Founders in Arms

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

Mo Al Adham is the founder and CEO of Frec, a brokerage platform he describes as "brokerage 2.0" — building on core trading primitives to offer more sophisticated strategies like direct indexing, long-short direct indexing, and options overlays. Before Frec, Mo co-founded Twitvid, an early video-for-Twitter startup, and later spent five years at Twitter. He founded Frec in 2021 and launched the product in October 2023.
What you'll learn:
Why the $1-30M wealth segment — about 10 million US households — controls 40% of all investable wealth in the country, and why it's the fastest-growing segment
How direct indexing creates "tax alpha" by harvesting capital losses, and why that's a deferral of taxes rather than an elimination of them
How a step-up in cost basis at death effectively forgives the deferred tax bill
The concrete numbers: how much a $100k investment can harvest in losses via a classic direct index versus a long-short direct index
Why long-term, sophisticated investors have proven far less fee-sensitive than the market assumes
Mo's path from Twitvid — an early video app built on top of Twitter — to five years working inside Twitter itself
How a frustrating experience with a wealth manager who charged 1% fees for little added value planted the idea for Frec
Why Mo's six months of "top-down" market research largely failed, and why a "bottoms-up" approach — starting from what he actually cared about — led him to Frec
Why Frec had to resequence its roadmap when rising interest rates undercut its original plan to lead with a cheap line-of-credit product
Immad's framework for company OKRs (which he calls "COR") and why he insists on including non-measurable results
Why Frec has deliberately stayed out of banking, unlike some robo-advisor competitors
Mo and Immad's picks for financial products that should already be obsolete

Chapters:
(00:00) The $1-30M wealth segment and why it holds 40% of US investable wealth
(01:03) Introducing Mo Al Adham and Frec, "brokerage 2.0"
(02:07) Targeting sophisticated investors vs. democratizing access
(03:12) Why long-term investors are stickier and less fee-sensitive than assumed
(07:08) Tax alpha explained: deferral vs. elimination
(09:20) How direct indexing lowers cost basis through loss harvesting
(12:45) Long-short direct index and portfolio tilts
(14:16) Mo's first startup, Twitvid, and getting outpaced by Twitter
(16:29) The wealth manager experience that inspired Frec
(19:49) Vetting the idea: six months of top-down research that failed
(22:18) Switching to a bottoms-up approach and finding conviction
(30:39) Immad's approach to OKRs, called "COR"
(36:24) Frec's pivot from lending to investing as rates rose
(52:16) Rapid fire: AI in fintech, obsolete products, and more

Guillermo Rauch is the co-founder and CEO of Vercel, the company behind Next.js, and previously created the widely-used Socket.io library. In this special episode, recorded live in front of an audience, Guillermo joins Immad Akhund and Raj Suri for an open Q&A covering pivots, ethics, investors, and the future of work in the age of AI.
What you'll learn:
The difference between a "lowercase p" pivot (refining focus) and an "uppercase P" pivot (starting over) — and how to know which one you need
How to build an ethical framework for operating in an industry full of shortcuts and noise
How to extract real signal from investors without letting them drive your roadmap
Real pivot stories from Presto (restaurant tablets to voice AI), Lyft (carpooling to peer-to-peer ride-hailing), and Mercury's early product-market-fit signal
Why blaming distribution is often easier than blaming the product — and why that's a trap
How founders can get their teams to think about prioritization the way they do
How Mercury created early demand by deliberately recruiting a broad, vocal set of seed investors
What "the future of work" looks like when your team's job shifts from producing outcomes directly to building the systems that produce them
How growing up outside Silicon Valley shaped each panelist's belief that they could build something from scratch

Chapters:
(0:00) Lowercase p vs. uppercase P pivots
(1:05) Q&A begins
(1:23) Building an ethical framework in Silicon Valley
(4:38) Balancing customer signal vs. investor advice
(9:53) Pivot stories: Presto, Lyft, and Mercury's obvious PMF moment
(15:34) Why founders blame distribution instead of the product
(16:08) Getting your team to think about prioritization like you do
(18:21) How Mercury created early demand with 60 seed investors
(19:48) The future of work: agents, harnesses, and factories of output
(24:25) Growing up outside the Valley: mentors and self-belief
(28:04) Closing

Dan Teran is the co-founder and managing partner of Gutter Capital, an early-stage venture firm investing in vertical AI and marketplace businesses. He previously founded Managed by Q — an operating system for commercial spaces that grew to employ nearly 1,000 people, expanded nationally, and was acquired by WeWork in 2019. Dan joined WeWork as head of corporate development before leaving after a turbulent six months. He now runs Gutter Capital's third fund ($75M) and the Elbow Grease accelerator, sponsored by Mercury, which invests in early-stage founders in New York City.
What you'll learn:
How Managed by Q found extreme product-market fit in lower Manhattan — and why that made expansion harder, not easier
Why winning a market can be a trap when the TAM is smaller than you thought
The real story behind the WeWork acquisition: a three-year relationship, a theatric walkout, and why great exits are always principal-to-principal
Why over-capitalization was more ruinous to Managed by Q than any external factor
How to think about Series A benchmarks for non-AI companies today (2–3M ARR, renewals, one productive AE, 3x growth)
Why AI-enabled services businesses can be great companies even if they're not venture-scale outcomes
The mismatch between what early-stage founders need to raise and what top VC funds are mandated to deploy
Why founders should play the hype game — but stay ruthlessly honest with themselves about what game they're playing
Dan's take on Adam Neumann: what made him exceptional, where he fell short, and why Dan wouldn't bet against him
The "leaders eat last" philosophy — and why holding people to high standards and having their backs aren't in conflict

Chapters:
[00:00] The hype trap founders fall into
[01:31] Managed by Q: founding story and early growth
[02:39] Scaling nationally and selling to WeWork
[04:17] The state of co-working and commercial real estate post-WeWork
[07:18] In-person vs. remote — what actually matters pre-PMF
[11:16] How the WeWork acquisition really happened
[15:06] Realizing the TAM was smaller than expected
[17:09] Raj's parallel experience at Presto
[20:04] FOMO-driven investing and the AI diligence problem
[22:04] Series A benchmarks for applied AI companies today
[25:27] Why founders should aim for break-even before raising
[28:56] The mismatch between venture fund mandates and founder needs
[34:32] What Dan learned about fundraising after becoming an investor
[37:30] Adam Neumann, WeWork, and Flow
[39:30] Leadership, high standards, and the "leaders eat last" philosophy
[42:12] Why founders learn the wrong lessons from Steve Jobs
[47:31] FarmEvo: the drone ag company Dan flew to Karachi to diligence

Colin Angle spent 33 years building iRobot — bootstrapping for eight years without venture capital, surviving 15 failed business models, and ultimately launching Roomba in year 12. What followed was a decade of overcoming consumer skepticism, 70%+ global market share, a public offering on Nasdaq, and eventually a blocked acquisition by Amazon. Now he's back with a new company, Familiar Machines and Magic, building robots designed for human connection — priced to compete with the cost of owning a pet.
What you'll learn:
Why Colin believes iRobot would have failed with early VC access
How iRobot funded itself for eight years through customer contracts instead of investors
The sales tactic Colin used to get Fortune 500 CTOs to fund iRobot's R&D
How DoD mine-hunting algorithms and a Hasbro partnership became the technology inside Roomba
The wallet share framework for evaluating whether a consumer robot idea can actually work
Why adding features to a consumer robot often reduces perceived value
How iRobot priced Roomba at $199 with a $42 BOM — and what that discipline required
What it felt like to go public, and how everything changes when what you say can be monetized
The full story behind the Amazon acquisition attempt and why the EU and FTC blocked it
What Familiar Machines and Magic is building and why the pet economy is the target comp

Chapters:
00:00 – Regulators celebrate blocked deals — what Colin saw on FTC examiners' doors
00:53 – Introducing Colin Angle, co-founder of iRobot and Familiar Machines and Magic
02:00 – The "if not us, who?" moment that started iRobot
03:54 – First business model: privately fund a moon mission, sell the movie rights
07:03 – Eight years without VC: "completely unfundable"
08:09 – The CTO sales tactic: present a problem half a step from their real one
09:00 – "Work for no profit, cancel anytime" — the deal structure they used five times
12:05 – Built for 10,000 units, sold 70,000 Roombas in three months
15:03 – "If I had VC early, iRobot would have failed"
18:40 – $199 retail, $42 BOM — the Roomba economics
20:31 – The wallet share framework: which consumer spend are you actually replacing?
32:39 – First interview as a public CEO: "My wife says Roomba doesn't work"
34:42 – The Amazon acquisition gets blocked — 15% market share and falling
42:09 – Familiar Machines and Magic: the new company and the original vision
46:12 – Building robots for human connection, not task automation