The hustlers

Today’s conversation: Tangle’s Isaac Saul on building a nearly $5 million profitable news business without a big personal brand or funding.

I won’t be sending a newsletter on Thursday for Thanksgiving. But we will have an episode of People vs Algorithms. Be sure to check out last week’s episode about why Main Character Energy is so valuable.

Today, I have a column on why the hustlers are also well positioned.

My Russian neighbor told me a remarkable story of how he started his career. He was working for a state-owned company in the twilight of the Soviet Union when Gorbachev kicked off the perestroika reforms. Suddenly, there was opportunity. The catch: It took initiative. Sergey, a natural-born hustler, seized it, brokering between a paint factory with excess inventory and all the shabby businesses in need of paint. He recognized that distribution systems were built on faulty information flows. 

By the time the Soviet Union collapsed and Russia was in its Wild West phase of capitalism, Sergey was running arbitrage schemes by driving around Eastern Europe to buy goods hard to find in Russia to resell them at a markup. Soon he was bringing Russian goods to sell in markets in Poland to get zloty to buy the Polish goods for resale in Russia. Hustlers find a way.

Along with Troy Young, I was a guest on Dylan Byers’ podcast, The Grill Room, to discuss Media People, the idea I shamelessly ripped off from Troy that there’s a type of person who makes media. Dylan pressed us toward the end to name current Media People, since many of the examples were old. We stumbled through a few – Emily Sundberg? Dylan’s boss? Olivia Nuzzi, of course – but I realized that Media People are more often than not from a different era. Tina Brown, the quintessential Media Person, is 71. 

The decentralized media landscape instead advantages hustlers because, like Sergey experienced in Russia in the 1990s, the system is breaking down. Volatility and crisis are uncomfortable for most, but for hustlers, it’s the gift of opportunity. In the early pandemic, I was told a smart piece of advice: It’s during crisis that the league tables change. 

Hustlers are built differently. They have the dog in them. They get to start. They have a strong bias to action. They’re enthusiastic sellers. They show up every day. They’re willing to do whatever it takes. The fashion media CEO who faked having an EA to make the status-conscious fashion people think he was more important than he was. The salesman who went top to bottom in a downtown skyscraper to sell copiers. Starting a business is hard. I used to misidentify these stories as the fripperies of the successful; I’ve come to realize they’re explanations.

An important note: a hustle is neither a grift nor a racket. A grift is about avoiding the hard work with a shortcut. A racket is a systemic phenomenon that isn’t driven by personal agency. Hustles, in the parlance of Silicon Valley, begin with “just doing things.” Real hustlers are builders; the fake ones pretend “entrepreneur” is a job title or still think it’s relevant where they went to college and in some distressing cases, high school.

Hustlers are active participants who itch to make something out of nothing, even if it means buying a coin-operated laundromat. 

Hustling got canceled during the pandemic. The Web 2.0 era vintage “hustle culture” was raucous and more marketing slogan: coworking spaces with millennial minimalism design aesthetics, “Rise & Grind” neon signs and prosecco on tap. The hustle of Adam Neumann and Elizabeth Holmes became watchwords for grift. It became toxic to work too many hours. Hustling became too branded, too crypto-adjacent.

Hustling is back now, only it's been rebranded as “high agency.”High agency is a way to turn a blind eye to the negative excesses that are part and parcel of hustling to focus solely on the positive. Being high agency means you are willing to take risks and to stand on your own. High agency people see problems as solvable.

The cultural pendulum is swinging back to high-agency hustlers. I sense a lot of the backlash to DEI was because it was highly bureaucratic. The oppressor-oppressed narrative is never going to fly in this kind of society. Americans like the cowboy aesthetic for a reason that goes beyond outfits. The taboo against “cringe” is fading as giving-a-shit becomes cool again. The Sixers are poised for another disappointing season, but rookie VJ Edgecombe became an instant fan favorite on draft night when he described “them long nights” of seven years in childhood when his family used a generator for electricity.

The Trump administration’s immigration enforcement tactics expose an essential tension: Americans love fairness but they also love hustlers. And immigrants are by definition hustlers who seize opportunities. I’ve rarely met an immigrant who isn’t a hustler. Maybe some Brits who work at ad agencies.

The highest-agency person I know, a card-carrying hustler, told me he paid for college through a cell phone arbitrage in high school. That allowed him to “unplug from the matrix.” 

“My goal in hiring people is to catch them before they’ve been completely subsumed by the negative way of thinking.” That negative way of thinking is centered around all the reasons something won’t work. “My orientation is what people did in high school. When no one was looking, did you try to make money?”

Hustling is a feature of capitalism. Even celebrities need to hustle. You realize that somewhere like Cannes, where legitimately famous people prostrate themselves to the CMO of a snacks company. I’ve seen a member of the British royal family trying to hustle a food documentary project at a networking dinner. Justin Bieber has to livestream himself playing pingpong and skateboarding for money because streaming means artists need to tour nonstop. 

My advice to the young: Do not believe you are above the hustle because you have a degree from a fancy school. The safe career paths are far more perilous than ever. I overheard a hustler the other day telling a non-hustler how he should go to every house on the Venetian Islands and offer to clean their massive windows, charge $500 a pop because rich people will pay, and do 10 houses a day. Problem solved. 

Olivia Nuzzi is not just a Media Person, she is also a stone-cold hustler. She didn’t take the typical elite school and family connections path to what are still the elite institutions of the old media world. She hustled her way there. I mean, cohabitation with Keith Olberman? Many of us resent the hustlers because they simply want it more badly than we do. 

Most Media People are not hustlers. I find that hustlers are typically outsiders whereas a lot of Media People are insiders. Hustlers find a way in chaotic situations and seize opportunities. And yes, sometimes that means hustlers are opportunists, although the best hustlers are merely opportunistic. There’s a difference.

Hustlers are outdoor cats who are more comfortable at the lumber yard than waiting patiently by the fridge for milk. They were frequently indifferent students who chafed at systems seemingly designed to reward box checking and conforming. They tend to have Carol Sturka Energy. 

Matt Paulson, the founder of financial newsletter company Marketbeat, is a feral hustler. He’s a great X follow, and instructive of the type of person who will do just fine no matter what AI does to the media business. He started blogging for money in college and kept at it. I’ve never trusted serial entrepreneurs. I’m partial to those who work hard at a single idea and come out the other side with “overnight success stories” that take several years.

Isaac Saul is another hustler. He started Tangle in 2019 after being frustrated as a Huffington Post reporter because everyone assumed he was biased to progressivism. His simple idea: There were more people like him interested in hearing how both sides see issues in order to make their independent assessment. He willed Tangle into existence without any backing or unearned advantages like media’s long parade of nepo babies. 

“When I started Tangle, I was a nobody,” Isaac told me. “It's easy when you're famous already, but it's a lot harder when you're sort of making your way with the idea that you're executing. I went from zero to 13 to a hundred to 150 to 400 [subscribers]. I had those early days for the first year.”

Now, Tangle has a 12-person team, 70,000 paying subscribers, a $4 million recurring revenue run rate. 

Many of the independent operator success stories gloss over the hard work part. It became almost taboo to talk about that during the so-called woke era, too toxic. Hard work is intrinsic to hustlers. It can be comical and performative, as you’ll find in X threads and pretty much every LinkedIn post. Many assume successful people do not work hard. I’ve found the opposite is almost always true.

“Every morning I wake up to a blank letter with a blinking cursor, and for that morning, the future of media is just writing the letter,” Emily Sundberg writes in her five-year anniversary post. 

Many rank-and-file reporters deeply resent Olivia Nuzzi’s celebrity. It is “everything that’s wrong with modern media.” I understand that. Being a reporter is a mostly thankless job. And the current system almost penalizes original journalism. The rewards and incentives are undoubtedly, as David Sirota, says “to get in front of a YouTube camera or publish a NYT oped riffing off of others' expensive reporting rather than actually doing the costly, difficult & never-gonna-break-even work of reporting.”

Bridget Williams, an exec at Hearst Newspapers, once remarked to me that journalism needs “enlightened mercenaries.” Put another way, it needs hustlers that find a way to allow for the hard work Sirota mentions. In fact, he’s doing that himself with Lever News. I don’t see the government or billionaires coming to the rescue, so not much more choice than to hustle.

Isaac Saul started Tangle in 2019 without a platform job, a big name, or the institutional head start many Substack-era independents enjoyed. He describes himself bluntly: “When I started Tangle, I was a nobody.” In this episode, we talk about how he hustled his way from zero readers to a 450,000-person list and 70,000 paying subscribers, and how he’s trying to make the shift from a creator-led project to a durable media company. We get into his decision to add new voices, the limits of solo output, the temptation to do more, and why he thinks the next phase of media is about building systems, not personalities.

Listen to the conversation

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