What’s 🔥 in Enterprise IT/VC #468

The Many Paths to $100M ARR: Understanding PLG, SLG, and BLG Tradeoffs (Plus: Varun from Clay's 3 lessons for AI founders building for enterprise)

Oct 18, 2025

Still processing the conversations from this week’s Bay area trip. Sat down with a group of founders after JP Morgan’s Tech Symposium, and the energy was electric.

One topic kept coming up: time to $100M ARR. The discussion was so good it deserves its own breakdown, especially since it builds on my post from earlier this week.

Before I dive in - quick heads up that I’ll be back out there again next week for the AI Security Summit (come join if you’re into agentic security, code security, etc.)

and doing a panel on October 22 with VC friends, hosted by Manoj Nair from Snyk.

Now, back to that $100M ARR conversation. It ties in nicely with my post from earlier in the week 👇🏻

This connects to what Bryan Kim from a16z said recently. Yes, this is the bar many multistagers want to see for Series A, but I wouldn’t overrotate to speed to ARR as your only proof of future success.

There are many paths to $100M ARR. Plenty of funds find $0-2M in 3 months compelling, while others care more about your ability to build a massive business long-term than hitting arbitrary revenue milestones quickly, especially when those milestones can be misleading (wrote more about that in What’s 🔥 #465).

What’s 🔥 in Enterprise IT/VC #465

Sep 27

Back in ZIRP land, the flex was how much you raised. Bigger round = better company (🙄). Now in the AI era, the flex is all about ARR; specifically, how fast you sprint to $100M. Way better metric, but let’s be honest: not all ARR is the same. Some are padded with pilots, contingent contracts, GMV, or one-offs. ARR ≠ ARR.

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Speaking of GTM and product going hand-in-hand, here’s Varun from Clay at OpenAI Dev Day (also at our boldstart founder dinner above) sharing his thoughts for AI founders building for the enterprise. Notice point 3 perfectly reinforces this theme:

As always, 🙏🏼 for reading and please share with your friends and colleagues!

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Scaling Startups

#💯 - one 🔑 point is to always try to save as much time as possible for discussion versus just updates

#🤔 great comments in post 👇🏻

#it’s just a bit different in SF

#🤣

Enterprise Tech

#🤯 inception round of $2B at $10B post and 6 months later on of key cofounders takes payout from Meta rumored to be $2B+, simply insane if your team is just too good, you run the risk of losing them 🤷🏻‍♂️

#it’s happening

#yes! next wave is starting as models have gotten significantly better and tools easier to use to do training, optimizing, etc

#which is why kubernetes is still not going away 😅

#can’t wait to dig into this 👇🏻

#the culture you need and how to keep building and shipping product in the AI era when growth from $1-$100M in 29 months

#the power of Answer Engine Optimization (AEO)

#💯 the future is agents understanding intent proactively

#just one data point so hard to extrapolate but…

#models not bigger but smarter

#so many of these started in 2022 and 2023 🤯

#👀

#more TradFi getting into crypto

Markets

#interesting chart from Goldman Sachs research report “The AI Spending Boom Is Not Too Big (Briggs)” - left shows number of companies and right shows market share of the market share of the leader (TSMC, Nvidia, OpenAI…)