Episode 34

From Prosecuting to Leading In-house at a Tech Startup: S. Michael Lee, GC & COO at

Episode summary

Introduction: 0:00

  • Introducing S. Michael Lee, General Counsel & COO at, a generative AI/UX engine for creating multimedia experiences without any code.
  • Serving as counsel at many companies and law firms, including a role as GC at Blind, a platform that allows employees to anonymously share information with one another.
  • Spending 18 years as a prosecutor and regulator in the Santa Clara County District Attorney’s Office.

Honouring your connection to the Korean American community: 2:40

  • Viewing the United States as a mosaic, rather than a melting pot.
  • Working for a dry cleaner until your boss compels you to enter law school.

Finding inspiration in your community to work in public service as a prosecutor: 5:36

  • Looking to Hawaiian Japanese Americans for a model of how to integrate into American society.
  • Combating unconscious bias as the first Korean-American prosecutor in Santa Clara County.
  • Subverting the stereotype of the “angry Asian man” to persuade biased juries.
  • Taking negativity and reversing it as a force for good.

Applying lessons learned as a prosecutor to the private sector: 11:36

  • Comparing the responsibilities of a trial attorney to the role of GC at a small company.
  • Working as a jack of all trades to achieve your goals.

Finding an in-house role after building your career in public service: 12:57

  • Being met with confusion by people who don’t understand your interest in switching industries.
  • Framing your work in consumer protection as regulatory experience.

Advice to lawyers in government service trying to move into the private sector: 14:37

  • Building experience in various industries to receive training and learn what you like and are capable of doing.
  • Trying everything and taking every available opportunity to get trained in a new field.

Networking to advance your career: 16:57

  • Finding half of your jobs through introduction.
  • Maintaining a reputation as reliable so people hire you or share your information with others.

Dealing with layoffs at Blind: 20:40

  • Reaching out to your network and being honest with your network about your need for a new role.
  • Eroding the stigma surrounding layoffs in the tech industry.

Taking on a new GC and COO role at 25:04

  • Dealing with the excitement and challenges of the startup environment. 
  • Prioritizing creativity and flexibility in complicated and unique situations.

Advice to lawyers looking for new positions: 26:52

  • Refusing to limit yourself or impose glass ceilings on your career.
  • Taking on roles even if you don’t think you’re 100% ready for them.

Book recommendation: 28:19

  • The Bobiverse series by Dennis E. Tyler

What you wish you’d known as a young lawyer: 29:02

  • Not assuming you know where your career will be decades in the future.
  • Understanding that every new experience is preparation for the next thing.

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Tyler Finn
Head of Community & Growth, SpotDraft
S. Michael Lee

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