 Hey everyone, this is Carlos. I'm the founder and CEO at product school today. I'm here with Paul English Who's the founder of kayak comm? I'm sure? 99.9% of the audience has used your product Paul. How do you feel? It's fun. I have to tell you it was cool the first time I was on a plane and Saw someone sitting next to me using the kayak app on their phone. That was fun Yeah, I think I got more it is true now that we become a Household name. I think there's over a hundred million people that use the app But for some reason the first time seeing it in the wild was the most exciting for me Do they still give you feedback or ideas? Yeah, I love getting you know doing primary research It's the best thing as a product person is talking to actually users particularly in the wild I mean we all have done formal usability testing and we use different tools and bringing people into the lab And do usable testing on video, but nothing is quite as good as running into a user in their environment When they're actually trying to use your product to get something done. So that was always really fun for kayak and the early years of kayak This is gonna sound really strange, but I used to kind of hang out in the airport I sometimes would buy a flight the cheapest flight I could say Boston in New York just like get through security and then I would sit in the terminal And I would approach people it was just a little crazy that I did this But I had two phones and I go up to people and I would say Hey, can I talk to you for a minute? I go. I'm a programmer and I work at this company building travel software I'd love to show you what we're working on and I'd give them one of my phones That's a his the app Can you check it out and I would say do you mind if I record this because I want to show all the other Programmers of the team and I'd give them one of my phones and I'd record them on the other phone and then bring That back into engineering and it was cool I didn't do enough of that, but I did that in the early years when we first had our app And you were doing user testing before it was cool because now there's a whole new suite of products and process There's no replacement for being with the user when the user is using your product Yeah, I actually learned that skill back it into it many years ago I had a small e-commerce company called Boston light We built a product called Q shop like quick shop. It let people set up storefronts very easily it's sort of a precursor to us to Shopify in some ways and After I sold my company I worked for intuit for four years I served as VP technology for small business for QuickBooks and other products and to it I thought had mastered the The study of how to learn from users and they actually did and maybe my airport stocking was based on a Technique that intuit used to do which is back in the early days Quicken engineers would go to staples or stores. It would sell a quick end and they would approach people as they saw them looking at the product They would say hey, I'm not your program. I worked on that product I'd love to interview you and watch you use it and they actually somehow would talk people into letting them Visit them in their home and use into its early products So when I first heard that story it into it I was like whoa That's like seems like crazy boundary crossing But it's so cool to observe people using your product in their environment, right? Because you want to see that what happens when they're using your product and they get a phone call What happens when? They're using your product and their kid comes bursting into the room like do they get distracted? Do they do they go back to product that they lose their place? And I think seeing them in the actual environment what I actually need to get a task on that's the best thing that a product leader can do I Like that point sometimes I think we assume that the user research is With the user looking at the screen focusing a hundred percent of the attention on on the screen Well, in reality, this is story behind you in an after that has to be taken into consideration Yeah, one thing that caught my attention is you said the engineers were the ones doing this type of research For a company as big as into it Why do you think they were intentionally asking engineers to get off the get off the building and talk to users instead of the user research team? For example, yeah I think in the early days it into it the wasn't really a user research team and Scott cook who's a mentor of mine I'm still good friends with him. He's the founder into it He really believed in primary research and he didn't think it should be limited to the product team He really wanted the engineers also to get to interact with customers So maybe I'll have to because the original sort of follow me home Processed it into a predated my time it into it But I know it was a mix of engineers in product people both who would do that That is really cool and I think there's a lot of parallels that can be drawn today We are seeing a lot of product small startups medium-sized companies where they still don't have a user research team now these responsibilities falling on their product or Engineering and regardless of the title. I think it's just a good practice for everyone in the organization to understand the user Yeah, absolutely. I mean, I'll tell you another funny secret about kayak, which is a little bit unusual We did a lot of things different than other software computers But one thing is unusual about us is in first seven or eight years You're gonna think this is blasphemous, but we didn't have any product managers. I mean I had three designers Lincoln Sidra and young We had some really talented UI engineers and then I would kind of do the product plan Working with those guys and I was someone who my title it into it was CTO But by the time we my title at kayak was CTO, but by the time we Started kike. I think I coded my first year and then One of the engineers end up throwing out my code and replacing it And so I I stopped being technical and I started spending all my time on product and design And so even though I had a CTO title my real love for product these days is on product and design More so than how do you actually build something? We even mentioned design That's is that those are big words for someone coming from the from the technical side. How do you get into design? I've always been obsessed with design. I'm a little bit OCD I studied typography when I was in college and I even like designed my own fonts back in the day I really cared a lot about typography and how things looked and In my first job after I got my master's degree. I Replace the user interface for a mature product. I rewrote the whole user interface in an extension language to let other people change the UI and in doing that it wasn't just a technical task of Recoding how menus appear. It was also and how should menus appear and so I was really concerned with Speed and performance and responsiveness Also earlier in my career like very very early micro of my first commercial app was a video game that I created while I was in high school and I used to be a pretty serious musician back in high school and in college In fact, I think in in college my master's thesis was I developed a music synthesizer But doing as a musician doing design of games You became really obsessed with timings not just sound effects But timings in general and you go out like very sensitive to say 50 millisecond differences between response time and that kind of started my journey and ever since then Really my whole career. I've worked on the user interface that has always interested me much more than back-end or database on network and I know that you you also Redesign apps that's for fun such as Twitter and others How have the does that connect to your other real projects? Yeah, so Design is something that I love and I I'm not like really a true True designer Myself I work with really great designers But I work very intensely with them and sometimes I'll do a lot of times I'll do drawings and take pictures of my drawings and email the designer They'll put it in figmob will go back and forth a lot like very very interactive. I do like redesigning other products just as a Experiment it's one of things that I do when I interview product leaders and designers both because I also like product managers to have a UI sense if they're gonna be working on a consumer product But I frequently will ask a product leader as I'm interviewing them to say tell me an app on your phone that you use a lot And they might say tick-tock and I'll say great I love tick-tock to tell me what you hate about it like what don't you like about tick-tock And if you were the product lead at tick-tock in charge of the next version What would you do differently? Like what would you tear down and what would you rebuild? And I just like that assignment of trying to redesign things I had lunch with a friend today my friend Lincoln who's a designer and We literally sat there and shred the menu like the topography of the menu or the place he went to and It's just design is something to Be aware and be present of your surroundings and part of being present in your surroundings is to Talk about your surroundings and engage with them and talk with other people about them And that's really what design is for me I come from a technical background as well and I have to agree with you because while I don't have formal design training I learned to develop my own point of view an appreciation for design and interest for the user research And and I think that is something that I expect from other product leaders that regardless of their main responsibilities They need to feel comfortable having a conversation with designers and be a facilitator like obviously it's almost impossible to find someone who's equally good at everything But that doesn't mean that you cannot have the curiosity to get better at everything. Yeah, that's exactly right and even within design I mean product as you know Involves a lot of set of skills to be really successful product leader There's a lot you have to learn and become good at and in design as well. They're very different types of designers, right? I mean there's Visual designers who do nothing but graphic design. There's interaction designers There's a lot of different types of design and but a lot of it. I do think is based on that curiosity and reflection I resonate with an example you gave about the restaurant because I'm also Obsessed sometimes when I go to a restaurant and looking for things to improve not just from the menu But from the way maybe the person is approaching me or the layout of the tables and everything I think not just product people designers founders in general They just have that obsession for doing things better or at least we have an opinion on how things should work and and I think an art the art of managing those personalities as a founder as a product leader It's something that at least I didn't learn in school. So I'm wondering how do you go about? Leading a team because I can't imagine your experience when you were starting kayak to where it, you know Became was very different personally as a leader It's interesting. I mean another you know, we just mentioned curiosity Another key aspect of good designers and good product people is compassion. I find that I I think more than most careers in tech people that are great Product leaders are great designers are very compassionate people and that they're very tuned to others and Compassion is something that I think is a skill that can be learned and be honed I guess lecture at Rhode Island School of Design every semester I have a friend as a professor there or in Sherman and he teaches a class actually an entrepreneurship at the design school and The exercise that I always give the class Before 24 hours before I show up I have the professor email the students and say take a picture of something that annoys you it can't be a picture You took yesterday it asked me picks you take today It can't be a picture you find the web that's your photo you actually take and just email it and then during my Presentation I'll flip through some of the images and we'll talk about annoyances and irritants as inspiration for design and Good designers and good product leaders will notice irritants around them They'll notice as you say you're at a restaurant the way the person approaches you You might notice they there might have been a better way for them to engage with you And if you train yourself to be to notice your environment really well You can find solutions. I think innovation is actually really easy I think the hard thing is figuring out what problems I work on Most startups fail for two reasons either There's Implosion amongst the founding team and they create a toxic culture and everyone leaves which is sad or It's not that their code doesn't work. It's that they build tech for problem. No one cares about So I think as an entrepreneur your two most important skills is recruiting, but then also Locking in on What's the product we're trying to solve here? And this is a problem that really a lot of people have and is it a really big problem or a small problem? So having that connection of the customer and the compassion for their problem is step one on the journey to creating a successful products And I can totally see a connection between these and the previous example We were discussing because for people who are obsessed about looking for opportunities and the end of the day You can't fix it all and you have to prioritize and and I think that creating that type of List of things and having me having some self-compassion as well to know that you cannot fix it All and that you also have to move on Otherwise you are going to be obsessed about things that you know, don't really move the needle So that was a good piece there. I didn't think about before I know that you have a motto You live by which is team first customer second product third that sounded kind of controversial the first time I heard it so I would love for you to elaborate more Yeah, I Take that quite seriously as I think about where I spend my time every day If I look at my Google calendar today and think about the meetings that I've been in Most of them around the team and kind of the dynamics of the team it's either recruiting or tuning a team to work better together and It's that Relentless focus on kind of the psychology of the team and tuning the team That what's if you're a good recruiter and you're good at managing kind of the psychology of a team That is what leads to a team that can create magical products If it's a team that is you know really strong Contributors but also who really loves working together those that seem to create magical products So I think as an entrepreneur my biggest responsibility even to my investors is to cry to try to create teams with the mojo Who can create this magic? If you are able to create those teams You then once you're assembled we say let's Talk about these customers. Let's talk to these customers and that's figure out how to solve that problem Let's figure out how to like dazzle them do something like really amazing for those customers And so to me it's like organize the team and lead them Solve something amazing for customers. If you do those two things really well, the profits will follow And I and I think that a lot of times the first time founders or even Product leaders tend to focus on product first because that it seems like the obvious move It's like what you've been trained to do build something However, you can only go so far by building yourself, right? And I think that flipping it and focusing more energy into building a team that can build a product putting your ego aside It's it's hard, but I don't know any other way to scale a corner and organization Yeah, there is a danger of building a product too early in that if you spend a bunch of time back in the lab Not talking to customers just working on a product You end up falling in love with your own product And then when it's time to put it in front of customers and they give you feedback You tend to reject their feedback subconsciously because you have fallen in love with your product and you become defensive about it If instead you have compassion for customer problem on day one And checking in with customers about is this solving their problem? Do you really understand their problem? What are the implications of their problem? I think that can lead to the sustainable product which will grow on its own So Paul, how do you learn all of this because back in the day? I'm not these days. It's a lot of content and more people talking about the importance of focusing on the customer first But back in the day that wasn't the the main message. So how did you learn this by yourself? Yeah, I grew up In a family of nine so i'd seven there were seven kids and my parents they're family of nine and I grew up in a small house And as a kid in a small house of nine people you're tuned to the dynamics of what's happening around you So when I first started working on software products, I was just very tuned to people's feelings and emotions And I wanted to see their emotions when they saw my product So if I got people really excited about the video game that I created when I was in high school I knew this was something great if people said this is fun and then they stopped playing I knew that I hadn't built something Innovative enough yet. So I think it's a just being tuned to people's emotions And in knowing that you know, those of us who work in the tech industry Privileged enough to work in the tech industry. We're building technology But our technology really only scales if people get positive emotions from using it and I've been spending a lot of time to Getting touch with my emotions And I I've done coaching and different things and I still it's a working progress for me And so I find fascinating when you mention things that has compassion or being tuned with people's emotions Is there anything in particular that you need to Explore some of those concepts deeper. Did you get any external help? Was there any course any mentor anyone that at least helped you? Yeah, it's funny Two of my siblings are therapists And buddhists and we talk a lot about emotion and compassion. So I learned from them a lot I took a a seminar a class on Compassion at the Cambridge Incent Meditation Center just outside of Boston And I think again compassion Is a skill that can be honed and I think Becoming a more compassionate leader Is good not just for your team, but it's good for your products and it's good for your customers So I really do think You know we talk about the restaurant when that waiter approaches you You can think about How they could have approached you in a better way like what should have they said that would have been more efficient And more friendly whatever but you also should think about how's their day going And what would it be like to be that waiter in a really crowded restaurant? So I think just Being trying to be tuned in to the emotions of people around you Ultimately leads to building products that get good emotion response I know that sounds crazy, but it is how I think about design It does sound crazy. I agree But I also agree with what you said because I think the first time I got exposed to these tools And basically for me was giving people the benefit of the doubt Or as you said like maybe that person had a hard day. Maybe that person You know like instead of assuming all that person doesn't know and has a Really trying to give people a chance and And lead by example I think those are concepts that are really hard to master I can't claim to has to master my enemies But I'm loving this conversation because instead of focusing so much on the hard or technical skills We're talking about Really soft skills and especially feelings, which is something we can we all have we we could we can push them down But they exist and and I think that the sooner we get in touch with those emotions The better for for for for us individually, but I think especially as leaders It's important to create this type of culture of Vulnerability, I would say That's something that at least works with me and and one way I'm making work is by showing vulnerability first because it's very easy to say well, we all have to be vulnerable. We all have to be these but I you have to show exactly the example that you want to see Yeah, I love that. I mean, I often say that when I compare entrepreneurs and founders That people will follow confidence, but they'll be loyal to vulnerability And if you get real with your team and you're just honest like really honest Including being vulnerable people tend to get loyal to that people respect transparency and they respect honesty It's so hard and also so counter-intuitive in certain cultures at least, uh, you know here in Silicon Valley or in tech in general I grew up with the idea of first of all You have to you cannot be a product manager. You have to be a visionary You don't have to be born with these amazing ideas and it's all about that and then being hard on yourself being hard on others Or not disclosed enough being this constant superhero and I think that it took me a long time to To try to remove some of those mental models and I can only imagine how hard it is for other people If they haven't been exposed to some of the the tools that at least in my case I've been grateful enough to at least see at some point in my life. Yeah You mentioned Buddhism and and I think that's another thing like I I grew up in in Europe in a very Catholic culture or religion, I didn't give that I wasn't I didn't get the chance to choose Anything I was kind of given to me based on Where I was born and one of the incredible things when I moved to the US was to know that There are options. There's access to opportunity. You have to work for it. But at least you know What's in the menu? Yeah, I mean buddhist has been meaningful for me Um, there's so much I've learned from it that I think does relate to my skills as a leader I like the buddhist lessons on suffering that suffering is universal And what can we do to reduce suffering and how can you be present? with With negative change around you and have it not So to keep you down and how can you help other people that have negative things around them? So there's a there's a lot of valuable lessons there So what is next for pol English? Well, um I've created half a dozen companies so far um The two companies i'm working on right now is lola.com, which is business travel and expense management And we're gonna have some news in october So check back And then I also work on a podcast player called moonbeam the website is moonbeam.fm And the problem we're looking at at moonbeam is how do people find your show as a as a podcast host? Uh, what can we do using machine learning? To show get people to better content quickly without making them read through and navigate through lots of menus and lots of content So it's like instant gratification fed by machine learning And how do you split your time between these companies and All the things that you have to do I'm pretty disciplined about my time management. Um, as mentioned, I use google calendar And all my appointments are one of four colors. So purple is lola, which is like my day job and where I spend most My time monday friday nine to five um Yellow is nonprofit i'm on seven nonprofit boards and there's three nonprofits that I started that I Run and spend a lot of time on that Green is self-improvement, which is anything from Going to meditation class to going to the gym to going to doctor's appointment And then blue is everything else sort of friends and family and every monday friday My assistant Eliza and I look at my calendar two weeks out And I make sure there's the right balance between those four things and if I have balance life feels really good and stress free and it sounds crazy Just think of like how many boards i'm on and companies i'm running and nonprofits i'm running and I also teach But somehow I have a life with very little stress And I think the reason I don't have stress in my life is I'm disciplined about my time management and I I make sure that i'm doing enjoyable things every day Even like within lola. I make sure that I'm meeting with designers every day because I love design That is Amazing poll and and I like they are not there the color coding of your calendar I ask this question to a lot of other founders and product leaders And and I agree with you like I also have my different colors and whatever is not on my calendar doesn't exist Yes, it seems like a lot, but I always say that busy people always find time for things that are important to them Yeah, I mean there's a corollary to that which is if you want to get something done Quickly hand it to the busiest person you know because the busiest person you know is the person who can crank their work Yeah But it's been awesome to to learn from you. Thank you so much for your time Great. It's great to meet you. Thanks a lot. I enjoyed it