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Jeff Hoffman: My Unexpected Masterclass in Entrepreneurship

itschavah

Updated: Jan 26


Jeff Hoffman

I have had the fortune of working with some pretty heavy hitters in the business world throughout my career but I will say, this past year, I had the rare privilege to work with one of the greats, who I’ll admit,I didn’t even know until this year!  


Before this year when I took on a new gaming/entertainment project - I’d never heard the name Jeff Hoffman (sorry if you’re reading this Jeff!). 


As I’m writing this I know that many of you have never heard the name either. 


But even though you may not be familiar with the name - believe me - you know Jeff. 


Ever use the kiosk at the airport to print your plane ticket? Then you’ve touched Jeff’s work. 


Ever used Priceline.com or Booking.com? Also, Jeff. 


When you think of someone who’s really got the Midas touch in business, Jeff Hoffman should be one of the first names that come to mind. 


Priceline.com and Booking.com pretty much revolutionized how we book travel today. But what’s interesting and refreshing for me is Jeff isn’t just about building successful companies; he’s about making a SERIOUS difference, and let me tell you, he’s had a huge impact on me, both professionally and personally. Neither of which was something I expected in the beginning. 


I had the privilege of working with Jeff during my time as the Chief of Staff and then COO of the Global Gaming League (GGL). 


We didn’t work together every day—he was the chairman of the board, so he had a lot on his plate—but every interaction we had was packed with wisdom, stories, and insights that I still carry with me today. 


He is awesome and I wanted to take some time to share so more people get to know the name Jeff Hoffman. 

Jeff Hoffman

From Humble Beginnings to Complete Industry Disruptor


Let’s kick things off with a little backstory on Jeff. He didn’t just wake up one day as a successful entrepreneur, rich family, or any of that; his journey was filled with curiosity, problem-solving, and a relentless drive to create meaningful things. 


His early ventures were the seeds that would grow into game-changing companies but what I love is Jeff shares his losses just as openly and vividly as he does his wins. But when he wins, he definitely knocks it out of the park…


Take Priceline.com. Jeff didn’t just create another travel website; he came up with a whole new way for people to book their travel—by naming their own price. This idea didn’t just disrupt the travel industry; it flipped it on its head. Suddenly, travel became more accessible and affordable for everyone, and Jeff’s vision made that possible.


And then there’s Booking.com, another jewel in his entrepreneurial crown. Under his leadership, it became the go-to platform for travelers worldwide. What’s so impressive about Jeff is his ability to see where the market is heading and understand what people really want before they even know it themselves. That’s a rare talent, and it’s what sets him apart as a true visionary.


Now, onto my experience with Jeff at GGL. Like I said, we didn’t work side by side every day, but when we did connect, it was like getting a mini-MBA in entrepreneurship. Jeff’s approach to leadership is something I really admire. He’s not just focused on the bottom line—though he’s pretty good at that too—but he genuinely cares about the people he’s working with and wants to see them succeed in roles that MAKE SENSE for them, not just roles that “make sense” on paper. I think this is a major key that most executives are missing. 


Problem solving and doing things that may not be popular but ultimately move the needle is the name of the game in business. He and I definitely share this sentiment which is easier said than done. 


So many people in leadership lack that gift of pulling back, taking out their personal feelings or attachments and doing what’s genuinely best for each company as a whole. Every decision that was ever brought to Jeff was looked at from a holistic perspective and dealt with in the most objective way possible. 


As great of a problem-solver, the thing that stuck with me the most was the way Jeff shared his experiences. Failures and triumphs. Failures more times than wins.


He’s got a treasure trove of stories—some funny, some challenging, but all incredibly insightful. 


He’s faced his share of obstacles (as we all have) but listening to him talk about scaling startups or navigating tricky situations felt like getting a behind-the-scenes look at how real behemoth businesses are built.


Happy to have had the time to work with someone so remarkable and share his name with people that may not know him. 


If you don’t know, now you do. 


As always - here for the disruptors, the changemakers and the LIT at heart. 


-Chavah


Jeff Hoffman


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