Shopify’s strategy: monetization beyond subscriptions

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Today’s show:

Nox’s new app RPLY reminds you to text your friends back, getting you to iMessage inbox zero.

On today’s TWiST, we’ve got Molly Cantillon of Nox, telling us how she plans to make lackadaisical texters (like our co-host Alex) more effective, even if it means breaking into Apple’s walled garden. Hear about how RPLY maps your relationships so that it can understand your messages contextually, and help you stay organized.

Then, Gregg Mojica of Alloy Automation swings by the show to dispel some common myths about AI agents. For the most part, these little machine learning helps aren’t truly autonomous… Hear how Alloy’s agents decide when it’s time to bring in a human for help. PLUS is AI in a “lull” right now? Hear why Gregg thinks there’s still a LOT of room for these apps to improve.

Finally, it’s another TWiST Flashback. We’re jumping back to 2013 for an eye-opening chat between Jason and Shopify founder/CEO Tobi Lutke. Hear some fascinatingly prescient takes on the rise of SaaS, how early Shopify differentiated itself from other ecommerce and website building solutions, AND why Tobi dreamed of making Ottawa a true tech hub.

Timestamps:

(02:57) Molly Cantillon of Nox is trying to help you get better at texting

(04:01) How RPLY gets even chaotic texters like Alex more organized

(05:10) The complexities of entering into Apple’s “walled garden”

(07:20) Keeping RPLY safe, in case you’re using it for work!(09:24) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(11:59) How RPLY uses relationship mapping to understand and prioritize your messages(19:23) Perspective AI - Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.

(21:08) Why Nox wants its AI to become “the Invisible OS.”(29:30) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.

(30:40) We’ve got Gregg Mojica of AI agent makers Alloy Automation

(31:42) How the rise of AI agents changed the core of Gregg’s business

(34:03) Why most AI agents still aren’t truly autonomous

(35:00) How Alloy’s agents decide when to bring in a human for help

(37:02) Why the rapid acceleration of AI development has made some enterprises pump the brakes

(39:00) Is AI in a “lull” right now? Why Gregg thinks there’s still room to improve.

(40:31) How close are we to AI apps going truly mainstream?

(43:41) Why Alloy Automation didn’t raise a massive round like so many of its AI peers? (Or are they?!)

(46:48) The difficulty of hiring in today’s AI landscape

(50:21) In today’s TWiST Flashback, we’re revisiting Tobi Lutke of Shopify’s appearance from way back in 2013!

(52:11) Why Shopify switched from selling snowboards to storefronts

(59:37) Turning Ottawa into a tech hub, and the “secondary market” theory

(1:05:32)The constant tension between growing your global footprint and expanding your features

(1:08:52)Who were Shopify’s actual rivals?