Nassir Criss of Sixty8 Capital joins us to share how defying the traditional VC path—and logging time in the trenches as a startup operator—made him a sharper, more founder-focused investor.

Before stepping into venture, Nassir had already helped build 15+ startups by age 22. That operational depth gives him a rare edge in early-stage investing: a real-world understanding of what it takes to bring ideas to life. This conversation dives into the gaps in the VC status quo, the value of founder empathy, and why endurance—not just intellect—drives success.

Here’s what’s covered:

• From Operator to Investor: Nassir’s Unconventional Path
• The Flaws in Traditional VC Gatekeeping
• Building from the Ground Up: Early Startup Lessons
• Why Founder Empathy Isn’t Optional
• Resilience vs. Hype: What Actually Matters
• Operating Across Sectors Before Writing Checks
• From Growth Equity to Early Stage: A Strategic Shift
• The Future of Venture: Who Gets to Be an Investor