Jeremy Le Van, co-founder of Sunrise Calendar & former Director of Design at Microsoft, talks to Maze about the journey from designer to founder, building businesses through design, and the lessons made along the way.
The Optimal Path is a podcast about product decision-making from the team at Maze. Each episode brings in a product expert and looks at the stories, ideas, and frameworks they use to achieve better product decision-making—and how you can do the same.
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Ash Oliver:
Welcome to The Optimal Path, a podcast about product decision-making brought to you by Maze. I'm your host Ash Oliver, UX Designer, and design advocate. Great products are the result of great decisions. Decisions that deliver value for customers and the organization.
In this podcast, you'll hear from designers, product managers and researchers about the ideas and forming decision making across all aspects of product development. Today, I'm joined by Jeremy Le Van. Jeremy is a design leader with a passion for building companies. He's previously led teams as the director of design at Microsoft, was VP of design at Cowboy and formally co-founded Sunrise calendar. I'm so stoked to chat with you today, Jeremy.
Jeremy Le Van:
Thank you, Ash.
Ash Oliver:
I wanted to first kick off finding out a little bit more about your background and journey into design. So, let's start by going back in time a little bit. You've said that you've gotten into design fairly late and that you've felt that you were never really good at drawing compared to other designers. You've said that you fell into design in a way. Can you talk to me about the early start of story in design?
Jeremy Le Van:
Yes. Sure. Well, back then, I feel old when I talk about this, but I'm not. So, back when I was student, I actually didn't know design was a thing you could study, you could go to a design school or art school and really hone the skills to become a designer. I think it's a bit more clear now or obvious in a certain way. I've always been interested. I guess like a lot of people back then at building websites and essentially playing with the internet, building computers and then from one thing to another, I had this opportunity to study here in Belgium at a design school, traditional graphic design. So, I really went through the basics of design, graphic design typography and whatnot, and drawing as mentioned.
Jeremy Le Van:
That's how I came about, "Okay. I can link those two things." Building websites and obviously before the iPhone and apps and the ecosystems came out to have these opportunity to really build my skill back then. One thing leads to another. I decided to focus more on new technologies essentially. So, websites and then websites through apps. And again, building apps back then, or mobile apps I should say, was a different beast or a different experience for designer because we had different platforms, Blackberry was a thing and not just Blackberry, obviously you had NOKIA, you had a Windows Phone at some point as well and Android was very early.
Jeremy Le Van:
So, the design language, the design systems, the entire ecosystem that we know as of today, didn't exist. So, we had to also get some cues from what other people were doing. So, I had this opportunity in 2007 to move to the US, to San Francisco, that's where things started. San Francisco, SF, was very different back then in many ways, both I would say socially, like the way the city worked and also just the fact that there weren't that many companies or the ecosystem was just not as vibrant, I would say, as it is today. Facebook was still very, very small or much smaller than what it is today and Twitter and social media was also very new. So, I had this opportunity to go to San Francisco, really focus more on my programming skills and design skills and more specifically had the opportunity to join a company in San Francisco, NSF back then. So, really learned on the field essentially on how to build great apps and had also the chance to meet great people.
Jeremy Le Van:
And that's how it started, but really going back, just reiterating on this part, I think I'm very lucky or happy that I went through this traditional design background in order to really get basics, I would say, and then move on to the next frontier or the next thing where everyone is trying to go or a lot of people are trying to move towards from building websites to building mobile apps. And I really wanted to be front and center and part of that movement, I would say, or trend. So, very lucky and I guess at the right spot, right place, right people, right timing. It helps for sure.
Ash Oliver:
I hear all lot of designers that have come from more of the traditional, either advertising or graphic design background and you're talking about the fundamentals that really helped seed your skillset, going into programming and more interaction design or your UX design. Are there anything, any fundamental design practices or skills that you still think are, even if a person, a designer would go to school now in a much different technology environment that you still feel are centerfold to a traditional graphic design degree?
Jeremy Le Van:
First of all, I still use that framework if I can call it this way, at least the design school or the teachers or my mentors back then when they would really expose me to other things, not just design per se, but I guess typography in general, very broad design language, and also trying to get inspiration from what's out there, but not just what's in your field. So sometimes, and we're seeing this obviously a lot, Instagram is trying to become TikTok or one app is trying to become another, snap is trying, especially in consumer apps, a lot of apps or behaviors are being copied. When someone launches something new or when and to me, this is really what design is about. You really have to try to get your inspiration from what's other, you can get exposed to architecture to how cars are being designed, how CDs work.
Jeremy Le Van:
I think you can get a lot of inspiration essentially out there, not just "in your field or just design." Again, design means a lot and it nothing in a way, because it's such a general topic or a concept. But I think in hindsight, it really one of the skills that I still apply today, that I really try to sharpen over the years, trying to get inspiration essentially from other things, not just technology or not just what's being on today. I think lot of things obviously work also with its analogies. And we've seen this with technology and design a lot, right? Because essentially we're using a calendar today or we're using our phones in a certain way while phones have been around for quite a bit of time, obviously they weren't wireless or in the same shape or didn't function the same way, but at least we always have a cognitive attachment I would say to how things should work in a way, how we communicate or how we use certain, essentially the UX, the experience behind the objects and things. And so, I would say that's probably my biggest takeaway.
Jeremy Le Van:
That's what's fascinating about coming up with new concepts, new ideas, designing new interfaces and experiences. It's essentially trying to be original and come up with original ideas. So, that's probably today, still my biggest takeaway from back then.
Ash Oliver:
I love that. I couldn't agree with you more. It's like trying to be more of that social anthropologists and look outside of the bounds of your own industry or what you're exposed to, I think that's where innovation lives for sure. So, that's so great to hear that's been a through line in your career. I want to really focus on your time at Sunrise because you are the co-founder and it's a pretty wild accomplishment, especially leading to its acquisition Microsoft. I'm curious we can talk about some of your earliest memories about founding that company. What prompted you in the beginning to bring your design experience to launch your own startup?
Jeremy Le Van:
I really saw a shift in my brain, essentially the way I functioned and the way I saw things prior to launching my own company and startup, I had this idea of, okay, I'll, like you said, you're designer, I do graphic design. And then you work in the studio, you do icons, logos, beautiful typography and identities, things like that. Or you can work, like you said, at agencies for clients and be more on the advertising side of things. So, trying to sell essentially more stuff in a way or services, but those were historically, and where we came from. And then the shift of, well, I'm going to be my own boss, but beyond being my own boss and running my business, "into the design world, I'm also going to make a product evolve."
Jeremy Le Van:
And I think that was really for me, some of the striking moments, because I had this opportunity and truly I felt evolved from this mindset of being a designer, working for someone or working at a startup for someone else, to well, maybe I should give it a shot as well, myself and being inspired by other entrepreneurs who didn't necessarily were designers, or maybe had some design background or were interested somehow to design, but not necessarily designers as we know them. And I think back then as well, like Airbnb is one of the first examples there. Obviously a very successful company led by designers first. I mean, with a similar backgrounds and again, like when you see to what level either Brian Chesky or Joe Gebbia were able to design the organization, it's not just designing a product, it's designing how people collaborate together.
Jeremy Le Van:
This is to me as a designer, it's a very powerful thing. Like you said, the anthropologist in us or anthropologies bits connected to the business is fascinating because you don't just get to design a service or a brand or a product that people will use obviously, but also the way people will organize themselves. And I guess in the end, it was the biggest "excuse" for doing it. Essentially the part I was the most excited about, building a great team, getting excited about what I build in the end. I don't want to say it doesn't matter what I build, but it's about solving problems. As designers, we love to solve problems.
Jeremy Le Van:
I got very attached to that, to the fact that my ex co-founder and I, we thought a lot about how we want people to collaborate. We also saw, obviously from our experiences, this doesn't work for us, this works. Maybe we should give this a try. And, obviously again, trial and error, some things work, some things don't necessarily work right away, or maybe you need to iterate a bit more on how things work and even more today with the remote setup, people get a taste of a new way of working essentially. So there, again I feel this ongoing mindset of being able to experiment within your company with people is fascinating.
Ash Oliver:
So much. This is, like I said, a segment topic that I'm really, really passionate about. And I think we're starting to realize that design goes far further than just the visual output. I think that's just in everyone's mind that, that's what we think design is. And even in UX, it's way more than that. And then you branch it out and you start to apply design thinking to how you build your business, how you organize your team, how you go to market. Marketing as a product through design, it's all connected to that. So, I think there's a real competitive advantage for designer founders that are able to apply that design methodology and practice and experimentation to every aspect of the business.
Jeremy Le Van:
Exactly. We tend to forget how things were before and things have shifted quite a bit. Things went really fast from where we are today to where things were back then. And I think both engineers or developers and designers didn't necessarily have a seat at the table in terms of decision making. And now that we are seeing more founders, designer founders, or engineering founders, re-thinking how people work or it's very refreshing in that sense.
Ash Oliver:
Really interesting. I'm curious about still thinking about that the early days at Sunrise, how did you know it was worth building?
Jeremy Le Van:
It's a great question because it's something that, I mean, in this process right now where, I know I want to build something new, I still have this itch, I have a bunch of ideas I'm [inaudible 00:12:37] on or exploring at the moment. And, I had actually this question earlier this week or a few weeks ago about why did I start Sunrise? I think there was obviously some part of me that was a bit naive I would say, I was younger. It helps. I was also a bit more naive in the sense that, well and it is still today, what does it cost me to start something? If I would say the main things are being taken care of and you can take this leap. I was like, well, I shouldn't be afraid of jumping from being a designer employee to being a designer founder or being my own boss.
Jeremy Le Van:
And I really thought back then, and I'm still thinking the same today, there was really no big risk in the sense that essentially if things go wrong, or if things go south, I can just get back to a normal job and just be the designer I used to be and work as an employee. But I decided to take this leap because I felt like, well, it's worth giving another shots. I think at the end of the day, it's also, how passionate are you about solving a problem on your own or for your own? That's a tipping point. So with my ex-co-founder Pierre, we worked for a year and a half together. So there's this good synergy connection between the two of us, why not give it a shot and worst thing, we'll just go back to what we did before. Maybe at different company, maybe not at the same startup we used to work at, but at least it's worth doing it.
Jeremy Le Van:
And I'm saying this with a different lens today obviously, because now I'm a father, things are a bit different once you have responsibilities, I totally get it. That are things you need to take care of, but at the same time, I also quickly understood back then already, well, in a way, it's the best way any builder or any person to build value over time by launching your own company, if you really believe in the problem you're solving and the solution you come up with in the first place. So, we were very convinced about what we were exploring and we felt well it's worth the shots. Obviously things that were being solved back then 2012, 2013 are not necessarily all relevant today, or maybe not in the same shape and form.
Jeremy Le Van:
So if I had to do it all over again today, I wouldn't necessarily go with the same strategy I went forward, but I'm still seeing today and being contacted today regarding productivity apps and calendar apps, because I feel it's an ongoing problem, right? Just like email or communication, people are always looking to challenge the status quo. It's all about really taking this leap of faith and go for it. But I think you should do it for the right reasons. That's probably my biggest takeaway. On the other hand, I also see industry, many people trying to start a company and they don't necessarily have the right idea, or maybe they're trying to convince themselves maybe too quickly. So, I think it's about finding this balance, but I think if you have this urge and you already have like over 50% I feel.
Ash Oliver:
Yeah, definitely that belief as stamina, it keeps you going. And when you're thinking about that time and ultimately challenges arise at any point in the business, but in some of the beginning part of your journey with your co-founder, what were some of the earliest challenges that you two faced in the beginning?
Jeremy Le Van:
Great question. Well, the arguments, I would say you have to be okay with that, especially with the co-founder. I used to say it back then and I still believe it today. It's essential, if you are married with someone in a way, so it's a very intriguing or interesting relationship having co-founders and I've seen many shapes and forms. You have single founder, quite impressive. Obviously I'm just a duo and I think that works great, but then I've also seen teams with like four or five co-founders and the more people you add into the equation, the more complex it can get, or it gets by default in a way. And so, the challenges that we face I would say is probably like vision alignments, ego. And again, that's fascinating because then you realize it's easier to say, say today with in hindsight, or at least with some perspective that in the end, what kills your startup is not necessarily the competition, but it's more like you, your ego, when I say you it's you or your co-founder, the relationship you build.
Jeremy Le Van:
So, it's more like yourself and your team or at least the core/co-founding team is more like the essence that you need to nail. And if you screw it up, it's over essentially, it's not necessarily your competition who is going to kill you or destroy your idea or your product. I think it's more the mentality within the company and the way you accept your feedback can agree that maybe you don't always come up with the best ideas and being in the driver's seats, you want to lead, you want your ideas to go forward. And that was probably the biggest challenge. On the other hand, I was lucky because we had a great match. My co-founder and I, in the sense that we talked about the anthropology bit and the fact that I think we had a good match, essentially.
Jeremy Le Van:
I think the two of us and personalities works well. I didn't necessarily have too much of an ego to challenge everything Pierre would say. And on the other hand, I think Pierre was also willing to give me some freedom in certain things. So, we were able to move forward. I guess that's the main point, it's about being able to move forward, but then it's also about finding, or having this person, CEO, who makes a call and is responsible for the decision. So, it's definitely tricky, since I'm looking to start something else, I'm spending, sorry, way more time talking to people, really understanding their passion, their vision, the drive, why they want to do certain things or accomplish certain things and going all the way with this naive version, was very different from what I would do today.
Jeremy Le Van:
I think in hindsight, you need a bit of both. You need to be a bit naive, you always need to be a bit naive, otherwise you're trying to be too rationale and too objective. And I think at some point you just need to trust your guts and go for it if you truly believe it.
Ash Oliver:
I think that's absolutely true. Probably a lot of people may overlook a lot of the people things that they have to consider, especially and potentially finding a co-founder, really assessing if that's going to be a good marriage, as you say, and compromises and styles of work and how you can also potentially find someone that as you mentioned, challenges you in the right way isn't necessarily just placating to your ego, but it's connected to, you had said before, because you have this internal urge and belief that so tightly linked to ego. So, I think that's why so many people have a hard time dismissing ego from a lot of the decisions that they make, because it is so intrinsically tied to them and what they started-
Jeremy Le Van:
Exactly.
Ash Oliver:
It's a tough thing. And to get all those right.
Jeremy Le Van:
One more thing I would probably add is, as a designer, I think we have usually strong opinions just because it's part of the way we work. We come up with different user experiences. We come up with different interfaces and interactions and we have to be opinionated about how we see the world or vision of the world. So, you also have to find this match or marriage with a person who respects that. And I was lucky that my co-founder would respect that. I think it gets hard when you work with someone or you have to work with someone who doesn't necessarily value that skill.
Ash Oliver:
Would you say that there's anything that you would pinpoint for those that are ready to take the plunge and they're looking maybe for a co-founder, what would be something that you would say, you would look for in that partner besides knowing that it's going to be that marriage aspect, even down to where would you go look for someone like this?
Jeremy Le Van:
Finding a co-founder is definitely a struggle. It's not easy and I think the best advice is working with people you work with or friends or people you know is always easier. And having being through different rounds, I've been talking to personally after Sunrise as well, two people outside my circle or also wanting to start companies and there wasn't necessarily a match. Not that we weren't great people or nice people together, it's just that the match, it just didn't click for some reason. So, I think it's definitely better to go seeing your network and even more with previous coworkers or friends or relatives or people you know, that's probably the best tip I can give.
Jeremy Le Van:
On the other hand, I think starting something on your own first, if you true believe in something and then finding people on along the way is also possible. And I think we don't necessarily talk enough about this, but I think it's also a way for you to attract certain people who didn't necessarily needed to be there in the first place, but who can tag along and again, like in terms of shares, in terms of, I mean, to me, in a way these are all details. Obviously if you [inaudible 00:22:05] give them 50:50 or find the right percentage in terms of equity, you can always do it later on. It doesn't need to be done all day one when you incorporate a company. So things can always be solved in that way.
Jeremy Le Van:
And so that's why I think it's also a good way if you truly are convinced about the problem you're solving to go just on your own first, even though it might sometimes sounds scary, but again, as designers, as builders and speaking of which, I went back to coding a few months ago because I realized, well, okay, I'm looking for a technical co-founder, but didn't find the right people or people I wanted to work with weren't necessarily available or not in the right setup et cetera.
Jeremy Le Van:
So, I was like, well, I can just also maybe start something on my own and I'll meet someone maybe on the way there. I think it's about removing the pressure, but then it's not just designing or building the product. It's also designing, building the company. And I think you need to project yourself with this person and see if you align on the values and the culture you want to build with that person. I think it's probably, if not, maybe even more important than the product itself, are you aligned with the way you're going to work? Because you can probably align quite quickly if you agree on the product or on the solution and the problem in the first place. But then I think it's the underlying foundation to me is, are you seeing the setup, the remote versus no remote, et cetera. How do you see all that, even more so today?
Jeremy Le Van:
Again, I was lucky enough to have a great first experience, but I also realized not everyone wants work the way I wanted to work. And even today when I shared with other people or not necessarily designers, I mean just broad array of people, I realized a lot of people work very differently. And so, if I wanted to find a co-founder who wants to work just like me, I need to someone who wants to be in the similar setup as I want to be. So, there are definitely a lot of things to answer. I mean, it's an equation.
Ash Oliver:
Absolutely. Such sage advice though, because you probably do get really caught up in thinking about getting all of the practical things in mind.
Jeremy Le Van:
Exactly.
Ash Oliver:
Do they have domain expertise? We work together before, do they agree on the problem, motivated about the product, but maybe overlook all of the big things around actually making it happen that might not be complementary to the two or one to many that you might have in your co-founder. Yeah. That's wonderful. Lastly, what I want to ask is just about your time at being at founders pledge. You've written that, and this is a fact I believe, that the majority of us aren't building products that will tackle our most pressing global challenges. This is something really, really important. So, what is it that founders pledge and why are you specifically a part of it?
Jeremy Le Van:
So, founder's pledge is essentially nonprofits, who has set up in London initially by David's, great, great person who used to work in finance. And so, David decided to quit finance in New York I believe to launch this nonprofits in the UK first. He decided to launch this just to empower founders, that they can do good through their businesses essentially, because you might do well on the business side of things, but what's your impact at a social level or at a bigger level in terms of impact. And obviously when you think about impacts, you think about climate change, you think about saving animals, but also just at a human level as well. I mean, the inequalities, there are a lot of things that goes into that. So, he decided to give exits to different organizations, NGOs essentially, that they would do research on and essentially offer you a full service where they analyze the nonprofits, so that you just don't give away to any nonprofit.
Jeremy Le Van:
And that dollar to dollar amount is as high as possible. So, they're kind of doing this research on different topics and they help you with that. And on the flip side, it's also a great way to meet other founders or people who have founded companies that are in a similar mindset. And so, they organize retreats. They organize events every year. It's really refreshing and it's another format to essentially networking people. And so, they started slowly grow in different countries, both on the east coast and west coast and also in France, in Berlin and essentially where all the hot tech hubs live today. I know their goal was to potentially expand afterwards with maybe employees and whatnot, but it's very interesting. And I was able to be part of that and give pledge towards certain causes that to me were very important, and also learn people on the fields because you also get to meet people work at these NGOs and they tell you about how things go and where your money is actually going to go.
Jeremy Le Van:
So, that's something that I've been following for the past couple of years now. And I also been able to meet great people through that. It's a good way to essentially give as a founder, if you have an exit or some companies also IPO, so they're, I mean, they're different formats essentially to give.
Ash Oliver:
I'm so glad that you are a part of it. Thank you for your contribution there. Okay. So, I'm going to move on to our final questions and you can answer in as much detail as you want here. These are questions that I ask everybody on show. So, the first one is, is what's one thing that you've done in your career that has helped you succeed, that you think very few people do?
Jeremy Le Van:
To me being a designer, it's all about details and being detail oriented. And I'm the type of person who is, like many designers, not necessarily saying all designers aren't detail oriented, but I think it's one of the skills that makes a great designer and at least someone who is careful about his work and passionate and I think the fact that details matter, but not just to me, not just the fact that I was detail oriented in the work I was producing, but also in how my team would perform, how the company was doing, if everyone was happy on the team, working out essentially the details, because usually it's details that matter. It's one of those things that are often overlooked because, well, we have no time or this and that. And, I guess that's where maybe the devil really lies, is in the details. So, that's maybe one of the things that at least I had some positive feedback from my fellow team members back then. And yeah.
Ash Oliver:
That can be a huge competitive advantage in your work to be that thorough and intentional with decisions. That's where execution lives in my mind. So, that's awesome. What's a system or process or habit you might even think it's totally outlandish, but system or framework that you've created for yourself to help either accelerate your work, your career or your personal goals?
Jeremy Le Van:
As a designer, again, I think I tend to overthink sometimes a bit too much. And it's maybe again, something very true to designers or builders, like we need to think about a lot of things, a lot of edge cases, about a lot of situations. So, sometimes we tend to overthink situations or experiences, and we build this into our designs.
Jeremy Le Van:
On the other hand, I realized the best decisions have taken were probably when I didn't think too much. So, I guess more spontaneous and going back to what we talked about, I would say, just the fact that I decided to make the leap and go for it and start a company as a designer, I think that was probably one of these decisions I didn't think too much about it. I just felt it was right. And I was aligned with myself and with my goals and I realize in hindsight, because it's always easier to do [inaudible 00:30:25] this way to connect the dots backwards, that I was able to probably make the best decisions when I just followed my gut and didn't think too much. So, I was going to say maybe being less of a designer in that sense, because again, designers tend to overthink sometimes too much, but I think that's where things really were shaken up and went forward, but positively.
Ash Oliver:
What is the industry related book that you've either given or recommended the most and why?
Jeremy Le Van:
I would say I really liked the, I think today it's almost given, but I remember back then, it wasn't necessarily before starting my company, I would say probably the Sprint book by-
Ash Oliver:
Jake Knapp.
Jeremy Le Van:
Exactly. And why, because there are two things. I think as designers, we need to be pragmatic and we need to know when to ship. And I think having a timeframe and setting into motion and keeping the momentum and ball rolling, I think is the most important part. It's better to move forward and just reiterating on some, chewing on the same thing. At some point you need to ship or at least get some feedback and I've experienced this so many times in my work and career when I spend way too much time on a problem or trying to solve a problem or designing interfaces and not shipping fast enough, nothing good came out of it.
Jeremy Le Van:
So thank God. Thanks to this entrepreneurial experience, I really had to, I guess, be more pragmatic with myself, with my team, with my co-founder. So, I would say that's probably one of the biggest learnings I got from being able to be pragmatic and ship. So, I like this book, at least for the format and the fact that now it's a thing of the past or a thing it's a given as I mentioned, like the fact that you ship on a weekly basis or you reiterate constantly something that wasn't always the case. So, I think it's a good reminder.
Ash Oliver:
Absolutely. What do you believe that you're known for?
Jeremy Le Van:
I would say probably listener. For me, at least, I think it's the fact that I like to listen to people and I'm interested in humans and in people in general. I can see why this works well with me and why I can be good at it in terms of listening, understanding, people's needs and honestly, that's also why I really enjoyed being a manager because I was able to be there to essentially provide the best to my team, not just as a co-founder, but also at Cowboy or even at Microsoft as well, being able to move things forward for the team. So, I would say being able to listen, because in this crazy world where a lot of people talk, I think we don't have enough people who listen, we have a lot of people who talk and-
Ash Oliver:
So true.
Jeremy Le Van:
And we probably need more listeners. So, I guess that's probably one of the things that I'm known for.
Ash Oliver:
That was amazing. Thank you so very much for being here and sharing all of this wisdom. Where's the best place for people to find you if they want to learn more and learn more about what you're up to?
Jeremy Le Van:
These days probably Twitter. I mean, even though I'm not like necessarily super active, it's definitely the place where I hang out a lot and otherwise I would say LinkedIn, but mostly I'm mostly a big Twitter user.
Ash Oliver:
The optimal path is hosted by myself, Ash Oliver, and brought to you by Maze, a rapid user testing platform designed for product teams. If you enjoy this episode, you can find resources linked in the show notes. If you want to hear more, you can subscribe to the optimal path by visiting maze.co/podcast. Thanks for listening and until next time.