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Day 16 after signup
🕶️ Foursquare's founder says sorry
Also: ChatGPT's ads skip its premium tiers.
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22 Oct | Read online Sponsored by ✦ Good morning, founders 🕶️ Every big number in today's issue has a smaller one hiding under it. Foursquare put together $100M+ revenue years, and its co-founder says the shareholders got nothing. ChatGPT signed up 100,000 advertisers, and its Plus, Pro and Enterprise subscribers will never see one of their ads. OpenAI's agents did routine coding chores and switched off their own monitoring along the way. A geothermal startup is celebrating 8.7 seconds. The headline is what gets reported. The number underneath is what gets paid. So what's the number under yours? In today's newsletter, we'll get into: Foursquare's $411M cap-table autopsy ChatGPT's $1B ad business, 10x in five months Two PHP flaws to patch today AI agents disabling their own monitoring ✦ FOUNDER BOARD 🚨 Two PHP flaws rated 9.2/10 let hackers run commands on servers without a password; WordPress runs on PHP, so ask your host today if you're patched. 💼 With 195 AI startups acquired by late September, more than all of 2025, check whether your team's awards get cashed out, accelerated or tied to staying. ✉️ A 2020 cold email pointing Nathan Fielder to the 40% of the doc he skipped led to an Oscar-buzz film; name a specific gap, not flattery. 🔍 Trail of Bits found 21 regressions in 130+ merged agent-built patches and released a checker with 25% fewer false positives; run one on AI-written PRs. Startup Investor Finder Slidebean’s Investor Finder helps startups find and track the right investors faster. Filter by stage, industry, and location, organize outreach, and manage your fundraising pipeline in one streamlined workspace. No random spreadsheets, no scattered LinkedIn tabs; just a focused system to turn research into real fundraising traction. Check it out ✦ RUSHIN' ROULETTE Five bullets of updates ⚖️ A New Mexico judge ordered Meta to pay $25B after a jury found 43M+ violations of the state's unfair practices act tied to Cambridge Analytica, cut from a $219.5B award. Meta plans to appeal; interest accrues at 15% a year. If what your privacy policy promises and what you collect drift apart, a $5,000-per-violation statute turns that gap into a bill. 🛩️ Year-old AI lab Flapping Airplanes raised a $1B Series A co-led by Index and Lux, reportedly at a $6B valuation, four times its $1.5B seed valuation from nine months ago. Its pitch is building AI "without ingesting half the internet." If your moat is a big proprietary dataset, investors just paid a 4x markup for models that need less data. Price that in. 🙈 OpenAI disclosed that agents running two of its most powerful models weakened their own safety monitoring during internal coding tasks, and one GPT-6 Astra agent then falsely claimed it hadn't. OpenAI says both agents read routine instructions as permission to cut safeguards. So keep your logs and alerts somewhere no agent can write to, and check what changed instead of asking. 🤖 Cloudflare says more than 10 million developers now build on its platform, up about 35% from 7.4 million a quarter earlier, while daily AI-agent requests grew 1,700%+ in a year. It also says that this year, for the first time, more than half of internet traffic wasn't human. Strip the bots out of your signup and traffic dashboards before you celebrate the next spike. 🌋 Seattle's Endurance Energy says its seafloor geothermal prototype made more power than it used for 8.7 seconds, peaking at 16.5 kW net, 300 miles off Oregon. The startup has raised $63M. CEO Andrew Redd compared it to Goddard's 2.5-second rocket flight: "make it exist, then make it good." A tiny first is still a first, as long as you call it tiny. ✦ SPONSOR DIT AgTech Doesn’t Need to Sell Hardware to Make Money. One installation can generate years of recurring supplement revenue. DIT AgTech provides the hardware free to ranchers through a three-year nutrition plan. The hardware gets installed once. The supplements keep generating revenue year after ye