I am currently working on 3 projects that I think are pretty cool so I wanted to share them with you.

This is for 2 reasons:

  1. I think these are very neat projects. And something that is nice about them is that they aren't something only I can do. So, if you wanted to, you could execute on them, in some capacity, in your own life.
  2. I've been struggling with procrastination on these projects. I'm hopeful that by putting these out there and adding a date, I will influence myself to complete the projects. πŸ™ˆ

Project Dos Equis

Who is the most interesting person you know?


For me personally, May 2019 - June 2020 was the worst time of my life. BUT, one of the big things that has helped me make meaningful progress out of the pit of hell I was in has been reconnecting with old friends, colleagues, and even meeting new people.

Convictional (i.e. Grouchy and Roger's company) planned to do an event in early September where you brought the most interesting person you now. They were calling it Junto after Ben Franklin's Junto.

In aggregate, these two motivations made me come up with the idea for Project Dos Equis (called Dos Equis after the Dos Equis' man who is "The Most Interesting Man in the World").

It's a very cool thought experiment though: who is the most interesting person you know? If you had to plan an in-person physical event, who could you bring who is the most interesting person you know? (that is geographically proximal to you) If you could bring anyone in the world (regardless of location), who would you bring?

So that's what I'm doing. I invited X number of people and asked them to bring the most interesting person they know. PLZ NOTE: Covid sort of messed this up happening in person so we are doing it virtually. We are going to use this software to facilitate.

PS: here's the icebreaker exercise we did which ppl really enjoyed.

Living Funeral

Why do we wait until people die to tell them how much they mean to us?

As mentioned, May 2019 - June 2020 was terrible. And one of the big things that helped me was reaching out to others. Prior to that, my main coping strategy for the persistent and unbearable anxiety and depression I was experiencing was as isolation and sleeping (and avoiding too).

I was isolating because I was so ashamed with what had happened and where I was at in life (getting fired from a small, fast-growing startup in San Francisco that was destined to go public). I didn't even want to talk to my closest friends because I felt like they were so much better than me (they went to Y-Combinator and raised money and I moved out to SF and got fired). There was no way I would leave the house in Sault Ste. Marie because then someone might see me and ask what I was up to (and I was very embarrassed and ashamed to tell them where I was at).

Something that helped me round the corner of depression and anxiety was reaching back out to people. I started to get validation that I wasn't the big piece of πŸ’©πŸ’©πŸ’© I thought I was (or, maybe, we are all just pieces of πŸ’© and it made me realize I wasn't different! I was part of Team Poop). This is one the of reasons I created the page Photos of calls with people.

Once I started reaching out to my network and getting that validation, I started reaching out to people who had inspired me to thank them. So many authors of books I have read and resonated with me. List of those Influences here.

The Living Funeral Project

I was reading β€œIt's Not About You: A Brief Guide to a Meaningful Life” by Tom Rath this summer (which was recommended by Shane Parrish's newsletter, Brainfo). And this was after I was starting to feel better. But there was a section that really resonated with me.

β€œI remembered something Don [Clifton] had said frequently when I was a child: he found it odd that we essentially wait until ppl die [i.e. funerals] to praise and celebrate all their contributions in life and β€˜fill their bucket.’”

β€œTell someone how they have contributed to your life...while they are still around to hear it.”

So that's what this project is. I'm writing to my top influences in my life to say a well-deserved thank you for them helping me to get to where and who I am today. πŸ€—

β€œIf I have seen further, it is by standing on the shoulders of giants.” β€” Isaac Newton

An additional note: it seems like there's a lot of bad shit going on in the world (at least, that's what social media and the news makes it seem like). So I think this is a great way to spread some good. Hopefully by taking the small time it takes to be grateful, I might make someone's day for thanking them for all that they did.

Pro Athlete of Everyday Life

Life is a game, I'm just playin' in the sand β€” Lil Wayne

I'm not a businessman, I'm a business, man, Let me handle my business, damn. β€” Jay-Z

Since Grade 7, I've thought school (and eventually work) was my "sport". I might not be the best at hockey or soccer or dating but I was the Dwayne Wade of school. πŸ˜ŽπŸ€“πŸ‘¨πŸΌβ€πŸ«

This perception of school as my sport was furthered when I read Mark Cuban's "How to Win at the Sport of Business" in university. And, then, at Shopify, we used to joke around about being Navy Seals of Sales and sleeping in barracks at the office.

So I have this background of perceiving school (and eventually work) like "my sport".


I find it very interesting that pro athletes take their health (exercise, nutrition, sleep, social support, etc.) so seriously but your average Joe doesn't. When I think back to the foods they served to us at Shopify and Notion, both very progressive companies, it was 😳(and obviously, my taste in foods didn't help! #FeedTheBarrel #HumanGarbagePail). And, when I think of investment bankers and lawyers that I know, I perceive they are eating meals on the go, limited sleep hours, etc.

Ultimately, I've started to work with a trainer, Kyla, who works with professional athletes. I told her that I wanted to become a Navy Seal for everyday life (or professional athlete). I've done training in the past, but it's usually been limited to physical / working out. Kyla, however, is putting me on a holistic approach: physical (stretching and eventually lifting (not looking forward to that)), eating, sleep, posture, etc.

I don't really like the term biohacking but maybe that's what I'm doing. It seems cooler to say that I'm striving to be The Tom Brady of Sales though! lol


Written: October 30, 2020