Unlike a startup where you build equity and sell, a solo newsletter is tied to the person and can't really be sold or walked away from. Gergely notes it might be worth four or five times annual revenue on paper, but you can't sell it like that, and the only true exit is to build an organization that runs without you, which he doesn't want.

The business is worth maybe 4-5x annual revenue but can't be sold like a normal company.
Because the value is tied to the writer, you can't really walk away.
The only exit is building a publishing company with hired writers, or stopping and losing the revenue.
You have to produce something great every week, in theory for the rest of your life.

“you basically have to get something awesome at every week in theory for the rest of your life”
Lenny · 46:30

“it'll have a value let's say four or five times the annual revenue as a business but you cannot really sell it like that and…”
Gergely Orosz · 47:30

#newsletter#business-model#exit#creator-economy

Hot Take1:04:30

You need real experience and pedigree, not just writing skill

Both agree the foundation of a credible newsletter is real, scaled work with great people, not writing ability alone. Lenny criticizes people starting newsletters with little real experience to share, and Gergely advises becoming an expert first, plus deliberately working your way into high-pedigree companies so people pay attention.

The content must be based on real things that worked and that you learned firsthand.
Many new newsletter writers haven't done much and lack real experience to draw on.
Gergely's advice: become an expert somewhere before you start, to be credible.
He deliberately built pedigree (JP Morgan, Skype, Uber) so his work got attention.

“there's a lot of people starting newsletters and tweeting who like haven't done much and don't have a lot of real life experience to share”
Lenny · 1:04:30

“become an expert somewhere somehow before you start because you'll be a lot more credible”
Gergely Orosz · 1:07:00

#credibility#career#pedigree#advice

Hot Take1:10:30

In-depth writing is an underserved medium as everyone moves to video

A YouTuber friend told Gergely that his early-2010s blog benefited from timing: while YouTube is now saturated with high-production content, few people write in-depth regularly anymore. Gergely adds that written content is more efficient for software engineers, who can scan it, making writing an underrated advantage even as competition shifts to video.

A friend with 200k YouTube subscribers noted YouTube is now crowded with high-grade production.
Far fewer people write in-depth, regular blog content, so the medium is underserved.
Fewer writers means less competition for those who stick with in-depth writing.
Writing is more efficient for engineers who prefer to scan rather than watch long videos.

“I don't see many blogs that are are writing in-depth stuff regularly I feel everyone went over to YouTube or Tick Tock”
Gergely Orosz · 1:11:00

#writing#youtube#medium#competition

Explainer· 1

Explainer1:02:00

Good goals vs bad goals: set the ones you control

From his time managing people, Gergely distinguishes bad goals (a promotion, hitting 20,000 subscribers) that depend on outcomes outside your control from good goals (learn a language this year, leave work at 5pm Fridays) that you can actually execute. He applied this to his own blog, where the goal was simply to publish, not to be read.

Bad goals like 'get promoted' or 'hit 20,000 subscribers' aren't within your control.
Good goals are actions you can take: learn a new language, share what you learned.
His early blog goal was to write once a month, which he could control and be proud of.
Setting controllable goals is how the rest tends to follow.

“those are bad goals because it's not in your control”
Gergely Orosz · 1:02:00

“a good goal is what you can do”
Gergely Orosz · 1:02:30

#goals#career#advice#management

Story· 6

Story09:00

The newsletter now pays more than his peak Uber compensation

Gergely walked away from a European big-tech package he thought he'd never match, expecting to earn far less as a writer. Instead the newsletter's income surpassed his Uber comp, and unlike a salary it keeps rising as subscribers grow, with no theoretical cap. He frames it as a surprising, partly situational outcome he never predicted.

His best year at Uber (post-IPO) was about 320-330k total compensation.
A comparable US role might have paid five or six hundred K, so Europe felt like leaving money behind.
He now earns more than at Uber, and earnings climb as the newsletter grows.
There's no theoretical cap, though churn and slowing growth are the real-world limits.

“in my best year at Uber I made about like 320 or 330 000 in total compensation”
Gergely Orosz · 09:30

“I'm now doing something I love and um in some strange way I guess it even pays better”
Gergely Orosz · 10:30

#newsletter#compensation#creator-economy#uber

Story13:00

A promise to himself and COVID layoffs pushed him out of Uber

Gergely joined Uber betting the mostly-stock offer was a lottery ticket, promising himself that if it paid off in four years he'd take a risk on something of his own. When COVID forced Uber to lay off half his 30-person org, he lost trust that the company was a family and decided to leave.

Uber roughly doubled his Skyscanner comp, mostly in stock, in 2016 before anyone knew it would IPO.
He promised himself: if Uber exits and pays off in four years, he owes it to himself to take a risk.
COVID layoffs cut ~20% of engineers, and he had to let go 50% of his own group.
Watching strong colleagues get cut for being on the wrong team broke his trust in the system.

“the short of it is it was a promise to myself and covet and Uber doing layoffs”
Gergely Orosz · 13:00

“if four years later Uber exits and I make a bunch of money I owe it to myself to take a risk”
Gergely Orosz · 15:00

#career#uber#layoffs#risk

Story17:30

Self-published books he expected to make nothing made $100k

Planning to spend six months writing one book before raising venture capital, Gergely got sidetracked and self-published two others in a few months. He assumed they'd earn nothing, but they made about $100k in the first year while he kept roughly 90% of the revenue, which made him rethink the startup plan entirely.

His original plan was to leave Uber, write a book, then raise VC for a platform-engineering startup.
He instead published 'building mobile apps at scale' and a book on tech resumes in a few months.
The books made about $100k in their first year despite low expectations.
Self-publishing let him keep roughly 90% of the revenue.

“they started making money they made about a hundred thousand dollars in the first year”
Gergely Orosz · 18:00

“I self-published it to the drum rolls of places where I get to keep I think like 90 of the revenue”
Gergely Orosz · 18:00

#writing#self-publishing#income

Story19:30

The fisherman parable that killed his startup plan

Doing the math on founding a VC-backed startup, Gergely realized that even a unicorn outcome would end with him wanting to teach, write, and share what he knows, exactly what he could do right now. He invokes the fisherman parable, where a decade of hard work only earns you the relaxed life you already had, to justify skipping the startup and writing instead.

A successful startup might net ~5% of a billion-dollar company after five or six rounds of dilution.
After buying things he didn't need, he'd want to share knowledge and make videos anyway.
The fisherman parable: work for years to eventually afford the simple life you already have.
He had enough savings to take the risk on writing directly, so he did.

“I would go off and do this for like 10 years because that's how much you need to plan to do it”
Gergely Orosz · 19:30

#career#entrepreneurship#philosophy

Story43:00

The surprising downside: it's lonely

Gergely, an outgoing person who liked office life, found working solo unexpectedly lonely. He misses the casual chats at the coffee station and lunch with colleagues, and now compensates by working from a shared techie office so he can say hi and make small talk.

He genuinely enjoyed his Uber team and the people, not just the work.
He misses spontaneous conversation at the coffee station and over lunch.
Solo work was lonelier than he expected, more than he anticipated.
His fix is a shared workspace full of other tech people for small talk.

“one is obviously it's lonely”
Gergely Orosz · 43:00

“I really like you know walking up to the coffee station and having a chat with people”
Gergely Orosz · 43:30

#remote-work#loneliness#creator-economy

Story57:30

The Hacker News post that split engineers into two camps

Months after giving up on his refocused blog, Gergely got a traffic spike that crashed his shared hosting, traced to a Hacker News discussion of a post he'd written six months earlier titled 'a comment is an invitation for refactoring'. High-karma engineers argued fiercely, some calling him an idiot and others calling it wisdom, and it showed him that people cared what he wrote.

He published six blog posts, gave up, then months later saw a huge traffic spike.
The spike came from Hacker News, a site he'd barely heard of, and crashed his hosting.
The post argued that a comment in code means the code should be refactored instead.
Silicon Valley engineers split into two loud camps arguing over it, proving people cared.

“it was called a comment is an invitation for refactory”
Gergely Orosz · 57:30

“some people called me an idiot some people called me the absolute wisdom”
Gergely Orosz · 57:30

#blogging#hacker-news#audience#writing

Tool· 1

Tool37:30

His focus stack: a 20-minute timer, a site-killing Python script, and a camera

To beat the distraction of Twitter (which he also uses for research), Gergely sets a 20-minute no-distractions timer and runs a simple Python script that edits his Mac's hosts file to block LinkedIn, Twitter, and Facebook until he re-runs it. He also likes focus apps like Sunsama for their video-camera feature, which makes him feel watched and accountable.

A 20-minute timer with a hard 'no distractions' rule gets him past the friction of starting.
A self-written Python script blocks social sites via the hosts file and must be re-run to unblock.
About five minutes in, a switch flips and he's heads-down in flow.
The focus app's video-camera feature makes him feel watched, forcing him to work.

“it's just a very simple python that I wrote for myself”
Gergely Orosz · 38:00

“about five minutes in there's a switch and I'm like I'm now actually like heads down and doing it”
Gergely Orosz · 38:00

#productivity#focus#tools#distraction

Takeaway· 4

Takeaway11:30

Thousands of micro-bosses and a raise for every great post

Lenny reframes the newsletter life as having thousands of micro-bosses instead of one manager, each of whom can quietly cancel. Gergely tracked in a spreadsheet how much his annual revenue rose a week after each article, and found a great post effectively handed him an instant raise, something a corporate job never does.

Instead of one boss, you have thousands of subscribers, any of whom can 'fire' you by unsubscribing.
Gergely kept a first-year spreadsheet tracking revenue change one week after each article.
A well-received article translated directly into a visible, self-awarded raise.
This tight feedback loop between good work and pay doesn't exist in a big corporate.

“instead of one boss I have thousands of micro bosses and one of them can fire me and many do every day”
Lenny · 11:30

“for doing something awesome you can just get give yourself a raise”
Gergely Orosz · 12:30

#newsletter#incentives#creator-economy

Takeaway30:00

Self-imposed deadlines are why he can write four books a year

Working alone, Gergely found his 15-year track record as a diligent employee evaporated, so he engineered external pressure by promising thousands of paying readers a post every week. He credits deadlines, not talent, for producing four-to-five books' worth of content a year, and cites how Dumas wrote The Three Musketeers as a serialized magazine job for money.

Left to himself, even a lifelong star employee wasted days without structure.
Committing publicly to paying subscribers created inescapable weekly deadlines.
He wrote roughly four to five books' worth of content in a year because of these deadlines.
Dumas wrote The Three Musketeers serialized for a magazine because he needed the money.

“I wrote like four or five books worth of content just last year it's because I have these deadlines”
Gergely Orosz · 30:00

“put in constraints for the things that you need to do and then you're gonna do that”
Gergely Orosz · 33:00

#productivity#deadlines#writing#discipline

Takeaway48:30

Why it's so hard to take time off from a paid newsletter

Because subscribers leave if you stop producing, time off is genuinely hard. Lenny invented a personal PTO policy of four weeks a year, capped at about one to two weeks at a stretch. Gergely contrasts this with Uber, where a four-month paid parental leave didn't affect his stock, and warns about burnout in a one-person business.

Stop producing great work and subscribers leave, so breaks are risky.
Lenny's self-made PTO is four weeks a year, rarely more than one to two weeks in a row.
At Uber, Gergely took a full four-month paid leave when his son was born and still got paid.
He now works ahead on less time-sensitive posts and treats burnout as a real risk to solve for.

“I invented this PTO policy for myself where I take four weeks a year off”
Lenny · 48:30

“they gave me a four month paid holiday”
Gergely Orosz · 49:30

#burnout#time-off#newsletter#sustainability

Takeaway56:30

Jeff Atwood's three steps to be famous on the internet

Gergely credits Coding Horror founder Jeff Atwood's old post 'how to be famous on the internet' as the advice he keeps returning to: write a blog post, do it a few times a week, keep going for two years, and you'll be famous. He found it ironic at first but increasingly believed it, and it's still the best advice he can offer.

Jeff Atwood ran Coding Horror, the most popular blog for software engineers around 2007.
His formula: write, publish a few times a week, sustain it for two years.
Gergely initially found it ironic but came to believe it genuinely works.
It remains his core advice, just with slightly less conviction that success is guaranteed.

“there's one write a blog post two do this like three times a week three you can do it for two years and I guarantee…”
Gergely Orosz · 56:30

#blogging#advice#consistency#audience

Frameworks in this episode

Controllable Goals

Double Down on the Pull

Earn the Right to Teach

Manufactured Deadlines

The 20-Minute Focus Ignition

The Time-Boxed Leap Bet

The Two-Year Publishing Cadence

Insights & moments

◆Hot Take· 3

A one-person newsletter has no real exit path