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. Get Involved! Founders, investors, startup teams, entrepreneur support organizations (ESOs), and innovators, we invite you to join the Established Network, our digital hub where creativity, capital, and collaboration collide. https://established.network Watch the episode on the Established YouTube Channel at: https://soty.link/ESTYouTube Thank you for listening, and as always, please check out the Established website and subscribe to the newsletter at: www.est.us Subscribe to the Established podcast: https://theestablishedpodcast.com/ Startup of the Year helps diverse, emerging startups, founding teams, and entrepreneurs push their companies to the next level. We are a competition, a global community, and a resource. Startup of the Year is also a year-long program that searches the country for a geographically diverse set of startups from all backgrounds and pulls them together to compete for the title of Startup of the Year. Check out Startup of the Year at: www.startupofyear.com Established is a consultancy focused on helping organizations with innovation, startup, and communication strategies. It is the power behind Startup of the Year. Created by the talent responsible for building the Tech.Co brand (acquired by an international publishing company), we are leveraging decades of experience to help our collaborators best further (or create) their brand & accomplish their most important goals. Check out Established at: www.established.us Connect with us on X (formerly Twitter) - @EstablishedUs Connect with us on Facebook - facebook.com/established.us
