E21: From Building Startups to Betting on Them with Jason Gelman of Primary Ventures

In this episode of the Revenue Leadership Podcast, host Kyle Norton sits down with Jason Gelman, Operating Partner at Primary Ventures and Co-Founder of Jump, to explore his transition from operator to VC and the lessons he’s learned along the way. Jason shares insights from scaling Compass from $100M to $6B in revenue, why not every startup should raise venture funding, and how founders can navigate the challenges of go-to-market strategy. They also cover the evolving role of AI in revenue leadership, the traits that separate great CROs from the rest, and the fundamental mistakes many startups make when trying to scale.

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Primary: https://www.primary.vc/

Jump: https://jumprevenue.com/

B&T Infra Newsletter: https://www.infranewsletter.com/

LinkedIn: https://www.linkedin.com/in/jasongelman/

Contact: Gelman@primary.vc

Key Chapters:

(00:00) - Introduction to Jason Gelman and Primary Ventures

(02:46) - The Role of an Operating Partner

(06:03) - Understanding Jump: A Revenue Calendar Tool

(08:53) - Navigating Venture Capital: When to Raise Funds

(12:05) - The Transition from Operator to VC

(15:02) - Lessons Learned as an Operating Partner

(17:53) - Identifying Product-Market Fit

(21:06) - The Importance of Talent in VC

(23:57) - Final Thoughts and Future Aspirations

(41:06) - Navigating Venture Capital Networks

(44:00) - Insights from Operating as a Non-Venture Backed Company

(49:40) - The 'God of Beliefs' Framework in Investment

(53:01) - Mastering VC Relationships

(56:27) - The Rapid Evolution of Go-To-Market Tech

(01:01:09) - The Future of CRM and AI Integration

(01:06:20) - The Challenge of Investing in AI Startups 

(01:12:11) - Creating a Culture of AI Experimentation

(01:16:26) - Defining Greatness in Revenue Leadership