The turmoil will continue until morale improves

Top News

• Markets in turmoil: Adding to global uncertainty stemming from newly-erected trade barriers, equity prices shot higher earlier today before crashing back down when a rumor flew ‘round social media and cable channels indicating that a tariff pause could be in the offing. It wasn’t, and the stock market’s bump turned into a dump. The moment was commentary on both the market’s desperation for a return to trade normalcy, and the Wild West aspects of social media information today.

• AI all the way: In an internal memo that was released in full after being leaked, Shopify CEO Tobi Lutke announced that his company now expects its workers from the bottom to the top to experiment with, and regularly use AI tooling (see today’s TWiST500 section for more). Even more headline-grabbing, the CEO wrote that, before staffers request more human resources, they should ensure that AI agents and tools cannot fill the gap that they see in their current team makeup.

• Tech giants meet the moment: The rising trade war will rock all boats, but some sooner than others. Apple is one company greatly exposed to the new trade reality taking shape around the world. Currently, the WSJ reports, Apple intends to export more iPhones from India to compensate for higher tariffs on China. “The adjustments are a short-term stopgap while Apple attempts to win an exemption from President Trump’s tariffs,” the Journal adds, noting that the company was able to do so during the first Trump presidency. If it can manage that feat a second time is not clear — but Apple’s supply chain woes are merely indicative of the issues that many hardware-oriented tech companies are facing today.

TWiST500

Which TWiST500 company is the most prominent? The gimmies, probably. Yes, we’ve all heard of private-market stalwarts SpaceX and Stripe and Gusto and Rippling. But the biggest names could soon see another entrant into their vaunted heights: Cursor.

Anysphere, the company behind the AI coding tool, is seeing explosive growth. Recent Bloomberg reporting backs up other reports that, after reaching $100 million ARR earlier this year, Cursor has already doubled that tally. Such growth is nearly without precedent, and smells strongly of strong product-market fit.

But the bull run for Cursor may have a long ways to run yet. Bloomberg writes that the software service could find itself awash in enterprise cash in short order:

To put it in simple terms, having thousands of businesses reach out to try and give you money is insane. In a positive sense, of course. Most companies have to go grind out leads and funnels and pricing tweaks to land a single enterprise account. More than 100 per day ringing you up? It’s nearly fever-dream level bonkers for a startup.

Which is why Cursor is reportedly working on a $10 billion valuation for its next round. At first, when stacking that figure against its ARR, I was a bit perplexed. Sure, the company is growing quickly, but 50x ARR is still 50x ARR. I get it now. Enterprise account will bring with them greater ACV and stronger gross retention. To the moon, Cursor. — Alex

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This Week in Startups

E2107: On an all new TWiST, Jason and Alex discuss the chaotic response to President Trump’s new tariffs, including Klarna’s decision to delay their hotly-anticipated IPO, and they give advice to founders on how to ride out this new wave of uncertainty. Then it’s a double-dose of “Office Hours with JCal” featuring Luke Belbina from AI-powered podcast research tool PodEngine and David Moscatelli from the fast-growing fintech AI paltform, Abacus.

E2106: On today’s TWiST, Jason and Alex go DEEP on the shocking details of the Rippling vs. Deel Affair, a sordid tale of corporate espionage, scandal, betrayal, and confidential project road maps. PLUS they chat with Rabbit CEO Jesse Lyu about their latest AI “intern,” which can build entire apps from a single prompt.

E2105: Jason and Alex break down Palantir’s meme stock reality check, riff on the X/XAI merger buzz, and dig into what Circle’s IPO means for the stablecoin space. They react to Sequoia partner Andrew Reed’s inside take on fund dynamics, laugh at a brutal VC meme, and wrap with “Office Hours” featuring Caylee Harrington, founder of Hookhub — the Airbnb for RV parking — to talk van life, growth, and building in an unsexy market.

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