Most entrepreneurs will face the same haunting question: When is it time to call it? For Mike Krieger, Instagram co-founder and current CPO at Anthropic, the answer came after methodically testing his final three ideas for Artifact, his AI news startup that never found product-market fit despite sophisticated personalization technology.
From co-founding Instagram and selling it to Facebook for $1 billion, to shutting down Artifact and joining one of AI's most promising companies, Krieger has navigated the full spectrum of startup outcomes. His journey offers a rare perspective on building products at the intersection of emerging technology and human behavior—from mobile photography in 2010 to large language models in 2024.
In this candid conversation, Krieger shares the framework that helped him recognize when to pivot Instagram from a location app called Bourbon, the hard lessons from Artifact's failure, and why building AI products requires solving problems today, not just showcasing intelligence. This is product thinking at its finest—practical wisdom from someone who's built for both the early mobile era and the AI revolution.
Watch the full interview now on EO's YouTube channel! Below is the complete transcription of the interview. Minor edits have been made for clarity and readability.
Key Highlights:
"When is it time to call it? When does the chapter close? I think one big piece of advice is I think we're often as entrepreneurs, we have a lot of weight on our shoulders and between Instagram and artifact, I did some angel investment and it's never positive news when an entrepreneur tells you that a company doesn't work, but I've seen it before, you know, and so it's not a surprise that some companies don't work out. That's baked into the model. And so I guess the advice I would give is really check in with your investors and don't, I've seen entrepreneurs get stuck in this idea of like, I have to keep going because my investor expects me to. And I think what they'll find is sometimes investors are like, you're trying, you've tried it all in this space. I think it's time to call it and that's OK. And you know, it's not, it's never a celebration, but it doesn't have to be, you know, a tragedy either."
From Brazilian Kid to Stanford's Secret Program
Can you tell us about your journey and what led you to where you are today?
Mike Krieger: I'm Mike Krieger. I'm currently the chief product officer at Anthropic, which is an AI company based here in San Francisco. I co-founded Instagram and was its chief technology officer from about 2010 to 2018, so a nice crazy journey that we had there too. Started one other company with the same founder as Instagram called Artifact, which was an AI news startup, and then joined Anthropic just under a year ago. So it's been the kind of third chapter in my professional career and it's been a lot of fun so far.
Credit my dad for a lot of this. He brought home a computer for us when I was about 4. I remember I had around Microsoft DOS still didn't have Windows. But one of the things that was very cool is you can just type edit and you would be able to open up the files and all the, even the apps that came with the computer. And so I think I liked taking things apart and putting them back together. And I think I really liked seeing how things worked. So it sparked very early for me when I was just 4.
When it came time to decide what my career was going to be what was interesting was in Brazil at the time, there wasn't really the same kind of technology industry as there is today. And so I didn't have any friends or parents, friends who were working in tech. And so I didn't really see it as a career for me. I just thought it was a thing other people did. And so it actually only really took me until I came to California that I realized that this childhood interest that I had actually was something that I could do as a career and make a whole living off of.

What was your experience like at Stanford and how did it shape your approach to product development?
Mike Krieger: When I got to Stanford, I discovered that they had this degree program called Symbolic Systems, which only Stanford has, and it's kind of this little strange program that when I was there, I think per year they had about 40 or 50 students, and now I think it's more than 200, so it's really grown, which is great. What I loved about it is that it wasn't just computer science, which I was interested in, but it also included design, included philosophy, included psychology. And it was really, you think about the idea of the program, it's not just to study computing, it's to study the whole context around why we build software.
That was really powerful for me because I knew I liked design and I liked making things useful for people, but I also liked the actual building of those things. So I think a few of the things I really came out of that program with one was this idea that everything you build should solve a problem for somebody, right? It's like, kind of the core of design thinking that you identify problems, you figure out how you can best solve them after doing the research, and then you validate what you've built to make sure you actually solve those problems. I think that is really important and that's a big piece of what I came out with.
The other is the value of prototyping. So, you know, instead of just working for six months on a project and then showing it to somebody for the first time, and then it turns out you got something really fundamentally wrong, willing to build prototypes, show them along the way and open up the design process a lot more. And maybe the last one is the value of a good team, and having the right partners. So the person I co-founded Instagram with is somebody I actually met back at Stanford.
The Birth of Instagram: From Bourbon to Billion-Dollar Exit
What was the mobile landscape like in 2009 and how did Instagram come about?
Mike Krieger: You have to kind of rewind your time machine back to 2009. Now we take for granted that everybody uses a lot of apps on their phone, that we take a lot of photos on our phone, and that we network or we use social media on our phones, but in 2009, that wasn't the case quite yet. So the cameras were getting better, but they were still quite bad. Facebook had a mobile app, but it was kind of that early one where it was kind of just trying to recreate the website on the mobile side and it wasn't quite as native, and there were very few sort of new social products coming out.
And the context is important because the reason I got really excited to collaborate with Kevin, who ended up being my co-founder, is that he wanted to change all three of those things. So he was building at the time was a location sharing site, a little bit like Foursquare, if you remember Foursquare, but with photos and videos attached as well and really creating a social experience when you're out and about. That was really exciting to me because I saw the potential for mobile device to create a much more personal connecting experience.

What were the key moments that led to Instagram's creation?
Mike Krieger: So first moment was reconnecting with Kevin and seeing that he was interested in these ideas. Second important moment was me getting my work visa so I could go work with him. So I first had to transfer my work visa and that actually took 4 months. And then the third important moment was us realizing that product that we were working on was called Bourbon, B U R B N, which was that sort of location based check-in, location sharing app. It was good, but it was not a product that was really going to take us to where we wanted to go.
And so we had a moment where we had to take a pause, really peel back all of what was not working about the product and realize that at the core, the piece that was really working was this aspect about taking photos, sharing what you were doing, and connecting with people that way. And that was really the moment where we took a lot of distracting things, stripped them all away, and then focus on what would eventually become Instagram.
How do you identify when emerging technologies are ready for broader adoption?
Mike Krieger: I think a lot of the art, and it's a part both art and science of building great products, especially with emerging technologies. So Instagram, it was the rise of the mobile phone, finding the technologies that are ready for broader adoption than they currently have, and then finding how do you build the product around it to make it usable for many, many people. That's a common sort of through line and I think the kinds of things you can look for in terms of that early energy are, are there some people already starting to do something interesting in the space, but it's all the early adopters. That's an interesting kind of area.
The other thing I look at often is the rate of change. So, if you look at the iPhone 3 to the 3GS to the 4, and you look at the quality of the photos and the quality of the networking stack and the ability to connect, you can see the jumps. So you're like, OK, if it goes 1 or 2 more jumps, it's going to be incredible. With LLMs, I joined Anthropic. We had just come out with Cloud 3, and Cloud 3 was our first model that really started to get more usage. It was still limited in a lot of ways. But then you see the next, we did cloud 3.5, and that was a big leap. So you can imagine that we're going to continue to get these large jumps. And so as a product builder, you have to start thinking, I want to build a product that's useful today, but is also ready to catch the wave of what the next big leap is.
Inside the Facebook Acquisition: Preserving Startup DNA at Scale
What was it like joining Facebook and how did that experience shape your understanding of scaling teams?
Mike Krieger: I like to say that at Instagram, you know, before the acquisition, we didn't yet have a company. And what I mean by that was we were 13 people, had some ideas around revenue, but we hadn't built any of them out yet. Still very much that like early startup. Joining Facebook was really interesting to me because they were at the time, thousands of people, they had just crossed a billion users, so much bigger than us in terms of company size, but they were really focused on preserving as much of the startup culture as they could.
So for example, every 3 or 4 months, they would do a whole company hackathon where everybody would get to focus on what they were interested in for a couple of days instead of the ordinary roadmap. They really prized experimentation. They really tried to, you know, famously had the move fast and break things kind of slogan. So, I think it was good that we went to a company that was bigger, but not super big company or slow, and it taught us that you can grow your team and grow your ambition, but still focus on the things that keep you moving fast.

What did you learn about building the right team culture?
Mike Krieger: I think the value of the team is something that will stay with me forever because, you know, you can have the right strategy, and you can have a good product. Ultimately, the details that go into those products, the pace and speed that you're able to execute on and like how much fun it is, which is also really important, ultimately comes down to having the right team around you. And that's a mixture of people that are talented, but don't have a lot of ego, which is an interesting and difficult combination to find sometimes, people that are willing to be generalists rather than just be caught in their sort of individual silo.
And so, you know, on Instagram, we had people who would start off writing the back end for a feature, but would also then build the iOS or the Android part and it's important, I think for you to have that fluidity, especially on engineering or designers that would code or product managers that would design and it's just not getting everybody boxed in. So that aspect is really important. And also a team that really cares about the product they're building, which again, is easily more easily said than done. It's I've seen companies where everybody is working and they could be working hard, but they don't have a passion or really an attachment to the thing that they're working on. You're never going to get great products that way.
Artifact's Rise and Fall: When Personalization Isn't Enough
Tell us about Artifact and what you were trying to build.
Mike Krieger: In 2021, I founded Artifact with the same co-founder Kevin. Our goal, our observation was there's been a rise, and at the time it wasn't LLMs yet, but there was a lot of rise in machine learning and the beginning of some of these neural networks for all of that interest and rise. There were still not a lot of products being built that felt very personal, because if you think about it, the promise of some of this machine learning was great, with a lot of signals, we'll be able to incorporate what's personal to you and also what's aggregated out among a broader group and be able to tailor the experience.
But you looked around and there actually wasn't that many personal experiences. So our bet with the company was by combining cutting edge machine learning and good product design, we'd be able to build products that felt very personal to you. And we started with news, and articles in general, because that was something that we felt most people are readers, even if they're not like book readers, they like reading articles online. And there's an existing kind of ecosystem of blogs and newsletters and news sites that was out there that we, if we could just connect people to those sites, be able to deliver a good product.

What went wrong with Artifact and when did you realize it wasn't working?
Mike Krieger: We launched the product after about 2 years in private beta, which I think was too long because it took us too long to get out to the market to start learning. And it also meant that by the time we launched, the team was already quite exhausted for having worked really, really hard on this product for 2 years nonstop. And then we let the product run for about 1 year. And after 1 year, what we noticed was the energy was not there in the system. Like we would work really hard to improve a feature or add social features and comments and reshares or posts and user generated content, like we were trying big ideas, like it wasn't like the product was standing still, and it was very hard to shift the energy in the system.
And I think that was because there was not a fundamental fit around what we were doing and what people were wanting. And I think there was probably two aspects of that. The first one was, even if our algorithms, I think were very good, the mobile web kind of websites that we were sending people to for this news, they were often like full of ads or not formatted very well or full of like pop-up videos. It's just not a very good experience once you actually click through, and that was like, I think a hard experience to deliver. And I think the second part was our product got really good if you put enough data in there and you read enough articles, we'd get very personal to you at the level of, all right, Mike is interested in Formula One, but not just Formula One, he's interested specifically in this driver and also he likes Brazilian modernist architecture, but also when that's paired with Scandinavian design, like that level of really specific knowledge. But to get that, you have to read a lot of articles. And so most people would come in, they would read a couple of articles, they would say, this isn't very different than Apple News, and then they would bounce off.
What were the key lessons you took from the Artifact experience?
Mike Krieger: So I think we bet too hard on personalization without remembering that you also have to be good at the very beginning before you've really gotten a lot of personal content. I think one big lesson is that users are not going to adopt a feature or a product just because of the technology underneath or just because it has intelligence, it actually has to still solve the problem. It goes all the way back to what I had learned at Stanford. So as we build products at Anthropic, of course, the models are very intelligent and they can do a lot, but you have to do more than just say, this model is so smart, you have to go beyond that and say, and here's what it can do for you, and here's how it can connect to you, and here's how it can be useful to you, even if you're just getting started with it, right?
It goes back to that feeling an artifact of, yeah, the product is good if you put a lot of work into it. Like we need to design things with cloud that are useful for somebody that's just discovering LLMs kind of for the first time. So a lot of the work that we're doing right now is how do we lower the barrier for people who aren't yet familiar with all the ways that AI can help you in your daily life, to just give them some really concrete things that they could do, where it's useful to them today rather than in theory. So that's a big lesson, lesson learned.
The Art of Knowing When to Call It
How did you decide it was time to shut down Artifact and what advice do you have for entrepreneurs facing this decision?
Mike Krieger: That's a great question around, like, when is it time to call it? When does the chapter close? The way that we did this with artifact, and I think this helped was we sat down, me and Kevin, we made a list of like, what are the ideas that we still have in this space that we will feel really silly not having tried before shutting it down. And we wrote them down and then we prioritized like three big ones that we said, we want to try this. And after we try this, we'll take a step back and say, did it change? Did it change the trajectory of the company? And we did that. And then we kind of wrapped up 2023 and entered 2024 and we said, we tried them. It's still not changing the trajectory, then it's time to move on.
But it is quite tricky. I think it's, I've seen entrepreneurs get stuck at companies for years that they feel they owe it to themselves or their investors to keep going, but it's not likely to shift the directions. I think being concrete either with a date or with a set of projects helps you know when to move on. I think one big piece of advice is I think we're often as entrepreneurs, we have a lot of weight on our shoulders and between Instagram and artifact, I did some angel investment and it's never positive news when an entrepreneur tells you that a company doesn't work, but I've seen it before, and so it's not a surprise that some companies don't work out. That's baked into the model. And so I guess the advice I'll give is really check in with your investors and don't, I've seen entrepreneurs get stuck in this idea of like, I have to keep going because my investor expects me to. And I think what they'll find is sometimes investors are like, you're trying, you've tried it all in this space. I think it's time to call it and that's OK.
Building AI Products at Anthropic: The Dynamic Challenge
What attracted you to Anthropic and how is building AI products different from your previous experiences?
Mike Krieger: I think what was interesting with the anthropic role is that it was both joining an existing company. The company was about 3 years old at the time, had already launched models, had claude.ai, but there was still a lot of 0 to 1 to be done. So I don't think we had our mobile apps yet. We hadn't built things like claude code, which is our agentic coding tool. So there was a lot of empty space still in the product. So it was kind of a combination of 0 to 1 and established.
We have a Claude character, effort and team and that team is really focused on what are Claude's philosophies, what's Claude's vibes? How should Claude respond? And that's been an effort even from early days, but it's something we've focused even more on recently. In the rest of the AI landscape, you can often have these evaluations or evals, right, where you say, all right, how is the model doing at math or competition coding or agentic coding. It's a challenge to say what kind of vibes does the model have. We have some internal ways of doing that. Often you can try to use cloud to listen to Claude and then say, what kind of vibe does it have, but it also comes from just using Cloud a lot internally.

What are the unique challenges of building products alongside rapidly evolving AI models?
Mike Krieger: I think one of the hardest ones is, we are building fundamentally a dynamic model and a dynamic system. And so, as an example, we have in cloud we have a feature called artifacts where you can sort of work on a document or even a website along with Cloud. The model learns how to make artifacts, but the taste that it has in artifacts and how it changes and what language it uses and exactly what it does evolves from model to model. And sometimes you don't know how it's evolved until very late in the model training process.
So one of the biggest challenges with building products alongside doing model development is they're both moving targets. Our product is evolving, the models are evolving. Often the models are evolving up to like a week before launch, and we're trying to build products alongside. It's a very interesting dynamic system. It's what makes it exciting because the model can be creative and it can surprise you in a lot of ways. But it's also a lot more challenging than a classic product development.
How do you approach responsible AI development and user feedback at Anthropic?
Mike Krieger: I think it's really important to, as a product development team to be really upfront about the capabilities and the limitations and the risks. So you'll see when you sign up for cloud and you go through the first conversation. We really emphasize, here's what models are good at, and here's where they can still make mistakes. And here's the limitations. And I think it's important to lead at the beginning, because I want people to have the right mental model when using these models. They're not perfect. They don't know everything, but they can be very helpful and for a given task.
Similarly, I think goes back to the kind of the quad character piece. It's important for the model to also be aware of its limitations. And so often you'll find if you ask Claude about medical questions, it might say, all right, I can tell you more about this, but first, I'm not a doctor and if you're worried about this, then you might want to consult a professional. And it's not just a thing we put in for liability. It's a thing we put in because we think it's really important to have Claude recognize its own limitations as much as possible.
How do you gather and use user feedback to improve Claude?
Mike Krieger: Yeah, so it's an interesting question for us, which is how do we gather user feedback on cloud in a way that is like most helpful? And the way we've currently found, although I think there are probably other ways that we can continue to evolve it, is for every answer in cloud, we have a thumbs up, thumbs down. How did we do for both thumbs up and thumbs down, you can write a little paragraph about why it was good or was it bad. And it's so interesting because that extra bit of signal around why is the most important part.
And so we have a product manager, and she spends a lot of her time aggregating and evaluating and looking at how the model is doing out in the wild. And then you start seeing themes. So an individual answer maybe doesn't give you the clue about how you need to improve the model. But then in aggregate, you say, OK, Claude is being too verbose here in this particular case. To change it for the next model, or Cloud is changing its mind too quickly. So when the user disagrees with Claude, maybe the user is actually looking for a debate. Sometimes Claude is like, it's fine. Like, you're right. I'm sorry, I was wrong. But the user was actually looking for more of a back and forth. So that kind of conversational feedback is incredibly valuable.
The Future of AI: From Chat to Companions
What do you see as the future evolution of AI and where is the industry heading?
Mike Krieger: I think there's two areas of consolidation that I expect to see. One is on the model development side. Of things as these models, they're already very expensive to build and train at scale. As they reach even higher levels of intelligence, they're going to require that same kind of jump in compute and resources and I think we'll probably come down to 3, 4, 5 companies doing that, not as many. You're already seeing some kind of consolidation in that side of things. I think Anthropic is well positioned there. We've got really great partnerships with Amazon, with Google that I think will unlock a lot of compute for us.
And the other side is consolidation in more of the apps side of things because I spoke at the Y Combinator batch of startups recently, and everybody's working on something that is AI or directly adjacent to AI and that's great. There's a lot of products still to be built in this space, but not all of them are going to work. So in the same way as you saw that with mobile and social media where it's useful to have that because no one company is going to map the whole space out. Then you start naturally seeing, what's getting traction, what's going to get consolidated, what are good ideas, what were good design ideas, but wrong sort of business ideas that then will evolve into better business ideas.

What capabilities do AI models need to develop to become truly useful companions?
Mike Krieger: I think there's, when I think about where we are and where we need to get to, there's a couple of avenues I think are really important. The first one is understanding people for more than just a single conversation or even a couple of conversations. So we're not static, right? We are dynamic, we have relationships, we have moods, we have challenges, we have wins. And I think for models to feel really like they can work alongside us to really be part of our lives, they're going to need to develop a sort of empathy beyond a single conversation and really have that sort of longer horizon interaction with somebody. I think that's really important. I think that comes from contextual understanding and memory, for example.
The second part is the models need to learn when they can be proactive and when they should sit back. As people, we often know somebody's heads down working, we're trying to, we're not going to go interrupt them, or if they come to you for help, we can answer a question and maybe get back to work ourselves. So how do we have that collaboration with models in a way that feels really natural? As an example, we have Claude as a participant in our Slack channels at Anthropic, which is great, it can chime in and be part of the conversation, but we're finding it still either will not participate enough or say too much. So how do we get it to feel like a more natural participant in these conversations is important. And then the third one is around agency and independence. So how do we get the models to be able to take direction from people, but then go off and either do work or do research or be waiting for additional input and we do that over much longer time horizon in the background.
What's your long-term vision for how AI will change people's lives?
Mike Krieger: One of the big changes that's going to happen is the models will start being able to give you insights about your own self, which I think is very powerful, right? I've worked with a coach for many years. I think it's one of the most important ways in which I improve as a leader. I want that for everybody, right? Everybody can benefit from reflection and learning and iterating on the way that they approach the world. Right now, you can go to Claude and tell us about how things are going. It will probably be able to give you some coaching, but it's a very point in time. When I think about the potential, it's to be much more of an ongoing sort of improver or conversational coach.
I use this right now with Claude a lot. Anything that I write, I will put, if I'm writing a strategy document, I'll put it into Claude and say, what am I missing? What did I get like what poke some holes in my argument, and it's great to have that partner. I think that'll be one big evolutionary step. The other one that's, this is more speculative, but if models go from being single conversations, single chats to being more of long horizon, almost personalities, I'm curious what kind of relationship will form with the models. Like, will it feel more like a friend in some ways or a coworker in some other ways. I think that remains to be seen.
Advice for the Next Generation
What advice do you have for young entrepreneurs starting their careers?
Mike Krieger: I think in your early twenties, you have a unique place in the world because you're pretty in touch with the trends that like teenagers have, which is important, especially if you're building in consumer, but you're now able to like take those insights and make them into something like a project or maybe even a company. So it's a very special time in your life where you're like at the intersection of being a teenager, being really tuned into that, but being able to do those things.
I'd say the two things I would add is one, not worrying so much that every step needs to make logical sense. There's definitely things that side projects I did or explorations I did about at the time I was like, am I wasting my time here? But actually later, I find that it was connected to the next thing I did. So just trust that if you're driving towards a direction, it might take some very strange routes to get there. But as long as you're learning, I think that that's fine. And then the second one is advice that I got when I was 21. And I still think about to this day is, the companies change, the projects change, the economy changes, but the relationships you build in your career will be the relationships that you have over and over again. And so I was working at a startup as an intern, and it was full of people who were in their late 30s, who had worked together, probably 3 or 4 times since they were 20, and that really stayed with me.

How do you think about your own career trajectory and what defines entrepreneurship for you?
Mike Krieger: I think for me, when I was talking to Daniella, who's one of the co-founders of Anthropic, I told her, and I meant it, I hope Anthropic is the last job that I have. I think I see the opportunity here to be paired with research and build interesting products for many, many years because I think every year will be different. When I was 18, I had this like promise to myself that I wanted every year to feel different. And this year has felt very different than any other year that I've had being an anthropic. And I think that the year ahead is going to be quite different as well. And so that's how I really think about the next 5 years is just making sure I'm set up for consistently learning, evolving, working with interesting people on interesting products, and then taking the space at least once a year to step back and say, am I still learning? Am I still, eventually had Instagram. 8 years in, there's a time where I said, OK, I think I've gotten what I need to get out of this experience, and now it's time to try something else.
To me, entrepreneurship is about finding ways in which the world could be different and better, and then feeling empowered to go make that change. It's something that really drove me from a pretty early age. And as I've seen that manifest both in the ways you can change your city, the way you can change the way people relate, of course, with Instagram having global impact, large or small, it's really about identifying like what could be different, like as getting curious about the world and then also getting curious about how you or you and a small team can see if there's a change to be made there. And I'm very excited about the way AI will empower people to ask that question and also answer it.