In this episode of the Established Podcast, Charlie O'Donnell, NYC venture capitalist, community builder, and Author of Founder Unfriendly: What Investors Won't Tell You About Getting Funded joins Frank Gruber, host of the podcast and Co-CEO at Established and Managing Partner at Established Ventures, for an honest conversation about venture capital, startup fundraising, and the realities founders rarely hear from investors. Charlie shares lessons from more than 20 years in venture, including his time at Union Square Ventures and as founder of Brooklyn Bridge Ventures, while discussing insights from his new book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded. The discussion covers why most startups are not a fit for traditional VC, how founders should think about risk, the hidden dynamics inside partner meetings, why storytelling matters in fundraising, and how AI is changing the future of startups and investing. Charlie also shares actionable advice on customer discovery, building community-driven companies, and designing a business that aligns with the life you actually want.

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