Web3 CMO Stories Wisdom from a Young VC's Journey | S5 E29
Money shouldn't be your startup motivation: a profound truth that Violetta Chekan, VC and entrepreneur with over 13 years of early-stage investing experience, shares from the beginning of our conversation. "A startup doesn't have any money until the exit. Exit will happen like in five, ten years," she explains, highlighting why founders need deeper motivation to sustain them through the entrepreneurial journey.
Having started in venture capital at just 19 years old and closing her first deals by 21, Violetta brings a unique dual perspective as both investor and former founder. This combination has shaped her approach to evaluating startups, where she prioritizes team qualities over even the most brilliant ideas. "I try to have much more empathy as well to the founders, because I understand the journey," she reflects, describing the founder-investor relationship as a "marriage" that demands careful selection and mutual trust.
Throughout our conversation, Violetta reveals the green and red flags she watches for when meeting founders. Transparency tops her list of essentials, while she's immediately wary of those who claim numerous business connections but can't produce evidence. For blockchain ventures specifically, she differentiates between artificial hype and genuine traction, especially in B2B solutions where she focuses her investments. "You need to have either pilot contracts with companies, either existing agreements, either letter of intent for commercial adoption," she advises founders looking to prove real-world value.
Perhaps most valuably, Violetta shares how her own podcast journey has transformed from overcoming her fear of public speaking to becoming a powerful learning tool through conversations with experienced entrepreneurs and investors. Her story exemplifies the continuous growth mindset she values in founders—the willingness to listen, adapt, and evolve that sets successful startups apart.
Whether you're a founder seeking investment or an aspiring investor, this episode offers rare insights into startup evaluation from someone who's experienced both triumph and failure from multiple perspectives.
This episode was recorded through a Descript call on June 19, 2025. Read the blog article and show notes here: https://webdrie.net/wisdom-from-a-young-vcs-journey/
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