From Gym Owner to Remote Tech CEO: Kaleda Connell


Today I talk to Kaleda Connell. Kaleda is a former CrossFit gym owner, a Two-Brain Business Mentor, and the CEO of the web design and marketing automation company Gym Lead Machine, which is in the process of expanding into a gym management software platform called Kilo.

Today we talk about what its like to go from gym ownership to the CEO of a startup tech company, what she’s learned in these last couple of years that have helped her grow as a leader, and her secret hack for a better work/life balance.

1:46 – The learning curve to become a tech CEO

5:45 – Managing staff and communicating

11:12 – Rapid growth of Gym Lead Machine

14:08 – Working with focus and intention

19:23 – Kaleda’s superpower

24:10 – Hack for transitioning from work frame to home frame

26:48 – What’s Next? What is Kilo?


Tiffy (00:04):

I’m Tiffy Thompson and Women In Fitness Business is my deep dive into the industry from the female perspective. In each show, I talk with fitness entrepreneurs, coaches, and executives about why they got into the industry and what’s keeping them there. I ask about the unique challenges for women in fitness, the balancing act of career and family, and the different strategies for success in a tough field. I’ll present big wins, lessons from failure and real conversations with real women who are improving the health of their clients around the world. It’s a spotlight on the great work of the women who know working out. Hey, I’m Tiffy Thompson, and you’re listening to Women In Fitness Business. Today, I talked to Kaleda Connell. Kaleda is a former CrossFit gym owner, a Two-Brain Business mentor and the CEO of the web design and marketing automation company, Gym Lead Machine, which is currently in the process of expanding into a gym management software platform called Kilo. Today, we’re gonna talk about what it’s like to go from gym ownership to the CEO of a startup tech company, what she’s learned in these last couple of years that have helped her grow as a leader and her secret hack for a better work-life balance. Hey, Kaleda, welcome to the show.

Kaleda (01:23):

Thanks so much.

Tiffy (01:25):

So you’ve been a gym owner, you retired early at a fairly young age, and now you’re the CEO of Gym Lead Machine in a landscape where women are really underrepresented as CEOs. What does it take to be one? And what have you had to learn?

Kaleda (01:46):

That’s a super tough question. And I think it really depends on like the industry that you’re in, the business that you’re running. And I think it’s really just gonna depend on the person, too, but I think like there’s a couple of, you know, kind of hard and fast skills that you should learn going into management of any kind. You know, I don’t really think it’s particular to women. Although I think maybe this is a little bit difficult for women cuz we tend to like take on a lot and you know, think that we can do it all and quite honestly we can, but I think for us, like you really need to figure out like how to create your own opportunity, right? So no one is going to create the opportunity for you to level up in your career or for you to, you know, take that next step or become a CEO.

Kaleda (02:48):

You have to create that for yourself. And so it’s about putting yourself in the right position and saying yes to the opportunities that get put in front of you. You know, there’s a lot of times where, you know, I was away from home and I was, you know, traveling a lot and making sure that I was putting myself in the spot where I knew I’d be seen. I knew my work would be appreciated and you know, I could get to say yes to the next opportunity. And I think like a couple other things, you know, if you’re not confident in your work, if you’re, you know, questioning like, did I do a good job or, you know, when you present something to somebody be like, you know, I made this for you. Here’s what I have for you and deliver, it right.

Kaleda (03:35):

And be confident, be confident in your own work. And I think that’s really important and it takes time to get that skill. because you know, we question ourselves a lot. Are we doing the right thing? Is my work any good? But I think if you’re confident in your work and presenting that to someone, you know, they’re gonna see that it’s good work and they’re gonna see the opportunity, essentially that next step for you be like, oh, you’re the right person for that next job. And then I think the third thing, you know, that I thought of when I was reviewing the questions that you sent to me was, you’re setting others up for success. So if you’re able to empower others to grow in their jobs, like you are going to grow in yours, right?

Kaleda (04:29):

So managing people is about managing people and making them successful. And the more you make others successful, the more that you are able to level up in what you’re doing. And like a specific example of that is something as like one of my favorite things to do, which is writing an SOP. When we first started Gym Lead Machine, we didn’t know, to be honest, we didn’t know what we were doing. We had a pretty good, you know, idea, but none of it was on paper. Me and like two other people spent countless hours on zoom, just kind of like figuring out the process and making mistakes and, you know, sometimes you’d have angry customers and that’s OK because they were helping you, you know, develop these SOPs so the next time that this didn’t happen. And so we were able to get to a point where those people felt empowered and I could work on the next thing. And then once you get that level empowered, you can level up again and start to work on the things that matter most to the business.

Tiffy (05:32):

How much did your experience as a gym owner impact your skill development and growth as a CEO?

Kaleda (05:45):

It’s tough because those are two, like really, really different businesses. You know, running a gym, you have to essentially be there every day. Running a remote company, you can be wherever you want and you don’t know where your staff are. And if you’re, I don’t wanna use the term micromanager, but if you’re a manager who likes to see your staff work, I mean, that can be hard to figure out. So I think it helped for sure. I mean, I had Chris Cooper as my mentor, in both situations. So, that was helpful. I did learn how to manage staff. I learned how to empower people, you know, through systems and processes and make sure that they felt like they knew what they were doing on a regular basis. And if they didn’t, they knew where to find the answers instead of, you know, waiting for me to show up every couple of days. So that’s good, but it didn’t help me figure out how to asynchronously communicate with staff. And it didn’t help me figure out like, you know, how to run a tech company or how to run a remote company, anything like that. So those are skills I’ve had to learn. But I will say like the management of people, I think, no matter what business, either if it’s your own business or a different business that you’re managing a group of people, will always be a good transferable skill.

Tiffy (07:20):

Chris talks a lot about the love and loathe list, making a list of the tasks that you really love to do and wanna do more of. And then the loathe list. Has that love section gotten bigger as you’ve grown in your career? Or how has that sort of played out?

Kaleda (07:38):

Yeah. These are hard questions, you’re asking all the hard ones. I think, like as you start every new business, like, you kind of start at the bottom each time and you’re gonna do stuff that you don’t wanna do. So when I ran my gym, you know, I did all kinds of stuff I don’t like to do. Like, I’m not a particularly good coach, I’m funny in classes and I can entertain people, but I’m not technical. And I knew that. And so being able to get somebody in that liked to do a little bit more technical coaching and that kind of thing was really beneficial cause I could take that off my plate. I think no matter what job you’re in and no matter what level you’re at, you’re always gonna have some stuff that you loathe. And maybe loathe is a strong word, but stuff you dislike doing.

Kaleda (08:34):

When I was ready to sell the gym, like there was not a lot of stuff on my loathe list just because I had gotten to the point where I didn’t have to be there every day, I could do the things I really liked to do, which was like manage the backend stuff, manage my team. I loved managing my staff. I still love managing my staff, but I really, you know, I liked my team there at the gym. So that was really cool. But then you move into a new business and it’s startup and you’re back down to, you know, what Chris calls the founder phase. And so you’re doing everything. And like I said, this is very different, you know, it’s not only my business. So, you know, I have two founders that I have to report to and that kind of thing.

Kaleda (09:28):

So like, I don’t really have the luxury of taking a lot of everything that I dislike off of my plate. I don’t have the luxury of, you know, I typically use the love and loathe list with employees because they’re specialists and CEOs or upper level management are usually generalists. So you do have to kind of do some of those things you don’t like doing, although I will say, you know, I’m in Brazil right now. I’m not in cold Canada, so that’s pretty great. And there are a lot of things I love about, you know, being remote and being able to, you know, run the business at a high level. I don’t particularly like doing little stuff, you know, like reviewing metrics and, you know, like preparing the monthly town meeting, like they’re like tiny little jobs that just kind of like add up. And I had an assistant and I recently lost her. So I have to do those things again. But at the same time, I’ve kind of realized like, those are really important things for me to do, because if I’m not paying attention, you know, I’ll get a report sent to me and be like, whoa, what is happening there? So I kind of changed my mindset about the love loathe list a little bit, because I know it’s super important for me to do some of those things.

Tiffy (10:53):

It’s been a admittedly hard year for gym owners who you primarily work with. What have you learned in this, like over this pandemic period, that’s kind of helped shape who you are as a person and how you’ve grown as a leader.

Kaleda (11:11):

So through the pandemic, like we had to move very quickly. When we first started Gym Lead Machine, of course there was like a little bit of talk of COVID. But we didn’t like everybody else in the world, or most people in the world, we didn’t think that it was gonna become such a big deal. Right. So when we met in December and January, me and my team, we kind of laid a plan, a growth plan of how Gym Lead Machine was going to grow over the next year. And our plan was to do five websites a month. We’re only gonna sell five a month. it might have actually been four cause we were gonna do one a week. And you know, everybody knows when America shut down and, you know, I was in Berlin when that happened and I had to figure how to get home.

Kaleda (12:06):

And like we were in a crazy time. And so I finally was able to get home and Canada, you had to quarantine for two weeks. And so that was great for me because we decided that we were just gonna go full steam ahead. And we ended up selling four websites per day versus four per month. And so we really had to figure out what was absolutely essential and only deliver on those things. And so we like really pared down and like trashed all the unnecessary. And so it was really cool to see the team come together and figure out what do we need right now in order to serve gym owners best and what can we like wrap and what expectations do we have to set for these gym owners that are coming on board. So they know exactly what we’re going to deliver now and what we will deliver on later.

Kaleda (13:06):

And so that was really interesting, like figuring out what to say yes and say no to, and trying to explain that well, and I think, you know, for any business, like looking back, I think, wow, I wish I would’ve done that for my gym when I first opened, like only offer what’s absolutely necessary right now, and then build on that later. And it’s made me a better mentor at Two-Brain, it’s made me a better CEO when we launch new products, and really like paring down that offering to only be essentials and then setting the right expectations for clients has been a really interesting and cool experience.

Tiffy (13:50):

That’s really interesting. Like a lot of the stuff that Chris is doing now is very pared down and intentional and I think it leads to people getting better, faster results because they have that focus. Is that what you find?

Kaleda (14:08):

Yeah, it’s absolutely correct. Like, you know, have a plan of what’s absolutely necessary. And I think, you know, I used to run the Two-Brain Marketing course mentors as well. And I would take on clients that had issues, right. Because, you know, just like any like program or any, you know, you have this with the gym, people aren’t seeing results when they sign up with you, they’ve spent $400 and they’re like, what the heck? Right. And so you have to have someone on a team that can take on complaints and problems. And that was me. That was my job at that point. And so I would take on some clients that hadn’t had optimal results and we would take a look at exactly what they were doing. And I would find things like, oh, so you added this to, you know, your marketing copy, or you used this photo or you used, and they kind of strayed from the program.

Kaleda (15:08):

And so what we had to do was like, rile them back in and say, I only want you to do exactly what I’ve laid out for you. If this does not work, then we will try different avenues. Right. But let’s like stick to the basics. Let’s stick to exactly what the plan is. And then let’s branch off. And I think like, and it worked usually like nine times outta 10, it would work. And so, you know, you’ll, as a manager, you’re gonna have staff that’ll say like, let’s do this, let’s do that. And their ideas are all usually really good, but we have to figure out what to say yes and what to say no to, in order for, you know, that quick growth that a lot of companies want.

Tiffy (15:53):

Kinda spell it, like what do you do every day? And like, are you in your perfect day? Essentially every day? Like, it sounds pretty idyllic to me. Being able to work, live and work wherever and have that flexibility.

Kaleda (16:09):

Yeah. You know, there there’s a lot of times like there, people will ask me like, oh man, like running your gym must have been like, so great. You like work whatever you want. And like train whatever. Yeah. But the reality is like, that’s not true. You know, when I ran my gym, like I was so busy that I didn’t have time to work or eat properly and I gained a lot of weight, that is not, you know, typically what people would think that would happen when you start a gym. But this is a little different, I mean, I’ve had a go or two around, so, you know, figuring out, you know, what I wanna do every day and you know, how to get it done is, has been difficult, but it’s become easier, you know, over the last two years, once you get staff and systems in place.

Kaleda (17:00):

And I mean, this is the quickest I’ve ever grown a business. So, on a daily basis, I guess, like it’s usually putting out fires and having meetings, right. Like any CEO that you talk to, they’re just like, yeah, I just do meetings all day, but there really is like, you’re unblocking people a lot of the time. Right. So you’ve got direct reports and you’ve got, you know, their reports and they will have questions that they might not know how to answer or problems that they dunno how to solve. And it’s up to you as a CEO or a manager of any kind to unblock those people. And so you’re the decision-maker most of the time. Right. Cause people are just bringing you problems all day long, all day long, and you have to have good judgment in order to solve those.

Kaleda (17:48):

And most of the time you do have good judgment, some of the times you don’t and that’s OK because you’ll learn from that. But yeah, like, you know, in terms of like details of what I actually do, you know, like I answer a lot of emails. I live by my Google calendar. It really does change, you know, the time of year, the products that we’re offering, you know, what we’re doing, for example, we’ve acquired five website companies over the last two years. So I mean, that’s another learning experience. Like I had never acquired a company before. And after the first one, you know, we created systems around how we were gonna do it and they’ve evolved and grown after that. And every time we acquire a company, you know, I don’t want anyone to feel like, Hey, Gym Lead Machine just bought like this company, like our service is gonna get worse.

Kaleda (18:43):

Like I should jump ship or whatever. So I offer meetings to every single one of those people that we’ve acquired their websites so that they can put a face to the name. And so that I can put a face to the name. Like we’re not this like faceless company that doesn’t care, if that makes sense. So some weeks, you know, I’ll have 20 meetings, 20 30-minute meetings with some gym owners, which is awesome. Right. Like it’s exactly what I wanna do. So it’s very tiring, but it’s awesome.

Tiffy (19:18):

What would you say is your super power as an entrepreneur?

Kaleda (19:23):

It’s organization. Like, yeah. If you’ve, you know, listened to other podcasts or read anythin that I write, or if you know you’re involved in the Two-Brain world in any capacity, you kinda know that I like to write SOPs, which sounds like the most boring thing on the face of the Earth, but it’s really my happy place. You know, I can just like put on my like flow electro music and just really like figure a process, right. And it’s not because I want our company to be overprocessed, because that’s not fun either. And doesn’t allow for a ton of creativity, but I do want people to know what to do. Right. I want them to, and I’ve said this before, I’ve said this so many times, but your staff will feel empowered if they know where to look for the answer to their question. Right. And eventually you won’t need the SOPs quite so much anymore, but it makes it really easy to train people. It makes it really easy to take a holiday. It makes it really easy to have management like, and have those layers if you’ve got those systems in place. So yeah, it’s, I guess just.

Tiffy (20:38):

It takes time to do, but you’re buying yourself time later, basically.

Kaleda (20:42):

Yeah. Like when we first started Gym Lead Machine, I remember like we would try and have our staff like work as regular hours as possible. You know, with remote staff, it’s hard to tell when people are working, which is like good and bad, right. These people are adults. I don’t wanna babysit people. You know, I have nieces and nephews for that. But I really wanted like them to feel like they could work whenever they wanted, but I was working, you know, on the front lines from nine to five. And then like to bookend my day, I’d be up at, you know, four or five, six in the morning. So I could write, you know, at least one, like FAQ answer to a question or get like some kind of process built out from a question that had been asked yesterday so that they don’t have to ask me again. Cause n’t with a remote company, people don’t, they’re like, oh, sorry to bug you. Oh, sorry. You know, I know you’re busy. It’s like, no, I want you to ask these questions so I can process this out for you. So you feel empowered to do your job.

Tiffy (21:55):

Have you read anything or listened to any podcast or anything recently that’s kind of resonated with you?

Kaleda (22:00):

The Jason Fried books. Acouple of them that I’ve read it, wasn’t super recent. It was maybe six months ago or something like that, but “Remote” and “Rework,” and they’re both very similar. So, you know, if your listeners decide to read these, like you can read one and get most of what you want out of them, but, they’re really like, they kind of flip and maybe not now with COVID, you know, transitioning a lot of companies to more remote work, but at the time that they were written, it did sort of flip the traditional workday and work style on its head. And it was honestly, it was like comforting for me to read these and be like, oh, you know, you don’t have to be online 24 7. Like you can block off time to get things done. You can like offer these like interesting and fun things to your staff. And I realized that the hardest thing in running a remote company was getting your staff to stop working.

Tiffy (23:08):

Hmm. Interesting.

Kaleda (23:09):

Yeah. So because, you know, I give them the flexibility to work when and wherever they want to, sometimes they will overdo it. Right. And I don’t want them to get burnt out because that’s what many of us have seen, it’s a very real thing that can happen. And if you don’t protect yourself and you don’t protect your staff, it will happen. And people will be unhappy and it’s very real and it’s probably happening in every single company in the world right now.

Tiffy (23:43):

Are you able to do that for yourself though? Create that delineation between work and off time? Because I personally find it really difficult, especially if Slack’s on your phone, you know, it’s always kind of just running in the back of your mind, like a computer program an it’s very hard to of shift gears. Do you have any hacks for doing that or have you figured that?

Kaleda (24:10):

I have one. And it’s on your cell phone. So, well, I actually, like, there’s some things that I do to get myself away from work and make myself happy. And one is like, have somebody in your life that likes to take holidays and forces you to do it. So that’s been great. But the other that’s on your cell phone is like, there’s a sleep mode or a focus mode on your cell phone and it will actually shut all of your apps off after a certain time. And I’ve done that. And it’s awesome because when you click on the app to like, we use base camp for all of our communication and at Two-Brain we use Slack at, you know, GLM, we use base camp and other things, but, you know, when you go to click on that app, it’ll actually a little notification will come up and it’ll say like, do you want to unblock this or whatever for one minute, 15 minutes or nevermind, and I’ll click it out of habit and then I’ll realize what I’m doing and I’ll hit nevermind.

Kaleda (25:14):

So it like makes you more conscious about what you’re doing and when you’re doing it. So mine shuts off at seven. They used to shut off at eight, maybe in few months I’ll get to six.

Tiffy (25:27):


Kaleda (25:28):

And then the other thing is like, do something for fun. Like figure out what you like to do and do something for fun. And honestly, I haven’t had a hobby in years, because CrossFit was my hobby and then I had a CrossFit gym and it was no longer my hobby. It was work. And so I didn’t understand, I didn’t know really what a hobby was like. Yeah. You know, we used to play soccer in school and we used to like, do all these things, and now you’re an adult and you like, don’t have time for stuff. It’s cause you’re not making time. Right. So like for me, I take language classes twice a week for two hours and like, I know I have to focus and I know that like, it’s something that I really enjoy even though it’s kinda late at night or whatever, it’s not an ideal time of day. I just make sure that like, you’re focusing on this and I’ve made new friends and like, I feel like I’m learning again. And it’s exciting. And even though I’m trash at it, like it’s super great. And like getting you away from work.

Tiffy (26:30):

Yeah. So where is I have a final question. Where is Gym Lead Machine headed? And can you tell me a bit more about Kilo? I’ve heard whispers about this company.

Kaleda (26:44):

You’ve heard the rumors.

Tiffy (26:47):


Kaleda (26:48):

So GLM, like for people who don’t know, like we build websites and automation software for gyms, like our customers are like super small, maybe not super small, but smaller gym owners. And we created this company because we wanted small gym owners to be able to compete with the well-funded competition. Right. So we know that well-funded competition like these big box gyms, like they can outspend us in a matter of minutes. Right. And so gyms in our realm need to be able to work smarter and not harder. And so we spend a lot of time figuring out how to make gym owners’ lives easier. Like it’s as simple as that we make gym owners’ lives easier. Now in terms of like where we’re headed, you know, we we’re building software, we’re building software that makes running a gym easier and more profitable.

Kaleda (27:51):

And that’s our vision for the next, you know, foreseeable future. Which means that we’re going to be adding to our stack, and Kilo is a gym management software that is super brand new. You know, really we’ve only told our clients about it. So this is like the first public announcement about it. So you got that one. It’s in development. We are taking our first testers, we’ve got five people picked out to test the software and we’re really excited, you know, all of us, myself, John and Mateo, we’ve all been gym owners. We’ve got staff that have either worked in our gym or have owned gyms themselves or worked in other gyms. And we all know how difficult is to use some of the management softwares that are out there, right. They don’t give you what you need in order to actually run your gym on a day to day basis and make decisions that are important for your business. I mean, I don’t really care how much money I brought in yesterday. That’s not a meaningful metric, but what might be meaningful is figuring out, Hey, what’s my least attended class over the last, you know, four months and should I cancel it?

Tiffy (29:14):


Kaleda (29:15):

Or, you know, what’s my revenue today compared to a time period that I actually care about. What’s my goal for this quarter and how close am I to hitting that? And being able to see those things like at a glance is ridiculously important and we haven’t seen it in other software.

Tiffy (29:35):

So when do you have it slated for release tentatively?

Kaleda (29:41):

So tentative release will be for the Two-Brain Summit, which is the beginning of June. So we hope to have something ready to launch. I mean you know, if you paid attention, during the last, I don’t know, 30 minutes or so here, you know, it’s gonna be a product, but it’s gonna be pared down, right. That only has the essentials and we’ll lay out the expectations as well. But, as with any software, it’s just gonna continue to get better, right? So while it may not have every single piece of functionality that, you know, you might wish for in a gym, it’s gonna have the pieces that you need and it’ll continue to get better and better. And we’ll be able to take gym owners’ wishlist and actually act on them as well.

Tiffy (30:26):

Very cool. I’ll be looking forward to that. Thanks for joining me today. It’s been a pleasure as usual.

Kaleda (30:34):

Thank you. Thank you for having me on, this was fun and, I’m sweating now cause it’s very hot. If you’re in Brazil.

Tiffy (30:41):

Well and enjoy, are you headed to the beach later?

Kaleda (30:45):

I dunno what we’re doing later. It’s a free afternoon.

Tiffy (30:51):

And it’s not minus 20.

Kaleda (30:53):

That’s right. It’s not minus 20 and there’s somewhere. So we’ll get some of that.

Tiffy (31:00):

Thanks, Kaleda. Take care.

Kaleda (31:02):


Tiffy (31:05):

Thanks for listening. For more episodes, subscribe to Women In Fitness Business wherever you get your podcasts.


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Women in Fitness Business is Tiffy Thompson’s deep dive into the industry from the female perspective.It’s a spotlight on the great work of the women who know working out.

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