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Chronicles

The story behind the story

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Q&A with Gokul Rajaram, investor and a former product leader at Google, Meta, and others, on AI changing product development, building ad businesses, and more

Invest Like The Best on YouTube Patrick O'Shaughnessy

Discussion

  • @patrick_oshag Patrick OShaughnessy on x
    Gokul's best career advice: stay long enough to have an impact. “I've been seeing people who stay at a job for 12 to 18 months and then they move to the next job and then the next job. That is one of the biggest red flags as a hiring manager because you can't achieve anything [vi…
  • @patrick_oshag Patrick OShaughnessy on x
    “The one thing that's going to be truly future proof is judgment. What is the biggest challenge when you have a thousand AI engineers writing code? AI slop. In an era when you can do everything, the question is which of these things matter. On the engineer side, it is [video]
  • @patrick_oshag Patrick OShaughnessy on x
    .@gokulr is one of the most prolific product builders and investors of the last 20 years. He helped build the core ads and product businesses at Google, Facebook, Square, and DoorDash, working directly with many of this generation's best founders and CEOs. He's also invested in […
  • @patrick_oshag Patrick OShaughnessy on x
    Gokul explains why outcome-based software companies like Zendesk are more exposed to AI than systems of record like NetSuite, and why public markets are not distinguishing between the two. He argues that the only way AI-native startups can disrupt systems of record is by [video]
  • @gokulr Gokul Rajaram on x
    From a founder: “Just finished listening to your podcast on Invest like the Best. I must say, word for word, probably the most knowledge-packed podcast I've listened to in a long time. Not kidding. I actually canceled a meeting today just to be able to continue listening to the
  • @gokulr Gokul Rajaram on x
    Absolutely loved my conversation with @Patrickoshag - he has the unique ability to: (a) unearth a nugget of insight out of a specific comment and dig 10x deeper into it, and (b) make his guests feel extremely comfortable through his demeanor, as if with a long-time friend. One
  • @patrick_oshag Patrick OShaughnessy on x
    The three ways AI, particularly long-horizon agents, are changing the role of PMs: “First, product development is changing because the models and the capabilities are growing so fast that if you try to be very strict and stringent about describing exactly what you're going to [vi…
  • @mmlionfund @mmlionfund on x
    Great timing for this conversation given today's SaaS sell-off. It's a great talk. Gokul argues that “Systems of Record”—those holding critical long-term data—might remain insulated from AI disruption. He notes that replacing core systems like ERPs is a “career-limiting” move for
  • @patrick_oshag Patrick OShaughnessy on x
    Gokul explains the only three ways ads businesses make money, and why ChatGPT may be more valuable than Google and Facebook: “One, you need to own a very coveted group of users and you need to have a surface on which those users interact. Google Search is a great example. It's [v…
  • @gergelyorosz Gergely Orosz on x
    Here's a story of a customer 4+ years on Zendesk, moving away because they don't want to pay for a vendor that doesn't even have an API their agent can use efficiently Warning for any and all vendors that want to fight customers using them via an API and nothing else
  • @gergelyorosz Gergely Orosz on x
    Zendesk is having trouble with AI because they want to keep customers using a slow UI, but AI-native companies just want an API to plug into their agentic workflow Zendesk hasn't built this API so customers move to the likes of Plaid or others (I have no affiliation btw)
  • @martin_casado @martin_casado on x
    This is fantastic. @gokulr is just the greatest.
  • @mbgilroy Michael B. Gilroy on x
    Our legendary partner @gokulr sharing wisdom on all of our favorite pod with @patrick_oshag. GR is a special human and we're fortunate to see him impart this wisdom on @MarathonMP portfolio companies day in and day out. Also, we just got fresh stock of those MMP @Nike hats, where
  • @kevinweil Kevin Weil on x
    @patrick_oshag @gokulr One of the best of all time!
  • @mohapatrahemant Hemant Mohapatra on x
    Of all the global leaders I chat with, @gokulr's response time is the lowest and his follow up immaculate. No wonder he's got fans literally everywhere. Privilege to know him; everyone should watch this pod...
  • @anshublog Anshu Sharma on x
    Gokul has invested in every newco I started, and we have invested in many startups together. But most importantly when as a founder I need advice on something truly critical, he's often my first call - and he always picks up the phone. @gokulr is an empathetic genius. Pod:
  • @nurijanian @nurijanian on x
    every PM who wants to survive the AI era should watch this video (75 mins) @gokulr shares how product management is fundamentally changing my notes below but you have to watch the whole video: [image]