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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
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The founder’s dashboard / Your quick roadmap
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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.
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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.
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𝘐𝘯 𝘮𝘢𝘬𝘪𝘯𝘨 𝘢𝘯 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘥𝘦𝘤𝘪𝘴𝘪𝘰𝘯, 𝘪𝘯𝘷𝘦𝘴𝘵𝘰𝘳𝘴 𝘮𝘶𝘴𝘵 𝘳𝘦𝘭𝘺 𝘰𝘯 𝘵𝘩𝘦𝘪𝘳 𝘰𝘸𝘯 𝘦𝘹𝘢𝘮𝘪𝘯𝘢𝘵𝘪𝘰𝘯 𝘰𝘧 𝘵𝘩𝘦 𝘪𝘴𝘴𝘶𝘦𝘳 𝘢𝘯𝘥 𝘵𝘩𝘦 𝘵𝘦𝘳𝘮𝘴 𝘰𝘧 𝘵𝘩𝘦 𝘰𝘧𝘧𝘦𝘳𝘪𝘯𝘨, 𝘪𝘯𝘤𝘭𝘶𝘥𝘪𝘯𝘨 𝘵𝘩𝘦 𝘮𝘦𝘳𝘪𝘵𝘴 𝘢𝘯𝘥 𝘳𝘪𝘴𝘬𝘴 𝘪𝘯𝘷𝘰𝘭𝘷𝘦𝘥. 𝘋𝘐𝘛 𝘈𝘨𝘛𝘦𝘤𝘩 𝘩𝘢𝘴 𝘧𝘪𝘭𝘦𝘥 𝘢 𝘍𝘰𝘳𝘮 𝘊 𝘸𝘪𝘵𝘩 𝘵𝘩𝘦 𝘚𝘦𝘤𝘶𝘳𝘪𝘵𝘪𝘦𝘴 𝘢𝘯𝘥 𝘌𝘹𝘤𝘩𝘢𝘯𝘨𝘦 𝘊𝘰𝘮𝘮𝘪𝘴𝘴𝘪𝘰𝘯 𝘪𝘯 𝘤𝘰𝘯𝘯𝘦𝘤𝘵𝘪𝘰𝘯 𝘸𝘪𝘵𝘩 𝘪𝘵𝘴 𝘰𝘧𝘧𝘦𝘳𝘪𝘯𝘨, 𝘢 𝘤𝘰𝘱𝘺 𝘰𝘧 𝘸𝘩𝘪𝘤𝘩 𝘮𝘢𝘺 𝘣𝘦 𝘰𝘣𝘵𝘢𝘪𝘯𝘦𝘥 𝘩𝘦𝘳𝘦: https://bit.ly/4bzuWCi
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STARTUP NEWS
Foursquare made $100M a year. Its shareholders got a eulogy.

Photo by Towfiqu barbhuiya on Unsplash
Most autopsies start with a company that ran out of money. This one starts with $100M+ revenue years and, by its co-founder's account, shareholders left with nothing.
Last month, ad company Infillion bought Foursquare for an undisclosed price. This week, co-founder and former CEO Dennis Crowley wrote that, going by an angel investor's post, he believes neither preferred nor common stockholders got any value from the deal. The company raised $411M+ (per PitchBook) and employed about 1,600 people over 17 years. His note to them: "I am sorry the Foursquare story ended in such a way that makes it seem like our collective efforts were worth … nothing?"
Wait, how does a $100M business pay its owners zero?
Crowley's timeline: the enterprise pivot worked. Then in 2019 a private equity firm invested, and in 2021 the banker who led that raise became CEO. Crowley blames that handoff, saying management couldn't preserve or create new value. That's his version.
The mechanics don't need a villain, though. In a sale, money is paid out in a strict order: lenders and deal costs first, then preferred stock (investor shares that get paid back first), then common stock, where founders and employees sit. Revenue isn't on that list. Neither is how much you raised. If Crowley is right that even the preferred holders came away empty, the price didn't cover what stood ahead of them.
So what's the stress test?
Every round, especially growth or PE money, stacks another layer above the common. Pull your cap table and write down three things: total liquidation preferences, any debt that gets paid first, and who can approve or block a sale. Then work out what your team's options pay if you sell for exactly what you've raised. If the answer is zero, they should hear it from you first.
Watch for former employees or investors putting real numbers on the record. Until then, the only public receipt is a heartbroken blog post.
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STARTUP TV
How to Raise Startup Funding: EVERYTHING You Need to Know
In this video, we explain everything I know about startup funding. From starting the company to Series A, B, C, D.
Slidebean is a venture-backed company. We know how this works- literally, what we do for a living is teach founders how to navigate this stuff.
But there’s a crucial thing you have to understand first, which is IF your startup can raise money.
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BIG TECH NEWS
OpenAI's $1B ad business skips its premium tiers

Photo by Kate Trysh on Unsplash
Eight months ago, ChatGPT had no ads. In March, the ad business was running at $100M a year, per CNBC. By August, it was at $1B. OpenAI says it hit that run rate in under 200 days. In late August it had about 20,000 advertisers, per The Information. As of yesterday, it has 100,000+, and ads are expanding to 26 more countries, for 89 in total.
Who's actually paying for this?
Ads show up only on the Free and low-cost Go plans. Plus, Pro and Enterprise stay ad-free. ✏️ Plus, Pro and Enterprise users buy their way out of the ads, and Free and Go users become the inventory. With OpenAI counting 1.2 billion weekly users, that's a lot of inventory.
What does the clock mean for your startup?
Every ad channel goes through the same cycle. It's cheap while advertisers are still working it out and expensive once everyone shows up. A hundred thousand advertisers against a billion-plus weekly users is still the early part. So here's your move: put a small test budget into the self-serve Ads Manager, tag AI-referral traffic separately so it doesn't disappear into "direct," and compare cost per signup with your current channels. One catch, per OpenAI's help docs: some new self-serve accounts can only advertise in their home country until identity checks clear and they've spent enough there.
The less obvious casualty is content-led growth. If buyers research in ChatGPT instead of Google, the blog post that ranked first now shares the conversation with a paid slot.
Watch Sponsored Agents next. OpenAI started testing them with some US advertisers last month. Once the agent itself can be sponsored, buying the slot next to the answer won't be enough.
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