This week, Immad and Raj sat down for a wide-ranging catch-up on the biggest stories in tech right now — from record-breaking acquisitions to what they're each giving AI access to in their own lives.
The conversation kicks off with the OpenRouter-Stripe acquisition and Cursor's $60B deal, and what both say about investing in "obvious" ideas when the underlying trend is right. From there, Immad and Raj get into the economics of secondary markets (including Immad's own purchases of SpaceX and Anthropic shares pre-IPO), why staying private longer might be bad for retail investors, and the case for making it easier for smaller companies to go public.
They also dig into consumer AI hardware — why simple, single-purpose devices like Pocket are breaking through where more complicated products haven't — and trade notes on what they've each connected their own AI assistants to, from email and calendars to health results and scheduled tasks.
What you'll learn:
- Why "obvious" ideas can still be some of the best investments, if the trend is right
- What's driving the OpenRouter-Stripe and Cursor acquisitions, and why they matter for developer tools
- How Immad and Raj think about the risks and opportunities in secondary markets
- Why Immad believes deep secondary liquidity could be bad for retail investors and the broader economy
- What's made simple, single-purpose AI hardware devices succeed where more ambitious ones have struggled
- How Immad and Raj are using AI assistants in their own lives, from productivity to personal health
- Why "PMF doesn't exist anymore" in consumer products, according to a recent conversation Raj had with Character AI's CEO
- What it will take for AI to handle more complex, multi-step tasks like buying insurance
- How Anthropic and OpenAI's revenue numbers compare going into the back half of the year
Timestamps:
(00:47) Introduction
(01:21) OpenRouter's acquisition by Stripe
(02:18) Cursor's $60B deal and the case for "obvious" ideas
(06:03) Why big exits justify high seed valuations
(08:47) AI adoption is still low — why Immad is bullish on the next 5-10 years
(12:56) Buying into SpaceX and Anthropic pre-IPO
(15:17) The case against deep secondary markets
(18:21) Why Pocket is winning in consumer AI hardware
(20:02) Talking to Matic's robot vacuum
(22:07) An idea for family video, and why photo frames haven't solved it
(24:14) What Character AI's CEO said about PMF at a recent Tribe event
(28:28) What Immad and Raj have given their AI assistants access to
(33:08) Scheduled AI tasks, and why AI still can't do the last mile
(35:59) Anthropic and OpenAI's latest revenue numbers
(38:06) The debate over housing density and California's building laws
