What’s 🔥 in Enterprise IT/VC #441

Words of advice from Jamie Dimon JPM, Andy Jassy Amazon, Tobi Lutke Shopify - cash is king 👑, move fast, kill layers of bureacracy, invest in AI

There’s a saying in the Caribbean, if you don’t like the weather, wait five minutes. We can equally apply that same logic to the current administration’s tariff policies and the massive swings in the market. If you’re a founder, all I can say is that the longer this goes, the harder it will be to undo the damage, and where there is uncertainty, people and companies spend less. The only good news is that we have AI and agents, and this environment could prove to be an accelerant to adoption. Given all of this uncertainty, what better way to prepare for what’s ahead than soaking in some words of wisdom from the annual letters of top CEOs like Jamie Dimon at JPM, Tobi Lutke at Shopify, and Andy Jassy at Amazon.

Here’s the current state of play from Jamie Dimon at JPM - note, IT IS PRUDENT TO MAINTAIN EXCESS CAPITAL AND AMPLE LIQUIDITY IN THIS ENVIRONMENT. In other words, cash is king 👑 (read last week’s What’s Hot #440 for the recession playbook).

I went on to read Jamie’s annual letter and extracted some words of wisdom for all of you. Most importantly, I found his management section quite powerful for these times where he stressed the importance of efficiency, killing bureacracy, and doing more with less.

Speed Matters

Kill Complacency - the world is moving faster than ever

Tobi Lutke from Shopify echoed many of these same sentiments in a company wide letter to all employees but added an additional twist - think AI first in every single thing that you do culmintating in asking for more headcount only if you can show that AI can’t do it for you 🤖! I encourage you to read this as it applies to any sized company with clear specific examples of how to implement this thinking. Bottom line, if you aren’t AI first and AI native in thinking, building and execution, you’re not long of this world!

Excerpts from memo below which you can read in full at here and the new X post.

AI usage is now a baseline expectation

Reflexive AI usage is now a baseline expectation at Shopify

It’s the most rapid shift to how work is done that I’ve seen in my career and I’ve been pretty clear about my enthusiasm for it: you've heard me talk about AI in weekly videos, podcasts, town halls, and… Summit! 

What we have learned so far is that using AI well is a skill that needs to be carefully learned by… using it a lot. It’s just too unlike everything else. The call to tinker with it was the right one, but it was too much of a suggestion. This is what I want to change here today. We also learned that, as opposed to most tools, AI acts as a multiplier.  We are all lucky to work with some amazing colleagues, the kind who contribute 10X of what was previously thought possible. It’s my favorite thing about this company. And what’s even more amazing is that, for the first time, we see the tools become 10X themselves. I’ve seen many of these people approach implausible tasks, ones we wouldn’t even have chosen to tackle before, with reflexive and brilliant usage of AI to get 100X the work done.

What This Means
1. Using AI effectively is now a fundamental expectation of everyone at Shopify. It's a tool of all trades today, and will only grow in importance. Frankly, I don't think it's feasible to opt out of learning the skill of applying AI in your craft; you are welcome to try, but I want to be honest I cannot see this working out today, and definitely not tomorrow. Stagnation is almost certain, and stagnation is slow-motion failure. If you're not climbing, you're sliding.

2. AI must be part of your GSD Prototype phase. The prototype phase of any GSD project should be dominated by AI exploration. Prototypes are meant for learning and creating information. AI dramatically accelerates this process. You can learn to produce something that other team mates can look at, use, and reason about in a fraction of the time it used to take.

3. We will add AI usage questions to our performance and peer review questionnaire. Learning to use AI well is an unobvious skill. My sense is that a lot of people give up after writing a prompt and not getting the ideal thing back immediately. Learning to prompt and load context is important, and getting peers to provide feedback on how this is going will be valuable.

4. Learning is self directed, but share what you learned. You have access to as much of the cutting edge AI tools as possible.There is chat.shopify.io, which we had for years now. Developers have proxy, Copilot, Cursor, Claude code, all pre-tooled and ready to go. We’ll learn and adapt together as a team. We’ll be sharing Ws (and Ls!) with each other as we experiment with new AI capabilities, and we’ll dedicate time to AI integration in our monthly business reviews and product development cycles. Slack and Vault have lots of places where people share prompts that they developed, like #revenue-ai-use-cases and #ai-centaurs.

5. Before asking for more Headcount and resources, teams must demonstrate why they cannot get what they want done using AI. What would this area look like if autonomous AI agents were already part of the team? This question can lead to really fun discussions and projects.

6. Everyone means everyone. This applies to all of us—including me and the executive team.

The Path Forward
AI will totally change Shopify, our work, and the rest of our lives. We're all in on this! 

Our job is to figure out what entrepreneurship looks like in a world where AI is universally available. And I intend for us to do the best possible job of that, and to do that I need everyone’s help. I already laid out a lot of the AI projects in the themes this year- our roadmap is clear, and our product will better match our mission. What we need to succeed is our collective sum total skill and ambition at applying our craft, multiplied by AI, for the benefit of our merchants.

-tobi
CEO Shopify

Finally, here’s Andy Jassy’s letter and some of his comments on culture and speed and removing bureaucracy - do you notice a theme 🤣?

And here’s Why on AI - 1000 apps being built = amazing customer experiences and efficency!

To reiterate:

But in periods, like now, of unusually high demand (our AI revenue is growing at triple digit YoY percentages and represents a multi-billion-dollar annual revenue run rate), you’re deploying a lot of capital. We continue to believe AI is a once-in-a-lifetime reinvention of everything we know, the demand is unlike anything we’ve seen before, and our customers, shareholders, and business will be well-served by our investing aggressively now.

So you get the picture - cash is king, move fast, kill layers of bureacracy, invest in AI and then…there’s cybersecurity. Here’s Jamie Dimon from JPM:

Which is why Morgan Stanley’s latest CIO survey shows AI and cybersecurity are the most resilient categories for IT spend.

So yeah, it’s a shitstorm coming ahead, but as always there will be pockets of opportunity! And if you’re on the fence about becoming an AI Native company vs. a bolt on AI company, read this inspiring post from Daniel Koch, VP Engineering at Jit Security, a portfolio co, AI agents for AppSec.

We got this!

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

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Scaling Startups

#simple but so true

#want happiness? 💯

#Q1 data from Pete Walker Carta - “Seeing seed rounds hit $20M post-money as a MEDIAN is pretty wild. That's higher than any point in 2021.”

#There is AI in Miami 🌴 - great gathering last Saturday led by portfolio co CrewAI! Click below for some of the slides on agentic use cases - thousands of them in production already!

#next level capital 🤯 (Reuters)

Venture capital firm Andreessen Horowitz is seeking to raise about $20 billion in what will be the largest fund in its history, to capitalize on global investors' interest in backing U.S. artificial intelligence companies, sources told Reuters.

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Enterprise Tech

# Google crushed it at Cloud Next with a number of new offerings - here’s what was top of mind for me

Universal agent interoperability

A2A allows agents to communicate, discover each other’s capabilities, negotiate tasks, and collaborate even if built on different platforms. This enables complex enterprise workflows to be handled by a team of specialized agents.

A2A - huge unlock bringing true interoperability and perhaps a new security attack vector as well!

Going after Lovable and Bolt with a deployable app 😲 - click and read the 🧵

#in case you’re wondering what does Google’s new proposed standard A2A really does and why we may need that and MCP, here you go 🧵

#what tariffs or recession? This is quite an Inception round 🤯! $2 Billion!

#top SaaS vendors on Ramp April 2025 report - wowza on biggest % change - all vibe coding and AI!

#from the founder of Hashicorp - he’s saying a couple things which we can all agree on - AI is a must have but not sufficient nor is it a moat - it gets you in the door but you have to backfill with strong capabilities besides AI - we get that but nice to be reminded

#we can never get enough of Steve Ballmer doing this - Developers, Developers, Developers! (h/t Tom Warren)

#machine discovery whether via LLMs or MCP going to be huge in future…

#Securing agents, MCP servers - new attack vectors with lots of incumbents and VC’s pouring in 💰

#🔥 up for RSA - here’s this years list of Top 10 Finalists with an interesting twist - they all get a $5M SAFE as a finalist! Congrats to boldstart portfolio co Smallstep and founder Mike Malone. Smallstep recently introduced the world’s first Device Identity Platform™ to ensure only company-owned devices can access sensitive resources. Smallstep solves the other half of Zero Trust by securing Wi-Fi, VPNs, ZTNA, SaaS apps, cloud APIs, and more with hardware-bound credentials backed by ACME Device Attestation. Full description of finalists here.

#here’s a great 🧵 from co-creator of MCP around security and great comments from community

#we now have the first model trained for cybersecurity from Google - Sec-Gemini v1 - all about the data - imagine all of the data Mandiant has provided Google on security vulnerabilities and fixes - this is for automating sec ops workflows

Today, we’re announcing Sec-Gemini v1, a new experimental AI model focused on advancing cybersecurity AI frontiers. 

As outlined a year ago, defenders face the daunting task of securing against all cyber threats, while attackers need to successfully find and exploit only a single vulnerability. This fundamental asymmetry has made securing systems extremely difficult, time consuming and error prone. AI-powered cybersecurity workflows have the potential to help shift the balance back to the defenders by force multiplying cybersecurity professionals like never before.

Effectively powering SecOps workflows requires state-of-the-art reasoning capabilities and extensive current cybersecurity knowledge. Sec-Gemini v1 achieves this by combining Gemini’s advanced capabilities with near real-time cybersecurity knowledge and tooling. This combination allows it to achieve superior performance on key cybersecurity workflows, including incident root cause analysis, threat analysis, and vulnerability impact understanding.

#Microsoft Teams as an attack vector - imagine when bots get access to teams or your user auth the damage it can do…

#💯

#for anyone building in AI, here’s the complete guide to evals and why they are so important 👇🏻

#Glean - enterprise AI search to raise at a $7B valuation??? Pretty impressive Net $ Retention at 120% and 3x to 2X projected growth (The Information) - going to be an intensely competitve space with ServiceNow/Moveworks, OpenAI moving in and many more…

Glean’s revenue rose about three times last year to $103 million in annual recurring revenue as of the end of January, according to people with knowledge of its finances. ARR typically measures the prior month’s subscription revenue multiplied by 12. The startup projected it would generate roughly $120 million in ARR as of the end of April, these people said, and $235 million in ARR, or nearly $20 million in monthly revenue, by the end of January 2026.

For its last fiscal year at the end of January, Glean had a net revenue retention, which measures a company’s ability to keep its existing customers and increase their spending over time, above 120%.

#AI never sleeps - all in a weekend! Meta Llama 4 dropped on a Saturday and on AWS on Sunday 🤯

#Gartner believes CIOs will opt for more off-the-shelf software and reduce in-house builds with significant growth still ahead for GenAI spend

Worldwide generative AI (GenAI) spending is expected to total $644 billion in 2025, an increase of 76.4% from 2024, according to a forecast by Gartner, Inc.

“Expectations for GenAI's capabilities are declining due to high failure rates in initial proof-of-concept (POC) work and dissatisfaction with current GenAI results,” said John-David Lovelock, Distinguished VP Analyst at Gartner. “Despite this, foundational model providers are investing billions annually to enhance GenAI models' size, performance, and reliability. This paradox will persist through 2025 and 2026.

“Ambitious internal projects from 2024 will face scrutiny in 2025, as CIOs opt for commercial off-the-shelf solutions for more predictable implementation and business value. Despite model improvements, CIOs will reduce POC and self-development efforts, focusing instead on GenAI features from existing software providers.” said Lovelock.

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Markets

#Sunday as the week was about to open up…from the man who called the 2008 Financial Crisis and is subject of the book The Big Short…