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.
• Team quality trumps idea brilliance when evaluating startups for investment
• Money as primary motivation is a major red flag for investors
• The founder-investor relationship is a "marriage" that often lasts longer than actual marriages
• Transparency and honesty from the first meeting establishes essential trust
• Adaptability and willingness to pivot quickly demonstrates founder resilience
• Real B2B blockchain solutions need verifiable traction through contracts or letters of intent
• Successful CEOs must excel at "sales" to investors, employees, and customers
• Authentic founder stories about why they started matter more than polished pitches
• Having experienced both success and failure provides invaluable perspective as an investor
From Entrepreneur to Investor: Wisdom from a Young VC's Journey
In the fast-paced world of venture capital and startups, understanding what makes a successful founder-investor relationship can be the difference between failure and a thriving business. In a recent episode of Web3 CMO Stories, Violetta Chakan, a VC with over 13 years of experience in early-stage investing, shared invaluable insights into what investors really look for when evaluating potential investments.
One of the most striking revelations from Violetta's interview was her perspective on motivation. "I tend to have a red flag, which is money as motivation," she explained. "If you're doing the idea to earn money, this is the wrong place, because a startup doesn't have any money until the exit. Exit will happen like in five, ten years." This long-term view is crucial for entrepreneurs to understand—the startup journey requires passion and purpose that transcends immediate financial gain. Without a deeper motivation, founders often struggle to persevere through the inevitable challenges.
Violetta's journey into venture capital began when she was just 19 years old, and by 20, she was already working on her first deals. Her experience spans continents, having started in Belarus before winning a scholarship from the European Commission that brought her to Portugal, where she eventually led VC investments for two funds totaling 200 million euros. What makes her perspective particularly valuable is that she's been on both sides of the table—as both an investor and a founder of a startup that ultimately failed. "It's very important for any investor to have entrepreneurial experience," she emphasized, explaining that this dual experience helps her approach investments with greater empathy and understanding of the founder's journey.
Violetta Chekan, VC
When evaluating startups, Violetta looks far beyond just the business idea or product. For her, the team is paramount. Transparency, adaptability, and the capacity to learn and grow from feedback are the qualities she values most in founders. She described the investor-founder relationship as a "marriage," underscoring the long-term nature of the partnership. "Even marriages nowadays don't last like 10 years," she noted, highlighting the importance of carefully selecting business partners based on shared values and trust.
The conversation also delved into the specific challenges of blockchain and Web3 startups. Violetta, who focuses on B2B blockchain solutions with real-world applications, emphasized the importance of distinguishing between genuine traction and artificial hype. For B2B ventures, she looks for concrete evidence of market interest, such as pilot contracts, letters of intent, or commercial agreements. She cautioned against founders who claim to be "talking to" various companies without providing evidence of these relationships, describing this as an immediate red flag.
Another fascinating aspect of the discussion was Violetta's take on storytelling in the startup ecosystem. While she personally places less emphasis on narrative polish, she acknowledged its crucial role in a founder's success. "CEO has one role and has one skill to do—sales," she explained. This includes selling to investors to raise capital, selling to employees to build and retain a strong team, and selling to customers to generate revenue. Storytelling, she noted, is an integral part of this sales function. However, she clarified that the stories that matter to her aren't polished pitches but authentic explanations of why a founder started their business—the genuine passion and purpose driving their work.
Violetta also shared insights about her own podcast journey, revealing how it began as a way to overcome her fear of public speaking but evolved into a powerful learning tool. By interviewing experienced founders and investors, she continues to gain new perspectives and knowledge, demonstrating that even accomplished investors remain perpetual students of the industry.
For founders navigating the complex world of startup fundraising, Violetta's insights offer a roadmap to better understand investor psychology and build stronger relationships with potential backers. By focusing on transparency, adaptability, and authentic motivation beyond financial gain, entrepreneurs can position themselves for more successful fundraising journeys and stronger long-term partnerships with their investors.