Speak Easy

Jon Lee, CEO at Work From Anywhere
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[00:00:00]

Tyler Sellhorn: Hello, everyone. My name is Tyler Sellhorn and welcome to another episode of Speak Easy, the podcast where we discuss communication, productivity systems, capturing our thoughts, and how we share those thoughts with our future selves and others. We believe that managing our brains is core to 21st century work, and we're here to learn how to do it better than we did yesterday.

Thanks so much for listening. Speak Easy is brought to you by Cleft. The easiest way to collect your thoughts with our cross platform applications. You can simply capture your ideas wherever you are and paste them where they belong later. Today, we are blessed to be learning out loud with John Lee. John is the co founder and CEO of Work From Anywhere. Work From Anywhere is a compliance platform To allow companies to provide international work workcations as a benefit. John speaks six languages and has traveled to over 60 countries. In the last 20 years, he has lived in Ireland, Germany, the Netherlands, Thailand, and Portugal. His previous startup CultureMee centered on intercultural communication and won best travel technology product at the Global Youth Travel Awards in 2018.

Prior [00:01:00] to CultureMee, John held senior finance roles at FTSE listed CRH PLC while working there, he traveled to over 150 over a 10 year period and got to see firsthand the challenges of dealing with complex corporate tax, individual tax, and employment law across multiple jurisdictions. Okay, John. We're so excited to be here learning out loud with you. Give us a through line there when we're saying super traveler trying to sort out tax stuff and you're experiencing this problem around intercultural communication and now you're doing back to corporate taxes.

You give us some stories there. Give it, give us the narrative, please.

John Lee: I suppose one word it probably comes back to is curiosity. So for me, I was always curious. I was always curious about the world, about other people, about other cultures, about other countries. And I got so much energy from going, visiting different parts of the world and seeing how people communicate, how they [00:02:00] behave, how they live.

And for me, that drove a huge amount of my own curiosity, which then led me getting involved in essentially to travel or global startups, whatever way you want to call it. But both of them involving an awful lot of touch points across other people, other cultures, but that, that, for me, that curiosity for travel and other cultures has started from a very young age.

Tyler Sellhorn: Interesting. Okay. When you started okay, you had this experience of traveling and being energized by being among people that maybe didn't grow up like you or communicate like you, how do you bridge the divide between yourself and others who are like you? Don't look like you don't speak like you.

You've obviously learned some languages along the way. Tell me more about that experience is like of being someone who's in a new place, trying to communicate with people that don't speak even the same language as you help us get better at that.

John Lee: Funny enough, it actually comes [00:03:00] back to my first word, having a kind of a curious mindset. So for me, when I was working with people from different cultures and going, living in different countries. I've always really tried to make a big effort to learn the local language and try and find a bridge to connect with them.

And even if I didn't speak the local language, you know, 90 percent of our communication is nonverbal. So finding ways to even speak to people in nonverbal gestures. Yeah. And so I think trying to have that humility inside you and that curiosity to try and. Find ways to connect with people. But for me, that's one of the reasons why I put so much effort into learning different languages, because I got such a kick out of deeply connecting with people and it's really interesting when you're learning a language.

It's really not until you can start to tell jokes in that language and understand those jokes that you really start to get that magical part where you can really deeply connect with the soul of other people in lots of ways. And for me, I, that whole journey and the difficulty of learning a language and getting to [00:04:00] that point, when you get there and you're able to really deeply connect with people, it's amazing.

I'll give you one anecdote. When I was in CRH, I used to work in internal audit. And we would go and visit all these operations around the world, and we would go to look at manufacturing sites, distribution sites. And when I was, for example, in France or Switzerland or Germany, I would go there and I would speak the local language and my other colleagues would have had translators and translators translating for them at every single audit.

I used to go into. I used to spend. The first 10 minutes really connecting with the, let's say, plant manager. And I say to him, after 10, 15, 20 minutes, listen, tell me how you run your business. What are the things you're trying to improve or whatnot? And then they give me a list of about a hundred things they're trying to improve.

So I'd have my audit report done after half an hour. And my colleagues who were dealing with the translator, They were really struggling to get up all their audit points was for me. I had them all done because I had the language. I was able to deeply connect. [00:05:00] And of course, that's just from a professional standpoint.

There was lots of other benefits from learning the language as well.

Tyler Sellhorn: Okay so I'm putting a pin in like a trillion things in your answer you just gave, but I have to ask because, John and I have been internet friends for a very long time. We met in a Hopin instant networking thing at a GitLab like event, like back in 2020, probably. And I think it's so interesting to hear you doing the work of how can I communicate in a way that, Loosens up this person that is maybe even afraid of this audit, right?

By learning the language well enough to tell jokes. So my question is, because I know enough about you to ask, right, how are you doing with your jokes in Portuguese?

John Lee: Well, this is something I am deeply, deeply embarrassed by because I think the challenge of building a startup and three kids below seven. Has [00:06:00] made it a bit of a challenge to get to the right level of Portuguese. I do speak some Portuguese, but I'm nowhere near the level I should be at considering my capabilities.

So it's definitely

Tyler Sellhorn: please

John Lee: an improvement point.

Tyler Sellhorn: because I can only tell jokes in English. Um, uh, more power to you for you being able to speak Thai jokes and among other languages as well. So yes, please don't be embarrassed. I will take all of that embarrassment and hold all of it for both of us. Okay, let's go back to that moment where you're about to like, like connect with a person that like is going to receive an audit from CRH, right? do you think about communicating with that person? You have a set of processes and like audit statements that need to have filled in blanks, right? And what is it that you're trying to do to open them up to be able to have a conversation that's real and Connected and you're able to communicate well.[00:07:00]

John Lee: Yeah it's a very good question for me. So much of it came down to trying to get to know the person, because if you think of how we live life today, everything is so busy, everyone's in a hurry. Everyone's calendars are full and. There's no time for hardly anything, but actually, all the more reason, if you do take the time to really deeply connect with somebody, no matter how busy you are, and really try to get to know them, and I don't mean just professionally, I mean outside of work, that really goes a long way, and also to try and understand and have that curiosity for the culture.

And I give you two very simple examples in the Netherlands when they have lunch, they actually spend like they give you in a lot of cases when I was there, here's your sandwiches, make your sandwich. They spent 20 minutes eating a functional lunch and they get to know people very often in the meeting room.

In France, certainly around Paris when I did a lot of work there, that's not how it works. They have an hour and a half to two hour lunch. They'll very often be a glass or two of wine and a three course meal where they really want to get to know [00:08:00] you. Yeah. And it's not so much in the meeting room.

It's really outside the meeting room at lunch. So trying to have the humility to know, well, I need to wait and see how this culture is and how people operate. And the national culture is one aspect of it. It's also the individuals. It's also the individual personality and the different subcultures that go around it.

It could be their sports teams. We were very passionate about, for example, sports. So trying to find those connectors, those similarities, and just trying to get that, get to know somebody. First and foremost, really goes a long way. Then once you get to know them and they see what you're like then it's much easier to go into the next step.

Tyler Sellhorn: it's very obvious to me who John is and how that experience, those experiences translated into I think there's something here, here. I want to build a business around this experience of the cultural gaps that, that exist. Even just having the awareness that it's a long lunch away from the office building in France versus, sandwiches. In, in the meeting room, right? It's a working [00:09:00] lunch and you have the conversation, when you're in Amsterdam or wherever you are in the Netherlands, right? I think that's so like obvious. to me and maybe to you, John, but that clearly isn't obvious to everybody. Cause you helped, you built a business around that.

And how do we get more people to embrace this idea that who I'm communicating with is probably more important than what it is that I'm even trying to communicate.

John Lee: I think you've hit the nail on the head and it's trying to find multiple different ways of communicating with somebody is also important because you very often see somebody the way they write an email might be different how they write a Slack message, might be different to how they do an audio recording, might be different to how they are in person.

And I think having An understanding of how somebody wants to be communicated to is also really important. Some people get frustrated if you send them a voice message, for example, whereas others prefer writing, whereas others [00:10:00] might be the other way around.

Tyler Sellhorn: out. That's, that is, Actually, what we are trying to do at cleft because we are voiced to text people, right? Because we understand that so many people do not want to hear our voice note, right?

John Lee: Yeah.

Tyler Sellhorn: That is so important to like, recognize who is the receiver of this message and how would they like to be communicated with?

John Lee: But this is it. Even when we were doing the preparation for the show notes, I was able to do a voice note. I prefer to doing voice notes. So I don't like spending ages writing on notes. So the fact that I could transcribe it for me, that's really, that's one of the things I loved about it. So exactly that. If you take that dimension, there's also, so there's the form of how we communicate. Yeah. But then there's the, let's say, cultural nuances around how we communicate, which can be national culture or other elements of a sub national there's so many, even like company culture there's so many nuances.

When you think of culture, people think one thing, but there's so many multiple dimensions to it. And again, going back to really trying to ask people, how do you like to be communicating to, what are the nuances? What are the do's and [00:11:00] don'ts? And I also do believe, again, I'm very big on remote work, but I'm also very big on those moments where we get to connect in person as well.

They're also so powerful as well. They were for me when I was working in CRH. I've really made an effort to at least, once or twice a year, get to meet people in person. And then once I did, then it really cemented the relationship.

Tyler Sellhorn: Well, I know for myself, like we've, long been internet friends, but we've also been in real life friends too, right? That URL to IRL pipeline is indeed existent, right? We've met in Lisbon, right? Like we've,

John Lee: That's right.

Tyler Sellhorn: a hug. We've had those moments of actually looking at each other eyeball to eyeball instead of just screen to screen. And I think those it's both, it's all the above. It's not either or, and there's trade offs to being a primarily virtual relationship. And obviously there's value to being together. But it's okay, is that going to be every day?

Is that going to be every week? Is that going to be every quarter? How, you mentioned, having it once a year. And so I guess maybe thing that I'm hearing you say. Okay. that one of the ways to peel back the [00:12:00] layers and like you said, dimensions is to just ask that other person, like how they prefer to be communicated with, I guess, maybe I'm curious do you have any tips for us of like, how to ask that in a disarming way? Cause sometimes like expressing preferences and don't send me this and please send me that is, is vulnerable, right? How do we help people have a little more courage with us to share how they like to be communicated with?

John Lee: Yeah, that is a, that's a tricky one. I think certainly from internally in companies, they like to have internal wikis or how to, or, you know, about me, I think They're very very powerful. I think the other thing that's also really helpful is having, practicing a really strong level of emotional intelligence so that you're very attuned to how the other people are reacting.

And what I mean by that is that there's a great saying in Japan about reading the air, it's a great book by Erin Meyer it's very much focusing on organizational culture. She's written multiple books. Books on this and she talks about how in Japan, they talk [00:13:00] about reading the air and what that means is that reading the atmosphere, the tone, reading what's not being said that the face gestures, for example, sometimes in other cultures, the smallest face gesture can give the biggest signal, but if you're not attuned to it, if you're not looking for it, if you're not listening for it, then you're going to miss it.

And so for a lot of people from different countries, we maybe are not attuned to be as aware of that as maybe we should be. So practicing that hyper awareness can be a really big superpower for for not just doing people from different cultures, but also just dealing with people from different types of personalities, individuals, you know?

Tyler Sellhorn: Okay. So what does your about me page say? What's give us some examples of like how you would express that for yourself.

John Lee: Yeah, it will tell you that someone like me, I'm I'm very fast paced. I go a million miles an hour. I have a big heart. I'm somebody that, strives for the very best for [00:14:00] myself on the team very loyal and deeply curious about the world. I mean, for me, I think they would be the things that would be, that would probably jump out.

Tyler Sellhorn: I know that I appreciate your speed and your big heart. And your loyalty. I obviously have observed you over time, like striving to be the best you can be. So thank you for being you and expressing that. I'm curious to learn about you have this experience of now translating those experiences into a new business that is really centered around, workations as an employee benefit for companies. What are you seeing from the outcomes that are coming from those? workations that are happening. Obviously you did that for yourself, like when you were like just traveling for business. But now there's this like longer term stays that are like, not in your home country

John Lee: Yeah,

Tyler Sellhorn: what are you seeing happening around, [00:15:00] just the benefit for the company, but also like for those individuals that are taking the trips.

John Lee: well, I think one of the two things that probably jumped out is that first of all, initially, when people heard work from anywhere and requested work from anywhere from, their bosses or from their HR team, they were thinking, Oh, work from anywhere means we can work from wherever we want. But I think now there's a realization amongst the vast majority of people that, okay, well, there's obviously limits, there's limits in visa sanctions.

I mean, I don't see too many Instagram photos from North Korea, for example. So I think the first thing is there's a recognition that. Companies themselves and employees recognize this, that there needs to be some degree of controller limitations on it. The second aspect that's interesting is why people are going on work from anywhere locations and whatnot.

There was clearly a lot of pure of laptops by the beach, people having margaritas in Mexico. And that was in the mindset of a lot of people, but actually what we've seen in practice from speaking to a lot of the Fortune 500 companies [00:16:00] that we work with is it's actually even more so about take, for example, an Indian employee who's got, they're based in the US and they have a sick grandparents and they want to go and spend a couple of weeks with them.

And maybe they're about, maybe they're dying and they want to spend those couple of really special weeks or months with them and they're getting, they're sending these requests saying, look, I want to be able to work from there. It's only going to be for a few weeks or months. Can I do this? And what's really interesting is I think a lot of companies now are really recognizing how valuable this kind of thing can be as an employee benefit, which is completely separate from their domestic remote work policy, which could be fully remote or fully in office, or I would put it where they want.

But if you can offer this as a benefit, what we are seeing, particularly in the U S is that in the U S, for example, they typically have 10 to 15 days PTO. But if you can offer 30 to 60 days work for money, or for these kind of cases, it can be really powerful. And we could see, for example, if you look at the metrics.

It really does [00:17:00] pay off for the companies that are willing to take an acceptable level of risk.

Tyler Sellhorn: Yeah I'm wondering about. That story that you shared of someone who is returning home maybe is in a major metro and is going back for myself who lives in a tertiary city in the United States. Fort Wayne, Indiana. Why I'm so excited about distributed working.

And working at places like and other places like this is not my single meal ticket here. In fact, it's not paying for any meals, but or yet they'll say it that way. I think that there's this advantage to like companies co creating better lives for people. Um, like the way that the company is operating like you're talking about, like tax compliance, right? That's obviously not very related to someone visiting a sick grandparent. However, like those constraints, right? If we can [00:18:00] build a, like a global superstructure to we should be paying our taxes. right? But we also shouldn't be limited to be able to visit a sick grandparent that just happens to be in the wrong jurisdiction.

John Lee: This is exactly, yeah, it's one of the things we could find. That's why I did, you know, that's why I was inspired when we started this journey at Work From Anywhere is we could see that, and I had the lived experience of that digital nomad lifestyle working in different countries, how liberating it was.

And yeah, seeing these wonderful different cultures spending. A couple of months in Thailand, for example, and traveling all around or even around New York, for example, it was just exhilarating experience to have that with my wife, Dee, and her daughter, Rosa. And for me, when we started working for Manure, I could see that taxes was coming up again, and again, as the biggest blocker, they elephant in the room for a lot of companies that said, I'm not comfortable.

I remember walking into, a big pharmaceutical company back in [00:19:00] 20, back in 2021. And I said, this is where the world is going. This will be a big employee benefit. And they all laughed me out of it. They said, you must be joking. There's no way this is going to be a benefit because of taxes.

So that kind of gave me, I also work as a little bit of a chip on the shoulder. I said to myself, I really believe this will be something. And I want to actually challenge the assumption. That taxes has to be a major barrier and nobody was really looking after this space the way the vision that we had.

And that's where it all went from there. And. Even, you know, it was funny, even I would say even like a year ago, even a lot of companies, even then, or I'm still not convinced, whereas I think now a lot of companies are actually recognizing, okay, there are ways to give some degree of flexibility without completely leaving yourself open to risk.

And of course, that's where, the technology does certainly in a lot of cases come in very helpful, whether it's what we're doing at work from anywhere or the different companies in our space. But the bottom line is there are answers there, whether they're looking for an oil tank or technology solution [00:20:00] or a plug and play, whatever it is, there's great solutions out there to help companies be able to offer this and to have that powerful impact of what you can do for employees when you do offer them some degree of international service remote work flexibility.

Tyler Sellhorn: Okay? So we've zoomed out. I wanna zoom in to just you, John, and your brain, right? When you have new thoughts about expanding workation to a new country, or you've got a new marketing thought, or a new sales playbook, or, like when you're starting that new idea. What do you do?

How do you capture that thought? What, how does it get out, out of your brain and into something that someone else can look at and touch?

John Lee: I'm probably a bit of a disorganized mess in that, depending if it's something that's really important strategic components, I might write it off in a Microsoft let's say not Microsoft, in a Google doc, for example, if it is like a tactical thing that we can do, we might have Slack channels that might work in it and other times, I might [00:21:00] put in a to do list and a particular component of my Google calendar where I have a specific topic locked away. Yeah, it is a bit, it is a little bit of a struggle and it's probably something I could get a bit more disciplined at doing a bit better. If I'm honest.

Tyler Sellhorn: we're selling you here on the podcast. Then we would like for you to give cleft to try you. You'd like sending me the note, getting ready for

John Lee: I did.

Tyler Sellhorn: And, uh,

John Lee: I did. I did indeed. I definitely will be. I've already started using actually enjoying it. So you're a good salesman.

Tyler Sellhorn: fantastic, John. Okay. So I guess maybe I'm curious then, like, how do you connect those initial ideas into the rest of your system? You got some things happening at work from anywhere that got that initial idea. How does it migrate into where it can be, iterated on and get better.

Okay.

John Lee: So we basically have kind of pipelines of different topics that we have set up in in a few different formats, basically. It's very much, we have a team of talent for different topics, be it a chief marketing officer, CTO my co founder don't looking after a product [00:22:00] piece of it.

And what happens then is we have regular games is where we review, okay, what are the priorities? What are the topics? What are we looking to do? Basically and we find we just like to, at the moment, we very much leave it to those different leaders. What works best for them, basically, but we do collect and have the interaction, the chat on slack on a regular basis.

So that we're able to feed into the priorities. And then have I would say calls once once a week, once a fortnight on particular topics to try and dive into them further.

Tyler Sellhorn: Can you give us a little bit more detail about specifically about your company and like how many people are working together on things and where does the mind meld happen, like between people and that, that sort of stuff.

John Lee: Yeah. So we have a team as you can imagine, fully distributed and we have a mixture of of core talent, but also fractional talent that we use. We have talent in, in UK in Australia, in Portugal and Sri Lanka and the Philippines and a few different places around the world, basically.

Yeah. Absolutely. And it really depends. [00:23:00] So it depends on what the topics are. For example, we have for argument's sake, the QC testers, they're testing all the time and it's very clear what they need to do. And they don't need regular updates for us. Maybe for example, my chief marketing officer, I'm catching up with on a practically a daily basis, for example.

There's a lot of things going on there. So it depends on, on, on the function, depends what's going on. They go through different waves. I would say sometimes the technology piece of it, there's a lot of enhancements and there's a regular cadence of meetings, maybe on the products, product brainstorming or product feedback, especially when we're speaking to clients, there might be intense phases there where it's a, it's very, very intense.

And really depends like in the next couple of weeks now, my, on my side, I'm actually traveling to London a couple of times. I'm going to Paris and Budapest. So for me, I'm on the road now. So again, a lot of the time it is quite, we leverage async all the time for us. Async is really, really important to help work around what, what works best for the team because we're so distributed around the world.

Tyler Sellhorn: maybe that's what I want to invite [00:24:00] you to conclude for us with is give us a sense of you as someone who is building a product that enables people to move location and work, right? You're talking about travel coming up for you. You're not going to be in your regular home office. Like, how do you stay, you mentioned asynchronous work in ways that people can get, at any time, they don't have to be on a video conference with you or in the same office. Help us to like, end off our thoughts here with a way to think about being a CEO, being a business owner. In a way that allows people to access you and your brain even without you being there with your presence.

John Lee: As a CEO, the power of async is really is absolutely amazing. And that's probably been the one, the biggest hack for me, but the other side of it is the power of also switching off. I will say job under Ford from remote. He shared a really good tool called oval, which I started using, which basically completely shuts off different things like social media or different apps or things that can be a distraction.

And [00:25:00] that's also been absolutely, for me, a really wonderful tool, knowing when and how to shut off and having greater control of that. And the biggest thing for me as a CEO to enable a high performance for me as a CEO, I need to be really connected with my family. So for me, if I'm doing that and having the time with them and knowing when to switch off at the weekend as well, I will be 10 times more productive, the next week in work or the next day or whatever it might be, for example.

So I've read a story recently that remote work makes you a better dad. And I've really found that. I really have found it. So for me, I think actually funny enough, it's a lot of the personal side, those aspects of, grounding myself and taking that time to make sure you don't burn out and things like that.

And, close to your tight knit family. That's what gives me the rocket ship to be the best that can be with me, with myself and with the team.

Tyler Sellhorn: Well, thank you for that invitation to turn off work and turn on family to be integrated in our lives, right? You're speaking the magic words for Tyler, right? You're going to bring out my identity stack, right? I am a parent. I am a spouse, [00:26:00] right? I'm a youth sports coach. We're talking on a Friday. We're getting ready for the Snider Panthers to go beat the Carroll Chargers. Uh, like, like, obviously these are not things that are relevant to our conversation, but those are who I am even when I am on as a worker. Really exciting to be invited into that space again to become the best we can be for all of our different identities.

Thank you, John.

John Lee: Thank you so much, Tyler. It was a pleasure being on.

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