Sixteen Years to an Overnight Success & Walk Up to Jay-Z
My twin brother's band played to 15 people at the Mercury Lounge. A few years later they were up for two Grammys.
THIS WEEK'S THROUGH-LINE
Put in the years that are not glamorous. Then walk up and introduce yourself.
Welcome Note
Thanks for reading the forty-third issue of The Advantage. This one is brought to you by Proppel. Details on Proppel and the discount for Advantage readers are at the end of the newsletter.
My twin brother Mark started the band with Jess Carson and Cameron Duddy in 2014. He was 34. They went broke before they got signed. If you think you are too late to start, read this one.
The Practical Edge comes from the Grammys, where I spent every commercial break embarrassed for my brother.
If you are a founder doing $1 million to $40 million in sales and thinking about raising, reach out to us at Cutting Horse. Whether you want an investor or just advice from people who have been in your seat, we are glad to talk.
Mark is my twin brother, and he is also one of my best friends. We have gone through most of life together. We both became dads in our 40s, two weeks apart, and our careers took off on roughly the same timeline.
Their new album, Stages, is the one I keep going back to. I love it. The songs feel real, and it sounds like the true country they started with. Dean Dillon wrote "Marlboro Man," and they shot the video in Sonoita, our hometown, in a ranch truck Mark bought off the ranch it was left on.
WHAT I LOVED ABOUT IT:
The overnight success took 16 years. Mark counts from his first live gig at 20.
In 2014 they recorded for ten days at the Sonic Ranch studio in Texas. Cameron went to film it and came back the bass player. Then they went all in. I could not say much. I was knee deep in Freshly, living with Carter in a shitty place.
For close to two years there was no record deal. They paid their own way between Texas and Nashville and played Poodie's for beer money. Cameron had a mortgage, went completely broke, and called their manager, Matt Graham, right before Christmas to ask for help.
I saw them then at the Mercury Lounge in New York, a showcase for the labels. Maybe 15 people, mostly friends from LA. I bought the pizza after because I was the least broke of the broke people.
THE LINE THAT STUCK
"They say burn the lifeboats. But I always kind of felt like even if the lifeboat was burned, I'd swim back. I always find a way."
Cameron Duddy
He moved to Texas because it was the only place he could afford a house.
MY 20-SECOND RECAP
if you do not have the full 68 minutes
→Send the product instead of a pitch. They had no inroads in Nashville, so Cameron shot a video for "14 Gears" and they sent that. Mark: "It was our product. That's what we were selling."
→A hit is not a paycheck. The money is in touring, merch and placements. Mark calls touring "the most dangerous and the hardest part."
→Plan for the plateau. Mark compares music to golf. You get to a level, you stall, you learn the next skill. "That's not sexy. It's not glamorous."
→Do not put your name on something you would not drink. They spent three and a half years tasting batches in Mexico before Insolito went to market.
PRO MOVE
Figure out what your "14 Gears" video is. Make it, and send it to one person this week.
The year Midland was nominated for two Grammys, I went as the plus one and sat with the guys' wives. When the Grammys go to commercial, seat fillers rush in so no seat looks empty on camera.
Midland got up at every single break and introduced themselves to every celebrity in the room. I was dying. Mark comes back and says, "Dude, I just went up to Jay-Z." They were fans in the audience and did not pretend otherwise.
THE DATA SUPPORTS IT
In 2014, Nicholas Epley and Juliana Schroeder studied Chicago train and bus commuters. Commuters predicted that talking to a stranger would make for the worst ride. The ones assigned to do it reported the best one. Part of what kept people quiet was assuming the person next to them did not want to talk.
Erica Boothby and colleagues found the other half in 2018. After a conversation, people underestimated how much the other person liked them. They called it the liking gap.
HOW I USE IT
That night I stayed in my seat. I am not extremely outgoing, and walking up to people I do not know does not come naturally to me.
But when I decide on purpose to be outgoing, at a conference or wherever I am, good things keep coming out of it. I have to remind myself to do it all the time. It is something I still work on.
THE CHALLENGE
At your next event, find one person you would normally just watch from your seat. Walk over and introduce yourself, the way Mark did with Jay-Z.
Every business I have been part of came down to the people in it. Freshly, Petfolk, the ones that worked and the ones that did not. When people ask what a CEO actually does, my answer is that the real job is finding people who are better than you at the thing you hired them for. Jess said the luckiest break Midland ever got was Matt Graham showing up at their video shoot and saying he wanted to work with them.
I was a customer of Proppel before they were a sponsor. They specialize in marketing and operations, and they place talent from the US, LATAM, and beyond. Video editors, graphic designers, media buyers, and more out of LATAM. Managers, directors, heads of department, and VPs in the US.
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