3 good quotes from my interview with @TomBrady today, applicable to all aspiring GOATS. 1. "I treated practice like the Super Bowl." — On why he was never nervous in the big moment. He'd already run it 100 times before. 2. "You have to make a lot of bad decisions to gain the experience to make good ones." — His whole theory of getting good at anything new. Including AI. 3."We only grow when things are outside our comfort zone." — The GOAT, on why he keeps starting over at things he's bad at. 🐐

Ali Ghodsi never wanted to be CEO. In 2015, he was interviewing for a professor job at Berkeley when the @Databricks board handed him the interim title. Revenue that year was $1.5M. This episode with @alighodsi will go down as one of my favorites. 10 things I took away: 1. Focus the entire company, orders of magnitude of attention, on its single biggest bottleneck. Like a laser, almost to an extreme. The cycle is 1-3 years, not weeks. If your focus changes weekly, then you’re just in firefighting mode. 2. There is nothing worse than a conflict-averse CEO. They are wonderful people, but they are in the wrong job. Conflict is the gym for a CEO: nobody likes it, but everyone has to go. 3. Study your enemy carefully, understand their weaknesses and apply your strengths to those weaknesses. Snowflake had 2x his revenue. He didn’t copy them. He found three weaknesses (proprietary, no AI, expensive) and hammered them account by account for four years. Watch the competition, never follow it. 4. The concept of a Lakehouse was ridiculed internally and online. No one wanted to market with this new term. So he made the whole company religious about it anyway, killed the ads that converted better without the word, and put it in the sales comp plan. It worked. All hands on deck, no exceptions. 5. Be willing to take a step back for a much bigger vision, even when the company is already succeeding. At multiple hundreds of millions in ARR, he was unhappy, because the vision he pitched investors wasn’t the company he was running. So he took one step back to go ten forward. 6. On the flat org, player-coach model that a lot of people have talked about this year: “it’s BS.” Separate how the company thinks (AI, ontology) from how the humans get managed (they are after all, still humans). His staff meets 3x a week. I asked if it could just be coordinated in a Google doc. His answer: do you meet your wife and kids, or coordinate that in a Google doc? 7. His test for a sales leader: can they build the car, or just drive it? Ron Gabrisko, the Databricks CRO, had seen $0→50M and $50→100M+, and hadn’t changed jobs in 10 years prior to joining. Now he has been the CRO for over a decade. He built and drove the car the whole way. That almost never happens. 8. Hire execs ahead of the curve because by the time you need them, it’s too late. A real search takes 6-12 months. The extra time helps you increase false negatives and decrease false positives. Do an insane number of backdoor references because 80% of ‘front door’ references are bs. 9. The best salespeople are not super technical, so stop trying to force them to be. Square peg, round hole. The best win with professional aggression, high EQ, and mapping the real power base (how decisions get made high up in an organization), not technical depth. 10. Yes, your best AEs will annoy people. One of the first at Databricks got a meeting nobody could get, but got banned from the customer’s building for it. He told Ali, “what are you complaining about? I got the meeting.” Professionally aggressive is the bar. One bottleneck, zero wussing out. He reminds me of @elonmusk that way. Chapters 0:00 – Introduction 1:22 – The secret CEO search and why the board bet on a founder 4:11 – Professor or CEO? Always taking the harder option 8:18 – Pour everything into one bottleneck 12:16 – Killing PLG and learning what great enterprise sellers actually have 19:09 – Hiring ahead of the curve: sales leaders, execs, and back-door references 27:02 – The Snowflake rivalry: study your enemy, never copy them 33:22 – Lakehouse: conviction, ridicule, and the case for second acts 41:02 – The killer instinct and why conflict-averse CEOs fail 44:10 – Dunbar's number and rethinking the org chart around AI 48:00 – AGI is already here — enterprises just use it as a chatbot 52:55 – Does he still code? Two days for a connector vs. three quarters 57:18 – A day in the life, and why the Monday meeting isn't theater 1:04:53 – Why Databricks will go public, just not yet 1:08:09 – Get over conflict aversion, or don't be CEO 1:11:07 – Brian's takeaways Link to more in the comments.

What everyone thinks they know about Sequoia but actually gets wrong "Everyone thinks that we're just waiting for the phone to ring for the next Anthropic to call us to invest. That's completely false. Everyone at Sequoia is a hunter. It doesn't matter how long you've been here, everyone expects you to perform. It's very competitive out there. We think that people need to behave exceptionally well as individuals, but win as a team." @JulienBek What does everyone think they know about Sequoia that they actually get wrong @sonyatweetybird @Alfred_Lin @gradypb

Avoiding hierarchy as you scale — 10 things that actually work: 1/ Don't have an office. Sit with the employees. 2/ Sit in customer support and take calls every couple of weeks. Multiple benefits! 3/ Publicly praise people who disagree with you on Slack or the wiki. 4/ Push for 15:1ish reporting ratios. Flat orgs move faster. 5/ Host quarterly dinners at your house with 8 people who don't report to you. Multiple benefits!! 6/ If you fly private, shut up about it. 7/ Bring non-direct-reports to offsites. 8/ Get good at assigning DRIs who can drive projects across org boundaries. Single owner, no committee. …If you ask a committee to look after your plants while youre away, you’ll come back to dead plants. 9/ Take hard questions at all-hands and don't spin. If you need to think on a tricky one, say so — then actually follow up on slavk, wiki, wherever. 10/ Publish your priorities publicly. Transparency kills hierarchy faster than any org redesign. Bonus/ Jensen is mostky right. Dirrct report 1:1’s should only last a short while. Criticizing (with care) and praising in public irks, but works.

"The illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn, and relearn." - Alvin Toffler A lot of DMs about what inspired me to build Hal, my second brain and digital twin. This quote sums it up.

“Two years ago, we started to hire a different shape of engineers. No longer optimized for people's experience. Optimize for people's agency, energy, optimism, curiosity. A rough framework we're using is…. Talent = Capability/Experience x Taste/Value System x Agency/Will” - @ivanhzhao

A lot of people have messaged me to ask about my Hal. He's been so fun to build, on nights and weekends. There are two parts to him: One is the Hal-brain, which I built with Claude Code, Google Drive, @vercel, etc. It is a file system that is kind of a replica of my brian. There's an individual file on all the companies I work with, all the people, and all the initiatives. This sits in Google drive. Second, I created an end point for it that Tavus uses for the avatar part. Having an AI human / digital twin join your meeting might feel weird right now. But remember when AI meeting recorders first came out? People thought it was strange. Now, it’s just the standard. Hal is a little weird today. He will be an absolute necessity tomorrow.

I cloned myself. Meet v2 of Hal = my second brain and AI human (digital twin) He is 10x better than v1, which we posted a few weeks. Smarter. Faster. More me. For most of my career, I chased developers to help me build something. For Hal, I did it myself. I stayed up until 4 am several nights building the core brain, connecting all the tools. Having total control over the context and architecture was the most fun I’ve had in years. He is an actual presence in my meetings and remembers more than I ever could.

In the early days, Clay locked in 4 key pillars that still haven’t moved. Because they’re fixed, every hard product decision gets easier, it just has to map to one of them. - build for a technical user → the GTM Engineer - power and flexible over simplicity - be the data marketplace, do not own the data - charge by usage not seats Full episode in the comments

This is the reason that Clay has dominated their category. Kareem doesn’t waste time protecting the current moat. He obsesses over inventing the next one before anyone else catches up. Code is cheap now. Whatever edge you had last quarter is already degrading. Keep shipping faster than the market can copy. 👇Full episode in the comments

Be a momentum detective. I love this phrase. Kareem's point is that momentum is brutal to rebuild once it's gone, so the job isn't to crowd into the parts of the company that are already ripping. It's to find where momentum is starting to fade and give it a nudge before it stalls. 👇 Full episode about how Kareem does this at Clay in the comments

I am the first to admit it: I had Kareem, the CEO of Clay, all wrong. When Clay first crossed my radar, I thought he was too laid-back: no obvious chip on his shoulder, no external veneer of obsessive, rabid 'run through walls' CEO persona that we all look for. Kareem builds from what he calls "a place of wholeness" rather than lack - noting to prove, no revenge plan. It makes him sound almost too chill, but the operating instincts underneath are sharp. Crazy sharp. Clay has since exploded. $2M ➡️ $100M in two years. But let's not gloss over that he spent roughly five years wandering before Clay clicked, and his takeaway is that the hard part of building isn't working hard, it's the courage to commit to one idea and stop listening to everyone else, customers included. He flipped every assumption in his market: sell to technical "go-to-market engineers," charge for usage instead of seats, pick power over simplicity. We both created new types of roles for our categories, in completely opposite ways. I flogged "inbound marketing" with a book, a conference, and relentless content. Kareem coined "go-to-market engineering" and then refused to take credit, letting agencies own it because a category has to be bigger than you. We also get into his "momentum detective" theory of the CEO job, why he's deleting his standing one-on-ones, and why apologizing is one of his sharpest tools. There's no single way to run a company. Kareem is my proof. 👇 Full episode in the comments

NEW EPISODE of Long Strange Trip with the CEO of Clay, Kareem Amin Clay is one of those companies where iykyk. The Go-To-Market Platform for the AI Era that went from $1M ➡️$100M ARR in two years. But it wasn't always that way. Everyone I spoke to about Kareem, from employees to investors, to former colleagues and even competitors describe him as more of a philosopher who happens to be scaling a 🚀 than a typical CEO. They aren't wrong. Kareem is different. A few things we get into → Why "9-9-6" is performance art and sometimes a sign you just don't have a moat → How they run the company with “just-in-time” decision making, not exact team meetings (love this) → How they named a category instead of trying to invent one, and turned the Go To Market Engineer into a movement → Being a momentum detective & where a CEO should actually spend their time → Why he answered a pricing backlash by publishing his exact internal reasoning → Building from wholeness, and not the overplayed chip on the shoulder → The silent-retreat realization that changed how he thinks about building → The Hegelian Product Flip strategy → Why future thinking can be detrimental 00:00 Introduction 01:35 Competitive Fire and Drive 03:06 Building From Wholeness 06:42 Living in the Present 09:31 Contrarian Founder Style 14:40 Five Years in the Desert 27:35 Naming GTM Engineering 35:49 Winning Content Battles 36:10 Naming the Category 37:27 Building the Agency Channel 40:19 Pricing Backlash Playbook 43:15 Momentum Detective CEO 52:32 Trust and Tough Calls 01:03:49 Calling Out Elephants 01:06:41 Closing 👇Full episode in the comments