Glen Coates: Why Shopify Will Dominate Amazon; How Microsoft Made Smartest Move of 2023 | E986
Harry Stebbings (host), Glen Coates (guest)
In this episode of The Twenty Minute VC, featuring Harry Stebbings and Glen Coates, Glen Coates: Why Shopify Will Dominate Amazon; How Microsoft Made Smartest Move of 2023 | E986 explores shopify’s Product Chief On Beating Amazon, PM Frameworks, And Storytelling Glen Coates, VP of Product at Shopify, traces his unconventional path from game development to founding wholesale platform Handshake, which was later acquired by Shopify, and explains how those experiences shape his product philosophy.
Shopify’s Product Chief On Beating Amazon, PM Frameworks, And Storytelling
Glen Coates, VP of Product at Shopify, traces his unconventional path from game development to founding wholesale platform Handshake, which was later acquired by Shopify, and explains how those experiences shape his product philosophy.
He details Shopify’s shift from fragmented product lines to a more unified ‘Core’ organization, and introduces his outcomes–assumptions–principles framework to reduce misalignment and wasted work in large-scale product development.
Coates argues that Shopify’s long‑term edge comes from combining a powerful merchant platform, a high‑quality app ecosystem, and an emerging buyer aggregation engine (Shop), which together position Shopify to compete directly with Amazon.
He also shares candid views on leadership, managing up to a product‑centric founder CEO, the importance of narrative storytelling in product and fundraising, common PM mistakes, and why Microsoft’s AI strategy is the smartest bet of 2023.
Key Takeaways
Use an outcomes–assumptions–principles document to reduce product misalignment.
Before committing serious resources, teams should define how success will be measured (outcomes), what they believe about the world (assumptions), and clear decision rules for 51/49 tradeoffs (principles). ...
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Explicit principles prevent teams from tearing themselves apart over stakeholder tradeoffs.
Shopify routinely faces conflicts between merchants, developers, and buyers, or between small and large merchants. ...
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Storytelling is as critical as metrics for product leaders and founders.
Coates learned under pressure that investors and teams need a simple, emotional story they can repeat—like ‘we make sure the shirt is on the shelf when you want it’—not just process diagrams and TAM slides. ...
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Platform extensibility must deliver first‑party quality for third‑party apps.
Shopify’s app strategy only works if external developers can build apps as performant and polished as Shopify’s own features. ...
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Large platforms must think in 5–10 year horizons, especially at the bottom of the stack.
Coates’ Handshake misread how quickly the world would have ubiquitous connectivity, over‑investing in offline capability that became tech debt. ...
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Senior product leaders should ‘aim’ decisively, not default to pure bottoms‑up consensus.
Coates argues that products like Apple’s feel coherent because someone holds the pen for the whole suite. ...
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Great PMs optimize for decisions and outcomes, not process theater.
He criticizes PM culture’s over‑focus on frameworks and rituals, arguing the job boils down to making smart calls, working well with others, and reliably shipping valuable work. ...
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Notable Quotes
“At its base, product management is making good decisions about what to build and when.”
— Glen Coates
“If all the decisions are coming from the edges, the chance that it's all gonna work together and feel like it came from the pen of a single creator just goes through the floor.”
— Glen Coates
“If you do not tell someone a story that they can see themselves in and empathize with, you can say all the numbers in the world—no one gives a shit.”
— Glen Coates
“The best PMs have this feeling about them where it's like a freight train—if you try and stand in front of this thing, you're gonna get fucking flattened.”
— Glen Coates
“These days, I'd be fucking terrified to be competing with Shopify in commerce.”
— Glen Coates
Questions Answered in This Episode
How could the outcomes–assumptions–principles framework be adapted for much smaller startups without adding too much process overhead?
Glen Coates, VP of Product at Shopify, traces his unconventional path from game development to founding wholesale platform Handshake, which was later acquired by Shopify, and explains how those experiences shape his product philosophy.
Get the full analysis with uListen AI
What specific product moves does Coates believe will allow Shopify to ‘dominate’ Amazon over the next 5–10 years?
He details Shopify’s shift from fragmented product lines to a more unified ‘Core’ organization, and introduces his outcomes–assumptions–principles framework to reduce misalignment and wasted work in large-scale product development.
Get the full analysis with uListen AI
How should a non‑product founder practically ‘stay’ head of product without becoming a bottleneck as the company scales?
Coates argues that Shopify’s long‑term edge comes from combining a powerful merchant platform, a high‑quality app ecosystem, and an emerging buyer aggregation engine (Shop), which together position Shopify to compete directly with Amazon.
Get the full analysis with uListen AI
In a world where Shopify doesn’t own the top of the funnel, what bold strategies could it pursue to gain more direct access to buyers?
He also shares candid views on leadership, managing up to a product‑centric founder CEO, the importance of narrative storytelling in product and fundraising, common PM mistakes, and why Microsoft’s AI strategy is the smartest bet of 2023.
Get the full analysis with uListen AI
How can PMs balance being a ‘freight train’ for execution with staying truly open to feedback and changing course when evidence shifts?
Get the full analysis with uListen AI
Transcript Preview
The things that you love can be funded by Shopify technology. We make your life and your dreams possible.
That sounded pretty good.
Glenn, I am so excited for this. I've heard so many great things from your love of pad thai to your learning the drums.
(laughs)
I'm... Uh, this is just gonna be a fun show, so thank you-
Yeah.
... so much for joining me, man.
Uh, yeah. Happy to be here, man. Thanks for having me.
Not at all. But I wanna start with a little bit on you. So, how did you make your way into the world of startups first, and then come-
Mm-hmm.
... to lead the product org at Shopify today?
I've had a winding and weird career that just looks stupid on paper. But, um...
(laughs)
I, uh, I was a comp sci grad. I, I was a video game developer for three or four years. Um, I ended up in San Diego. Uh, basically one of my high school teachers asked me to move to the States and run, like, the US warehouse of his, him and his wife's eco-friendly shopping bag business, which was, I was like, "I wanna move to the US. Let's do this." And so I ended up in, in San Diego in a warehouse with forklifts whizzing around me and, you know, that kinda stuff. And I was like, "I was a video game developer a second ago. What just happened?" Um, and as part of that business, which did a lot of wholesale business, I ended up going to a lot of trade shows in New York and being on the floor of the Javits Center. And, you know, I would be writing orders in these order books for, like, when people would come to the booth and say, "I wanna have your bags in my store." And so after doing a bunch of these trade shows, I kept thinking, "Well, there should be an iPhone app for entering these orders." These writing orders in books thing is like a nightmare. And so after a while, there was no... I, I just kept thinking someone would build an iPhone app for this, and it, it just kept not happening. And so after a couple years of that, I was just like, "Fuck it. I'll just, you know, I'll just download the Xcode." I'll download Xcode. I'll learn Objective-C, haven't coded in a couple years. Let's go. And I built a prototype of what eventually became Handshake, which is just literally an iPhone app for entering orders at a trade show. I moved to New York around the same time, and then I... What happened? I basically applied to go to business school, went to business school, went for one day, and then I was like, "Actually, this is kind of not what I wanna be doing. I'd actually rather be coding 12 hours a day." And so I quit business school, and then I, and then Handshake just happened, and that's where I... You know, my old friend Mike Elmgreen came on board as my co-founder to run, um, uh, to run sales and marketing. I think you met Mike, and he's probably told you all the trash about me. Um, yeah.
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