Career and leadership strategist, MIT alumnus, and author of The Career Toolkit — on growing up in the 80s, choosing tech before it was glamorous, efficient negotiations, the psychology of business communication, what 700 first dates taught him about networking, and how to build a personal brand as an independent consultant
Mark Hershberg's second appearance on Be Yourself Podcast is a deliberately deeper conversation. The first time covered the essentials of career and leadership. This time, Serhii Beverly decided to stir the pot: he asked about Mark's early years in the 1980s, the formation of the internet in the 1990s, and the specific moment when Mark chose to connect his professional life to technology at a time when that choice was not considered glamorous or obviously correct.
What followed is the kind of conversation that happens when two people who both know how to listen decide to actually use that skill. Mark is a maestro of networking and sales, a man with a book called The Career Toolkit that covers the skills most professionals never formally learn, and someone who has thought carefully and publicly about what it means to build a career — and a life — with intention. He also, it turns out, has gone on 700 first dates. And what he learned from them applies directly to business.
Serhii marvels at conversations with people who know how to share unpopular yet supremely compelling opinions on a wide array of subjects. This episode is exactly that: career and leadership, the birth of the internet, negotiation psychology, the science of making people feel heard, remote work in the post-COVID era, and what it means to build a personal brand as an independent consultant — all from someone who has lived each of these things, not just studied them.
Mark Hershberg is a career and leadership strategist, CTO, MIT alumnus, and the author of The Career Toolkit — a practical guide to the professional skills that most people are never taught formally but that determine the trajectory of every career. He has spent decades working at the intersection of technology, leadership, and human communication, building expertise that runs from the early days of the internet in the 1990s to the modern realities of remote teams, personal branding, and independent consulting.
Mark is a genuine expert in networking and sales — not in the superficial sense of collecting business cards, but in the deep sense of understanding how human connection actually works, what makes people trust each other, and how to create relationships that compound in value over time. He has thought carefully about each of these areas and written about them, taught them at MIT, and applied them across a career that began before most of his peers understood why technology was worth choosing.
The 700 first dates are real. And they are relevant. Mark approaches dating with the same rigour and curiosity he brings to professional life, and the lessons transfer in both directions. He is also the creator of the Brain Bump app — a free tool for retaining the insights from books, podcasts, and conversations that would otherwise be forgotten within a week. Serhii Beverly describes talking to Mark as one of the most reliably stimulating experiences in the podcast's history: someone who holds unpopular opinions carefully, shares them clearly, and listens as well as he speaks.
again it was the 9s software was really growing we didn't use the word Tech startups yet but they were they were starting to be there in 1995 internet was times man of the year I think it was this is when it kind of came onto the scene I wasn't excited I wasn't moving towards it I was moving away but had to make a decision and I got a little lucky here because it turns out that was the right fit
interviewing is sales we are selling ourselves actually both sides are selling people miss this we know anything sales well I've got a product hey you should buy my product and here's why it's great when you're in an interview you should buy my product my product is me you should hire me I'm great
I do this as a passion project because my day job is fun building Tex startups this is fun for me in a different way I'm not worried about the money but it's a lot of work it's a lot of frustration don't think this is the magic way to riches it's a full-time job it's a lot of work and it may not give you the ROI