20VC x SaaStr is Back!! Tokens Over Humans, the End of the SaaSpocalypse, and the Trillion-Dollar Land Grab

The latest 20VC roundtable with Harry Stebbings, Rory and Jason ran through nine of the biggest stories in B2B and AI right now. Anthropic filing to go public the same week it closed a $65B round. Cognition at $26B. The best public software earnings week in two years. And a budget fight that is going to redraw the org chart of every engineering team on the planet.

Here are the threads worth pulling on, with the most quotable moments from each at the end.

We Are About to Start Choosing Tokens Over Humans

The single most important number in B2B right now is the ratio of dollars spent on engineers to dollars spent on tokens. Nobody knows what it settles at yet. The whole AI market gets priced off the answer.

Run the thought experiment from Jason’s Adobe days. You manage a 400-person product and engineering org. Old world, your budget was just headcount. Everybody cost roughly $300K, office manager or staff engineer, and you didn’t think about anything else. Now you get a fixed dollar budget and a choice: keep 400 people, or go to 300 people and spend the other 100 salaries on tokens.

In 2024 you keep all 400, because you needed bodies to pick up the phone and hold the customer. In 2026, if your team will commit to even 1.5x output, the cuts are obvious and they take about ten minutes to make. The bottom of the QA list, the marginal CS roles, the inbound reps closing $3K deals. Whatever survived the first layoff wave gets cut for tokens in the second.

The data points stacking up:

• Uber is capping engineers at $1,500/month in token spend. That is ~$18K a year, roughly 10% on top of a $200K engineer. A first-pass guess at what “normal” looks like.
• The EDA software market, the most tool-heavy engineering market that exists, runs about 13% of engineering spend. That has been the historical ceiling for “tools as a fraction of engineer cost.” - Jason’s read is that for the best shops it goes well past 10%, maybe a third or more. Rory thinks that math is too aggressive. The honest answer is nobody has run a real end-to-end org at that ratio yet.
• The startups are already there. Brandon at McCor says they now spend more on tokens than on engineering salaries with ~80 engineers. The conceit in those stories is the headcount. 80 is not 1,200.

The reason this matters for valuations: you can get to the Anthropic and OpenAI growth curves on even a 10% allocation across corporate America. At 33%, you buy the IPO at any price, and you also watch one in three or one in four roles across the product and engineering stack get replaced.

SaaStr already made the call. We got rid of the B players and would rather have tokens. The bet only works if your VP of Engineering can actually ship product, not just pull requests, with that level of cut. The faster a company is growing, the more they tell you yes. The slower it grows, the more they tell you it can’t be done.

Founder takeaway: Start measuring your token spend as a percentage of fully loaded engineering cost now. That number is your single best leading indicator for where your headcount lands in 2027.

Anthropic Files to IPO, and the “Billion-Dollar Position” Bar Resets

Anthropic raised $65B and filed to go public in the same week. ARR is up 28% since the prior episode. It is on track to be the fastest company ever to IPO anywhere near its scale, and SpaceX is formalizing at $1.75T for early June.

When the best company of the decade goes from zero to a trillion in five years, it warps the whole bar. Jason’s version of the reset: he won’t take a meeting now that he would have taken in 2024. Not because the founders aren’t good or the companies aren’t real. The bar for a position just moved. His new line is that he is not interested unless it can be a billion-dollar position, not a billion-dollar outcome.

The distinction matters. A billion-dollar outcome can happen with a pretty-good CTO, a mid-size TAM, and some luck. A billion-dollar position requires you to underwrite ownership times a much bigger number. So the screen becomes: are there tangible blockers? An A-minus CTO who won’t launch 17 products at once. A small TAM with no real path to a large one. Complainers. Those are blockers, and now they’re a fast no.

Rory’s pushback is the base rates. In a normal year there are maybe four or five $10B-plus software outcomes total, and one to three $100B-plus outcomes per decade. You cannot make 20 to 30 seed or Series A bets and credibly believe each one is a billion-dollar personal position. So he underwrites to a realistic base case and never caps the upside. Same place, different math.

Where they fully agree: the floor for “aspirational enough” has gone up. People have now seen what 10x growth for three years actually looks like, and that anchors everyone. Founders who pitch below that line read as boring, even when the business is healthy.

Founder takeaway: The grandiosity-versus-credibility band has shifted up. You need a credible upside story that gets to a real position, told without sounding delusional. The cost of pitching “solid but capped” is a faster no than it was a year ago.

The Trillion-Dollar Land Grab: Everyone Is Rushing the Public Markets at Once

The stay-private era is over. Google announced an $80B equity raise, its largest in a very long time. SpaceX priced at $1.75T. Anthropic and OpenAI both pointed at roughly October. Add it up across those names and you get $300B to $400B of equity issuance, nearly all of it AI-related.

The framing that fits: it’s like an airline gate in a country with no orderly queue. The door opens and it’s a mad rush to board. Smart boards all looked up at the same time, saw the scale of capital required, and decided to jostle to the front. Google grabbed the first $80B. Why issue equity when you’re the second most profitable company on earth and could borrow? Because the stock is high, equity is cheap at an all-time premium, and a strong balance sheet insulates you from the micro-panics in the debt markets. You can also do both, layering debt on top.

The deeper signal is the business-model shift underneath all of it. These companies have gone from capex-light cash-flow machines to capex-heavy cash-consumptive machines. Across history, things that spin out cash are great investments and things that eat money are usually bad ones. On a trailing basis the numbers still look incredible. The forward picture is the open question.

Founder takeaway: When the best-capitalized companies in the world are all raising at once, the message is that the capital required to compete just went up an order of magnitude. Plan your own raise timing accordingly.

Is the SaaSpocalypse Over?

Best public software earnings week in two years. Salesforce, Snowflake, MongoDB all delivered and the stocks surged. The WCLD cloud ETF was down ~30% a month ago and has round-tripped 25 to 30% back. The catch: that only gets it back to flat on the year. For most of the last month software actually outperformed semis, but for the full year semis have murdered software to the upside because software just clawed back to even.

The rule that held up: you either reaccelerate or you attach to AI spend, and the winners did both. The losers with messy stories went down.

The clearest pattern is the split between software agents use and software only humans use:

• Twilio is up ~57% this year, growth gone from 4 to 5% back to ~20%, because agents and AI need more voice and messaging.
• Okta is up ~56%, because everyone doing identity is blowing up.
• Datadog is up ~100%, because every AI leader runs on it.

The human-per-seat model is dying. Not dead, but nobody wants to buy another seat for a person who doesn’t do work in your project management tool, and they’re actively cutting those seats to fund tokens. Gartner has AI software spend up 60% this year, which has to come out of somewhere.

Even Salesforce, which reaccelerated through Agentforce and hard work, told a similar story of shifting to agent-based pricing.