Good morning, this is Mike Hofman, aka Inc.’s editor-in-chief and the person who brings you our 1 Smart Business Story each day.  
 
Today: Dan Ni, whose growing roster of TLDR newsletters are definitely worth reading—and reading about.  
 
Ni opens up to Inc. about his long journey to founder-market fit and how a debilitating medical condition derailed his tech career, until it provided a path to success.  
 
Read on to discover:  

What are your must-open newsletters? Let me know, as well as any ideas you have for how this newsletter (or another one from Inc.) could become your next inbox favorite, by emailing me at [email protected]. 

After a rare medical syndrome sidelined Ni’s career, he created a popular suite of tech newsletters that boasts seven million subscribers.

BY ROB VERGER, SENIOR EDITOR

The winding path that Dan Ni took on his way to creating the TLDR suite of tech-focused newsletters is littered with career detours: a job out of college as a quant trader, a rare and painful medical condition, the founding and sale of a SaaS business, and even a stint at culinary school. 

Today, the media company that he runs publishes a dozen newsletters that all together reach more than seven million subscribers. Ni, 35, employs 22 people full-time, all of them remote, and last year for the first time the company raked in revenue over eight figures—and is profitable.

“I think it’s an inspiring story for a lot of people trying to grow their own media companies,” says Adam Ryan, co-founder and CEO of Workweek, a platform for professional networks.

The main TLDR tech newsletter—a reference to online slang for “too long; didn’t read”—arrives in the inbox of some of its 1.6 million subscribers, with a subject line populated by brief headlines and corresponding emoji. (News about Tesla might have a little red car next to it, for example.) Subscribing is free, and the company generates revenue by selling sponsored links in the newsletter from prominent companies such as AWS, Google Cloud, and Anthropic. An ad can cost as much as $30,000 per day to run.

“TLDR was such a side project at the time,” Ni recalls, of the newsletter’s early days in 2018. “I really didn’t even think of it as anything other than my own newsletter for a really long time.” 

Ni started in finance. After graduating from Yale University in 2012, where he studied economics and math, he scored a job at Jane Street Capital in New York City as a quant trader. “Back then I was really in the grind,” he recalls. “I just wanted to make a lot of money, like a lot of people right out of college.” But then the pain started. 

“I started getting a really bad ache in my jaw,” he says. “I was like, man, why does this hurt so much?”

He tried not eating solid food and taking the muscle relaxers his doctor prescribed. Nothing helped. Eventually, he decided to take time off work and go live with his parents. The plan was to get to the bottom of things medically and then return to New York. He ended up staying in Columbia, Missouri, for about six years. 

Eventually, Ni got his diagnosis: Eagle syndrome, a rare disorder which, in his case, causes abnormal growth of two small bone structures near his ears and jaw called the styloid process. “It’s essentially this very small bone that just keeps growing,” he says. “It’s very unpleasant, because it feels like there’s a giant knot in your head.” He ended up getting two surgeries. 

It was a painful time. “There was definitely a several-month period when I couldn’t eat solid food because my jaw hurt so much,” he recalls. “And I actually spent probably a month of that drinking Soylent.”  

On a podcast, Ni described this period as his “wandering in the wilderness time, when you kind of feel like a loser, and like nothing’s working, but ultimately you do learn a lot from those failures.”  

As he recovered at his parents’ house, Ni spent time online searching for ways to earn a little money. He played online chess, learned to code, and dabbled in arbitraging gift cards and creating Squarespace websites for people. “I was in these internet money-making niche rabbit holes for a while,” he recalls. 

He also spent time reading forums, such as Y Combinator’s Hacker News. That’s how he got the inspiration to start his own B2B business in 2015, called ScraperAPI. “It was a tool that allowed developers to build really scalable web scrapers,” Ni says. Imagine that a company wants to track the prices of a multitude of Amazon products; ScraperAPI could power that. “I kind of fell into building this B2B SaaS business, because I was like, oh, this is an interesting tool that I could build, and there’s a need for it,” he recalls, “And I found customers pretty quickly.” Eventually, it became a “real business that employed real people,” about 10 full-timers as well as contractors.

But the work wasn’t all that rewarding. “Honestly, I did not enjoy running a SaaS product, because nobody has ever written to a SaaS company to say, ‘Hey, great job today.’” Instead, he says, the feedback was more likely to be negative, like if something wasn’t working the way it should. 

He ended up selling the company for seven figures in 2020, and he looks back at that time period as one of stress and burnout. Ni decided to attend culinary school, enrolling in a six-month program at the Institute of Culinary Education in Lower Manhattan. He recalls that he didn’t “even want to look at a computer for six months.” He didn’t realize at the time that a side project he had already launched would become a multimillion-dollar business.

Back in 2018, before Ni sold ScraperAPI, he had cooked up something else while still living in his parents’ basement: the TLDR newsletter. Today, there are a dozen of these newsletters, all with different focuses, like TLDR Founders, TLDR AI, or TLDR Crypto, which was the first to spin off from the main newsletter. 

Ni was vaguely inspired by the influential, Millennial-friendly newsletter theSkimm. “I think theSkimm was the first time I heard about a pure-play email newsletter,” he says, leading him to think that “somebody should do this for tech people.” TheSkimm, he says, gave him the awareness that newsletters “exist as a medium.” Although TLDR was hardly the first tech newsletter, it offered insiders the ability to stay up-to-date with important industry news easily.

It was ScraperAPI that helped Ni get TLDR off the ground. Initially, many of the readers were those who were using the free plan offered by that company, he says. He emailed the contact list, asking them if they would like to sign up for his newsletter. He used MailChimp to send out the newsletters for the first few months before switching over to a more affordable email service provider called EmailOctopus, which is based in London. “We’re still on EmailOctopus today,” Ni says, “and I have to say, we must be their biggest customer.” 

To grow his subscriber base, he placed ads on Reddit and Quora, and also struck mutual promotion deals with other newsletters. He reflects that the time period, around 2018 and 2019, for him, was “very amateur, like Wild West sort of stuff.” 

That Wild West era was when Substack was still in its early days, a platform that Ni notes “made the medium much more mainstream.” It was also “certainly before a lot of these other newsletter platforms that have sort of popped up since, like Beehiiv”—the buzzy platform started by Tyler Denk in 2021. “Sometimes it’s better to be early than to know what you’re doing.” 

Referrals also helped boost his audience. “Probably after Quora and Reddit got us to, like, I would say, the low tens of thousands of subscribers, referrals started being probably our biggest source,” he explains.

By around 2022, he was able to grow the TLDR list to around 200,000 subscribers and hired a staffer to help run ads on Meta and other platforms, he says. Today, he estimates that subscriber growth comes from an approximately 50/50 mix of organic sign-ups (from Google or referrals) and people seeing ads on platforms like Meta’s or the social media site X. It costs between $5 and $10 to acquire one subscriber via ads, he says. 

The newsletters now reach more than seven million subscribers, and Ni has some pretty straightforward advice for the approximately 30 part-timers on his team who author them: “Write for somebody that works in the industry,” he’ll say. “For our engineering newsletter, I say, ‘Hey, like, write for somebody that’s been at Google as a software engineer for at least two years.’” In other words, this is not 101-level content. 

His guidance to his writers is to include only information that they would also find worthy of sharing in a group chat with their industry peers. “If you wouldn’t forward this to your colleagues in Slack, don’t put it in the newsletter,” he says. The goal is to avoid filler content that isn’t actually compelling. “That sort of strategy generally attracts just a better quality audience.”

That audience is what he describes as “the broader Silicon Valley diaspora.” So, it’s not just people who work in the tech industry, but also at tech companies in hubs like New York City. To achieve this level of insiderness, Ni hires writers who are working in the industry. The crypto-focused newsletter, TLDR Crypto, is authored by “two guys at Coinbase,” he says.

The TLDR AI newsletter is written in part by Andrew Tan, a founder and investor who states that the newsletter has more than 900,000 subscribers. “I think what makes TLDR unique is several things,” Tan says. “One is this principle of finding people who are experts in their fields and who can really sift through the signal versus the noise.” 

“The other is that almost all the newsletters lean pretty technical,” he adds—information that would make sense to insiders. 

There are some big-picture reasons that Ni and TLDR have been successful in the field, Tan notes. “I think it’s a combination of three things,” he says. One is “technical expertise,” and the second is “business acumen.” 

“Growing and monetizing a newsletter is not something everyone is great at,” Tan says. And the last thing is “being a great person,” he says, as well as Ni only hiring good, kind people who are team players. 

“I’ve never heard anybody say anything bad about Dan,” says Ryan of Workweek, which publishes B2B industry newsletters, like the HR-focused “I Hate It Here.” 

Ryan is a longtime subscriber of TLDR, going back to its early days. “What’s been so impressive is the simplicity that they’ve taken there,” he says. “And I say that with, like, a ton of respect.” He says that what the newsletter has done, through its simplicity, is to make something that is “pretty gratifying for most readers.”

Then there’s the fact that Ni launched TLDR as just a side project. “I think some of the best things always start as side projects, a little bit, and not trying to make money—and the fact that he really wasn’t in the newsletter space before and didn’t know much about it, and then just kind of learned and learned and learned,” says Ryan.

Today Ni, 35, lives in San Francisco with his wife, Ellen Le, and their 9-month-old son, Dan Jr., and he no longer struggles with jaw pain. He’s pretty philosophical about the whole journey, which is very much an illustration of the idea that there are multiple pathways to success. “It feels like all these things when you’re younger are just super existential,” he says. 

People tend to think, “Oh my god, if I don’t get this job at Goldman, it’s over. If I don’t get into Teach for America, it’s over.’” 

“What I find most impressive is that he’s overcome a lot,” says Andrew Namanny, host of the Permission to Shine podcast, who interviewed Ni last year. “He spent six years at home in his 20s after working at Jane Street Capital—that’s a humbling moment. That’s a punch in the gut, but he turned it into a positive.” 

“I think everybody just kind of finds their way in the end,” says Ni. “At least for people that are lucky enough to be born in America, in a middle-class family that has parents that really care about them, you’re actually surprisingly robust to temporary failures.”

This article first appeared on Inc.com.