What’s 🔥 in Enterprise IT/VC #452

AI Native vs. Incumbent - speed to distribution vs. speed to innovation and when ZIRP-era 🦄 should just go all in on AI

👇🏼 this…

and this ties in so well with this chart from Iconiq’s State of AI 2025 Report

Notice the blue highlight:

This begs the question whether AI-native orgs may be structurally better equipped - through team composition, infrastructure, or funding models - to validate product-market fit and scale effectively, and perhaps leapfrogging the trial-and-error phases that slow down AI-enabled companies retrofitting AI into existing workflows.

While there are so many examples of AI Native cos going from $1-50-100M in a short period of time, what we don’t know is how durable all of this growth is. Only time will tell.

Everyone’s building the same thing

One other super imporant dynamic to understand is that everyone seems to be building the same thing. So as always it will ultimately come down to execution.

IMO what’s important is not to just add AI, but first to rethink and reimagine a workflow or process before just throwing AI on top. Think out of the box, is there a better way to do this, or what will that better way look like as AI gets better? Reimagining is a must have!

Going all in on the pivot to AI

Even Airtable, a company with $400M of ARR and a last round valuation of $11.7B, made a super bold move and pivoted the whole company to becoming yet another AI app builder like bolt.new, replit, bolt.new, you name it…, but built to be production ready out of the gate. Gergely shares this thoughts, and I chime in below.

Notice that Coatue matrix attached - thoughts on how ZIRP era 🦄 can think about their current state of play - if you’re growing <25% and not profitble, well reinvent. Seems like Airtable just did that playbook, and the tool is pretty darn powerful so hope they succeed and inspire and lead the way for others!

Go Big or Go Home!

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

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Scaling Startups

#💯

which is why we’ve had it as one of our taglines all along…

#sign of the times - all about Inception - the race to be first! Still called a Series A but not what it used to be…

More on why everyone is in the race to be first from What’s 🔥 #365

#RIP Fred Smith FedEx - this is a founder fully embodied

#that’s what I call a Jumbo Inception Round - want to raise $2B on just your brains alone?

#for the VC readers…

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Enterprise Tech

#must read Iconiq State of AI 2025 Report which I referenced earlier - for the builders and enterprise software vendors to see how far along your peers are, what concerns them, and what tools they’re using - here are a few slides

#💪🏻 context is king and finding that magical balance between too much and too little context can result in dramatically different output and cost...

#a world of hurt coming our way on the security side as hackins is RLable…for those who don’t know, RL is reinforment learning which is a type of machine learning where an agent learns to make decisions by interacting with an environment, receiving rewards or penalties based on its actions, and optimizing its behavior to maximize cumulative reward over time.

#❤️ this from Mitchell Hashimoto, cofounder of Hashicorp - how he won agains the hyperscalers, how to make them care as a partner, and who was the best as he built it into an IPO and $6.8B exit to IBM - some amazing lessons and deep, hard-earned insight

#how Meta will compete with OpenAI and others - focus on entertainment, connection with friends, on how people live their lives…

#💯 on the road to the autonomous enterprise, humans in the loop will continue to be in the background - coordinating workflows, etc - the last 10% requires a lot of work

#the new role at many a company - automation engineer

#the future is limitless?

#A2A agent interoperability will know be an open standard - buzz has been building for sure and enterprises that I’ve spoken with all ask about it - just so you know this includes AWS, Google, Microsoft, Salesforce, SAP and Servicenow!

#another overnight success…

#💯 last mile hardest, all about delivery…not the models

#great overview from Andreas on what’s happening in European tech now

#even if you don’t code, you should read this to understand how to interact with AI to get your best work output

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Markets

#fast follow ons keep coming at late stage - Abridge (WSJ)

Abridge, a startup that has automated doctors’ note-taking with artificial intelligence, on Tuesday said it had raised $300 million in funding.

The round, led by venture-capital firm Andreessen Horowitz with participation from Khosla Ventures, values the startup at $5.3 billion. In February, Abridge raised $250 million at a valuation of $2.75 billion.

Four months after a $3B valuation, Harvey AI grows to $5B (TechCrunch)

Harvey AI, a startup that provides automation for legal work, has raised $300 million in Series E funding at a $5 billion valuation, the company told Fortune. The round was co-led by Kleiner Perkins and Coatue, with participation from existing investors, including Conviction, Elad Gil, OpenAI Startup Fund, and Sequoia.

#the power law in the public markets