What’s 🔥 in Enterprise IT/VC #449
$8.3M ARR per head for an enterprise startup 🤯 (Anysphere) + the rising confidence in how to build lean and run fast
Writing this from 30,000 feet ✈️ on my way to Europe for a board meeting, founder pitches, and a super cool AI summit — one recurring thought keeps surfacing: the entire startup playbook continues to be reinvented in real time.
That came into sharp focus during a dinner last week with 8 of our Boldstart founders, a seasoned group, many with prior exits or multiple startups under their belt. When the conversation turned to company building, the only real consensus was this: teams are moving 10x faster than in past eras and staying lean well into revenue scale.
That may not be a shocking insight, but the conviction behind it was.
Of course, not everything is settled. There were differing views on remote vs. in-person (I’m still firmly in the “in-person if you can” camp), but agreement that SF continues to matter, whether you’re based there or just need to be in the mix. And while AI helps teams do more with less, the human element is only becoming more important. You need sharper, more adaptable hires — not just in engineering, but across GTM who can effectively manage and direct agents.
And if you’re running lean, every single hire counts. The quality bar rises. We all agreed: in a world where buyers are flooded with AI-generated outreach, real human relationships, especially in enterprise sales, are becoming more critical than ever. Steak 🥩 dinnahs continue to deliver results 🤣.
To ground the discussion, I asked:
“How many people do you actually need to hit $1M, $5M, and $10M ARR — and how does that compare to what you thought a year ago?”
No surprise, the answers varied by product and ICP. But what stood out was how many founders CONFIDENTLY felt they could get from $1M to $5M ARR with almost no additional headcount beyond their initial eng/product team and a few GTM hires. We’re talking 5–10 people for some founders and upwards of 15-20 for others, but regardless, a huge change from the ZIRP era.
Hitting $10M+ ARR is another phase; support, onboarding, enterprise sales, but even then, most believed they’d need fewer people than they would’ve guessed a year ago. That shift is driven not just by the rapid evolution of AI and their experience building as AI native startups, but more imortantly inspiration drawn from this new wave of AI-native startups scaling at incredible speed.
It’s a mindset and CONFIDENCE shift we’re also seeing in how companies like Zapier are rethinking their org design and hiring for AI fluency across the board (👇🏻 to see how Wade Foster’s qualifying for this).
And if there’s one company that embodies this new model, it’s Anysphere, creators of Cursor.
They just raised $900M at a $9.9B valuation, but the growth behind that number is what’s truly mind-blowing 🤯 (more from Bloomberg):
Fastest growing startup ever to hit $100M ARR — in just 14 months (January 2025)
5x growth in 4 months — now at $500M ARR (May 2025)
50%+ of the Fortune 500 are using Cursor
1M+ daily users
60 employees → $8.3M ARR per person
First sales hires came after product-market fit — now enterprise is a major driver
Now ask yourself: if someone pitched you on a coding assistant that requires devs to switch IDEs, going head-to-head with GitHub — which had an 18-month head start, massive distribution, and deep moats — would you have said yes?
Probably not. And fun fact, Cursor was actually a pivot as early investors backed the founding team, and not this idea. However you still get the point!
This is what happens when you build with taste, move fast, iterate relentlessly, and, as Guillermo from Vercel says, the product is just awesome.
So stay open. Keep learning. And don’t be afraid to write your own playbook especially in a world where everything is changing so fast.
🙏🏻 Thanks for reading — and as always, feel free to share with friends and colleagues.
Scaling Startups
#huge jump - makes sense as % of seed to Series A 📉 and more seed stage startups looking to sell earlier - massive leap from 2019 and 2020…(from SVB State of Enterprise Report)
#💯
#stupid enough to believe an idea others did not and crazy and resilient enough to keep going in face of the criticism - great interview with founder/CEO of Blockdaemon, a leading blockchain infrastructure company helping institutions connect to Web3 (full disclosure - i’m on board and my firm boldstart is an investor) - many words of wisdom surviving tough times
#❤️ this, h/t Sam Lessin - Jeremy Liew on how much impact VC board members can have - 30% positive or negative - IMO it can be 100% negative, 3x as exec, and 30X as founder - choose your partner wisely!
Enterprise Tech
#What is taste? Taste is a deep felt point of view from founder on what should exist and why, first manifests itself in product point of view and down to each feature and pixel where every single detail matters, becomes pare of core DNA of product, company, and team - becomes a moat in most competitive of markets where any one can ship a similar version - great post from Sara at Convisction 👇🏻
#speaking of Vercel - ARR doubled to $200m in 15 mos 📈 with hot AI customers like Decagon, Granola, Runway and others (The Information)
#usually don’t share much on consumer but since so many bottoms up consumer products have led to enterprise sales, check out 🔑 learnings summary from a16z on what best consumer AI cos have done
#the new new thing for VCs - great news you can write massive checks to buy services firms to try to AI-enable them but agree here with Kwak - requires a shit ton of work, culture changes and different skill set than most growth VCs are set to handle (👇🏻 click for some great comments)
#not surprising given Windsurf being bought by OpenAI but alliances/battle line being drawn…tough when Windsurf and Claude was powerful combo
#Morgan Stanley building its own coding assistant for legacy to modern code conversion (WSJ) - claims already has saved devs 280,000 hours!
#💪🏻 Crowdstrike’s famous platform slides shows the point vendors its aiming to replace! (via Cyburger) - good news for thoe smaller cos - great o e on the list as you’re big enough to be a target!
#if you’re wondering why some of these rounds are beyond comprehension, winning means amassing and retaining the best talent and the price keeps going up 📈
#robotics biggest opportunity ahead and implications if US leads and if not? Worth 4 mins of your time 👇🏻
#early look at some YC W25 cos before next week’s demo day from Stealth Startup Spy #243
#fully automated ads by end of 2026 🤯
#we will all become managers…of dozens upon dozens of agents - the nature of what we do is changing rapidly
#here’s Perplexity’s new deep research tool - can’t tell if 100% accurate but you get the gist - hours upon hours of work well done with a prompt and can be parallelized - 👇🏻 click and watch
#🤯 not surprising then that Anthropic's annualized revenue jumps from $1B to $3B in five months driven!
#And OpenAI enterprise customers also growing at a rapid clip adding 1m new enterprsie customers in 3 months! 😲 (WSJ)
In the interview, Lightcap also said that OpenAI’s enterprise customers have grown to three million, up from two million in February.
“We are growing quite fast in enterprise,” Lightcap said. He said the company is working with the California State University System and will make it available to about 500,000 students and faculty. He called it the “first AI-powered university system” in the country.#more on moats - yes, you get the picture - speed matters (👇🏻 click for clip)
#our tokenized future is coming for all assets and Larry Fink at Blackrock driving this - lots of opportunity to provide infra (hello Blockdaemon), security and more to enable this - worth a 1min watch 👇🏻
Markets
#crypto is back in a big way and don’t discount what the TradFi (traditional finance) folks will do as stablecoins proliferate with real world use cases like cheap, seamliness, instant international payment settlements and more like Larry Fink’s vision of tokenizing all securities - pay attention!
#will the big IPO unlock happen as VCs accept down rounds? (Axios)
I know you are crazy busy but I appreciate you take time to assemble this every week. Thanks!