jake kahana

Jake Kahana: Inventing caveday.org and Teaching at the School of Life (#255)

Our Guest Today: Jake Kahana

Jake Kahana is cofounder of Caveday, a company founded to maximize productivity for individuals and corporations through facilitated deep focus sessions and deep work training. Their global community has participated in over 10,000 hours of deep work “in The Cave.” As a founding US faculty member with The School of Life, Jake teaches workshops in emotional intelligence for corporate teams.

He speaks at conferences and companies around the world. He’s proud to have his work as part of the permanent collection at MoMA and his parents’ fridge since 1989.

Currently, Jake is working on The Creative Department (thecreativedept.org), a management training curriculum for creative leaders.

Watch Our Interview


Jake Kahana Inventing caveday.org and Teaching at the School of Life.m4a – Powered by Happy Scribe

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Everything you need to make a podcast in one place, download a free Anchor app or go to Anchor.fm to get started. Now back to the show. Feisworld podcast helps independent creators live their creative and financial freedom. I’m your host, Fei Wu, and I’ll be taking you through a series of interviews with creators from around the world who are living life on their own terms. Each episode is packed with tactics, nuggets you can implement origin stories to make listening productive and enjoyable.

We’re not only focused on the more aspirational stories, but relatable ones as well. We also have none interview based miniseries releasing throughout the year to help Deep dove into topics such as freelancing, marketing, even Indie filmmaking that would benefit creators like you. Show notes, links and ways to connect with the guests are available on Feisworld.com. Now onto the show. Hi there, this is Fei from Feisworld, thank you so much for listening and welcome to another episode of the Feisworld podcast, Livestream.

Why do I see Livestream? Because I have been live streaming all of these conversations directly on my social media channel under Feisworld. So that is F-e-i-s-w-o-r-l-d. To be honest, I so regret not doing this much, much sooner because live streaming or multicasting are not brand new technologies since the pandemic. In fact, they have been around for a long time. So, you know, originally first they became very popular on Facebook and everybody started broadcasting whatever they’re doing.

And then Twitter caught up and there’s now Instagram live. A lot of people use Instagram for interviews, which I find really fascinating. And what I have been doing is called Multi streaming. And I use the service called Restream audio, which I love. And it’s so simple it doesn’t require you to be highly technical. And how it works is I will hook it up to Zoom and through Zoom I will basically just Livestream, I connect whatever your stream key website I need to connect and off I go.

And it’s super exciting because I love this idea of raw, uncut, really authentic content production process. Previously, for years and years, my producer Herman and I would spend weeks to edit an episode and that took so much effort. And there’s music and and there’s leveling all that. Of course, something that was instructed by me. I wanted this end product to be so polished, but then later on realized that when I go live, not only different social media platforms who actually favor life videos, but I actually also got to interact with people live.

So if you’re interested in experiencing that and then we have a lot of really interesting guests coming up, then definitely follow me at Feisworld on Facebook, Twitter or my new YouTube channel under Fei Wu, my full name, and I have to see you there. So who is going to join us today? You mean wondering? So I would like to introduce you to my guest today, whose name is Jake Kahana. And Jake is the inventor and co-creator behind the CaveDay.org.

That’s right. You heard her right, Caveday.org. And he’s also a teacher at the School of Life, a YouTube channel, an organization based in England that I absolutely love. In this episode, I talked to Jake really about his entrepreneurial process, about his origin story. I met Jake through Seth Godin’s ALTMBA, and he is certainly not the only one because we have interviewed so many people from all ALTMBA whose stories have resonated with so many of you guys, you listeners, you know, with Jake as a new friendship as a result of cave day.

By the way, if you don’t know what it is, Caveday is a phenomenon. Jake and his cocreator basically invented this idea of virtual workplace. And I know virtual workplace is not brand new, but the way they do it is really fascinating. So each and every day, which you can see a schedule on cave data or a group of people, by the way, that’s not 15 or 20. I joined a session was up to nearly 100 people at 9:00 in the morning.

So the sessions could run anywhere between 60 minutes to two hours, you know, one hundred and twenty minutes where you start the session with everyone doing a session, you actually go through a yoga workout, some basic stretches. You start and pause what we called sprints with people within your group. So what it means is everything is timed around 45 minutes. And so you do have to get up and stretch and then you refocus on whatever you’re doing. What I also love about the process is they actually introduce a lot of these best practices to you and will teach you how to be more productive and effective with your work.

And once you join the session, first you say hi and kind of meet and greet everyone in the group. And it’s just really lovely for me, even though it’s not something that I do day in and day out. But a lot of people do become subscribers and this is part of their daily routine, part of their weekly work life. So definitely check it out. I also had the chance to talk to Jake about his experience working at the School of Life.

He even told us how he was selected to be an instructor in the United States, in New York in particular. And that interview process was something that he really thrived because Jake also worked as a professor and he’s a teaching professor focusing on design. And that really gave him a the leverage to win over the competition. So thank you so much for listening. Know that I really appreciate you here as I’m recording. This is kind of late at night as a content creator, especially as a podcast or going through these materials and working late into the evening.

This part is so important, and I absolutely love to be able to connect with you guys, so I will see you at the end of the episode and next week, I’ll be right back for another episode of the Feisworld podcast. So much love to this community. And without further ado, please welcome Jake Kahana to the Feisworld podcast. Hi, everyone.

This is Fei Wu, again, from Feisworld Media, you’re probably sick of me if you’re watching this from my personal profile, but I’m with someone who is absolutely not boring at all. I am super impressed to bring in Jake Kahana, I’d even ask how to say your last name. That’s correct.

That’s right. You got it.

Awesome. Well, Jake and I met during Seth Godin’s ALTMBA, so we’re actually the same cohort together right then and there. I knew that Jake was going to you’re talking about different projects, but we all were. And how many of those really become real things? But you are certainly did. And a quick intro. Jake is a designer entrepreneur who teaches creative leaders the tools and skills to build a thriving creative teams. He is the founder, co-founder of Cave Day, a company founded to maximize productivity for individual and corporations through facilitated deep focus sessions.

I participated in one and we’re certainly going to go over that experience. That is so fascinating. Another interest of mine is that Jake is a founding US faculty member with the School of Life, which is by Aland the Puton. I’ve been following his work for a long time, interested in all things related to emotional intelligence. Last but not least, Jake, I’ll make sure all four straight to talk about his permanent collection that MOMA and that that’s it.

Welcome, Jake.

Yeah, thanks for having me.

All right, so so there’s a lot of things that you do like how could you tell us a bit about maybe your origin story just in case my audience is not as familiar with your work. You’re a designer entrepreneur. How did that come about?

Sure. I went to school. I went to college trying to get into the animation industry. I was like, I’m going to go work at Pixar. I went to school out in L.A. and when my first semester, I said, animation is not for me. I’m going way back. But when not, why wasn’t it for you?

You know, I was like, I love Pixar and movies and filmmaking. And I just found animation to be really tedious. It was really slow. I think my first semester, one of my assignments was to make a two minute hand drawn animation and I drew like twelve hundred drawings of a man walking. It was like not how I wanted to spend all my time. I appreciated the character development and the design and the writing and the storytelling. I appreciate animation.

But really what that did is it sort of set the tone for my whole career because through college I said I’m not sure what I want to do. Let me take an acting class and a songwriting class and let me take some different kinds of art classes and web design classes and that kind of broad background. An exploration led me into what I sort of do all the time, which is I get really involved in something and I learn a lot. But basically what happened is that broad background and learning led me into a career in advertising.

I was an art director at some different agencies for eight or nine years and took some time off. I got really burnt out, as people do in creative field right now. And so I took a year off and I decided to learn how to code and work with some tech start ups, actually moved to Tel Aviv and lived in Israel for six months, learning how to code move to San Francisco for two months. It was just sort of all over the place.

I fell in love with, like digital product design and startup culture. And I’ve sort of gotten a little cynical about startup culture and the growth mindset and all that. We can talk about that later. But yeah, I sort of have this background of advertising and storytelling and design and this within the last six or seven years, this fascination with side projects and startup culture and building different companies. So, yeah, I’m sure we’ll talk about all of the things you mentioned.

My design work, my project came to a project, turned it into a company and the teaching that I do at the School of Life and with my own brand.

Yeah. Wow. OK, I’m going to I have a lot of questions and I know that we have so much to cover. But I would like to hear about your experience. And in Israel, I mean, you not only did a lot of things and by the way, I also spent about a decade in business tech consulting as well as advertising. And that’s why Margo and Erin, Margo, Erin, Margo and Erin start Margaret Erin appeared on Faizal podcast and we like we hit it off so well and so kind of making fun of the culture a little bit.

But you’ve lived through it. And what was it, I guess what was it like for you? What was that that moment you said, oh, I’m going to it. Were you scared to try to do something else? Were you pretty comfortable for the most part to do something on your own?

There’s a lot of questions in there. I think I know what ended up happening for me, it’s it’s definitely a scary thing to go into a new industry and to pick up your life. I was living in L.A. for 10 years. And I think for me, what ended up happening is a couple of things were going poorly in terms of my rent was going up in a couple of months. And I said, oh, that’s that’s kind of a sour thing.

I love my apartment. But is it worth at the time it was like fifteen hundred dollars for this place in Venice Beach. Like to walk on the beach. That’s a lot of money. And now I’m sure it’s more so. My rent was going up, I was freelancing and a job just fell through. And I think I broke up with somebody. I had a really short relationship and it broke up and I was sort of like all of these things are sort of happening.

I think now is a good time to sort of pick up and go. And so I did some research and I found an organization that helped people set up with an internship in an apartment in Tel Aviv. And that’s really all I needed. So I wasn’t interested in sort of getting a big job. I just sort of wanted some new learning and learning how to code and working in the tech industry, in the startup community out there. So I’ll I’ll say right now, it was very scary.

I packed up my whole life. I put it into storage and I moved across the world. And I think that that was something that felt like a necessary part of what I wanted out of my my twenties. I did it when I was twenty seven, twenty eight. And I just was like, if I don’t go live abroad now, if I don’t go try something new, then I feel like I’m sort of locked into what I’m doing for the next 20, 30, 40 years.

And so that to me felt even scarier to do the same thing of something that I didn’t really like then to take a little bit of a leap and take six months to to move to Israel. And sort of on a personal note, I ended up meeting my wife in Israel. She was living in New York, did the same thing, got burnt out at her job, took six months to work at a startup in Tel Aviv. She lived down the hall from me and.

Now we have a child together.

Wow, that’s incredible, both of you are from the US and actually met in Israel and sort of on a same trajectory and same wavelength. Wow, that’s really incredible. I feel like I definitely heard those stories before from my other friends who come from the same place. But I actually met somewhere else with that same vision and with one of the reasons why I mention kind of that transition and into going to Israel, I suppose, where I assume that you didn’t really know a lot of people there.

Did you have family who lived in Israel or anything?

I did. My my father is Israeli. His two brothers and two sisters are there. But the purpose is not to stay with them. The purpose was to have a bit of a life on my own. So I feel like I did that. I definitely had the help in terms of like every couple of weeks they would reach out. I would go have dinner at their house. So they meet me for coffee and I had that support system, but generally, like, made my own new friends.

I had my own apartment, went grocery shopping and, you know, furniture shopping and navigating a new country and new language. All of that was was a part of that.

How did you how much Hebrew did you speak or do you speak now?

I actually speak a lot at the time. I could probably, like, ask your name, ask know what kind of work you do and not even really understand the answer. But I it was something that was really important to me and continues to be important in terms of like, I guess I’m on this kick right now of learning things and doing habits that don’t necessarily have an end goal, that are just like I’m interested in getting better at something without saying once I do this, I’m done.

It’s like I think this is part of a lifelong practice. The same with, like stretching and exercise and reading every day. I’m not trying to read fifty bucks a year. I’m just trying to get in the habit of reading every day. And the same thing with Hebrew. I think the idea of like practicing three to five times a week, doing some flashcards, five times a week, ten minutes a day, is building this habit that is really becoming a meaningful part of my life right now.

I think that’s actually why a lot of people like your brand and like the things that you create, because I think your belief system is inherently there. That’s not a surprise. But I definitely notice with a number of projects I got to know through you that you created is that you’re really you’re really in it for the long game. I know that’s kind of why we lost that Goans work so much. It’s not about a destination. It’s not a quick fix.

You get paid fast scheme sort of thing, which we see so much of. You know, I’m curious like how people say that it’s hard to sometimes transfer or translate your prior skill set to something new that you’re creating. So I know it’s a little bit of a sharp pivot, but I would love to kind of hear your thoughts on Cave Day. Tell us what what is it and why did you feel the need or the drive to create something like that?

So cave day is facilitated deep focus sessions that are held on Zoom in a session that we called the cave, so a short pitch might be think about it like soul cycle for work. You come to a space, you have a guide who is going to sort of push you kick your ass a little bit more than you could on your own. You’re surrounded by a group of people that are working alongside of you. We’re all on our own journey, but we’re all doing it together.

But you show up doing your own work and you could go get a bike or get on a bike and push yourself. But having the group, having the leader makes you work harder, makes you focus more and keeps you accountable to the work you’re going to do. So it’s sort of a hard thing to understand that people join us on Zoom to do their work. But it’s not just coworking. We take breaks together. We start together. We end together.

We we check in at the beginning, what are you working on? And we check out what did you get accomplished at the end. So all of these elements are part of the methodology that we’re building. And it started actually I launched it during the NBA in January of twenty seventeen. I did that. Wow. Yeah. With two Cofan, our first event was January 17th, twenty seventeen. And I started with two co-founders and a lot of where it came from was this ethos of sort of two things.

One, we know a lot of people that are working on important projects. I had side projects. You’re writing a book, you’re starting a podcast. My friend is wanting to launch a business, wants to write a screenplay. We have all these people with really interesting projects. And so that’s part one. And part two is when we sit down and we do them in intense sessions. If we just took a Sunday to just work on your screen player, map out your business like it’s really draining.

At the end of the day, it’s so much work, it takes so much out of us. And our belief was that we can create a methodology and a community around doing work and staying energized. So there’s been a lot of tweaks. We started in person. Now we’re entirely remotely we started at full days once a month, and now we run five times a day. So things are changing a lot and we’re tweaking the the methodology and structure.

But essentially, I’ve had two side projects since I probably was in high school. I have little things that I was working on and to do them around a group of equally passionate and motivated people to have someone leave me. I don’t always leave them. I was in a cave today, actually, and it’s nice to just sort of jump in and be led by someone who’s keeping track of time and keeping me motivated and focused and accountable to get my most important work done.

I think ultimately the way that we see this is like there’s two kinds of work. There’s shallow work, which is just sort of defensive or responsive. I’m answering emails and getting my slack to zero and making sure that everything is off my plate. And at the end of our days, like if we spend our days doing just shallow work, we feel sort of empty, like I need to work a little more because I didn’t do any real work today.

Maybe you and your listeners feel that same way. And so the other side is deep work. And if we can sort of prioritize is the most important, most challenging things without distraction to put away our phones and to close all the tabs that we don’t need and didn’t just focus on that one thing. That’s what’s going to make our careers and our years and our months and or even our days meaningful when we get to put time towards these things that are, you know, the most important work we have, whether that’s like office and work and company related or just a side project.

Yeah, I mean, I participate in the session. I felt like, first of all, Robert Zeitlin, who believes in it, so much money came highly recommended. It was crazy because at the same time as he was recommending November. Yeah, exactly. And I don’t believe robbers from our session. I don’t know. I think he was the one before or after.

Oh, yeah. Right. Like six or something. And then it came highly recommended. I was like, all I do remember what do I remember this? I think literally within twenty four hours then you emailed me and invited me to check it out. I was like, whoa, this is kind of weird. You know how the universe works. We just don’t know. And I was so excited to sign up and as a new comer, I had no expectations of what it’s going to be.

And I must say that I was really surprised for anybody listening, watching right now. I showed up to a room of, I think, 80 to 90 people. I was expecting single digits, to be honest. And I was like, whoa, this is like a real community. And it was very soft. Because before you join and there’s a link of cave data org that we include in the description here, what I thought was really interesting was before, during and after as well, which is the before that you have that you listed or cave day provided a list of sort of how to manage distractions and download these like chrome plug ins.

And of course I was like, oh, I have that. Or I never heard of this. So I was already learning prior to joining the session and then during the session, there’s like groups stretching session that was really fascinating that every forty five minutes, every sprint that you have, that you’re encouraged to get up. And I remember a couple of times where I was in the middle of something, but because everybody got up, I was like, OK, now I’m going to get up and do this thing.

And I was a good feeling because otherwise I would have just kept going for like an hour and a half without knowing and everything and everything hurts and burning yourself out. And that’s where you get tired because you’re passionate about what you’re working on. So you want to work on it, you keep going. But what we’re trying to do is integrate the research and science and to say that your body and your brain really can only focus at its best for like forty to fifty two minutes.

So, yeah, taking breaks and making sure that you’re stretching and making sure that you’re connecting with other people, hopefully in your possession. You were in a breakout room for for another break where you get to talk about something personal and talk about getting to know other people and those moments of social connection and physical activity outside of our work help energize the stuff that we’re doing.

Yeah. What would you say as an entrepreneur that you perhaps have stumbled upon a period of your life prior to Cave Day to realize that maybe you’re overworking or you witnessed some of your family and friends were clearly over working without a structure or without that community and support like what was the inspiration to say what this is needed, that there’s a gap?

I think there’s a couple of things. There’s definitely like feeling overworked and burned out. I think the other thing is it’s really easy to get caught up into, like startup culture, hostile culture. Some people have called it hustle porn. It’s like I’ll sleep when I’m dead. If you don’t love what you do, you’re not doing it right. And and ultimately, like where all of those philosophies combine into this sort of evil sphere of like how capitalism and work is pushing us to sort of burn us all out.

The opposite side of that is is like thinking about our work as a relationship. And if you’re if your relationship to work is healthy, you know, there’s a give and take. I’m giving my time and energy and effort and hopefully I’m getting things in return. I’m getting a salary or time off for I’m getting part of my identity or maybe even like a portfolio piece or something. And when those when that relationship is is dysfunctional, when I’m like giving and giving and giving and giving my nights and weekends and I’m giving up my other relationships and I’m giving up my, you know, my self care and my sleep and my healthy eating habits, you know, it really is it makes it impossible to live a healthy and meaningful life.

It’s hard to, like, take care of your friends and family and show up for them. And it’s hard to take care of yourself. And so this idea of improving your relationship to work came from this idea that when I was when I was in the ad world and I am I cutting out for you, were you froze for a few seconds, but your voice was there the whole time.

OK, I’m sorry about that. I’ll try to work on that afterwards. So when I was in the advertising world was really coming to work eight, nine, ten o’clock, maybe once or twice a week, you’d work past midnight. And that was pretty common. It was just sort of the culture of the agency that I worked in. And on the days that I got to work remotely on the days that my partner and I would like work from a coffee shop and do our work at three o’clock, we’d finish all of the things that we needed to do because we were focused, because we knew we had to do, because we weren’t distracted, because we didn’t just buy into the fact that everyone’s going to stay late.

So I’ll just stretch my workout for another six hours. So true. You were done by three o’clock. We close our books. We send the emails that we need to send and we were having happy hour and getting to sleep at a reasonable hour and it just felt like a much richer experience of what work could be. So I’ve taken a lot of those elements and with my co-founders built what we believe is the cave day philosophy.

By the way, were you co-founders from Lemba or they’re maybe your friends from outside of the group?

Yeah, not not all NBA, just friends from Brooklyn, New York, creative, entrepreneurial world.

That’s awesome. I’m curious because I feel like I struggle with something. And that’s why Cave Day was helpful, because I remember going in with plan work to do. I mean, I remember knowing I’m going to be there for two hours. There’ll be about three sprints, for example, and then I need to do this work on that one. And for me to actually process that and to have a structure in place was really interesting for me to be very selective.

What I also learned is that there are a lot of things that take a lot longer than I originally anticipated and planned. I tend to be overly ambitious with my time with I said there’s also something that you mentioned. I’m like, oh, I want to learn that skill, which is you do something three o’clock, you’re done, you decide to go have fun, go play. I have trouble sometimes to be honest. I get too excited and I can always go back to my backlog.

I’m even a scrum master. I should know better, but instead of just pause, I always go to the next sprint or go find something else to do is satisfying and exhausting at the same time. But a part of me is like I can let go of time to chill time and watch TV. Like, how do you, as a busy entrepreneur of so many companies, dissect your time and say, I’m done for the day?

I’ll give you the cheap answer and the expensive answer and the cheap answer is that. I have a 20 month old daughter, the expensive answer, and volatility’s so so my daughter has changed a lot for me in terms of like I used to be the kind of person that was like I got to keep working. I was working late into the night and I’m giving you an example of ending my day at three o’clock. And it probably happened like I could count them.

On one hand, it just didn’t happen that often. But when it did, it was this amazing feeling, right. That when my daughter came around at the end of twenty eighteen, it really shifted a lot for me. It was sort of like, I want to show her that I’m passionate about what I’m doing, but I also want to be sort of like a super dad that I want to be around a lot and I want to. And that helps shift a lot of what’s actually important is, is sending out 15 emails to possible new clients going to be helpful today?

Or is making sure that she’s in bed or making sure that my marriage is healthy and taking time for that. And I also have realized through the work with KVOA that. That like taking a break and putting things down actually gets you energized, gets you focused in a different way when you pick it back up, like there’s a lot of writing now about the the four hour or the four day workweek that not you’re not trying to get 40 hours and four days.

You’re just doing a thirty two hour work week where when you when you condense your time, there’s something called Parkinson’s law where, like, work will fill the time that you give it. So normally we have 40 hours of work and we fill the week or whatever it may be. You’re working 50, 60 hours or more and we fill the work time that we have. And when we have shorter time, when we only have thirty two hours of work, you sort of cut out the best meetings and you cut out the like, wasting time doing this and that and one hour meetings and half hour meetings and you just get to things a lot faster.

And so I think that the maybe the cheap answer is like my marriage, my my family has allowed me to prioritize. And the more expensive answer is like thinking through what are your priorities, knowing that taking a break improves your work, sort of cutting the fat on your work and and maybe a practical piece of advice or something that I definitely do is keeping a list of the things that I want to do for fun, like personal development and fun things, so that when I am done closing my laptop or whatever for the day, I’m not just like, I don’t know what to do.

I’m just going to mindlessly scroll through Netflix looking for something. It’s like, no, I have a list of the shows that I want to watch. I have a list of the books that I want or have separated the books on the shelf from. I’ve read these. I haven’t read these. I’ve I have a little Post-it note next to my bed. That’s just like here’s what I should be thinking about, like do my Hebrew flash cards or stretch and anything like that, like keeping yourself a separate list of like non-work habits or non-work dos can help you not default into your bad Netflix show that I don’t really want to watch, but I need to take a break or important work.

So yeah, I noticed like behavior and habits changing is really profound. And for me to adapt Pomodoro method to do twenty five minutes, five minute breaks, which reminds me so much of a cave day except for I now I’m accountable. Like I almost feel like it’s part of cave day. If everybody is stretching doing their thing and I’m heads down doing something is like oh wait a minute, you know, it’s like you’re, you’re the weird one. You’re not the part of the army anymore.

And with the method, with especially pompadours so short. Twenty five minutes. Which cave is a little bit longer. I feel like even if I want to touch my phone and just reply to one thing, I’m like can do that because I got to finish this in twenty five minutes. I can’t afford to. We’re five minutes out of the twenty five. It just going to throw me off like somehow is reinforcing the importance of focusing while what you’re committing to do.

I yeah this is pretty, pretty amazing. I’m still just so surprised like how you’re able to trust me because I know it’s hard, it’s hard work to build from an idea or to a project and a project to a company, a company. Now that runs cave day, like you said, five days a week. And there are multiple sessions. Guys are designing like one of the day, another four to five times a week. And I’m maybe I’m jumping the gun to ask about the process of growing from and they’ll go for it.

So I mentioned we launched the NBA in January of twenty seventeen and it was just supposed to be a one time event. It was like, let’s get our friends together. We’re going to do some research, we’re going to put on this fun event. We’re going to get a cater that’s going to be snacks and lunch. We’re going to bring in a coach in case you need a break and want to meet with a coach. And we charged maybe it was fifty bucks at the time for a full day with lunch and coffee and all that.

Wow. And we sold out and it was like, this is, you know, 50, 60 people showed up. I think each of the co-founders and I may maybe it was like two hundred dollars that was like, this is kind of cool. We made some money. People loved it. We’re providing value. So we did it again in another month or two and somebody happened to be there that was a journalist and was working on his own project and decided to write an article for this company about Cave Day.

So we got this huge press in our third month around and sort of built the momentum to grow. And we just kept it as this little side project. We would meet once or twice a week, just for an hour or two. What do we want to do for the next one? How are we going to change it? And in the last really what really shifted a lot of things is actually I mentioned my daughter was born in October of twenty eighteen and.

My co-founder, Molly, her son was born in August of twenty eight, six weeks apart, and we were both going to take some time off as entrepreneurs. I can go into a whole tirade about taking time off and maternity leave and paternity leave, but not going to do that. We wanted to take some time off, so we actually needed to hire people to run the case that we were doing. And so that was the first sort of step in the growth that we’ve been doing, which is creating a curriculum, really putting our philosophy into words and being able to teach it and bringing on more people.

And since then, I think we have 15 or 16 facilitators across the world. We’ve got facilitators in Amsterdam, Toronto, San Diego, Denver, New York, D.C., Philly, all over the place. And yeah, it’s sort of great. And with covid and working from home in the last couple of months, it’s been sort of amazing to see how this has grown kind of organically and actually a funny, funny story, if I can. Yeah, one more minute and two more minutes.

So when all of this started, we had said, hey, we should put together a webinar, how to work better remotely, how to. And and what we did is we sent out 10 emails like March 10th. Right at the beginning of this, we sent 10 emails to former clients and corporate connections that we had. And we said, hey, are you interested in a webinar? Its how to work better remotely and sort of immediately. I think we got six responses within an hour.

Everyone said yes and we said cool, it’s going to be whatever with a thousand dollar fifteen hundred as a company. And then, you know, we’ll, we’ll work in cave day membership, be on that or something. And every single one was like, sorry, we don’t have the budget, we don’t we can’t do that. And so what’s been really interesting is that that sort of mistake of thinking we should charge for something shifted our strategy and sort of the way we’ve been treating the last four months and covid, which has been we just gave it away.

We said, let’s list something, let’s do it for free. Let’s help people now because we know we have something valuable. And so we did four webinars back to back weeks, the same webinar, each one sold out. It was like one hundred people in each one. And we’re continuing to sort of find the right partnerships. And just to to be generous, we’ve got a lot of people that are signing up and then sort of canceling their membership because they build email and say, I lost my job, I can’t really afford it.

And we have scholarship and we have a pay what you want month for those kinds of people. And we’re trying to be generous knowing that, like what we’re actually doing is including you in part of the world’s most focused community, we’re including you in a way to build a better habit around your work.

So, yeah, with so many different experiments and to I mean, these stories, you never hear from entrepreneurs and for people who are working there nine to five, noticing that there is clearly a very, very dramatic shift, that it would just be so much better, at least from what I hear from my my cohort, my group of people is people are working full time. They’re like, oh, man, I wish I started something on my own a few years ago just so that I’m in the game, that I have that momentum.

But hearing you talk about these things, I think is very encouraging because a lot of people feel like they have failed or they’re going to fail. People won’t come to them. They don’t know how much to charge. So I feel like for me as well, there’s that imposter syndrome kicking in when I’m doing something new. Maybe it’s a cause. Maybe I’m trying to finally sell something for you again. There’s like to look at your resume is quite a you know, it just astonishing, like the brands that you’re able to to create, not just to attach your name to.

So, I mean, first of all, congratulations. It’s amazing. Three amazing years since Al Tumba for you. And I want to definitely talk about School of Life. It’s one of my favorite YouTube channel. My I don’t know whether I was ever a book, but I’ve been following and I think there’s a high chance of a book, a book of life. They have a podcast, lots of books and lots of lots of books. And even though this is kind of a shift from cave day, but the more I talk to you, I’m more I get to know you is like, oh, my God, this is completely on brand for you.

I see Cave Day School of Life. I mean, it just like this continuum of what the whole belief system of living a life that’s defined by you that’s really in a way, unconventional in a way. That’s not what our parents taught us. And is the reality that we’re seeing for ourselves, so what so could you tell me a bit about this amazing UK based School of Life company and you become one of the founding US faculty member. How did that come about and what did you create for them?


So, first of all, I want to just say, like, thank you, I’ll take the compliment. And for all of you listening, I don’t want to pretend like I always know what I’m doing. I think it’s nice to hear that all of those things feel cohesive. And, you know, every three months, every six months, I’ll sort of go into it. How do these fit together? What am I doing? I don’t see the connection between Cave Day in the School of Life and Design.

I feel like they’re separate and sometimes that anyway, so that he says to me, I mean, I feel like I’m in cohesive, but no, your brain makes perfect sense.

It’s always easier to see it in somebody else. So thank you. And I just want to say, if you’re listening like it’s OK to not see the connections yet, patterns show up and keep doing what you’re enjoying doing. So I think, like you say, I’ve always been a fan of the School of Life. Must have been four years ago I was on a I think it must have been my honeymoon. It was like summer of twenty sixteen.

I was in Europe and came across this design store and I think I spend like three hundred dollars. I’m just like books and cards. And I was at school, which is amazing. And then I got into there, I got into the YouTube channel and I was just like, this is everything this is like. Emotional intelligence, emotional intelligence at work, self-awareness, almost like philosophy and psychology together is really interesting. So I’ve been following them for a long time and as a freelancer and someone sort of interested in teaching in general, which is just a quick side note, I’ve taught different college courses for the last eight or nine years, like it usually creates the creative process, copywriting, branding, stuff like that.

So I love teaching. I love being in front of people and sort of facilitating learning. So as a fan of the School of Life, as a freelancer, I was sort of like pretty desperate to find my way. And I was like connecting with everyone on LinkedIn and trying to send the messages. And you meet with me and maybe I feel like I could design your website better. It’s like trying to offer help and getting nowhere with it. And I happened to look online and they were it was like at the beginning of twenty eighteen, something like that.

And they were they were looking for a part time facilitator in New York. Like that is perfect. Yeah, I apply and I found the person who had posted the job and we had a mutual friend which was like someone in London. So I asked for an introduction and we had just a 15 minute call, just like introducing myself. And when she came to New York to do all the interviews, we got coffee. And and that personal connection definitely helped.

But I don’t want to downplay that, like there was also an audition. So I should say that, like, what the role was for is that the School of Life has a school of life for business branch where they may have 20 different workshops that your company can hire the school life to come in for one of these twenty one of these two hour workshops. And the role is just to facilitate the workshops in the United States for their US clients.

So part of the process was auditioning and I memorized the I like a 30 30 minute chunk of one of the workshops and it was something that I felt very passionately about. It was related to cave day work. It was the topic was effectiveness. So how do you show up? How do you choose and prioritize what to work on? And I’ll just I’ll say sort of in a moment of non humbleness, like I crushed it. I was like I had their attention.

I made them laugh. I was great. And and they offered the availability to watch everyone else do their auditions. Yeah. And it was just so clear from the beginning, like, oh one people didn’t take this seriously. People didn’t study, people were reading and not memorizing know there was just such a wide range of like what people came thinking this was supposed to be. And so yeah, I’m I’m one of I think two, maybe three US faculty members.

I’ve been around I’ve been working with them for a little over two years. And I wish that I could understand your question. I wish that I could take claim that I created things for them. I have not, but I facilitate workshops for them. And I’m in sort of weekly contact with their content team about. Giving them feedback, giving them suggestions about making the workshops better and what’s actually been really nice in this coded time is that I’m booking a lot more workshops with them.

They’ve got I’m leading workshops in the US and in Europe. And so I’m leaning more often. I’m more familiar with the content. They’re testing things out. I’m giving them more suggestions. And it just feels like a company that I could see myself growing with and being a part of because it aligns with my own personal values and philosophies and related to cave day and sort of everything else that I’m thinking about these days.

That’s, I think, something not to overlook there is that you found a brand in your school of life. In my case years ago, I saw Cirque du Soleil for the first time in my life and we just blown away. And you find yourself laughing, scared, cry and praying for people on stage. And I think I did something very similar I reach out to, in this case, the Atherton twins. Turns out they actually created that act, but I was not watching them.

They’ve already moved on to other shows. And yeah, I mean, they didn’t have, like, the most intuitive website, but there was one email address. I reached out to them and three years later, they’re in the in my documentary, we have an online course together. I redid their their website. That was the first project. So there’s something about I think there’s some level of not just interest, but intuition. By the time that you became a short list of facilitators and it was already like you already integrated the knowledge, somehow embodied that because you believe in the brand.

And I absolutely I’m not sure about everybody else there just saw it maybe as a job, but there were maybe not as in love, in love with the content, but on top of that, your professor as well. So that’s that takes a lot of practice that people won’t be able to to get over the weekend where you practice with your mom, your sister. But you had already been a professor for years at that point.

Yeah, I think that’s a great realization that I maybe didn’t think about enough about how when you follow a brand, when you are a fan of someone or something like when you end up talking to them, finally, if you can sort of withhold that inner sort of starstruck nerd out 12 year old self, like, give me your autograph, you can actually have much deeper conversations because you’ve you’re right. You’ve I’ve internalized the teachings and philosophies. Sounds like you as well.

And I think it’s also rare, like I could think of maybe like a musician that I loved in high school and the school of life more as an adult. But it’s not like I have a list of 50 people that I’m in love with. It’s there’s a few and far between tween. And so they’re really looking up to them and diving into their work is it seems like it’s important.

Yeah. So my last question related to Cave Day and the School of Life as you’re talking and thank you for reflecting, as always, is, you know, how do you balance your project versus their projects? And so in this case, your creator and you’re also a consultant slash facilitator like do you find that more exciting? I know some people are like, I can only do my thing. I can only work for somebody else. And you’re kind of in the middle of that.

How do you balance how do you enjoy the process?

I don’t have a great answer to that, I would say. I think what I’ve learned is that one helps with the other, that by because maybe it’s because Cave Day focuses on how you show up at work and maybe just by necessity, because cave day is probably only like a third of my income, like I need to go look for clients and I need to go take contracts to work in house and a brand or an agency or something. So maybe by necessity and the like, just the way that the work integrates, but.

Maybe just I don’t know if I have a great answer, but I’ll just I’ll share a little thing that I’ve started to do in the last year or so or at the beginning of twenty twenty is that I have I make my to do list in for like four categories. I do cave day, I do my design work, I have my personal and I have teaching. And typically it’s like my work falls into design, teaching and cave day. And then I think we all have personal things that we want to get to.

It’s whatever. I don’t have to explain personal stuff and I have it mapped out by day. So Monday, here’s what I have to do in each of those four columns. And with each one I put a star next to the most important task of the four or of the four columns, like what’s the most important task of the day? And some days or some weeks it’ll be like, you know, I’m working on Cave Day primarily for two, three or four days of the week, and I need to get that design thing done or I need to just sort of refine that logo that’ll take me an hour or two.

So I think in terms of prioritizing, being able to segment my work, being able to, like, step back and sort of order, what am I going to do when on which day? And like also I’ve tended to put my most important work first thing in the morning, like by by 10 or 11 o’clock in the morning. I’m done with my hardest task so that my afternoon is podcast’s and going for walks and calling friends and meetings and sort of the easier task.

And that level of prioritization has helped a lot.

When do you wake up, by the way, was where the sleeps such a lot of people interested in that. When you wake up, when you go to sleep, typically shirt.

So without a story I wake up at five forty five. I go to sleep at nine thirty.

Oh wow. All right. That’s, that’s clearly that’s well trained. You’ve probably conditioned yourself to, to be that in that schedule.

Yeah. My morning routine is very rigid and has been that way for several years or at the.

Oh cool. I know you don’t want to get into it and we don’t, we don’t have to. But at a high level where is it like that. Just 10 varies. But this is there a model that you are adopting? What did you kind of invent yourself for yourself?

The morning routine. Yeah, what I did. It’s something that I’ve developed over time, I can’t tell you like to read Tim Ferriss, I’ve read Benjamin Spall has a book, My Morning Routine, or Mason Curry has this book, Daily Rituals, like I’ve read a lot about rituals. And so basically I’ll just I’ll explain that I wake up at five forty five, I’ll drink a glass of water, I’ll have a banana, I’ll start journaling, I stretch, I do my exercise and then I do my most important task.

And usually that most important task is started by seven. Looks like it’s an hour of exercise, stretching, journaling, maybe some meditation breakfast. So it’s pulled from all the different places and it’s tweaked over the years. It wasn’t always five forty five. Sometimes it was earlier. More than often it was later, but. Yeah, I picked and chosen what works for me. What have you shared on your podcast? I’m curious about you and your morning routine, if you can.

Oh, I’m terrible. I am. What do they call, like, large personalities? I think Daniel Pink’s The Lark versus Owl. I am my whole family. I, I’m so fascinated. Trust me, I try to adapt to the waking up early, but I am most productive at night. And sometimes my mom, my mom’s stuck here with me because of covid came to visit me from China. We’re having a great time. But she will pop and she she she’s an artist as well and she paints at night.

And like I grew up watching her paint like 3:00 in the morning. So now she like peeks into my office and said, oh, it’s midnight, you should really go to sleep. So by midnight, I feel like I got something left in me. The writer concluded, check things off the list. Then I wake up, to be honest, fairly late the next morning, usually like a thirty or so. How’s my energy level? Not always, not always great.

But the problem I was going to say that I would. It’s probably takes time. I was going to say like when you go to sleep at nine forty five or ten, like how quickly do you fall asleep. Because I tried that, I’m like staring at the ceiling like I need some sort of tea or honey you can’t sleep. I think I maybe this is just because it works for me but I am an easy sleeper. I know my wife makes fun of me that like if we we don’t go on the train now because we don’t go on the train.

Yeah. Anyway, but when we would go on the train that would be three stops to get to our apartment and within three stops I could fall asleep like ten minutes. And I think part of it is when you wake up at five thirty five, forty five, six o’clock like yeah I don’t drink, I don’t drink coffee. Maybe that me that helps. I just, I get tired, I’m able to fall asleep and you know, if, if it doesn’t work for you, if you’re not an easy sleeper then I wouldn’t recommend it but.

You know, there’s a lot of writing and tips about improving the way you turning off screens and out of where you go, dimming the lights, reading all kinds of things that can sort of put you in the right mind set for sleep.

Yeah, and it’s super fascinating to actually hear people trying something. And I am open to anything. I love running the experiments on myself these days. I love going on 30 for 30 days. I love trying Quito and realize it doesn’t as much as I believe in it. It doesn’t work for me, I think because I notice I Akito diet for Asian people just doesn’t always work well because we were never ever on those sort of diet heavy in protein and sort of dairy products and things like that.

I think what what I love about what you’re saying is that like doing these experiments not to like look for results. You’re not like looking to drop 30 pounds in 30 days. I think the interesting thing about doing these kinds of experiments is to learn about yourself is to do a one month of a new diet, one month of no spend any money, one month of only cooking, one month of no alcohol or whatever. Yeah, I do it. And the goal is not necessarily to look for different results.

The goal is to say, one of my learning about myself, what do I need, how do I implement that learning into a new habit or a new, I don’t know, world view even.

Yeah, the world view is such a great example because I you know, this is not me urging everybody to go sign up for all Temba or join other groups. But, you know, I think we’re so lucky. Jake, are you based in New York, I assume? Yeah. Are you OK? So I’m based in Boston and I have friends in Philly, not in California, but there were a lot of people who have never been exposed to entrepreneurship the way that we have been.

When I talk to people, especially during covid, that I talk to people and I hear the struggle of I come from a military family, nobody in my family has done anything like this. And I’m not being supportive perhaps or understood by my family. And that’s when I feel like for a lot of people going through all be going joining Doree Clarkes group is changing their world view is like, oh my God, I don’t feel it. It’s exactly possible.

Relatable stories and that you are some people feel they are not well liked at work when everybody wants ninety nine to five, a couple of kids living in the suburb and they want to go see the world in their thirties, people like what’s wrong with you, but then they find their people and they’re so much happier. It’s really fascinating. Yeah. Yeah. So I know that I book forty five minutes and I knew we were going to talk longer for day.

Before I wrap up here, I really want to hear a bit about MoMA. If it’s a longer sort of time for it, I’m all for it.

It’s a short story. I’m happy to share it. So the claim to fame is that I have work in the permanent collection of MoMA. And the truth behind that is I was the creative director of a small agency here in New York City. We were working on a social impact project with the Clinton Global Initiative. This is in twenty, fourteen, fifteen or fifteen, sixteen maybe. We made a VR film that was the work of the Clinton Global Initiative was doing in East Africa.

It was a really interesting film where it starts off and you’re sitting across the desk from President Clinton and he’s explaining, although it’s a really intimate thing when virtual reality was just starting. Yeah. And we won an award. We won the ACP, the American Institute of Commercial Producers next award, which was sort of innovation in the field and storytelling. And I don’t remember all the qualifications I heard of it. Yeah.

And part of being awarded this award is that it goes into the MoMA permanent collection. So it’s it’s never been displayed at MoMA, but it’s it’s there and it’s a technicality of the award. And I’m happy to claim it on my bio.

But you do it. That’s amazing. Sorry that that story is amazing. You’re an art director and it just it’s it doesn’t get any better than that. OK, MOMA is the.

I know it’s at the top and I think it’s still on my life list is to have a product sold in the gift store. I don’t know what that will ever be, but this stuff is so cool and it’s always been top of my list. And so to technically claim that my stuff is in the permanent collection is is cool. It feels a little bit like cheating, but it’s true. But yeah, the little side that you draw also, I was really surprised to go to like I thought that’s what you meant.

I went to Instagram, finally found your profile because we’re connected elsewhere. And I saw and just pages and pages of baby pictures. I assume you’re drawing your daughter and other inspirations as well.

Yeah. So I, I draw on my daughter a lot here. It’s in the right here that that’s where it is. Oh yeah. Yeah. That Jacana. I went to art school when I went when I wanted to go into animation. Maybe this is a good full circle story, but I went to art school thinking I was going to go into animation and I ended up with a degree in fine art. So I took drawing classes and illustration and graphic design.

That’s why I love art. I have drawn and painted my whole life. I miss it. And so I don’t know what. Five, six years ago I was like, you know what I haven’t painted in a long time? I sort of funneled all of my creative outlets into design and client work and filmmaking and advertising. I need to get back into just like pure art, like, you know, like your mom just like 3:00 in the morning painting, like getting into that flow state.

They’re beautiful. So I try we talk a little bit about daily habits, trying to integrate. Is there one night a week where I can get 30 minutes of drawing in or can I can I get ten minutes a couple of times a week? So I have lots of sketchbooks and I paint a lot from time to time. I’ll get bigger projects, a mural here and there. But then I just love drawing and painting. I miss it. I feel like I’m in a slow state.

And actually, maybe as an interesting closing story, about two years ago I made a project of painting. It’s called Forty Five Villans, and it was Donald Trump as famous villains in history. Maybe, maybe some nice.


So is this project. Forty five villains. And it was him as like the killer in Fargo and the the Wicked Witch of the West and the sort of like a playful way to say, like he’s the villain, get it. And I put I put them on Etsy and ended up selling. I made like a couple hundred bucks and and it was it was cool. And so the next year I decided maybe one of my goal should be to make a thousand dollars for my stuff, for my art.

I need to be doing art more. And and really quickly, I realized that that was a really bad idea because this is something that was like an outlet. This is something I love. This is something that I do for fun and for flow and just and the idea of having to make it make money was really got in the way of doing it for fun and for what I love. So I’ve actually shifted from like I need to make my art make money to like and purposefully not putting anything else on Etsy and not selling my art, at least for the time being.

Like, it’s just nice to have things that are not going to make money that are just for my soul.

I mean, that is so important. We don’t talk about that because it sounds like a privilege. And I know it is a privilege for creative people to say, but I don’t have to translate everything I do into money. But I think we need to even more consciously create space for ourselves. And that’s precisely the space I needed with podcasting, which I started in twenty fourteen because I felt very unsatisfied through my my full time job. And it was so childish of me really to think that my job somehow needs to fulfill these creative endeavors and all these thoughts.

And and I just I think I’m also someone we need so much of that on the side. Maybe I need it. The spiritual stuff more so than some other people. It doesn’t make me better or worse or anything, but I needed that. And I started podcasting. The first thing a lot of family and even friends, I just like how much money you’re making. If you’re not, what’s the point? And especially was very obvious, especially in my in the Asian community, particularly at home and from home in China, people are like, what is the point?

You’re not making money? And I it took a it was very challenging to hear that message, but to keep going, keep rolling with the podcast. And two years later, believe it or not, because of that, I started my own company. A lot of people don’t realize that I was talking to Torie Clarke and she encouraged me to say, oh, you converted a lot. A lot. I didn’t. Convert, I didn’t do anything to my guests, listeners, a lot of guests, friends, start referring so much digital marketing work to me and I was really shocked because like a show or I like you, I’ll do this.

And and then it just started to grow completely organically.

I think that that is definitely under. Under talked about and the idea of doing something not just for money, but because you’re good at it, because you’re interested in it, just because you’re going to learn something, I think you’re right to call it the privilege and that. But if you’re able to, who knows where it’s going to lead. But I think it’s a dangerous place to just say we only do things for money because then we live lives that are just chasing money instead of chasing.

You know, I think the point of getting money is to be able to spend it on the things that you are having and doing. And money is not the obstacle. Money or money is not the objective. Money is the way to get there. And so I’m a nice place to wrap up.

Yeah, for sure. For sure. Thank you so much for joining me. I’m going to take us offline now. Bye, guys. Thank you. All right, thank you so much for your time. I really appreciate it.

No, I thought we’d booked an hour. I mean, like, I’m happy to talk. This is your. You’re a great interviewer, and I’m just fascinated by your own story and getting there. So this is great.

Thanks. Oh, it’s so fun. Absolutely. And. This episode of the First World podcast is brought to you by First World LLC, our marketing service agency created for independent creators and businesses. We offer website development, video production, marketing, mentorship to people who want to tell better stories, level up and create a profitable brand. These were a podcast team. Our chief editor and producer, Herman Silvio’s associate producer, Adam Lefort, social media and content manager, Rosta Leon transcript editor Allena Almodóvar.

And lastly, myself, the creator and host of Face World. Thank you so much for listening.

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This is part of Feisworld Podcast’s Meeting of the Minds series, which I started at the beginning of the pandemic. I’ve been livestreaming my conversations with these teachers and influencers so you can see the complete and unedited footage.

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