Embracing the Cringe

Happy 12th Tuesday of 2026,

I’m at YVR airport this morning, but it’s Tuesday — so I’m cranking away on this newsletter as I wait to board my flight to NYC.

Yes. Welcome back to Stay Curious — a newsletter I write once per week on 3 things keeping me curious, or I send one of you a 100 dolla bill for catching me if I skip

Here’s what’s on my mind this week:

1. Embracing The Cringe

The most dangerous thing that can happen to someone like me working at a startup accelerator and venture fund is the “c” word. Getting “Comfortable”.

So to tip the odds and put myself back in the arena, I’m embracing the cringe and working on some side projects. One of them being a 1-day LinkedIn Masterclass April 24th.

Sure, part of this is to help pay for my excessive flights, but 99% of this is because I wanna help founders, builders, and operators share their story. The math is:

  • 1B+ people are on LinkedIn

  • Only ~1% actually post content

  • The average user makes over $75,000

  • 6 people are hired every minute

  • Over 100 million messages are sent daily

  • and the weirdest part - only 1% of users post content weekly

My goal with the LinkedIn Masterclass is to teach people how to become daily content creators on LinkedIn to create more opportunities for themselves, their startup and/or their side projects (angel investing, charities, coaching etc)

Since ya’ll are day 1 newsletter subscribers, I made a 40% off coupon code that’ll expire in a week. If you wanna join the 3 hour masterclass April 24th, sign up here

Have you heard of Allison Ellsworth or Poppi? If so, keep reading.

Our team at LOI secured a virtual zoom call fireside chat with her on April 1st @ 1230pm PST.

If you’d like to join and hear how she went from being laughed out of farmers’ markets to selling for $1.95B, join here.

Ever heard of Wealthsimple or Microsoft? Well, we’re hosting an event with them May 25th in Toronto and it’s already got a 200 person waitlist.

If you’d like to join, sign up here and email me. I’ll do my best to get you in but no promises as it’s gonna be a hot one.

Liked today’s deep dive? Forward it to a friend.

Joel

You can hit me up on Twitter or LinkedIn. But the true besties hit me up on Strava and IG.

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