Breaking Into Sports
The Real Guide to Landing Your Dream Job
Everyone loves sports. Almost nobody actually gets to work in it. The gap isn't passion, everyone applying has that. It's knowing what actually gets you hired, and no one ever explains that part. I spent a decade learning it the hard way, working for teams like the Suns, Giants, Orioles, and Guardians, piecing together lessons no career fair or LinkedIn post ever taught me.
Breaking Into Sports is the playbook I wish I had starting out. It's not theory; it's what really works: how to network without it feeling transactional, how to survive the brutal early years of long hours and entry-level sales, and how to turn a foot in the door into an actual career. Add in insights from over 250 people who've done it, including Rob Manfred and Sam Kennedy, and you've got the roadmap nobody hands you until you already need it. Now it's your turn to take the field.
What People Are Saying
"Stuart's insight into the ever-changing world of sports gives young people the perspective and confidence they need to move forward. The sports industry can be challenging, but with the right guidance, it becomes a place full of opportunity. Stuart understands not just the business of sports, but the people in it, and that's what helps students navigate their own path with purpose."
— Annie Meyers Drysdale, Olympian, Basketball Hall of Famer, Only Woman to try out with an NBA Team
"Stuart's journey from intern to industry professional embodies everything this book teaches. I've watched him navigate the challenges of breaking into sports with persistence, authenticity, and genuine relationship-building. What sets this book apart is that Stuart isn't theorizing, he's done it, through internships and a decade of real experience. He understands what it actually takes to go from loving sports to working in sports, and he knows how to explain it in a way that gives students actionable guidance they can use immediately."
— Alan Nero, Managing Director, Baseball, Octagon
"I've known Stuart since he was trying to break into the sports industry, and what he writes in this book is what he's actually lived. Think of it as a diary about how to get in, how to progress, and how to succeed in this business. This isn't theory, it's the real path he took. Stuart didn't just observe the industry from the outside; he worked his way through it, made the mistakes, learned the lessons, and figured out what actually works. That experience shows on every page."
— Pat O'Conner, Former MiLB PresidentAbout Stuart sokoloff
Stuart Sokoloff has spent over a decade building a career in professional sports, working in ticket sales, corporate partnerships, and fan engagement for over eight professional organizations. His path started with 16 internships and professional experiences at Springfield College, where he also teaches sales and client services. He's also worked internationally with the Israel National Baseball Team, including preparing the team for the 2020 Tokyo Olympics and at the 2023 and 2026 World Baseball Classic. Stuart is a proud Maryland native, and when he’s not selling or writing, you'll probably find him exploring a national park or hunting down the best local restaurant in whatever city he's landed in.