In this episode of Notes to My (Legal) Self®, host Olga V. Mack speaks with Rina Wang, former Assistant General Counsel at AI startup Prepared, about what it really means for lawyers to build a career inside venture-backed startups, especially during periods of uncertainty, hypergrowth, and rapid change.

Drawing from her journey across litigation, multiple venture-backed startups, and a recent acquisition by Axon, Reena offers a candid perspective on what lawyers should expect when they step into startup life.

Together, they explore:

• Why uncertainty isn’t a flaw of startups; it’s a defining feature

• How one year in a startup can feel like 10 years in a Fortune 500 company

• What it means to make career decisions with limited information

• How lawyers can shift from risk-avoidance to value creation in fast-moving environments

• Why startups force accelerated learning, leadership, and personal growth

If you’re a lawyer considering a move into a startup or questioning whether speed, ambiguity, and change are worth the tradeoff, this conversation offers an honest look at the realities behind the hype.

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