In this episode of The CTO Show with Mehmet, I sit down with Rob Matzkin, a serial entrepreneur, investor, and connector who has built and exited multiple companies and now advises startups on scaling, fundraising, and execution.
Rob shares the hard truths of entrepreneurship — why execution beats hype every time, what founders get wrong about investor readiness, and how AI is reshaping startup moats. We also dive into founder burnout, the myth of overnight success, and the importance of building authentic relationships.
Key Takeaways
• Why most founders are not actually investor-ready
• How to show traction and de-risk your pitch to investors
• The double-edged sword of AI in fundraising and positioning
• Why execution > ideas (and how to prove it)
• How to avoid burnout and build a sustainable founder journey
What You’ll Learn
• The stages of fundraising explained clearly (friends & family, pre-seed, seed, Series A)
• The signals investors actually look for — beyond hype and storytelling
• How startups can think about moats in the age of AI
• The role of vulnerability and authenticity in leadership
About Rob Matzkin
Rob has founded and led 16 different companies, with multiple exits across sectors. Today, he consults founders on reaching product–market fit, scaling to millions in ARR, and navigating capital raising. He is also the host of the Purpose-Driven Summit and a recognized global connector across business, sports, and the arts.
https://www.linkedin.com/in/rob-j-matzkin-06027634/
Episode Highlights
• (00:04:50) Why founders think they’re unique (but they’re not)
• (00:09:30) The truth about being “investor-ready”
• (00:14:00) Risk vs reward: how investors really decide
• (00:22:00) AI hype vs real AI companies — what matters now
• (00:30:00) Product–market fit and why most founders misunderstand it
• (00:33:30) Burnout, balance, and the myth of working 16-hour days
• (00:44:30) Why most public stories about success are PR illusions
