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Fourteen layers of advice from fourteen years of watching where the bodies are buried, from the founder of Skift.

Louis Cheslaw
1d ago

He essentially turned $200 million into $45 billion in two years, given back in a month and I'm not even clear what's left or what's next.

3d ago

The biggest risk of all is not taking one. Growth and comfort do not coexist. Every time I see a company protecting its core business rather than cannibalizing it, I know a competitor will do it for them—and far less gently.

4d ago

The best business returns are usually achieved by companies that are doing something that is quite easy to understand. The trick is getting first to a strong market position and then exploiting the advantages that follow. What you want is a natural franchise. A company can have a perfectly marvelous product and still be in a lousy business.

6d ago
notboring.co
AI is Oil, Not God

I think it comes down to whether you think AI is more Oil or God, more 'an economically useful commodity that can be scaled and refined to act as a multiplier on everything we do' or 'supremely intelligent and powerful being that's going to wake up and make humanity subservient (if we're lucky).'

1w ago

Kalanick's unifying idea for Atoms (and Uber before it) is that physical industries can be built like computers. In Kalanick's model, manufacturing is the CPU that transforms atoms, real estate is the storage layer, and transportation is the network that moves atoms from one place to another.

1w ago

Most turnaround stories are told years later, by the winner, after the ending is already known. That's why they always sound clean and polished. This one doesn't have an ending yet, and it's anything but clean and polished.

1w ago

"What started as a little tool suddenly becomes this glorious massive app that wants to do everything," he said — and "sometimes those apps get more in the way than they actually help."

1w ago

Most people overestimate what they can do in one year and underestimate what they can do in ten years. But the subtler error is assuming the next ten years will look like the last ten — the truly dangerous assumption for any investor or builder.

1w ago
whyisthisinteresting
The Dubai Creek Edition

In 1958, Sheikh Rashid bin Saeed, then Ruler of Dubai, borrowed around a half a million dollars from the Emir of Kuwait to dredge the creek. Dubai had no meaningful oil wealth at the time. What Sheikh Rashid had was a conviction that trade would define the city, and that the creek needed to be deep enough for modern ships.

1w ago

"You have lobster, and you have, whatever, let's say a good steak, and then you have the noodles, and then you have the rice. And so you come, and Anthropic and OpenAI, they take the lobster and the good steak. And there are only some noodles left, and you're like, 'Oh my God.' That's what happens today, and it's very, very, very hard not only to compete, but to retain the talent. So for us, building in Europe has been an incredible strength."

2w ago

A system built by a four-year-old startup went from prototype to a live combat mission, a month after another Corsair performed the first known rescue of downed pilots by an autonomous boat. Proving that a startup can build autonomous boats that are useful in combat is huge, but proving that they can build a great American shipyard again might be even bigger.

2w ago

Organizational culture is not about perks or ping-pong tables. It is the answer to the question: what behavior gets rewarded and what behavior gets punished when no one is watching?

2w ago

"It was obvious to us that 10,000 other people were going to go do the content thing," he says. For Ghetti, those "flashiest" uses missed the most important questions: how could we use technology to truly understand our own digital footprint, our own precious data? More importantly: if we got there, how would we control those treasure troves, so that we weren't putting the big AI labs like OpenAI in charge of our own "personal worlds"?

2w ago

For five and a half years, David Senra read one business biography a week, recorded a podcast about it, and published each episode to almost no one. Today, Founders is a cult obsession among some of the world's most powerful CEOs and billionaires, and a one-man business generating millions in annual profit.

3w ago

"Regardless of what industry you care about, automotive and aerospace, manufacturing and defense, climate, energy, semiconductors, electronics, the most important industries in the world are all a direct result from materials R&D. So to us, it felt like the perfect blend where you have this technology that is completely changing the paradigm in discovery, and you have this field that's 100-something years old and hasn't had it happen yet. That's a place that we should attack."

3w ago

Getting any one advanced reactor to criticality by July 4, 2026 would have been considered a minor miracle, but getting four with more to come means that there's going to be competition. Whoever can deploy most quickly, with a product that customers want, at the best price, will win. The field shifts from science to manufacturing.

3w ago

The crisis was not caused by the producers. It was caused by a society that believed it could consume achievement while attacking the people who make achievement possible. Without the producers, the system that exploited them can no longer function, and society collapses.

3w ago

Fabrizio grew up in poverty in Huánuco, Peru, and moved to the US at age fifteen, where he worked the lowest level jobs—busboy in a Mexican restaurant, door-to-door sales, etc. He eventually found himself in Nashville, and is now ready to make his mark on the country music scene.

3w ago

Building a platform is antithetical to building an ad business. A platform's goal is to feature third-parties; an advertiser's goal is to capture attention for itself. Investing in an entirely new technology, including developing hardware, fundamentally limits our addressable market; an advertiser's goal is to maximize its market size.

3w ago

It is not the employer who pays the wages. Employers only handle the money. It is the customer who pays the wages.

3w ago

Most people think the opposite of success is failure, but that's not true. The opposite of success is quitting. Failure is just a learning event. Companies that never fail are companies that never try anything new.

4w ago

The funnel of opportunity is wider than most people think, but the filter of execution is far narrower than most people realize. Ideas are not the scarce resource; disciplined follow-through on a single idea, long past the point of comfort, is what almost no one can sustain.

4w ago

But the duo figured that if they could generate a massive technical due diligence document for a data center site that would typically take six weeks in just six hours, they could charge $25,000 for it and enjoy margins more like a tech company than a consulting shop. They spun up dozens of agents to handle different tasks; in the initial workflow, one of the founders would email those agents to get PDFs back, and they'd grind long hours to turnaround a finished document for a client. "It looked kind of pathetic, but behind the scenes, a lot of stuff was going on," Stirrat-Ellis says.

4w ago

It raises the possibility that self-employment is the future of employment. It's easy enough to imagine a future in which relying on a group of other humans for your economic sustenance won't be as important — instead, we'll all be like little private ship captains, ordering around our crews of AI agents.

1mo ago

Failure is an option here. If things are not failing, you are not innovating enough. The key is to make your mistakes quickly and cheaply, not slowly and expensively.

1mo ago

"Anthropic and OpenAI salespeople walk in like heroes, get a contract, and leave to literally never be seen again." There's an adage in tech: nobody ever got fired for buying IBM. Habib proposes an update: "People should be getting f***ing fired," she says. "That's the best way to infuse some sanity into this market."

1mo ago

According to Xu, HeyGen hasn't really burned cash since it reached $10 million in ARR three years ago. Instead, the company proudly tracks a couple of other metrics: revenue for every dollar raised (now up to $2.70 for each $1 invested) and revenue per employee (now up to $1.5 million per full-time staffer).

1mo ago
longreads.com
The Mars Delusion

There will be tourism, and prestige luxury merchandise (Zubrin submits that the settlers might export artificial Martian diamonds tinted with a regolith hue). Perhaps they could sell the broadcast rights to low-gravity spectator sports like rover racing or something "comparable to the exhilarating Quidditch games" in Harry Potter; on Mars, Zubrin points out, "basketball players will be able to jump three times as high."

1mo ago

Most people overestimate what they can do in one year and underestimate what they can do in ten years. But the deeper error is that they plan in one-year chunks at all — the unit of compounding is decades, not quarters.

1mo ago

In the summer of 1994, there was a lunch. Me, John Lasseter, Pete Docter, the late Joe Ranft all sat down [at the Hidden City Cafe in Point Richmond, California near Pixar's head office]. Toy Story was almost complete and we thought 'well jeez, if we're going to make another movie, we better get started now'. So at that lunch, we knocked around a bunch of ideas that eventually became A Bug's Life, Monsters Inc., Finding Nemo. The last one we talked about that day was the story of a robot named Wall-E.

1mo ago

"If the business isn't good, you lose all of those optics eventually anyway. And this is hard for founders, right? Because, you are on a roller coaster, and sometimes founders look for external validation, right? 'Okay, well, if I have a lot of people, or if I have investors or whatever, it means that I'm doing well.' But really, the only thing that matters is, are you serving a really large market of customers, and do they love your product?"

1mo ago

Anthropic's Claude earns more revenue per user than ChatGPT does. That emphasis on B2B and superiority in coding models is really turning out to be a better commercial strategy.

1mo ago

The fear of job loss is "super justified," she told me; in her view, AI has made hiring junior employees "extremely expensive and completely unsustainable for a startup," because every hire now competes with the leverage of what she calls a "1,000x engineer."

1mo ago

In many accelerators, startups spend the program looking to ship and validate a minimum viable product, or MVP, readying it to a point to pitch to investors by demo day. In Elbow Grease, founders mostly knew how to use the various vibe-coding and agentic tools already in the market from companies like Anthropic and OpenAI; they could ship a product in a matter of days. Programming and workshops instead oriented around recruiting, sales and other aspects of company building.

1mo ago

Inside the companies pulling ahead — Anthropic, Cursor, Cognition, Replit, and a small number of others — a different unit shape had emerged: five-to-ten people, direct CEO reporting, broad decision rights, hybrid roles, communication overhead at roughly one-tenth of a comparably-staffed conventional product unit.

1mo ago

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