Dharmesh's Blackjack to HubSpot
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A story about Dharmesh Shah, founder of HubSpot, and his unique path before becoming a successful tech entrepreneur.
"When I was hanging out with Dharmesh, he told me these amazing stories. He said when he was in grade school or high school, he got in trouble because he just didn't go to school. I asked why and he said, 'Well, I had never seen a ping pong table and they had one of those in the dorm. Right when I saw it, I decided I'm gonna be the best at this.' So he dedicated his high school years to being the best ping pong player.
Then he casually mentions that he almost didn't even want to start tech companies because he was going to become a professional poker player. He and his brother were up mid to high six figures over their short career in blackjack. They learned how to play blackjack well, and they spoke a language that isn't very common in India. They could talk at the tables and discuss strategy and no one would even know. He said 'We could win, I'm up and I know how to do it the right way.'
He's now built HubSpot into a $20 billion company, but he's done so many unique things in his life that you wouldn't even know about. When he tells you these stories, you realize he's a lovely guy, but he's also kind of a shark - he wins at everything he does."
Sam Parr
Host of MFM and fitness influencer
Sam Parr is a serial entrepreneur and business media pioneer.
In 2016, he founded The Hustle, a business news media company that started in his kitchen with just $12 and grew to eight figures in revenue.
Sam led the charge in making newsletters popular when few believed in their potential.
After four successful years, he sold The Hustle to HubSpot, a publicly traded company. Now operating as HubSpot Media, The Hustle reaches 3 million readers daily, employs a team of nearly 100, and has been the launchpad for dozens of its staff to found their own media companies and newsletters.
Sam remains the host of the popular business podcast, My First Million, and continues to start and sell companies. He also co-founded Hampton, a highly vetted community for entrepreneurs, founders, and CEOs, and teaches people to write better through his platform, Copy That.