This week, Jason is joined by multi-platinum and Grammy Award winning rapper, songwriter, and entrepreneur Ben Haggerty, known to the world as Macklemore!

In March of 2023, he released his first new album in over five years titled Ben, which covers a portrayal of his life including topics such as his struggles with mental health. On top of his tour and new album, he is launching a collaboration with Adidas on his vintage inspired golf clothing brand called Bogey Boys which he started back in 2021. Entrepreneur, music, fashion icon, touring Europe, the United Stated and on top of it all, he is taking stakes in Seattle’s MLS and NHL teams, the Sounders and the Kraken.

Macklemore gives insight to his philosophy that has gotten him to where he is at, how priorities have shifted, his love of the puzzle that comes along with being an artist and creative, where he finds meaning, how getting sober and his parents helped him get out of his own way, and how divine timing and an underground strategy resulted in the success of “The Heist.” Macklemore also reveals what his original goal was at the start of his music career, how some of his diamond records were written in his parents basement, how he has never signed with a record label, the drastic difference between an independent contract versus signing with a label, how the numbers and money are just a small portion of the pie, and the importance of being rooted in the present. How much did he think “The Heist” was going to do the first week? What is a 360 deal? How does he measure success?

Macklemore reveals all that and so much more in another episode you can’t afford to miss!

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