Everyday I am in the gym at the same time as an old man on the treadmill. Today I stopped him after the workout and introduced myself. Turns out he started his business in 1982. He has scaled it over the last 43 years, slowly but steadily every year. Today the business does $4.5BN in revenue. He owns 100% of it. Never raised a dollar. At 75, he remains CEO. That’s a magical story of entrepreneurship.

I have never met a top-performing CEO who likes the role of HR. They are here to slow us down and instill meaningless process.

Most podcasts are BS because they are fluffy and lack substance. This is the densest, most insightful episode you will listen to this year. @gokulr breaks down the 8 defensible moats you need for your company to be successful in a world of AI. 1. Data (Proprietary and inaccessible) 2. Workflow (Deeply embedded operations) 3. Regulatory (Licenses and contracts) 4. Distribution (Exclusive proprietary channels) 5. Ecosystem (Third-party platform reliance) 6. Network (Marketplace liquidity density) 7. Physical (Infrastructure and atoms) 8. Scale (Low cost through volume) (Links below)

You want to see how hard modern media is: Conversation with Mark Zuckerberg on AI hiring… 39 likes in 9 hours. Brutal.

I walk every night for 90 mins through London. Tonight I saw three phone thefts in the space of 15 mins. @MayorofLondon I will donate $50,000 if you join me and have a proper discussion about the current state of London. You game?

I just walked with a $10BN public company CEO. He told me his CoS replaced a piece of software they had been paying $1.2M per year for. It took him 3 weeks to build. F*** me software is more toast than I thought.

The amount of hype and BS going around about enterprise AI adoption is insane. Aaron @levie is the most AI forward-thinking CEO in public markets today. But even Aaron at $1BN+ in ARR is valued at $3.3BN and getting smashed by Wall St. I sat down with Aaron to understand WTF is happening, what is real and what is fake in enterprise, WTF to do with token budgets and wrote up my notes below. (Link to full episode in comments) 1. Why Dwarkash Was Wrong and Jensen Was Right on Upgrading Systems Upgrading software is a multi-year effort, not a "magical moment" where everything can be secured overnight. The reality of enterprise security is an ongoing, endless cycle of "leapfrogging" between defensive and offensive capabilities. Founders must realize that even with access to frontier models, the implementation cycle in the real world remains the primary bottleneck. 2. Why We Will Have More Lawyers in Five Years Not Less The industry is myopic about job elimination; AI makes it easy to generate content, but it hasn’t made it easier to get that content approved by a court or a patent office. As clients inundate lawyers with AI-generated contracts and memos, the "ultimate constraint" becomes the number of qualified humans available to review and approve the output. 3. What Role Does Not Exist Today That Will Be Incredibly Common in Five Years? We are about to see the creation of 500,000 to 1 million "Agent Operators". These technical-yet-business-savvy individuals will be responsible for "care and feeding" of agents—writing skills, understanding MD files, and redesigning workflows for agents rather than people. 4. Will Massive Software Providers Simply Be Turned Into a Database That Agents Crawl Over? While the user interface may shift to chat, the value is moving to the API layer and the "business logic" embedded above the database. Systems like ERPs are more than databases; they contain decades of complex logic for supply chains and accounting that agents must interact with, not replace. 5. What Everyone Thinks About Enterprise AI Adoption That They Get Wrong The assumption that the massive gains seen in AI coding will immediately translate to all other knowledge work is a "misread". Coding has specific idiosyncrasies that don't always exist in broader knowledge work, where human collaboration and regulatory loops are more complex. 6. Where Would You Be Investing if You Were a VC Today? Despite high valuations, Levie would still be "loading up" on frontier rounds. These companies have the potential to grow much larger because the ultimate market for AI is often larger than the industry currently realizes. 7. The Budget of Tokens Will Have to Move Out of IT Spend and Into Opex Enterprise AI shouldn't be treated as a tradeoff between software licenses. Instead, token budgets will move into regular operational expenditure (OPEX), where businesses trade off a marketing campaign for a more productive, automated marketing engine. This allows AI companies to tap into a massive pool of capital beyond the traditional, capped IT budget.

I am really sorry but in the year 2025 the idea of putting OOO on email autoresponder is insane. You have a phone, keep emailing. 😂

Spoke to three public company CEOs today; all three said the same thing (almost identical). At this stage, IDGAF anymore. When you are valued at 3x cashflow, you have nothing left to lose. All three, literally said exactly the same.