Meet the Player Who Risked $100,000 on NFL Survivor

We interviewed the player who put $100,000 on a single NFL Survivor entry. Find out his strategy, mindset, and why he took the ultimate risk.

by Team Rankings - Jul 10, 2025

NFL survivor contests have exploded in popularity over the past few years, and in 2025, they’re bigger than ever. Circa Survivor, the flagship $1,000-entry contest, has grown from a $1 million guaranteed prize pool in 2020 to a staggering $15 million this season.

But for some players, even that wasn’t enough.

Enter Circa Grandissimo: a new ultra-high-roller survivor contest with a jaw-dropping $100,000 entry fee, a $1.5 million guaranteed prize pool, and a max of two entries per person. It’s the most expensive NFL survivor pool in history, created for players willing to risk six figures on 20 weeks of NFL picks…if they make it that far.

Despite its simple format (pick one team to win straight-up each week, without being able to use the same team twice), surviving is anything but easy. Just ask the thousands who entered Circa Survivor in 2024, when the heavily favored Bengals lost to the Patriots in Week 1, and nearly half the pool was eliminated on opening day.

Now imagine making that pick with $100,000 on the line.

That’s the reality Ian Ritchie and his group embraced when they became the first to enter Circa Grandissimo.

When the contest was announced earlier this year, Ritchie and his Icon Racing partners — former MLB players Jayson Werth and Shawn Kelley, along with business executives Ken Kuykendall and Jeff Berry—didn’t hesitate. They were the first ones in.

PoolGenius caught up with Ian Ritchie to find out what motivated the first-ever $100,000 survivor entry and how his group plans to manage the risk, stay sharp, and handle the pressure of playing for six figures.

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PoolGenius: What’s the name of your Circa Grandissimo entry, and who’s in the group with you?

Ritchie: Our Grandissimo Entry is called Icon Racing, and it’s our horse racing group that decided to give it a go. The main partners are myself, Ken Kuykendall, who is the National Tax Partner at Price Waterhouse Coopers, Jeff Berry, former Head of CAA Baseball and now a Special Assistant to Buster Posey and the Giants, Jayson Werth, who owned Dornoch, a former MLB player, and pseudo face of horse racing over the last couple years, and former MLB reliever and friend of Jayson, Shawn Kelley.

We all started Icon Racing together, and our podcast, Off the Rail, talks about the fun of horse racing, baseball stories, gambling stories, amazing guests, and a lot of laughs. We decided to enter and, if we win, buy a bunch of horses at next year’s big sales. Icon also has about 40 investors who joined to be part of the fun.

PoolGenius: What’s your previous NFL survivor experience? Have you (or anyone in the group) played in Circa Survivor before?

Ritchie: I have played in Survivor the last couple of years at Circa with my Fantasy Football business, Fulltime Fantasy, and the Fantasy Football World Championships. Our results have been OK. We had some chances to sell teams for a big profit, but decided to go for broke and win the whole thing. We obviously did not win the whole thing, but ZERO regrets going for the big prize and not selling. It’s why we signed up!

Our Fantasy Football World Championships tournament is hosted at Circa, and it helped introduce our community to high-stakes survivors. It seems like a perfect match: high-stakes fantasy players signing up for high-stakes survivors at the same casino on the same trip to Las Vegas. It’s really an amazing experience we have been able to build with Circa as a great sponsor and partner of our fantasy drafts.

PoolGenius: What led you to put $100,000 on a single Grandissimo entry instead of spreading that across multiple entries or contests?

Ritchie: Great question. There was A LOT that went into it. First, having a bunch of partners who are “Go for it” kind of guys made it easier. Plus, I really love what Circa has built and is trying to build in the future. There is A LOT of respect there, and so being the first to sign up for their brand new contest was actually a REAL honor and something I was proud to do. When people do bold things, the rest of us who believe in that mission need to stand up and support it and do everything we can to help it be successful. Derek and his team have earned that respect and support, and I am fortunate to be in a position to sign up first.

Editor’s Note: Not sure how to begin your NFL survivor strategy? Start with our guide, How to Win NFL Survivor Pools, for expert tips and insights.

PoolGenius: With four of you on one entry, how do you resolve disagreements on picks? Does anyone have final say or veto power?

Ritchie: There is NO DOUBT that Jayson is the alpha of the group. If there is a disagreement, Jayson makes the call. He wants that pressure and thrives with that pressure and wants to be the guy on the hook. The dude is definitely a winner, and as Jeff Berry always reminds us, winners win!

PoolGenius: How many total entries do you expect to compete against in the Circa Grandissimo?

Ritchie: I am positive this contest will not only sell out but do much better than expected. Maybe it comes down to my faith in Derek (Stevens) and his team, but I have been very bullish on the numbers since the contest announcement.

PoolGenius: What’s your process each week for narrowing down picks? Any tools or data you rely on?

Ritchie: This is the million-dollar question. When to pivot away from a popular team for a statistical advantage over the field. I have been stung a few times being “safe,” and it’s a horrible feeling going down with the most popular weekly pick. The Bengals ripped my heart out in Week 1 last year, and it’s hard to forget or get over.

But the strategy differs in a smaller contest from the bigger survivor contest, which might have a little learning curve for everyone. I can say this definitively: we will leave no stone unturned, whether with tools, game data, information, or opinions of the best professional gamblers. But at the end of the week, whatever comes out of Jayson’s mouth will be the final say, and we will roll with it!

Editor’s Note: For more on this topic, check out our article: How the Size of Your NFL Survivor Pool Should Influence Your Picks.

PoolGenius: Do you feel you’ll have an edge in the Grandissimo? Do you view this as a pure +EV opportunity?

Ritchie: I don’t really know, which is funny. People always think they have an advantage or some type of angle on things. We really didn’t talk about any of that and really focused on the FUN, excitement, and opportunity to buy a lot more racehorses if we win. That’s really our goal, to load up on top-rated horses that we buy at sales, and I thought this would be a really awesome way to do it. Also, gives us a lot of content to discuss on the Off the Rail podcast, and leads up to the season, which was an added bonus.

PoolGenius: Is this the biggest single bet you (or anyone in your group) has ever made?

Ritchie: It is definitely the biggest bet I have ever made, and I am comfortable saying the same for Jeff Berry, Ken, and Shawn. Jayson is a different breed; this is right in his wheelhouse and something he is very comfortable with. I guess that is your answer, haha.

PoolGenius: Are there any teams you’re hesitant to pick (for or against), whether due to past burns, personal bias, or fandom?

Ritchie: There are definitely teams I feel like I am always on the wrong side of and have a hard time reading. The Bucs, Baker, Bengals, and Texans have cost me more teams the last few years than I want to admit. My fandom always has me taking a good and hard look at the Seahawks, which has also been dicey the last few years with Geno. I just try to avoid taking them because I root so hard for them anyway. On the flip side, I have had good luck with the Vikings.

PoolGenius: What would you like to see next regarding big NFL survivor contests like this?

Ritchie: I would love to find ways to get lower price point contests so more people can win their way into the $1,000 entry fee survivor. It’s a great feeder program that will help build the contest numbers and involve many more people who can’t afford the price tag. Many people I speak with would love a smaller, like $100 entry contest. With that price point, there are a lot of opportunities for growth and innovation of prizes to grow other contests.

Ready to Gain an Edge in Your NFL Survivor Contest?

Since 2017, PoolGenius users have won over $6.5 million in NFL survivor contests, from casual office pools to high-stakes entries like Circa Grandissimo. Whether you’re risking $20 or $100,000, a smart strategy starts with understanding win odds, pick popularity, and future value every week.

Give yourself the edge this season with the PoolGenius NFL Survivor Picks Tool to help you outlast the competition.