is to host something like Pyramid, but being a contestant is the next best thing. And, let’s be real, Michael Strahan’s rightfully going nowhere soon.

So earlier this year, I saw the show was casting online and — having watched it in the past and played similar games like Heads Up with friends — knew I’d be great at it. So I applied. It’s that easy. Beyond that, I wish I could give you tips on how to stand out, but it really comes down to the casting folks liking you. What they seem to like: energy, enthusiasm, personality. Don’t fake it, of course. But if you plan on trying out, make sure to bring out your best authentic self in a video and have unique reasons for why you should get to play.


Once I knew I was in the running for the show, I practiced like it was my full-time job. After my company shut down and laid me off in February, practicing was my full-time job.

Even before knowing if I’d make the final cut, all I did was practice. But it’s tricky with Pyramid. The game format is identical to the original 1970s show. But topical references, the types of categories, and what constitutes illegal clues all vary widely from iteration to iteration. “Things Associated with Golda Meir” might’ve been a category in the 70s — not today.

ABC/Lou Rocco

There are old Pyramid board games you can play if you buy them online. You can have your friends make up categories, but it’ll never replicate the real writers’ room. And you can play Heads Up or Taboo, and they do help — but the aesthetic still differs.

I found it best to watch as many episodes of the Strahan Pyramid’s first two seasons as possible with a partner. The fact you could only find Pyramid online by paying per episode on Amazon Video brought me some added cost but…worth it!

When the celebrity gave clues, I’d cover the bottom of my screen and try to guess. When the civilian gave clues, I would pause the stream and try to get my brother or sister-in-law or a friend to guess while I gave clues. I would have them reciprocate, all to learn how different people would approach the game. And when it came to Winner’s Circle, I’d do the same bit: pausing the show at each clue and trying to get my partner to guess as quickly as possible.

Not a perfect science, but — hey — worked out alright.


Finally, I eventually got the call to play my episode.  And I…wasn’t nervous at all. Anxious, sure, but some part of me knew I was going to do really well. In fact, I expected to win the $150,000. You can’t predict the trip because that’s luck of the draw, but I knew if I were lucky enough to land on that Mystery 7 square, I was going to win that too.

It wasn’t delusion or entitlement or white male privilege (at least I hope not; that would be really sad). I just had a feeling. I don’t feel it often, but it felt the same as when I applied against 400 people to get my old job hosting for the Padres: “I’ve got this.”

ABC/Lou Rocco

Looking back, I attest this to a bunch of factors. One: I’m really good at games like this. I’ve never been particularly good-looking, athletic, or physically talented. But when it comes to mental acumen and cerebral processing — well I wish being a nerd was more attractive on Hinge.

Two: I’ve been on TV before. It’s kinda my job. So whereas I imagine a lot of contestants who are actuaries or small business owners or whatever see the stage and the lights and the logos and might freak out a little — it felt second nature to me.

Three: I’ve luckily worked with a lot of celebrities before. So again, meeting famous athletes and movie stars to play with didn’t rattle me since I’ve been fortunate enough to deal with their kind in the past.

ABC/Lou Rocco

Four: they keep the studio SO cold. If you know me and how much/easily I get warm and sweat, this really gave me an unexpected advantage. I felt like Aaron Rodgers in a playoff game at Lambeau.

Five: I had practiced So. Much. I knew the game inside out by the time the cameras rolled. LeBron James takes 1,000 shots a day so he only has to make 20 during a game. That’s how I felt. I’d spent so many hours playing, all I had to do was keep doing what I’d done for months.


You can Google game show blogs and message boards for best practices when playing Pyramid, so I won’t rehash them all here. The basics: use opposites (“Not ‘up,’ but _____”), use fill-in-the-blanks (“Statue of ______”), use your body (instead of “it’s the thing you smell with,” just point to your nose).

Instead, the biggest thing I gleaned specifically from my time: read your partner. We played with Jon Lovitz for example.

I guessed Lovitz wasn’t a big sports fan. Nothing I’d ever heard or read about him led me to believe he was. So when I had to have him guess “The Eagles,” in a round about Pennsylvania clues, my first instinct as a big sports fan was “The football team in Philadelphia.” He gave me a puzzled look. If I kept down that route, it might’ve cost me valuable time as he potentially floundered. So I immediately pivoted to “old rock band. Hotel California” in the hopes that a band that was huge when Lovitz was younger would be a better clue. It was.

And my last bit of advice for any future players: be quick, but not rushed. This applies to main game and Winner’s Circle. On the one hand, 30 and 60 seconds, respectively, is not a lot of time. On the other — if you’ve ever watched Tom Brady in a 2-minute drill or held a plank at the gym or told someone you loved them for the first time and waited for their answer back — it’s an eternity.

Something I noticed a lot of people did watching practice episodes was rush to spit out as many words as possible as quickly as possible. All that does is lead to adrenaline and confusion and panic and, sorry, was that thing before about telling someone you love them too personal? Felt like maybe an overshare. Let’s move on.


Here’s the part where I’ll sound like a little bit of an asshole: none of my success surprised me. I was happy at the results, obviously — you can see that in my reactions. But after the initial shock and the ensuing elation, I next felt validation. I’d told myself the entire time I was going to win it all, and any other result would’ve felt like failure to me.

ABC/Lou Rocco

To the point that when my opponent and I headed down to the set together, I wished her good luck and she responded with a genuine “May the best person win!” In some Michael Jordan-level psychosomatic thinking, I took that as a slight. Like she was patronizing me. She was obviously just being a nice, normal person. But I used that to fuel my competitiveness. “I will,” I thought.

I realize now I sound like a big bit of an asshole. Probably thanks to all the sports teams that cut me in middle school.


I swear I’m a nice, normal person too! I just get very competitive at things I’m good at, and you can ask anyone who’s played bar trivia or shared an AP English class with me.

To wit: after we taped the show, I kinda blacked out a lot of the things I said and did and whole parts of the game. But the one thing that stuck with me for the months between the taping and the airdate was that I passed on getting Lovitz to guess the word “Stye” in one round.

The one clue I didn’t get left a bigger impression on me than all the ones I did, and the more I keep typing, the more I realize I should probably go see a therapist about all these pent-up competitive issues.

ABC/Lou Rocco

In all seriousness, I am truly ecstatic for having had the opportunity to play and grateful for the good fortune of doing so well. Gotta thank Jon Lovitz and Bobby Moynihan, obviously, and Michael Strahan was about the nicest and most charming guy you’ll ever meet. Want to also shout out my opponent Emily, who was very gracious to me when we spoke afterward. And thanks to all the people I practiced with — there were a ton of you, but you all know who you are.

Now I just hope they invite me back someday. I’ve still got Billy Crystal’s record to break.

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