Content
This page provides a collection of lessons, insights, and stories to help you lead with impact.
The Book
Lead Like The Boss is a practical guide to modern leadership — one that favors ownership over ego, clarity over chaos, and results over noise.
Inside, Andy shares real-world lessons from decades of building and leading high-performance teams. This book won’t tell you to “be inspirational.” It’ll show you how to make decisions, build trust, and lead in a way that actually works.
Preorder Lead Like The Boss
Conversations that Lead
5 Minutes With Andy
Leadership Insights
Quick hits on LinkedIn and in X for leaders who want to think sharper, act bolder — and Lead Like The Boss.
Get Andy’s unfiltered take on leadership and communication as he weaves in real-world stories and candid reflections on what it truly means to lead with intention.
Part observation, part inspiration. Always direct, often funny, and sprinkled with the occasional Springsteen reference.
Each post is designed to help you lead with more clarity, confidence, and connection.
Andy's Snapshots
Thank you from the bottom of my heart to everyone who came out to the book event at the @harvardclubboston. Never in my wildest dreams did I imagine I’d be sharing my story in a room full of such brilliant, generous, and supportive people. A special shoutout to the incredible team at the Harvard Club for hosting us with such grace and warmth, and to the friends and colleagues who helped pull every detail together behind the scenes. Particular thanks to Andy Freed – my Harvard water polo teammate, coach, and longtime friend – for this memorable night.
One of the biggest mistakes I see leaders make? They get tired of their message long before the team’s had a chance to hear it… let alone believe it. I’ve led teams for over two decades, and when I’m communicating something that matters, I don’t chase a fresh take every time. I come back to a simple framework: 𝟏 – 𝐄𝐱𝐩𝐥𝐚𝐢𝐧 𝐭𝐡𝐞 𝐰𝐡𝐲 𝟐 – 𝐄𝐱𝐩𝐚𝐧𝐝 𝐭𝐡𝐞 𝐡𝐨𝐫𝐢𝐳𝐨𝐧 𝟑 – 𝐁𝐞 𝐩𝐨𝐬𝐢𝐭𝐢𝐯𝐞 That’s it. Not flashy. Just clear. And it works → especially when you repeat it. Because people don’t need a new song every meeting. They need a chorus they can sing back to you. A message that feels familiar and true. I think about it like this: Springsteen’s played “Born to Run” 1876 of times, and he still performs it like it’s night one. Not because he needs to hear it, but because we do. It’s the same with leadership communication. The goal isn’t novelty. It’s clarity, connection, and trust. So if you’ve got a message that matters? Play your hits. Keep playing them. And if you’re curious how that concert mindset shaped the way I lead and communicate, I’ve been writing something on it. Lead Like The Boss comes out in February 2026. More to come. #LeadLikeTheBoss #LeadershipIsCommunication #PlayTheHits #SpringsteenFans
Today is my son Dan’s birthday.
Next week, he starts teaching English at Lawrence High School, a school with a 94% Hispanic student body and very real challenges inside and outside the classroom. It’s not a place where everyone would choose to teach. But it was where he wanted to be. Dan joined Teach for America because he believes in public service. He wants to make a difference where it’s needed most. That’s in his blood. His mom stepped away from her job at the Kennedy School to work on a presidential campaign. His grandfather, my dad, saved lives with small ideas that had big impact: the creation of the “H” hospital sign, and placed teddy bears in police cruisers to help calm kids at accident scenes.. And me? I’ve spent my career leading teams and trying to make my mark on political campaigns, at @virtual_inc._ , @tuftsmedicalcenter and beyond. But nothing makes me prouder than seeing my kids carry that spirit forward in their own way. Dan’s doing that now. He’s walking into a classroom full of young people, many of them navigating a new language and new challenges, and saying, “I’m here for you.” That takes courage. It takes heart. @springsteen has a song called Living Proof about the joy of seeing your hopes live on in someone else. That’s what I see in Dan. He’s proof that the desire to make a mark on the world didn’t stop with me. It lives on in him, in his sisters Rachel and Lauren, in the way each of them chooses to lead. But today, Dan gets the spotlight. Happy birthday, Dan. You’re already making your mark… and the best is yet to come. #LeadLikeTheBoss #Leadership #Teaching #Storytelling #Springsteen
Every summer, I make a stop at @edgartownbooks on Martha’s Vineyard. A few books for pure beach reading. A few to stretch my thinking. And always one or two that remind me what leadership should feel like. This little bookstore has quietly shaped how I recharge and reflect each year. That’s why I’m thrilled (and a little in awe) that come February, I won’t just be browsing the shelves, I’ll be on them. Okay… technically not me. The shelves couldn’t hold me. But they can hold a few hundred pages of what I’ve learned about communication, leadership, and showing up like the boss you were meant to be. Lead Like The Boss hits shelves in February 2026. It’s part Springsteen, part strategy, part standing ovation for the people who choose to lead with intention. Grateful to Edgartown Books for years of inspiration. Can’t wait to see my name on the spine. #Leadership #LeadLikeTheBoss #CommunicationIsLeadership #BookstoresMatter #EdgartownBooks
Springsteen isn’t a musician, he’s a poet.
That’s what @john_mcwhorther wrote in the New York Times last week. And he’s right. Heck, who am I to question one of the leading linguists in the country? He’s one of the nation’s top voices of poetry. I’m the guy that didn’t fully memorize Joyce Kilmer’s “Trees” in Mrs. Boersma’s 9-th grade English class. But here’s the thing. There’s more to a Springsteen show than the lyrics. And there’s more than the music. When I go to a Bruce show, I don’t hear the music. I hear and see a masterclass in leadership. It’s one thing to sing a song. It’s another to lead thousands of people who came for something bigger than music. 20,000 strangers who feel like they know you. A band of professionals who truly see you as The Boss, and respect you for it. You don’t get there by accident. You get there with intent. And there are lessons we can all take away. 𝐈𝐭 𝐬𝐭𝐚𝐫𝐭𝐬 𝐛𝐞𝐟𝐨𝐫𝐞 𝐭𝐡𝐞 𝐬𝐡𝐨𝐰 𝐞𝐯𝐞𝐧 𝐛𝐞𝐠𝐢𝐧𝐬 → the setlist is a roadmap. 𝐓𝐡𝐞 𝐩𝐞𝐫𝐟𝐨𝐫𝐦𝐚𝐧𝐜𝐞 𝐢𝐬 𝐬𝐩𝐨𝐭-𝐨𝐧 → nothing is left to chance 𝐄𝐯𝐞𝐫𝐲 𝐦𝐨𝐦𝐞𝐧𝐭 𝐞𝐚𝐫𝐧𝐬 𝐭𝐫𝐮𝐬𝐭 → until the audience—and his band—is ready to follow anywhere. When you walk into a meeting, do people lean in, or check out? When you close, do they know exactly where to go next? When they leave, do they feel like they were part of something worth showing up for? Because leadership, like a great concert, is never about filling time. It’s about moving people forward. And that’s what great leadership sounds like. This is just one of the lessons I explore in my new book 𝑳𝒆𝒂𝒅 𝑳𝒊𝒌𝒆 𝑻𝒉𝒆 𝑩𝒐𝒔𝒔. It’s available for pre-order now → http://LeadLikeTheBoss.com Grab your copy and start building your own leadership setlist. #LeadLikeTheBoss #Leadership #Communication #Storytelling #Springsteen
It’s that time of year.
Your inbox is no doubt filled with “out of office messages” from people on vacation. I bet you never read any of them. Because most out-of-office messages are where good communication goes to die. Generic. Forgettable. Deleted without a second thought. So years ago, I made a decision: Even the most mundane of communications can be attention grabbing and fun. That’s how the annual OOO video tradition began. What started as a playful twist on a mundane message has turned into something more. A reminder that every communication (no matter how small) is a chance to connect. A chance to show a little personality. A chance to make someone smile. This year’s version? Let’s just say there’s a paddleboard, a questionable shark encounter, and a few nods to my favorite summer thriller. (Apologies to Spielberg. And whoever had to clean up the goat cheese.) Because here’s the truth: If you want to lead, you can’t just inform people. You have to engage them. I’ll be out of office for a bit. No promises on shark safety. But if you email me, I hope you’ll at least smile. See you soon, Andy #LeadershipInEveryMessage #CommunicationMatters #OOOWithPersonality #MakeThemSmile
A billion mobile payments started with a name badge.
That name badge led to a successful meeting. That meeting brought the right people together.
And out of that moment, a global standard was born: 𝑵𝑭𝑪 𝒕𝒆𝒄𝒉𝒏𝒐𝒍𝒐𝒈𝒚. Which now powers billions of mobile transactions around the world. At Virtual, we see this kind of thing every day. Because behind every “big impact” story, there’s someone doing work that might seem small at first glance. → Preparing meeting materials → Coordinating members across time zones → Laying the groundwork for something no one’s built yet But none of it is small. It’s foundational. It’s meaningful. And it’s how industries move forward. Leadership means reminding your team of that, not just when the results are headline-worthy, but in the quiet moments, too. Because those are the moments people remember. That’s when belief gets built. #LeadershipIsCommunication #LeadWithPurpose #EveryMomentMatters #5MinutesWithAndy
For nearly 100 shows, I haven’t just been listening to the heart-stopping, pants-dropping, earth-shocking, hard rocking, booty-shaking, earth-quaking, love-making, Viagra-taking, history-making, legendary E Street Band. I’ve been learning something. About communication. About showing appreciation. About leadership. Www.leadliketheboss.com is released in Feb. Thanks @springsteen @stevievanzandt @realnilslofgren @mightymaxweinberg @jakeclemons @moniquemoore917 @officialrumbledoll @vamoalmonte @curtiskingmusic @ozbone @bdeep787 @saxophonist_eddie_manion @bdeep787 @estreetnation
Out-Of-Office Messages
Unexpected. Unforgettable. Andy’s out-of-office messages are anything but automatic.
Andy Freed on Stage
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