My guest today is Jessica Ko who is the founder/CEO at Playbook In this episode, we discuss the following: - Jessica Ko Bio - Doing things that make you high - Being a founder/entrepreneur is not for everyone - How to know if you are ready to become a design founder - Why you shouldn't rush to become a design leader - Benefits of starting something when you are older - Pros/Cons of becoming a design founder - Insecurities of being an inexperienced young founder - Why it's easy for a design founder to hire designers - How does a design founder balance spending time between design and other areas - How to level up in areas other than design as a design founder - Managing work/life balance as a design founder - Advice for designers who want to become founders someday For show notes, guest bio, and more, please visit: www.designmba.show
Jessica Ko is the CEO and co-founder of Playbook.com, a visual cloud storage platform for designers. She was a designer for over 10 years at Google and Opendoor, and is now working to make it easier for freelancers and designers to share their assets with the world.
LOOKING FOR A FILE STORAGE SOLUTION MADE FOR CREATIVES?
Create a free account on Playbook and get free 100GB in hosting space - https://www.playbook.com/
CONNECT WITH JESSICA KO
CONNECT WITH ME
Namaste and welcome. I am Jayneil Dalal and you are listening to the design MBA which is a real-life MBA program for designers. You will learn how to launch a side hustle and level up your design careers from the interviews rock star designers.
Jayneil Dalal: Today's amazing guest is Jessica Ko who is the CEO and co-founder of Playbook.com, a visual cloud storage platform for designers. She was a designer for over 10 years at Google and OpenDoor, is now working to make it easy for freelancers and designers to share their assets with the world.
Jessica, welcome to the show. Super excited to have you here.
Jessica Ko: Thanks, Jayneil. So nice to be here, so nice. Thank you so much for inviting me.
Jayneil: Absolutely. Same here. I want to say that you have this amazing very calm vibe. It’s like the more I talk to you, I feel like I’m talking to a therapist like it's so calm and relaxing as if I can get all the answers from just talking to you.
Jessica: Oh! Well, thank you. That is one of the best compliments actually I’ve gotten. That's fantastic.
Jayneil: I’m completely jumping guns on what we're supposed to talk about today but in one of her prior conversations, I told you that this analogy, and I’m going to use it now, I said to you that “Hey, Jessica, you know, I get a high when I connect people. When I make emo interests with people, when I help people in their goals, I get a high as if like if someone has watched like Narcos, it's someone like snorting cocaine and getting high, I feel that kind of high in my body when I just connect people. And you said something along the lines of “You should do things more that you get high of, you get that feeling, meaning that your body loves doing it.” That was one of the most dope advice. And it seems so simple but I don't know it was just so dope advice.
Jessica: Yeah, I mean, it's all biological, right? I mean if you think about it, we're constantly chasing our highs and we get highs from different places because we're just differently wired. Our brains are just so differently wired. So, some people just we have to do startups. We just cannot live because otherwise we just want to like … I don't know, we don't get that kind of high from anywhere else. So, that's the only path for us to be happy. So, then we end up choosing that path. And some people like yourself, like doing podcasts, talking to people, you get highest highs and you just keep doing that, right? I mean, you can't apologize for these things. There's no right path. There's no one path for everyone. It's just we're constantly chasing kind of different highs and I think that's the reason why this world works because we're all doing different things. It's a good thing that we're not wired the same way.
Jayneil: True because otherwise everyone is just going to become a startup founder or something. And I think your advice was so on point because there's also an element of listening to it. Just like I get a high from connecting to people and talking to people, you get a high from running a startup, right?
Jessica: Yeah.
Jayneil: But there's this whole thing about the media and how it glorifies being a startup entrepreneur sometimes the way it's like “Oh, quit your 9-to-5 job” or “Oh, you shouldn't be working for someone else. Work for yourself.” And as a result, I feel a lot of folks who are happy just being designers or just being employees and doing their jobs, they're really awesome and they got too high from it, they somehow feel the pressure to become founders because that's what is glorified.
Jessica: Yeah, that's what makes me really sad actually. We're not meant to do the same thing. And really, it's not being a founder is all great either. We do it because we kind of have to because we're chasing that high, what makes us so … like get up in the morning and be excited about things but it's not for everyone, especially if you have … you're getting highs already from your job. What's the point, right? What if you don't get that same high from running a startup? And the chances are probably … it's a 50-50 chance that you won't get that kind of high from running a startup.
Jayneil: True.
Jessica: I think it's very, very important to sort of sit back and really have to think about what you want to do with your life and that usually … it's not … a lot of people, they hate their job thinking maybe being a founder is a way to escape that. Some people use actually running a business as escape from where they are but that's not … that's just over correcting. It does not necessarily mean that you'll be end up happy doing that. And then people, we make tons of over-corrections left and right but it really takes about you sitting back for six months and evaluating your life. That's when you truly know what you want to do with your life. And sometimes it changes over time because once you've run a company and say “I got my high” but then maybe the second startup isn't giving me that kind of a high that I wanted to get and then I end up switching to another job. So, it constantly changes but as long as you sort of know where you're heading in the next two three years, I feel that's good enough already in this world that's just constantly changing.
Jayneil: So, you've been a designer. You've been a design leader. Walk me through your journey. How did you know from that point that “Hey, I think I’ll get a high from starting Playbook?” like how did that journey happen? How did you know that “This is the thing. I have to do it. I have to become a founder.”
Jessica: Yeah. It's not a simple … I mean, a lot of people ask me that question. It's like “How did you know and when did you know? What are some of the signs?” and you hear about these founders, they were meant to be founders. From when they were a child, they were already selling stuff, lemonade …
Jayneil: I know … selling lemonade stands and all this.
Jessica: I was none of those things. I asked my mom “Did I have any special childhood?” My mom is “No, you were just a normal kid” like “No special, nothing. You were just a normal kid.” So, I don't have any childhood story that's anything special. So, I’m turning basically 40 next month. So, it took a really long time for me to get to it.
Jayneil: If I may say, you don't look 40. And I mean it as a compliment.
Jessica: Thank you. I mean, it’s like I graduated pretty … I think, I also took like a year off and went to Japan and I just kind of did stuff as in I worked there because I wanted to be in Japan and all my 20s, I didn't know what the hell I was supposed to do. I started out as an engineer but I was a mediocre engineer, not a great one. I think, I was actually pretty terrible at my job. Maybe that's why I moved away from it. And then I started doing front-end development and I really loved it. CSS just made sense to me. And then every time you change something it, it changes your web like just the whole canvas. It made sense to me. And then because of that, I became … when things make sense to you, you start kind of doing more of it more of it. So, I became quite good at it. So, I got into google because of that and then I sort of made myself turn myself into UX designer kind of two or three years later after that. So, it's a slow transition of things because I didn't know … I even went to PM school at night because could I become a PM. I didn't know what the hell was supposed to do. And then I became a UX designer, everything sort of made sense to me. Luckily, I had engineering backgrounds, I was kind of sharing the same language with engineers and it was kind of a plus point for designers to do that. This was 2007, 2008, 2009. So, a lot of the sort of UX designers came from engineering backgrounds. So, we all had this kind of shared language. And then I designed … when I was UX designer at Google, I was like “I love this job so much, I would never leave Google.” I remember telling that to my husband, I remember telling that to my parents but this is what happens. It’s life. You do it often enough, you do it for two, three years, you kind of stop learning it, you kind of get bored of it. You want to see what's out there. I think that's what humans are. You're constantly seeking … again, kind of same place that gave me a ton of high, it no longer gave me that kind of same high because I was so excited about absorbing new skills, absorbing what is this … relationships I have to build, engineers, marketers, and PMs and then all of a sudden, now that I’ve done that for what, four or five years, I was no longer getting that same high. So, I start chasing other things and that's how I got into OpenDoor startups. I knew that I wanted to be in startups one day and OpenDoor just happened to be the kind of place. The product, the real estate, it's all … everything, all the interests sort of aligned. And I was super passionate about real estate at the time and I got in and that's when I got like the highest of high, which is … I’m looking over shoulders of … you David Baron. It’s like sales and operations and Ryan Johnson is like operations or the founders, the way that they run business, fundraise. And then there's marketers. We were doing direct mails. We were doing all kinds of stuff. And then as a designer, I got to see all of it because design is needed everywhere, every area. So, it means that I was designing collateral for people, sales and marketing and product, I was building products, working with engineers. So, I was constantly needed in every department, which meant that I got to see what the hell is going on in every single area in the business, which gave me … again, I was getting the kind of highs that I wasn't getting before. And, of course, that happened and then I became the head of design at OpenDoor and the management that's when starting to kind of make sense. And then that's when, again, it gave me that high. It sounds I’m a total addict. I think I am actually. I’m like constantly …
Jayneil: Chasing those highs. Oh my god! But what's so awesome about your journey I’ll tell you is you're constantly seeking different things and seeing where you get that high and you're not afraid to experiment. And when you openly said that “Hey, I’m turning 40 soon,” I felt calming away because … I’m 30 and I’m going to turn 31 in Feb and I feel sometimes I’m old as hell in the sense that when I see all these Twitter posts about 18-year-old founders already starting a company, doing something or someone already found the thing that they wanted to do so early in their life and it makes me wonder “Well, why could I not be the one to hit that high so early in my life rather having to find different, different things?” but now what you said makes sense to me that “Hey, the high that you got 10 years ago or five years ago, it's different from the high you get now.” So, it's always constantly evolving is what I’m learning from your journey and it's okay to explore different things.
Jessica: Oh, yeah. I mean, seriously, so many young designers come to me and they want to know how to get to the field as quickly as possible – “How do I become the head of design? How do I become the management? How do I become like a leader in design industry?” They constantly ask me that. And then I always tell them like “Why do you want to get there so fast?” Because once you get there, it has an expiry date. Usually, it's about three four years. It's no longer giving … it's not going to give you highs and then you end up having to switch to different jobs or doing other things because humans are … if you're anything me, you're constantly chasing highs, then you end up … it no longer gives you that kind of happiness it gives you.
Jayneil: Don't you wish that you were the design founder that you are now but maybe in your early 20s so then you could have wrapped that chapter up in your life much quicker or you're saying that at that point, you just did not have a high for that or any desire to go that route?
Jessica: I think that life has a timing of things. If I didn't become an engineer, I would have never become a UX designer. If I didn't become a UX designer, I would have never become understanding of what management leadership is until later. And then by that time I was say 30s, mid 30s and late 30s, which meant I understand psychology of things, I understand why people do things they do. When you're starting at UX, you're kind of just like “Oh this is … oh you have to do research, you have to do interviews, you have to do prototyping, you have to do all these.” You do those things but you don't understand why you do those things. And only when you're starting to get to 30s, you start to understand why you do those things. And I could answer every single thing … there is process to things. I didn't know that in my 20s, now that I know that, I can actually start to understand, talk to people about it, I can convince people why they did certain things or they don't from a very deeply fundamental … from a fundamental place, not necessarily “Oh because that's what you have to do.” My answer is never “That's what you need to do.” I will tell you why that's needed but I don't think I would have become … startup founders truly … I mean, you're a manager, you're an operator, you're a designer, you're a product manager, you're an engineer. You're all those things. I think that probably the last 15 years or 18 years or something, I was just getting ready to become who I am. And every single step was needed to get to who I am right now.
Jayneil: It's almost a trade-off like in your 20s, yeah, you would have had maybe more energy than you have now, maybe, but the maturity and the knowledge you have now … you have way more productivity, I would say, now being in the role that you are now. So, maybe … comparison wise, the way I look at it is if I could do something that I’m doing now like me interviewing you now, let's say I was doing this 10 years ago, I don't think I would have had the maturity or any of those things that I have now. Maybe I’d have more energy for sure like I could stay up longer, I could go without sleep but probably my productivity and my punctuality were not there at the level that I needed them to be, I might have just missed this interview, I don't know, but now …
Jessica: That’s so true, yeah.
Jayneil: But now, I think I have that maturity which gives me the productivity. So, even if I have less energy than I did 10 years ago, I think I can get more stuff done now, I feel.
Jessica: Oh, it's absolutely true. I think that my 20s, I fucked around a lot. I had so many interests and that I would start something I, would end it after six months because it no longer interests me. I was truly just really purely ADH driven, passion driven but not necessarily I was really thinking, like really understanding why I do think, that’s why I kind of stop and go, stop and go. Now, I pick up something, I tend to go a lot longer and I also manage my emotional really well which means that I don't get burned out that easily, I’m much more resilient than before. I also know that when I pick up certain things and then when I feel down or I don't feel great some days, I know how to pick myself up because I’m in control of my own self and emotions a lot better now than I was in 20s. And then the same is like you … the way that you ask all these questions, it comes from the experience, which meant that you being a designer for that many years, you know exactly what to ask, you also know what your audience want you to talk about. So, all those things, I bet every … that was your 20s basically. That sort of made you …
Jayneil: I had a lot of fuck-ups in my 20s., I’d tell you, for sure. Oh my god! And I absolutely agree with you on that that whatever I start now, I think I am able to continue it much more longer. Before it would just be like I’d start something, forget about it, drop it. The consistency wasn't there. And now what I’m wondering is like you're a designer but now you're a design founder. What are the benefits and downside of being a designer founder than let's say somebody from engineering becoming a founder?
Jessica: Yeah, the funny thing is I’ve heard a VC saying that “Well, designers know how to market but they don't know how to build a product.” I think they probably meant to say brand designers or maybe “Product designers know how to build a product but they can't build a business.” You hear a lot of stuff like that. I actually think it applies to a lot of other fields as well. Sales people, they know how to sell but they don't know how to build product. Marketers, they know how to market but they don't know how to build a product. I mean, you can go on forever, VCs too, I’ve seen people leaving VC world and then become startup founders but they can't build a product again. The point is I think that what these people are trying to say is that it takes a lot to build the business. Operations, Marketing, Sales, Product, everything has to align perfectly but we designers tend to sort of overvalue our skills and undervalue other skills that are required running a business. And then, one of those fuck-ups that I did in my 20s probably, again, overvaluing my skills as a designer and it's probably that. And then now that I’m a little bit older, I understand that there's a reason why all these departments are needed. This is what I’m talking about. I understand why they're needed. And I can tell you if somebody asks me, I have answers for every single question about why we need certain things. That's probably why … I mean, understanding and then appreciating other skills is so much more important than actually whether or not you're a design founder or engineering founder or … if you're any of those things, you're just anything, and as long as you appreciate other’s skills just beyond your own skills, then I think you'll be a great founder.
Jayneil: But there must be some insecurities you have. What I mean by that is as a design founder, you probably don't have any insecurities in the design field because you've done it, you know how to do it but could it be that you might have insecurities in some other domain like marketing or some other field where you haven't worked a long time?
Jessica: Yeah, definitely. I mean, a lot of insecurities usually come from you don't know what you don't know.
Jayneil: True.
Jessica: I think that if I was at Google, I was at Google, I probably maybe … there was like three days out of seven years I was at Google I interacted with a marketer because we're so isolated. We only work with PMs and engineers at the time and the marketing had its own department, sales had its … I didn't even know their sales department. Because it’s such a big company, you don't really understand where people are, what they do. I think that I would have been a horrible founder if I just left Google and then started a company then. Now that I’ve been to OpenDoor and a small startup and all these … I’ve seen HR, I’ve seen what recruiters do, I’ve seen all these things, why a business needs all these roles, I have less insecurity now because I know what I don't know. I think it's because I’ve seen it slightly. So, my insecurity is a little bit better than probably most young people starting out because young people, again, they haven't seen it. That's the problem.
Jayneil: Yeah. And often the young people want to hire the best. So, if let's say a young founder starts a company and they're from engineering, I can see them hiring a good engineer as a head of engineering but let's say they're trying to hire somebody in design or marketing, they want to hire the best head of marketing, the best of everything. And it could be because of the insecurity, I think.
Jessica: Yeah. Imagine if you were a 22-year-old that just graduated and then VCs gave you a whole bunch of money, millions of dollars, and then say “Jayneil, you need to hire head of engineering.”
Jayneil: Oh my god!
Jessica: That means you have to. Like what else … that means you can't argue because … again, you have nothing, you don't have enough knowledge to argue back. It's like “Why do I need the best what?” You can't even ask that question because at that point, you haven't really built enough sort of knowledge to understand what does best engineer even mean, the best head of engineering, do they help with scaling or do they help with the development. What is it? So, that's when the insecurity comes in like “I really don't know what I’m doing.” So, if somebody that supposedly seemed to know that they've seen it all tell you that you need this, then you need this. I’m at a little better spot now because I’ve seen something, I have seen some head of engineering, I have seen some head of marketing, head of design. So, it's a little bit … I can always ask a different question like why … sometimes why, sometimes what do we need or that's probably the next thing that you could try to answer. So, yeah, I kind of feel … I mean, it's hard to be a young founder and people are telling you, especially media as well, it's like … on LinkedIn, you see like a bunch of startup founders “We hire the best this head of this, head of that and head of this” and you always wonder why, what is … and then they always tell you, VCs always tell you “Oh, you got to build the best team.” What does best team mean? It's so abstract. A best team for one company maybe is completely different to other things, right? Because OpenDoor is a very operation driven company which meant that it's completely different than say a Figma building a product team, for example.
Jayneil: And I feel like now you're on the point because of so much experience that, you have you can take all this advice that VCs or anyone is giving you with a grain of salt like, for example, now having done podcasting for more than two years, whenever someone gives me an advice or some articles, they're like “You got to do it this way,” I take it with a grain of salt. I’m like “Listen, I’m not like a podcasting company with 10 employees. I’m like, you know, one-man show.” So, you start to take that advice with a grain of salt “Well, it's not applicable to my level or my scale or something like that.” So, I’m thinking, from your perspective, when you get all this advice from VCs or anyone, having seen what it looks in an OpenDoor and other companies, you're able to filter it down and see “Does it make sense? Is it just generic advice? Is it even applicable to me?”
Jessica: Yes, exactly. Those are probably … and sometimes they're good advice, they're excellent advice too, sometimes, but I have to know that from within. It's not because somebody told me to do it but I know why that's important advice to me. I can see why that person would recommend I need to hire this type of skills … people with this type of skill sets because I could see what this person would do when they come into our … you know, not this abstract form of like “Oh, this head of marketing comes and then suddenly it's going to get so much better.” It's not that. It's like “Oh, I am so missing these skills and I’m not really enjoying these things … doing these things myself. So, it’ll be so amazing if this person comes and then on day zero will just like start doing it.” That is a very … it comes from within. And, again, it comes from the experience within … because of the experience, because of all the stuff that I’ve seen in the past. And not to say that I’m like this. I don't take any … and I’m taking advice from people. I love advice, I really do. I actually think it's … but the grain of salt thing, it's totally … I love hearing what I don't know and then somebody giving me different perspectives. And then I try to apply that to my business and then where my needs are there. So, it's almost like merging it like where this kind of intersect is where the really amazing stuff happens.
Jayneil: Absolutely. And I think there's something about being able to … like you said, someone gives you advice and if you have experience, that advice resonates with you. And I would rather be in that boat versus being the place where I don't know anything and I’m just taking advice because I don't know any better, right? So, I think that … because recently I was talking to a founder and they were having a hard time hiring a lead designer. So, I’m assuming or I’m guessing that you of all people definitely don't have a hard time hiring a designer on your team.
Jessica:No. The one good thing about being a design founder is you attract the likes. So, likes attract. I think that's what humans are just like when you see … leadership, for example, has the same kind of background as you have or the kind of skill sets that you value, it's more likely you want to work for that company. And it goes both ways. Sometimes I appreciate people that come from possibly … I mean, it's unconscious. It's a very unconscious thing trying to consciously kind of understand why I’m attracted to certain backgrounds. And it's all based on this like I find comfort in people because sometimes we have fear around things that we don't know. So, when you understand certain things, you're much more attracted to it, you're much more understanding. It’s just like VCs like to invest in places where they know the best, sometimes.
Jayneil: Oh yes!
Jessica: Because they understand. It's a comfort thing. It's stability and comfort. And we find a certain kind of level of comfort in places that we know. So, that's why design founders tend to attract other designers. That's why recruiting designer is not very hard. Same thing goes for engineering founders. They tend to attract really good engineering talent because people want to work for that amazing engineering sort of leadership.
Jayneil: But then speaking of comfort, you are very comfortable in the design space but as a founder CEO, you have so many departments to oversee like Marketing, Engineering, Sales. How do you make sure that you don't just spend time in your comfort zone like just spend all day on the design and talk to designers? How do you make sure that you're also spending enough amount of time in this other fields where you may not be as comfortable as you're in design?
Jessica: I mean, the short answer is it's hard. It's really hard. It's almost like exercising. It’s like you're so used to doing a certain exercise move and your muscles have been so good at that, gotten to point where it’s become so good at it, you want to keep doing it because it makes you feel good. That's probably also that my work OCD have developed naturally. It means, I see pixels and it bothers me. Yet the pixels don't actually make your company successful or even bricks … nobody cares about pixels, yet only you care about those kinds of details. And then we've developed those work OCDs over many, many years but to ignore that completely, it's incredibly hard. It's almost like a conscious effort to ignore pixels.
Jayneil: It is because if a recruiter on your team or someone sent you something that was visually misaligned or something, you know there was a visual misalignment on the offer letter and you're like “It doesn't even matter. Let's get the offer letter out and secure the candidate” but then a part of your brain could be “Oh, we got to get that alignment right.” So, it's hard, I guess.
Jessica: Right, exactly. So, that is a conscious effort that you're making, “It doesn't even matter. So, why don't we just get this offer letter out?” but when you go to sleep at night, it bothers you still. So, that's right.
Jayneil: So, what do you do?
Jessica: You really have to ignore that voice in your head.
Jayneil: Oh my god!
Jessica: Because it really does not matter. So, there's probably 50% of pixel stuff misalignment I’m actively constantly trying to ignore but it is incredibly hard. That's probably the downside of being a design founder myself is that the work OCDs that come from being a designer for so long … and you become super hands-on. Especially on the days where you feel stressed, that's your comfort zone. So, you kind of get in and start fixing those pixels yourself.
Jayneil: Oh my god!
Jessica: Because as soon as you do that, you're like “Ah!” That's just kind of … your brains are happy.
Jayneil: But there should be some benefit to being a design founder, right? Because when people give examples of the Airbnb founders or Apple like “Oh, their founders were very much focused on design. So, that's why the company and the products are beautiful.” So, if a design founder has to consciously block away just like not fixing the pickles every time because, you're right, it's not always instrumental to success, but then wouldn't it not reflect in the beautiful products and services you're designing if you don't have to block it away?
Jessica: Yeah, I would say … I mean, the likelihood of your product being more beautiful than others will be true anyway because you're just naturally … so, you have to block up that part a little bit so that other parts of the muscles in your business are growing. So, it's not like you're over exercising one arm and then ignore the rest of your body. You kind of have to train … even though it will make you so uncomfortable for the first six months of exercising other parts of your muscles, you have to do it and not just do … you still do one arm exercise because it makes you happy but you have to make very conscious effort to actually grow all parts of your muscles and your bodies or your business muscles. That's what it meant.
Jayneil: It's almost like you're already at an A+ level in the design field. So, now you have to consciously be like … or let's say you're at A-level. You're like “There's no point in me becoming A, A+ and design more. I need to at least get to a B+ in marketing, engineering, sales just so that I can talk to all these people that I’m hiring, I can make sure I make good hires, I can communicate with them, I know what questions I need to ask them.”
Jessica: Yes, that's exactly what it is. It's like until you get to a certain level, it's almost like … all these amazing design candidates approach me and say “Can I work for your company?” because, again, likes attract. You have to kind of ignore that because as soon as you hire one more amazing hire, your right arm is going to be huge and the rest of your business muscles are going to die. Unless that is actually the strategic hire, you understand why you want to make that hire, it can't be … it's not because you're just comfortable making that hire and you appreciate that hot skills. You have to really look into the rest of the business to make sure it grows healthy at almost like the same pace as the others.
Jayneil: But how do you do that. For example, if it's a design field, I mean, you speak the language exactly what to ask, “Hey what tools do you use? How do you organize your design system?”, there's all these questions that you know what to ask in a good hire, you know how to communicate with them, you know how to check the health of the design organization in your company because you've been there but let's take any other field like engineering, marketing, sales. How do you level up as a founder like “Hey, these are the questions I’ve supposed to be asking and these are the things I should know about. These are the terms I should learn about.” What is that up-levelling or scaling? What does that process look for you?
Jessica: Oh, that's a great question because I think about that all the time, too, how do I level up as a founder.
Jayneil: Oh my god!
Jessica: It makes me think about in my 20s, did I ever ask my question about how do I level up as a designer. I guess we read books at the time but it's really just doing that makes us great designer, right? It's not so much of us learning from books or going to conferences. I don't think I barely pay attention to conferences anyway. Looking back …
Jayneil: I don't even know if you have the time. I know a lot of founders go to conferences. With your busy schedule, I don't even know if you have time to be just going to multiple conferences a month.
Jessica: Yes. I can't … especially when you read books, usually I forget a lot of that stuff in two months. So, I have to keep reading it multiple times. My brain doesn't retain those kinds of information that long.
Jayneil: It makes you feel good though at the moment like “I read this book and I could spout wisdom from it.”
Jessica: Right. No, I can't. I really can't. I think I really … the only way I became anything decently okay designer is just doing like I spend that many hours designing. Some days I would … especially when you're working on something you're passionate about, you tend to work through the night and just trying to solve that problem. So, it really just is exercise you're just constantly using the muscles to really level up that part. So, as a founder, I truly believe that you just have to do. If you don't feel comfortable doing certain things, for example, like a lot of people get very insecure about sales and marketing, especially if you're a design founder, so people say “Well, you must really not be very good at sales and marketing because you're just a designer, you know.” I hear that a lot also from … when I became a founder … but really just how do I learn sales and marketing? I just do. I go and talk to people. I go and try to sell. I try to, you know … I learn from one experience and I apply it to the next experience. You go fundraise. You don't hire finance person to go fundraise for you. You do everything. So, whenever you start to kind of … anxiety builds up in your body is like “I can't. I can't do it. I can't do it,” I just try to block that anxiety and just go do.
Jayneil: Oh my god! So, you tried to sell your own product which is how you got to learn about the challenges that if you hired a head of sales, they would face the same challenges when they're trying to sell Playbook but sales is still like you can go and talk to people and do it but let's take another example like engineering. As a founder, you're not going to certainly start coding everything to learn about it, right? Because, I mean, I do get by doing, that's the best way to learn but you can't just suddenly start coding the entire database if you've never done it before and start learning a language on which your entire product depends on. So, what happens in that case?
Jessica: Yeah, that's a great question. I think that … I mean, you don't know what you don't know until you actually try. I mean, that's for sure, right? So, engineering is highly technical and it takes years to be a great engineer and to be able to do all those stuff but there are certain things like you can learn, for example, and you have to try to learn these things. For example, when you go out and meet all these engineers and they're going to bring up some technical issues with your product, the way you're envisioning your product, they're going to raise up all these issues just like when somebody tells me like “Oh, we're going to build a rental home website where people would do all this,” when a designer hears that, we go through UI immediately and within like a minute, we have gone through the flow probably.
Jayneil: 100%
Jessica: Right. You need this. You need that. You need … how are you going to build this? I don't know. I don't know. You probably need some internal tools that will help with that but that would mean you need this UI. And immediately, because we have trained that muscle, that part of our brain so much that it doesn't take a lot for us to ask those questions because that's kind of how we approach problems for the longest time. Engineers, they do same thing. They will ask very interesting questions if you don't go and talk to them. You bring up that product vision. So, then you pick up all these constant data, you pick up all these engineering data and you ask … and you basically develop certain things sort of knowledge around the prior conversation with other engineers and you take it to the next engineers and then you have a conversation again. You keep levelling up that kind of content and eventually you'll realize you're starting to understand how they think through that problem and what kind of engineering skills you need. And then if we did everything right in the engineering side, these are the kind of outcomes we will have. And it's possible, not possible, you can actually start to answer a lot of those questions but not necessarily coding because that would mean like … but you wouldn't know by then, you wouldn’t know exactly what types of engineers you’d end up wanting to hire.
Jayneil: You're right. I’m in a room where my noise is echoey. I think you can hear that maybe a little bit. Now, how, when this episode goes live, my podcast producer makes that sound awesome, I don't know what filter they're using like I don't know. If you ask me how that filter was designed, I don't know. I know enough that “Hey, there needs to be some post-processing work. That's how it's going to be done” but, obviously, I don't know at the depth level of how that operation is done but I just know what the good outcome looks like.
Jessica: Yes, exactly. That's exactly what it is but really what sells podcasts is truly the content.Yes, the …
Jayneil: Yes!
Jessica: Right? Content is important. So, you start focusing on the things that matter the most. You yourself as a founder, you focus on what's most important for business and then the video quality and stuff, you get to a point where it's good enough and you start leveling up constantly as your podcast become more and more and more popular, it reaches a larger audience. So, you almost level up every part of your business. Yet you retain what is the most important of that business is constantly you yourself have to care about the most because that's what founders are supposed to do.
Jayneil: Yeah. And you're so right. Starting this endeavor, I focused on so many things that did not matter. The biggest thing that most podcasters the start out now, the biggest thing they kind of over focus on is growth, distribution and they compare to other podcasters that started in 2000s and have millions of followers and stuff and it's not the right metric to compare to and they kind of obsess about growing a Twitter following, not realizing that what really is going to make or break a podcast is the consistency.
Jessica: Yes.
Jayneil: If you can't like keep a podcast going for … like the content, engaging content, good guests and keep it going, consistency number one, and you get it going for like three four five years, then you can think about “I need to hire some sales. I need to …” They start focusing on day one about “How do I make money from a podcast?” it's extremely hard to make money from a podcast these days, extremely hard, unless you're one of the rare few ones who has a massive distribution and already famous or popular. So, you're right. I focused on so many wrong things, I over engineered on the audio and thinking that “Oh my god, this is like some Netflix production house” and I realized “It's okay. I just sneezed. It's okay. I don't have to have the best mic and all these things.” And there are so many like wrong metrics I focused on that I shouldn't have but I learned, I learned and I course corrected, just like you said.
Jessica: Yeah. I mean, imagine that young founders have to face that. All these medias or VCs telling them “You need to be perfect at this and this and this. How are you going to do the social media? How are you going to increase your Twitter followers?” like it really matters. Those kinds of stuff don't matter but yet we tend to … it's where the anxiety comes in, you feel like you're not doing enough but really what's important is that you have to know what you need to do with your product and then you focus on that and the rest of it is you either try to delegate as much as possible and you level up slowly according to sort of your business growth but not necessarily try to do perfect everything because nobody can do everything perfectly. There's just no way.
Jayneil: It is. You're absolutely right. For me, it was filtering out the noise which was, in my case, just growth and distribution and stuff because I was like “If I just do this stuff right, it will come slowly. It'll just take time.” And for me, obviously, the goal is different. I’m trying to build connections through the podcast. So, trying to be the number one podcast on Apple Store is not necessarily my goal. So, obviously, every product or startup will have a different goal. And what I’m thinking about now is because I love doing this so much, I can obviously spend so many hours on it that could affect some other areas of my life like it could affect my day job, it could … like I want to be there on weekends with my friends too. There are some things going on in their life. I want to be there too. So, as a founder, it's very easy, I guess, for you to just spend days, nights, weekends obsessing about the company, every small thing because you love it but then how do you have that kind of balance where you're there for friends, family, and other things in your life too?
Jessica: Yeah, I always wonder who gave people idea that you have to work through weekends and nights to run a successful startup. Who told people that? Sometimes … is it totally necessary?
Jayneil: I think the large part is Gary Vee and then the people call the Hustle Porn, that's the word for it. It's just like “You got to …” there's posters like “You got to grind till you fall down” or “grind till it bleeds,” whatever the motto like “You ain't hustling, bro? You ain't doing shit.” And it's just … it's this thing where you have to appear to be busy, right? Regardless of whether you're getting outcome or not, doesn't matter. You just got to be just like grinding, hustling like “yah! Yah!”
Jessica: I think that it is probably part of my rebellious nature is that I don't believe that you have to be hustling to be successful at your life or your business or startups. Yes, I do think about my startup all the time but not necessarily I’m executing all the time because usually the best ideas usually come when I’m on the plane to somewhere. I can't do anything. There's no internet. So, the internet is down on the plane and I’m just sitting there like just sitting there, just staring at the ceiling or a window. That's usually 10X ideas come about. You just have to kind of empty it out once in a while to get good ideas but that means you have to be thinking about the problem first leading up to that until you have a solution but the execution part … and then it makes me wonder all that Twitter following … trying to increase the Twitter followers or Instagram followers, try to do this and this. Yes, then you will have to be really hustling but, in my mind, are those really that necessary?
Jayneil: Yeah, because, I mean, you could be a design founder and just post all this advice on Twitter every day just and you would probably get a lot of following but … Yeah, I’m kind of thinking about it too like what benefit is it going to give you from actually then compared to doing the work and growing the company.
Jessica: Exactly. Sometimes we do a lot of stupid work because we have to be busy and that makes us feel good about it. Sometimes we do it because of our anxiety because when we're doing stuff and being productive, it makes us feel good and then not think about … not being super anxious about things but is that really truly actually …
Jayneil: What you should be doing …
Jessica: Yes.
Jayneil: Oh my god! I think you should start some kind of like founder therapy forum for designers or people in general and help them really reevaluate a lot of things. I mean, I had to go through my own set of similar pathways to realize these things. And I’m kind of curious though, for designers who are listening to this and they want to be like you, they just want to be like “Oh, I want to be a designer founder. I want to start my own company. I want to do a startup,” what advice would you give them like what things should they think about, what are some things they should be mindful of?
Jessica: I think we started the podcast with this … it was … there's no right or wrong answer to anything in life. Really the bad shit happens when you're FOMO’ing, when you see other people doing stuff. When you hear about people making crazy money on NFTs, you feel like you have to …
Jayneil: I know I’m one of them. Yes, guilty of just going to that FOMO.
Jessica: It's really … can you imagine like … in a way, I’m lucky that I didn't live in this crazy internet social media life. My 20s were somewhat quiet. Yes, I had FOMOs.
Jayneil: Me too a little bit like I grew up in India. So, I’m not on Insta or snapchat, for that matter, because we didn't have a phone for the longest time in India. It was like a while before we got phones. So, I grew up in that old school. I’m the odd one out when I’m hanging out with people in their 20s and they're exchanging numbers and they're following each other on Insta, that's what they're doing and they're like “Bro, what's your Insta?” and I’m like “Can we just exchange a phone number?” So, they look at me as if like what century am I from. I really get that look.
Jessica: Wasn't it nice? I’m a lot older. So, my FOMO was between me and my classmates, not like the entire world … the entire world or Forbes 20 Under 20. I’m not comparing myself to those people, never in my life. So, I feel incredibly sad for the people who are actually comparing themselves to other people that are happening on social media making millions of dollars on NFTs or doing some crazy things that they … all those stuff, the offers they got. I just feel FOMO is what kills you, sadly, but it is hard to turn that off. So, the only way you can really just try to survive, to try to avoid it as much as you can is to turn things off but that I know that's really hard. Really there's no right or wrong answer. I’d say you only get to have one life.
Jayneil: Yes!
Jessica: I mean, really think of it as “Where is my brain the happiest? Is it just in the current job right now where I have all my co-workers and my friends and we're having a great time all the time, I really enjoy coming to work?” Then that is … you get a high from that. So, what is the point of trying to FOMO in places.
Jayneil: But there's money aspect as well. You could get a high … I mean, let's say you get a high from knitting. I mean, let's say I get a high from knitting … I’m just making things up … but that doesn't necessarily pay my bills. You see what I’m saying. The chances of me becoming the knitting expert in the world, I don't know, or making so much money from it, it's really rare. Don't get me wrong. I would assume that I get paid more right now as a designer than I would if I just started to pursue knitting. So, there's that balance too like you have designers who make really good money and are good at their job but then they also want to become founders. Now, even if they get a high, let's say that, the economics of that are also very difficult. The fact that they will get funded, would they get a funding to continue that idea. Maybe they have a family, I don't know. so, what about that income stability? So, I don't know, there's all these other things as well to consider.
Jessica: Yeah, of course. I mean, I make basically one-tenth of what I would make if I were working at a corporate job right now.
Jayneil: As a design leader, yeah.
Jessica: So, a design founder. So, founders don't make any money for the very longest time. The payoff is … it can be large at the end but it also can be nothing but the question is whether or not you still get high even though you make … just like yourself, you're making podcasts. Yet you get so … you get high even though you make no money.
Jayneil: Yes, I don't make any money now.
Jessica: That's a true honest answer to where you get your high. It's like even if you get nothing from it, I still enjoy doing it. I still learn a ton. My brain is so happy when I’m done this. That's when you know truly like you …
Jayneil: But then I also have a stable day job that lets me do these things without having to worry about monetization from the podcast. So, that's just one caveat. So, I wonder, in your case … and you don’t have the answer this, by the way. I’m just kind of curious … is the fact that you worked a lot before and you worked for decent amount of years in corporate America, did it help that you had maybe some savings or something from that like you'd been around and you knew that “Okay, I have savings where I can always go back to that” or do you feel much more comfortable now that you make much less than you would if you were still working at a corporation?
Jessica: Oh, that's a great question. I mean, right now … okay, when I left Google to join the startup, that basically … it wasn't even called OpenDoor at the time. It was just … I think it was called Home Run. It was only like six people. There was … I always had this mind because my parents were like “What are you doing leaving Google job? What are you doing to go to this startup that makes … you're basically making one-third of what you were making before?” I always thought of it as going to MBA. When you go to MBA, you have to actually pay 200,000 dollars for tuition. I’m going to MBA. I’m getting paid. I’m getting paid to learn all these things about startups. So, I’m like “Oh, how lucky am I to get paid while I’m learning all these startup operations.” I think there's some VC that said this, something about either you should be earning or you should be learning or something. Otherwise, you should quit your job. I think that I put a lot of emphasis on learning part. Even if I don't take on any money, I just want to … that's when my brain is happiest. I just want to learn everything about the world, everything. So, that's … if I feel like I stopped learning, I feel that's when I start to become like “What else can I do? What else can I do?” And I always kind of tell myself “Well, okay, I’m going to MBA except I’m getting paid to do it.” So, you can actually … a lot of it is self-rationalization. You just kind of have to just tell yourself that your goal in the next two, three years is to do this. You kind of time box a little bit, say “I want to be a founder because I really want to learn what it's like to run a business.” So, it's almost like … I think of that as just going to MBA. Really, it's like you don't have to really worry about your … you don't have to constantly worry about opportunity costs. You don't have to do all these things. You just do and then you know. Eventually, you'll go back and find a job again if all things failed.
Jayneil: Yeah. This is very similar like this podcast is my version of not paying 200,000 dollars and getting an MBA which is talking to amazing folks like you and getting that wisdom. That's literally what I’m doing here on a Saturday afternoon. My buddies would be “What on earth are you doing on a Saturday afternoon in this abandoned … well, not abandoned but just empty co-working space?”
Jessica: You're right. Your brain is happiest when it does this, right?
Jayneil: 100%. And then how can designers who are considering on kind of the fence about whether they should become founders or not that they want advice from you, how can they contact you or get in touch with you?
Jessica: Oh, send me a message on LinkedIn. I usually am pretty good with LinkedIn messages. You can also email me, Jessica$Playbook.com. Those two are the best way to reach me. I check my email a hundred times a day.
Jayneil: Gotcha! Thank you so much, Jessica, for coming on the show and sharing your wisdom.
Jessica: Yeah, this was fun. It really truly was like really … this is probably my … this is my second podcast but yeah, this was fun, really fun.
If you made it this far, you are what I call a design MBA superfan. And I’ve got a gift for you, my superfan. Head over to designMBA.show where you will find my email address. Email me one thing you learned from this podcast episode and I will get on a 30-minute call with you and help you in your career goals.
See you in the next episode.