Brian Halligan
@bhalligan • 106,210 subscribers
Co-founder HubSpot | Sequoia | Propeller | MIT Host, Long Strange Trip pod: https://t.co/qj9yOQVYaU
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Videos
🚨NEW Long Strange Trip episode: David Senra, creator of David Senra David has studied the minds of more generational company builders than anyone alive, from Jesus of Nazareth to Jensen Huang. I sat down with him to reverse engineer the psychological frameworks of history's greatest titans. 6 Lessons on the Unfiltered Reality of Iconic Founders. 1. Taste is real, and it starts with shutting up and actually listening. 2. On Negative Self-Talk: Many elite CEOs are fueled in their early days by a dark, chaotic mind and intense self-criticism. They categorically refuse to sleep on their wins, obsessing over everything that is currently broken. I was guilty of this at Hubspot. To survive a multi-decade career without self-destructing, that initial fuel source must eventually convert from negative anxiety into a love for the craft. 3. We need to stop trying to heavily manage or over-advise elite entrepreneurial talent. The greatest founders are irrepressible forces of nature who will relentlessly hunt down the specific knowledge and frameworks they need to win. They are not passively discovered by the market or by venture capitalists; VCs can't help them out of a bad year. They violently force the world to recognize their existence. 4. Small egos don't build big companies. Elite founders are driven by control, not money. Money is just a side effect. 5. Co-Founder Dynamics: Despite the modern dogma that you need a balanced co-founding team to succeed, historical precedent shows that a singular driving force almost always takes over. From Henry Ford operating as an autocrat to Steve Jobs refounding Apple alone, the equal partnership rarely stands the ultimate test of time. Even brilliant minds like Charlie Munger recognized they had to deliberately subjugate their own massive egos to support a singular talent like Warren Buffett . 6. Focus is the whole game: "Mute the world and build your own" as he says. True focus is your willingness to say no to incredibly good ideas because they distract from the truly great ones. 00:00 Introduction 01:11 Focus Above All 01:50 Dana White UFC Focus 04:19 Focus vs Obsession 05:05 Origins in Childhood 06:07 Coppola and His Father 08:48 Assholes and Archetypes 11:14 Autism and Originality 14:55 Immigrant Drive and Grit 16:38 Bet on the Founder 17:52 Solo vs Partners 23:20 Negative Self Talk Fuel 26:39 Platform Shifts and Founder Mode 28:07 Dell Versus IBM 30:02 Infinite Leverage Edge 31:38 Focus Versus Speed 34:20 Taste And Listening 40:52 Founder Traits And Balance 54:22 Closing Takeaways (link to episode in comments 👇)
Brian Halligan79,503 views • 4 days ago
NEW EPISODE: jack & Roelof Botha unpack Block 40% staff cut and rebuilding the entire company as a mini-AGI. This isn’t “use AI to make people more productive.” It’s making the company itself the intelligence. If you’re a founder or operator wondering what work looks like in the next 5 years… this is the episode. The evolution looks like: • Manager mode = Pyramid 🔺 (command & control) • Founder mode = Flat ➖(founders decide fast) • Dorsey mode = Circle 🔵 w/ AI at the center, humans at the edge, and decisions flow from customer inputs → AI → humans steering it I’ve tried killing org charts before. Brutally hard. But we never had these tools. This is rewriting the CEO playbook for the AI era. Buckle up. 00:00 Existential Dread & Hope 02:56 AI Replaces Hierarchy 07:22 Block’s New Three Roles 26:47 Flattening the Company, Fast 35:23 Getting the Board to Buy-In, Fast 36:50 Building a Great Board 41:29 Founder CEO Lessons 48:18 Second Acts & Conviction 56:22 Timeless CEO Traits
Brian Halligan341,087 views • 2 months ago
🚨NEW Long Strange Trip episode just dropped: Ivan Zhao, CEO of Notion jack gave us the circular org chart. Brian Armstrong gave us player-coach. Ivan Zhao just added Jazz Mode. Notion is one of the clearest examples of a great SaaS company making the successful leap into becoming an AI company. That transition is much harder than it looks. Ivan Zhao is the definition of a Refounder, and has rebuilt his company nearly three times. Anyone who is looking to move into this new era, the “jazz era” should listen to this one 👇 Notes from our chat: 1. The Next Evolution to companies is structured freedom You need operators who can improvise and contribute creatively without waiting for orders. Think jazz band over marching band. Leaders must build teams that riff off each other dynamically rather than blindly following a rigid sheet of music. 2. Build a barbell engineering team Pair hyper senior architectural minds with junior talent. Senior leaders provide the taste and direction that language models lack, while junior engineers manage fleets of coding agents to execute the vision. 3. The best companies reinvent themselves When a startup stalls, incremental pivots rarely save it. Sometimes you must cleanly sever the past and start fresh. True technological shifts shouldn't feel like feature updates; they should feel existential. Interacting with frontier models should command a complete re-evaluation of your company's purpose. If a founder hasn't built with AI to feel this paradigm shift firsthand, they cannot find a new path forward. 4. Why Wartime is More Fun Peacetime in SaaS was comfortable, but wartime is where companies actually feel alive. When survival is on the line, the stakes are higher, and a shared, urgent purpose amplifies meaning for everyone. 5. Hire people who can blur traditional roles The best Notion hires have always blurred lines: designers who code, PMs who ship, engineers with taste. Baseline capability is no longer the bottleneck. The premium is now on a candidate's energy, optimism, and fundamental taste across multiple areas. 6. Acqui-hire founders aggressively As companies scale, they naturally calcify and slow down. The antidote is systematically acquiring early-stage startups just for the founders. Ex-founders act as aggressive machinery, breaking old patterns and forcing the organization to regenerate. 7. Financials March, Product Strategy Jazzes You cannot build a rigid product roadmap anymore because the underlying technology shifts too rapidly. Financial planning is the only system that still requires predictability; product strategy must be entirely fluid and improvisational. 8. Make compensation radically more meritocratic The SaaS era of "peanut buttering" compensation across the entire team is over. Companies must transition to extreme meritocracies to reward top performers. 9. Don’t reinvent the wheel unless you must Notion tried to first principle their way into sales. Eventually, they realized that was just plain wrong. Founders waste years trying to creatively invent a new sales system when the classic playbook works best. 10. Decentralizing the CMO Traditional marketing departments move too slowly to keep up with modern shipping cadences. The solution for Notion was to rip the CMO org apart and embed storytelling directly next to the product team. Demand generation now strictly serves the sales function. Lots lots more on this one. Ivan, as stylish as ever, was a blast. Enjoyed this one a lot. (links below) 👇👇 00:00 Introduction 02:22 From Founder Mode to AI Org 11:00 Hiring for Taste and Agency 24:28 Refounding Notion in Kyoto 30:27 Craft Versus Commerce 32:26 When to Refound 34:07 GPT-4 Refounding Shock 45:35 Leadership and Founder Energy 53:17 Sales Culture and Closing Thoughts
Brian Halligan67,524 views • 18 days ago
You basically need to be unemployed to keep up with all this AI stuff. jack feels it too
Brian Halligan190,596 views • 1 month ago
The Marketing department is changing. The role of the CMO is changing. Across all the CEOs that I talk to, Marketing is the team that is using AI the most (second to Engineering). The role is becoming more cross functional, more dynamic. Ivan Zhao talks about how this shift at Notion: - Storytelling is now embedded with the Product team - Demand generation is serve the sales function Those that are part of the Marketing team are now Marketing "and Sales" or Marketing "and Product". This is the evolution to the five tool operator. Links below to my chat with Ivan 👇
Brian Halligan41,751 views • 13 days ago
The most ‘Founder Mode’ CEO working today is not actually the founder. NEW EPISODE with Kaz Kaz Nejatian of Opendoor is now live. This is a special one. Kaz left Shopify to pull off the refounding of a struggling public company in just 16 days. Incredible story. Here are just a few of my learnings from our conversation on the latest episode of Long Strange Trip: 1. First Derivative Businesses The most enduring companies are rarely built on their primary activity; they are built on the first derivative of that core business. Great founders identify and weaponize the secondary value stream. This is important. 2. Rejecting Defaults Success is a function of the defaults you choose to overwrite. Most operators accept the 'software' of their industry or life on autopilot; exceptional builders identify the one or two critical defaults and fight them with all their power to create a new trajectory. Kaz is a master at this, and he explains how. 3. Stewardship Over Status Optimize for doing things rather than being things. When a leader optimizes for a title or happiness, they create fragile organizations; when they optimize for stewardship and service, they build a mission-driven culture that can withstand the lonely and painful stretches of the journey. 4. Write a user manual for yourself "Strong attract, strong repel. My job is to tell you what kind of a person I am so you can opt in or opt out." I love this quote. If you're a founder, you owe this to everyone around you. 5. Founder mode = responsibility for outcomes Hold yourself responsible for truth and outcomes, not processes. Hire people to round you out. Don't try to be well-rounded yourself. And don't work on your weaknesses. "Is the fact that I'm bad at this the reason I'm good at everything else?" 6. Structural Risk Mispricing The one permanent advantage for entrepreneurs is that the rest of the world structurally misprices risk. While others see a 'lion bite' in every setback, the best CEOs recognizes that things going poorly is not as painful as you think, allowing them to lean into volatility that scares off the incumbent. That's the difference. 7. Death Spiral Honesty When a company is in a death spiral, incrementalism is fatal; "what must change os everything." Professional managers are often incentivized by RSUs to delay the inevitable and manage a slow decline. You need zero incentive to manage a decline and a compensation structure aligned purely with performance. 8. AI as the New Performance Default Default to AI is not a suggestion; it is the first line of the job description. A company becomes AI-native not through top-down mandates, but by making AI proficiency a core pillar of the performance management system - effectively deciding who gets to play on the team based on their ability to automate their own craft. 9. The Career vs. Job Distinction "A job is something you do for someone else in order to get paid. A career is something you work on every day for yourself." Kaz's kids know what Opendoor is. His family is all in. Exceptional companies are built by people who self-identify with their work and treat their professional mission as a family-integrated pursuit. 10. Two timeframes matter. Everything else is noise. This week and 10 years from now. "This quarter is a deeply useless measuring period." tobi lutke applies a discount rate of basically zero to the future. That's the model. My takeaway from this conversation: ask yourself what defaults you're living by that you haven't deliberately chosen. Kaz overrides every default, and he does it over and over again.
Brian Halligan270,206 views • 2 months ago
Compensation is changing. This is the era of the five-tool operator. In baseball, a five-tool player hits for average, hits for power, runs, fields, and throws. Most players have two or three tools. The five-tool player is the one you build a franchise around. The best CEOs I work with, the powerhouses, are five-tool players themselves. They can sell, they can fundraise, they have taste, they can design product and they can code. They're Woz and Jobs. Now, with AI, we have the five-tool engineers. Five-tool PMs. Five-tool growth leads. AI removed enough friction that the best people are no longer operating inside one function. They are operating across the entire loop. At Notion, Ivan Zhao has changed comp to be a meritocracy to reward these types of operators 👇
Brian Halligan29,149 views • 12 days ago
“Startups are somewhere between completely impossible and very, very, very, very hard.” That's Parker Conrad, CEO of Rippling, on the first episode of Long Strange Trip. Parker's got one hell of a story. Violently fired by David Sacks from Zenefits. Character assassinated in the press. Everyone (including me) thought he was done. Then he built a $17B company in the exact same space. In this episode, Parker talks about turning your darkest professional moment into rocket fuel. How he keeps a 4,000-person scaleup moving at startup speed. Why he he's hired over 100 ex-founders. And what it's really like when someone plants a spy inside your company. This isn't your typical founder story. It's raw, it's real, and there are some serious lessons buried in the drama. I hope you enjoy it.
Brian Halligan327,370 views • 6 months ago
🚨🚨NEW EPISODE DROP Sally Kornbluth, President of MIT🚨🚨 "If you take a lick of the lollipop of mediocrity, you will suck forever." I love this. She was talking about how MIT sustains excellence after 150+ years. And it applies to founders and CEOs who are trying to scale, more than ever. The thing is, the bar doesn't drop all at once. It drops one hire at a time, one exception at a time. It's better to have nobody than to let the standard slip even once. Every hire, every door, every message has to carry the same signal. That's how MIT maintains it's intensity.....just look at the list of grads like Vinod Khosla Greg Brockman Drew Houston Tarek Mansour Michael Truell Varun Mohan Chase Lochmiller I’ve watched this play out with the companies I work with. They hit 150 employees, the founder stops interviewing everyone, and by 500 they're asking what happened to the culture. Sally's answer: it's a lot easier to stop that slide than to recover from it. The fix is relentless consistency, clarity, and the willingness to say no far more often than you say yes. Worth remembering when growth feels urgent. ------ Listen to the full conversation with MIT President Sally Kornbluth on Long Strange Trip.👇
Brian Halligan81,782 views • 1 month ago
Technical founders: hiring salespeople is where you will most likely get wrecked.
Brian Halligan126,162 views • 3 months ago
One of the smartest things Palo Alto Networks CEO Nikesh Arora said about M&A on the pod had nothing to do with price. When Palo Alto acquires a company, they don’t “integrate” it the traditional way. They flip the org chart. If the founders beat you with fewer people and less capital, why would you put them under your bureaucracy? Nikesh’s rule is simple: they run it. That one decision helps explain why their M&A actually works - and why most corporate acquisitions quietly die. If you’re a founder thinking about selling, or a CEO thinking about buying, his is a masterclass in how talent (not technology) is the real asset.
Brian Halligan159,690 views • 5 months ago
A lot of founders have pinged me to ask what steps they would need to take to pull of what jack has done restructuring Block this way. He answers it spot on 👇 "look at all the tools you're using. Look at all the information you're generating just by doing your work. Just putting that into an intelligence and being able to query it will give you an understanding of the company that is 2-3x more than you had before, ever." If you want to hear more, let me know and I can share my longer thoughts
Brian Halligan67,564 views • 2 months ago
Most companies don't kill ideas by saying No. They kill them by making you ask 14 people for permission. dick costolo fixed this at Twitter when he was CEO with one rule: only your direct manager can block you. "Experiments started flying out." That's bias to yes.
Brian Halligan26,794 views • 1 month ago
The product roadmap is getting replaced by direct customer input in the AI era. jack on what changes when the product IS the conversation: "When your interface is a conversation with your customer, instead of this visual navigation, you suddenly get this amazing fidelity of, like, what do our customers actually care about?"
Brian Halligan38,257 views • 2 months ago
Should computer science and basic coding still be taught in schools at all? Should writing? In my interview with the President of Massachusetts Institute of Technology (MIT), Sally Kornbluth, she asked "I am not sure how much you need to have in your head to think creatively versus how much you have to offload" One of the biggest concerns I hear from CEOs & engineering leaders: Junior devs who’ve never studied or wrestled with great code are skipping straight to letting AI write it for them. If this continues, in 10 years we’ll have very few engineers left who actually know how to think through it.
Brian Halligan30,546 views • 1 month ago
