E92 - Avichay Nissenbaum (Founding partner, lool Ventures)

In this episode we speak with Avichay Nissenbaum. A serial entrepreneur turned investor, and the founding partner of lool Ventures. He built and sold two startups - SmarTeam (acquired by Dassault Systèmes) and Yedda (acquired by AOL) - before dedicating his career to backing founders. Lool Ventures has invested over $200M and helped shape some of Israel’s standout companies, including Beewise, NoTraffic, and Eleos Health. This conversation goes deep into the psychology of decision making, the emotional reality of investing, and the mindset that helps founders and investors navigate uncertainty. What We Dig Into: Pattern Recognition as a Superpower Avichay explains why VC is about seeing patterns long before they become obvious. He shares how reviewing 400–800 startups a year sharpens intuition, and why “sensor-tuning” is one of the most important skills an investor develops. He believes founders are often the ones who intuitively sense the future first. The AI Shift: Native vs. AI-Resilient Companies Avichay breaks down a framework every founder should understand: • AI Native - companies born on AI-first architecture. • AI Resilient - deep-tech companies that won’t get erased by the next Gemini or GPT feature drop. He calls AI “the biggest shift of wealth of our generation,” and explains why resilience matters more than hype. What Makes a Founder Fundable He is blunt about what truly matters: • Tenacity • Resilience • Skin in the game • Hunger • Ability to execute under pressure He calls this the capacity to survive a “roller coaster on steroids.” He also explains why lool Ventures loves bootstrappers and founders who have already built a minimal product before fundraising. The Emotional Reality of Investing One of the most insightful parts of the discussion. Avichay describes the difficulty of shifting from builder to observer. He talks about: • Seeing founders drive straight into a wall • Knowing the solution but not owning the steering wheel • Balancing heart and logic • Acting as an advisor, not a commander His analogy: “It’s like sitting next to the driver and you can’t touch the wheel.” The Role of Naivety Avichay argues that naivety is often a hidden advantage. It creates the space for original thinking, passion, and courage - the ingredients behind unconventional breakthroughs. His Entrepreneurial Beginnings We go back to the moment he left a stable career to build something new. At 25, with no entrepreneurial experience, he pitched a radical product vision to his CEO, was turned down, and decided to do it himself. He shares how: • Most early feedback was “no.” • The first yes arrived only after many rejections. • Passion and discomfort worked together to pull him forward. His clarity is powerful: “You don’t know. But something burns inside you.” 🎧 Why This Episode Matters This episode is a blueprint for founders, operators, and anyone navigating uncertainty. You’ll walk away with: • A clearer lens for evaluating opportunities • A mental model for understanding AI-era resilience • A deeper understanding of what investors really look for • Tools to stay grounded during the inevitable ups and downs • A rare, honest window into the psychology of early-stage investing It’s packed with wisdom. It’s grounded. And it’s one of those episodes that lingers. Enjoy your listen