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Rob Bailey
@RMB
AI-Native & Agentic Founder/Operator (New AI company launching Summer 2026)
New York, NY
Joined January 2009
Posts
  • Pinned
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    There are massive opportunity areas in AI adoption that no one is thinking about yet.
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    Very dumb question: How come people are more concerned about Elon's ownership of Twitter than say....China's ownership of Tik Tok?
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    If a VC fund is all white men, there is ZERO chance we will consider them for our next round of funding. Partner / portfolio diversity will be a major factor in which funds we decide to engage first. I know *tons* of other founders feel this way.
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    Brutal Truth: I have found that there is a strong correlation between how fast people respond to email/texts/calls and how successful they are in their career. Exceptions to every rule, but overall I've found there are few for this one.
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    Replying to @pjozefak
    Have you considered about focusing instead on things like their experience, how they answer/ask questions, relevant experience, etc?
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    Replying to @jacksonhinkle
    You're a horrible person
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    The biggest beneficiary of a tight, well done deck isn't a VC, its the founder. While painful, building a good deck forces a clarity of thought that can be extremely helpful for a founder building a company.
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    Replying to @MAGAVoice and @MTGrepp
    So you’re on the side of someone who tried to ruin the lives of Americans whose kids had been killed?
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    Dear Enterprise Founders: This was Salesforce's first office. They are now worth $227.63B. Keep building. :-).
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    Replying to @AJEnglish
    Your journalist had a hostage in their home.
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    Replying to @pjozefak
    Believe it or not, lots of people can’t afford those and /or may live in countries where MacBooks and AirPods aren’t available.
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    I grew up in Latin Am and lived through periods of huge inflation and devaluations. The biggest crypto critics are typically white guys who grew up in the US and don’t understand the instability of non-G7 fiat.
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    Signs of A 🔥 VC: 1. Don’t go to (most) conferences 2. Their founders rave 3. Very fast decisonmaking 4. Generally cool footwear 5. Incredible listeners 6. Very aggressive on hot deals 7. Partnership diversity 8. Uncommon conviction 9. Uncommon sourcing 10. Team players
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    Dear VC Associates/Principals: Good news! If you come well prepared to a first call with a founder (know product, smart questions, etc.) you have a great chance of building a solid relationship. If you do a call with no prep, you might kill your fund's chances. Plan accordingly.