Andrew Gubskiy is a recognized person in the IT industry with over 14 years of experience, currently deepening his expertise as a Software Architect at Outbrain. His work involves developing advanced
Why Raising Too Late Kills Startups? In this episode of The Recursive Roundtable, we unpack one of the most misunderstood topics for founders: fundraising strategy — not just the “how,” but the when, the why, and the who.
GUESTS: Iliya Valchanov, Co-founder & CEO @ Juma Konstantin Bezuhanov, Co-founder & CEO @ Evrotrust Stoil Vasilev, Co-founder & CEO @ Paypercut
They share: 💡 why starting your fundraising too late is the #1 mistake seed-stage companies make 💡 how to structure your investor outreach like a sales funnel 💡 what separates “feature AI” from true AI-powered competitive advantage 💡 how to choose the right investor — not just the one with the biggest check 💡 terms, valuation, control and the long game of capital
You’ll hear real stories about: 👉 outreach strategy and KPIs (77 conversations ≈ 1 deal) 👉 managing rejection and staying confident 👉 the importance of building relationships long before you need capital 👉 why a bad partner can be worse than no partner 👉 practical negotiation lessons and term-sheet wisdom
Whether you’re gearing up for your first round or planning Series A+, this episode gives you the mental model and playbook you need to approach fundraising with clarity and confidence.
