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Navigating a Career at the Intersection of Law and Technology

David Peinsipp, a partner at Cooley, has spent his career advising technology companies, founders, and investors — building a legal practice inside one of the fastest-moving industries in business.

Dave's career reflects a version of success that isn't defined solely by title or billable hours. Working alongside technology companies through growth, funding rounds, and major transitions requires staying genuinely engaged with an industry that changes constantly — which means continuing to learn even after reaching a senior level.

A central theme in Dave's approach is authenticity: building a legal career around real relationships rather than transactional ones, and being willing to say no when a deal or client relationship doesn't align with what matters to him. That discipline is part of what let him reach a point in his career with nothing left to prove, but everything left to gain from staying engaged.

For anyone building a career inside the technology industry — whether as an operator, investor, or advisor — Dave's experience is a reminder that long-term relevance in tech depends on staying curious and authentic, not just staying busy.

Key Takeaways

Build a technology career around genuine relationships, not just transactions
Know when to say no to preserve what matters most in your work
Stay engaged with an industry for its own value, not just for status or title
Long-term relevance in tech comes from continued curiosity, not tenure alone
Listen to the Full Episode View Dave Peinsipp’s Profile