AI builder in San Francisco
San Francisco
Joined December 2014
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Gil Pignol retweeted
The New Kingmakers
It's become clear that revenue scale no longer matters - or is correlated - with raising a round. It's important but not sufficient.
Besides team caliber, what ACTUALLY matters to fundraising is how many top AI-native companies use your products, love your products, embrace your products and profess undying loyalty to you (i.e. say they won't replace it at the drop of a hat).
Why?
AI-native companies are the hardest customers to win. They have the engineers to build it themselves. They have the taste to know when something is mediocre. They try every new tool the week it launches and rip it out the week after. If one of them pays you and stays, your product survived the toughest evaluation there is. Investors know this.
Revenue can be bought. Pilots, services, discounts, a heroic enterprise sales team. ARR built from Fortune 500 pilots proves you can sell. The product might still be mediocre. Loyalty from a kingmaker can't be manufactured.
These companies are the leading indicator. Investors are underwriting where the market will be in 5 years, and the AI-native companies are already living there. Their workflows today are everyone else's workflows in 2029. If they picked you, you've been chosen by the buyers everyone else will copy.
The last reason is distribution. Kingmakers talk. Their engineers post what they use. Their founders compare notes. One of them begets the next three.
Who
There are probably ~50 AI-native companies that are perceived as kingmakers for startups. I've seen $50M+ rounds raised on the backs of just having one of these as a customer. (not pilot, but actual paying customer using the product as a core part of their infra and workflows).
Meanwhile, I see early-stage founders spending 12 months chasing CVS, Walmart, and Pfizer. Long procurement cycles, security reviews, a pilot that never converts. Even when it lands, the logo proves you can survive procurement. That's the wrong thing to prove in 2026.
If you're an early stage enterprise/B2B AI company, Instead of targeting CVS, Walmart, Pfizer, etc, go after the companies on Forbes' AI 50 list.
The new milestone is kingmaker logos. That's what your next round will be priced on.
Gil Pignol retweeted
Ben Thompson:
"I think Muse is good enough — and the overall agent experience impactful enough — that this will be the test of AI in the consumer space: if this doesn’t take off glorified search might be as far as we get....
Human scale, with computers, instead of computer scale, in place of humans."
Gil Pignol retweeted
Wow. Airtable, founded in 2012 and once valued at $11.7B, is getting acquired by Bending Spoons, founded 2013, at 2.7x ARR.
A once hot startup; now an unfortunate victim of the SaaS bust. It raised $1.4B only to be sold for $1.285B EV ($2.25B equity value), just clearing its preference stack.
That implies common and early holders split the remaining ~$850M, a ~10x haircut from peak.
“What both Microsoft and Netscape missed out on was that realization that the browser didn’t really matter. It was sites that mattered. We easily could have bought Yahoo, Google, etc.”
- Jon Mittelhauser
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The AI app layer is truly exciting
The labs are like Netscape in the 1990s
The websites ended up being the thing, not the browser
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GTM is hard
"GTM iS EaSY"
GTM:
> turn off open tracking
> no link in the first email, ever
> never send from your root domain
> verify emails at send, not at import
> 30 sends a day per mailbox, no more
> plain text, no images, no tracking pixels
> score positive replies, not total replies
> waterfall three data providers, never trust one
> enrich your tier one accounts, not the whole list
> use local data providers for emea and apac lists
> don't discard catch-alls, score them and send anyway
> track headcount deltas by department, not by company
> filter the list by mx record before you write any copy
> funding rounds are the most spammed signal in outbound
> 300 contacts per variant or you are just reading noise
> a first sales ops hire beats a series b as a trigger
> rebuild the list monthly, a third of titles rot every year
> a job post naming your competitor is a displacement signal
> read their job posts for the tech stack, it beats builtwith
> two customers asking for the same integration is a channel
> ai personalization on a bad list only amplifies the bad list
> write the first email to be forwarded down, not read at the top
> champion job changes are your warmest list and they cost nothing
> target whoever owns the pain, then ask them who owns the budget
> measure at meetings held, everything upstream of that is a proxy
> a new vp has 90 days to swap vendors, that window is your campaign
> soc2 on their trust center means they just started selling upmarket
> export closed-won, enrich it, and find the three attributes every account shares that your icp doc never mentions
> find where the champions from your last 20 lost deals work now, and open with the workflow you already know they run
> pull your competitor's sitemap, grab /customers and /case-studies, enrich every logo you find, that's the best list you'll ever build
> scrape every job post that names your competitor, filter to the last 30 days, and send the displacement email to the hiring manager, not the recruiter
> take your churned power users, find their new employers, and open with the exact workflow they used to run, nobody else hitting their inbox knows that
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Goal seeking agents going rogue on Google Drive. Careful what you wish for!
So I’m building an app called SaaStr Connect
The other day, Claude Fable went into my Google Drive without me knowing or asking, and saw a draft document I’d written … “Jason’s Gems”
It was ideas for improvements to the Connect app, but just brainstorming in a Google Doc. Early stuff.
Fable then decided without telling me to take those ideas, log in to my app via the Replit MCP, and to tell the Replit agent to change my app and implement those changes … without ever telling me. I never knew.
I only found the changes when I saw other changes the Replit agent was making later, and it noted conflicts with “Jason’s Gems”. What??
Agents will goal seek. In ways we can’t entirely foresee.
Fable just decided autonomously to change my app on its own, without me knowing, when it saw draft ideas in my Google Drive I didn’t ask it to look at, by logging into another app to make the changes without me knowing.
All good in the end. But need to be mindful.
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Why can't #Fable code this and release it to the world?
I’m so excited that @JensenHuang is a believer in open source now, looking forward to the CUDA and GPU driver open source release!
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How the US wins the AI race
For my first post, I’m sharing a letter @NVIDIA signed on why open models matter.
AI will transform every industry, power every company, and be built by every country.
Open models strengthen safety and cybersecurity, accelerate innovation and diffusion, and enable sovereignty.
The world needs both frontier closed models and frontier open models.
images.nvidia.com/pdf/Open-W…
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Thiel is right about the Lean Startup:
It’s not about abandoning the method. It’s about choosing moments where you reject the data and bet on the myth.
Peter Thiel on what he doesn’t like about the Lean Startup
Thiel believes there are merits to the Lean Startup, but he thinks founders today may have over-indexed on it:
“I do think we tend to be dominated by a somewhat nihilistic bias where we claim not to know anything. And when you don’t know anything, you end up defaulting too much to the experimental search, A/B testing approach of ‘Let’s ask the customers.’ And I would say the problem with that is that the search space is simply way too big.”
In practice, Thiel argues for a more definite view of the future: “This is an important problem that needs to be solved, and this is the set of things we have to combine in just this way to do it.”
To be fair, Steve Blank—who pioneered the Lean Startup methodology—isn’t necessarily against this approach. Blank just recommends treating your assumptions as “a series of untested hypotheses.”
But there’s clearly a balance between having a definite view of the future and rigorously trying to disprove your assumptions.
As Thiel explains, many of the PayPal founding team’s initial assumptions were wrong:
“At PayPal, our original business plan was to have payments on Palm Pilots, then it was wireless payments, then it was payments linked to email. So we had a few fairly big pivots in the first year. I’m not sure there’s anything especially virtuous about that — if you have a dumb idea, it’s important to change it — but it’s not virtuous to have a really bad idea in the first place.”
Source: @OxfordSBS (May 2015)
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New article about how Nolan's Odyssey is not about Homer 👇
Gods turned into weather, polytropos into Everyman, shame into trauma, epic into recovery
medium.com/@gp2030/the-odyss…
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Great negotiation tips from Uber's Travis Kalanick
But the fundamental problem is to have the hottest deal of the year in Silicon Valley 😅
fundraising masterclass from @travisk
on valuation: "I'm always saying it's at least this and it can go up, but I start low... so it only goes up, so that everybody's pumped, leaning forward"
start low, get bid up. anchoring initial price too high is a rookie mistake
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