70 Days Left in 2024

Hey Friends,

Happy October,

Welcome back to Stay Curious — a newsletter I write once(ish) per month to riff on a few things keeping me curious. I talk about startups, tech and other random things catching my eye.

Special thanks to M-Dohms for calling me out for skipping my September issue. Back to the laptop we go.

Here’s some things keeping me curious this month:

  • Lisbon/Paris/Copenhagen

  • A podcast I jumped on with Anne Riesling

  • A $400m story of persistence

  • Our latest LOI founder batch

  • a fun virtual pitch event this Thursday

  • Low stakes compliments for high stakes impact

  • an annual retreat with my cousins

  • Bad foundations = bad outcomes

  • Ben Lang’s newsletter

  • ChatGPT’s next iteration

  • Advice being dangerous when you don’t know your North Star

  • Planning 5pm weekday adventures

Here’s some double clicks if you wanna dive deeper:

1) 🇵🇹 I’m heading to Websummit Portugal in November and hitting up Paris and Copenhagen while I’m on that side of the pond. If you know any hidden coffee shops, restaurants or running routes, holler at your boi.

2) 🎧 I just finished a podcast with my friend Anne. Give it a listen here if you’ve ran out of netflix shows and wanna hear some random stories

3) 💸 Harry Stebbings started a little podcast project when he was 18. 10 years later, he’s officially announced a $400m fund. He’s a great example of what can happen when you’re persistent and dialled with your content. I sent him a text to congratulate him and this is what he said back:

4) ☕️ At LOI, we recently welcomed our largest cohort (almost 100 founders) to date. I wrote a bit about them here. If ay of you wanna raise your hand to be a guest speaker, mentor or just wanna watch them pitch in December, hit reply.

5) 🍿Almost 600 people are coming to this virtual pitch event with the founder of Thinkific and a few others on Thurs Oct 24th. Sign up here if you’re game.

6) 👋 Low-stakes compliments create the most powerful conversation openers. Ie. “love your shoes, did you just get a haircut, love how you designed this coffee shop etc”. Try ‘em out on your next meeting

7) 🎨 This last weekend, it down poured record-breaking rain in Vancouver. But that didn’t get in the way of having a great time. My cousin planned this amazing paint night for a group of 10 of us (video here) and it was a total blast. Highly recommend if you need a good rainy day activity.

P.S. Here’s a sneak peek of how bad of an artist I am. Picasso would be turning in his grave.

8) Advice is dangerous when you don’t know your North Star. Something I’ve been trying to be more conscious of when people ask me for advice is asking “what does your dream life look like in 5, 10, 20 years? etc. If you don’t know that, it can be easy to copy someone’s life plan that’s not actually going to make you happy. I’m especially inspired by Emma Eisenhauer who instead of jumping right into uni took a strategic gap year with Duke, and is travelling the world and blogging her way form one adventure to the next.

9) Looking for a new job? So are a few of my friends. Ben Lang (an early member staff at Notion and angel investor) has a great newsletter where he shares about under cover roles in tech from his network. Give it a skim.

10) ChatGPT’s next iteration is wild. This is a great visual that shows how big of a step the next evolution of ChatGPT will be. Thanks to R-Ironside for putting this on my radar.

11) Planning 5pm weekday adventures is a great unlock for folks or couples that work from home. My wife and I have been trying to do it more and we’ve found it’s such a good motivator to crush the afternoon work flow. Could be a trail walk, making homemade ice cream, visiting a friend — whatever it is — put it in the cal for 5pm and stick to it. You’ll be happy.

12) 3 signs you’ve had an awesome hangout: 

  • 1) you can have depth of range in the covo (humour, sadness, challenge, encouragement)

  • 2) you have more energy after the hangout than before

  • 3) you plan the next hangout on the spot before you leave (instead of just saying, can’t wait till our next hangout)

Those are my hot takes of the month. Which one did you like the most?

Hit reply and let me know.

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

Joel

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