If recording one episode of my mid life crisis podcast at DotDev in Toronto wasn't enough, I got an email at 10.30pm at night saying that they had an extra slot open up. Kurt Elster, the OG of Shopify podcasting, wasn't able to make it, so they asked me if I'd fill the slot.

Obviously I said yes, and then I had to find someone to talk to. So I thought I should have some fun with it and do it my way, but wasn't quite sure who to have as a guest.

Then, I got chatting to this bloke after a DotDev session on AI Product Discovery, and it turns out we're both product data nerds. It turns out "this bloke" is Jay El-Kaake. Three time founder. Co-founded Smile back when it was Sweet Tooth, built and exited Fera.ai, and now he's running Osello, getting Shopify stores onto Nordstrom and Macy's.

We covered two main topics:
• Why 90% of "agentic optimisation" is stuff you should already be doing with your product data and content, and the value of taste when you're letting AI write your content.

• What it's like to be a founder in 2026. Jay is obviously a pro, I'm just starting out, so we shared our different perspectives.

This episode's brought to you by The Support Heroes, who support Shopify Apps all over the world.

And I would be remiss not to plug my own app, Product Pelican, which is helping stores enrich their product data for this new AI world.

This was the second Episode we recorded at DotDev, you can also catch our episode where we chat with Shopify's Head of Product Jonathan Zazove wherever you're listening to this.

YouTube Chapters

00:00 - Live from Dot Dev (definitely not a Toronto love story)
01:19 - From a refugee family's retail shop to falling for computers
02:44 - Osello: getting merchants onto Nordstrom, Macy's, Bloomingdale's and Target
03:05 - Why every marketplace "AI" claim didn't add up
04:22 - Where Product Pelican and Osello's pipelines meet
05:18 - Cleaning your data and building the pipe are two different jobs
06:16 - The Dot Dev talk on AI enrichment
07:42 - Buzzwords fade, fundamentals don't
08:27 - Why 90% of agentic optimisation is stuff you should already be doing
09:24 - The Hailey Bieber quote and the value of taste
09:57 - Why AI wants to feel human too
11:21 - Choosing a lane matters more than ever
12:25 - Hyper-niche apps, and why enterprise pricing doesn't scare people anymore
14:54 - Toronto's deep bench of founders
15:55 - Distribution is still the hardest part
16:45 - Your first customers should basically be your best friends
17:57 - Authentic video reviews over polished social proof
19:17 - Wrapping up