Sometimes the greatest things come from serendipity.
I was walking on Santa Monica Pier when I saw Airrack filming a YouTube video. We knew each other because I had kayaked to ask for an internship on an island he was throwing a 1 million subscriber celebration on in Florida. But when I saw him all the way across the country I ended up having one of the most interesting experiences of my life.
I jumped off the pier with him in a video that now has 14 million views.
Or another time, when I tried kayaking to the back of Joe Rogan’s house but ended up meeting one of the largest concert promoters in the world at a backyard party in Austin. A year later I connected him to a good friend starting a music discovery technology start-up and he has become a valuable industry insider and ally for him.
Or another time, where I cold emailed book-tech start-ups I found interesting. This led to me joining the co-founding team of Peek, a social-reading app before it fell apart shortly after (the CEO left for another company).
Or yet another time, when I employed a similar cold email strategy, this time emailing two founders who connected me with an author they were working with. Her name is Emilia Rose. And together with Sean Patnode, we founded Ream, our technology start-up empowering authors to monetize their stories and superfans through subscriptions and for readers to find deeper belonging and relationships with the worlds they love.
And maybe the best story of them all, when in a ritzy hotel lobby in West Hollywood carrying a large pizza box with my college roommates (we were trying to give it to another celebrity we wanted to meet and strike a deal with) we met Reyna Ortiz, who at the time was the executive assistant to no other than Elon Musk. The conversation and eventual custom pizza we made for her (picture below) resulted in us snagging her phone number. And in the end, we gave away the pizza to the people of Venice Beach at midnight. There was a Dead Head knockoff concert happening with hundreds of homeless people on the beach dancing and the pizza ended up getting drugged with tons of shrooms.
The people did not seem to mind!
I still need to get around to editing and uploading these videos.
But that’s not why I’m writing to you today.
I’m writing to tell you that starting Friday, October 21st, from 10 am EST to 11am EST, I will be available to talk to anyone and will be doing this every Friday. A private conversation between me and you (you can invite friends too, but not necessary). We can talk about anything, with no expectations. A problem you are having in your life. Questions you have about mine. Your favorite books. Inside looks at my books in progress. Chats about my technology company… anything. I’ll do my best to help you and I look forward to learning and being enriched by all these convos.
And for fellow authors, entrepreneurs, or students, I’m happy to share any advice I can during this time that can help you.
You don’t need a warm intro. You don’t need to have met me in a past life. You don’t need to have any questions. Or you can have ten. The only catch is, each conversation will last only 20 minutes to maximize the landing space for serendipity during these 2 hours.
That’s right. We are back to that landing place for luck.
This language was inspired by a recent My First Million Podcast with Sam Parr, Shaan Puri, and Andrew Wilkinson. They talked about how the Venture Capitalist Brad Feld would sit in a coffee shop and allow strangers to book time with him. That’s when Shaan mentioned those very words “Landing Place for Luck” and “Surface Area for Serendipity”.
That resonated with me. In my weird life as an outgoing, risk-taking person who has been lucky enough to be at a place like Harvard where openly pursuing my passion for storytelling and futures leads to me going to an MIT Hackathon on a random night and meeting Machine Learning Engineers building something that reduces the time and complexity of producing a comic book by 95% — and they wanted me to help with their project (this was just last week).
Point is, without knowing it, I have a large surface area for serendipity in my life.
But often time things are filtered. Whether by the admissions councils of elite colleges, people who have the wealth to be in a certain hotel lobby, or running a certain company that I reach out to. All of that is great.
But — I want to introduce more entropy into this process. No gatekeeping. Anyone who has this link and resonates with me. That’s it.
So I look forward to seeing what conversations can come from this, making new friends, and ultimately, helping each other to live more boundlessly.
And in our own lives, it’s just as important to think — what % of my time can I allocate to serendipity? How can I embrace the randomness and uncertainty of the universe, and approach it with a hopeful, optimistic lens that the human collective has more uncovered beauty than we can ever know or imagine?
That’s it from me on this one. I’ll see you all soon, but in the meantime, don’t forget.
Together we are boundless.
