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I spent the weekend at a retreat (life update)

20 college-aged entrepreneurs in an Airbnb at an undisclosed location

In partnership with

Last week, I went on a My First Million sponsored weekend retreat with 20 other college entrepreneurs from the midwest.

Here are a few highlights:

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Friday, Nov 15th. I’m waiting outside my dorm building. I’ve got a backpack and a small duffle bag. I’m slightly nervous. Tommy, the retreat organizer didn’t share many details. It was a “F*ck it, let’s do it” decision.

A black Tesla pulls up. “Sup,” I say, putting my stuff in the trunk. I climb into the backseat. Two people are already there - five people total. It’s cramped. We leave, heading to an undisclosed location in Michigan.

The ride to the retreat takes roughly 7 hours, but it felt like much less. The entire ride we didn’t play any music, it was a non-stop, deep and broad conversation. We talked about what we expected out of the retreat, the difficulty of finding a spouse when you have ambitions and high standards, why we as a society are eating too many carbs, how touching receipts lowers your testosterone, how to get your product into the shelves of Whole Foods, whether joining a business fraternity is worth it, what the definition of religion is, and much more.

My first observation was how non-judgmental and curious everyone in the car was. These were individuals who wanted to learn what they didn’t know, not defend what they already knew.

One problem with driving a Tesla long distances is you have to charge it every so often. So we were a bit late. When we got to the Airbnb, we immediately dropped all our stuff and went to the backyard where there was a sand volleyball net, a sauna, and a lake. It was getting dark and cold.

“Alright,” Tommy said. “Everybody is going to, one by one, jump into this lake, introduce yourself, and explain what your life purpose is.”

What a way to start a retreat, I chuckled silently.

Later that night, we go to a local diner. There’s a long stretch of individual tables pushed together waiting for us. We sit and immediately the diner lights up with conversation. I order a taco salad… because who doesn’t like a taco salad?

There are 20 college-aged entrepreneurs. Many 3rd and 4th years, some dropouts, a few graduate students, and me… the only 1st year. But I don’t feel different at all. In fact, I feel oddly connected to them. There’s a underlying sense of anti-establishment. A “Things are wrong… and I’m going to do something about it” type of mindset.

We go back to the Airbnb and stay up ‘till 2am talking.

A few random notes I wrote down from different conversations:

  • Germs are friends, not foes. Carelessly taking antibiotics and using hand sanitizer is destroying the symbiotic relationship with you and your bacteria.

  • Waiting for serendipity is a form of laziness. Think about what you want, then go make it happen (don’t wait for things to magically come to you).

  • Conferences are underrated. You’re not paying for information, you’re paying for access to the right people.

  • People don’t remember books, they remember sentences. One of the reasons why Atomic Habits is so popular is because it has a high density of highlightable content.

  • Learning how to learn is the ultimate meta-skill. Then study the fundamentals of many disciplines.

  • Don’t let school interfere with your education. You should be reading books, starting projects, and building businesses alongside your studies.

  • Clear writing gives poor thinking nowhere to hide. The best communicators have written down their key points long before they ever give their pitch or speech.

  • Cynicism Safety Blanket. It’s easier to renounce what you don’t have than to admit you want it and aren’t doing the things in alignment with getting those things.

  • No phones/social media is incredible for your mental health. Are you checking because you need to check or because you’re bored?

Saturday, Nov 16th. It’s a slow morning. A few people go kayaking, a few explore the forest around us, while me and and the rest make breakfast (Eggs, pancakes, waffles, and blueberries).

Later, we gather outside on the porch for a yoga session. Everyone is still stiff from the long car rides. At the end, we meditate. At first, my mind is restless. There are so many ideas bouncing around in my head. I concentrate on my breath. I feel my chest expand, filling with a deep-seated gratitude and sense of love for the people around me. I had spent less than a day here and already I felt so connected to these people.

In the afternoon, we split up into groups of 2-3 and go on an aimless walk. There’s only one prompt: If you had to give a 5-7 minute TED Talk on any topic, what would you say? I walk with a finance content creator, a body builder, and a fitness trainer. Inevitably, the conversation turns to biohacking, which is a fancy term for changing your habits for optimal health. We talk about the importance of going slow on the eccentric portion of an exercise, the benefits of eating a pound of ground beef a day, how to optimize your sleep routine, and more.

Night rolls around and we’re all sitting around the living room on these comfy couches. The type of couches that sink in and make you never want to get up. Then, to my surprise, Tommy says, “Alright, we’re giving our TED talks now.” I feel a little shy. I have an idea of what I want to say from our afternoon walk, but who would want to hear from me?

Eventually my turn rolls around, and I shuffle my feet to the center of the room. “You got this,” my buddy Austin whispers to me, giving me a thumbs up. I feel better. I start my speech, and like magic I feel my body open up and my energy levels rise. I talk about the 4 components of the Viral Hook Equation (something Viral Content Vault customers have access to). After my speech, several people come up to me and say mine was “the best one”. How did you learn to public speak so well, they ask. It could be a superficial compliment, but it makes me feel good nonetheless.

At around 2am, we all gather around in a circle on the floor. There’s a single candle in the middle of the room, campfire style. Tommy calls this the ‘Problem Circle'. We take turns sharing a problem that’s top of mind for us and everyone chimes in to help solve that problem.

I didn’t have a problem to share, but I was curious about a question: How do you determine what ‘enough’ is? What’s the delicate balance between ambition and contentment? 

I tell them my North Star: A fit body, calm mind, house full of love, meaningful work, and enough wealth to not have to worry about it.

I won’t share the full conversation, but my favorite snippet:

“You can have everything just not all at once. So if your financial pillar is good, maybe think about focusing on the other pillars now (fit body, calm mind, house full of love).”

The reason why this resonated is because for a while now, I’ve been trying to justify why I’m in college to myself. I could be scaling the business. I could be traveling the world. I could be hanging out with other entrepreneurs down in Austin. Why am I in college?

And the answer was as simple as: Money is only one pillar of living the good life - and I’m working on the other pillars of my life.

It’s 6am now. The group is tired, but more connected than ever. We hug and shake hands, and then leave to make our way back to school.

If I had to summarize the retreat in one word, it would be: Intention.

So many people float through life, doing things just because everyone else around them are doing them. They’re like a jellyfish at the mercy of the current.

The people at this retreat were intentional with most of what they were doing.

They were okay with being labeled as “weird” or “different” or “excessive” because the pull of their vision was much stronger than any outside criticism.

What an incredible experience.

See you next Sunday,

Jay “Grateful” Yang

Ps. I love going to retreats and meetups like these for one simple reason:

Talent density.

There’s something magical about putting a bunch of driven, ambitious, genuine people together in a room and letting ideas percolate.

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