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

“We disagree a lot. Like, all the time.” When you're building a company, you don't need constant harmony. You need a mirror. Someone to expose your blind spots, challenge your logic, and stand up to you. And vice versa. @kalshi CEO @mansourtarek_ on his dynamic with his co-founder @luanalopeslara: “We disagree by design." The best founding teams aren't perfectly aligned. They're productively oppositional. Tag your mirror below 👇 (Full episode in the comments)

Every board meeting 1. We are growing v fast 2. We need to fix gross margins 3. We’re behind on enterprise reps 4. We’re moving to credits pricing 5. We have one pesky competitor 6. We’re very worried re Anthropic If this is you, you have a lot of company.

Notes like this are the best part about starting a company: Hello Brian & Dharmesh,  I joined HubSpot in March 2013 as one of the early DubSpot team and after 13 incredible years this is my last month. Many times I've heard Brian talk about building a company that your grandkids can be proud of. I am writing this email partly to give you an insight into the incredible impact you've had on my life and partly because I imagine it is difficult for your family to appreciate the impact HubSpot has had on so many like me. I hope you share this with your family.  I joined HubSpot at 26 yrs old as a Level 1 Sales Rep. I was early in my sales career, highly motivated and eager to learn. HubSpot gave me an opportunity I couldn't have imagined and I didn't fully appreciate until later. I worked hard, learnt fast and chased targets. I moved to Manager and later moved to Sales Director. In January 2014, Nisha Anand joined as a Level 1 Support Rep. We met, fell in love and got married. She also worked hard, learnt fast and chased promotions. She is now a Principal Solutions Engineer on UK Corp.  Financially HubSpot has transformed our lives but it is more than that. Our friends are HubSpotters. At our Wedding there were tables of HubSpotters. There are family and friends in Leitrim and Belfast that still cannot explain what HubSpot does but they follow it in the news, check the stock price and ask us "what's happening at the big American company?". HubSpot is part of our life story. At every step of our lives HubSpot has been there:  - We timed our Wedding so we could take our sabbaticals for our Honeymoon.  - We sold HUBS shares to buy our first home - When Covid hit we continued progressing our careers working from home - We used tuition reimbursement to up-skill and learn at Harvard, UCD and Oxford. - We used the Temporary Mobility policy to work from London for 1 month during fertility treatment. It worked and we got pregnant. - When our twins girls arrived 10 weeks early and spent a month in hospital, HubSpot supported us. I had 6 weeks for Paternity leave plus used my 2nd sabbatical to be there for my family - My wife took 12 months of maternity leave plus her 2nd sabbatical and returned to continue progressing her career and recently triggered another promotion. - We sold HUBS again to move into a bigger home. My father tells me that I have spent one third of my working career at HubSpot. It is almost impossible to explain the impact HubSpot has had on my life. What an amazing company. I hope you and your family are incredibly proud of what you have built. For the rest of my life I will be grateful to you and HubSpot. Wishing you and your family all the best in the future.

I had a chance to interview @jack on Long Strange Trip and then sit in on his Q&A with a bunch of Sequoia founders yesterday. Here's my take followed by my takeaways. Almost all of us are running a derivative of the playbook laid out in Andy Grove's "High Output Management" book that has been lightly edited down through the generations. Jack's set of ideas is a stark departure from that playbook. It reminds me of the shift I went through at the start of my career (pre web - yes, I'm that old!) to "digital transformation," but this is a much bigger, harder shift. Some of my CEO friends have pushed back on these ideas saying something to the effect that Jack isn't a great CEO so we shouldn't listen to him. First, I'm not sure if that is true, but even if it is true, he is an undeniable innovator and first principles thinker applying that thinking here to org design, not just product design. Second, @brian_armstrong, a consensus great CEO is running something that sounds VERY similar to this playbook as well as almost every startup created in the last 18 months. Third, the first quarter Jack printed after putting this in place was a banger. ...To that end, I think we should all call this new playbook, "Dorsey Mode" after the guy who stuck his neck out. If you want to run Dorsey Mode, a lot of things fall out of it that fall out of it: 1. Strategy - Planning cycles are out the window because the speed increases too much. All those 1 way doors you were procrastinating now look like 2 way doors. 2. Distribution - Given how much easier it is going to get to build products, competition and customer confusion will reign. In this new world, distribution is king. Companies with truly creative distribution strategies (rare!) will gain advantage. Also, long live ye olde enterprise sales. 3. Interviewing - All of the startups I work with have changed their interviewing process. Many have a case with a hard ai problem to solve embedded in it or at least have the prospective employee open their laptop and show them something interesting they built with ai. 4. Profile - There was a split in my group of CEOs at the Q&A -- some were learning hard into pilled jr engineers and some were leaning hard into very senior engineers. It roughly seems like the older companies with more code like Meta and HubSpot, are leaning harder into the very senior engineering types. ...Everyone seems keen to hire "curious" types not afraid to go very deep down rabbit holes. 5. Org shape - Triangle shaped org charts are like democracy, its the least bad system we've got. The biggest problem with triangles is that they get worse with size. The new org chart, in theory, is circular with the world model in the middle and very small teams surrounding it. Very few pure managers in the middle anymore. This seems "early," but directionally right to me. 6. Compensation - The difference between a middling employee and a top one is getting much wider which will necessitate a net new pay scale with a much higher standard deviation. 7. Titles - Jack got rid of them and is trying to focus everyone on the work as opposed to the level. As someone who tried this earlier in my career at HubSpot, I'm a little skeptical of this one, but the meta point of trying to focus people on what they "lead" versus who they "manage" is a good one that I hope sticks. 8 Decisions - Almost all decisions these days are made by carbon based life forms. Dorsey Mode turns an increasing amount of decisions over to the system. 9. IT - This is will totally change as their primary function will be to building the scaffolding for the world model and enable the company to keep feeding it the context and taste it will need to improve. EVERYTHING needs to be "legible" (I hate that I'm using that overused word, but it works) ...Btw, an early sign that a company is in Dorsey Mode is when they record every meeting, including the one on one's, cleverly stripping out some HR bits and centralizing them for use by the model. Btw, Ray Dalio had it right, but was just too early. 10. Slop - As more non-technical people build more things, there will be more slop. I didn't grok Jack's answer to this and I'm not sure the answer myself, but Dorsey Mode companies will need to figure out a system to reign in the badly designed systems. 11. Agency - This another word I cringe at using b/c it is so overused, but hiring folks with high agency that are self motivated will be key. The tricky part is that the beef with the current generation is that they are less like this than their predecessors. 12. CEO - This isn't something that will bubble up. The CEO needs to run hard at it and push it down hard and expect to get pushback from laggards. Jack spends 3 hours every morning building hard things with the new tools. ...AI isn't something that lends itself well to learning by reading or watching a video, so CEOs are running hackathons, show & tell's, building days, office hours, and token leader boards. ...Btw, lots of companies are doing the leader board thing (including mine) -- I think this works until it doesn't! 13. Budgets - Budgets in a lot of software orgs are basically enumerated in headcount. The denomination goes back to dollars. As Jack (and my cofounder @Dharmesh) likes to say, in some cases, it is a lot riskier not to take a risk and this is one of those cases.

Given how easy it is getting to build things, distribution and business models will be keys to victory. I just don’t see much creative ideas here and I don’t count changing the name professional services to forward deployed engineering. What amazing stuff is happening here?

Dear founders, Put your vc's to work for you. They can help a metric ton on recruiting, customer intro's, mentoring (some of them), etc. Don't be afraid to give them a list of to do's coming out of your next board meeting. Love, Bh.

When you're building a company, fires will always come. Your job isn’t racing between them, it’s mapping the territory, building firebreaks, and designing the whole system so one spark doesn’t burn everything down. "Your team kills today’s flames. You shape the forest that survives them." @dickc

Every risk you take is a deposit. You don't always know when you'll cash it out. Ex-Twitter CEO @dickc tried to get on Saturday Night Live. Didn't make it. But that risk compounded in ways he didn't expect. When someone asked if he was comfortable going live on the news, the answer was obvious. He'd already been booed at midnight in front of a thousand people in Australia. p.s. @nbcsnl I think this was a mistake!

With AI tools today, CEOs can either be laser focused, and say no to almost everything (like Jobs) or they can use the tools to do even more, and get involved in everything (like Bezos). Which is better? @dickc talks about this on the pod, and how he led at Twitter.

For the last few months I’ve been interviewing CEOs about their personal AI stacks 🤖. What helps them run the company better / faster / smarter/ The most AI-pilled ones are running 20+ agents that basically run their entire day. I can't 'wait to share more. What’s surprising me: some of the younger, newer founders are the least aggressive with it. They haven’t hit the scale + dysfunction where they need drastic AI intervention yet. For now, all the CEOs are sharing in a tight private group. Will open it up soon….but first: Who are the CEOs (or founders) with the most impressive personal AI setups right now? Drop names below 👇 I want to chat with them.