Playing the Hand at the Right Time - exits in the AI era
Apr 25, 2026
VCs love to talk about sourcing, picking, winning, and helping.
In the AI era, add one more: knowing when to exit.
Kenny Rogers had the VC lesson right in The Gambler: the hard part is knowing when the hand has played out.
Cursor may be the cleanest example yet. A reported $60B deal for a company with explosive growth, negative gross margin, and a buyer that needed to win the coding race.
In normal software, that combination would raise alarms. In AI, with growth like this and a strategic buyer like SpaceX, it can produce a generational outcome.
The tension is right here: huge growth, ugly margins, and a strategic buyer willing to pay anyway. The bet was growth, usage, and the data flywheel. That bet worked.
At roughly 22x annualized revenue, Cursor looks expensive by old SaaS rules. But the Jefferies data makes the deal feel less like an outlier: half of acquired GenAI companies since 2022 have sold for 20x+ LTM revenue. Scarcity value is real.
That scarcity premium makes sense here. Coding is the biggest AI application market so far, and Cursor had the product velocity, usage, and data to matter. Building a model stack to defend that lead against Claude and others would have required enormous capital. A strategic buyer with compute and urgency can look at the same business very differently than a late-stage investor would.
Every startup has a window where it can realize maximum value. For a rare few, that window comes long after IPO. But in AI, where a lead can disappear almost overnight, knowing when to sell based on future financing needs, dilution, and competitive threats may be just as important as knowing what to build.
In the AI era, sourcing, picking, winning, and helping get you to a great company. Exiting is what turns it into a great return. That is not quitting on the dream. It is maximizing value at peak AI valuations.
As always, 🙏🏼 for reading and please share with your friends and colleagues!
Scaling Startups
seeing this at every portfolio company - the gap between those who have it and those who don’t is widening
not just GPUs in short supply, turns out you need CPUs to orchestrate all those agents! Tae Kim - Key Context
“The next wave of AI will bring intelligence closer to the end user, moving from foundational models to inference to agentic. This shift is significantly increasing the need for Intel’s CPUs and wafer and advanced packaging offerings,” said Lip-Bu Tan, Intel CEO. “
“We delivered robust Q1 results, reflecting the growing and essential role of the CPU in the AI era and unprecedented demand for silicon, as well as our disciplined execution to expand available supply,” said David Zinsner, Intel CFO.”
“For the last few years, the story around high-performance computing was almost exclusively about GPU and other accelerators. In recent months, we have seen clear signs that the CPU is reasserting itself as the indispensable foundation of the AI era. The CPU now serves as the orchestration layer and critical control plane for the entire AI stack.
This is not just our wishful thinking. It is what we hear from our customers, and it is evident in the demand profile for our products. Xeon server demand is seeing strong and sustained momentum. Customers are deploying server CPUs along accelerators in a ratio that is moving back towards the CPU.”
must read for anyone in cybersecurity from CISO JPM with greater than $1B budget 🤯 - all about trying to reduce the vulnerability footprint as fast as possible before hackers can exploit them at record speed and lots more to do with security hygiene…
👇🏻 this plus just the threat of enterprises saying they will build to renegotiate pricing is what is also creating massive downsell on renewals versus just churn
huge open source news - Moonshot just dropped Kimi K2.6 - matches or beats Opus on real coding benchmarks, built for long missions (12+ hours, 4000+ tool calls, 300 parallel agents), 8–10× cheaper + fully open weights
memory is one of the biggest bottlenecks to inference, Google adding a memory processing unit for TPUs - btw, super smart and I do have a port co doing exact same thing for everyone else think Nvidia, AMD 😄
while Medallia’s equity no longer has value, true system of record cos like ServiceNow already have 50% of net new business that are non-seat driven 🤯 - tokens, consumption, connectors
3:05 AM · Apr 24, 2026 · 83.5K Views19 Replies · 19 Reposts · 334 Likes
8:37 PM · Apr 21, 2026 · 29.5K Views16 Replies · 51 Reposts · 155 Likes
3:28 PM · Apr 20, 2026 · 4.33M Views769 Replies · 1.95K Reposts · 15K Likes
3:16 PM · Apr 19, 2026 · 112K Views27 Replies · 36 Reposts · 665 Likes
Vercel @vercelWe’ve identified a security incident that involved unauthorized access to certain internal Vercel systems, impacting a limited subset of customers. Please see our security bulletin: https://t.co/0S939n3qHC3:22 PM · Apr 19, 2026 · 2.19M Views274 Replies · 1.55K Reposts · 9.47K Likes
2:21 PM · Apr 23, 2026 · 36K Views2 Replies · 9 Reposts · 98 Likes