049: Want a DREAM Job? Listen To This Now

The difference between business survival and failure often comes down to one thing: the people you hire. In this candid conversation, we dive into why grit beats impressive resumes every time.

Our guest, who built and sold two companies before 40, shares how their hiring philosophy evolved through both wins and hard lessons. "I'd rather hire someone who never says, ‘That’s not my job’ than a billion-dollar executive who won’t roll up their sleeves," they explain, recalling hires who looked great on paper but crumbled under pressure.

This mindset became crucial in their latest venture—a "COVID baby" launched in late 2020. What started as a freemium product backed by venture capital had to pivot fast when economic shifts hit. Converting free users to paying customers and downsizing twice in a year were tough calls, but they stabilized the business and kept the vision alive.

Perhaps most revealing is their take on life post-exit. Despite financial freedom, early retirement felt empty while friends kept working. That restlessness pulled them back to entrepreneurship, scouring forums for real problems to solve. Three years and $12 million later, they’ve built a solution tackling industry-wide challenges—proving that persistence, adaptability, and the right team can conquer even the toughest business hurdles.

Colin Knox on LinkedIn:
https://ca.linkedin.com/in/realityknox

Gradient MSP:
https://www.meetgradient.com

Chapters

• 0:16 Hiring for Grit Over Experience
• 3:26 Taking Chances on Young Talent
• 6:57 Lessons from Bad Hiring Decisions
• 8:41 Covid Challenges and Company Pivots
• 12:49 From Free to Fee-Based Model
• 16:05 Life After Selling a Business
• 19:41 Building a $12 Million Solution

Transcript

Speaker 1: 0:00

you know, hiring somebody from their accolades of previous accomplishments, or or you know things that had allegedly been accomplished or whatever, both in this business and in the last one, you know, and and realizing that, oh, that's a person that just comes in to manage and isn't willing to get their hands dirty and isn't willing to to actually run like they. They could manage a team just fine, but hopefully this thing is all just rolling Right, um, and so, yeah, I mean it's, it's come down to that. I think, at any point in any business I have now or in the future and it doesn't matter how big it is I will always, always go for grit now and and willingness to dive in and do anything, and willingness to dive in and do anything.

Speaker 2: 0:46

I'm impressed. It sounds remarkable and, like I said, just trying to imagine you're talking about the people that really said this is kind of like their first full-time position working for your organization. And you say A players. I'm thinking about what history we're using to identify them as an A player, when you brought them in.

Speaker 1: 1:04

I was cheap, seriously right. Identify them as an airplay player. When you brought them in, I was cheap, seriously right. Everybody, even where we live, right, so I'm, I'm in western canada and in alberta and a very predominant oil and gas economic environment here right, it's, it's you. Calgary is called Cowtown, it's farmers and oil and gas, right, like, that's what it is. So I mean, to find somebody that builds software and wants to join a software company that's not in that industry was difficult, and so you had to go to young, you know fairly new grad, dynamic people that just had that twinkle in their eye of, and and almost that confidence of, I can build anything you asked me to build, but also enough, I wouldn't call it immaturity, but I guess greenness to them that their salary expectations weren't out landish, right, and so. So, yeah, I mean, that's that's really. What it came down to was was being gritty and cheap and cheerful and and finding people that came in and just love what they did.

Speaker 2: 2:13

And so you're painting this picture. You mentioned Calgary and I have actually just booked my flights yesterday or yesterday for a trip to Banff to do some backpacking in.

Speaker 1: 2:22

September for a trip to Banff to do some backpacking in.

Speaker 2: 2:24

September, nice, amazing. So you're painting this picture where you're talking about this cow town, of what's the experience when I get there.

Speaker 1: 2:30

In September? I mean it won't be. I mean we've moved along in general, but if you came in July, next month, I mean we've got our Calgary Stampede, which is all just it's rodeo and carnival and everything all just intertwined and it's 10 days of insanity every year Insanity. But yeah, I mean there's still a lot of farming. When you drive out from Calgary you'll see tons of farmland, heading out to the mountains and the indigenous lands and stuff along the way there and stuff. But yeah, you still see some people walking around with their cowboy hats, or maybe not, and the indigenous lands and stuff along the way there and stuff. But, um, yeah, you still see some people walking around with their cowboy hats, or maybe not in the hats but walking around in boots. But there's still modern, modern people too and young people that dress hip and and wear normal clothes.

Speaker 2: 3:17

So I know I'm excited to, uh, check out the beauty of Banff once again, and that's my escape and one way of usually trying to do it annually get together with some former MSP-ers, in a sense, and some that are still in the business today, and get together and go, yeah, down a 40-pound pack and go out and live the free life for a week.

Speaker 1: 3:39

Yeah, absolutely, it's awesome.

Speaker 2: 3:43

And the fact you took chances on. I guess you took chance on people. Right, you give people opportunity. You said those who were being cheap, but you also gave these individuals opportunities that they might not have had otherwise.

Speaker 1: 3:55

Yeah, I think everybody deserves an opportunity to do stuff right. I think lots of people took chances on me. I mean, when I moved to being the head of service delivery for the MSP I was at, so that was well. Again, it wasn't really an MSP but the IT company. They were almost a $5 million shop. You know 30, some employees, I think I was 26, 25 years old, so I was probably younger than, and significantly younger than, 90% of my team. Like that's a bold move for a business to take at that time. So they took a chance on me and when I started you know the partnership MSP and then even my own a lot of people gave me a chance and gave me a shot and gave me the benefit of the doubt. People gave me a chance and gave me a shot and gave me the benefit of the doubt, and even one of our clients that you know, when it was my MSP that I had taken on one of those two.

Speaker 1: 4:52

They came to a point where they acquired a massive, they did a reverse takeover of a massive organization and I was sure that was the end of the road for me and that that company had a full IT department and their CFO came in and said you tell us what you need and what help you need. Do we need to keep this IT department or can you guys take on everything? And they gave us the chance and we said we'll take on everything. They let go of that IT department, everybody else, they gave us the full shot and we were probably six, seven people at the time. So, yeah, I've always been a believer in that. Everybody deserves an opportunity, doesn't matter what their background is, where they came from, what challenges they have, what it looks like they can't do, if they have the right traits of you know, grit and determination. And you can just, you can just see it in people's eyes.

Speaker 1: 5:46

I like, I still feel that is, you can meet somebody and be like that person could do anything, whether they believe it or not, or whether they've done anything or not. You can just tell. And so those are the people that you know I'd rather be with. I don't want to be working with somebody when some time is tough and they're like all right, well, this isn't as cushy as I hoped, I'm going to see you later, right? Or hey, we're in a crisis period and they're like yeah, but my wife just cooked dinner and I'm going to go sit down and eat it, right, yeah, by all means, I want people to have that as their regular every day, but when it's crisis mode, I want the people that are like, whether I own this or not, I'm, I'm at war for this company, um, and, and those are the people that I'd rather have on my team no.

Speaker 2: 6:36

I can appreciate that and I've through that process. Um, you said you can kind of see it in their eye and they have that grit. Um, or the first talking about the, about the first two companies, did you make any bad hires? When you look back at them you're like, oh my goodness, what the hell was I thinking?

Speaker 1: 6:55

Oh, tons, tons of bad hires, right, I think in some cases it was getting away from looking for the grit and hiring and getting out over our skis on stuff. Right, hiring before a business was ready for a certain role, or even not even necessarily that the business was ready for that role. But just again, you know, hiring somebody from their accolades of previous accomplishments or you know things that had allegedly been accomplished or whatever, both in this business and in the last one you know, and and realizing that, oh, that's a person that just comes in to manage and isn't willing to get their hands dirty and isn't willing to actually run it Like they. They could manage a team just fine, but hopefully this thing is all just rolling Right and so, yeah, I mean it's, it's come down to that.

Speaker 1: 7:45

I think, at any point in any business I have now or in the future and it doesn't matter how big it is I will always, always go for grit now and and willingness to, to dive in and do anything. I, you know, I will always choose the person that will never say that's not my job versus the one that has built a billion dollar, whatever, you know, I don't care if you've built all that stuff, or or haven't. If, if you start telling me what your job is and what your job isn't, there's no path for you with me, um, and, and that's just for me the way that it needs to be.

Speaker 2: 8:22

Now with, obviously we know, post-pandemic, and we had a couple of years there where things were kind of dicey in regards to when it came to people. What kind of challenges did you face during that time? I mean, we know what our peers have faced and how did you overcome those when it comes to people and hiring for grit.

Speaker 1: 8:41

Yeah, I think so we had scaled up. I mean, this business was this current one? Was so we had scaled up. I mean this business was this current one? Was it's a COVID baby? Okay, and it was started during COVID in late 2020.

Speaker 1: 8:57

And you know, I think we did a lot of the right things and we were forced and wanted to be fully remote, fully distributed and stuff like that. We saw some really great early success. We, with that success, coupled with, you know, past exits and success, became very attractive during an investment bubble and venture capital bubble. So we raised, you know, a significant amount of money and we scaled up big and we hired a ton of people and you know, some of those were the absolute right people and some of them were the absolute wrong people.

Speaker 1: 9:36

Um, but when all the economic headwinds came in after the recession, when there was this, or after the pandemic story and there was this massive looming recession, everything changed economically globally in the investment world and venture capital world. As much of a darling as we were based on, how many free customers we were getting and the technology we were building and the opportunity and the pace that we were running at, it wasn't the same investable business running at it wasn't the same investable business. So we had to pivot hard as a company and protect the company so that we had the runway and survivability and sustainability. And so, you know, we had to let go a lot of the people, some of the ones that made a lot of sense to let go and probably never should have been hired anyways and a lot of that I, to this day, wish that they were still on this team and able to contribute the way that only they can contribute. But there's a number of other businesses now that have the the fortune of having those people um driving their companies and stuff too.

Speaker 1: 10:42

But, yeah, we I mean no secret we have the company um in november of 2022 and we halved the company again in a year ago, july last year um, just, you know, sheer, sheer necessity. I mean, it was the right thing to do, it's what we absolutely had to do, um, but uh, you know it's. It's one of those things now where you know we leaned out the business, we stabilized the business, we're, we're in a good position now and moving forward and and growth is is coming along very nicely. But, yeah, you, you definitely learn a lot around um growing a business or or making decisions in the business based on the merit of what the business is and what the current situation is, and not ever being I wouldn't say we were irresponsible, but less diligent with capital.

Speaker 1: 11:41

I think you decide to make hires earlier than planned because the right person maybe appeared, and stuff like that Opportunistically. I think there's still considerations for that, but in most cases, unless I can justify that role at this point in time, I will not make that hire again, type of thing. So yeah, I think, a lot more appreciation for recognizing where a business is and what a business needs at any point in time and focusing on that and just running, always running a good, viable business by a definition of what a good, strong business is, not by what a business could be so help me understand a little bit.

Speaker 2: 12:22

So you said you've had to pivot. Um what indication to you? Um that I guess the mechanism or trigger to say I've got to pivot. What was that?

Speaker 1: 12:35

Yeah, so we were a freemium product, right, we had no monetization. It was a thing of we were a free product to get customers on the platform, using the platform, and to be able to leverage what they were essentially feeding into the platform. And to be able to leverage what they were essentially feeding into the platform to create a product they could, we could, sell to those same people, right. So they were using and getting value from us for free, but they were essentially paying us with information about their business. Now it's all de-identified and all aggregated, so you couldn't tell who anybody is. But with a plan to be able to sell them a product in the future that gave them the benefit of that broader, broader knowledge set, right, um, in a fashion that could really impact their business. And so at that time, I mean we're, we're and we're very public about our plans to do that and what we could build as an intelligence system for, you know, an MSP based on that total aggregate data set. And a lot of companies were coming in and they were bought into that. And, hey, it's a free product too. So I'm going to take it when economic headwinds come in and you're burning capital at an incredible pace to build a product, to build technology, to continue to go out and acquire these customers for no revenue. That's not sustainable, right? And if nobody is stepping up to say, yeah, I want to keep funding that, then you need to make a change. So that's where we had to pivot is.

Speaker 1: 14:04

We had to pivot to a solution that we could monetize, that we could sell to customers, that we could convert, and we essentially had to get away from our freemium offering and go to everybody and say we need to start charging you now. This is not a bait and switch. If you don't pay us or nobody pays us, you got no solution to use here. We can't sustain it. And and yeah. So we went and and sure, we lost a lot, of a lot of companies that just didn't want to pay for the solution or whatever else. But we got a bunch that did, and you know we had to fight with the legacy information out on the internet that you can never delete.

Speaker 1: 14:44

Out there that says, hey, it's free. And some people come in like, hey, I want to use it. No, you got to pay. Well, it says it's free here. Well, that was before. And here's what we've had to change. Right, things change, so we had to change that. But we had to pivot and improve and change the solution from what people were willing to use for free versus what it needs to be for them to pay for it, and so that took a lot of work and a lot of effort to get it there. And, you know, fortunately we did and fortunately, with the amount of people that have stayed, we've now gotten to a place where we can offer that broader product to people, which is a big part of what we launched back in April and that was part of the, when you were talking about reading the book and then applying those marketing techniques in regards to rolling out in.

Speaker 2: 15:31

April was all part of that. So you sold Passportal and then you started the company that you are leading today. Yep, how much time gap was in there.

Speaker 1: 15:45

So we sold in April of 2019. I left the acquiring business in August of 2020. And this business we pulled together in november of 2020.

Speaker 2: 16:04

Okay, just trying to get an understanding going. Hey, you know what did colin do with himself? You know like he sold this business. Obviously he stayed on for a while, right, yeah?

Speaker 1: 16:11

colin, tried to retire a bit, but, um, you know, it goes back to a whole bunch of different things about you know, you're you maybe lose some friends over that period of time, you lose some relationships and stuff over time. Um, but I mean I was was relatively young. I mean we had built, you know, founded, built and exited two companies in the course of 10 years, um, before I was 40. And so when you try to retire at that stage, I mean it, none of your friends are retired, right, they're all working. Um, you know, I was in a relationship at the time where it was not a codependent relationship by any means.

Speaker 1: 16:57

So, um, my partner at the time was not going to retire, um, and yeah, it came down to well, do I hang out with my parents all the time because they're retired? Um, or what do I do? And so I tried to fill my time and do other things and and have fun and do stuff. But you know, at the end of the day it was like you're this lone wolf, soldier, doing your own stuff all the time and and then coming back to do other things. Or, you know, maybe at that too, people can't justify a certain level of expenditure for some type of activity or or getaway and stuff.

Speaker 1: 17:37

So, yeah, I mean it's it's. It's a condition where everybody thinks, oh, if you have a lot of money, do anything you want to do and you've got all this and life is awesome. It can be awesome, but, but money is not everything, right, and and at the same time, I felt myself being in a predicament where I wasn't contributing to anything. I had no passion, like well, I had passion for things, but there was nothing that I could put or direct my passion to that actually felt productive, right, and and so that's what it came to is is sitting and sifting through the subreddit and reading what people were asking, reading what people wanted, what they were trying to do, what they were challenged, and and, uh, yeah, deciding to, to start something up that could answer to that someday, uh, and and put towards it.

Speaker 2: 18:32

So so that's how you came up with the idea of starting the business you were running today was by going out there and looking for the problem that you could solve.

Speaker 1: 18:53

Yeah, yeah, absolutely. It was a, you know, a condition of you know the again, people are only willing to pay for something that solves a problem or a challenge that they have and one that's large enough that they're willing to pay for to do it. And when we came out, our ambitions were very, very clear in what we shared and we were very open and transparent about it. The byproduct of where we started with a billing reconciliation product, we were never expecting to rest our laurels on doing billing reconciliation. There's other companies that do it. It's not a business of consequences. I would call it to just do that one thing, and so that was a means to where we wanted to get to as a business and so, yeah, that to where we wanted to get to as a business. And so, yeah, that's that's where we landed and that's something we were able to sell to get people to. You know, help us sustain the business and and afford to continue building to what we're building. But yeah, I mean we're, we're very excited right now with with the things that we're building and what we're putting out to market.

Speaker 1: 20:01

And you know, I'd say it's stuff that has been long sought and long desired and you know, it's one of those things that people are like oh wow, like how long did it take you to build that thing? Or how long have you been working on that? Well, you know, on the product itself and fashioning the things probably a year, oh, you build all. No, it's been three and a half years and we've spent probably $12 million to build it right. Like it's not a situation of oh yeah, hey, we just wrote some code and tossed this out and, wow, boom, all this stuff's happening. Right, it's everything in behind that's gone into it. We knew it was an ambitious and audacious journey when we set out on it and we knew it was a journey that may end in great defeat or failure. But you know, right now we continue to persevere and we'll keep doing whatever it is we need to do to protect this opportunity and preserve, yeah, our chance to ultimately have the impact that we look to have.

Speaker 2: 21:03

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