The Long Rise

Let me tell you about the time I cried uncontrollably at a Maggie Rogers concert

In 2024, at MSG, Maggie Rogers took a mid-set break to walk us through her career. The bars and low-level venues. The small crowds. The years of playing for little money in front of mostly just her friends. Listening to an artist walk us through her rise was a special moment for her and for us.

She talked about being discovered by Pharrell almost a decade ago, and everything that came after. The slow climb. The growing following. Person by person. Brick by brick. Album by album.

At the end, she brought up Rock Band (the video game). The final level is always the massive stadium. She said that selling out MSG was her version of the final level. She’d imagined it her whole career.

And she did it twice that week.

We were all witness to her big moment (her “final level”). It gives me the chills again just thinking about it. Is there anything more beautiful than a decade of perseverance?

Whether I’m the protagonist or just a witness. I’m addicted to this feeling. Start low. Work hard. Rise. The longer the time horizon, the more it gets to me. Overnight successes need not apply.

It’s the same reason I can’t get through Rocky or The Pursuit of Happyness without losing it. When it comes to cinema, I clearly have a type.

When I look inward at some of my own journeys. I think about overcoming Dsylexai and eventually graduating Middlebury. Not making my third grade soccer team and eventually playing D1 and for the red bulls academy team. Graduating without a job and making partner at PeakSpan.

I’m currently ten years into my running journey with no end in sight. Importantly, these anecdotes are not just listed accomplishments, and they did not happen quickly. Each lasted 10+ years. That’s the point. The beauty is in the long, sustained effort.

While it’s a powerful reflection exercise for me personally, I get the most inspired when I see people I know on similar journeys.

I think about a friend grinding through the over-30 adult tennis leagues, watching his ranking slowly climb. My cousin, who achieved his dream of being a VC through pure hustle. I think about my friend who competes nationally in Olympic weightlifting. I think about the entrepreneurs I work with who have been building quietly for the last decade.

I think about all the ups and downs, the setbacks, the adversity. To see their hard work pay off after years and years of showing up. It gives me the chills, every time.

So whatever you're after, let me know. I'll be in the front row, popcorn in hand.