Episode 176

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Published on:

30th Dec 2025

Remote Work Leadership: How Ken Taylor Builds High-Performance Teams Without Offices | Ep. 177

Episode 176 Frederick Dudek (Freddy D)

Remote work leadership takes center court in this powerful conversation with Ken Taylor, author of Working in Slippers and lifelong technology entrepreneur. Ken breaks down why remote work isn’t a pandemic trend—but a return to how humans and businesses perform best.

From hiring the right character (not just resumes) to onboarding remote employees like elite athletes, this episode tackles the real challenges service providers face: disengagement, misalignment, and burnout. Ken shares proven systems for remote onboarding, team engagement, and building culture without cubicles.

If you want a team that shows up like die-hard sports fans, not clock-watchers, this episode delivers a playbook that wins—no commute required.

Discover more with our detailed show notes and exclusive content by visiting:

Key Takeaways

Character beats credentials: Remote teams demand self-managed players who lean in, not wait for whistles.

Remote onboarding is a system: Screen-sharing, shadowing, and structured check-ins replace “desk proximity.”

Engagement creates superfans: Pizza days, team dinners, and shared wins keep remote players emotionally invested.

Unlimited leave builds trust: Treat adults like professionals—and they’ll perform like pros.

Global work demands flexibility: Early calls, late calls, and life integration are features, not flaws.

Culture isn’t location-based: Relationships are built through rhythm, communication, and shared victories.

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Guest Bio:

Ken Taylor is a technology entrepreneur, remote work strategist, and author of Working in Slippers. Raised in a family of tech startups, Ken has spent decades building and leading distributed teams across the globe. His expertise lies in remote hiring, onboarding, and leadership systems that help companies save money, improve performance, and build loyal, engaged teams without traditional offices.

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Freddy D’s Take

This episode is a masterclass in modern leadership. Ken Taylor doesn’t just talk theory—he’s lived remote work since before Zoom was cool. The biggest win? Remote work done right turns employees into superfans, not disengaged contractors.

Think of your team like a championship roster. If you recruit for character, train with intention, and celebrate wins together, geography becomes irrelevant. This is exactly the kind of ecosystem-first leadership I help clients implement through my SUPERFANS Framework™ inside Prosperity Pathway coaching.

The takeaway is simple: better culture + lower overhead + higher loyalty = competitive dominance.

FREE 30/Min Prosperity Pathway™ Business Growth Discover Call

The Action:

Redesign your onboarding for remote success

Who: Service business owners & leaders

Why: First impressions create long-term loyalty and performance

How:

  1. Add open-ended application questions
  2. Use live screen-sharing during onboarding
  3. Pair new hires with multiple team members
  4. Schedule weekly human connection check-ins

Mailbox Superfans

Guest Contact

Connect with Ken Taylor:

  1. Website: WorkingInSlippers.com
  2. LinkedIn: Ken Taylor

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Resources & Tools

Working in Slippers – Ken Taylor’s remote work leadership book

Zoom / Google Chat / Slack – Remote collaboration tools

Prosperity Pathway™ Coaching – Ecosystem & Superfan strategy

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Copyright 2025 Prosperous Ventures, LLC



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Transcript
Ken Taylor:

If you have somebody that's second best but they're the only one that's there and you're depending on them, things are not going to go as well as they need to.

Intro/Outro:

But I am the world's biggest super fan. You're like a super fan. Welcome to the Business Superfans podcast.

We will discuss how establishing business superfans from customers, employees and business partners can elevate your success exponentially. Learn why these advocates are a key factor to achieving excellence in the world of commerce.

This is the Business Super Fans podcast with your host, Freddy D. Freddy, Freddy.

Freddy D:

Hey super fan superstar Freddy D. Here and this episode 176.

We're joined by Ken Taylor, a lifelong startup operator who helps leaders solve one of today's most frustrating challenges, building effective teams and processes. In a world of remote work, broken.

Freddy D:

Hiring systems and constant change, too many.

Freddy D:

Service based businesses struggle with alignment, accountability and talent that just doesn't stick. From getting an early ringside seat to his father's startups, he became the first non founder hire at a fully remote company that never went back.

Ken brings hard earned real world proof. Ken brings hard earned real world perspective.

If you're trying to scale without chaos and build a team that actually works, this conversation delivers clarity and direction.

Freddy D:

Welcome Ken to Business Superfans of Service Providers Edge podcast. Great conversation that we had before we started recording so let's continue that conversation on the mic. Welcome to the show.

Ken Taylor:

Thanks so very much. I'm glad to be here. Freddie.

Freddy D:

So what's you know we had a good talk about you've been in working in the SaaS space in a sense and technology aspect and all that stuff. But and let's go back to kind of the backstory. How did this, how did you get into that arena?

Ken Taylor:

I came by naturally. My father was involved in tech startups my whole life.

Even as a little kid, you know, crawling around between the servers on floor of his offices there, his companies and somebody grabbed me by the scruff of the neck so I don't hit the button and shut the whole system down. And now that was back before remote work was, was very common in the early days.

But as time went on and my father moved further out to take care of his family and not being in the city anymore, there came to be more challenges with that, with getting people if you can afford an office out in the country, but then you can't get people that can actually work there. So he moved into remotely working himself and so we would be there in the house.

He'd have his office and there might be a phone call at 2 in the morning from Tokyo or London or whoever he happened to be working with.

And that was an interesting way of growing up because with many people, you know, Dad's home in the evening after work and maybe on the weekends with our family, dad was there all the time, except when he wasn't. I mean, he might have a business trip and be gone for a week or two, but when he was home, he was there. He was working, of course.

But as a small child, it's all right. You can still go in and maybe have a quick hug or say hi in between phone calls. And that was a pretty nice way to grow up.

And it certainly worked well for him being able to be involved in the family to an extent that not everybody has the opportunity to be.

And something that I learned moving in those circles was how important getting the right people is, that you need the very best person for each particular role. Now that's true in every company, but it's even more true in a small company or in a startup.

Because if you have somebody that's second best but they're the only one that's there and you're depending on them, things are not going to go as well as they need to. So you have to get the very best possible person in every single seat.

If you live in New York or Silicon Valley, maybe you can find the very best person, but most of us don't have the money to be there.

How are you going to find somebody that is at that level that lives right close to you, that can come over with remote work that allows you to find the person wherever they happen to live?

Certainly people that have been some success in their life, well, some of them do like living in New York and Silicon Valley, but a lot of them move to Idaho or Florida or Texas like myself or Wyoming or wherever. How are you going to put them all together unless you have tons of money? Remote work gives you that opportunity.

I saw the way that he worked with that growing up. As I went into my own career and started my own businesses and worked for other companies.

I've worked in offices about half the time and I've worked remote for about half the time. Years ago it was a telephone and fax machine and then the Internet came along. You got email.

Not so keen on texting, but nowadays we have the zoom calls and video conferencing and that has made a world of difference, I think for techies, well, they were always more text oriented anyways. Like people My dad grew up with telnet and those kind of things, the tech command line. And that's how they would deal with each other anyways.

But most people don't like that. Most people like to see who they're talking to. And now we have the tools to do that, just as you and I are doing right now.

We are a thousand miles apart, and yet we can look at each other, we can see each other, we can watch our reactions. Okay, maybe it's not as much as if we were in the same room, but it's a lot closer than the old days on a phone call.

Freddy D:

Well, it goes further than that, Ken, is. Because in the old days, you know, phone call was one thing, but a lot of times you'd had to hop on an airplane or hop in a car and drive for hours.

You know, when I got started in the tech space as an applications guy, initially in the early 80s, my role was to install software called CAD CAM, Computed Manufacturing. And I would have to drive to, let's say, go down to Bell Corporation, Ball Corporation, I mean, and you know, that was down in southern Indiana.

So I would have to hop on a car and drive numerous hours to get down there to do the training and be there for a week. Today you can do all that training, as you just mentioned, via video conferencing, or we would have to hop on an airplane.

I remember one of my first training companies was Westinghouse in St. Louis. And I had to hop on an airplane, fly a couple hours, rent a car, go to the facility, stay in a hotel to conduct training for a week.

And today, like you just mentioned, the whole game has completely changed.

Ken Taylor:

Absolutely.

And I get the impression as I speak to people myself, like my father, there was a time when there was the sort of the gilded age of travel, you know, Pan Am and things like that. Maybe we've seen some of that in old movies or TV shows. That's not really the way travel is anymore. Travel. I'm sorry, but it's kind of a slog.

There's not that many people that really enjoy doing business travel. The hotels tend to be pretty meh. Renting the car, who wants to do that? Flying, waiting in line, getting the flights canceled.

I mean, it's just not pleasant. It's worse than a commute, driving into the office and certainly takes longer in most cases. And then there's all that time that's wasted.

And yeah, we have Wi Fi now. You can set up your laptop and work on your computer while you're traveling, but that's pretty risky.

We all know how unsecure WI FI connections can be. Or who's sitting in the seat next to you.

We've heard about corporate espionage where they'll see where somebody is and buy the seat next to them and they're watching. What can you learn from that? How paranoid do we need to be? How paranoid do we want to be? That's not pleasant.

We're in perfect comfort in our own chair that we've bought to our own specifications. We're in our own private office. If there's somebody snooping on us, we'll probably notice. And it's better for the people and for the company.

In most cases, every weekend it's a good idea to go and meet people and shake hands. But it doesn't have to be all the time.

Freddy D:

No, you're right, because I remember when I would have to go to like someplace in Indiana or Ohio, and especially in Indiana. I was in Chicago at the time.

I would get up at like 2 o' clock in the morning and drive because I knew I needed to be there by about 7 o' clock in the morning to get set up for the training. You know, that was a long day because I had to drive at nighttime. And actually one of the times I actually hit a deer going down into Indiana.

But then to be there 8 o' clock in the morning, game time, do the training all day and then I would end up going into the hotel and crashing. So you're right, a lot of hours were burned up, but that was it. That was the only way you could do it back then.

That was the early pioneer days of the tech space.

Ken Taylor:

You do what you got to do.

But I certainly don't mean to be critical, but I'm going to venture to guess that you probably weren't at your best along about 2 or 3 o' clock the afternoon when people are starting to ask questions about the training. You're not really.

Freddy D:

I was definitely drinking a coffee then and trying to stay caffeine and up. And you're absolutely right, it was a long day.

But that's what you had to do back in the day because at, you know, for a while in the early, very early beginning, flying was in. But then they realized, okay, I think the rule was if you could drive within five hours, you weren't allowed to take a flight anymore.

Freddy D:

Oh God.

Freddy D:

So that changed dynamics.

Ken Taylor:

Oh dear. Yeah. Five hour drive, not a fun thing. And certainly not to have to work after doing five hours.

I mean, I suppose drive five hours, then spend the Night in the hotel, then work all day, then spend the night in the hotel, then drive five hours back, but then you've burnt three days for one day of meetings. Right.

Freddy D:

But that's how the world operated back then.

So what we're really talking about is how life has changed in the last 45 years, has really evolved in a significant way with the conveniences in the technology that's come about.

Because, you know, and I think the newer generation that starts off today doesn't understand the things that needed to be, you know, all the hoops that we just talked about that you need to jump through and go through to conduct business where today you can do a lot of the business on your smartphone.

Ken Taylor:

Well, that's absolutely true. I am very fond of history. I've taught history in the past and I think there's much to be learned from history, not just in the.

Those that don't learn from history, all that, but that applies to business as well.

And seeing how business has changed over the years and learning what has been done in the past and how things were done and how that can be applied to today. There was a time when the cost and the uncertainty, I mean, it was 10 bucks a minute for a phone call to Tokyo.

So you make it as short as you can and you're talking with a Japanese person, presumably, who speaks English.

If you're in a hurry and watching the clock, are you absolutely sure that communication, that there's a true meeting of the minds, that there hasn't been something lost in translation? Nowadays you don't have that problem. Just send emails back and forth, ask questions, do a zoom call.

If there's any uncertainty, you can iron it out and say, are we absolutely sure we're talking about the same thing? Are we on the same page? And those of us have had that experience of working with people overseas and.

Or from a different culture, there are those cultural barriers, not that they can't be surmounted, but they take time, they take effort, and the ability to do that is so much more available nowadays than it used to be. And working from home lends itself to that. I suppose there are some companies that only work very locally, but that's really rare.

Just about every company now, even the smallest, they have a supplier in Asia, they have a customer in Europe, they have somebody in Australia that they're working with. And no, they're probably not going to fly to Australia or to Beijing or to London all the time to meet with them.

They have to deal with that in some other way. And the Ability to do that online is so much more powerful now. And then that leans back to the working from home.

Because if you're dealing, you have a call in India, 8 o' clock at night and you got to talk to Europe at six in the morning. So what does that mean? Does that mean you're going to go into the office at 5:30 and you're not going to come home until, you know, 9:30 at night?

That, that's not really a way to live and, and it's certainly not. But if you're working at home, it doesn't matter.

So you get up and you have the European call and then maybe, you know, you have your breakfast and do some things, then you work and then you stop, you have dinner, play with the kids. Oh, it's time for my eight o' clock call with India. You do that, then you come back and go to bed. Yeah. Will life be interesting?

Freddy D:

It's all in one. Sir Richard Branson says it the best. There is no separation between life and personal time or work and personal time, I should say. It's called life.

It's all intertwined. And so you're absolutely correct, Ken.

And I did operate on a global scale, both in the corporate where I was in the office and I would communicate with people by email and we actually did some early video conferencing back in the late 90s. But what I ended up doing was I would have to fly out periodically to meet people in person, all that stuff.

d my own company in the early:

And then at nighttime I would be dealing with the Australian and New Zealand marketplaces. But had I been in an office, you're absolutely correct, there's no way I would have been able to do that.

s was home based in the early:

Ken Taylor:

To your point and to Sir Richard's point about, it's called life. This is not a new thing. We look at it as being new because we have limited lifespans.

But I believe it's actually a reversion to the way that life has operated for most of human history. We've probably all seen the old Little House on the Prairie TV shows from the 70s. Well, think about Pa Ingalls now.

He probably worked harder than any of us. I know he worked Harder than I ever have. And thank God that I don't have to be farming for 12 hours a day. But he wasn't really gone from his family.

Well, sometimes he was. There's one episode where he had to go mining because the farm failed. So he was gone on a business trip, so to speak.

And then he came back, but most of the time he was working. And the girls, they knew where he was. He was, you know, over the hill, plowing the field.

Then they could go out and play with him or say hi to him or he might come back in for lunch with Ma and his daughters or. So the integration of his work and his life and his family and his community too, it was all much more integrated.

We hear about the crisis of loneliness today. I think people too many silos. Well, this is my work and this is my life.

But I really don't have much of a time to do, like, because I'm at work all the time or I'm in my car with nobody, just fighting traffic and cussing out that guy that cut me off. That's not a healthy way to.

And if people are not healthy, if people are not in their best mental state, they're probably not going to be able to do their very best work. Nowadays, we live in a knowledge economy. We need to be on our A game all the time.

And if you're a leader in the business, yes, it's important that you be on your A game. But it's just as important that everybody in your team is able to do that as well.

And it's not just, well, you got to work harder, figure it out, sort it out. That's your own problem. No, no, it's not. It's a problem for the business.

What can the business do to make it easier for the people to be on their A game?

Freddy D:

Yeah, and that's where you wrote a book, Working in Slippers about that. And let's dive into a little bit of that. And. And how did you. Your background, working with remote people, bringing them on board and all that stuff.

So let's talk a little bit about that, Ken, because I think that that's an important area, that it takes a special way to onboard people that are remotely part of the team. And then how do you keep them engaged as a remote team member?

Ken Taylor:

Yes, those are two very important and essential issues that have to be confronted. And a lot of managers, they're just not really familiar with that because that's not how hiring has been done for the last 40 or 50 years.

So let's start with the question of how do you find the right people? Nothing in principle is different from what you would do hiring for being in an office.

But remote work can be less forgiving because when you're in the office, you can see people a little bit more and observe. And maybe people that aren't the greatest, you can lean on them a little harder to improve.

With remote work, they're in their own office, but are they in their own home? You don't see them all the time. So it's absolutely vital to get people that have not merely the basic skills that are required.

That's just a given, but also that have character. We know people think about your own office. If you've worked in an office or worked on a team of any size, you could probably name.

These are the people that are always leaning in. And if something needs to be done, they're going to roll up their sleeves and they're going to do it.

And these are the people that'll do what they're told. But they're always kind of looking at the clock and, you know, when could they bail for the day?

And you got to check on them, you know, did you get that project done? I forgot. Here, I'll get that done. So they, they're productive, okay, they get work done.

They're not totally useless, but they're not a manager of one. They don't really manage themselves. You have to stay on them. For remote work that doesn't really work, you need people that lean in the direction of.

At the very least, I want to do an honest day's workflow, honest days, paid. Now, it doesn't necessarily mean that they work 12 hours a day. Maybe, you know, work the eight or whatever it is that you've agreed on.

But they're going to be diligent, they're going to give you good value for money that they're being paid during the time that they expect to be doing it. And if they get stuck, they won't just, well, I guess there's nothing just to watch some cat videos.

No, they'll reach out to you and say, hey, I have this issue. How can we move forward? And that is something that you have to look for very distinctly in the character of the people that are being interviewed.

Now the next question is, how do you find that? And there's no one good answer. But the way that we traditionally do interviewing and hiring doesn't really cut it.

One way that I found that contributed enormously was having a fairly detailed questionnaire that people had to fill out in the application process with open ended questions. So for example, some questions that I really liked. Here's our website, what do you think about it? Here's our support documents.

What do you think about those? Now there is no right answer. There's no, not necessarily a wrong answer, but you can learn so much about a person.

I like the pretty color of green on your website.

Okay, all right, well we know you're not colorblind, but somebody that writes three paragraphs about, well, you know, here's the layout and this is good. And oh, you have a typo over here and you know it didn't scroll nicely on my particular browser on this computer.

Well, you've definitely learned something about them. Here's somebody that's thorough and diligent and at least is willing to put some time into that.

You didn't specifically tell them, but they lean into it. And what do you think about the support docs?

Well, well, they're well organized or they're badly organized or I had this interesting question and I was looking and I couldn't find it or well, it looks like you have a lot of them that's pretty decent.

Again, you're going to learn about their character, learn about their personality, learn something about how much they care about this particular job and your company and how they would do their work.

And as far as finding a super fan of your business, if your business is of a size where you might actually potentially hire somebody that has used your product previously, well, you'll quickly learn about that and say, well yeah, you know, I love your support times because I was on here the other day trying to find this about what I was using your thing for and I was able to find it or I wasn't or I sort of have found it.

And those kind of things are very key to determine how somebody will work better once they're in your organization on the inside, not just on the outside.

And similarly with the interviewing open ended questions, once you have these questionnaires where they talked about their experience, well, you know, they could have just asked chat GPT to do that. Yeah, they could have. They probably wouldn't have done a great job, but maybe.

But if you take some notes and you start asking them about that and they don't have a good answer, well, you just found, you just sort of caught them out. They just cat GPT the whole thing.

But if you write intelligent questions that are vague enough and open ended enough, AI is going to basically just sort of filibuster and you'll know there's no there there, there's no actual meat here.

It's very easy to tell, at least for me, whether somebody's doing it chat GPT or they actually went through and thought it out themselves, or even if they gave some prompts to the AI and there is some reality there, well, that's where you can talk through it in the interview. And there's not necessarily anything wrong with using AI tools. They certainly do have their place. Particularly not everybody is the best at grammar.

As long as the concepts and the knowledge are coming out of their head, you just use AI to clean it up, that's fine. And you can see that distinction as well between what they sent in in writing and what you're getting from them live on the conversation.

And depending on the job that you're wanting them for, that may or may not matter. If they're going to be on the phone, their ability to talk clearly and communicate clearly live is going to matter.

If they're going to be writing reports or answering email trouble tickets, then maybe that doesn't matter so much. And so the individual person putting their person, the person and their skills that they have in the right seat because nobody is good at everything.

I know nowadays you get these job descriptions where we want somebody that is flawless in every conceivable thing we could ever ask them to do. You know, from writing a sales report to cleaning the toilets. Nobody is like that. Nobody is good at everything. That's why you have a team.

You have this person is good at this, that person is good at that. So give that this thing to do and that person that thing to do.

And if you have to swap them, well, maybe in an emergency you do what you got to do, but you recognize there's going to be issues because those don't speak to their strengths and that's not their fault.

Freddy D:

Right.

So one of the things that I used to do when I interviewed people and brought them on was that I would ask them to describe how that position would be a success. So basically, if you were the manager of that position, what would you define success in that position?

And so what was really cool about that was they would end up writing their own job description and their success of their job. And so then when I applied that approach, they emotionally got connected to it.

And then so my job as a leader as well, Ken, this is what you described would be a success in this position. My job is to make sure you do what you said you were going to do. So you've got ownership of it?

Ken Taylor:

Absolutely. Because if they have ownership of it, they're a lot more likely to do it. And that also gives you.

And this is even more important to remote work and it's important to in office work too.

Freddy D:

But it's also a way of defining that person as to what their thought process is. So it's another. I'm continuing on what you talk about qualifying for the person with open ended questions.

And so that was one of my approaches in the interview was, okay, define how would you determine this job to be success? And how they answered that gave me a snapshot which is similar to what you're doing. I'm just basically elevating what you were.

Ken Taylor:

Talking about, that you have hired people that coming in the door, they didn't necessarily seem like they were the right fit for the position.

But by the time you were done with the interview, the position had changed to suit them because you discovered something that you hadn't thought of that was actually really useful to have in your company.

Freddy D:

Right?

Freddy D:

Yep.

Ken Taylor:

And that's.

Freddy D:

I ended up getting some players that, you know, you didn't anticipate. You know, at first you go, I'm not sure because, you know, we judge a lot of times people visually, you know, and it's just human nature.

And then they start talking.

But then all of a sudden, you know, you give them the opportunity and the ones that you don't think are the ones that surprise you and the ones that you think are going to knock it out of the park usually don't.

Ken Taylor:

Absolutely had that experience. And there's nothing that I really enjoy more than that is finding the diamond in the rough.

Finding someone that has, for whatever reason, never really had the opportunity to let their full talents be brought to bear.

There's no greater pleasure than being able to promote somebody that had not had that opportunity before and on paper would have never had that opportunity. But they proved what they were able to do because they came in and you had that flexibility and they were able to show that. And then it's.

There's no risk. You're not taking a chance on hiring a more senior person. You're simply reflecting what they've already demonstrated that they're able to do.

Freddy D:

Right. And so how do you keep that person that's remote? So let's say you've got a team, you know, that's spread out throughout the country.

How do you keep those people engaged? Because there's still gotta be a corporate office.

What's your approach on keeping those remote people engaged and being feeling like they're part of the organization.

Ken Taylor:

Well, part of this comes to the way the onboarding process. And in a small company, you don't have a lot of formal training. The training sort of grows as you go along and get bigger.

Which means how would you do that in a small, in office company? Well, you might do what we call shoulder surfing, where, you know, you're sitting next to somebody that's doing the job.

With a virtual environment, you can do some of that as well. With zoom, you can have the video calls, you can have the screen share.

Freddy D:

You can 232 inches.

Ken Taylor:

So yes, you put the zoom up on there and then you have the browser over there, you have the chat down there and you're watching and communicating live. It isn't exactly the same as if you're in the room, but it's not that far off.

They're going to establish a relationship with the people that they are working with. They might move around and work with different departments to become familiar with different aspects of the company.

Or even in the same department, you might have one person who's really good at this and somebody else is really good at that. So I want you to hang out with them for a day or two and learn how they do it. What are they doing?

They're building a relationship and then you have the chat. A lot of tech companies use Slack.

I like the Google chat because it comes with the Google suite that most companies are already paying for and therefore it's free. You can talk to anybody in the company.

Now, you're probably not going to bother the CEO every day unless you need to, but you can certainly talk to the people on your own team and you should do that. That should be encouraged. Again, people will have that relationship and it's established. It's human nature. They want to have relationships.

If you give them the ability to and the tools and the techniques and the liberty to do that, they will do that. And yeah, because what you got to.

Freddy D:

Do is you've got to have them feel part of the organization because, you know, at the end of the day, you really want to create super fans of your leadership style from your team. You want your team to look at you as saying, okay, I like this guy. I'm a super fan of this guy who's my leader.

And what I've learned over the years as a good leader is that, you know, if you've got remote people, you want them to participate in the company activities even though they might be remote. For example, you could have pizza coming into the Office. Well, you ship a pizza to the remote person, okay, it's cheap money, very cheap money.

But it's a phenomenal way to that remote person or that remote team that's in different locations. They got a little pizza delivered to them because we're having pizza day at the office. Well, guess what? Now they feel included.

They're part of the organization. They're going to be a super fan of you as a leader because they're going to go, he got me a pizza. I'm participating.

And then you get them on the video. And now everybody's together. And it really creates that synergy because at the end of the day, as we. That's your front line.

Your team is a front line to suppliers, to customers, to distributors. If you're working with contractors, if you're working with complementary businesses, that's the thing. That's who the front line is.

That's your most important resource.

Ken Taylor:

Absolutely.

And if you are not paying for an office for somebody, well, the savings for that will certainly cover a fair bit of pizza and maybe even the occasional trip, you know, physical trip to meet people in person, which I do think there is value to doing that on a periodic basis. Maybe yearly, maybe quarterly. Yeah.

Freddy D:

My wife works for a company.

Freddy D:

She's, like I mentioned earlier, going on eight years. She just came back from a company trip where they flew everybody in from the United States.

I mean, they're a global company, so they do it regionally or country wise. Everybody in for a four day. Then they came in Wednesday night, Thursday they had stuff in the office.

Friday, Saturday they went boating and they went to the Versace house and all down in Miami and all that stuff just to build the camaraderie of being in person and then everybody goes back out. So you're absolutely correct. You need to do that once in a while.

Ken Taylor:

Something else that I found this won't necessarily work with a very large company, but we established tiers of meetings or there each team had a weekly meeting or in some cases a daily meeting. Then department there would be weekly meetings or bi weekly. And then we did have every week on all hands for the whole company.

And most weeks each person would very briefly say what they had done this week and if they had any issues or anything so it could be discussed. And this was a great way for getting across departments, people to understand some concept of what the other team members did.

Now it doesn't mean that everybody was close friends with everybody in the company, but at least you know who they were.

And so if you Run into a problem in your department, you'd have some idea as to, well, you know, I think I better go ask Bob because he was talking about something relating to that in his department. So maybe I can get some useful advice there. And that's the kind of thing that you would get.

You talk about, well, if you're in the office, you run into somebody in the hallway, you can create the equivalent of that through adroit use of common meetings and of chat groups and things like that. So that there are ways of doing that. You don't need to keep people silent.

If you're thinking of somebody while they're working from home, they never talk with anybody except their boss, then you're doing it wrong. It doesn't need to be like that. It shouldn't be like that.

Freddy D:

Yeah, I use my wife as an example because she's, you know, they use Zoom for their chat tool. And so they'll either do a quick video with a co worker or they'll chat or whatever.

But she's built relationships with not just the management team and the owners of the company, but she's also built relationships with other players within the organization, to your point. And even though she's remote, she's built friendships remotely with people.

When they do get together, they hang out, go to dinner and all that stuff, and they have a lot of fun.

So, you know, if you structure it correctly with the thought process of creating an ideal environment for your team, your team's going to really take off. Because the team is everything. That's the front line.

Ken Taylor:

Yes. In fact, here's another point that is something that we realized.

When you have a fully remote business or a business with a lot of people that are remote, they might live wherever they happen to live, and in the nature of relationships with other people, they'll mention where they live. And sometimes people like to travel or they go someplace.

They might find themselves in the city where a coworker lives just for their own vacation or their own reasons, but they happen to be there. And a policy that we established was if you're in that situation, you want to meet up with a coworker, go have dinner on us. Company will pay for it.

Now, they're bound to talk about business at least a little bit. So it makes it tax deductible. It's a legal expense.

And even if they go, you know, to Morton's, the most expensive steak dinner is still nothing compared to what a business trip would cost. One restaurant that gives the opportunity for the camaraderie to build more and also for people to feel cared about.

Freddy D:

But that's how you're creating super fans of the team. Because you say, okay, you know what? Yeah, you guys won. We hit the numbers. We were going for or whatever the objective was and we accomplished it.

All right, we're taking everybody out to Wharton's as an example or whatever. And you're absolutely correct. That's cheap money for the goodwill that you're creating from that team.

Ken Taylor:

Absolutely. A lot of companies view that as a reward, especially in sales season. Well, we're all going to Singapore. That's the reward for the top performers.

Yeah, that's expensive.

Freddy D:

I get that.

Ken Taylor:

But for something that's cheaper, like a dinner, even if it is an expensive dinner, it's an investment for the company. I think the company will get back more in team camaraderie than the bill.

Freddy D:

Oh, absolutely. And it goes, you know, you can take that further and that's that.

A lot of times companies are short sighted because, you know, Aunt Lucille is in the hospital. Well, I'm sorry you need to be here for eight hours. Well, I'm, you know, Aunt Lucille's not doing very well. Get out of here. Go visit Aunt Lucille.

Because again, that's cheap money. And don't worry about it, we got you covered. You're getting paid for it. Again, that's cheap dollars.

But now you just create a super fan who will go around and tell her family, my boss, my manager and my company are letting me go. And more importantly, I'm not getting docked for this.

They're going to have a whole different mindset of their outlook on the company that they're working with.

Ken Taylor:

That's absolutely true. And remote work naturally lends itself to that. Think about the situation which your air conditioner blows out or your kid wakes up with a fever.

Well, I got to call into work. I got to stay home and take care of the kid or the AC guy has to come. Well, if you're remote, work it. It doesn't matter.

What do kids want to do when they're sick? They're just going to lie there in bed anyway or watch tv. Yeah, you need to be there, but you don't need to be with them.

You're just in the next room over. So you're still working. It doesn't hurt the company. Well, I do need to go visit Aunt Lucille.

Probably aren't going to spend eight hours in the hospital. You just bug out for three hours. You visit Aunt Lucille, you come home. Well, there's only half a day left.

It's not worth driving two hours of commuting to the office. You're working from home, you're still going to get a half day of work in. The boss might not even notice.

It might just be, you know, I'm going to be in late today because I'm going to go visit Aunt Lucille at the beginning of visiting hours and then I'll go back to work and.

Freddy D:

Work till 9 o' clock at night to make up for it.

Ken Taylor:

One of the things the policies that owner has had, which I think is valuable and good, and a lot of other tech companies that are remote do the same, is they don't even have a leave policy. They call it the unlimited leave policy now. No, that doesn't mean you could just disappear to Australia for three months. No, you'll lose your job.

Freddy D:

I can't.

Ken Taylor:

You have to have some coordination.

But as long as people are professional and coordinate and talk about what they're doing and don't just vanish, then, yeah, we're not keeping track of it. What? We're not. You only have five minutes of leave. You know, we're going to document by five. Borrow.

Come on, feeds back into picking the people that lean into the work, they want to do the work. They want to be diligent, but they also care about Aunt Lucille. Well, let them work it out. Everybody's going to be happier. Right.

Freddy D:

So let's dive in into a little bit of the book here. And what made you write the book? What's about and where can people find the book?

Ken Taylor:

Well, I've been in and out of remote work for my whole life, one way or another, and I just sort of felt that was the way that I was.

But then when Covid happened and all the office people were forced to do it from home without really any warning or training or real knowledge of how to do it. And then at the same time, I was building and developing a business that wound up revolving around fully remote work.

I felt I've had to develop these techniques that I think work pretty well. And there's a lot of other companies out there that are struggling, that they haven't really figured out how to do it.

And now we see companies saying, well, you know, Covid's over everybody back to the office, really. But you just did it for the last three years and you didn't go bankrupt. I mean, obviously it works.

Well, maybe that's because you didn't know what you were doing, which is fair because you weren't trained.

So I decided that documenting the Things that I had learned and getting it out there into the woods world gives people the ability to study it and learn a little bit and maybe make some arguments with their bosses or learn how to be a better manager and be more productive and be better for the teams and for the business. Look, I'm going to save money for the business and I'm going to have happier employees. That doesn't cost us anything.

What's not to like to share people and make a better world and more successful businesses. So that's what I've at least tried to do to start this conversation. I'm sure I don't have. Every last answer in my book is not that thick.

But it'll ask many of the right questions and put you on the right paths to look at things in a new way and think about it that applies to your business. And how can you use these techniques in your particular realm to benefit you and what you're doing? And it is, it is published.

You can actually get it at any of the major. You can get it on Amazon, Barnes and Noble. I'd love to see a review from you posted to Amazon. I certainly read all of those.

They're very important, certainly for getting the word out there.

You can also go to workinginslippers.com and that is the website that my publisher has put up and if you order a copy, you can also get an electronic copies as well.

Freddy D:

Excellent. We'll make sure that that's in our show notes as we kind of come to the end here. Ken, it's been a great conversation, great insight.

Ken Taylor:

Maybe we'll do another follow up someday.

Freddy D:

Yeah, I'd love to have you on the show down the road anytime. All right, we'll make sure all the information is in the show notes and that's the best way to contact you.

Ken Taylor:

You can connect with me on LinkedIn.

Freddy D:

Okay, we'll make sure that that's in show notes as well.

Ken Taylor:

Yes, thank you. And I'd love to hear from your thoughts and experiences. Is how is the remote work working at your company or in your organization?

Is there anything I can do to help? Maybe I can consult or advise, give you some arguments to make your case. Great.

Freddy D:

Thanks for your time, Ken. Great show. And we will talk to you again down the road.

Ken Taylor:

Thank you all for today.

Freddy D:

What a great conversation with Ken Taylor. His journey reminds us that remote work isn't just a convenience, it's a leadership strategy.

When you focus on hiring people with character, clarity and ownership and you intentionally build connection even across distance. You don't just create a team, you create trust, loyalty and performance for service based business owners.

This matters because your people are the experience. When your team feels seen, supported and empowered, they show up as true ambassadors for your brand.

And that's how superfans are built from the inside out. If you enjoyed today's conversation, make sure to hit subscribe so you don't miss future episodes.

Freddy D:

If you're tired of growth that keeps.

Freddy D:

Resetting instead of compounding, start with the Service Providers Prosperity Playbook.

I wrote it as a hundred plus page, step by step guide for service business owners who want predictable scalable growth without chaos, burnout or guesswork. It's built from decades of real world experience, aligning people, processes and profitability so momentum finally works for you.

No fluff, no theory, just proven frameworks, clear examples and strategies you can apply immediately so growth becomes sustainable and your business starts working with or without you.

Freddy D:

You can get the entire playbook free.

Freddy D:

When you join the Entrepreneur Prosperity Hub on school. The hub is free to join and designed to help you activate what you learn, not just read it.

Join now at school skoo.com eprosperity hub and start building momentum that compounds.

Freddy D:

Thanks for tuning in today.

Freddy D:

I'm grateful you're here and part of the Business Superfans movement. Remember, one action, one stakeholder, one super fan closer to lasting prosperity.

Intro/Outro:

We hope you took away some useful knowledge from today's episode of the Business Superfans podcast. Join us on the next episode as we continue guiding you on your journey to achieve flourishing success in business.

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About the Podcast

Business Superfans® The Service Providers Edge
Leadership and growth strategies to scale service-based businesses with People, Processes, and Profitability.
Running a service-based business is hard. Most owners — in the trades or professional services — struggle with the same problems:

- How do I get more of the right clients without spending more on marketing?
- How do I find, keep, and motivate great people?
- How do I stop being the bottleneck in my own business?
- How do I fix my broken systems and get my time back?
- How do I raise profitability when costs keep rising?
- How do I use AI without feeling overwhelmed?

If you’ve asked yourself any of these, this show is your missing playbook.

Each episode reveals how to align People, Processes & Profitability so you can scale smarter, lead stronger, and build a business that runs with consistency, clarity, and sustainable profit — not chaos.



As the author of Creating Business Superfans®, your host L. Frederick Dudek (Freddy D) delivers lively conversations with global founders, CEOs, sales and marketing leaders, culture architects, and SaaS + AI innovators — plus solo episodes where he breaks down the playbooks, mindsets, and systems service-based entrepreneurs need most.



These insights help you turn your team, clients, and partners into unstoppable advocates — what Freddy D calls Business Superfans® (think sports-team superfans): your ultimate growth engine.

Freddy D has lived the climb. After leaving home at 17 and working multiple jobs to finish high school, he rose from draftsman to global sales and marketing director in the emerging CAD/CAM industry, helping grow a software platform from zero to millions. In 2023, he added $1 million in revenue to a 30-year-old service business and positioned it for a successful acquisition.



Tired of brainstorming by yourself? Join the Entrepreneur Prosperity™ Hub—a free-to-join Skool community for service-based entrepreneurs who want clarity, support, collaboration, and a proven path to sustainable growth. Join today!

Get Frederick’s book at https://linkly.link/2GEYI
Join the Entrepreneur Prosperity™ Hub at https://linkly.link/2KjG3
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About your host

Profile picture for Frederick Dudek

Frederick Dudek

Frederick Dudek, author of the book "Creating Business Superfans," and host of the Business Superfans Podcast. He is an accomplished sales and marketing executive with over 30 years of experience in achieving remarkable sales performance results in global business markets. With a successful track record in the software-as-a-service industry and others. Frederick brings expertise and insight to help businesses thrive., he shares invaluable knowledge and strategies to create brand advocates, which he calls business superfans, who propel organizations toward long-term success.


Born in rural France, Frederick spent summers on his grandfather’s vineyard in France, where he developed a love for French wine. As a youth, he showed a strong aptitude for engineering and competed in drafting and design competitions. After winning numerous engineering awards, he became a draftsman working on numerous automotive projects. He was selected to design the spot weld guns for the 1982 Ford Escort car. That led to Frederick joining the emerging computer-aided design (CAD) and computer-aided manufacturing (CAM) industry, in which he quickly climbed the ranks.

While working for a CAD/CAM company as an application engineer, an opportunity presented itself that enabled Frederick to transition into sales. It was the right decision, and he never looked back. In the thirty-plus years Frederick has been selling, he has earned a reputation as the go-to guy for small companies that want to expand their business domestically or internationally. This role has allowed him to travel to over thirty countries and counting. When abroad, Frederick’s favorite pastime is to go exploring for hours, not to mention enjoying some of the local cuisine and fine wines.

Frederick is a former runner and athlete. Today, you can find him hiking various trails with his significant other, Kiley Kaplan. When not writing, selling, speaking, or exploring, he is cooking or building things. The next thing on Frederick’s bucket list is learning to sail and to continue the exploration of countries and their unique cultures.