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Dev Interrupted Podcast Episode Summary
Episode Title
Forget vibe coding. Say hello to vibe entrepreneurship. | Shopify’s Andrew McNamara
Episode Overview In this episode of *Dev Interrupted*, hosts Andrew Zigler, Ben Lloyd Pearson, and Dan Lines engage with Andrew McNamara, Director of Applied Machine Learning at Shopify. The discussion centers around the emerging concept of "vibe entrepreneurship" and the innovative tool Shopify Sidekick, designed to support e-commerce merchants by functioning as an AI co-founder.
Key Highlights
Introduction to Vibe Entrepreneurship
- Concept Definition: Vibe entrepreneurship refers to a more intuitive, less structured approach to starting and managing a business, focusing on creativity and ideas over traditional business practices.
- Transition from Vibe Coding: The term builds on the previous notion of vibe coding, highlighting a shift in how entrepreneurial success is approached through AI tools.
Shopify Sidekick
- Functionality: Shopify Sidekick is an AI co-founder that assists merchants in running their online stores by providing expert advice and automating various tasks.
- User Empowerment: The tool aids in crafting logos, generating themes, and extracting actionable insights from store data, thus accelerating merchants' paths to success.
- User Base: Sidekick caters to a diverse audience, from small business owners to large corporations. It enables new merchants to reach their first sale quickly and provides deep analytics for larger enterprises.
Insights on Building Trustworthy AI
- Importance of Evaluation Systems: McNamara emphasizes that having a robust evaluation (eval) system is crucial for building trustworthy AI. He discusses the pitfalls of merely relying on "vibe testing" rather than thorough evaluations.
- LLM as a Judge: The innovative approach of utilizing language models (LLMs) as judges can help in accurately measuring the performance of AI systems by focusing on user satisfaction rather than just feature execution.
Discussion of Industry Trends
- Economic Impact of AI on Software Innovation: The episode kicks off with a special report on GitLab’s findings regarding the economics of software innovation and the role of AI in improving productivity across organizations.
- C-level Executives' Perspectives: Insights from a GitLab report indicate a desire for balanced human-AI collaboration, but there are differing views on the actual current state of AI integration in workflows.
Key Arguments and Insights
- Polarizing Views on AI Investment: There’s a divide between executive perceptions and the experiences of individual contributors regarding AI productivity.
- Bus Factor Discussion: The conversation touches on the concept of the bus factor—a measure of knowledge retention within a team—and how AI could lead to a "bus factor of zero," where no single individual possesses crucial knowledge, potentially jeopardizing projects.
- Emergent Use Cases of AI: The hosts discuss how users are creatively utilizing tools like Sidekick to perform complex tasks and share their experiences, fostering a community of prompt engineering.
Conclusion and Future Implications
- AI as an Enabler: The potential for AI to democratize entrepreneurship is significant, allowing individuals without traditional business expertise to launch and manage successful ventures.
- Role of Humans in AI-driven Businesses: Despite the rise of autonomous capabilities through AI, human judgment remains critical in guiding AI and making creative decisions.
Resources Mentioned in the Episode
- [Shopify Sidekick](https://www.shopify.com/magic)
- [GitLab's Software Innovation Report](https://about.gitlab.com/software-innovation-report/)
- [Andrew McNamara's Talk at ICML](https://icml.cc/virtual/2025/46781)
Call to Action Listeners are encouraged to explore Shopify Sidekick, reflect on the implications of AI in their own work, and consider the evolving landscape of entrepreneurship in the AI era.
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This summary captures the essence of the episode, highlighting the key discussions and insights shared by the hosts and their guest, Andrew McNamara. It serves as a comprehensive guide for those interested in the intersection of AI, entrepreneurship, and software engineering leadership.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:05Welcome to Dev Interrupted. I'm your host, Andrew Ziegler. And this week we're bringing Andrew McNamara, Director of Applied Machine Learning at Shopify, on the show to discuss a new topic, vibe entrepreneurship and the future of e-commerce. And Shopify has been killing it recently, and it was really fun to chat with Andrew about all the things they're cooking up over there. But first, we're kicking off the show today with something a little different. Instead of our standard news roundup, we're presenting a special report to dive deep into the topic at the forefront of our industry, the economics of software innovation and how AI is impacting it.
0:41And to help us do that, we're joined by a special guest and my dear friend, Fatima. She's developer advocate at GitLab. And Fatima is here to walk us through this brand new GitLab report. And we'll be breaking down some of the most compelling and potentially provocative even findings about what's inside. So Fatima, let's go ahead and dive right in. Welcome to the show. Yeah, thanks so much for having me, Andrew. It's always great to hang out with you. Amazing. Well, you know, without any further to do, let's talk a little bit about this report. So what's it called and what do we learn from it?
1:13Yeah, so this is a research report called the Economics of Software Innovation. And it was this global survey of C-level executives about AI, how much money they're spending on AI, how much adoption they're having with AI, and sort of thinking about, you know, how humans are learning with AI, the governance of it, and sort of strategic things across their organizations. It's a whopping like 40-page PDF. And so together, Andrew and I have pulled together a few stats that we thought would be interesting to talk about on the show. Yes. Well, great. That's great framing. And we're going to include links to this report so folks can go check it out.
1:46As you know, our Dev Interrupted listeners, we've been covering these kinds of stories for a while, looking at surveys from all across the industry. So I'm really excited to get GitLab's perspective here. So let's just dive into one of the first things that stood out. Fatima, you want to talk about it? Yeah, I thought this one was interesting. And so the report talks about how executives want to see a 50-50 human and AI partnership when building things. And currently, they've assessed it to be 75 % human and 25 % AI. But they're saying the, like, ideal balance is this 50-50. And, like, in my experience, I've seen the 75-25.
2:22I would say it's even less than 25. And I don't know if 50-50 is something to aspire towards. Like, I kind of disagree with this. I do as well, because also 50-50 in terms of work split feels very arbitrary, because a huge amount of that work could be toil. That could be freed up even more by the AI, right? But let's say that the AI does 75 even more percent of the work, and there's less for the humans to do. That doesn't mean that what the humans are doing is less valuable or less critical. And if you were to try to delegate some of that to AI, it could cause major issues. I can think of a lot of industries where aiming for a 50-50 split feels really arbitrary.
3:05So that's kind of an interesting finding in terms of the balance. Absolutely. Even like if you're thinking specifically about software as an industry and a lot of the use cases that we have for AI and LLMs right now with like, you know, turning spec into a starter project or debugging or researching, like I can't imagine that 50 percent of your role as like a senior software engineer can be done that way without some level of management of the AI. And so maybe this number is indicating like 50 % of your time is going to be managing a set of agents and the other 50 % of your time. And the report talks about how like human creativity, human vision, human collaboration, like can't ever go away.
3:48And so maybe that's the split, but I'm not totally sold on this stat just yet. Yeah. Well, I guess we're going to have to see what develops. You know, what else stood out from you in here? Another one that I thought, and it's funny because I'm pulling the things that I don't quite agree with. So there's a lot of other great stats in the report. So people should totally go and check those out. Some of those are highlighted on the website. So you don't necessarily have to download the report to see them. But I pulled out the ones that I thought we'd disagree with because I think that's where the fun is.
4:16And so 94 % of executives say that AI will pay for itself in two years is the other stat. Ooh, that's an interesting take. They think that so all of the money that is put into an AI investment will pay for itself in two years or less. Yeah. And if you check out the report, like the investment sort of varies across training, like bridging that training gap for skill sets, like hiring and things like that and like infrastructure. So it's not quite like individual people's salaries specifically, but it's also just like building out infrastructure for being able to host maybe their own custom models and things like that.
4:54I kind of disagree with this. I think if you look at it only from the infrastructure perspective, maybe it makes sense. Like you're getting some velocity in return for building things out long term. But I think from like a code perspective, and we talked about this a little bit before the show, like you have all this AI generated code. Who's going to maintain it in two years? Yeah, that's right. I mean, it also on a macro level is an interesting point that the AI pay for itself in under two years because at the rate that we're going, how does anyone know what their own infrastructure or architecture is going to even look like in two years?
5:29So to make that kind of future looking prediction is, I think, a little fuzzy for me. But the biggest part, too, is about really how I think AI is multiplying the way that we work is it actually increases the disposableness of a lot of the tools and software and architecture that we like cement into the ground and build so much stuff off of. AI reduces, in many ways, the tech debt and the initial lift of creating one-off tools and specialized, you know, fits for your own architecture. So gone are the days of having to have the behemoth that you specifically bespokely customize. And here are the days of creating those specific one-off and small, almost idiosyncratic engineering solutions, right?
6:15So if you think of leveraging AI in that way, it certainly could pay for itself if you're, you know, having that instead of paying for something else. But that is a limited privilege, I think, for a lot of companies to be able to work and build that way. And frankly, I don't think that we're there yet to know what that future will look like. Absolutely. And like if you're in client services, that's a really hard sell because every client thinks that their project is so unique and needs its own customized build that it's hard to sell to them that like, we're going to use this template that we built and we promise it's going to work for your needs because it's going to be maintainable in the long term.
6:50And like, isn't that where support contracts make money, right? Like we're going to do this thing and then we're going to support it for the next two to three to five years. And so I'm not really sure that the code itself will pay for itself. I think that they might, organizations might end up spending more money looking for people to maintain this. And that kind of reminds me, there was this article on Hacker News front page. I still like notoriously check the front page every few days. It was called AI first and the bus factor of zero. Like I wanted to talk about your listeners a little bit about the bus factor and like how that's changing and how that's going to impact the way that, you know, we continue to work.
7:33No, I love this. Why don't you give us the scoop on this article? I love this one. Cool. So the bus factor is this idea that like the risk of losing the knowledge about a project is the people that are on the bus. And please add to this a little bit if we need to give more details. So it's like, you know, if you and I built something together and like we were part of it and then you left the company for whatever reason, like the bus factor went from two to one. So like I'm now the person that can be asked in the future if there's technical doubt. Like even if I move on to another project and they hire a junior, they'll have to like pay like follow the documentation but then ask me questions and and so like now with ai generated code there's not necessarily an individual on the bus anymore so we're calling it the the author talks about how it's a bus factor of zero and so like now you don't know you know they're about the documentation about like there's nobody to go to and there's nobody who is responsible for making sure that whatever is left on the bus is enough for the next person to be able to like drive that and maintain it and make sure to keep it updated.
8:38And so that's kind of scary. Yeah, I think it's interesting to about how a lot of trends in software engineering sometimes are going to go backwards during periods of like fast innovation because you're so concerned with moving fast that you forget all of the fundamentals that made moving possible in the first place. So you kind of like outrun yourself and you fall on your face or it's like the Sisyphean experience of rolling that boulder up the hill of making those incremental security base test driven changes within your org, but then letting it all roll down because you want to chase the shiny new AI boulder, right?
9:14And the bus factor innovate all in the sake of innovation. And the bus aiming for the bus factor of zero is exactly that. Every software engineering leader, when asked before AI got on the scene, what were they aiming for with their bus factor? A high number. They wanted to go the other direction, not to zero. They wanted to go from three to five. They want to go from five to 10. They need more people to know about their code because that is how the code survives. Because remember, like we talked about a moment ago, this is a cemented layer of their architecture, of their technological world. They need people to know what's happening inside of it.
9:46So now in this world of more disposable software solutions, bespoke things, that bus factor can be zero because it could be entirely generated on the fly as almost like a shim, right? In a situation to fix something very particular. So aiming for the bus factor of zero runs counter to everything. But it makes a little bit of sense if you think that the software is entirely AI made and maintained. It depends on what its surface area is, but you really just need to know what that is doing. A bus with no one on it is scary, especially one that's moving on a road that you're also driving on with other people.
10:25That's the reality of having this in your code pipeline, right? Right. Interacting with other projects. Yeah. Yeah, exactly. So I think it really raises the importance of observability as well. Yeah. Like, you know, where is this bus headed? And if it gets lost on the way, like, how are you going to find this bus and make sure you're getting it back on track? And so, yeah, bus factor of zero is pretty scary to me. I understand, like you said, like it helps organizations move faster. But even as like models change, right? Like the models that you've relied on are now different or the LLM that you use to build that project is gone.
11:00like is even the zeroth bus factor, which is, I guess, in that case, the AI that you use to build it, like is that still consistent, right? Like the new model isn't going to give you the same answers that the first one did. And so that also scares me. It's like the meta version of this article. I should go and leave a comment on that Hackney's post. That's a very provocative thought to end the battle. I think about, you know, when the model itself then changes, your bus factor zero goes from zero to what? Like even less than... Is that negative? Is that negative technical debt? Negative imaginary number?
11:30Like it's something bad. So is someone who's good at math, please let us know. We need a mathematician on the show. You know, there was one other stand here. I just wanted to double click on before we move on to learn a little more about the GitLab release. And that's about how things like AI is impacting productivity. You know, were there things in the report that stood out to you on that topic? Because this is what we've been talking about from a lot of folks in the industry and how it's perceived. Most of the numbers in the report, and I can't remember the exact percentage, but they were like relatively positive that AI is improving productivity across these organizations that were surveyed.
12:07Okay, cool. You know, I think it'll be interesting to get a deeper dive into some of the findings behind that numbers. And our listeners, I know, have been following closely that understanding of how it impacts the developer productivity. So, folks, if you're listening, make sure that we include that in the newsletter so we can go do a deeper dive. And you said that you've looked at other reports. Like what sort of findings did you find about productivity? and where they're different. Yeah, so, you know, we've been covering this a bit from like surveys, like from Stack Overflow and from Lead Dev, really zooming in on the inside of an organization and understanding the actual impact of AI for engineers within like the day-to-day process and how executives are framing that conversation and the expectations they have around it.
12:48And what a lot of these surveys, especially a recent one from Lead Dev, for example, is finding is that there's a polarizing divide in the perception of developer productivity with AI. Folks who are very close to the AI and using it in a day-to-day process as an IC typically find that or report qualitatively less of those gains than their executive counterparts claim to perceive or think that they have. And so this creates this like polarizing situation within some orgs about the efficacy of AI, right? So that's what some of those reports have double clicked into. Yeah, and I think what you just mentioned there, like qualitative versus quantitative, like it's possible that the systems are reporting up the usage of the AI, but not necessarily what exactly it's being used on.
13:38And so I can imagine there's a reality where the IC is using the AI for scaffolding tasks or supportive tasks, but they're doing a lot of the strategic visioning of the project on their own or the work that the sprint that they're working on. And that maybe doesn't always bubble up to the executive level. But I'd be interesting to see the diff between the different reports and sort of what people at the highest 10 ,000th level are thinking of and what people like on the ground are experiencing. Yeah, I agree. I think we're going to keep learning more. So we'll keep exploring that one with you.
14:09More numbers. More numbers, please. And, you know, just before we start the wrap up and head into our guest for the day, I want you to tell us a little bit about the GitLab release that came out last week. Yeah. So we release every month. And so this month, it's 18.3. This release is sort of our vision for AI native software development. So more agent capabilities, some multi-model AI support. We're trying to be like integratable with all these third-party models and sort of bring them into the ecosystem as well. Some notable features, we on self-hosted, which is our sort of compliance and bring your own and set up your own environment.
14:46You can now bring your own models. So, you know, depending on what you're working on, like maybe you want Mistral to manage some code. Maybe you want Llama to help you write things. And so you can configure those models for your specific deployments. You can also do like hybrid. So maybe your coding standards are running off a cloud model and maybe you're like the stuff that is more proprietary. Maybe there's a formula or something that you're doing predictive modeling on. You can host that one locally and sort of fine tune it for your needs. So I think that really brings a lot of flexibility on self-hosted.
15:16That's pretty cool. And there was another thing that stood out to me, too, I want to ask you about it. I see there's a CLI agent that you can create on the fly and interact with your favorite tool. Yes. It's pretty cool. This one's very sci-fi. As someone who I have a very positive vision for the future, which, you know, when you really think deep into it, you have to kind of tweak a little bit. But basically, on merge requests, you can tag in CLI agents. So integrated with Cloud Code, OpenAI Codex, Amazon Q, and ask them to do things for you. So as long as you bring in, this is another bring your own API key.
15:46I feel like this release is bring your own. There's like a bring your own episode. It's a bring your own party. Bring your own LLM, bring your own API key. I brought my own co-host today. I love it. It's bring your own. So basically, it could be just like, cloud code, can you fix this? Or can you open a merge request that addresses this bug? And it will go ahead and do that for you. So it's sort of having a partner in the CLI, right? Built into the platform. Amazing. Well, Fatima, thanks so much for coming on the pod. to give us the scoop on GitLab and the report. We're going to include details for all of this in the newsletter.
16:20For those listening, stay tuned because after the break, you'll hear from Shopify's Andrew McNamara. Thanks so much for having me. This has been really fun.
16:30Are you investing in AI but struggling to see the real impact on your engineering team's productivity? Well, you're not alone. In a free 35-minute workshop that I'll be hosting with Linear B, we're going to show you how to translate AI metrics into business ROI, just like Expedia and Adobe have. And you'll learn a simple framework for understanding where AI is helping, where it's hurting, and where to focus your next investment. And besides, you're going to get a nice takeaway report on AI productivity as well. So don't miss out. The workshop's coming up on September 17th or 18th. Grab your slot and we'll see you there.
17:06We're back on Dev Interrupted and joining me is Andrew McNamara, the Director of Applied Machine Learning at Shopify. And his impressive background, it includes so many great things like applied research at Microsoft after Maluba, where he built and scaled machine learning algorithms was acquired in 2017. And that really sets the date for you because he's been building human centered AI since before it was cool. And we're actually going to get to that a little later. But until recently, it was more just called machine learning. And right now, Andrew is bringing Shopify Sidekick to e-commerce with the goal of unlocking the full power of the platform in everyone's hands using only natural language.
17:47And with Sidekick, we're not just talking about automating tasks. We're watching the rise of something new, a generation of merchants that can almost run a vibes first business and no spreadsheets, no MBAs, just good ideas, great products and the right AI tools. And I love this idea because it's so quintessentially 2025. So I'm excited to dive into this with you. Andrew, welcome to the show. Yeah, thanks so much. I'm excited to be here and really looking forward to our chat. Great. So starting off, you know, I wanted to pick your brain about this like personal assistant to AI pipeline that's been your career.
18:23And we talked about this a little bit when we first met. And I wanted to kind of explore that here with you today. So could you maybe tell me about your time, like building assistance for the last 16 years at Maluba and Microsoft and beyond? Yeah, I think just having gone from that scrappy startup back in 2010, even starting the personal assistant before Siri came out, which was crazy. So when Siri did come out, we were thought we were in a lot of trouble. But, you know, being pretty scrappy, we ended up getting some pretty big licensing deals with Samsung, Microsoft, or not Microsoft, Samsung, LG, their phones and TVs, and even BlackBerry at the time.
19:04And then, you know, through that, we kind of started up a research lab and then eventually got acquired, like you said, and we became, you know, Microsoft Research. and then we got back into, you know, so we were doing research for a bit in natural language, then got back into the product side of things with the chat with, you know, Sydney now called Copilot. Back then it was called Sydney and Bing Chat. But yeah, the mix of research and engineering has just been like super helpful from that whole scrappy startup to big company and then bringing both kind of experiences here to Shopify. And it's really interesting how your background spans this applied research world.
19:41You know, it's not every day that you really talk with somebody who comes from applied research. And often when I do, they fall onto one side of like, they're really strongly in the research camp or they're really strongly in the like applied camp, the building. What about you as an applied researcher? We've had many of them on Dev Interrupted. I'm kind of curious, like what, how does that you approach your work philosophy? Yeah, I think one of the big things from being on both the, you know, the very research side in Microsoft Research and then, you know, the scrappy engineering and applied research side in the startup at Maloobo.
20:10but was like just the value of evaluations and how that's really shaped kind of everything that I've done moving forward. Evaluations are big in the research community. They're also big on the product side, but they're hard to get right in both cases. And I think with LM these days and vibe coding, you know, and whatnot, proper evals seems to be kind of falling off a lot of people's radars, honestly. So I think it's just like a huge value that sometimes people are missing these days. I'm really glad you're touching on evals because this is a topic that I've been learning more about recently, more in depth.
20:48And it's something that I know many folks building in the space are really caring about as they start to build these products, you know, production-ready applications, understanding the decisions that they make to quote-unquote improve it. You know, does it actually improve it? Does it make it better? And what about it did improve and why? And, you know, Andrew, you recently gave a talk, actually, at the International Conference on machine learning about building production-ready agentic systems. And it touched on this need for like a robust eval system for tools. And so I want to know from you, you know, what is vibe testing compared to what you are talking about?
21:22And how can folks like level up to reach those real evals? Yeah, it's a great point. And yeah, that talk at ICML actually gave, there's a lot of great discussions afterwards, both in the talk of people sticking around and then coming by the Shopify booth after and just having lots of deep discussions on it. So I think it's, it is a huge topic these days and, and it's super important. It's a big part of machine learning and LLMs have really changed a lot about machine learning specifically around, you know, validation testing and evals. And in my opinion, like LMs have almost polarized evals. Like everyone used to have a standard way of doing evaluations.
21:59You know, you'd split up your training data into, or you split up your data into training and validation and then you train and then you test and then you'd have this like holdout or golden set. that would be hidden developers. And then you would test that on after the model was done training and see how you're doing. And you would kind of optimize for that. But these days, LMs have completely changed evals. You can make insanely powerful evals with LLM as a judge or even agents as a judge, which was a paper that I saw at ICML. But you can also get away with just vibe testing and just asking an agent, hey, can you rate this from one to 10?
22:32Or the LMs are so good that you just try a couple of things and it works. And so you kind of ship it. So we've gone from like this very principled approach in classic ML to LM enabling super powerful evals. But then LM has also worked so good that some people kind of just vibe tests and ship. So yeah, it's an interesting spot that we're in right now. Very polarized. Yeah, very polarized. And you're kind of calling out some of the, I think the pitfall here of, you know, you can use, you can leverage AI so much to get so much of that done. That along the way, you kind of lose the rigidity of like the benchmark.
23:07and what it's looking for. It's like, sure, you're getting that result faster, but what is like the efficacy and the accuracy of that result? That starts to get thrown into question, right? And so this actually brings me to an interesting question because you're working on a product that's, you know, it's bringing AI, it's bringing agentic work to really close to a huge customer base, to a huge user base, right? So what's like the hardest parts of getting a system like that to be production ready? Is it the evals? Is it something else? Yeah, I think the evals are probably the most important thing to get a production ready and probably the hardest because it's pretty easy actually to get an agent up and running these days or any kind of product with LLMs.
23:50Like, for example, what we built in the first two years at Maluba, I could literally do in an afternoon, like a day at the most I could rebuild Maluba, which is like insane on how far we've come in the last 15, 16 years. But for it to be in production, you have to have very high trust that what you change is making it better across the board. And you really need evals to do that. And it's really, it's especially difficult in a conversational setting as well. But I think it's, you know, it's a big part of the talk at ICML conference on how to, you know, really make your systems production ready by having very strong evals.
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24:29And, you know, I'll make sure we include a link to that talk if we can share it to our audience that we folks can go check it out. Just because I know people are going to want to try to learn from this to replicate for their own tools that they're building. A lot of folks who listen to Dev Interrupted they're building, they're experimenting in this space. And, you know, many of us are experimenting internally in terms of improving our own workflows, seeing how it impacts things like software delivery. But there are many of us who are also building and shipping AI products. And I know that understanding the impact of the changes that you make, especially when we're talking about natural language prompt changes and calibration over time.
25:07This eval system is such a critical component. So I know everyone is just like really hungry to learn more. And moving on from that, like, like problem space of like understanding the impact of the tool. Let's move into a little bit about the tool itself and talk about your work building Sidekick. And I want to start at the top. You know, for some folks listening to this, this is probably their first time hearing about Sidekick. What's the vision behind it? Yeah, Sidekick's vision is that it's basically your AI co-founder or your e-commerce expert that doesn't judge you. You can feel comfortable to ask any question and get expert results.
25:42I think like around why it started and how it started that kind of led to this vision was I've heard Toby it was kind of before my time at Shopify but I've heard Toby talk about this before which was there was and I'm not going to get the numbers exactly correct here but there's basically studies or user questionnaires when people are signing up on whether they you know have an e-commerce or an entrepreneur expert in their life that they can ask questions to or not. when they're starting a store. And then when they do start the store, if we check back on that set of users that answered this question or a part of this study, how successful is their store right now?
26:21Are they still running the store? Did they get their first sale, etc. And it was like very telling results. Again, the numbers aren't exact here, but it was something like maybe 80 % of people that had an entrepreneur expert in their life or an e-commerce expert that they could reach out to still had stores running and successful stores going. And I think like almost, almost everyone who didn't have that in their life, like never finished completing their store. They never made their first sale or their store has since been shut down. Again, so I don't have the exact numbers, but it was a pretty telling story that having somebody who you could reach out to, answer any question that you want, ask anything, feel free, like you can ask anything.
27:05It was just like so critical to people starting a business. And that's what Sidekick is. That's the vision behind it. That's what we want to provide with Sidekick. Wow. So that's like an incredible signal. Looking at those who get the help of an entrepreneur or a resource in their life that's familiar with business working, how much more successful they are, the discrepancy between them and those who can't. And so that sets the scene perfectly for Sidekick being this AI assistant within your selling platform that is an expert on not only the platform itself, but specifically your business. And it becomes, like you said, that kind of co-founder.
27:43So, you know, we're talking about Shopify here. Shopify has a huge user base and a huge spectrum of users, right? From anyone selling like homemade candles to, you know, in some cases, multi-million dollar direct-to-consumer brands. So how do you design a tool like Sidekick to work for both of those groups? Yeah, Sidekick has, it is an interesting problem to solve. Well, and Sidekick does have a massive range of skills, ranging from helping you design your logo, generating your theme basically from scratch, which is something that we just launched a couple months ago and is like new merchants are getting huge, huge value out of that.
28:18All the way to like complex analytics, which can run on or get data about any single piece of data that's related to your business. So we find users are like ramping up their stores way quicker and getting to their first sale much faster. and then we also find that big merchants are talking about how they're getting these very deep and actionable insights about their store that was virtually impossible to get before because there's the preset graphs, you can run custom queries but just having this agentic loop in reasoning and planning able to have access to these low-level tools that can run queries for you and get these insights has just been huge.
28:58So we're seeing incredible adoption from both new users getting to first sale quicker and massive companies and businesses getting like super deep and actionable insights on their store. Yeah, it's really interesting because like for a small business, it becomes their concierge. Like, I don't know how to change this thing in my store. You go do it for me. You're the expert on the platform. And then like for the big company, you know, they're like, they get a free data scientist out of the box. You know, tell me about this kind of user or this kind of customer. Like help me understand this slice of my already pre-existing user base or a customer base, which is pretty cool.
29:32And, you know, there's a lot of challenges, I think, too, in building something so close to like an e-commerce workflow. You're talking about like monetary transactions, building a business and a livelihood and people's lives are invested in this. And, you know, how do you bring engineers close to that problem at Shopify? How's that part of like your engineering culture? That's a good question, too. I think like one of the biggest challenges we have is how do we know that we're providing the right value to merchants? And then like you say, how do we make sure that the engineers on our team are working on the right thing to bring that value.
30:05And, you know, not to sound like a broken record, but I think there's two things here. Like one is definitely evals because like you go and watch that ICML talk on evals. One important thing is a ground truth set, which is what we're calibrating our judge to. You can think of it, you know, I won't get super damaged now, but you can think of it as like basically your specs. And then so we're trying to get the LM judge to pretty much look at a conversation and say, does this match our specs perfectly or not? And did a good conversation happen? And when we created the LLM judge, a very important part of it that not a lot of people realize, especially, you know, at iSmell, I was talking to people and they kind of had a different view on this, but I think it's critical that your LLM judge or your evaluation does not actually know what features you support.
30:51So yes, it'll look at your specs and judge conversations based on that, but it also, it itself doesn't know what you support and what you don't. Because we want to look at, did we fulfill the user's goals? Was the merchant happy? And if we just, if Sidekick says, we don't support that, and we can't grade that as basically a high mark. So conversations that people are having that where we don't do what they want, we're marking that as low. And then as we add more and more features, suddenly these scenarios that were marked as low by our evaluations are suddenly be marked as higher. So then we're seeing the score go up and we're moving the score up in a positive direction with every single change we do.
31:35So we know that we're adding more and more value to merchants and supporting the right things. That's really cool. It's almost like you're pinning user stories right there when they come in through the experience and the eval flags is like it's failed. Wasn't because of whatever, it's because it's not on the platform. There's not tools for it. And then as the engineers build and fill out those problems. And you have a catalog of things you need to build, right? These are user stories that people want to do. And then you build them and then you get out of the box free evaluation of that user story is now in flight and you can see the eval of it because you identified it that way in the first place.
32:09Yeah. Yeah, and we try to build like lowest level tools possible, like natural language to, you know, query language that can access your data, natural language to something else that can access your store. And then people end up using it in, you know, creative ways that we didn't predefine. But just because we gave low-level access to tools, they're doing cool things. Yeah, you're giving them the primitives of the Shopify system to be able to manipulate. And so let's talk about that. What are some surprising use cases you're seeing people get out of it right now when they turn on Sidekick? Yeah, I think just the deep research and getting actual insights out of it.
32:45And one of the things we see happening on Twitter and social media is that people are sharing these huge, massive prompts. with each other and like getting it to do deep research, like very long prompts. Like it's insane. Like you think it's a chat system while they're just talking to it, but they're writing massive, massive prompts and then they're sharing it with each other. And it's even evolved to somebody made a repository so that they have all these sidekick prompts in it. And then they're sharing this repository with people so that people can go in and copy paste and put in sidekick. So then like from our end, you know, being merchant obsessed and building in the open, And we just launched a feature where you can share a prompt and it just gives you a short link.
33:24And then you can click that short link and it'll open your store, pre-fill it. And then you can look at the prompt, personalize it for your store, and then just easily run it. So it's this back and forth, like we're learning how people are doing it. We're learning what merchants are doing, what their journey is like. And then we're reacting to that and building for them. And so it's just this great relationship with merchants, you know, to kind of build what they need and keep. you know, keep facilitating them and helping them on their journey. Yeah, it speaks to the high value of what they get out of the system.
33:54And it's funny, so out there you're saying there's like an awesome sidekick, you know, whatever repo that has all of the prompts. It's really cool when you see that not only the emergent use cases, but then the emergent prompt engineering, context engineering community around it. You know, so much you can learn from that kind of customer base. It's been very cool to see, yeah. Yeah. And so, you know, we can't talk about all of this in your time at Shopify without touching a little bit about what it means to be, you know, all in on AI at Shopify. This is something we hear from the top at Shopify and it's been in the news many times.
34:27And I wanted to ask you, just like as someone who works at an applied position, applied research right on top of this problem set, what does being all in on AI look like for you at Shopify? Yeah, I think just, you know, the best way and what it looks like to me, and even if I just look at Shopify as a whole, like people, it's about how they how reflex reflexively they reach for ai like is ai anytime you have a task you gotta make a tweet maybe you're using ai you gotta write an email you're probably using ai to at least like read it over and slightly change it or there's tons of mcp tools out there that you can use to your whatever lm you choose to use which like all of them are available at shopify and then you can plug in different tools to it and just like almost everything you do you reach for like AI first.
35:13And that's, that's how I operate during the day. And, and a lot of people at Shopify, you know, not just tech people, but, you know, everyone is, is being very reflexively reaching for AI. And I think that's, that's the biggest indicator of, of how all in, you know, we are on AI. And I think, you know, even at what we call summit, which is where the whole company got together for a week long conference, there was like, you know, Shopify AI learning village, you know there was talks throughout the whole week on how people are using ai how they can help each other how teach other people how to using it it's it's a great culture here at shopify with like using ai and and trying to make it more effect make you more effective and more efficient that's really great i i love hearing about people's experimental cultures within uh their engineering orgs or just their orgs at large about experimenting and trying new stuff out especially like the of sharing great stuff.
36:07We've talked with a lot of guests recently who've really shared about that internal AI thought group that's presenting every week about those cool use cases that they find. And there's so much value there in having those conversations that can get applied to even things that you're building, like right now with Sidekick, which is really cool to be able to double down on all of that. And this whole conversation has just made me think, gosh, I want to open a Shopify store and just put a robot in charge of it. It's like it's inspired. It's inspired. It's kicked off a lot of ideas, but also it's like the way that it mixes matches its tools is so interesting and almost kind of bridges into what you could call like vibe entrepreneurship.
36:44And it's a funny phrase to reflect on, especially in a world where like vibe coding is already so polarizing. But I think that there's a lot actually to talk about there. And I think it's interesting to think about how these tools can interact with like the future. So how can AI tools like Sidekick enable a new generation of entrepreneurs? Like you talked about that survey group, right? The ones that did and didn't have access. You know, how is Sidekick going to change things for them? Yeah, I think it's just so much easier to become a merchant and to start a business these days. And like to get to your first sale, like the measuring of like how quick can people get to their first sale?
37:25I think like Sidekick is making a massive impact on that. So, you know, with Horizon theme, which is a theme we launched a couple months ago, and how easy it is to use Sidekick to just create a customized store for you through just, you know, vibe entrepreneurship or vibe, you know, creating your store, you know, even helping you make a logo or even helping you decide what products to sell and how to start your business or what your business should even be. Like all these things are now on the table for vibe entrepreneurship. And like you said, it's super popular for vibe coding. But yeah, I think vibe entrepreneurship and, you know, is is something that is is coming, especially with, you know, tools like Sidekick.
38:06Yeah. And so where do you think like this this trend could kind of go? Like you built something like Sidekick. What eventuality do you think that that would take us to on something like Shopify? Do you have any ideas? again it's one of those things where like there's going to be emergent use cases where you where you you don't even know like it could be a possibility that yeah you know that's helping you start your business run your business uh and do everything i don't think it'll ever get to like a completely autonomous thing i think the humans are like humans are so important to this it kind of makes me think like at the icmail talk there was like you know we're doing reinforcement learning for training and it basically reward hacked that and optimized on something we didn't want but it was hard to like see that and I think like the same thing could happen if you go like completely vibe entrepreneurship you never know like what it'll consider high rewards that may not be best in line with your business so I think it's like it's definitely a balancing act between you know having that human entrepreneur mindset that creativity that judgment is so critical but But then having AI like Sidekick is just like helping you jumpstart your business and really, you know, move closer to running it as autonomous.
39:20You know, I don't I don't think getting autonomous business will be super easy. But, you know, helping you get started and figuring out what to do and then making judgment calls on it, I think is just like an incredible opportunity that we're in right now. Yeah, I especially think too, for the interesting thing about something like an autonomous business, even if that's outside the realm of what something like Sidekick is, is, you know, then you're talking about plugging AI into creating like value, like societal value or monetary value. And a lot of times when on Dev Interrupted, we focus really specifically on plugging AI in to get that engineering value to ship that better product, faster, safer, more secure and more impactful for customers.
40:02Right. but it's just a big eye opener that like, you know, we're solving these problems here in the engineering world. AI can solve a lot of problems in a lot of realms, including things like businesses and, you know, generating capital or whatever they may be. But I agree with you that humans will always be vital in that loop. And, you know, there are things that get optimized for that we always have to keep our eyes open for. So it really sets the scene for an interesting future. But Sidekick, his name is Sidekick for a reason. It's going to say, I think your co-founder, or your assistant, your technical purveyor for the time being.
40:36But, you know, Andrew, this has been like a super fun conversation to talk about how you're approaching building like business assistance, especially since your background in applied research spans, you know, talking about and building these tools before they were really more household games and people cared about them. So we really got to see that perspective of how you've of what matters to you still all these years later, what matters now more than ever. And so I think the bottom line of this talk is evals, evals, evals for what people should care about. So we're going to drop resources for that.
41:07But I also now want to go back to the drawing board and come back up with a Shopify store idea with Sidekick. I got to see what this thing can do. But before we wrap up, you know, where can our audience go to learn more about what you're working on and what you do, Andrew? I mean, I'm pretty active on Twitter and I love building out in the open. And I love, you know, I think probably every tweet that's mentioned like Shopify and Sidekick. in it together in the last eight months, I've basically read and either interacted with in some way. So, you know, I love talking to merchants. I love seeing what they're building, what they're doing with Sidekick.
41:39And I love building in the open. So yeah, if you, you know, maybe share my Twitter link or something and people can follow along and see our updates and what we're doing, what we're thinking about. Yeah, no, we'll definitely share them with our listeners. And, you know, to you, our listeners, thanks for joining us for this conversation. It's been a really interesting one for sure. So be sure to go follow and join this conversation online. You know, we're having it right now in your ear, but we're going to continue talking about it on LinkedIn. You can check out Andrew's talk as well that he recently gave ICML.
42:09That's kind of the grounded for a lot of the stuff we covered today. But more importantly, go check out Sidekick and, you know, see what it can do. I know I'm going to go explore it after this. And if I kick off a store, Andrew, and have my little robot co-founder try to sell something with me, I might loop you back in to give me some tips or otherwise point me in that right direction. So I appreciate you teaching us about it. Let me know what you think. It'll be cool. So, you know, thanks for listening to Dev Interrupted and we'll see you next time.
From the publisher
First, there was vibe coding. Now, get ready for "vibe entrepreneurship."
Andrew McNamara, Director of Applied Machine Learning at Shopify, joins us to explain how his team is making this new era of business a reality. He shares the vision behind Shopify Sidekick, an AI co-founder designed to empower merchants by acting as their on-demand e-commerce expert. Drawing on his 16-year journey building AI assistants, Andrew reveals what it truly takes to create an AI tool that customers can trust with their livelihood.
He shares a critical insight from his applied research background: the hardest and most important part of building production-ready AI isn't the model, but the evaluation ("eval") system. Andrew breaks down Shopify's innovative approach of using an LLM-as-a-judge to measure how well they're fulfilling user goals, not just executing features. This conversation is a definitive guide to creating high-trust AI systems and offers a powerful glimpse into the future of commerce.
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Referenced in today's show:
- The Economics of Software Innovation
- “AI First” and the Bus Factor of 0
- GitLab 18.3 released with Duo Agent Platform in Visual Studio (Beta) and Embedded views
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