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August 1, 2025

Meeting Nate Silver

Meeting my Heroes is an occasional essay series from Matt Carmichael.

On the utility of stalking for introverts

It was the first decade of the century and data was en vogue. Baseball was embracing a new(ish) breed of stats (finally) that measured things that mattered more than the traditional metrics. Moneyball was a hit book and became a hit movie. Freakonomics, the Tipping Point and Nudge were books about data and research and combining data from different sources to better understand the world and people’s behavior in it. Civic data – using public data for public good – was also taking off. Chicago was at the center of many of these movements. And then came social media and suddenly everyone had a dashboard for everything.

Moneybag, Freakonomics, The Tipping Point and Nudge* (and eventually Nate would write a book like this too) had something in common that I love. They made you look at the world differently. Especially made you look at things you looked at every day but notice them.

Granted, sometimes that can ruin said thing, like Paco Underhill’s “Why we Buy.” That book was amazing in that it deconstructed the experience of moving through a store or a quick serve restaurant. In so doing it points out the things retailers still (and this book came out decades ago now) do wrong. The part that ruins everything is he then explains how totally simple it would be to fix said problems. Now every time I open a straw by the big fountain drink machine and there isn’t a small garage can nearby for the wrapper I would so completely obviously have in my hand at this moment I’m filled with rage. Paco is still a genius and I was honored to get to meet him when I realized I was driving by his office in New York and called to see if he was there. He graciously gave welcomed me in and gave me a tour and it was amazing. This might even have been the same trip where I shared a limo with Dan Ariely and he gave me one of the weirdest book promotion items I’ve ever seen. I interviewed him a few times over the years and wound up giving him advice on what to do in Chicago with his family when he was in town once. Dan’s books, too, made you look at the world differently.

I was writing about all of this data stuff for Crain’s Chicago Business (and later Ad Age) and finding excuses when I could to hang out at 1871, the new small business incubator in town where all of yesterday’s nerds were suddenly today’s cool kids.

Enter Nate Silver. He was a young baseball junkie and poker player who go interested in political polling and modeling election outcomes. His first big feat was correctly predicting the outcome of Barrack Obama’s first election in 49 out of 50 states. His 2012 election forecast was also on point and led to memes about him being a witch.

Crain’s Chicago Business named him a 40 under 40 in 2008, before his forecast came true. Which meant he was invited to the ensuing cocktail party and networking event. As a staffer at Crain’s, so was I.

I’ve talked about how showing up is a super power. That’s a recurring theme in this series. I’ve discussed stalking, which is a not nice way of putting a thing I do sometimes. Perhaps it’s more tactical interception. Or intentional meeting… I don’t know and am open to suggestions.

But there’s something super useful about going to an event where you know basically no one (or, in this case I knew my coworkers but not a lot of other people) with the intent of meeting one person.

If you’re an introvert like me, it’s like a diversion. You’re not walking into a room filled with people you don’t know. You’re walking into a room with one specific person you want to meet in it… somewhere.

It’s like you’re on a mission. Because you are.

So I set out to meet Nate Silver. My goal was to connect and meet him and then later have lunch with him and get to know him better.

I accomplished that.

Tangent: The next year I would get more clever and pre-stalk the folks I was most interested in and write the profiles of them myself. Hence I wound up writing the Andrew Mason piece about the founder of Groupon. He, too, became someone I would have lunch with from time to time even as his company ballooned like crazy. My favorite Andrew Mason moment came during his companies first earnings call. Here he is, talking to investors for the first time as a CEO of a publicly traded company. And during the call I get a notification that “Andrew Mason is now following you on Pinterest.” It’s certainly plausible that those notification were not in real-time. But I like to think that he was bored and surfing Pinterest while his CFO talked financials. Because that version is hilarious, and also on point.

Anyway, back to Nate. Lunch with Nate Silver was crazy. He seemed so young and had so much of the world ahead of him. Offers were pouring in for all kinds of business ventures. He was going to move to New York and figure out what was next. But I found myself giving him advice like, “dude, get an accountant and a lawyer who specializes in all the things you are going to need.” (That last bit came from the as-yet-unwritten Meeting the Goo Goo Doll.)

Later we could keep in touch and try and fail to hang out when I was in New York.

But I reconnected with him after the 2012 election when his book dropped.

We did a video interview at the hotel he was staying at, which turned out to be a bit of a production. I had in mind to ask him if he was a witch and see if I could get him to wear a witch hat. That would have broken the Internet at the time. However I sensed he didn’t have a sense of humor about it, so I didn’t do the witch hat thing.

NateSilver-CCB-YouTube.png

But with Nate, or Andrew, or Paco, or so many of the other heroes I’ve talked about, the formula is pretty simple: Do your research. Show up (that’s most of the battle). Make a connection. Have some reason to keep the connection going. Don’t make single-serving friends when you can avoid it. Follow-up. Send an email with a thank you and a reminder of some things you talked about, or something interesting they said, or suggestions for something they might like to read or a podcast episode based on what you discussed. Offer to connect them with someone else they might find interesting.

All of this is really just good manners, but it’s also important.

And when you get a chance to see the world, see it differently, and notice it more.

*note, when awesome books make you look at the world differently, sometimes that’s because they’re not entirely accurate in their portrayal of things. It’s good to be curious but also good to remain skeptical.

Following my own advice, here are some links for further reading if you liked these stories about Andrew Mason, Paco Underhill, Dan Ariely, and of course, here’s what I wrote for Crain’s about Nate Silver (and Andrew):

Nate Silver on life as a political piñata and pop-culture meme

By Matt Carmichael November 12, 2012

In 2008, the world watched as a 30-year-old stats geek did what few seasoned pundits could pull off: He correctly predicted the winner of the Obama/McCain presidential race in 49 of 50 states by creating a probabilistic framework for analyzing polling results. Crain's also played the odds, predicting big things for Nate Silver by naming him a 40 Under 40 even before the election votes were cast. Since then he's been busy making our prediction look good with his extremely popular FiveThirtyEight.com blog now hosted by the New York Times, and with his new book, “The Signal and the Noise: Why So Many Predictions Fail—But Some Don't.”

In 2012, Mr. Silver outdid himself by picking the winner in all 50 states once the ballots were finally counted in Florida. It was a bruising election fight for the candidates, and occasionally for Mr. Silver. At points he became a punching bag for conservative pundits who mistook his fact-based prediction of a comfortable re-election bid for President Barack Obama for partisan gamesmanship. As the popularity of his blog soared, it led to a cult-of-personality forming around him. Sites sprang up on the Web like IsNateSilverAWitch.com (after the election his status was upgraded to “Probably”). On Twitter, memes like #drunknatesilver took off with tweets like this one from @alanmaguire: “Drunk Nate Silver points at the night sky. The star he is pointing at flickers, then dies.”

Crain's sat down with Mr. Silver shortly before his talk Friday at the Chicago Humanities Festival. We wanted to get to the bottom of some of these Internet rumors. What follows is an edited version of our conversation. In the end, as the Republicans found out, Mr. Silver aims to speak the truth, even if it's not as much fun as the fiction you wanted to believe.

Crain's: Are you or are you not in fact a witch?

Mr. Silver: I am not a witch, no. Although my friends and I went out for drinks the other night and they gave me a witch hat, and I told them, "You can take pictures, but they can't go onto Twitter or Facebook. " I feel like Christine O'Donnell or something, but no I'm not a witch.

What exactly do you like to do when you're drunk?

Just hang out and rap with my friends about baseball and stuff and politics. The usual stuff.

Have you followed the Drunk Nate Silver meme?

I have. I don't know if it's my favorite of the Nate Silver memes. Somehow that Nate Silver becomes very clever when he's drunk. I think that doesn't usually work with the biology of most people, myself included.

What is your favorite?

I like the Nate Silver Facts. Some of those are very flattering. It's all really strange. I'm waiting for it to calm down in a few days because I can't read Twitter now without having this character. . . .I mean that's the thing, you kind of become almost disembodied from this character who is this representation of you but who doesn't necessarily reflect yourself anymore. It's a strange thing to have happen.

Did one side's data beat the other side's data?

There are a couple things here. No. 1 is that Obama invested all this money early on in the ground game. It took a while to pay off. Through the spring and summer, they weren't registering very many voters. Then in some of these states, close to the registration deadline you saw Democratic registrations go up — in Pennsylvania, for example, and in Nevada and a few of the key swing states. You saw this little move toward Obama in the polls in the end. That could have been Hurricane Sandy, it could have been the economic news getting better, but it also could have been that the voters were getting in tune with the campaign. It turned out that the Obama campaign had done a better job contacting them and getting them out to vote.

Can polling account for a good ground game?

Well, Obama did beat his polls in quite a few of the swing states on Tuesday. So the answer is maybe, maybe not exactly. I don't think it's going to be something that's going to make a five-point difference, but if you get a little bit of extra turnout, that certainly might help. And you might get some voters to turn out who the pollsters consider "unlikely voters" so they're in the pool of “registered voters,” and those polls had Obama doing slightly better but they get excluded from these “likely voter” models. But you did see a big disparity in the ground game this year. You've been hearing some stories from Republicans who are saying, "Now that this is over, I have to say that this Romney ground game was a total disaster.” For Romney, who is supposed to be a kind of a data-driven guy himself and a good manager, I think that's kind of a nightmare.

In your book you talk about an Italian earthquake forecaster who made a very bad prediction. Since publication, he has actually been sentenced to jail for it. How do you feel about that?

You talk about bad incentives. . . .If you get thrown in jail for making a bad forecast, that would probably prevent people from trying to do good science eventually. Although I should say about that earthquake forecast, there's a little bit of legal blame to go around. They did tell people that “you have nothing to worry about.” There had been a bunch of foreshocks of small earthquakes in this part of Italy, and (city officials) literally said, “Go home and have a glass of wine — you have nothing to worry about.” Then you had a fairly major earthquake hit and people weren't prepared for it.

Here’s a link to the video interview:

On the 2012 and 2016 elections:

Usually these elections where you have an open seat election are, are pretty close. So I would expect a competitive election in, in 2016. But you know, when the Republicans won big in, in Congress in 2010, that's basically what we, what we said would occur. So it's, it is odd to me that people associate it with being, oh, it's this liberal site and personally, my politics lean left to center on social issues, more in the center on economic issues. But but look, I wanna get the forecast right. That's where my incentives are, right, is to be as accurate as I can be. And the fact that people think that anytime, anytime you say something other than, oh, it's a toss up, or, oh, it's 50 50, or oh, both sides are right, they think you're being partisan. Whereas I think it's kind of delusional not to seek out any truth in <laugh> in the evidence, right?

I think that's a job of, of reporting and journalism is to find where the truth lies. And there are a million different routes to do that, but I think the conventions of political reporting are, are so strange that that kind of, I stick out more there. Not 'cause I'm doing anything extraordinary, but because the other, the, the baseline, the competition is frankly, pretty, pretty bad. Well, look, I think if, if, if we have a forecast and, and Republicans don't like it or Democrats don't like it, that kind of goes with the territory, right? You're never going to win those fights. But if you, if you're engaged by, by pundits, right? <Laugh> and usually I, I think that if you're a pundit and you're trying to make some statement about how the horse race looks and how the campaign looks, right, and then you're criticizing me then you better be careful because they have a really terrible track record, right?

Including many pundits on Tuesday who predicted not just a Romney win, but a potential Romney landslide, right? And so usually those predictions aren't very well versed in, in the data. And this is not just a one-off example. I, in my book in other books people have looked at how these predictions do over the long term, and they have, they have no real skill at all. And to me, what it means is that if you constantly get things wrong when you're predicting things right, that means you're out of touch with reality and there's no more polite way to put it. So if you're a pundit who, who thought that that Romney was going to sweep to a landslide and win Pennsylvania and Minnesota, right? Well, you have, you have a chance you can get that right. If that turned out to be right on Tuesday, then I'd have to, I'd have to shut up. But I think those people are, are delusional and if there's no polite way to put it, and so of course they aren't going to like me saying that, but the evidence is in is, is pretty crystal clear.

On the Cubs:

Some things I think defy all laws of statistics and, and probability. Yeah. but look, it usually takes a good three or four years to turn to turn our team around, right? So you think maybe they'd be, if things go to plan then in three or four years it might be competitive. Of course, being competitive doesn't mean that you, doesn't mean that you win, right? But who knows? I mean, if you're being rational about it, then the probability is that some point

At, at some point in my, in my lifetime I'm 34, the Cubs will win a World series. But, but I don't know if I'd be willing to place a bet on it. It was not a well-run franchise for, for long periods of time. Right. and you know, one of the theories is that because people would come and turn out and see the cubs rain or shine and whether they were good or bad, right? And they didn't have any incentive to get to get better. So in some ways it's, it's good now that that people in Chicago have turned against the Cubs a little bit and they can't guarantee a sellout no matter what anymore. It's probably what they need to kind of make sure that they, they actually have to put a good competitive product on the field.

I had this, this proposed bet with Joe Scarborough. I come from the world where being willing to bet on things means that you believe in something that you're not BSing, right? But that's not kind of the ethics of, I guess how that's not typical in, in journalism circles, I suppose. Right? but to me that that means that look, when you have a financial stake in, in something, right it creates better incentives. Most of the time I think people who are, who are betting their money are usually more to be trusted than people who are just betting on the reputation. Because reputation is very easy to, to manipulate, right? But if you are betting your money according to hard and fast rules, then then it keeps you, keeps you real. It's a reality check.

On what’s next for Nate Silver

I think I have another book to write. Yeah. I have you know, 5 38 will continue in in some form, but I, I know I've been getting a lot of, of interest from a lot of different circles and I just have to really kind of <laugh> relax for a bit first and then, and then start to start to sort through things. And I'm not looking to make any snap decisions exactly. But kind of maybe taking through the end of this year to kind of think about things and relax and take some meetings and just kind of setting myself up kind of mentally <laugh> and physically. 'cause I'm you get tired, right? For, for the next four years. And, and the big question is, do I wanna write about this recent experience of mine in some way or go in, in in a different direction, right?

And I dunno, I think I'll have to, I mean, that's something I will have to decide on fairly soon. But with the book, it's like, I mean, the book is a major commitment. The book, it took me four years to write the first book. You know, I was doing other things at the same time, so it wasn't four years only on the book. Right? but you live with that thing for <laugh> for a long time, right? So at all, at all decisions I have to make professionally at least, and that's the most important is what's the theme of the second book going, going to be.

https://www.chicagobusiness.com/article/20121112/NEWS06/121119975/nate-silver-on-life-as-a-political-pinata-and-pop-culture-meme

And here’s my 40 under 40 profile of Andrew Mason

Andrew Mason

29 | Founder, CEO | Groupon Inc. | Chicago

For someone with a life goal no less lofty than "changing the world," Andrew Mason doesn't seem to take himself too seriously. When he found out that his company, Groupon, was up against Abbott Laboratories for a Chicago Innovation people's choice award, he wasn't daunted by the voting power of Abbott's 68,000 employees. Instead, he and his staff put together a YouTube attack ad mocking "persistent rumors" that Abbott is "an illegal cloning farm." (Groupon didn't win.)

"I have awesome investors who are ridiculously supportive of the stupid stunts that I just can't help myself but do," he says.

Mr. Mason's investors, however, take him very seriously.

In late 2006, a cell phone pitch to veteran Chicago investor Eric Lefkowsky led to a $1-million investment in Mr. Mason's new company, The Point Inc. Mr. Mason was 26.

ThePoint.com aims to help people reach the critical mass needed for collective action. It has the potential to be a world-changer, but first it needed a business-changer. Running it as an ad-supported Web site didn't seem like the right model, so in 2008, Mr. Mason created Groupon to help fund it. A year later, Groupon Inc. (as the company is now called) is his most profitable venture, rolled out in 35 cities, with a rapidly growing staff of 100 employees.

Groupon also is a collective action site — collective buying action, that is. Each day, it offers one discount from a client business. If enough people sign up for the deal, it's on. So consumers save money, merchants get a risk-free boost in a tough economy and Groupon takes up to a 50% cut. Everyone wins.

Manny's Deli has run two offers on the site. The second deal quickly sold out of the 2,000 available "groupons," the e-coupons that are the site's stock in trade. "You're not really making any money on those customers the first time they come in," manager Danny Raskin says. But dinner business has since grown, and Mr. Raskin often hears customers mention the groupon. "Some of these people have become everyday customers," he says.

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