Tyler Sellhorn: Local Teacher to Global Leader, Navigating Career Transition | Work 20XX #10

Jeff Frick
February 13, 2023
Listen this episode on your favorite platform!

Tyler Sellhorn runs remote for Polygon Labs, a blockchain development platform with 500 employees distributed all around the world. Less than 4 years ago, he was teaching high school algebra for the Fort Wayne Community school district, in Fort Wayne, Indiana, the 140th largest metro area in the US, not necessarily known for its bustling blockchain sector. 

Welcome to Work20XX, a show focused on the transitioning world of work, where we bring you the best minds in the business to provide insight, direction, and specific actions that leaders, line managers, and individual contributors can use as we experiment our way forward. 

I started the process with Tyler with every intention to deep dive into remote team management best practices, leveraging Tyler’s day job, and Podcast where he’s hosted the biggest names in the workplace. And yet, I find his career pivot to be even more compelling, and something more broadly applicable to an audience far larger than those focused on remote work, including those layed off in the past, and those still to come.

How do people, transition to industries, that didn’t even exist when they finished our formal school? Thousands of people are getting laid off, automation will remove many jobs, many of which are crap, but still. 

The good news is there are so many avenues to find a match for your current aptitude, applied to a new field, with some learning of the vocabulary, norms, community, discussions, hot button issues, voices, etc. And this is accessible online. Whether that be getting a certification for in demand cloud or data skills, or becoming a remote work expert as Tyler did, the resources are available, the information is available, and the community is available, you just have to pick which community fits your objectives. 

Tyler transitioned from High School Teacher to Customer Success for a software company, then Remote and Ops for a blockchain development platform, picking up hosting the ‘We Work Remotely” podcast along the way.

As Meg Bear likes to say, the secret to re-skilling is doing. What Tyler shows is all, is that the resources are there, listen to the experts, read the posts, and take the certification. The open-source ethos, layered on vast libraries of information, has changed the way we continue to learn, both for fun, professional development, and the more frequent than comfortable career pivot.

My conversation with Tyler Sellhorn

Episode Transcript

Jeff Frick

All right. So I will just count as down, Tyler, and we will go. Okay. Three, two, one. Hey, welcome back, everybody. Jeff, Rick here.

Come to you from the Home Office for another episode of Work 20 x x. And we're really excited about this next episode.

This some this guy has not been in the business for a long time, but he came to it from a completely different industry.

It as much as he's having some success in driving remote work for his organization, I'm really curious to know more about kind of being a

continuous learner and career changes and all kinds of things like that. So joining us to the magic of the Internet all the way from Fort Wayne,

Indiana, he's Tyler Cel Horn, the business operations manager and former head of the remote thing, is still part of the job at Polygon Labs.

Tyler, great to see you this morning.

Tyler Sellhorn

Jeff. It is a pleasure to be learning out loud with you all here today on the 20 x at work, 20 x x podcast. It is my sincere joy to be here with you.

I have been following your work and what you guys have been talking about here. And it is. Yeah, yeah. Truly a blessing to be

alongside you and alongside the pod cast guests that you've had on this,

this thing I've been looking up to so many that you have had on the pod and it's a it's a pleasure to be here.

Jeff Frick

Well, thank you very much. So before we get into it, let's get the the give the 1 to 1 on Polygon.

Tyler Sellhorn

So Polygon is the it's a decentralized protocol. So you're thinking blockchains. I'm going right into the jargon right off the top.

But really what we're

trying to become is platform technology for brands to launch on the blockchain, especially inside Ethereum ecosystem.

So we're building technologies that help us scale Ethereum and we are in the business of, you know, making blockchain adoption happen for the world.

And so we're building kind of like that, like a microsoft of the 2020s, right, that we're trying to become the place that, that builders are building.

So the way I say it in terms of like my role in the business operations team is to say that we're helping to build the decentralized workplace

that is building the platform for decentralized applications, right?

So, so just so people aren't confused, I'm not going to be too deep into blockchain here. But but your role is heading remote. So in the context of that,

in the context of the company,

how large is it in terms of people? What's kind of the where are the people distributed? How long have you been around? You know, some of the basics there.

We are a fully decentralized workplace, so any place that there is a cohort of English speaking knowledge workers, we have people working from there.

So sync Seattle to Melbourne.

Right. And all points in between. But our largest cohort of of people are working from India, our co-founders are from India,

and we have a like the largest quote unquote office is like,

this is not an office, this is just happens to be like a shared location.

There's several people that are working from Dubai, but we have people on East and west coast of North America, in Latin America,

in Africa, in in the Far East, in in Europe, all over the place.

And any place that they're like I say, you know, there's some English speaking knowledge workers. People work for Polygon there.

So it's about 500 of us all told.

And what I'm in the business of doing is helping us do that. Well.

Jeff Frick

Right, Right. So what's really interesting about your background is you were a math teacher in high school for about ten years or so.

And I think you did some middle school teaching as well.

And you've talked about, you know, we had a little bit of a prep call before this about, you know, you decided on your career based on your priorities,

and you decided that there were some things that were important to you in terms of time with your family, time with your kids, etc.,

which drove you to, you know, kind of your teaching career.

So I wonder if you can review that process a little bit. How did you get there? And then we'll get to, you know, making this change to running remote

for a tech company in the blockchain space?

Tyler Sellhorn

Yeah. So I wanted to become a teacher because I have a particular way of phrasing it that I, I was prioritizing an identity stack that did not put my profession as the number one thing.

So when people ask you, Hey, hey, what do you do? Right? I think the thing that I want to encourage people to start thinking is, well,

first of all, I am a spouse, right?

I am a parent, I am a youth sports coach, right? I am a faith community member right now. I would also count being a remote

working advocate all before I am a worker, right?

A remote leader. Right. And my profession is in service to those other identities. Even back when I was still, you know,

in my previous career as a school teacher.

Right. Why did I choose to become a school teacher? Because that kind of job served those other identities. And, you know,

I was finishing an educational leadership masters and trying to think

about what was going to be next for me in that career. And the next step wasn't available to me in the school district.

And so I said, I'm going to stop asking those people for permission to do the next thing and I'm going to find something for myself.

And so I started, you know, as you say, like like lifelong learner, I started studying for like Salesforce administration certification and I found customer success.

Right. And that was not a thing that I realized was a thing. And obviously here in the software space,

like that's, that's like a huge department in many companies,

right? To deliver value over and above the price of someone's subscription and, you know, retention, all that is built on people being able to use their software well.

And so what I did is I said, okay, well, I'm going to make this change. I'm going to stop being a technology oriented teacher,

and now I'm going to become a teaching oriented technologist.

And I kind of put like, you know, that together I got promoted and started leading the department and, you know,

I started podcasting in the space and it really became someone who is is like thought of as like, you know, here I am talking to you, Jeff.

It's amazing to say like, okay, if I stop, like linking my vacation to my location, if I decouple those things right now,

I can become friends with anybody, Right? Right.

That's that's willing to be be met with in here. And so I think that's one of the things that is really special

about the remote working space is how much more opportunity is available to you when you're I'm talking to you from

the 140th metropolitan area in the United States.

Right. There is not an opportunity for me to work for blockchain technology companies here in Fort Wayne.

And not not, not, not too, you know, so too much shade on my hometown.

But but they are not, you know, at the bleeding edge of like technology here. Like like we got some back office like like development agencies here.

And, you know, there's there's a few corporations that that have similar types of, you know, like technology,

you know, developer, you know, kind of back end here in town.

But like, that's not a thing here, like where the education and health care hub of a really large rural area.

We also if you drive a pickup truck here in North America,

very often you'll have purchased a vehicle that was assembled here in Allen County.

But the types of jobs that I wanted to work were not available to me unless I chose to work remotely.

Jeff Frick

So so there's so much marijuana impact, and I'm just going to hold a remote thing for a minute and we'll get there.

But but I think it's really important, right?

We're going through some tough times right now. A lot of people are getting laid off. You know,

there's a whole kind of rush to relearn and reskill. And, you know,

I think your story is is an illustrative one and one that people can probably gain some some insight from.

You know, when you sat down and said, okay, my my career path that I have mapped out in the education space, this doesn't look like it's going to work out.

And I'm I'm ready to take a pivot in terms of the comfort, in terms of exploration.

You obviously had the confidence, but how did you start to approach the education?

How did you start to approach, you know, jumping into this entirely new community? I saw on your on your LinkedIn,

right, you did an internship and you did a lot of education stuff.

So I wonder, you know, how did you approach coming from zero to jump into this new world and, and,

you know, be a lifelong learner, you know,

look at the opportunities that are out there because I think it's such I think it

really plays to lifelong learning to our next steps in the way that we get information.

And you've got an interesting context coming from a teacher background.

Tyler Sellhorn

I just want to encourage everyone to do the deep dive on who they are as a professional. Right?

When you look at like the skills of a secondary mathematics teacher, right? What did I do?

Well, I got students to think about values instead of, Oh, there's numbers and letters here,

Right? Right. We're teaching 12 year olds algebra at this point.

This is what I'm trying to draw for you, right? It turns out that teaching adults how to use their

software isn't so different from getting students to think about, you know,

like mathematics and how that works. Right? Know, very much of, you know, software is an abstraction of of our mental process.

Well, that that's algebra. Okay. And so when I started leaning into those ideas,

it wasn't that I didn't already have what I needed to be successful,

it's that I had not identified how that applied in, in, in an analogous space.

Right. So make the analogy, draw the metaphor for yourself in what you already have and connect the dots to something that

is more valuable or even just available at all right now in this market.

Right? So that was the conversation that I had with my spouse.

We were walking on a spring break on on a beach near Fort Myers where my folks have have a condo.

And we were talking about, okay, well, it doesn't look like things are going to happen for the school district.

Okay, well, what are you going to do? Well, what? Grateful for my spouse.

They said, what if you generalized what if he said instead of an educational leadership master's?

What if it's just leadership? Okay,

Yeah, I do know how to do that.

I'm a coach. I'm a parent, right? I do know how to take lessons from those places and apply them in other other avenues and other venues.

Right? I'm going to be someone who can influence

others in a way that is going to help a company be more successful working remotely or whether it's just executing it at all. Right?

And if I had the opportunity to to show up and get promoted within six months of of being at a company, you know, and just kept learning out loud,

being willing to say,

I haven't figured this out yet, but like, here's what I'm learning. And people respond to that.

Like, if you're willing to be an Internet person on the Internet doing Internet things,

it's really surprising just how few people are willing to do that, right?

If you are willing to do that, you can be noticed and elevated and given opportunities that you would never

have had if you were just alone by yourself, you know, on your laptop.

Right, Right. Show up and be seen.

Jeff Frick

I love it. And then the other thing, too, right, is we're in an age where just education and learning, you know,

everything is on the Internet.

I mean, it's all there. You want to fix your dishwasher.

It's in a YouTube video. If you know whatever you need to do. And I'm curious, you know,

as you started to accumulate knowledge and go from you clearly have the confidence, you have some skills,

but you didn't have the vocabulary.

You didn't have the connections, and you didn't have those direct things that you needed to be successful.

I wonder if you can share kind of your exploration and your kind of

knowledge growth around the specific area once you decided to go in this direction without going back to remote school or, you know,

whatever kind of missional means we've had for getting information over the last four years.

Tyler Sellhorn

So I grabbed a book on my way to the that the recording today.

This is a book called Work Together Anywhere by Lisette Sutherland and there's a foreword from from Juergen Apolo

this is like the agile kind of like like community right has done a lot of like outloud learning and so I just like start getting those people into your feeds, right?

I've listened to the entire archive of Lisette podcast, right? There were several like very specific customer success podcasts that I listen to.

I've read all the books.

These are things that like as soon as you start, like drawing, connecting the dots to like your own experiences,

you can start charting a journey that that includes those ideas that that are from somewhere else.

And there is zero gating on you deciding to learn something new. Now let's let's be very clear. I grew up I grew up in in our basement, you know, in the eighties,

building x86 computers in my dad.

So like, I mean, he was, you know, super nerd like about that kind of stuff, right? Like, there's definitely, you know,

object based relational databases where something that I understood even as a schoolteacher.

But what are those those those threads that are for you? I'm speaking to you. AUDIENCE Right.

What are those threads for you that you can connect the dots for yourself into what's next?

Because no one is blocking you from doing what's next except for you. And so, like, you know, why? Why did I get hired as head of remote at Polygon?

Well, it's because I, the summer before, had started a website called Head of remote dot X, Y, Z, you know, you know, built and maintained by, you know. Tyler So. Horn Right.

And then here's all the other people that I wanted to be like,

Right here, here are my North Stars, right? You know, including, you know, past guests on your show like Darren Murph and and Tracy Hawkins.

Right, Right. These are people that are that are like I've been following and engaging with and trying to make friends with online.

And now I am friends with them. Like literally friends like like

I've I've share beers with Darren Murphy in Berlin. Right. Like, these are things that like, like I appeared on stage with that person. And so it's, it's not that you can't do those things,

it's that you haven't done them yet.

Right. And so you know what you know educator stuff, right? Like, so I'm a huge fan of Carol Dweck, right. And you know, growth mindset, right?

The power of yet I have I have these links like in my

clipboard manager that I share with people all the time. Right? As soon as you change from I can't do this to I can't do this yet.

Right. It unlocks the opportunity for you to learn how to do it. Right now, almost none of what you see in the world is immutable and unchangeable. Right?

We oftentimes see a building get built,

right? And then and then all of a sudden it's like locked in in space. And it will never be different than it was. But eight months ago, right.

There was nothing there that was created by someone. Well, guess what? You can create the world that you live in, especially inside of a software world where like so much more is virtual.

Well, what did I do? I created that website that said my name is next to the heads of remote.

And by golly, that's what happened. And I think that it's not like this,

you know, woo woo, you know, manifesting stuff.

No, it's like I'm going to learn how to do that. And I haven't done it yet, but I will soon.

Jeff Frick

Right. It's just I just think it's such an amazing time in terms of just the open source ethos.

And you mentioned Darren, who's, you know, one of the best and, you know,

one of my main entry points into this space interviewing

in the years ago and the fact that everything is published in this open source and that they share best practices, whether that's for meetings or communications,

I mean, even to those even to the specifics of giving you text for an email in which to help you.

I became a successful remote job seeker, remote job worker and remote job remote leader because of the GitLab handbook, because of Jessica Reeder and

and Darren Murphy's work in publishing the remote first playbook.

Right. That is how I became this person. Speaking to you today is because I was willing to jump into the deep end and learn how to do it from the very best that is available to everyone.

Tyler Sellhorn

No one is telling you you can't do the next thing except for yourself. Right, right, right. Forget promotion.

Forget, forget, like just start doing the things that you intend to do.

And by golly, people are going to notice. Look at that person. They're doing the thing that we need in our company.

It's a matchmaking problem. It's not a worthiness problem.

Right? You are the top one for some company that's working remotely, right? You used to be that you had to live

within 30 ish miles of a headquarters to be able to to work at a company.

That's not the case anymore. Right? So start start mapping who you are to very specific things.

Jeff Frick

Right? So that you took it up another level and then you started you didn't start the podcast, but you jumped into the remote work podcast. I think in a third episode,

30 some odd out of the 80 some odd.

So you've done over 40 episodes. 50 episodes, Amazing. So tell us a little bit how you got involved with that and you know, what a fantastic

opportunity now to sit down with these same leaders that you keep talking about and now you're not

reading their docs on the website, you're sitting down with them and having these great conversations.

And I've listened to and I have a list of the whole library yet, but 80 episodes I'm working my way through.

Tyler Sellhorn

Well, you know, the the remote show from we work remotely shout out to Matt Hollingsworth and the team there. We work remotely for getting started learning out loud.

Before I showed up with the thing,

but I noticed that it had started out as a weekly show and then it was a monthly show, and then it was a sometimes monthly show and I just pitched them straight up.

I recorded my voice and pitched them and said, Hey, I should be your host. Looks like you. You don't have the capacity to do that anymore. And I would love to, you know,

you know, put my name with your name, right? The remote show we were currently I was working in, you know, a B2B SaaS company that was enabling remote work.

I wanted to put my name out there, like not just for me, but also for my company. And I think that's one of the things that is interesting is that because of the

Internet and because of personal computers, you can create, you can build, you can demonstrate,

you can show without anyone's help. Right.

Very grateful for the the audio engineer that we have onboard with us today and all the special things that Jeff Frick and the work 20 execs, you know, you know, the podcast kind of puts on their stuff, but like,

I'm kind of doing this thing with like broadly available tools for for anybody, right?

You just click the button and you can create that. And so what's stopping you, dear listener,

from doing the thing that is going to demonstrate that you're ready for what's next?

And I think that's something that is we're continuing to relearn the lesson of 1995 over and over again.

Computers can do stuff right, and the Internet connects us very, very closely with anybody that's out there with us.

Jeff Frick

Right, Right. So let's shift gears and talk about remote work. So now applying all this stuff to help helping your teams be more productive and more creative.

And, you know, I've got a laundry list of notes about some of the things that are the most important. So let's start with some of the basics.

And I think and I'll throw some words out and you can react.

You know, one is intentional, which I think is such a key piece. I think that was one of Darren's things I picked up early. And then and then of course,

async communication,

which really opens up everything. I wonder if you could speak to me. You used to teach in a classroom,

you know, have you kind of adopted async?

What do you see in terms of the opportunities that async opens up and really come to us from Fort Wayne,

Indiana, this, this opening up of your marketplace tab in terms of your talent that you can pull from?

Tyler Sellhorn

Definitely. And you know, so I quote Darren often right with the very thing I'm sure he said on the podcast. Remote work is a forcing function for intentionality, right?

The only things that people are going to know about us is what we tell them, because we're not going to be able to walk in and, you know, have the right clothes on.

Having driven the right car, you know, having the right hairstyle, right. I mean, there are some ways that you can take advantage of your personal image online, right.

To like like demonstrate that you are who you are. I, I appear on video conferences with the fancy microphone and headphones to say to everyone that I meet, I'm ready for your podcast.

Right. Part of why we're speaking today is because of communicate that to enough people over and over and over again how, you know, like this, this right here,

if you're watching. Right, is the moneymaker right in in in 2023. Right. How well are you able you know, I've got a curated background right now in my video conference.

These are things that are important to start saying to yourself, okay, what am I communicating with my my appearance?

And it's not going to be like your fancy portfolio binder that you bring to the conference room when you show up at the fancy office in Manhattan.

Right. That that that's not how it works anymore. So you need to, you know, level up and find which things are going to be able to be communicated intentionally.

Right. You have to find out, you know, consider all of it and then communicate who you are.

I'm wearing my my naval signal flags shirt today. I show up to almost all of my appearances in this shirt. Well, why is that? Because I want you to remember who

I am and what I'm about. And the biggest metaphor that unlocked so many things for me is remote in remote working was thinking of it like a naval captain might because I grew up on the North American Lake, Great Lakes.

When my grandparents sailing with their lives on their liveaboard sailboat. And I started thinking, okay, asynchronous communication.

Okay, so like you got to have a clear scope of work and an, a, a, a, a commission that you stick in your shirt saying what it is that you're about to do, right. And you go off and accomplish that.

That goal without anybody say so you you're the admiral is is back home.

Right. And so what are you as captain of your own ship going to be able to do? So I think that's one of the things that for me, asynchronous

communication is saying, how do I communicate this in concise language that can fit on inside of a letter right. With with very clear communication, with with words that have that are coded with with significant meaning right now,

obviously, like we're not actually on boats and, you know, sailing across the world like we're much closer connected.

Right. But, you know, the fact of the matter is that the sun only shines on half the world at a time. And so how are we going to embrace the idea that somebody is working when I am asleep?

Okay, well, I can still communicate with that person in a high bandwidth way with my tone of voice, with with my body language.

If I'm willing to be recorded in a video clip in in your chat platform of choice right. Send that person your face, your voice, your your

you know, you can even like, look at you don't have to get on a video conference to share your screen. You can provide

a voiceover with your whole thing, and then they can work on it separately from you in their own time and really absorb all of your words right?

And then reply, having thought carefully about what you said, These are things that have happened,

you know, a long time ago. So think, think 18th century, 19th century, right.

What did people do to communicate over long distances? They had to write down letters. Right? Right, right. And and now in the 21st century, we don't have to do that anymore.

But we can send something that is very, very considered and thoughtful and intentional with a recorded message. And I think that we're missing that when we only communicate via a text.

Jeff Frick

Wow. A lot going on there. I thought you were going to go a different route because, well, let's stick with the nautical theme. The other thing is the leadership, right?

I mean, it's one thing you can do the commission and say, Tyler, you know, sail across the sea and bring something back. It's another thing for you to be excited about it.

And even more importantly, to get your your people excited about the mission. So as much as an article is about, you know, kind of giving people responsibility and going,

it's also really about encouraging them to do their best work. So, you know, from kind of a leadership perspective, you know,

what are the advantages that you see in this kind of async world?

Tyler Sellhorn

Well, I think the thing that is unlocked by the defaults of remote working that that wasn't really there in office working is how much more autonomy individuals have.

Right When I say that 90 95% of the time we are not going to be co-located in our work.

That forces me as a manager to a whole other

level of consideration and honestly admitting that I never was in charge of you.

But I could pretend that I could express this power over you. Right. Because you had to come to the office, right? I had to make you dress up in certain clothing, right?

You had to, like, behave in a certain way the whole time that you were there.

Right. And and that has been exploded and ought to have been,

because we need to recognize that individuals are in charge of themselves, even in, you know, let's let's lean into the nautical analogy.

Even in a ship. Right. The happiest ships were always the ones where the captain understood that this is a a a symbiotic relationship.

I have a commission that has been given to me and I have been invested by the power of God to enforce this. Like, that's literally how the commission was written.

They read it off the articles of war to say that I can kill you if I so choose to make you do a thing, but that that kind of threat doesn't

produce a happy ship that kind of threat does not produce the kind of work that we want to see happen in the world.

Right. And what we need to do is we need to admit that individuals are in charge of themselves. And the more that we can admit that and then start expressing power

instead of expressing power over others, we express that power too, with and within our teams.

And when we are in invitational in that way, we will end up learning,

Oh, they do want to be a part of what I'm offering you.

They've RSVP yes to come further up and further into the organization. Or maybe they've RSVP. No, and I need to take on that information. Well, what is it that

I've done that maybe made it so that wasn't so attractive to be a part of things in fact, you know, if they are no enough times, you know, they're they're going to see themselves out.

Right. I mean, that's that's also a thing that we need to kind of consider, is that, hey, we are doing a business here. We are trying to accomplish a goal.

If you're not on board, well, we can drop you off on on the way. And I think that's one of those things that like mutinies happened, right? Like like that's, that's that.

And your your ship might be mutiny. Right? And you need to recognize that you need to, like, work with the people that are that are there in your on your ship.

And you need to be considerate of the fact that they have autonomy and power of their own.

Jeff Frick

So I want to flesh it out a little bit, something that you just mentioned, invitational leadership. You know, we talk a lot about servant leadership,

which a lot of people don't like that we're service. Leadership is often described in the idea being, you know,

you know, how can I use my power in a position of authority,

you know, to help you get your job done, to remove roadblocks?

Again, quote Darren till the cows come home? Yes. Yes. But I but I hadn't heard really kind of invitation leadership per se. So I wonder if you can just give us a

little bit more meat there in that kind of a concept, because I'd never heard that before.

Tyler Sellhorn

Yeah, I'm a big fan of servant leadership as well, and I think one way to express that right is to treat individuals, you know, as, as autonomous persons.

They, they you cannot make anyone do something that they do not want to do. Now, that might mean that they don't work at the company anymore.

But like, you've got to decide, okay, am I going to be someone who says, do this, do that right?

Or am I going to say, Hey, have you considered this yet? Why don't we try this next? Right?

And when someone pops in to that, you're giving that power,

that you've been invested in, that authority that you mentioned, Jeff, you're giving it a chance to be worn by someone else.

And that didn't mean that that authority disappeared from you.

It just meant that it now is invested in someone else as well. And that gives it a chance to grow, right? It gives it a chance to expand, right.

If we want to truly be innovative companies, if we want to truly be doing things in a new way,

we're going to have to give that responsibility and authority to the entire organization.

Right. And, you know, the more that managers can invest in power into the people that work for them,

the more that they're going to be able to find out new insights. They're going be able to learn from the people that are directly interfacing with customers.

You know, I've worked in, you know, customer experience teams and lead customer experience teams and the more that those people that are directly interfacing with customers can

learn from those customers and bring those insights back to the organization in a software as a service business,

we are co-creating that software with our customers.

And if we are able to learn directly from the people that are interfacing with customers directly,

we will get an opportunity to make something that actually delivers value.

Jeff Frick

Right now, you definitely want to listen to that customer. The other the other piece you talk about is the kind of ties, is intrinsic motivation,

right? Is trying to get that intrinsic motivation back to work back there from HP, who was on earlier episode, she said, you know,

that's really the essence because, you know, it's one thing to show up.

It's another thing to be enthusiastic and to really contribute and to put your, you know, kind of oomph behind that.

And, you know,

it's I think it's it's really interesting for these guys that are trying to dictate all this stuff at the most highest level versus really trying to push,

you know, as much in back to remote,

you know, as much of the remote norms down to whatever the logical unit of organization is possible.

So that, you know, it's it's it's just, I don't know, funny, sad, you know, remote as a word, just denotes hybrid.

And what we've found and what we know now is that there's going to be a million variants of the way people work,

as many as there are individuals based on whatever that situation is, that group, that company, that industry.

So it's really interesting, as you said, kind of pushing the autonomy down,

pushing the control down,

pushing the norms down as far as she can and as the commander just,

you know, given that direction and,

you know, kind of here's what we're trying to get and and is there anything I can do to help you?

Tyler Sellhorn

Yeah, I think that it's really important for us to embrace that full spectrum, right?

We need to embrace the idea that this is a both and situation instead of an either or situation.

Right. There are going to be organizations that are both hybrid, right and right in-person.

Right. There are going to be organizations that are both remote and hybrid.

I mean, I'm kind of throwing around these these buzzwords and combining them in different ways because there will be a spectrum of organizations

that choose to express themselves in the ways that serve that company best and the ones that do not think about this,

the ones that do not consider and make decisions with intention as as we've been suggesting,

those are the ones that are going to find themselves, you know, spinning their wheels, doing the same thing over and over again,

having the same conversations again and again and find them in the same spot next year as they were last.

Well, why is that? Because if we if we don't embrace the idea that what we are doing right matches up with what we are saying. Right.

People will will immediately. We have that clearly defined to them that these people don't know what they're talking about.

You can't dodge it. Right.

There was a certain amount of like inherent power being expressed over people when we told them they had to commute to an office.

Right. And now that they're able to work wherever for whomever, we're recognizing that like those times that people like,

dismissed themselves and found a new opportunity.

Right. That's going to this is what the great resignation or reset or whatever you want to name it is about is that people are recognizing that like, okay,

I was working this job because I lived here,

not because this was the best opportunity for me or for the company.

And I think the more that we can live in that moment of saying, okay, we want to find the people that are well-matched to our opportunities and

I want to find the companies that I am well matched for, right?

The more that we can embrace that,

the easier it's going to be for us to retain that talent and to invest,

you know, time and energy and learning and all the different things that go into that.

And we're also going to find that there's there's talent that's available to us fractionally.

That was never available to us before. If we're willing to work with them virtually to.

Jeff Frick

Yeah, it's really interesting, right? Because the talent shortage is not going away.

I mean, just recently they

announced that the population of China down. You know, people are waiting longer to have kids, are having fewer kids.

All these macro super demographic

trends are not going away, even though we've got a little blip here with with the round of layoffs of the last several months.

So the talent shortage isn't going to get isn't going to get easier. And the other kind of concept and I think

you've talked about it and you're almost a living example, is you don't

necessarily get to find the people that you need trained up in the skill set that you wish,

right? Everyone always likes to rip security jobs.

There's a kajillion million security jobs or aren't that many people. So this idea we really have to hire, you know,

hire the talent and then you can skill them up and train them as you want.

I'm just curious, as you've been in this role now for a couple of years, what was the biggest surprise to you,

both positive and negative as you kind of entered the software remote world that

people from the outside maybe either don't understand or,

you know, popular misconceptions?

Tyler Sellhorn

Well, I think it's really interesting how much society broadly enforces this mindset of I am going to wear one hat and one had only, I have a title,

I do this one thing right. And I think it's surprising to me how much I

let that be put on me and kept on my head and, you know, like, well, what did I do?

I became a customer Success manager, Customer success leader, customer experience leader, you know, doing it at like, start ups. Like, like, yeah,

I used to be a unionized government employee just right. And now I am working for a blockchain technology company.

That's quite the leap. And why How did I do that? Well, I start I took that

hat off and said, Oh, look at all these hats I could wear, whichever one.

And I think that's the thing that is most surprising to me is how much embracing general ism as, as a specialty.

That's that's kind of a, a misnomer of, of a portmanteau.

It's it's not actually putting them together, but like specializing in journalism,

Right? What am I doing? I'm spanning, you know,

business operations and people and like, like, like change management and technology and like these are things that like cross functional roles,

like customer success are way more available to way more people.

You mentioned cybersecurity, right? My very first remote hire was someone from Lagos, Nigeria, right.

Who took the customer

support job that they started off with and turned that into the funds necessary for them to emigrate to New Brunswick and study for

a cybersecurity job. And now they are working as a cybersecurity consultant

for Deloitte in Canada. Okay.

Well, like that kind of story needs to be written by each individual that says, you know what, I'm done being locked in to this hat, right?

And I'm going to do something else entirely, Right? Well, no one is stopping you from doing that except for you and there's

there's there's more available to you than you think. Right. Right.

And that's the thing that's most surprising to me is just

how much opportunity is available to you so long as you're willing to, you know,

say, you know, you know, just decouple your vacation from your location.

Jeff Frick

Right. You made an interesting comment in in actually,

it was when you were first taken over the podcast, you know, you talked about curiosity over judgment,

which I thought was really interesting. And if you could continue to have that curiosity and you also said something

that I think is it comes across in your in your smile right now, unconditional positive support, right.

In presuming positive intent. And I think those two things set you up so well

to be able to enter an area where you have no clue starting out in terms of vocabulary,

but going in with an attitude that I can learn. I don't have a clue yet to steal your line and there's

all this open source material out there that I can read and consume and I can even.

So interesting, right? You can actually touch people, you know, like, dear,

there was no way to touch an author before back in the day. And you could write a letter to the publisher

in New York and maybe it would find its way to the agent. You know, now the fact that you can actually reach

out and directly comment on somebody's social media post,

which is how we got introduced on LinkedIn and have that direct relationship such a different such a different world.

And you're really taking advantage of this kind of open aperture if you're

willing to kind of step through that screen.

Tyler Sellhorn

Yeah, I love that you called out curiosity over judgment.

And I want to speak again to the audience here and to say that, like you need to start with yourself about that.

Lean into the curiosity about yourself. Lean into step away from the self judgment.

My spouse is a therapist, so I have to you know,

I'm kind of kind of, you know,

boost the signal there that, you know, people like Brené Brown.

Right. Have had a huge influence on me as I've stepped, especially as I've stepped into my second career.

But the idea of embracing vulnerability. Right. And and stepping into being willing to be seen to step

into the arena and and and fail and even even fail miserably.

Right. That's that's actually the best place for you to be, right, is to be contending for

what the kind of life that you want to be living instead of the one that's been forced upon you.

Right. Right. And the more that we can say to one another as well as to ourselves, tell me more about that.

And I think I just heard you saying this is

is that really the case instead of being. What do you mean? Why are you doing that?

Jeff Frick

Right. Right. Love it. The other piece that we share is we're both coast coaches, youth coaches,

and and I've talked to many people over the years.

There's a certain satisfaction with that comes with accomplishing a goal is a

whole different level of satisfaction when you're

coaching and the kids accomplish the goal, just like you're communicating. Like, did they get it?

Did they do it? Did they see it through? And it's it's just like, oh, I mean, it's it's such a

different experience to coach and it combines, you know, skills and and inspiration and, you know,

picking them up when they're done all these things. I wonder if you can share, you know,

some of the things you've taken from your coaching experience into your into your new career.

Tyler Sellhorn

The number one thing that I have taken away, I'm going to reference specifically Snyder football for Fort Wayne.

SNIDER Football has been one of the very

most successful high school football programs in the nation and in the state of Indiana.

The way that we think about,

Jeff Frick

I thought it was basketball state, Indiana.

Tyler Sellhorn

Well, you know, Fort Wayne Snider is is the Panthers are number one in football.

We're also have some some some success on the basketball court to Tiffany Gooden.

I mean give me go on like you said you know youth sports I've

that really is something that turns me on and is like a a love of mine.

So the thing that I've learned from Snyder football is is number one, that we need

to ask the question, have we taught them how to do it right, Number two, Right.

And they do it right. And then we can ask the question, ooh, are they actively choosing not to do it Right?

We have to, you know, start with ourselves as leaders when we're thinking about someone's performance.

Right. Because, you know, if they really won't do what you're asking me to do,

they need to stand and watch and maybe not be on the team at all.

Right. But if we haven't given them what they need to be successful,

we need to take that on for ourselves first. Right. And, you know, obviously,

like working with children is different than working with adults.

But I think these are all things that we need to start with in terms

of how we're evaluating the people that work with us is,

you know, did I give them the system in which they could thrive and be successful right

where we call in the wrong place, Right.

Oh, we're okay. Well, then we need to change or change it up and we need we need to adjust.

And I think that even just starting with that framing of how can I enable someone else's success,

right? You talked about the joy of seeing someone executing at a high level in a championship moment.

I, I live for those moments when there's a worthy opponent right.

And and in the heat of the battle, you know, you're going to to fall to your level of training.

Right. And if you've hard enough to have a very high floor man, it

is awesome to see that that that ball get scored or go through the hoop or whatever your sport happens to be.

I love, you know, big fields with lots of players.

So, you know, like I love soccer, I love American football.

Shout out to the international listeners if it's just just football and say we can we can, you know,

embrace the phrasing that's, you know, in world football.

But for me, the thing that turns me on most about youth and sports in general

is the fact that no one can be successful individually without the collective effort.

Right. You know, I was an offensive lineman in in, you know, my playing days and nobody knew what I did. Right.

I had to say that I got in the way of the guys trying to get the guy with the ball. Right.

They like like people that know football know that offensive linemen are some of the most

important players the on the field because that you can't get the ball out of the backfield if no one's blocking.

But you know for me I love that part of my personality is that I am a helper,

right? I'm doing the blocking, right? I'm right.

I want to celebrate with the running back when they score the touch. Right.

You know, you know, let's get into the end zone together and celebrate.

But it didn't need to be me, you know.

You know, you know, on the camera, so to speak. It's more so that I was the one

enabling that other person to be successful.

Jeff Frick

That the piece that you said that I that I wasn't expecting, I think is really powerful here is, you know,

did we give them the tools? And I think that's such a such an important piece of the remote work story.

Right? Is all these managers and their and their bosses who didn't grow up in a

world that they couldn't see their employees and, you know, are we giving them the tools?

Are we giving them the training? You know, are we helping them? And you said a lot of people said it right.

Forced forced remote work during COVID was not remote work. That was for streamer remote during COVID.

But we're getting towards the end of our time. And I want to throw one more thing in and you do it really, really well.

The only other people that I that I can recall off the top of my head, the dude all the time,

or a lot of the Amazon people.

And that's infusing your culture into all your conversations and really being, you know,

kind of forthcoming in the whys about as you speak and, you know, making sure that the values are woven in because it's not just an instruction.

I just want you to do this because of no particular reason. But there's there's a reason behind it,

and it ties back to something bigger.

A lot of companies write their values down and they stick them on a poster someplace and never to be seen again.

Good companies live their values and all their actions and you can see it and you hear it and you and you can feel it.

You clearly have deep seated values. You're working all those into your day to day job. How do you do that?

How are you making sure that people understand, you know, kind of what's the big mission?

Tyler Sellhorn

Well, let's zoom out like like all the way I talked about at the beginning, like, who am I? What is my identity? Stack Right.

And I am a spouse.

My spouse is a therapist.

I talked about that earlier, right. And that I am a parent, right? Like being invested in my children's lives is important to me.

I could breakfast every day and pick them up from school every day because of remote working.

Right. I am a youth sports coach.

I am involved and have learned to work hard and care about my teammates right over and above

myself because of my experiences in sports and continue to experiences in sports.

I'm a faith community member, right? I like my my beliefs as a person. I am an integrated person. Jeff.

I am somebody who is that person as a professional, right?

My personhood doesn't depend on my job title, right? Who I am and what I'm about doesn't lean

on corporate values or or any of that.

Right? I'm looking for companies that are interested in that person being inside of their company.

Right. And I think that's one of the things that is is my encouragement to to anybody.

Right. Is to say go deep on the introspective, go deep on the reflective.

Think about who you are. Do you even know who you are? Right.

And that's going to give you a chance to be able to express an enthusiasm and joy that I

get to express every day because

I'm about this. Why? Why am I about. Because that was that didn't depend on me being at a

particular location or job or space or any of that.

I have chosen who I am before. I've chosen what I do love it.

Jeff Frick

I just I can't help but think of that kid's book with the guy with. He's got like 15 hats on,

right? He's got the reds and the blues and the black, the stripes and, you know,

it doesn't matter what hat you wear where all that's kind of emphasize the one for the moment.

But, you know, we can be integrated.

People all love that.

Tyler Sellhorn

Love you. You drew out a really great quote from me that was that was like getting to say it all at once.

Right. There was pretty special.

Jeff Frick

Yeah, Well, I think it's so important, right? I mean, it's work is a series of tasks.

And if people can be happy in their work and they can be fulfilled in their life and they can

be focused on the time that they are

working instead of distracted me. And ironically, it was it was a job that I took working for an

Australian based company that took me out of coaching

sports because all the meetings were at 4:00 pm

On the weekdays, right? Prime time practice time. So it just always struck me like,

why can't someone manage their own schedule that if they need to be at a parent teacher

conference from 3 to 4 on a Tuesday,

just put it on the schedule. Don't take any other meetings from 3 to 4 on Tuesday.

I mean, grab a meeting at 430 and you probably had one or two.

But it doesn't mean that you can't manage your own schedule.

Again, we'll just close on on Darren. You know, get lab manager of one.

You know, the responsible for your own for your own, for your own self.

Tyler Sellhorn

Well I think that you know I mentioned was that Sutherland and Jurgen Appelo

I think this is one of the things that we're learning from the best of,

you know, the agile community,

right? And what they have, you know, self-organization of individuals and teams is the way

forward in in this distributed environment, right?

It turns out that we were more distributed than we realized when because like as

soon as you have people on like more than one floor in a building.

Right. Right. It's going to be difficult for them to see one another unless they, you know,

happen to eat lunch at the same time in the cafeteria or bump into each other on the way into the office, which.

Right those those moments can't be, you know, organized for serendipity and joy and creativity.

But as soon as we decide that that's what we're going to do together, we can make that happen even asynchronously.

Jeff Frick

Right? Right. Oh, there's so many there's so many levels to that. Or even, you know, all the people in the business.

The occupancy was only 40%, you know, in 2019 anyway,

because people are at meetings, are at conferences. They're their customers. You know, they're they're at other places.

So to your point, it wasn't as synchronous as people thought.

To your point. People are on different floors, different buildings, even in the same company.

And, you know, the intimidation of walking up to the boss and asking a question,

I mean, that's it's not something that happens very often versus pretty low risk, pretty low friction to drop in.

I am maybe they come back, maybe they don't is simple and clean and in fact turns out to be a really

effective way to break down some of those some of those barriers that really in the way communication in an office.

Tyler Sellhorn

Especially for the organizations that are in the business of innovation.

Right. Those small companies that are that are nimble hire time to hire is is shrunk when you are hiring remotely.

Right. You know time to to onboarding if you do it intentionally is is much much smaller

because it's similar tools it's similar practices.

We're not you know, having to reinvent the wheel all the time.

This opportunity, if done well, is going to put rocket fuel on whatever

it is that you're doing right. But if you do it poorly,

you're going to be kicking the rocket over into the ocean.

Jeff Frick

What are you excited about? You know, that format and where you can go

and where you can take it and what you can explore,

where are you going to go with the podcast?

Tyler Sellhorn

So we're getting ready to start talking to a whole lot more people. One of the things that

I'm really interested, you know, so hopefully,

Jeff, you know, enough people are listening to this year and you're saying,

Hey, that guy seems interesting and he's pretty enthusiastic about this remote thing. Well,

I'm very interested in talking to people that have become remote

since the pandemic and have chosen it for their lifestyle going forward.

We've had lots and lots and lots of 2019 remoters,

and we'll continue to have the 2019 remoters is on the pod,

but I'm really interested to learn from and hear

from people you can find how to pitch me to, to appear on the podcast,

on on all the links that I'm sure Jeff will include in the show notes.

But click on that and send me an email with a recording of yourself and be reflective

about why it is that you've decided in 2023 and beyond to be a promoter.

What makes you say,

Yeah, this is for me in the long term. In fact,

I don't think I'm ever going back to an office.

Jeff Frick

Yeah, yeah. Well, I'm sure they will be coming out of the woodwork.

Tyler Sellhorn

So I'm looking. Forward. I'm looking forward to learning out loud with you.

Jeff Frick

All right. Well, Tyler, it's been a treat. And thank you for spending a little of your time with us today.

And congrats on making the career transition.

Congrats on the podcast and really congrats on having a good

attitude about about change and move moving forward.

I think it's a it's something that a lot of

people can benefit from and hopefully a little bit rubs off as well.

Tyler Sellhorn

Well, it is my pleasure to drop the air horns playing on this episode with you. Enthusiasm is dope, Jeff, and there's

nothing wrong with being excited about what you're doing and being invested in it and trying to do the thing,

trying to accomplish your goals, right? It turns out that, you know,

giving a shit is high leverage, right?

When you communicate care and concern for yourself and for others, people want to be around those types of people.

Jeff Frick

Love it. All right. Well, thanks again. Thanks, everybody, for listening and watching.

He's Tyler. I'm Jeff.

It's Work 20XX. We'll see you next time.

Thanks for watching on YouTube and listen to the podcast. Take care. And we are out.

That's great.

Tyler Sellhorn

Oh. Thank you so much. Really appreciate you.

Jeff Frick

A super fun.

Links and References

Tyler Sellhorn, Business  Operation Manager, Polygon Labs





The Remote Show Podcast 



Tyler’s ‘cache’ of referenced assets he’s always ready to share 

Distributed Work’s Five Levels of Autonomy by Matt Mullenweg


Podcasting Microphones Mega-Review by Marco.org

(Note, my recommendation, the Shure MV7 with BOTH USB and XLR interface and excellent automagic software)  


Brené Brown on Power and Leadership 10-26-20.pdf by Brené Brown


Dare to Lead, by Brené Brown, Random House, Oct 2018


The power of believing that you can improve, Carol Dweck, TED Talk, Dec 2017



Mindset: The New Psychology of Success, Carol Dweck, Ballantine Books, Dec 2007




Select episodes of The Remote Show Podcast with Tyler Sellhorn 

Tsedal Neeley, Author of Remote Work Revolution, Naylor Fitzhugh Professor of Business Administration Harvard Business School, Ep 80, Sept 2022


Job van der Voort, Founder and CEO at Remote and Darren Murph, Head of Remote at GitLab, Ep 58, Sept 2021


Ryan Anderson, VP Global Research & Insights, Herman Miller, Ep 56, Sept 2021


Laurel Farrer, Founder Distribute Consulting, Remote Work Association, Ep 38, Apr 2021


Chris Herd, Founder and CEO, FirstbaseHQ, Ep 37, Apr 2021



Other Links and Resources 

Tyler shares the stage with Remote Lumiaries Camilla Boyer, Chase Warrington, & Darren Murph  - The Reality of Remote Session, Employer of the Future Conference 2022, Amplifier, Berlin, Germany 


On YouTube - https://www.youtube.com/watch?v=IeRNtXirpqc 

Inside LinkedIn’s New Hybrid Office With More Than 75 Seating Types | Open Office | WSJ, Wall Street Journal YouTube, Jul 2022 - https://www.youtube.com/watch?v=p_J3o8VU5rw 

Designing a better tomorrow, MillerKnoll, Apr 1, 2022


When people talk about being really communicators, they often talk about speaking. They don’t focus on listening. And listening is a tremendously important skill - David Pottruck. Jeff Frick LinkedIn, Sep 11, 2021 


Give the customer permission to be comfortable being critical - David Pottruck, Jeff Frick LinkedIn Post, Sep 11, 2021 - https://www.linkedin.com/posts/jefrick_thecube-leadership-experience-activity-6872214951587643393-R1jJ

Conan Visits Intel's Headquarters | Late Night with Conan O’Brien, Conan Classics YouTube, Original air Date - May 2007 -  https://www.youtube.com/watch?v=gXReifFHXbY  

Caps for Sale: A Tale of a Peddler Some Monkeys and Their Money Business, Esphyr Slobodkina, W.R. Scott, 1940,

HarpersCollins, Reissue Edition, 1987




Individuals Mentioned

Brené Brown

Brené Brown on Power and Leadership 10-26-20.pdf by Brené Brown


Dare to Lead, by Brené Brown, Random House, Oct 2018


Carol Dweck

The power of believing that you can improve, Carol Dweck, TED Talk, Dec 2017



Mindset: The New Psychology of Success, Carol Dweck, Ballantine Books, Dec 2007



Carol’s Author page on Amazon 


Growth Mindset - Psychology Today 


Jurgen Appelo

Jurgen Appelo, Agility, Innovation, Experience and Leadership 




Startup, Scaleup, Screwup: 42 Tools to Accelerate Lean and Agile Business Growth, by Jurgen Appelo, Wiley, April 2019 


Work Together Anywhere: A Handbook on Working Remotely—Successfully—for Individuals, Teams, and Managers - By Lisette Sutherland , Kirsten Janene-Nelson , Jurgen Appelo , Collaboration Superpowers, Sept 2018


Lisette Sutherland

Lisette Sutherland, Facilitator, Author, Speaker - 



Work Together Anywhere | Lisette Sutherland | TEDxKaunas, Feb 6, 2018 




Abbreviations and terms  

TAM - Total Available Market 


Disclaimer and Discloser 

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 © Copyright 2023 Menlo Creek Media, LLC, All Rights Reserved 


Jeff Frick
Founder and Principal,
Menlo Creek Media

Jeff Frick has helped literally tens of thousands of executives share their stories. In his latest show, Work 20XX, Jeff is sharpening the focus on the future of work, and all that it entails.