FiveThirtyEight’s Nate Silver’s advice to founders

FiveThirtyEight.com, named after the number of votes in the Electoral College, was founded in 2008 by Silver as a data-driven news site that covered politics, economics, and sports—or, in other words, a blog. It grew out of Silver’s election forecasting, initially anonymously, as a blogger for the progressive site Daily Kos. With a background in sports data, inspired by the groundbreaking work of the analyst Bill James, Silver’s political prognostications earned him a reputation as a digital oracle of sorts. Bill Simmons, the former ESPN writer and podcaster who founded The Ringer and later sold it to Spotify, used to refer to Silver as a “witch” when he had him on as a guest.

But now Silver says all the data wizardry in the world won’t matter much when budgets start shrinking. Against the backdrop of massive layoffs at Disney, Silver announced his departure from FiveThirtyEight in April on the social media platform then known as Twitter, surprising an industry that considered him near-untouchable.

Silver’s first commercial deal as a founder was to license FiveThirtyEight to the New York Times’ Upshot section from 2010 to 2013. When his three-year contract with the Times expired, Disney’s ESPN acquired the brand and website. In 2018, the site moved within the Disney portfolio to ABC News as ESPN revised its digital strategy. The intervening five years had seen Disney dramatically overhaul ESPN’s digital footprint, including the ousting of Silver’s longtime acquaintance Bill Simmons.

Silver sounded a sad note about his own departure. “Disney layoffs have substantially impacted FiveThirtyEight. I am sad and disappointed to a degree that’s kind of hard to express right now,” he wrote. “We’ve been at Disney almost 10 years. My contract is up soon and I expect that I’ll be leaving at the end of it.”

The founder subsequently told The New Yorker in June that his last day at ABC News would be at the end of the month after his contract expired, and The Economist’s G. Elliott Morris ultimately replaced Silver to oversee FiveThirtyEight. 

Roughly two-thirds of FiveThirtyEight’s staff was cut, Silver shared in an edition of his newsletter, the Silver Bulletin, in May. Following an interview on the House of Strauss podcast, he discussed some regrets but also zeroed in on his advice for founders in a similar situation: don’t trust your corporate parent with your business model.

‘Be wary’

FiveThirtyEight’s move to ESPN was considered a “peacetime acquisition,” Silver wrote in his newsletter on Saturday. That was “at a time when its business looked very, very good.” But that was the issue. 

ESPN wasn’t focused on helping FiveThirtyEight turn a profit because the impact this low-expenditure franchise would have on the gargantuan sports network was next to none in the grand scheme of things, Silver told Strauss in the podcast interview.

Now, Disney is looking to sell (at least) a stake of ESPN given its slowing revenue amid the demise of cable television and rise of streaming, with Disney CEO Bob Iger growing audibly tired of the TV business in general. 

“I guess the general lesson here is that, if you’re some sort of small business founder, be wary of a situation where you’re being acquired by some larger business for ‘strategic’ reasons and there isn’t really a plan in place for your business unit to make money,” Silver wrote.

Silver isn’t the only founder who said goodbye to his company and watched as it languished. To take an example from a much greater scale, Steve Jobs himself was fired from Apple in 1985 after a power struggle with the board. In his absence, the company lost focus, betting on a new kind of processor that couldn’t compete with Intel’s while watching Microsoft grow to dominate the tech space. After it flirted with a fire sale to Sun Microsystems, Apple was near bankruptcy when it brought Jobs back into the fold by acquiring his NeXT venture.

We all know what happened after that: Just a $3 trillion valuation and, ironically, persistent rumors that Apple might acquire a troubled Disney.

But Silver doesn’t seem to have plans to return to Disney any time soon. 

“That’s not necessarily to say I regretted the decision to go with ESPN/Disney,” Silver wrote. “I sort of knew what I was getting into and I appreciate what they did for us.”

Now, Silver is working on a book about gambling and risk for Penguin Press, he shared in his newsletter in May. The book will cover a broad range of topics including poker and sports, artificial intelligence, venture capital, and the fall of FTX, as well as declining life expectancy and changing attitudes toward risk in American society.

He might also start another media venture, but one with a broader focus than politics, Silver told The New Yorker.

Next time, he’ll likely keep his own advice in mind: If you’re a founder, you need to figure out how your company can make money because your new parent won’t necessarily do it for you. In the worst case, as Silver experienced, you’ll watch as most or all of your staff gets laid off. 

“It’s a weird thing, this whole notion of founder-driven business,” Silver told Strauss about his experience building a blog into a media company over a decade, and now leaving and seeing it run by someone else. “In some ways, on my part, it was a very arrogant idea from the start.” 

Silver did not respond to Fortune’s request for comment.