My Favorite Mistake — 165: Entrepreneur and CTO Mark Herschberg Believed a Promise That Wasn’t in Writing

Author of The Career Toolkit.

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My guest for Episode #165 of the My Favorite Mistake podcast is Mark Herschberg, the author of the bookThe Career Toolkit, Essential Skills for Success That No One Taught You. Learn more at his book’s website. This is Mark’s 300th appearance as a podcast guest!

From tracking criminals and terrorists on the dark web to creating marketplaces and new authentication systems, Mark has spent his career launching and developing new ventures at startups and Fortune 500s and in academia.

He helped to start the Undergraduate Practice Opportunities Program, dubbed MIT’s “career success accelerator,” where he teaches annually.

At MIT, he received a B.S. in physics, a B.S. in electrical engineering & computer science, and an M.Eng. in electrical engineering & computer science, focusing on cryptography.

At Harvard Business School, Mark helped create a platform used to teach finance at prominent business schools.

He also works with many non-profits, including Techie Youth and Plant A Million Corals. He was one of the top-ranked ballroom dancers in the country and now lives in New York City, where he is known for his social gatherings, including his annual Halloween party, as well as his diverse cufflink collection.

In this episode, Mark shares his “favorite mistake” story about being promised something by board members that was not put in writing. What happened when a new CEO came in? Why was he fired from the product and engineering teams? What adjustments did he make to his approach with later companies?

We also talk about questions and topics including:

  • Was not spending on tech another short-sighted decision?
  • Book — lots of examples of mistakes in the book and the class he teaches
  • Tell us about the book?? The Career Toolkit, Essential Skills for Success That No One Taught You. — not just about new graduates?
  • Networking mistakes – he met Tim Berners-Lee and blew the opportunity to build a relationship
  • What are some of those essential networking skills?
  • Is it a mistake to sign confidentiality or non-compete clauses?
  • Negotiating mistakes? Don’t name a number first?
  • Ethical situations?
  • Your top 3 Halloween costumes?

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