Gautam Gupta
@gRamblings
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Serving founders and CEOs as a VC investor, ex-CEO of @NatureBox (recovering founder) and ex-VC at General Catalyst. @babson grad / board member
san francisco, ca
Joined October 2008
In consumer it is often not the features that win but the strength of the consumer insight:. Amazon: fast, cheaper, more convenient .Insta: pictures say a thousand words.Tinder: love at first sight .Netflix: No late fees . In the AI era, stay focused on the consumer insight vs.
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I wonder what Soham’s parents think right now. Either proud that they can say he’s worked at several YC companies or feeling shame that he hasn’t been promoted to CTO of any yet.
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Additionally, feels like the second order effect will be making monetization harder for consumer facing AI apps that play in core areas of Google / Meta business (search, browser).
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Meta acquisition of Scale and recent talent adds is a clear signal they will compete with their cash in AI. Google already signaling this with pricing changes. As such, doesn’t the investment case for LLMs (outside of OpenAI) get a lot worse?.
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Good execution comes down to doing 1 thing incredibly well - resist the pressure and urge to do anything else.
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Help me understand the argument that companies will build their own CRM, their own payroll, etc. Do you make your own clothes?.
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One of my learnings as CEO: approve every hire until it is humanly impossible to do so. Adding approval creates a dynamic of rest of company wanting to get the hire right vs get it done.
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I don’t think folks realize that the Lakers transaction is for majority - not 100%. New owner already had 26% and Buss family retaining 15%. Enterprise value is undoubtedly a LOT higher than $10B.
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Has anyone collected data on % of fund invested relative to total committed capital? . I suspect the fee drag from less recycling will have a significant impact on VC returns as duration extends (particularly for seed).
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One of the things many investors don’t realize. Allowing founders (and employees) to have liquidity enables all to go longer / further. Investors have a portfolio, founders do not. Liquidity helps bridge alignment.
Relatively uncommon POV: I encourage founders to take a little money off the table early — as early as Series A. It’s not just good for them and their families. It’s good for the company too. When a founder has some personal financial security, they are:.-Less likely to feel.
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Looked at one of the top 10 multi-stage VC firms today to see what YTD activity looks like:. 80 deals YTD.$50M median deal size.$700M median post-money valuation. Nothing about this makes sense.
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Was this not inevitable / obvious? Horizontal point solutions are likely to face significant platform competition - sort of the repeating history of desktop apps.
Granola getting Sherlocked by OpenAI. On the heels of Anthropic throttling Windsurf’s access to Claude 4. At some point model providers are going to need to decide if they want to be stable platforms or compete for every vertical. Platform risk has never been higher
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Good reminder for CEOs navigating tough times: . Bad news doesn’t need to be breaking news.
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$450m of venture funding down the toilet - growth at all costs playing out again:
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The difference between being a lead investor vs follower cannot be underestimated.
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Some people want credit for work done and some people just want the work done.
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