Podcast S2/E1: Interview with Kyle Ladewig, CEO of Out of Office

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In this episode, Alex talks to Kyle Ladewig of Out Of Office, a company that facilitates working groups for remote workers and freelancers. These are intended to replace that important social interaction people would usually get from an office environment. 

Kyle discusses how his business has moved online as a result of the Covid-19 pandemic, provides some tips for managing remote teams and hiring the right people, and also recommends some productivity techniques that will be helpful to anybody working from home. 

Included in this podcast:

  • An introduction to Kyle (1:10)
  • Remote work and mental health (4:16)
  • How Work Club works (9:18)
  • A discussion on running a remote team (15.53)
  • Tips for productivity (17:45)

Supplementary Links and Information

Full Transcription

We have edited some repeat words and unclear sections to enhance readability.

ALEX: Welcome to the HomeWorkingClub podcast. I’m Alex and I have a special guest today, Kyle Ladewig, CEO and founder of Out of Office. Hello, Kyle. How are you?

KYLE: Good morning. Well, good evening to you, but good morning where I’m from in San Francisco.

ALEX: Fantastic. We’re recording from the UK to San Francisco at the moment through the magic of Zoom.

And again, as we’re saying at the moment, as everybody’s used to due to the global situation, if there are any technical difficulties, please forgive us for that. We’re not able to be in the same room, much as I’m sure we’d like to be. I’d certainly like to be in San Francisco.

KYLE: Yeah, well we’d love to have you here.

ALEX: Good stuff. So today we’re… Kyle’s obviously been a huge mover in the world of home-working and freelancing for a long time, setting up Out of Office in 2011, I believe, was it Kyle?

KYLE: Well, not that old, 2018.

ALEX: 2018. I’m putting years on you, I apologise. Out of Office has Work Club and Work Space, and we’ll talk a little bit about Kyle’s journey in a minute. But one stat that absolutely leapt out at me, which I suspect probably still holds true at the moment is that 76% of people want to work remote full-time and the companies that support remote workers have 25% lower costs. I think that stat might probably be changing over the next few months, Kyle.

KYLE: No doubt about it.

I mean, you know, just here in the U.S. we went from about 3.5% of the workforce being fully remote to now over 60% in the course of about a month and I’ve got to assume a lot of the people will stay remote.

ALEX: Yeah, I think some people are probably finding it absolutely fantastic to be remote and probably some that are struggling with it a little bit. Tell us a little bit about your journey setting Out of Office up, where the company started, and where it is now.

KYLE: Absolutely. Yes. Like you said, we started the company in 2018 and the idea was pretty simple. I had spent most of my career in commercial real estate and real estate technology. So I spent 10 years thinking about what makes a building work, what makes a building valuable, why do people use buildings for different activities.

This was right around the same time that you couldn’t go two days without hearing about WeWork and them raising another $1 billion or $10 billion right? And I could never really make sense of it. And, leave aside evaluation, I just didn’t make sense of the product because I had been to dozens of co-working spaces. I didn’t feel that anybody had quite nailed the experience of being a remote worker. And in fact, most people in those co-working spaces didn’t choose to be there.

They were told to be there by their boss, who happened to like the space and sign a lease. Which has really been the history of office space for hundreds of years. The boss decides where the office is and the employees are forced to go.

So I set out to build a different type of business. I partnered with my co-founder, Steve Flory, who is, you know, one of the top mobile engineers out here in Silicon Valley. We said, “Well, what if the office wasn’t a place? What if it was many places? What if it was a community?” And that’s what we set out to build with Out of Office.

ALEX: Fantastic. And so you very much started from thinking about the physical space and then perhaps thinking more about the mental space of the people working there?

KYLE: Yeah, I mean, I think the story of remote work is the story of autonomy. Ah, and unfortunately, right now with the pandemic, we have bits and pieces of autonomy, but we don’t have the full freedom to spend our day as we choose.

So I think that’s going to be the most interesting thing to play out in the next 6 to 12 months. Yeah, like you said, there’s both a structural component of “where do I sit?” and then “where is my headspace?” and “what is my mental health throughout the workday?”.

ALEX: Well, let’s dive straight into that. You’ve already touched on it, and I think we can’t really avoid the idea that the world, I think, is going to be fundamentally changed on the back of Coronavirus. How do you think that the world of work is going to look in… fingers crossed that everything’s back to some sort of normality, in a few months time. How do you think the world of work is going to look in the next year or so, going forward?

KYLE: So I think, you know, this is not going to be a unique view. You’ve probably seen lots of headlines about it, but I think we’re you know… we’ve accelerated the pace of remote-work adoption by probably 5 or 10 years. And, you know, like the stats I threw out at the beginning of the session here… Americans, in general, did not work from home, so we had about 3.5% of the population full-time without an office. Now 60% of us are full-time employed without an office.

We’re going to shake out somewhere in between. But, no doubt about it, every company out there is looking to cut costs. They’re looking to cut office expenses. And I think what you’re going to see is a lot more people believing that you can have the autonomy of remote work without suffering some lack of productivity or accountability.

So that is the first big trend. I call that the great dispersion. Right? It’s people leaving these monolithic headquarter offices and dispersing out into satellite offices or home offices.

The second major trend, which I don’t think is being talked about at all… because our politicians and healthcare workers are rightfully focused on stopping the spread of this virus… but there’s a looming mental health crisis right now. And, um, even before the pandemic, three in five people identified as being lonely in some way, shape or form. And you see a much higher prevalence of that amongst remote workers. And the reason is pretty simple, right? They’re missing out on 40 hours a week of casual social interaction. And so I think that that is the second crisis we’ll see post-pandemic… is one of mental health.

ALEX: I think that obviously, you’ve looked at the idea of isolation and loneliness way before this all hit. But that, again, is going to be hugely accelerated by this. I suppose we often talk about homeworkers, and particularly freelancers, making a lifestyle choice… and it’s often a positive choice. But I suspect now that you’ve got people upon whom this has been forced, that you actually have people perhaps not prepared for that kind of isolation.

And I certainly… it comes from some people on the site… that the isolation and loneliness of home working is one of the biggest things to deal with. But with those people who haven’t been prepared for that, who haven’t made the positive choice and considered that as an option… that’s going to be something that comes in.

Just in terms of where you’ve been on this before. What are your views on that? The isolation and loneliness side of things. Have you personally found ways of dealing with it? Has the company found ways of tackling that?

KYLE: Sure, yeah. Well, the first thing I would say is… I’ve seen the stigma around isolation and loneliness dissipate quite quickly. And this is not just in the Coronavirus world. This is, you know, for years prior.

Most remote workers and I would say especially freelancers, are quite self-aware of how they tend to isolate themselves and the impact that has on their mental state. So that’s a positive. That we’re at least aware of the problem, or most of us are.

In terms of how I dealt with this problem… the first thing I would do is leave the house. I always say the biggest co-working operator in the world is not WeWork, it’s not Regus, it’s Starbucks. You know, they give away the workspace and sell you coffee. WeWork just sells you workspace and gives away the coffee, right? So there’s a reason…

ALEX: I’ve never thought of it like that before. I love that.

KYLE: Yeah, there’s a reason people go to Starbucks, and it’s because they’re craving human interaction. They might not consciously be thinking that, but what else do you get? A table, a chair and WiFi. You can get that all at home. And so that’s the first solution in my mind, is just to get out of the house and be around other people.

But I find that is very much lacking, and most remote workers I talked to also don’t see that as fulfilling their need for meaningful relationships and interactions in their workday. That’s why we started Work Club.

ALEX: Right. Tell us a little bit about Work Club. I’m perfectly happy for you to do a little plug for your product here. It’s why we’re talking to you after all. Tell us about… I’ve downloaded the app but not had a really good play with it yet. But what’s the main idea behind it?

KYLE: Yes, thank you. So, as you mentioned, we have two products. The first is called Work Space. The second is called Work Club. We built them in that order.

It turns out that was the wrong order. So, when we started this business and, remember my background was in commercial real estate for 10 years, so I naturally thought “What do remote workers need? They need a place to work.” And it turns out that was the wrong thing to build. It turns out, like I said, the number one problem for remote workers is not finding an ergonomic chair or a nice place to work, its isolation and loneliness.

Work Space was a product where you could find a place to work for the day with good WiFi et cetera. Work Club was our solution for that number one problem. It’s a way to find a crew of co-workers for the day, to get some social interaction, and meet new people. So Work Club generally looks like a small group of people getting together in someplace around town… that could be a coffee shop, it could be a co-working space… getting together in a small group environment and spending the day together.

ALEX: Fantastic. And how has that worked in the world of social isolation? Are you finding people doing that virtually?

KYLE: It doesn’t work. So that’s the short version. On March 13th we had our last in-person Work Club. We fully intend to relaunch it and we’re very excited about that. We think, you know, as long as we can do so safely… it seems to be what the world needs right now. The world needs to get out of the house. The world needs some social interaction. So again, as long as we can do it safely, we’re very excited about the relaunch.

But to answer your question, yes, we did bring Work Club online just two days after the shelter-in-place order was issued here in California. We found a couple things. First of all, meeting and working with people online is better than nothing.

ALEX: Yes.

KYLE: So, you know, if given the option to sit in complete isolation by yourself behind the screen all day versus jumping into an online Work Club and co-working with some people for an hour… you’d rather do it online. But it has definitely galvanised our belief that the best product and the best experience for remote workers is to actually physically leave the house and physically be around other people.

ALEX: Yeah, I certainly think that will echo with a lot of people. It’s definitely something that I found working from home before we were all locked down. And I think everybody is desperate for that first sort of set of social interactions afterwards until, probably about two weeks in, you get fed up with people again and just want to stay at home.

But I think you’re absolutely right. There is that fundamental human… we are very social animals at the end of the day, aren’t we? That’s what we are.

KYLE: Yeah, I mean, it’s biological. And there’s plenty of studies out there. You know, there are studies that show loneliness has the same health impact as smoking a cigarette a day. There are studies, going back as far as the nineties, that showed a significant correlation between loneliness and hospital visits. So, you know, we are not a species that’s built or designed to be alone all day. And I think that is the real hidden cost of remote work and hopefully, we can get more people talking about it.

ALEX: Excellent stuff. So just going on to the practicalities of things and looking at stuff… it’s something that’s come up a few times as people start to go into this world, and I like your point earlier about the fact that what this has done is accelerate the direction of travel in terms of home working. I think a lot of people have said that this is the trend, and I agree with you there.

One of the things that’s come up historically, and people are looking at now, is, “How do you build a team of people within a business in a remote space?” It’s that thing of, you know… your first day in an office you get shown around the office. Where the kettle is. Where all of the snacks are kept. Who sits where. Who to avoid. Who to talk to. And maybe even where you all go to socialise after work.

How do you replicate that kind of thing in a remote environment?

KYLE: Yes. So I’m not sure if you’re asking specifically about onboarding or just how to build a team in general.

ALEX: In general.

KYLE: I’ll give you my general take. Because remote work has not been the norm, there are a lot of growing pains you experience as a company when you hire people that are hundreds or thousands of miles away. The number one advice I would give to anybody starting a remote-first company like Out of Office is, you need to hire people who are self-starters, who are comfortable with ambiguity and uncertainty, and who have enough experience under their belts to know where to best spend their time.

That was, I think, the biggest thing we’ve learned over the last two years. That people who really excel in a remote environment are people who don’t necessarily need to be micromanaged or told what to do.

ALEX: Yeah, I think that’s something that we’ve dealt with. We’re looking at the signs as well in terms of freelancers that there is that point and you’ve got to be… if you don’t have a boss, you’ve got to be your own boss. And that means doing everything, not just being able to sit there and hope somebody will tell you what to do. You’re absolutely right.

Is there anything else in terms of… obviously selecting people is correct. Is there anything that you’ve found in terms of sort of day-to-day management? Anything you need to try and… going back actually to the loneliness thing is trying to keep people sane, obviously with the exception of using Work Club and meeting up somewhere nearby.

KYLE: Yes, well, you know, we’re a technology startup, right? And the nature of the technology startup is you constantly question what you’re building. You constantly iterate. You approach the product with a design focus.

I think you need to approach a remote startup with that same design thinking. And what I mean by that is, most companies have a sort of set-it-and-forget-it policy when it comes to recruiting, and onboarding, and managing teams. For better or for worse, probably for worse, people are used to that environment where you come into a company and there’s a bunch of things you do on day one, and day two, and a three. And by month three, you have a quarterly check-in and so on and so forth.

So I think, as a remote company, it’s important to constantly question the software you’re using. The processes you’re following. How you’re managing your team. How you’re collaborating. Seeing what’s working and being able to have an honest, open conversation about that.

ALEX: Yeah, absolutely. I think that is so true. As with so many of these things, honest and open conversations, these are things that apply in every environment but perhaps are slightly more sharpened in the world of remote working.

You mentioned being self-starters, and I suspect it’s certainly something that we’ve seen is an issue that comes up time and time again. With, you know, people working from home, perhaps when they’re first getting into freelancing or something like that, is how do they ensure their productivity’s up? And the flip side of that is, how do they prevent themselves from burning out by burning the midnight oil every day?

Is there anything that you, personally or through your community, have come up with in terms of productivity tips that our listeners could take away?

KYLE: Sure, I’ll give you two. I’ll keep it very specific because I think everybody is probably a little overwhelmed with all the lists of remote work hacks. So I’ll keep it very specific.

Your listeners should look up two things: one is called the Pomodoro Technique and the second is called the Eisenhower Matrix. And both of these techniques actually came from our Work Club members. So I can’t claim any credit for it, although we’ve adopted them at Out of Office.

So the Eisenhower Matrix is a simple way to prioritise your tasks for the day. On one axis you have urgency and the other you have importance. And so, I think the value there is actually in that distinction: that everything that’s urgent is not important, and everything that’s important is not urgent. And so making that distinction early in your day allows you to plan out what you need to do 1st, 2nd, and last. So look that up and try it out.

The second, the Pomodoro Technique, is a time-management technique. It’s based on the idea that you should work in 25-minute increments with a 5 or 10-minute break in between to get up and stretch or socialise. And we actually use that technique with our online Work Clubs. So people will log on. We’ll meet. We’ll chat. We’ll dive into a 25-minute work session… cameras off, microphones off. Then we’ll come back on and debrief.

I’ve found that very helpful, especially during this shelter-in-place world we live in, but I think it just recognises the fact that work happens in bursts. There’s a big misconception, especially amongst creative freelancers, that you sit down at 8 a.m. and you work for 8, 9, or 10 hours and there’s a constant level of productivity, and it’s all about time in.

In my experience, in my entire career, my best ideas have come to me in a period of five minutes. And my worst days have come from eight hours of being, you know, sedentary and sitting in front of a computer.

ALEX: Yeah, that echoes so much. The Pomodoro Technique I’ve heard of a lot. I love the Eisenhower Matrix. I’ve got a marketing background and there is not a single thing marketers can’t put into a four-box matrix, or potentially a triangle if you’re getting really advanced.

But my other favourite one where Eisenhower finds a way into the world of business was… well, everyone goes to the Mike Tyson one… everybody’s got a plan until they get punched in the face. Which goes back to your earlier point of constantly reiterating. But Eisenhower was a guy which… he said: “planning is essential, but plans are useless.”

The point is your plan never comes to fruition. But unless you know how you got there, then you don’t know how to get yourself out of the mess you’ve found yourself in. But who would have thought that General Eisenhower would be resonating in the world of business?

KYLE: The world’s greatest productivity hacker, yeah.

ALEX: Well, that’s really, really good stuff. I think that those two things are absolutely… as soon as you said them, just immediately, I was like, “Yeah, they are brilliant, brilliant ideas.”

That point of sitting in front of a keyboard is, these days, sort of almost banging your head on it, trying to get to the point of going I’ve been here for four hours… I can’t get to it. That idea, I think, that people have. Even though you break the physical shackles of being tied to an office for eight hours a day… It’s very difficult to break those mental work shackles of I have to be at my desk doing stuff otherwise I’m not being productive.

KYLE: I think very few people sit down and think about how they work and why they work that way. And this is actually a great opportunity for everyone to do that. Right? Because we’ve all been thrust into an unfamiliar and potentially undesired environment.

ALEX: Yeah.

KYLE: Stuck at home. Maybe you’ve got kids, Maybe you got pets, or whatever. But it’s a great opportunity to think about “Why do I work this way?” and “What’s the optimal environment for me?”

When the world’s great CEOs and thinkers are asked the question, “Where do you get your best ideas?”, the answer is never in my office, sitting by my computer, after six hours of typing away on some reports. No… it’s on a walk, it’s at my favourite cafe, it’s, you know, sitting in the bathtub.

So I think recognising how the cadence and energy of your work impact your mental state is incredibly important. Remote workers, I think, are more self-aware about that and the rest of the world is quickly coming along.

ALEX: Well, to be honest with you, I can’t think of a better note to start to wrap up on that. I’m going to just quickly recap on a few things.

First and foremost, I absolutely love the honesty… the fact that you shared the idea that you started the business in one place, thinking it was about space with your real estate background, very quickly realised that that wasn’t actually the problem, but pivoted the solution to a different problem and went on.

I think there are some real lessons in that. And actually, I think, that if people are looking to set their own businesses up, that level of thinking, that ability to move and pivot is really, really important.

Just in terms of some of the things we’ve said, it’s perhaps for those working from home for the first time… Leave the house. Against all official guidance at the moment, but the principle is, get out of that space. Get out of the headspace.

Maybe have a walk around if you can leave for some exercise during the day. And if you can’t leave the house to go and talk to people as you would normally… then some online conversations actually… aren’t as good, but they’re better than nothing, as you quite rightly said.

If you are looking to actually build, motivate, or manage a team away from the physical environment, the important thing, first of all, is to hire self-starters. That’s the most important thing. Make sure that people are temperamentally suited to it. But always maintain that design thinking… change the way you look at things. Look at the apps that you’re using. Look at the things that you’re doing and always constantly evaluate and see if it’s actually working and see if it’s the right thing.

And in terms of productivity, the two quick hacks you offer with the Pomodoro Technique of working 25 minutes with a short break in between… or, if you don’t actually want to be that disciplined about it, you can actually take the principle of working in short bursts, taking a break, refreshing yourself, moving on…

And, of course, the Eisenhower Matrix – prioritise what’s going on. Does it have to be done now? Is it absolutely urgent? How important is it really? Go through that to-do list and maybe strike a few things off or put them off until tomorrow.

Have I covered pretty much everything there, Kyle? Or…

KYLE: That was great, we can edit the whole podcast down to about 20 seconds.

ALEX: Yeah, it would be a very dull podcast if it was just me listing the stuff you said. I mean, I could claim it. After all, it would make me look great. But, you know, all I did was repeat what you told us.

KYLE: This’s great. Yeah, I really appreciate it. And if any of your listeners want to find us, we’re at OutOfOffice.app, my email is Kyle@OutOfOffice.app and you can reach out to me any time.

ALEX: That’s very kind of you, Kyle. That’s brilliant. And as I say, if any of our listeners have got any questions for us or suggestions, then you can email Ben. Even though he’s not on the podcast, he’s still answering the emails… that’s the kind of guy he is.

And I really would like you, if you are listening and enjoying it, to write a review if you can and subscribe on whatever podcast app that you use, it really does help other people find it.

And just finally to finish off. Thank you so much, Kyle, for your time today. It’s been brilliant. Really motivational for me and hopefully for the listeners as well.

KYLE: Thank you. You’re very kind. Hopefully, everybody out there stays safe, stays positive, and we’ll all be working together soon hopefully.

ALEX: Brilliant. Thank you, Kyle. And goodbye, everybody.

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