In Conversation with Gabe Fleisher of Wake Up To Politics
An interview about Substack, Gen-Z politics and Kamala Harris
He’s just 22, hails from Missouri and relocated to Washington, DC, for university. From that short bio, you would think Gabe Fleisher is very much the new kid on the block. He isn’t.
Gabe first started his newsletter in 2011, aged just nine (that fact also makes me feel old). Though his parents aren’t political animals, Gabe’s imagination was captured by the 2008 US Presidential race, when a young senator representing Illinois took on Republican grandee John McCain.
Barack Obama’s successful first run for the White House “really fascinated” the youngster and drew him into politics more broadly. Gabe’s outlet, then called The Daily Rundown, went live as The Tea Party Movement began to kick-off.
A precursor to the rise of Donald Trump, the low-tax and anti-government campaigners helped reshape the American Republic.
It was this political backdrop and the elections of 2012 (the Super Tuesday primaries and Presidential votes) which started to put WakeUpToPolitics on the map.
Gabe’s local newspaper The St. Louis Dispatch also began to cite Gabe’s work. “That was the first moment of real growth,” he said.
The next flood of subscribers came in 2017 thanks to a feature in The New York Times, when Gabe was 15. By then Trump had entered the White House and captured the Republican Party.
The TV star’s campaign against Hilary Clinton was a watershed moment for the mainstream media as we entered the age of ‘fake news’. Despite Trump’s protestations, digital publications, particularly apolitical ones, saw a bump in subscribers.
WakeUpToPolitics, which had 2,000 subscribers before the New York Times piece was published, was no different.
“The free newsletter…is a surprisingly sophisticated, well-researched summary of the day’s political news,” The Gray Lady opined.
The turmoil of the first Trump presidency gave Gabe plenty to write about. With his newsletter ticking away, his next big move would be a relocation to DC to study at Georgetown University in 2020.
“It was a bit of a cultural shock,” Gabe said. “But it was always my dream to go to college and eventually move and live in DC. As someone who loves politics, there was nowhere else that I could envision myself going to. There are some times that I miss the Midwest, but I do really love DC.”
As he still finds his feet on the media circuit, Gabe is still looking to publish his newsletter each day before 10am East Coast time. He’s not, however, looking to compete with Politico, Axios, Punchbowl or other newsletter-driven outlets on being the first out of the gate.
Gabe’s readers, who aren’t typically Washington insiders, are more interested in the quality of the product. “I don’t sweat too much on the timing,” he stressed.
Now at 50,000 subscribers and another general election set for November, the future looks bright for Gabe. Amongst other things, he’s started to appear more in other outlets as an interpreter of the Gen-Z outlook.
Gabe is keen not to pigeonhole himself around the demographic issue, but he does appreciate the fact the he brings unique insights to the discussion. “Those are always pieces that get a lot of feedback, and people are really interested in them because I think there is a lot of curiosity about young voters in the country,” he explained.
Joe Biden’s White House has also invited the journalist to Gen-Z-focused events, while Gabe has stressed that he has good working relationships on both sides of the political divide.
Issues-wise, he’s most interested in foreign and economic policy. As for the biggest questions of the general election campaign, he’s currently focused on who Democratic nominee Kamala Harris may appoint as her running mate:
“A four-person shortlist has emerged pretty quickly in the hours since Harris locked up the nomination: Gov. Andy Beshear (D-KY), Gov. Roy Cooper (D-NC), Sen. Mark Kelly (D-AZ), and Gov. Josh Shapiro (D-PA).
“All four are white men hailing from red or purple states, an attempt to balance the ticket with Harris, a Black woman whose only pre-2020 campaign experience was in deep-blue California.”
Beyond the editorial, Gabe is thinking about experimenting with video, especially on Substack, and will seek to continue to grow his newsletter. Nothing fancy here, just pushing on – day-by-day – with the newsletter he launched all the way back in 2011.
The full interview can be found here.
🤔 Other things in tech and media I’ve found interesting
The Guardian lay-offs: Some big names are out at The Guardian as the outlet goes through a series of voluntary redundancies. The Press Gazette is reporting that Jim Waterson, who fairly recently became the outlet’s political media editor, is amongst the journalists who have decided to leave the publication.
The Mill takes on London: It’s always nice to hedge bad news with good news. So, here goes: Joshi Herrmann’s The Mill group is looking to hire two hacks in London. The newsletter-powered company has obviously seen a gap in the market as The Evening Standard moves from a weekly to a daily and CityAM continues to undergo a series of changes under new owners, THG. The Mill has made great strides in the North of the country, but London has always been a different kind of beast. Joshi was featured in The Observer this weekend where he talked about the plans.
The internet prudes. Friend of the newsletter Chris Stokel-Walker has an interesting piece in Digital Frontier looking at how Web 2.0 is turning against sex, arguably the very thing that helped the web grow so much.
The FTC weighs in on AI. A group of US regulators, including the FTC and DOJ, have called for more competition in the generative AI space. “The joint statement notes that while AI has the potential to become one of the most significant technological developments of the past couple of decades, it also raises competition risks that may prevent the full benefits of AI from being realised,” the press release states.
t’s unclear what has prompted this intervention, but there continues to be a big divide in the world of generative AI — those who want to make the technology open-source, and those that want to keep it under lock and key, whilst building a regulatory framework around it.
🎙️ The Political Press Box
My latest long-form interviews include Morten Morland, Seb Whale and the FT’s Lucy Fisher.
🎥 Video essays
📖 Essays
How disinformation is forcing a paradigm shift in media theory
Welcome to the age of electronic cottages and information elites
Operation Southside: Inside the UK media’s plan to reconcile with Labour
📧 Contact
For high-praise, tips or gripes, please contact the editor at iansilvera@gmail.com or via @ianjsilvera. Follow on LinkedIn here.
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