BEST OF: Evernote co-founder Phil Libin on the key to making better decisions at work - podcast episode cover

BEST OF: Evernote co-founder Phil Libin on the key to making better decisions at work

Apr 27, 202241 min
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Episode description

**BEST OF**

It’s 9:30, and you’ve got just under an hour before your next Zoom meeting. There’s already just a bit too much caffeine buzzing around your brain, and your eyes are half-crossed from the last video call. So how do you recharge and show up refreshed for that next one? 

If you’re Evernote and mmhmm co-founder Phil Libin, you swim laps. Thanks to the “distributed” nature of mmhmm’s workforce, he can punctuate his work days with distinctly not-work activities. Some days, it’s laps between meetings, other days it’s a stroll around one of his favourite museums while he ponders new ideas.

Whatever he chooses on any given day, it’s only possible because of one of the many superpowers of the internet. Phil is happy to solve a few problems with our new way of working, if it means he gets to keep the many, many benefits of working asynchronously and away from a traditional office in the big city. 

Phil shares his favourite tips on making the most of remote work (including why he doesn’t like the term “remote”) and some of the biggest lessons he learned as the CEO of Evernote.  

Connect with Phil on Twitter or Linkedin

 

Visit amanthaimber.com/podcast for full show notes from all episodes.

Get in touch at [email protected]

If you are looking for more tips to improve the way you work, I write a short monthly newsletter that contains three cool things that I have discovered that help me work better, which range from interesting research findings through to gadgets I am loving. You can sign up for that at http://howiwork.co  

 

CREDITS

Produced by Inventium

Host: Amantha Imber

Production support from Deadset Studios

Episode producer: Jenna Koda

Sound engineer: Martin Imber

See omnystudio.com/listener for privacy information.

Transcript

Speaker 1

Hello there, it's Amantha.

Speaker 2

I'm currently on a break, so I've handpicked a bunch of my favorite episodes from the last year to share with you.

Speaker 1

Okay, on with today's best of episode?

Speaker 2

Can everybody see me? Just wait, I'm going to share my screen. Wait, hang on a second. Okay, how about Now we've all sat in these dry zoom presentations that are slow, boring and engaging and often just plain painful.

Speaker 1

We think to ourselves, how much longer is this going to go?

Speaker 2

For and don't forget to smile and look like you're listening. But does it actually have to be this way? Co founder and CEO of Phil Libbin thinks definitely not.

Speaker 1

He's designed a tool that will.

Speaker 2

Have your colleagues entertained and even laughing during presentations by providing you with lots of fun tools and gadgets to utilize so to stop your workmates from tuning out. And this isn't the first time Phil has looked to make life better and easier with technology, because before m Phil and his team created the life changing note taking app Ever note which I have been using every single day, many times a day, for the better part of a decade.

So when it comes to building a business, which Phil has plenty of experience doing. Why are the numbers three and ten critical? And why is it better to be positive during a meeting instead.

Speaker 1

Of trying to appear to be smart?

Speaker 2

And how can working from a museum help you solve complex problems? And why is it important to differentiate between difficult versus unpleasant decisions. My name is doctor Amantha Imbat. I'm an organizational psychologist and the founder of behavioral science consultancy in Ventium, and this is how I work a show about how to help you do your best work. So I've been using Phil's latest technology product mm HMM

spelled mmmmm for about six months. Solves one of my biggest frustrations with traditional meeting software, which is that the slides when you're making a presentation are really big, and the human presenting becomes the size of a postage stamp. So with m HMM, you can superimpose your slides in the background and put yourself in the foreground at any size that you want to be, which is great for actually making a connection with the people that you're speaking to.

So I wanted to know from Phil, who has obviously thought a lot about this, what is the ideal way to use slides in a meeting or a presentation.

Speaker 3

Well, I think companies who make presentation software, you know, who are in the business of making slides, they very naturally act as if the slide is the most important thing, and so like this whole like PowerPoint culture of slides.

Speaker 4

Kind of comes from that.

Speaker 3

And it isn't like you're you're much more important than the slides that the presenter, the person doing that the talking is much more important. So the slides are really there as background material, which is why we literally put them in the background instead of you know, right next to you or in front of you in most setups, because the focus really should be on you and your face, on on how you're communicating, and having the slides be

you know, a visual reinforcement of it. We're trying to change the cognitive style of presentations because they think that the cognitive style of PowerPoint is is quite weak. It's the style of you know, of pitching of bullet points of things like that. They're these sort of lazy crutches that don't lead to very effect presentations, and I think on video they're just terrible. Like they think PowerPoint is barely you know, effective in real life on video, it's

it's pretty much unbearable. Luckily, there's plenty of examples of really effective video communications and slides. You just have to go to TV. You have to go to comedy shows, I don't know it live or the Daily Show, that kind of stuff. So we just tried to recapture that kind of spirit where it's a person talking or multiple people talking, and the slides are meant to kind of be the punchline, the visual reinforcement from time to time.

Speaker 1

I love that.

Speaker 2

I mean, it's in a way, it's kind of it's such an obvious thing to do to put the person in front of the slides, And certainly one of my pet hates in terms of how Zoom works is that the presenter is the size of a postage stamp and the slides are enormous. And for me that was a game changer when I started using HMM and suddenly the

focus is on the human. So I'm curious for you, when you're creating a slide deck, when you're trying to put forward an idea or a presentation, what are some of the rules that you're thinking about when you're designing slides.

Speaker 3

In the beginning, I think I just started. I was just using my keynote slides out of power slide. I was importing him in there you can drag him into MHM and doing that, and some people still do that. I pretty much stopped doing that almost immediately because I realized that actually I wanted the constraint of altering the slides in MM because they're.

Speaker 4

Much they're much briefer, they're much shorter.

Speaker 3

So usually it's just a couple of words or a gift or a picture or maybe one chart. There's no point in having, you know, multiple sentences, multiple points, multiple equations on a single slide. But when you have something like PowerPoint, it really it really breeds this style of trying to just load it up with stuff, which makes I think the presentations really, you know, really untenable, really unwatchable.

And it's almost as if like your slides are meant to be viewed, like your deck is meant to be something to be viewed without you, but that never works, Like you should never send your slides ahead or behind or something like. Your slides are not a document, it's not a novel. It's not meant to it's not meant to exist without you presenting it. You should make a video with you presenting the slides together. But if you look at it that way, then like, well, how complex

and intricate to the slides have to be? Well, not very at all. So I just try to keep it as simple as possible. So you know, yes about rules like trying to keep things simple. So the first the first rule of simplicity is simple as hard. And the second rule of simplicity is there's obviously only one rule of simplicity. You clearly haven't understood the first rule.

Speaker 1

Yeah, I like that.

Speaker 2

I wanted to know, like, what are the features that you're using in M and maybe if we take a step back from that, I mean, I guess I've kind of described how I use but how do you describe and what it is?

Speaker 3

Yeah, it's it's a video communication tool. It's really meant to give you, you know, video superpowers. I think most people start by using it by when they're presenting on Zoom or Google Hangout or Google Meet or Microsoft Teams or WebEx or something like that.

Speaker 4

That's the most common use case right now.

Speaker 3

People just using it to present to make the presentation a lot more more interesting, more more, more expressive, more dynamic. What I and I still do that all the time, but what we're doing now and our company is actually shifting almost all of our communication to asynchronous. So we've gone from talking to each other live when we're doing status updates to just sending recordings around. So we have you know, TV where people are just sending recordings of

them doing presentations and updating each other. And we save the synchronous communication for for what you and I are doing right now, for actually having a conversation where we you know, we take turns talking, not for one person lecturing and the other person listening. So more and more it's about it's about shifting from synchronous asynchronous communication and kind of smoothly going back and forth between those two.

Speaker 1

Interesting.

Speaker 2

I want to know what features your planning on building in m and and what you're most excited about.

Speaker 4

Well, we are.

Speaker 3

I mean, I'm easily excitable. I'm excited about lots lots of stuff. We've got a really ambitious roadmap. We announced a lot of the stuff this summer. We had this content series called Summer, which is on our website. If you go to that app and click on the events section, you can see a bunch of our demos and keynotes and all of that stuff that we announced and demo

and preview that's all coming out. There's a bunch of stuff around what I kind of think of as the djification of the world, where like you can kind of be a DJ and smoothly mixed between synchronous and asynchronous parts of your of your video, so you can started meeting live and then switch to something pre recorded and then switch back to live and do that, do that kind of smoothly and effortlessly. We're launching versions on an iOS, on Windows, We're launching a new version for the Mac.

We've got, you know, lots of lots of product updates coming out. But yeah, just watch watch the watch the keynotes from from the summer to get a sense of all the stuff that's coming, you know, between now and a month or two from now. Now.

Speaker 2

I imagine, because of the timing of when you started m HM and you've been building lots of features along the way that you would have had to rely heavily on virtual collaborations. So I'm wondering what's been your approach to doing that.

Speaker 3

Well, Well, I don't know if we've done it well, but we've done it. You know, it's actually been great. I think when we started in May. We launched May twenty seventh of twenty twenty, so we started a couple of months after we all went into lockdown, and it really started as a.

Speaker 4

Joke, like we were just you know, we were so bored.

Speaker 3

All the all of the video calls are so tedious, and we were just goofing around. We're just trying to find something to make us laugh while working on other projects. But it kind of snowballed from there and so mm hmm. It was completely created in a distributed way. You know, we're up to close to one hundred people now working on and the vast majority of them I've never met each other in person. You know, it all hired them during the pandemic. Fully globally. They're spread out all over

the world and it's great. I think the main thing is we don't think of ourselves as remote. No one is remote, because remote implies a certain disadvantage, like you're remote, but other people are somewhere, you know, together.

Speaker 4

We're not remote. We're distributed.

Speaker 3

We're distributed by design, kind of like you know, the Internet is a distributed system. It's a distributed network, not because the people who created the Internet didn't know how to make a centralized network, but because, like, being distributed is kind of its whole point, that that's the superpower of the Internet, and it makes certain things a little

bit harder. You know, a few things would be easier if the Internet had one big central server, but obviously, like no one thinks that that's a viable thing because it has to be distributed by design. On so we are we have we have designed our company to be distributed, not because we had to, not because like we don't know how to be in an office, but because of the massive advantages it gives us.

Speaker 4

And when you think.

Speaker 3

About it like that, we're rather than focusing on the on the few things that are harder, when you're a distributed team, you really focus on the many things that are better and that are easier. It makes everything, makes everything more fun, it makes everything more productive.

Speaker 2

And so, aside from the obvious advantage that you can find talent anywhere on the planet, what have been some of the other really big advantages around being distributed.

Speaker 3

Well, you know, the talent piece is like, let's not dismiss that too quickly. I mean, that's that's just that's worth it, right, Like you know you've talked to CEOs before, all right, And I'm sure whenever you talk to a CEO, literally one hundred percent of the time, if you ask, hey,

what's the hardest thing about this company? I guarantee you've only ever gotten one answer, because you know, when we go to CEO school, they teach us if anyone ever asks like, what's the hardest thing about your companies, only one answer we're legally have to give. We have to say, Oh, it's it's the people, it's the talent, it's hiring and getting the best people. Like that's literally the only thing that any CEO's ever said in response to that question.

And it's true for the most part. And so here we are we as you know CEOs you say in the past, you know, fifty years winding about how the hardest thing is people, and the universe has just given us as great latest gift, the superpower where every single job in my companies is now global. Is now I can hire people from everywhere in the world, and they

they can stay where they are. They could do the job the top of my talent a funnel has just expanded by thousands of times, and I'm going to give that up, Like, of course not, I'm never going to give that up. So yeah, the fact that it's a fully, fully globally distributed workforce is amazing. But that's just the type of the iceberg. Another big, you know, benefit is, you know, no one wastes any time commuting. Like one hundred percent of the people who work at our companies

don't spend any time commuting. Imagine if, like somehow magically that had always been the case in our company, like somehow, you know, like alternate Earth, you know, Harry Potter style, like people who just teleport to work to the office.

Speaker 4

No one ever commuted, And.

Speaker 3

All of a sudden, like I come into the office the next day and I say, hey, everyone, like, everyone gather around.

Speaker 4

I've got a CEO idea. I'm going to need each of you to spend.

Speaker 3

To waste two hours a day sitting in traffic. Yes it's not very productive, and you can't work, and yes you're not any of the time with your friends and family, and yes you can go like to a good restaurant or listen to music, and yes it's very unhealthy and very stressful and oh my god, it is terrible for the environment. But two hours a day, every single person wastes city and traffic go right, Like the board would be like, see you, it's gone crazy. It would fire

me immediately. But you know, that's kind of what we're asking people to do if we want them to quote unquote go back to the office. And then you know the fact that that one hundred percent of our employees can choose where they want to live. They can they can live in a nice house if that's what they want. They can send their kids to a good school. They can live in a city, they can live in a small town. If someone's always wanted to live on the beach and surf, they can do that today and still

have their job. And then, like for the first time ever, every single person who works in our companies, who works in a distributed company, can choose where they live to have their best life independently from where they work to have their best job. I mean that that's amazing. We're never giving that up. And there's like there's like twenty other superpowers that are kind of like of this level of caliber, and when you think about them, you're like, well, yeah, I'm not.

Speaker 4

I'm never giving these up.

Speaker 3

So sure it's worth solving some problems to keep these, but I'm definitely keeping them.

Speaker 2

And so when it comes to collaborating with people that you've potentially never met face to face, like, is there is there almost like a template or a system that you use, Like when do you know when to be asynchronous versus synchronous?

Speaker 1

For example?

Speaker 3

Yeah, I'm constantly surprised by by by how tall or not tall people are when I first meet them in person. I realize I never get that right, Like my mental image is always off when they're like know someone for a few months, you know, but on only online that I see him in person for the first time, I always like, wow, yeah I was wrong about that. Yeah, I have you know, for synchronous and asynchronous is a really important thing that we're trying to get better at.

I have a test for this. I call it the facehle test. It goes like this, When there's a bunch of people and they're having a conversation and one person is moving their face hole a lot, like for minutes at a time, and no one else is moving theirs, then something's gone wrong. That that's not a conversation, that's a lecture, and it shouldn't be happening synchronously. If I am doing all the talking and other people are listening, they shouldn't be doing this in real time. I should

have recorded it. They can watch it when they want to watch it. They can watch it at you know, one point seven x speed. They can jump around, they don't have to take notes like it's just any kind of information transfer where it's primarily one person speaking for multiple minutes shouldn't be synchronous. Should be It should be asynchronous.

Synchronous communication should be what we're doing here, which we're having a conversation, you know, I move my face hole for a few minutes and then you go and it's like back and forth and then then okay, then that should be synchronous. But so much of what we used to do at work was we were having synchronous communications in a way where it really was just noledge transfer as one person at.

Speaker 4

A time, And we just don't do that anymore. And it's amazing.

Speaker 2

That does sound amazing now, I know that you like, Well, while a lot of people that work in a distributed fashion, they do work from home a lot of the time. But I've heard that you maybe work from home perhaps thirty percent of the time, So I want to know where else are you're working from.

Speaker 3

Yeah, I think this is a This is another big kind of misunderstanding. People think that distributed work means working from home.

Speaker 4

It doesn't.

Speaker 3

It meant working from home when we were all forced to do it, you know, with no preparation because of COVID. You know, we've had to work out of our apartments and homes with screaming children in an environment that wasn't set up for it. But distributed work means you can you can figure out where your environments are and you can pick. You can pick the work environment to best

accomplish whatever you're trying to accomplish. So I've got I've got a few different places, so I work from home some of the time, you know, about a third of the time. I have a nice like av setup. So if I'm like, like, for example, now I want to be on a good microphone, I've got a good setup at home, so I'll do that for my home studio. But sometimes I work from a museum. There's two amazing museums within walking distance of me. Without a ten minute walk.

I live in Benonville, Arkansas, and there's a museum called Crystal Bridges, which is just breathtaking. It's like thee I've ever been to. And you know, I can walk there in ten minutes, and I can walk around the grounds outside and inside, and it's amazing. Like whenever I need to puzzle puzzle through something, I go and I do it in the museum. Sometimes I go to the library and sit down there if I just want a breathtaking view with a lot of art. Sometimes I pace around.

Sometimes when I have co workers over, we go for a walk together, and it's an amazing environment for being creative, much better than like sitting in the conference room. And sometimes I work from There's a club that I joined which was a really nice pool and a gym, and so I'll go work at the club and if I feel like being around other people who aren't my employees,

just other you know, professional adults, sometimes that's useful. And then I can do like a couple of zoom calls in the club and then go go swim a few laps in the pool, and then you know, a half hour later, be back on a zoom call.

Speaker 4

Because there's nice showers and things there.

Speaker 3

And it turns out that like swimming laps in a nice pool is like the exact opposite of being in a zoom call, Like every sensation is the opposite of it is like the ultimate recharge. And I would never do this before. I could never before, like go for a swim in the middle of the day, because what I'd have to like drive to the gym and like they just wouldn't happen. But now I can work from there.

So this idea of like being able to choose where I want to be that I think is best for accomplishing whatever I want to accomplish over a few hours is kind of amazing. I'm never giving that up. And all of this is walking distance, so it's not so much walk work from home. It's really it's really walked to work, Like I just walk around everywhere for these places. And one hundred percent of my current lifestyle is accessible to everyone in our companies. Like it's not because I

have more money. It would have been the case if I had if I had this lifestyle in San Francisco. But you know, when I used to live in San Francisco, my my quality of living was much lower than it is now. But to the extent that it was okay, it was because I was spending a lot of money.

But now, like I think all of our employees can literally afford to live in the house that I'm currently living in and can afford to like be a member of this club and go to the same museums because it's all, you know, either free or inexpensive, because most of the world is when you're not forced to congregate in the same exact place as everybody else.

Speaker 2

I love the idea of walking around a museum when you're trying to puzzle through something. And something that always fascinates me about founder CEOs is that I always imagine this person who's a maker at heart that has had to find a way to also be a manager in terms of thinking about their diary or their calendar. And I'd love to know for you, how do you think about segmenting your calendar between maker versus manager activities that you're doing.

Speaker 3

So one thing I've done is I have canceled almost all of our like I said, synchronous update meetings, which freeze up many many hours a day for me. So I used to when I used to look at my calendar. What was I spending time on while I was having I was having fourteen fifteen synchronous meetings a day, and you know, fully half of those were just like one on ones, you know, catch up meetings, standing meetings with

various people. Get rid of our percent of those. Now, when when I need to exchange information, we exchange recordings asynchronously. That lets me lets everyone watch them anytime. I don't have to do it at a particular time, and much faster because it turns out everyone sounds better and it's actually more fun to watch at like one point five to two point zero speed rather than one x Like literally, it's just it's just true. So why would you Why would I want to watch someone updating me at the

same time they're speaking. Imagine if like when you're reading, imagine you're reading something, then you were forced to read at the same speed that the person who wrote it wrote. That don't make any sense. So we said I got rid of most of my synchronous stuff. That freed up probably two hours a day. When I need to have a synchronous conversation, I of course, you know, jump on a call. We have a synchronous conversation, but by then we're all in the same page. We're really having a

live discussion, so it's much better and much briefer. And then I don't waste any time commuting, so that's another like two hours a day, so you know, just pure calendar time. I've got four or five hours extra free time every single day that needs to be for which is kind of amazing. And I use that to you know, to be to be productive.

Speaker 1

Wow, that's amazing when you describe it like that.

Speaker 2

Now I want to talk about ever Note because I feel really privileged.

Speaker 1

To be talking to one of the people that actually created it.

Speaker 2

And I'm sitting here in front of my iMac and the only software applications that I've got open are Chrome because that's how I'm using Zancaster to record this interview.

Speaker 1

I've got Scrivener opened.

Speaker 2

Because I'm on a deadline for a manuscript that's due in under four weeks and I've.

Speaker 4

Strong strong choice scriven or strong choice.

Speaker 2

Oh, it's good, it's good. I just can't work out how to do the bloody.

Speaker 1

Reference list anyway.

Speaker 2

My problem, not yours, and ever Note is the other thing that's open, and I've used ever note for years and years and years. I can't remember a life where I didn't use ever note, and I wouldn't know. I feel, how are you using ebanote? What can you teach me about? How can I use abonoe better?

Speaker 3

So, yeah, I use it, I mean use it every day. Obviously it's great. I have become I think as I've like gotten older, I've become more selective about what kinds of things I put in there. So I used to put absolutely everything in there because I like it gave me this feeling of security that I wasn't forgetting anything.

And then I think as I've gotten older, I've like gotten to appreciate the feeling of security that I get from being okay and about forgetting things Like so, I just know there's likes of stuff I'm just not going to retain.

Speaker 4

I'm like that, that's cool. You know, I'll learn it again. I'll be happy.

Speaker 3

So I'm more intentional now, like I put things in every note that I tend to like have a higher confidence level that I'm going to need again that I'm going to want to you know that I'm going to want to use Whereas it used to be, you know, probably like I would probably look at two percent of the things that I wound up putting in EVERYNOE, and now I probably look at fifty to eighty percent of

the things that I wund up putting in there. So that's but that's that's more about like my lifestyle, like I just like care less about remembering, you know, every single scrap of information and more about using it for work, for organizing my thoughts, for organizing projects.

Speaker 4

And yeah, I use it.

Speaker 3

All the time, you know when when when I was and I haven't been at EVERYNOE for six seven years, so I can't can't take credit for for most of the new stuff.

Speaker 4

One of the things that we.

Speaker 3

Found when I was still there, which really explained a lot to me when we realized this from our research, was people who used Evernote for something that they loved, that they cared passionately about were much much, much much like more valuable power users than people who used it for things that they don't quite care about, like people who were like using every note at work because like their company like forced them to use it or something,

they didn't really care about the stuff they were putting in there. As totally makes sense in hindsight, but those were kind of you know, lacksadaisical users, whereas people who were using it for their like life's work, for the things that are most important to them were like really power users were really in love with it. And you know, we figured we had lots of data to kind of

back this up. But the thing that made it really clear to me is I was talking to a pretty good friend of mine who had, you know, I'd known for many years already had ever Note, and he said one to me one day, a you know, like i'd been using every note for like three or four years now, because you know, you started, and I figured, yeah, I'll try it out. And I used it a bunch and use it a work, and I never're like I was never that into it. Like it was fine, but it

was never like that into it. And then I like decided that I was going to write a book, and I started using it to like collect ideas for the book. And then I like understood how amazing it was because I was finally using it for like the most important thing in the world, tree and I couldn't I couldn't put it down, and I thought that was like a really beautiful thing. Like make a product that if you use it for something you really care about, it's amazing. And maybe've been trying to recapture.

Speaker 4

Some of that.

Speaker 2

And so we will be back with Phil shortly where he'll be talking about the rule of three and ten for business and how this was life changing, and we'll also hear from Phil about the difference between difficult versus unpleasant decisions and why it's critical that you make that distinction. Now, if you are after more content, you might want to follow me on the socials, where I.

Speaker 1

Produced quite a lot of content.

Speaker 2

The two best places to follow me are on LinkedIn just search for my name Amantha Imba. I think I'm the only one on there, and also on Instagram, which I'm starting to post a lot more content too, And you can find me on Insta at Amantha. I something I have never really used religiously in ever, note firstly having different notebooks, like everything sits in my inbox, and I haven't relied too heavily on tags, and like, am I missing something really major?

Speaker 1

There? Should I be chain? How I use epanos?

Speaker 4

Well, you know.

Speaker 3

I'm similar, So I have notebooks, but you know I probably have like fifty notebooks but realistically, I only use like four or five on a regular basis, and I barely ever use tags. I mostly just search for things.

Speaker 4

And it worked great for me.

Speaker 3

Because usually, like I can just type in a few letters and I can find whatever I'm looking for.

Speaker 4

I'm gonna find, you know, I'll get it down.

Speaker 3

To like ten, and then when there's like ten notes, I just like the last mile of the search, I just see the one I want, right, so I can just like click on this. I don't have to get it like exactly right. So I don't use most of that stuff either, but there's a lot of people who religiously use it. What we found is that there's a group of people who I think are like organizational fetishists. Like they enjoy they derive pleasure from the act of

organizing something. They like putting labels on things and putting things into little cupboards and stacking things up cleanly.

Speaker 4

There's people like this, I get it. That's cool.

Speaker 3

They're in to the organization for the sake of the organization. They enjoy it, and that's probably I don't know, five percent of the population. And they and these people have like all sorts of you know, cultish things. There's like getting things done people, and there's all sorts of like different warring camps about how are properly organized things and what taxonomies they want. And I'm not like that. I

don't enjoy the act of organizing. I just want to have the benefits of it without actually doing the work. It's not actually clear to me that like, well organized people are inherently more productive than disorganized people. I am fundamentally disorganized them in normal life, but I'm pretty productive. But that's I guess one of the reasons why we were so interested in ever note is like I wanted to have the benefit of having this organizational fetish without

actually liking organizing things. So yeah, I just throw everything in there and it you know, and it kind of works out. But there's a there's a very hardcore user base that loves, you know, nest the tags and multiple notebooks and flags of different colors, and we were constantly getting bombarded with requests for additional taxonomies, additional ways of organizing for people who are into the organizing.

Speaker 2

Now, given you describe yourself as being more on the disorganized side of things, how do you organize your task list and just what your priorities are on a daily, weekly, monthly basis.

Speaker 3

So you know, I've never actually succeeded in keeping a to do list a task lisk. I don't have one, like I've obviously tried all of them. We have them, I never note, I just don't use one. I was actually going to start at one point, I was going to start a company. Most of my company ideas are jokes. So if someone actually wants to build this, by all means, please build that, I'll be a customer. I wanted to start a task manager to do you know list that was called too done or too did, And the way

it would work is there'd be no input. So I would start this program, this app, and it would figure out what I did just by looking at like my calendar where I've been, and it would like it would automatically put items that I'd already done and check them off.

Speaker 4

So I would look.

Speaker 3

At it and it would say, like watch Netflix for two hours, check done, went swimming, check done, and that was it. I would just look at it. The only way the only thing you can do is look at it, and I would just tell you if you already did, and then you can be like Yep, that's what I did, and you like feel a sense of accomplishment as if you would like planned it, but it didn't really happen. But I don't do that ahead of time. I generally I live off my calendar. So I do have a

pretty well organized calendar. But that's because I have Leah was my assistant, who does an amazing job and keeping keeping the calendar organized. That's like my single source of truth. I wake up in the morning, I look at my calendar. I do what my calendar tells me to do. I don't question it.

Speaker 4

Uh.

Speaker 3

And but in terms of like the kinds of topics and things I'm working on, look, if they're not important enough for me to remember, they're probably not really important enough to do.

Speaker 1

That's such an interesting way of thinking about things.

Speaker 2

Now, I've heard you talk about the rule of three and ten and how life changing that was for you. Can you tell me a bit more about the rule of three and ten?

Speaker 3

Yeah, So this is something that one of my one of my friends and really one of my best mentors, is a guy named a Mickey Harusha mccattuaney son. Mcatony son is the founder and CEO of Rakuten which is, you know, started in Japan, but now it's a big global internet company and he was, you know, the first employee and now it's I don't know, hundred thousand employees and he's still the CEO. He's one of the most amazing people that actually is like the best CEO from

one person to tens of thousands of people. And he came up with this rule of three and ten, which basically says that every time something important triples, everything breaks. So every time in your company something important triples, everything breaks. So the idea is like, let's say, you know, you

start a company and it's just you. You're the only person there, kind of figure out how to work, and then you like hire one more person and things are okay, and then you hire a third person and now it's tripled and everything's broken. So now you got to like reconfigure everything. So you figure all that stuff out and then four, five, six is all fine. But then you hire the tenth person, everything breaks again. So it's three and ten ten because it's just easier than keeping multiplying

by three. Nothing magic about ten because you'd be nine, I guess, but three and ten is easier to remember and then you know, you figure it out for ten people, and then it breaks again to thirty, and then it breaks it one hundred, and then it breaks it three hundred. And by it I mean like everything, like how you communicate, how you pay people, how you keep your calendar, what kind of office setup you have if you have an office like it all, like every time you triple something

important and tripling. The easiest thing is tripling headcount, tripling in place, but it could also been tripling the number of customers, tripling the amount of revenue, like you know, tripling the number of products that you have. Every substantive tripling puts extreme strain on all of your systems, and it's worth looking at them and anticipating it. And a lot of startups go through multiple triplings without noticing it.

So like right now at we're at about we're getting close to a hundred people, right about one hundred people. Probably by the time this podcast there is will be a little over one hundred people. But you know, but we still have certain systems. You're only a year old, so we probably have some systems that we put in place when we were three people, and so we've missed now several triplings because we missed like three to ten,

ten to thirty thirty tow one hundred. So those things are like way out of date and they need to be refreshed. So a lot of startups get into trouble when they kind of blow through a few triplings and then things start to creak and things start to break. The flip side of that is a lot of big companies waste a lot of time trying to be quote unquote innovative when they really don't have to. Like, you know, if you're a ten thousand person company, like you're good

until you hit thirty thousand people. You don't need to like figure out too much stuff. But you know it's hard then that may take a decade, but it's hard to like sit around for a decade without changing things. So big companies tend to chase innovation and change a little bit too much, and small companies tend to forget about it and break things. So I just try to be mindful of that.

Speaker 2

Now, for people that are working as a manager, why is it important to learn the difference between difficult and unpleasant decisions?

Speaker 4

Ah?

Speaker 3

Yeah, I think that's a good's that's like that's probably one of my favorite kind of things that I've I've that I've learned, that I've figured out about myself. I found that whenever I think, oh man, that's a really hard decision, Like that's a hard decision. Whenever that happens, whenever I feel like something is a hard decision, I like a little red flag goes off and I ask myself, is it hard like it's difficult to know what the right answer is? Or is it hard like it's unpleasant?

And usually the vast majority of time, when I force myself I think through that, I'm like, oh, yeah, I know what the right answer is.

Speaker 4

Is just unpleasant.

Speaker 3

So probably ninety percent of the decisions that I perceive as quote unquote hard, they're not actually difficult to know what the right answer is. I know what the right answer is. They're just unpleasant, they're scary. There's something about them that that's bad. And once I kind of identify which one it is, then then things become clear, not easy, but clear. Obviously, if a decision is unpleasant, you should still do the right thing regardless of whether it's pleasant

or unpleasant. You just have to deal with the unpleasantness. But I think what I used to do is really conflate those two things. And I think a lot of people conflate that. I think a lot of people conflate difficult decisions with unpleasant decisions, and they pretend that it's hard to know what the right answer is when really it's just an unpleasant answer.

Speaker 4

Uh.

Speaker 3

And yeah, that's that's like a that's probably my favorite.

Speaker 4

Like management hack or life hack. It's just like something's a hard decision, hard how.

Speaker 2

And when you have an unpleasant decision to action, how do you approach that conversation?

Speaker 4

Uh? I mean it's very situation right.

Speaker 3

It depends on what's what's unpleasant about it and how, and but ultimately you just you have to do the right thing and you have to do the right thing. Like I very much dislike words like fearless. I think for a while it seems to be receding, it seems to be in remission. But for a while, like a few years ago, everyone was like something something fearless, something something.

Speaker 4

It was like it was way overused word.

Speaker 3

And I think fearless is really like people. Fearless people are just genuinely stupid. They really don't have any fear. Then they're clearly too dumb to understand what the danger is. I never try to be fearless. Being brave is about experiencing fear. Like if you're not afraid, you're not brave,

you're just dumb. So you have to, you know, you experience the fear and the trepidation, and you allow yourself to experience and you just do the thing that you have to do anyway, because that's the right thing to do. It's not easy, but it's simple.

Speaker 2

Now, on the topic of management hacks, and I'm not sure if this falls under that category, but I've heard that you always try to be the positive voice in a conversation.

Speaker 1

Can you tell me a bit about that.

Speaker 3

It's not so much that I try to be the positive voice. It's that there's there's a strong negativity bias in people. Kind of cognitively, I have it. Almost everyone has it, where basically it's easier to seem smart if you're being negative. And this is especially true in social situations.

So you know, if you've got a bunch of people sitting around and you you ask for someone's opinion, they're kind of trying to seem smart and thoughtful in front of everyone else, and it's much easier to do that by pointing out the weakness, by pointing out the problems, by pointing out the risks. It's just just how our brains are wired. And then you know, the next person has to like top the first person and being like

negative and afraid and so on. So typically, like decisions are overwhelmingly weighed towards towards negative, towards the safest option, the least bad option, not the most good option. And this is you know, there's evolutionary biology for this. There's like very basic brain science about this. You know, it used to be thought that the amigdala the portion of your brain. This is wrong and overly simplified, but still useful, The portion of your brain that's basically in charge of

fight or flight responses. That's very old in evolutionary terms.

It exists in almost all animals. And then there's like a much more recent human part of the brain that deals with you know, opportunity and like happiness and love and strategy, and that's that's in evolutionary terms, that's brand new and very very weak compared to the power of the of the dark side, of the fear and the negative and the risk aversion and so when you're making a decision, it's useful to understand is this the type of decision where it's important to pick the least bad option,

or is this the type of decision where it's important to pick the most good option? Understanding that least bad and most good are often the same. They are often the same the same thing. Like something could be the most good if it works, but also the most dangerous or the most.

Speaker 4

Bad if if it doesn't work.

Speaker 3

So you just got to know, like are you going for least bad or are you going for most good?

Speaker 4

And you know, if you're one.

Speaker 3

Hundred thousand years ago, you know, one of our caveman ancestors, and you're standing in the middle of a you know, a grassy plane and you think you're saw a tiger hiding in the grass. That's like the part of your brain that's like meant you know, to do that, and you're thinking like, well, should I go into that grass?

Speaker 4

Maybe there's a tiger there?

Speaker 3

Then yeah, maybe this is a type of decisions where you should take the least bad outcome, which is like, you know, do everything possible to avoid being eaten by a tiger. But if you're like running a startup and you're not about to get eaten by a tiger, and you're trying to decide about a particular you know, what to name your product or whether or not to put in a feature, then like, maybe the downside is pretty limited because like I can be eaten by a tiger

regardless of how you decide. So you may as well make the decision based on what's most good. And you can't do that if you allow any any focus on the negatives and the downsides, because then then the lizard brain, the amigdal a portion of your brain is going to kick in and you're gonna you're gonna.

Speaker 4

Buyas towards risk version.

Speaker 3

So when we're making decisions where it's important to get the most good, not not the least bad, I basically try to discourage anyone from saying anything negative, not out of some poly sense of like I only want to hear good things, but because I don't want people's brains shut off. So often I'll say, like, okay, I only

want to hear what can go right. I only want to hear the good stuff intentionally as an exercise, as a meditation, because I don't want anyone to like start that cycle of being like, oh, but if.

Speaker 4

We screw it up, maybe we get eaten by a tiger. Which doesn't mean we don't look at the risks. Of course we do.

Speaker 3

We just we just try to separate those two things out and look at them look at them separately.

Speaker 4

But in startup life.

Speaker 3

There's many, many, many, many, many many decisions where it's more important to be the most good, not the least bad.

Speaker 2

Now, Phil, for people that want to connect with you and try out the wonderful things that you are putting out into this earth, what is the best way for people to do that?

Speaker 3

Well, you can send me an email, but I do have one hundred and you know other messages. Lay response is tough, but yeah, you know Twitter, I'm at P libbin, p L I B I N or that app or al turtle dot com. Really, any of those are ways to get in touch. And I am happy to happy to chat anytime.

Speaker 2

Amazing, Phil, it's just been such a privileged chatting to you. Your products have just made my life so much better. So thank you for the work that you've done.

Speaker 3

Well, thank you so much. It's extremely kind of you and really fun to chat.

Speaker 1

Hello there. I hope you liked my chat with Phil.

Speaker 2

And if you know someone that you think would find it really useful, why not share this episode with them. How I Work is produced by Inventium with production support from Dead Set Studios. The producer for this episode was Jenna Cooda, and thank you to Martin Nimba who is the audio mix for every episode and makes all of this sound much better than it would have otherwise.

Speaker 1

See you next time.

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