The biggest IPO since the dot-com era lands this month. It's not a spectator sport.
Something is happening this month that will get talked about for the next decade, whichever way it goes.
OpenAI is targeting its public listing for September, reportedly seeking a valuation above $1 trillion. Anthropic is lined up behind it for October at a similar scale. Combined with SpaceX earlier this year, roughly $3.5 trillion of private valuation is walking into the public markets for the first genuine stress test of the entire AI boom.
And the tension is real. OpenAI is asking public investors to back a trillion-dollar company that's projecting a $14 billion operating loss this year. AI startups swallowed 61% of all global venture funding last year - most of it into just ten companies. Sam Altman himself has warned of bubble dynamics. So has Goldman Sachs. Nvidia is now financing its own customers. And research out of MIT found that 95% of organisations investing in generative AI are seeing zero return so far.
Maybe the market shrugs all of that off and the IPOs fly. Maybe it doesn't.
Here's my point: you don't need to know which. You're not trading this stock. But you are running a company in the economy this event reprices - because whichever way September goes, it moves your fundraising environment, your comp benchmarks, your equity story and your talent market.
Most founders will watch this month like it's television. The smart ones will position for it. Let me walk through both scenarios and what actually changes for you in each.
🚀 Scenario one: the IPOs fly
If the listings land well, the boom gets a second wind - with public market legitimacy behind it this time.
What that means for you:
AI talent gets even harder. A successful listing turns paper wealth into real wealth for thousands of employees at the big labs, and resets comp expectations across the market. If you're competing for anyone with AI in their title, the ceiling just moved. The play remains what I wrote earlier this year: stop chasing the hype titles, hire AI-literate builders who ship. That gap in price and availability gets wider, not narrower.
Equity stories start working again. A generation of candidates who watched startup equity go nowhere between 2022 and 2025 will suddenly have a fresh, giant, public proof point that it can pay off. If you've been struggling to sell options as part of your package, this is the moment that changes the conversation. Be ready to tell your equity story properly - most founders explain the mechanics and skip the meaning.
The funding bar shifts up - for AI, again. More capital chases the sector that just got validated. If you're an AI company, windows open. If you're not, the oxygen problem continues, and your fundraise leans even harder on fundamentals: revenue quality, retention, team. Which means who you've hired becomes part of your pitch.
📉 Scenario two: it wobbles
If the market balks - the IPO prices below the whisper number, or trades down hard - the correction everyone's been debating stops being theoretical.
What that means for you:
The talent market flips in your favour. A correction hits the most inflated employers first. Hiring freezes at the labs and the AI-adjacent giants release exactly the kind of people who've been unreachable - and it deflates the fantasy comp numbers that have distorted the market for two years. If August's layoff wave was a preview, this would be the feature film. The founders who kept discipline will be buying talent at sensible prices while everyone else panics.
Equity scepticism comes back hard. The same candidates who briefly believed in options again will swing the other way. Cash weighting matters more, and your equity story has to be honest, specific and grounded - not "join the rocket ship." Founders who over-promised on paper wealth will lose people. Founders who framed equity as genuine ownership with real reasoning will keep theirs.
Fundraising rewards the boring virtues. In a correction, capital doesn't disappear - it gets picky. European funds are already writing fewer, bigger cheques. That pattern accelerates, and the companies that get funded are the ones that can show real customers, real retention and a team that looks deliberately built rather than expensively assembled.
♟️ The moves that win in both scenarios
Here's what I find interesting when you lay the two futures side by side: the right moves barely change. There's a set of no-regret positions that work whichever way September goes.
Hire fundamentals, not narrative. In a boom, builders out-ship the hype hires. In a bust, builders survive the cuts. The person who can integrate, deploy and iterate with AI tools - rather than talk about them - wins in both worlds. If your hiring plan only makes sense in one scenario, it's not a plan, it's a bet.
Fix your equity story now, before the market writes it for you. Either outcome makes equity a live topic in every offer conversation this autumn. Get ahead of it. Know your numbers, know your honest case, and be able to explain what ownership actually means at your stage - in plain language, without the hand-waving.
Protect your best people through the noise. Volatility unsettles teams. Whether the headlines scream boom or bust in October, your key people will be reading them and quietly recalculating their own position. Everything I wrote in July about retention conversations applies double in a repricing month. Talk to them before the market does.
Keep your burn discipline either way. Lean-but-deliberate team building isn't a downturn tactic - it's the posture that lets you act in both scenarios. Founders with discipline get to be opportunistic. Founders without it get to be reactive.
✅ The September playbook: 3 things to do this month
1. Write your two-scenario talent plan on one page.
Left column: what you'd do in your hiring if the boom accelerates. Right column: what you'd do if the correction lands. Then look for the overlap - the moves that appear in both columns are your actual priorities for Q4. Do those now, regardless of what the market does.
2. Pressure-test your equity story with a real candidate.
Next offer conversation you have, pay attention to how your equity pitch lands. If you're getting polite nods rather than genuine questions, your story isn't working. Rewrite it in plain language: what the options are, what they could be worth in honest scenarios, and why you personally believe in the upside. Test it again.
3. Book the conversations with your three most important people.
Same list I told you to write in July. If you did it then, revisit it. If you didn't, do it now - before a volatile news month has your best people fielding calls from recruiters with fresh mandates. Ask what they're seeing, what they're thinking, and what would make their next year better than their last.
👀 What I'm seeing from my desk
Candidates are already hedging. In the last month I've noticed senior candidates asking sharper questions about runway, revenue and fundamentals - questions I used to only hear from operators who'd been burned in 2022. The market is bracing, quietly. Founders who can answer those questions with confidence are closing. Founders who bristle at them are losing people to companies that can.
The AI comp premium is holding, but the tone has changed. The numbers are still high, but candidates with AI-adjacent skills are increasingly weighting stability and seriousness over the maximum ticket. Two years ago the biggest number won. Right now, the most credible story wins. That's a genuine opening for disciplined earlier-stage companies.
Nobody I rate is waiting for October to act. The best founders I work with aren't pausing hiring to see how the IPOs land. They're using the uncertainty - moving on people while competitors hesitate, locking in key hires before the market repricing makes them more expensive or more nervous. Uncertainty rewards the decisive. It always has.
🛠️ Tools
DM me on LinkedIn with any of these and I'll send them straight over:
SCORECARD - A 5-line role scorecard template. Forces clarity on what the hire actually needs to deliver.
LOOP - A structured interview loop framework. Who interviews, what each stage tests, how to avoid asking the same thing four times.
OFFER - A checklist for making offers that stick. Comp, work model, timeline, and the soft stuff most founders forget.
Because great teams are Built Different.
Hiring question? Building a key team? Contact us - always happy to think it through with you.