Entrepreneur and CTO Mark Herschberg Believed a Promise That Wasn’t Put in Writing

Entrepreneur and CTO Mark Herschberg Believed a Promise That Wasn’t Put in Writing


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My guest for Episode #165 of the My Favorite Mistake podcast is Mark Herschberg, the author of the book The 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?

Scroll down to find:

  • Video of the episode
  • Quotes
  • How to subscribe
  • Full transcript

Find Mark on social media:

Watch the Episode:


"I certainly could have said,' I need an employment contract. I need a guarantee and put in writing.'"
"If you join an early-stage startup, even if they just got $10 million funding, there's no guarantee they're around in three years."
"One thing I've learned is when I take a new job [is to] wait a month or two [before updating your LinkedIn profile]" because you never know if it's really what they sold it as."

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Automated Transcript (Likely Contains Mistakes)

Mark Graban is an internationally-recognized consultant, author, and professional speaker who has worked in healthcare, manufacturing, and startups. His latest book is Measures of Success: React Less, Lead Better, Improve More. He is author of the Shingo Award-winning books Lean Hospitals and Healthcare Kaizen, as well as The Executive Guide to Healthcare Kaizen. He also published the anthology Practicing Lean that benefits the Louise H. Batz Patient Safety Foundation, where Mark is a board member. Mark is also a Senior Advisor to the technology company KaiNexus. He is also a Senior Advisor and Director of Strategic Marketing with the healthcare advisory firm, Value Capture.