Lessons Learned from Professor Macklemore


When I saw the clip of Macklemore’s , with 4000 people singing along to his lyrics, and he having the time of his life, it was electric. I still get chills thinking about it. I then started to think: why does this have such an effect on me? It was pretty clear that I didn’t want to get up on that stage and rap (I had already terrified myself with stand-up); what I believe I connected with is the path I see Macklemore on:

  • Authenticity – to be comfortable with and to love who you are, and to express that fully
  • Purpose – to live up to your potential, to do the work that you are here to do
  • Value – to create something that is beneficial, helpful and of use
  • Service – to give back to others and to the world, to leave this place better than you found it

He’s also one of the most grateful people I’ve ever seen. Looking at his blog, Facebook page, or Twitter feed, most of his posts are thanks to his fans – he truly knows what part they play in all this. It’s a common practice for him to stay at the merchandise table until everyone has gotten a picture or an autograph or had the chance to talk with him – and this is after he’s already done a high-octane, unforgettable show!

I think there’s another reason Macklemore is so humble: it has not been an easy road. He battles addiction, something that sidelined him for a few years. Fortunately, he is now two years sober, more creative and productive than ever, and he knows people that haven’t been this lucky, who have lost that battle. Just check out his song “” for his chilling and amazing perspective. The writing on that track is brilliant.

Here’s one of his most recent music videos, for the song “Irish Celebration.”



With anyone that is doing something he loves, something he has been working at for half his life, Macklemore has a – the man is super playful and has a ball onstage, smiling throughout his show, making jokes, talking to the crowd and loving every second of it.

So what comes from embodying all this amazing stuff? Here are some of Macklemore’s accomplishments in the past month:

  • Performed at the opening day game for the Seattle Mariners, in front of 50,000 fans (and a TV audience)
  • Sold out every city on his first national tour as a headliner (and still going!)
  • His track “Otherside” has over 1,000,000 views on Youtube
  • Passed 25,000 30,000 fans on Facebook (hit this the day of this post)
  • AND he’s done all this without being signed to a label!

There is no sign of any of this slowing down either: he’s got major gigs lined up throughout the year, another album in development, and thousands of loyal, excited fans (I’m one of ’em).


There’s another layer to this story, though: not only is Macklemore a hero and inspiration to me – I feel blessed to call him a friend. It came from absolute serendipity, a story you can file under “you never know how things will turn out…”

Macklemore & Nathan

It all began in 1997, when my mother signed me up to help local senior citizens in the community with odd jobs: leaf raking, fence painting, and brush clearing. Into my life came a call from a retired, army brigadier-general, a man who had served his county for 36 years… and was also Macklemore’s grandfather. (That guy deserves his own post – actually, more like his own book!) My brother and I worked for the general for about five years, but I didn’t actually meet Macklemore until 2009 – 12 years later and across the country from where I grew up. Along with Macklemore, there’s his whole wonderful family, who are behind him all the way. It turned out to be worth the wait to meet all of ’em. :-)


One of the boons to traveling these days is seeing my friends. I was lucky to be in Boston last week when Macklemore was rolling through on the east-coast leg of his tour. It was actually the first time I had seen him live, and Youtube clips just don’t cut it. The show was AH-MAZ-ING, and so wonderful to see someone who is living his dream, doing what he loves, what he was born to do, and is so excited to share this with the world. (The pic of us above is from after the show – just a couple of Irish kids with tight-lipped smiles that betray how much fun we’re really having.)


Some of Macklemore’s stuff to check out:

  • His page, where you can listen to his music, watch his other videos and check out his performance schedule
    • Some of my fave tracks not listed here yet: Vipassana, My Oh My, and Wings
  • His BengalYucky site, where you can see what he’s up to and shop for merch
  • His page
  • His feed
Macklemore & Ryan Lewis

mack & ryan


Oh, so where did the title of this post, “Professor Macklemore,” come from? From the man himself. While in school, he was given an assignment to name a superhero, and that’s the one he chose.

Final note: Just as peanut butter isn’t the same without jelly, Macklemore also has a great partner: Ryan Lewis. For the sake of brevity, I used “Macklemore” above, but know that in most cases, it’s both of them (along with many others) who have contributed to the success.


I never considered myself a fan of hip-hop, but getting to know the man behind the Mack really changed my view of his music and the genre in general. Meeting him made the music a lot more of a personal experience for me.

What do you think of Macklemore’s music? How has meeting someone changed your view of their art?

I’d love to hear your response to that question and any other comments you have.

Until next time,