From Start-Up to Grown-Up

#104 Issac Evans— How a Series D CEO Found Product-Market Fit, Stays Self-Aware, and Survived His Bank Melting Dow

• Alisa Cohn • Episode 104

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In this episode, Alisa Cohn interviews Isaac Evans, co-founder and CEO of Semgrep, a startup giving security tools directly to developers. Isaac shares his journey from conducting research at the U.S. Defense Department and MIT Lincoln Laboratory, where he explored binary exploitation bypasses, control-flow integrity, and novel hardware defenses on architectures like RISC-V, to founding and leading a fast-growing company at the forefront of developer security. A graduate of MIT with BS and MS degrees in EECS, Isaac also brings a deep curiosity for next-generation programming languages, secure-by-design frameworks, and the intersection of cryptography and public policy.

Together, Alisa and Isaac dive into the realities of startup leadership, the evolution of Semgrep’s business model, the value of feedback, and the transition from founder to CEO. Isaac offers candid insights on managing a growing team, navigating change, and staying grounded through self-awareness. The conversation also explores how AI is reshaping software development, concluding with advice and reflections for aspiring founders building companies in today’s fast-moving world.


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Timestamps:

(00:00) Introduction to Deep Conversations

(01:55) Exploring Love Languages in Relationships

(06:00) The Founding Insight of Semgrep

(10:06) Navigating Early Startup Challenges

(13:45) The Evolution of Semgrep's Business Model

(17:53) Handling Community Feedback and Criticism

(21:54) Crisis Management and Personal Growth

(25:46) The Importance of Feedback Culture

(33:20) Embracing Feedback as a Gift

(35:45) Shifting Leadership Styles

(38:32) The A-Plus Responsibilities of a CEO

(42:34) Navigating the Founder to CEO Transition

(46:46) Learning Through Experience

(50:32) The Challenge of Team Dynamics

(54:31) The Future of AI and Security

(59:28) Imposter Syndrome and Self-Awareness

(01:03) 15 Advice for Aspiring Founders

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