Not Another CEO Podcast | Mastering the Slope of Learning - Nikhil Basu Trivedi - Footwork

Mastering the Slope of Learning - Nikhil Basu Trivedi - Footwork - Episode #73

November 11, 2025 / 39:17/E73

How do the best founders learn faster, think deeper, and turn that mindset into companies that endure for decades?

In this episode, host David Politis sits down with Nikhil Basu Trivedi, Co-Founder of Footwork, one of Silicon Valley’s most respected early-stage investors. Nikhil’s career spans both sides of the table, from co-founding Artsy, the groundbreaking online art platform, to investing in category-defining companies like Canva, Lattice, Frame.io, and The Farmer’s Dog.

Nikhil shares how he evaluates founders, why the “slope of learning” is the most important quality he looks for, and how he builds long-term partnerships based on trust, curiosity, and shared ambition. He also opens up about the changing venture landscape, the hype and opportunity of AI, and what it means to be an investor who has truly walked in a founder’s shoes.

Understanding the Importance of Learning: Nikhil emphasized the significance of the "slope of learning" in evaluating founders. This refers to a founder's ability to quickly learn and adapt to evolving market conditions, especially in the fast-paced AI era.
Making a Lasting First Impression: According to Nikhil, the first few minutes with a potential investor are critical. Whether it's 15 or 30 minutes, founders must capture the investor's attention and highlight their vision's potential.
Pitching with Conviction: Nikhil advised founders to clearly articulate why their business has the potential to be massive. It's crucial to strike a balance between ambition and grounded reality.
Value of Ongoing Communication: Post-investment, Nikhil stressed the importance of maintaining regular communication between founders and investors.
Leveraging AI for Better Investments: Footwork has been proactive in using AI to manage and analyze portfolio companies, allowing them to track company progress and trends efficiently.
Empathy from Experience: As a former operator and founder, Nikhil shared his belief that empathy is crucial in the investor-founder relationship. Understanding the challenges founders face allows investors like Nikhil to be better partners, offering thoughtful guidance rather than prescriptive advice.

Quote of the Show:

“In the first 30 minutes with a founder, I’m trying to assess their slope of learning… We invest in slope, not just smarts. How fast a founder learns matters more than what they know on day one." - Nikhil Basu Trivedi

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