ToIRL May 2025

My top 17 event picks of May 2025

Welcome to the 31st edition of Toronto IRL - where we find the best IRL business + tech events in Toronto, and curate them, so you don’t have to go searching.

17 Events (Sorted by Date)

🙌 = I’m attending. 🙌🙌 = I’m the host
(Focusing on the events I’m personally attending this month)

🙌 May 3 - Hosted by Jai Mansukhani - Nice 5K run for tech/founders

May 3 - Hosted by Founders Running Club

May 7 - Hosted by Aman Desai - For healthcare and life science professionals

May 8 - Hosted by Elda Shawil

May 8 - Hosted by Aashima Asthana - For women creators

May 12 - Hosted by Aarij Khan

May 13 - Hosted by Derek Jouppi - At the amazing VClub!

May 13 - Hosted by Proof Poker - $150 buy-in 2-5

May 13 - Hosted by Canada Crypto Week - Free admission tickets this year

May 16 - Hosted by Andrew Yeung - I’m flying down to NYC with this one with a friend. If any other Canadians are there lets meet up at the conference.

🙌🙌 May 20 - Hosted by TechTO / Ryan Ing

May 21 - Hosted by Marsha Druker - Always a favorite!

May 21 - Hosted by Nia Pryce

May 22 - Hosted by Victor Li and Wendy Huang

🙌🙌 May 28 - Bringing this one back.

June 26 - Tech Roast Comedy Show is coming back, tickets range from $60-$100. If you want to speak or go up on stage, I recommend buying tickets closer to the front. If you raise your hand you can get on stage or speak on the mic like I did.

FYI! Toronto Tech Week is coming to Toronto in June. See more here

❤️Fav LinkedIn Posts of the Month

Alex Norman wrote an extremely insightful post about Brain Drain e.g. Canadians leaving to go work in the US, and the “boomerang effect” of them coming back - link

Nice troll post about sleeping in the office working 7 days a week - link

Ryan’s Corner - What Is He Up To?

Really cool story - least night went to an event and someone came up to me and said hey I love the newsletter. Said she’s been a long time subscriber. Glad to hear it makes a difference!

Cold Email

Besides that, I had success running my own cold email selling my own service.
900 leads and 9 positive replies.

I’m working on launching a new service offering as a LinkedIn Content Agency for B2B Founders. LinkedIn is just exploding with opportunity and there’s not a lot of experts. I’ve partnered with a professional content writer and she’s been ghostwriting for a guy and booking 200 demos a month.

Yup - 200 demos a month.

I think for anyone who sells to SMB, low ticket offer (<$4k) making 12 high quality posts/month and DMing 100-200 of a free case study is basically the best growth channel today. Founder-led marketing can take a business to $10M ARR before you need.

If you want to see my pitch (could always use the feedback) feel free to reply “linkedIn”

Toronto Event Organizers I Track For This Newsletter
RI.Events, TechTO, FuckupNights Toronto, Aceocial, Founders Poker, TodoToronto, TorontoEventHub, Startup Ecosystem Canada, Ryan Wong, Daivik Goel, Godwin Chan, Bitcoin Bay, Solana Toronto, Aniket Patel (EVP.VC), Clay.com, Kingsong

Newsletter Feedback
Feel free to email back here, I read and reply to everyone.

LinkedIn Version
If you prefer to get this newsletter on LinkedIn - click here