Not Another CEO Podcast | Data-Driven Predictions - Vanja Josifovski - Kumo

Data-Driven Predictions - Vanja Josifovski - Kumo - Episode #87

February 17, 2026 / 54:24/E87

Can experience truly make a difference in the startup world? In this episode of Not Another CEO Podcast, David Politis speaks with Vanja Josifovski, Co-Founder and CEO of Kumo, to explore the journey of leading a cutting-edge AI enterprise.

From his prestigious roles at Pinterest and Airbnb to founding Kumo, Vanja shares the lessons learned, the dilemmas faced, and the excitement of turning vast amounts of relational business data into actionable predictions.

Takeaways:

The Importance of Co-founders: Vanja emphasizes the critical role of choosing the right co-founders. He stresses the importance of complementary skills and experiences that create a sustainable and successful leadership team.
Understanding Market Adaptability: A major challenge for technical founders can be the transition to understanding the go-to-market strategies. Vanja shares the struggles of innovating while aligning with market needs and effectively communicating product value.
The Journey From Idea to Reality: Vanja sheds light on how Kumo's idea sprouted from a simple yet groundbreaking aspiration to simplify the process of turning enterprise data into predictions without the complex machine learning cycle.
Raising Capital in the Current Climate: Although initially easy due to Vanja's background, he warns about the “honeymoon phase” in fundraising and the necessity of making money quickly, even when resources are abundant.
The Art of Unlearning: As Vanja continues his journey, he highlights unlearning as key to adapting to new challenges. The ability to let go of old practices and adopt new methodologies is vital for growth and evolution.

Quote of the Show:

“It’s always easier to watch somebody do things and criticize… if somebody’s watching you from the side, they’ll always find something wrong." - Vanja Josifovski

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