Damian Pickett · No. 11
Monday 14 September 2026
iOS 27 rolls out today, and it’s the biggest change to Apple’s notifications in 15 years.
iOS 27, rolling out today, replaces the chronological Notification Center that has existed since iOS 5 in 2011. It is Apple’s biggest change yet to how iPhone and iPad surface alerts.
Perplexity now lets OpenAI’s newest model write communications, change software and monitor production systems with far less human check-in than earlier models needed, a real test of agentic AI at work.
Erivo, already twice Oscar-nominated and a Tony winner, drew a standing ovation in Toronto for her role as a lawyer in Prima Facie, based on Suzie Miller’s award-winning play.
Read · Lenny's Newsletter
10 years, 300 companies, 4 non-obvious lessons on getting past the trickiest roadblocks
Ten years and 300 companies of positioning lessons, straight in Damian’s product-marketing lane.
Listen · Founders
Senra’s principles from the great 19th-century merchant banking dynasties, the reputation-first playbook behind today’s positioning read.
Listen · David Senra
Bending Spoons’ co-founder on extreme ownership and hiring raw talent, exactly the operator profile Damian studies.
Listen · Acquired
Two founders fired and broke, rebuilding into a $30 billion company: the founder mythology Damian loves from Acquired.
Simon Willison built a small web app to clean up commit messages for his Datasette security releases after coding-agent cruft crept into the originals. A tidy, useful fix for a problem AI coding tools create.
Willison’s screenshot automation tool now supports WebP output, letting users capture web pages in a smaller, modern image format from the command line.
TechCrunch’s Equity podcast digs into the AI industry’s renewed debate over whether the technology poses an existential threat, and why the warnings are growing louder now.
VCs picked their favourite companies from YC’s summer batch, ranging from floating nuclear reactors to brain chips, a snapshot of where early-stage investors see the next big product.
Tesla has set an October 10 reveal date for the long-delayed second-generation Roadster, first shown in prototype form back in 2017.
Fusion startups are striking defence-related deals, reviving a relationship between fusion research and national security that had gone quiet but never fully disappeared.
This week’s Mobility roundup covers Lyft’s move into robotaxis, part of a wider shift in how ride-hailing companies are building around autonomous driving.
iOS 27 arrives today with Apple’s more advanced Siri AI capabilities among other refinements, rolling out region by region from around 10am Pacific.
Apple’s software engineering chief spoke to MKBHD about where the new iPhone Duo sits next to the iPad, a week after both launched at Apple’s event.
Bloomberg reports Apple is preparing to overhaul its retail stores, including bringing back dedicated Genius Bars, a reversal of the more open floor layouts introduced years ago.
Bloomberg’s Mark Gurman reports Apple is designing two game controllers for iPhone, likely under the Beats brand, corroborating references found earlier in macOS beta code. This is a report, not a confirmed product.
Rogen was honoured alongside Helen Mirren, Penelope Cruz and Isabelle Huppert at TIFF’s Tribute Awards, a surprise recognition for the 44-year-old.
Variety calls this age-gap romcom, named after the 1992 Ace of Base hit, a fizzy showcase for Murphy in her first leading feature role.
After years in the DC universe, Snyder returns with a jungle-set action thriller that Deadline’s TIFF review finds more grounded and human than expected.
Marie Clements’ TIFF film examines hidden and violent aspects of recent Indigenous history through a personal, magical-realist lens, per IndieWire’s review.
Most of the surviving cast of the late-1980s western gathered in Dallas this weekend, a nostalgic reunion for one of the era’s defining ensemble films.
Brown is expected to miss around six weeks with an ankle sprain, no surgery planned, a real blow after New England’s Week 1 loss to Seattle.
Albert Breer reports a ‘respected’ team enquired about trading for Hollins over Kayshon Boutte, but New England is not interested in moving him.
Kimi Antonelli won the Spanish Grand Prix, his eighth of the season, after Lando Norris lost a likely victory to the bad timing of a virtual safety car.
Norris wants Formula 1 to change its virtual safety car rules after they cost him victory at the inaugural Spanish Grand Prix in Madrid.
Hamilton suffered a brake failure early in the Spanish Grand Prix while battling Max Verstappen, and says he was lucky to get back to the garage safely.
Rookie Payton Tolle threw the eighth immaculate inning in Red Sox history, and the sixth immaculate first inning in MLB history, in a win over Kansas City.
Willson Contreras was activated from the injured list and made an immediate impact back in the Red Sox lineup.
Ranger Suarez struck out eight in another strong outing against the Royals, crediting a mechanical adjustment after a rough August.
A cross-shaped timber holiday home stretches into a forested, north-facing slope in southern Sweden, a quiet piece of craft to close the day on.
