Lucky Sage— from virtual care to real life relationships

Think a 5 day IRL Masterclass with a hero who’s great at exactly what you want to be great at. You get to live with and learn from a person you’ve long admired. They’re people you’ve thought you’ll never get to meet, but, if you’re accepted, you get to go on “vacation” with them, become actual friends, and absorb their wisdom. That's Lucky Sage.

Lucky Sage— from virtual care to real life relationships

Think a 5 day IRL Masterclass with a hero who’s great at exactly what you want to be great at. You get to live with and learn from a person you’ve long admired. They’re people you’ve thought you’ll never get to meet, but, if you’re accepted, you get to go on “vacation” with them, become actual friends, and absorb their wisdom. That's Lucky Sage.

Lucky Sage— from virtual care to real life relationships

Think a 5 day IRL Masterclass with a hero who’s great at exactly what you want to be great at. You get to live with and learn from a person you’ve long admired. They’re people you’ve thought you’ll never get to meet, but, if you’re accepted, you get to go on “vacation” with them, become actual friends, and absorb their wisdom. That's Lucky Sage.

The First Lucky Sage Event

The First Lucky Sage Event

The First Lucky Sage Event

The First Lucky Sage Event

In late 2024, I started Lucky Sage as a side project. Lucky Sage produces intimate events with legendary figures in the arts, health, and business. Our multi-day experiences bring together twelve skilled enthusiasts and one iconic figure for thoughtful conversations, delectable cuisine, inspiring venues, and healthy excursions in a charming town. Our mission is to foster genuine, real world relationships grounded in the realization that these legendary figures are, at heart, just like us—real people who inspire and encourage us to reach our own greatness.


Conferences are way too big and online Masterclasses are too impersonal. Real inspiration and real relationships come from meaningful time spent together with talented, passionate people having great conversations around dinner tables and campfires— free from distractions of your everyday life. Weeks like that…they change your life.


To keep all Lucky Sage experiences as high quality as possible, attendees must apply and prove they’ve got exceptional talent. This isn’t like paying extra to meet your favorite band in the VIP lounge.


With every startup, you start small, learn, and iterate. So, I was the guinea pig. The first experience was with me here in Boulder November 6-10, 2024 for folks who want to learn all about service design and product in digital health.

So what happened?

So what happened?

So what happened?

So what happened?

Denver’s 11th biggest snowstorm on record started November 6th. So did the first Lucky Sage. It was hosted at my house (and a few other houses) a few miles west of Boulder up in the mountains. The road to my house is a half mile of switchbacks up the side of a mountain. Fortunately, we got everyone up to the house before the big stuff hit, thanks to Adam’s truck. But that also meant we weren’t leaving until the storm stopped. Without a tank, there was no leaving. Sometimes stars align in the most unexpected ways— your private chef has the toughest Jeep Rubicon with the widest, biggest tires imaginable. He only got stuck for three hours once as he was going back and forth down the mountain to source ingredients and prep for the meals he served. One night, he couldn’t make it up and we had to raid our pantry and cook together. Eva, Neeraj, and Allison whipped up the best curry and German sausage stew you could imagine. All the curveballs made it magical. We were in a snow globe with 2 feet of powder hanging with a diverse group of inspiring, passionate people looking to learn as much as possible about how to build a digital health service. Chef Eric’s meals were off the charts. The hikes up the mountain into the clouds were simply stunning. We watched fawns born in the spring see snow for the first time. Each day, we had a morning and afternoon session focused on various aspects of digital health. And every single meal conversation was a combination of fascinating topics and lighthearted laughter. There’s no way I could have ever designed such a phenomenal experience with such wonderful, curious, smart people. The universe just aligns sometimes and I’m grateful for that.

Visit LuckySage to see upcoming events →