Why A Successful Exit Was A Complete Letdown With Corey Wert

Listen to this episode
iTunesGoogle PlayStitcherClammr ItShare Leave a ReviewListen in a New WindowDownloadSoundCloudSubscribe on AndroidSubscribe via RSSDownload Free eBookAnother Call to ActionOne More Call to Action

Join the newsletter

Subscribe to get our latest content by email.

Corey Wert is the founder of Digital Blue Moon, a boutique digital agency in Toronto that is disrupting the outdated multi-vendor model. He has also started, grown and exited Free Flow Marketing back in 2014, a successful digital agency focused on providing services to only Fortune 500 companies.

Corey sits on multiple boards and is incredibly well respected within the entrepreneurship community.

In today’s episode we dive deep on why exiting his first company was the biggest let down of his life and how he was able to get out of a deep depression after selling that first business.

Corey explains his most important steps to set a solid foundation when building a company.

We’ll also discuss why he decided to outsource his first six employees from the Philippines when getting started.

Plus Corey shares how he completely got blindsided on his latest venture with an untrustworthy partner.


Key Points From This Episode:

  • Corey tells us how he got into the world of entrepreneurship.
  • Hear Corey’s story as he transitions from corporate to entrepreneur.
  • Learn about Corey’s biggest struggles when he started Free Flow Marketing.
  • Find out how Corey got Free Flow Marketing up and running.
  • The most important steps to help you set a solid foundation when building a company.
  • Understand the growth trajectory of Free Flow Marketing.
  • Discover why Corey started outsourcing overseas.
  • Hear Corey’s experience exiting the company and what he went through.
  • Why Corey strongly believes that failing forward is a must in life and business.
  • Find out how Corey worked through his depression and what turned it all around for him.
  • Why it is so critical to structure your day and make time for yourself.
  • Understand how Corey got involved with his new company, Digital Blue Moon.
  • Discover Corey’s biggest takeaway and learning lesson from his experience.
  • The importance of having a good support network.
  • Learn how Corey forces himself to get out of his comfort zone.
  • Find out why failure, to Corey, means learning.
  • Discover who has had a profound impact on Corey’s life.
  • Hear what’s next on the horizon for Corey.
  • And much more!















Links Mentioned in Today’s Episode:

Corey Wert — http://bluemoon.digital/

Corey’s LinkedIn — https://www.linkedin.com/in/coreywert/?ppe=1

Email Corey — corey@bluemoon.digital

Free Flow Marketing — http://freeflowmarketing.ca/

Timothy Ferriss’s book, Four Hour Work Week — https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357/

123 Employee — http://www.123employee.com/

UpWork — https://www.upwork.com/

Elance — https://www.elance.com/php/landing/main/login.php

Re Perez — https://brandingforthepeople.com/

Philip McKernan — http://philipmckernan.com/

Mastermind Talks — http://www.mastermindtalks.com/

Mark Zuckerberg — http://iammarkzuckerberg.com/

Richard Branson — https://www.virgin.com/richard-branson


Transcript Below

Read Full Transcript


“CW: I’ve traveled the world, I’ve seen things I never thought I’d be able to see, I’ve been able to carve out good time for myself instead of just trading my time for two to three weeks’ vacation a year, I’ve met some fantastic people and I’m grateful and all of that is sponsored by an entrepreneurial lifestyle.”


[0:00:25.1] ANNOUNCER: Welcome to The Fail on Podcast where we explore the hardships and obstacles today’s industry leaders face on their journey to the top of their fields, through careful insight and thoughtful conversation. By embracing failure, we’ll show you how to build momentum without being consumed by the result.

Now please welcome your host, Rob Nunnery.


[0:00:45.8] RN: Hey there and welcome to the show that believes you are destined for more and that failing your way to an inspired life is the only way to get there. Today, we are sitting down with Corey Wert, Corey is the founder of Digital Blue Moon, that’s a boutique digital agency in Toronto that is disrupting the outdated multi-vendor model.

Corey is a good friend, he’s a brilliant guy, super humble and has successfully started built, grown, exited another digital agency back in 2014. At that time, they were focusing on providing services to only fortune 500 companies. Corey’s incredibly well respected in this community and entrepreneurship community.

He sits on several boards and we go deep on why exiting that first company in 2014 was actually the biggest let down of his life. We’ll be discussing why he decided to outsource his first six employees from the Philippines when he first got started, how he was able to get out of a deep depression after selling that first business and how he completely got blindsided on his latest venture with an untrustworthy partner.

But first, if you’d like to stay up to date on all fail on podcast interviews and key takeaways from each guest, simply go to failon.com and sign up for our newsletter at the bottom of the page. That’s failon.com.


[0:02:03.1] RN: Corey, welcome to the fail on podcast my man.

[0:02:05.7] CW: Hey, thanks for having me Rob.

[0:02:07.6] RN: Sweet, just for a little context, we are in the beautiful city of Toronto right now, actually a mutual friend of ours, I guess he called it a game room, I don’t know if I’d call it a game room, there’s a little couch.

[0:02:20.1] CW: There is a foosball table.

[0:02:21.8] RN: There’s a foosball table and some creepy looking camera equipment that I wouldn’t know if this is SEO company or –

[0:02:29.8] CW: You know what? He did call it a game room, not a games room so it’s very appropriate there’s only one game in here.

[0:02:35.2] RN: That’s a good point. I just want to dig into it man. You’ve had some highs and lows as an entrepreneur.

[0:02:42.4] CW: Absolutely.

[0:02:43.7] RN: Like all of us but just so we have some context, how did you first get into the world of entrepreneurship?

[0:02:49.6] CW: I’ve always kind of had like a hustle to me, you know, very young, I would do things like sell gumballs and everything like that to the kids in my class but my first step into entrepreneurship was really around 2008, I was working for a big consumer package goods company here in Canada, they did about six billion in sales.

I worked in the marketing department there and I just really saw that there was like a massive shifting trend that that was coming. IT really felt like a sweet spot for me in the sense where I knew I loved marketing but I’ve always had a fascination for technology in the digital space.

At that time, you know, people were considering digital to be experimental at best.

[0:03:36.8] RN: Yeah, it was still early.

[0:03:37.9] CW: It was still early for the bigger companies right? The innovators were grabbing on and making the most out of it and good for them. For me, there is just this disruption that was coming, I thought that I was in a good spot with a good knowledge on both sides of the fences and really was never…

I was very fortunate to have the job that I had, I did well but I was never really content working for someone else, you know, to steal a quote from you actually, you know, you’re either working on your dreams or you’re working on somebody else’s.

I realized that it was time to take the leap and get out there and take what I knew and try to bring that to the world.

[0:04:12.0] RN: Cool man, I want to actually dig in to kind of like the details there because you’re working at this company, I mean, did you get laid off or fired or were you just kind of proactive and like, “I want to make something happen.”

[0:04:22.3] CW: Yeah, funny story actually. I was doing well, I was on the fast track, I was moving up to management ranks, you know, good salary, everything was going really well but I always had a certain discontent on the speed with which things happen in a big company.

You’re always waiting for someone to bestow the honor and tap you on the shoulder before you can kind of get to the next level and while you have to learn to play that game patiently, it’s also something that was a constant and eternal struggle for me.

At that point, you know, I had done a digital campaign and it was extremely successful and kind of blew the lights out compared to all of the more traditional stuff that we were doing.

[0:05:04.4] RN: What were the metrics based on? Was it based on performance? How did you gauge that you blew it out of the water?

[0:05:10.7] CW: One, the level of insight that we were able to get from that campaign, you know, traditional media and traditional marketing like you sit there, you activate your campaign and then three months later you see the sales data start to roll in and then you try to retrospectively connect the dots and figure out what happened. We were able to see immediate traction, we were able to make immediate pivots.

It ended up garnering kind of like more social engagement, we ended up doing really well through a contesting promotion and again, we were able to actually identify a subset of our target base which we always assumed was X.

We saw that there was this whole other opportunity out there. For me it just like, the instant data was something that just immediately kind of like sparked with me.

[0:05:55.6] RN: Just so I understand better, is this like a Facebook ad campaign? What exactly was it?

[0:05:59.3] CW: I remember sitting down and doing a presentation on YouTube to my president and he was like, “that’s interesting but I don’t think that’s ever going to catch on.” This is before Google had even bought YouTube right? I remember sitting there and saying like, “this is going to be the future of kind of like video advertising” and the cost for which you could do it compared to a traditional media buy for TV was insane and so it was literally just kind of like foraying into that.

Facebook was still like university Facebook back then.

[0:06:29.3] RN: yeah, that’s true. 08, 09.

[0:06:30.4] CW: Yeah, it was really kind of before that but they were all sorts of platforms where you were really starting to see a two way conversation right? Like commenting was starting to become a thing and again, that instant connection with the consumer was something that you just never really had through traditional marketing.

It was always one-way messaging. You know, kind of you vomiting your message on everyone, the exact same way where digital really allowed you to connect and forge a relationship and build some loyalty with your customers.

[0:06:58.0] RN: And measure the results.

[0:06:58.3] CW: And measure the results and be able to take that and leverage it for insightful, meaningful campaigning down the road right? There was always discontinuous improvement that you could do in the moment with digital data.

[0:07:12.0] RN: You created this campaign at this company.

[0:07:13.7] CW: Created a campaign, it did really well and for me, it just kind of like a light bulb had turned on. You know, I really loved the marriage of marketing and technology and I remember sitting down and doing a presentation and showing the results and this was supposed to be like my moment right?

They were instantly going to make me president of the company and I just remember it being you know, that was a great experiment and we weren’t going to do that anymore For me, I couldn’t really understand what was happening so I literally sulked back to my office. I sat down and you know, I just looked out and it was a very risk adverse culture you know?

There was retirement that was on the horizon for a few key players and they didn’t want to introduce any risk.

[0:07:59.1] RN: They don’t want to rock the boat.

[0:07:59.9] CW: No, they just wanted to hit their numbers, they wanted to get their bonuses and then they wanted their package at the end of the day. I sat there and I realized, I’m like, I’m going to sit here, wait for them to die, not literally and then when a new team – when new management comes in, I’m going to have to sit there and forge the same relationship that I had spent years doing.

I looked out and I was like, “I’m like five years out from sitting in the seat that I thought I was sitting today.” Typical kind of entrepreneurial fashion you would say, I wrote my resignation letter and handed it in right there and I was just like, “I’ll figure it out,” It was very much the jump and build the wings on the way down. In hind sight, I may not have done it the same way but I’m glad that I did because it was just like – it was that just kind of like fearless step that threw me into a world that honestly, I was unprepared for.

If I tried to baby step my way in, I could have seen that there would have been a thousand excuses, I would have fed myself on why not to commit to that.

[0:08:58.3] RN: How are you doing financially at this time? Did you have financial resources kind of hold you over?

[0:09:02.2] CW: Yeah, I was making a good salary, I was doing really well in terms of corporate terms, especially for my age. I had a little bit banked up. I didn’t – I thought that that was going to be more than enough to kind of like cushion me.

I made a brave move but it wasn’t a stupid move I felt at the time. In hind sight, you know, the buffer that I thought I had did not last really – and things did not take off as quickly as I assumed they would so you know, could I and should I have banked up a little bit more? Absolutely but again, I feel like it’s just part of the learning curve right?

Getting into a dire position for me was something that really kind of like turned on the jets.

[0:09:48.5] RN: Yeah, I’m right there with you man, I’ve had a lot of conversations with other entrepreneurs and I almost feel like I had this conversation with everybody I talk to on here but it’s on one hand, you have people with the burn the ships mentality and then on the other hand, you have the people with the more practical approach which is build a bridge mentality. Yeah, do a side hustle right?

Do it from seven PM to two AM but I’m right there with you man. I’m a burn the ships guy. I do good with pressure.

[0:10:16.4] CW: That’s just it. For me, in that moment, in that pressure, a stronger version of me comes out and I know that. Some people are very kind of like security oriented and the right move may be to do that side hustle for a little bit right?

There’s two different approaches. I was okay with the risk but I could see how that, I could use that as an advantage but I could see how it could also be a crippling effect for some people. It’s really just about figuring out like, what you feel you’re up for and then live by that.

Then when you get that side hustle, when you start to see a little bit success – throw it behind. Because the thing is, it’s never going to get the traction, it’s never going to get the growth that you would want unless you’re committing full time to it. If it’s just about proving that it can be done, that’s cool, do a side hustle in the weekends and the evenings, whatever. But when you see something, go.

[0:11:10.2] RN: Yeah, totally agree 100%. As you were going with Free Flow Marketing right?

[0:11:15.5] CW: Yeah, correct.

[0:11:16.3] RN: Okay, that’s the agency, that’s the business you started, what were your biggest struggles early on, you said it didn’t take off like you thought it would right out of the gate.

[0:11:24.5] CW: Yeah, for me, the thing is like, you know, there’s this saying like you know what you know, you know what you don’t know. But you don’t know what you don’t know and I didn’t know that I didn’t know a lot. You know, you come out of it and you’re like, I’m going to do digital marketing, I’m going to do it for companies, it’s really going to help, it’s going to move the needle.

That part of it came naturally and it was easy. But then, everything else that it takes to run a business. Eventually when you have employees, being the HR. I didn’t develop a leadership team until really late in the game. I had a bunch of like in the trenches doers. Then I was marketing, I was finance, I was sales, I was president. For me, it was again like – I feel like of school of hard knocks has always been my best teacher, I’ve done the formal education and I’ve got a very expensive piece of paper that sits on the wall.

I do nothing in my life that relates to what I learned in school at all. For me, it was really like just not really going in kind of like eyes wide open and again, maybe that’s a good thing because it allowed me two step forward fearlessly, also foolishly but again, I was able to use that.

For me, failing forward is an absolute must. I’m convinced I did everything wrong in that business before I got something right.

[0:12:51.6] RN: Did you start up? How much money did you have to put into that business before you started seeing dollars back?

[0:12:56.8] CW: I had saved up probably about 50 or 60 and yeah, that was used – like again, just to kind of get the business up and running.

[0:13:07.5] RN: Branding site? All of the –

[0:13:10.0] CW: Yeah, doing the site, doing the design, getting some marketing materials, doing the presentations, I wasn’t pulling a salary for myself yet but I still had obligations right? Still needed to eat, still had a mortgage, still had all that stuff and so a good portion of it was for living, a good portion of it was deployed into growing the business.

All of that was gone before I made my first dollar. It took a lot longer, I think I suffered from what everyone does at the beginning which is always trying to find kind of like that magic bullet solution that’s going to help me land my clients or you know, give me instantaneous search engine optimization and having a high ranking so people could find me and really, again, this was not knowing what I didn’t know. There was so many different components that were going on that again, I suffered from shiny object syndrome and it wasn’t until I really chose one service and focused and built a solid presentation on that.

Had really strong messaging and really understood how to help people.

[0:14:08.9] RN: What is that service?

[0:14:09.9] CW: SEO.

[0:14:10.6] RN: Got it.

[0:14:11.1] CW: Once I kind of had that, things just started to take off, started to land clients, the singular service allowed me to focus and that started to bring in the revenue which allowed me to kind of grow and scale the way that I did where I honestly think, you know, coming out of a big business, the unfortunate part is like, numbers get lost on you like when you’re looking at marketing budgets that are eight, nine figures.

You kind of lose the sense of money a little bit. That’s such a big number and so you know, coming out of that really made it difficult in the sense where I just didn’t know where to focus, I didn’t know how to scale properly, I tried to have a big business before I had a small business.

[0:14:50.9] RN: I think it’s a really interesting point that I think you made a mistake, a lot of entrepreneurs make where they try to create a service that’s for everyone rather than going really narrow at first?

[0:15:01.4] CW: Don’t go niche, yeah.

[0:15:03.0] RN: I mean, if you go really narrow at first, it’s way easier because you know one, you’re going to have a better offering right? It’s going to be much stronger, it’s not going to be trying to provide a service for everybody.

[0:15:15.4] CW: and you can also deliver what you’re selling which to be honest, in my space, there are a lot of agencies out there and they’re really good at selling but they don’t follow through on fulfillment. It’s the biggest problem in our industry, it’s why the agency can have a really negative connotation and the number of clients or colleagues that I’ve sat down and said, “Yeah, we tried to do the big agency once and it just really didn’t work,” like that is so common.

It’s a constant pain point in our industry that’s something that you’re always battling against, especially when you’re in a sales pitch with a company who doesn’t necessarily know you that well right? Because almost everyone has, almost every client that I have had has been burnt before they found me and so just being able to choose that, fulfill on it, build your reputation around that and get some income for growth.

Those very simple things set a solid foundation to allow you to build a really great company. But if you don’t do that first, then you know, you’re building with like toothpicks and sticks and not on a solid foundation.

[0:16:15.9] RN: Yeah. Just thinking back when you were at the corporate job moving into your agency. Were you able to take any clients with you from your corporate job that you could take on as clients at the –

[0:16:27.5] CW: No, because I was on the client’s side right? If I was on the agency side and I was representing a bunch of clients, it probably would have been a lot easier because if they liked me, I could have said “hey, I‘m going to go over here,” it’s not in direct competition to the agency that I’m leaving because I’m doing a service that they don’t provide.

Originally, that was my pitch. When I went out on my own, my first step was to contact the agencies that I had worked with.

[0:16:49.4] RN: Yeah, of course.

[0:16:50.8] CW: Say “hey, I want to setup a digital division within your company” but everyone’s like you know, “it’s a fad, it’s going to go away” right? Anyways, I was kind of forced to go out on my own because nobody was really willing to bite.

No, being on the client side, I couldn’t take myself and I was the client right? it was literally starting from scratch like standing still or actually sitting still on the bedroom floor.

[0:17:17.6] RN: When did things really start to take off in that first business?

[0:17:20.4] CW: I’d probably say around the two and a half, three hear mark. Like I said, I’d given myself about six months and I’m like yeah, by that time I would have replaced my income. I was so far off on that forecast but right around kind of like – I had built like a steady business where I was doing okay and I had started to pull a little bit of a salary out of the business.

Things really kind of turned around two and a half to three years. We participated in a project, we were brought on as a digital provider to an agency of records so an agency of record is basically like the person who owns the client relationship.

What you see a lot of the times is they’ll fragment out to specialist agencies, you’ll have someone do the branding, you’ll have someone do the digital component, you’ll have someone do the media buying and all different agencies will do that.

It’s a really convoluted model. We were the digital component and that program got put up for an award and that was the gust of wind in the sales and it was very steady and very rapid growth from that point on.

[0:18:21.4] RN: Was it just referrals from other businesses at that point?

[0:18:25.3] CW: Yeah, you just start to get the name right? To be honest, a lot of my success was also – I don’t care what anyone says, like timing and luck is a huge component of business. There weren’t a lot of competitors offering what I did.

When businesses did start to pay attention, there’s only a handful of providers that were out there offering these services and most of them weren’t good.

[0:18:47.4] RN: You’re doing more than SEO at this point right?

[0:18:48.4] CW: At this point we’re doing more than SEO, we’re starting to get into like t that point we were doing a little bit of kind of like online branding and identity packages for online, we were doing video marketing, we were into social at that point. We had had kind of like a broader service offering for the digital space.

[0:19:08.6] RN: How big was your team at this point? Just roughly.

[0:19:11.5] CW: When that started to turn, we were probably around 10.

[0:19:15.1] RN: Okay.

[0:19:16.4] CW: When we were all said and done and the exit happened, we were around 67.

[0:19:20.9] RN: Got it. I want to get to that but still, I kind of want to give the audience and give us an idea of kind of the growth trajectory and I know it took obviously a while to get that first dollar back but when did you hire your first employee?

[0:19:35.9] CW: The first check that I got.

[0:19:37.2] RN: Okay. You said –

[0:19:40.4] CW: Yeah, I did you know, I did what I think a lot of people start by doing which is I outsourced overseas. You know, right around that time, you know, that was becoming a very popular thing within the entrepreneurial community.

[0:19:54.7] RN: Four Hour Work Week came out.

[0:19:56.3] CW: It was right around the time of the Four Hour Work Week and again, it was a blessing and a curse at the same time because it allowed me to get help when I really couldn’t quite afford it yet but at the same time, it was also a much larger kind of management exercise than I was anticipating. Where you think you’re just going to make your hire.

You’re going to send kind of like your SOP Checklist, just get that done and you're like “now I have two more hours back in my day, I’m going to read Tim Ferriss’s book.” It definitely didn’t work out that way. Again, slowly built through the Philippines to be honest. First, six or seven employees were all out of the Philippines.

[0:20:35.0] RN: What series did you use?

[0:20:37.0] CW: I tried a bunch, like 123 Employee and really, I ended up using Odesk which is now UpWork. That was really kind of like my key platform, also dabbled with Elance, one of the more popular platforms as well. I just found that the talent over there was a little bit more expensive and out of the range of what I could afford at the time.

[0:20:55.4] RN: Totally. Then, within Free Flow, you move forward in the time line a little bit. Two and a half, three years, it really started to take off, what happened once it started really booming? What are the next, because you had the business what? Six years total?

[0:21:11.9] CW: Eight.

[0:21:13.6] RN: okay, got it. Take us through from year three through year seven and a half, eight.

[0:21:20.2] CW: Again, it was just, for a successful company, it’s amazing to look back and see how much failure there was in it. For me, you know, kind of like that first spurt of growth, it was something that I think we handled well. To be honest, it was something that was completely from the sense that the type of employees that we had hired required very clear instructions and so we’re very heavily documented in terms of like SOP’s and what to do.

Our systems and our process were really solid and that kind of like fueled and allowed us to kind of put more weight into the organization because we had the structure to be able to support that.

[0:22:06.0] RN: How did you know that that needed to be built?

[0:22:08.4] CW: I didn’t, it was one of those things that in learning how to work best with my team and my employees, it was something that just kind of naturally evolved after trying 10, 15 different approaches.

It just turned out to be kind of like a benefit in the sense that that allowed us to take the thinking out of a lot of the grunt work that needed to happen and when you’re removing the thinking from the process, you’re actually creating several hours of work in the day that would have been lost.

That allowed us to kind of like sustain and be able to survive under the weight of the new growth. As we started to diversify the services even more, as we started to hire quicker than really, we were hiring as quickly as we could just to keep up with the level of work that we were having.

That started to expose that we are now getting to areas or levels of talent that required a different system or different structure. It’s not a one size fits all

[0:23:07.6] RN: Who are your clients at this point? Are you servicing small business owners?

[0:23:11.2] CW: No, early on, we were getting a lot of work through other agencies for big fortune 500’s. We were playing a small role in that but that’s where a lot of the work came from, down the road I think probably year four, I started to see that there was a lot of risk in that. When you’ve got 50, 60% of your revenue coming from one client, that client goes away, you don’t have a business right? You got a client.

And again, just kind of like seeing what was happening online and we were on the earlier side of kind of like local SEO and local marketing. I know it ended up becoming a couple of really huge internet marketing launches which completely destroyed the industry, thank you.

We started to kind of diversify our client base, got a bunch of smaller clients, that provided the stability and the consistent income and then the big ones were gravy, that’s what allowed us to do really cool shit.

[0:24:11.7] RN: Got it.

[0:24:12.3] CW: Can I swear?

[0:24:12.7] RN: 100%.

[0:24:13.8] CW: Perfect. I’ve been holding back. I’m a swearer.

[0:24:18.1] RN: Really cool shit.

[0:24:21.2] CW: Well, that’s just like, that’s when you're sitting there and you’ve got like really big budgets and you’ve got a lot of money to either test new things, build software, do really good reward systems for your employees, send them on retreats, it just allowed us to build a really solid culture.

Again, when the money’s flowing, it’s just a really beautiful thing. I think diversifying how we got our revenue really big kind of like one off project based work which was great but it was not steady.

Feast and famine model right? Which is very common for the agencies? But that kind of like that stable base right? Having you know, I think we had a couple of hundred by the end of it but having that stable base like, that just made sure that the waters were calm and everything else was just gravy and play money.

[0:25:08.6] RN: Got it. Towards the end of this business, take us through kind of what happened towards the end, obviously you know, we’ve talked offline about it, you had a successful exit. How did all of that come about and then kind of take us beyond that and what you did after this business?

[0:25:28.4] CW: Well I think the natural evolution, whenever there’s a disruption in any industry is that all of a sudden, the people who are sitting at the top and are feeling the pain and the most from the disruption start looking down and figuring out who they can acquire right? They buy their way out of the problem.

[0:25:44.0] RN: Did you have this in mind from the beginning by the way?

[0:25:45.9] CW: To be honest, you know, I think you walk in like every other entrepreneur that you’ve seen whether they build this massive company and then they sell it for billions of dollars and you know, I definitely had an exit plan, it’s probably better than my business plan at the start but it happened faster than I assumed it would.

[0:26:05.1] RN: How early on did you start thinking about this? Was it from out of the gate when you’re –

[0:26:09.6] CW: From the gate, I always try to figure out before I take my first step, I always try to figure out what’s the goal post that I’m walking towards? I know that you know, how you got to the goal post and the play on the field will change and you have to, you have to be able to pivot and be nimble with external factors but I always kind of knew what it was.

I wasn’t sitting there and trying to build a business that I was going to run into my 80’s. You know, I still have an aspiration to retire by the time I’m 45 and just be able to spend my life the way that I want to and that may be you know, coaching other entrepreneurs, it may be me sitting on a beach and becoming a fisherman. I don’t know.

I just know that you know, I’m in it with a purpose and I love what I do and it’s got my attention now but I don’t think I’m going to sit there and say “man, I wish I didn’t retire at 45,” on my death bed.

[0:26:59.0] RN: Sure. After you sold this company, you know, take me through that. I know we’ve talked offline about this and it wasn’t all this cracked up to be.

[0:27:09.3] CW: No it wasn’t, you know, what ended up happening like I said was the industry started to change and we got gobbled up by much larger firm, they needed to basically change the sign and be in business and so at that point, you know, I had done a really good job at creating a very good job for myself.

I was tied to the company, I didn’t move behind the brand fast enough, I was consistently hearing from my clients, “we hired you, we want you to be there” and that really kind of created like a seven day a week, 14, 16 hour a day job.

I was completely burnt out. You know, I think there’s also this illusion that when you work for yourself, you’re going to have more time, you’re going to be able to work when you want to work and if you have the drive of an entrepreneur, just know that that is a complete lie that you’re telling yourself.

[0:28:00.1] RN: 100%.

[0:28:01.4] CW: I am the worst boss I have ever had. I am so harsh, there is no forgiveness. I was completely burnt out and at that point, you know, I really felt like kind of money was my motivator and there are a variety of reasons for that but what I found out after exiting the company was that money wasn’t the motivator at all.

It was what I was striving for but the blues weren’t bluer, greens weren’t greener. I didn’t wake up happier.

[0:28:28.7] RN: You had to set this, had all this money and it just wasn’t fulfilling?

[0:28:33.5] CW: Yeah, it just didn’t fill my cup. And in all reality, I ended up slipping into a very deep depression for the next year.

[0:28:39.2] RN: Just because it wasn’t what you were hoping to have at the end of the.

[0:28:43.1] CW: You know, it’s something like, one, I think it was the function of you know, I was definitely a very burnt out, I did a horrible job at kind of creating like the boundaries and the recharge moments that I now hold sacred and what I do with my day to day.

For me, there was a little bit of kind of like that burn out fatigue but I also realized or I failed to realize at the time and I realized after doing some deep work on myself that my values wasn’t really around the money, it was around helping other people.

I thought my whole value systems was A when it turned out to be B. Again, so much of my identity had been tied up in the company, I took a lot of pride that like, I helped people, I felt very fortunate that I was in a position where I could make a good living while providing and helping people earn a better living for them in their families.

When that was gone, it was amazing how quickly my identity disappeared and how quickly my confidence disappeared and then you start telling yourself the story that I could never do that again, “why did you exit, you’re a one hit wonder.”

The story just went really negative, really fast. It took a lot of time to kind of like really get to the root of that why it was happening, why my programming was like that, why my story base was like that and I just slowly had to kind of like undo that over time and fight my way through it.

[0:30:07.1] RN: got it. Take me to what that time was like, I know it’s probably not easy to talk about and you said you were in deep depression and you know, you and off line, I hope you don’t mind me saying this, you know, you even said that you still don’t do a lot of podcasts to this day because you’ve had like an imposter syndrome.

[0:30:23.4] CW: 100%

[0:30:25.0] RN: Why? Let’s try to dig into that if you don’t’ mind.

[0:30:28.7] CW: Yeah, digging into it, I was a very accomplished shit head as a child.

[0:30:35.2] RN: Sure.

[0:30:36.1] CW: My parents always told me to play to my strengths and I bet you they regret that when I was a rebellious 13 year old and so without getting too deep into it, you know, I was asked to leave, I lived on the streets for a little bit, I was in a group home for a couple of years.

[0:30:50.6] RN: In your teens?

[0:30:51.8] CW: In my early teens. For me, a lot of kind of like my self-worth, when you have the people who are supposed to love you unconditionally say we can’t deal with you anymore. In fairness to them, it was the right thing. My actions, what I was getting expelled from schools, I was getting in trouble with the law like what I was doing destroying the family and what they did was to protect the family and so I get that.

It took me a long time to be able to see that but I see it now and to be honest, I’m grateful for what they did. But that strips at a very young age, that strips away your confidence, that strips away your self-worth, the people who were supposed to love you unconditionally don’t and kind of just makes all of that go away.

I’ve always like, as much work as I’ve done on that, I carry that still to this day. I’m always amazed when I’d be sitting there in a meeting with a client and I’m doing what just, I think everyone always knows and they’re sitting there like, “Oh my god, this is a great idea, we have to do it.”

Those moments, even though there’s been a lot of them, they still catch me by surprise. You know, I don’t think that there’s anything overly special about me, I’m not – I don’t have an insanely high IQ, I was a horrible student.

[0:32:02.9] RN: Is it part of what drives you though?

[0:32:04.1] CW: It is, there’s that like, I’ve got to hustle and I’ve got a work ethic and because I’ve seen so much over time, you know, failures are always hard but I think I’ve gotten a lot better at dealing with them, being okay with them, in fact, one of our core values at the company is failed forward. Don’t be afraid to fail, be afraid not to take the lesson from the failure.

That’s something that I try to instill because that is a value that I hire against now because we’re inevitable going to make mistakes, this is a really difficult industry. It’s hard to understand all the nuances of so many different client business. Things change so quickly.

[0:32:41.4] RN: It’s like going back to your corporate job where you kind of went outside the box and created a digital campaign and people are okay with the status quo, they weren’t okay with failing forward.

[0:32:49.7] CW: As you say, most people aren’t, like 95% of the population will take the safe play, they’ll take that security and some people view the corporate world as that, it’s a safe paycheck, I view that as the riskiest thing because you’re not even in control right?

[0:33:04.1] RN: Right there with you, yeah.

[0:33:06.4] CW: There is no security in that world. If they have a hard year, trust me, the axe is coming down. You hope not but you could be right?

[0:33:14.9] RN: Employee wise, that’s the biggest expense typically.

[0:33:17.3] CW: Yeah, for me, the appeal of entrepreneurship was always just about kind of being the master of your own destiny, if I’m going to fail, I’m going to fail on my terms, I’m going to fail because of something I did, not just because I was sitting in the wrong seat at the wrong time right? I forgot what your question was.

[0:33:32.2] RN: Actually I did too. I liked where we’re going with it though. Okay, just to kind of keep the timeline going. You’re in a rough place, depression hit, how did you get out of that and then I guess, what was kind of the timeframe of that lull when you left that business before you started your current business and did you do it – were there any businesses in between?

[0:33:59.1] CW: No, there wasn’t, that year of depression was deep, there were day long stretches where I couldn’t even get out of bed. I would wake up and like it was almost like clockwork, every single morning I’d work up around 4 to 4:30. My mind would be racing to the point where I couldn’t’ turn it off, I couldn’t even process what the thought pattern was in my head, it was just random and it was a million things all at once and my day for that year literally consisted of me waking up uncontrollably crying for a couple of hours.

Then sitting there and oddly enough, the only thing that I couldn’t read because my mind was too busy, it was always just – the only thing that kind of gave me reprieve was Candy Crush. I don’t even want to tell you what Level I’m on I literally crushed for like nine months straight for four hours a day. It’s embarrassing.

It was one of those things that it was that distraction. Yeah. I did a lot man, I did therapy, I really reconnected, by that point I had a really great relationship with my family again, they’re my biggest support but I spent a lot of time with my mom, my dad, my brother and really, it was just getting back into –

It took a lot of time to even get there but getting back to doing things that were healthy for me right? Going back to the gym, meditating when the mind would allow me to meditate, getting back to reading and kind of getting into self-growth. All of the things that had gone by the wayside because I was so bad at managing healthy time for myself and just literally sacrificed everything.

I could go to the gym for the hour or I could sit here and just take care of this last minute client request. I always chose the client request. It was getting a lot of what was important to me which is you know, my family, my close relationships, reconnecting with my friends, all things that had suffered during this time because all of my focus was on the company and getting some healthy habits back in my life.

Giving myself space to actually become okay with if I never recreated this success again, that doesn’t mean that I didn’t have it in the first place and that doesn’t mean I don’t have value for this world.

It was really just identifying what my real value system was, not what my ego was telling me it was.

[0:36:29.6] RN: How did you do it though? Did you –

[0:36:32.1] CW: Therapy, reading, yeah, Again, leaning on a lot of friends, there are a couple of networks that were just completely, they saved my life. One of the things that I would suggest is if you ever find yourself where you’re going through this or you’re going in that state, trust me when I tell you you’re not alone.

The first six months, I didn’t tell anybody about this, I felt so ashamed that I was feeling this way because I had no reason on paper, if you read my resume, there was no reason for me to be feeling this way.

[0:36:58.3] RN: But you lost your identity and you are in that transitional period where you didn’t know who you were or what to associate yourself with right?

[0:37:04.9] CW: No but I hid what I was going through from everyone that I knew. I withdrew and that isolation only made it worst. So I remember and actually sharing it for the first time with a friend who is a part of a mutual entrepreneurial network that we were in and he told me about how he had gone through the exact same thing like five or six years ago and I can’t even tell you the switch that turned in me because all of a sudden I wasn’t alone.

This wasn’t a Corey problem and then the more people that I would share my story with they’re like, “Yeah, I had this fail and this happened” or “I had this and yeah, I also had an exit and didn’t know how to deal with myself after” and I realized that we live in a high stakes game and the highs are really high but the lows unfortunately are really low. One of the biggest things in the factors to me turning around was realizing that this was not an isolated event.

A bunch of people have done it and pulled out of it and for some reason that alone gave me hope that if I just stuck through that I too will pull out of that one day and that just gave me kind of the courage to start building the building blocks to get myself out of the hole.

[0:38:12.8] RN: I know you started to say, sorry I interjected, but you said if somebody else is going through this whether it’s dealing with depression after an exit which are first world problems but still –

[0:38:23.1] CW: Yeah for first world problems, I’m telling you it’s a problem yeah.

[0:38:26.8] RN: But for other people maybe also going through a hard time whether it’s just they don’t know what they want to do.

[0:38:31.7] CW: A hundred percent.

[0:38:32.2] RN: They’re lacking identity, they don’t know what business to start, what would you tell them?

[0:38:35.1] CW: No for me that was a big thing and that last year in the corporate job I was really unhappy. I was starting to realize that I wasn’t in the right place. It wasn’t a fit. There was friction that was happening within me and that’s really hard and also a lot of the times you don’t even know where it’s coming from. So I just had this unhappiness but I didn’t even know at that point that it was a professional unhappiness.

It was just an unhappiness and so again I think that blind spot can be really dangerous for people. So if you feel like you are in that like to be honest one of the best things that I do now is journal and not with thought, not with judgment. It literally is like I am feeling this right now I wonder why. I ask myself that question and then I’ll write stuff out and so I would encourage anyone who is sitting there and being like “something doesn’t quite feel right” you don’t know what to do about it yet.

To start to dig deep on different facets like bucket your life in certain areas professional, personal, relationship and really try to identify which bucket because there is always a core issue and again, it may not be – obviously this podcast is geared toward people who want to go out on their own, entrepreneurs, but maybe it’s just even in your own job it’s a facet of it. It’s not the need to completely reinvent yourself right?

But getting really clear on who you are and what’s important to you is something that I feel I left way too late in the game and I could have been a better entrepreneur for myself and for my team if I just got really clear on that but again, I’m head down run into a wall, head first and then figure shit out after.

[0:40:18.6] RN: Yeah, it’s a great point and I was talking to Re Perez, he actually said the same thing in terms of people are so busy so you go through your day –

[0:40:26.4] CW: You interviewed Re?

[0:40:28.1] RN: Yeah, so I was talking to Re.

[0:40:28.9] CW: So I can’t be on this podcast anymore.

[0:40:31.5] RN: Is that all?

[0:40:32.1] CW: Hey dude, I’m out.

[0:40:34.7] RN: No but he was echoing the same thing you are saying right now is people don’t spend enough time trying to figure out who they are right? Because life is so busy they don’t ever take a step back, turn everything off, meditation is a big thing right? So just spending time with yourself without any distraction which is hard for a lot of people nowadays.

[0:40:52.3] CW: But to be honest because of the always on mentality of an entrepreneur, you have to force yourself to take that time off but it’s hard like I’ll be sitting there and you know yoga is another thing that I do right? Or I go to the gym and I find that those are great outlets but I can’t tell you how many times halfway through my workout I’m like, “Gosh I’ve got to get back to the office” when I know that is the healthiest and the best use of that hour.

[0:41:17.7] RN: I totally resonate with you. I am having a big issue recently. I’m a big reader. I used to read a lot more than I do now and when I start reading now or I try to start reading, I’m so freaking ADD. I’m so interactive like, “Oh I just have my phone vibrate, what do we got?” so it’s hard but what do you recommend in terms of really being able to set time aside to spend with yourself?

[0:41:41.1] CW: Oddly enough it’s a really easy thing to do but it’s a hard thing to honor. You just got to structure your day. Like I have a block in my calendar from 11:30 to 1:00 every single day of the week and that’s my gym time and the days that I don’t go to the gym that’s my walk time not when it’s cold or shit here in Canada which happens quite a bit but for me that time is sacred and my COO knows that. My entire team knows that, they won’t even infringe upon that space unless it’s a crucial meeting that needs to happen but that’s literally happened three times in the two years that I’ve been running the new company.

[0:42:20.3] RN: What are you doing during that time like say if you’re going to a walk, are you listening to anything or are you making –

[0:42:24.0] CW: Sometimes I am listening to music and sometimes not and I am just walking.

[0:42:30.5] RN: I’m trying to figure out if you are consuming content whether via audio book.

[0:42:34.6] CW: Sometimes I am, sometimes it’s just quiet time and again I allow myself the flexibility of what that looks like depending on it like if I am having a super stressful day and it’s been all day of meetings and we’re putting out client fires and working with all of that then it tends to be either music or quiet time because that just calms me down like sitting there and going and consuming content when the mind has been working and is churning all morning.

It doesn’t make a lot of sense so again, giving yourself that flexibility and that permission that while you need to set that structure with yourself, what happens within it be flexible, be kind to yourself. You’re having a crazy day, go do something really relaxing. If you are having a relaxing day, go and get the blood going and just allowing yourself that permission to be kind to yourself no matter what that looks like is huge and the lesson that I have only learned and like the last year or two.

[0:43:30.8] RN: It sounds like you might have learned that from the same person I learned it from, Philip McKernan, maybe, maybe not but –

[0:43:36.6] CW: Hold up, did you interview Philip on this too?

[0:43:38.8] RN: I did.

[0:43:40.2] CW: Oh my god, I definitely should ask for who the hell is going to be on this podcast before I got involved.

[0:43:46.0] RN: No but we were actually in the Bahamas for the Mastermind Talks and I was talking to Philip and I think it was the first morning there and I was like, “Man I haven’t…” because I was on a series of kicks of fitness, nutrition, I was up every morning at 5 AM. I go to the Bahamas and whenever I travel my routine goes thrown off crazily and I was telling Philip that well I just gave myself permission to take it easy this morning. So he taught me to be way less hard on myself because I beat the crap out of myself a lot.

[0:44:19.7] CW: I am my own harshest critic like I said, I’m the worst boss I have ever had. To be honest, the work that Philip does is so necessary for people like you and I. I wish I found Phil way earlier than I did. I found him as I was getting out of my depression. There are a lot. He is so good at those one liner sound bites that stick in that horrible Irish accent that you can’t even bring out of your head but to be honest, he’s got four or five sayings that I find myself like I will repeat to myself maybe once a week.

So I wish I found him earlier but the be kind to yourself was learned the hard way. It just took a lot of time and it took a lot of forgiveness and that started during that year of the depression where I just really had to learn to be okay with myself because it was something that I don’t think I ever was before that happened. There is a lot of issues from the past.

[0:45:20.7] RN: Yep, so it sounds like you did a lot of work. You got your head in the right place, you got yourself surrounded by loving people and got back to who you are. So once that happened, take us through how you started the new company. What made the idea come together then also the time line, what was that break between the end of Free Flow and the story of your new company?

[0:45:42.2] CW: Yeah, so the end of Free Flow officially was March 31st, 2014 and then I went on a trip to Japan in April and when I came home that’s when the depression sort of hit. I did nothing that year except crush a lot as I said and when I started feeling a little bit better, I took on four or five coaching clients. They were all people that were in an industry related to mine who were at a smaller scale so I knew where they were and how they got to the next level.

And I started doing some side coaching and consulting for them and there was one business in particular where I just became fast friends with the guy and there is a lot of potential in his business but it was standard where somebody gets into a position because they know how to code a website or they know how to do something but they don’t know how to run a business and his business was in dire trouble. I didn’t know how bad it was when we first got involved.

But I consulted with him for I think nine months along with a couple of other clients and started to feel a little bit better and decided that I wanted to get back in the game but I didn’t want to do it full time yet. So him and I have structured a deal where essentially I was going to take part equity within his business. I was going to sit there two days a week as his managing director. I was going to clean everything up and then everything client facing, production stuff like that was going to be his.

But the business had been, was going to be my side of things, I ending up getting involved in the business. I was looking through a certain set of books throughout the entire consulting period and then once we got involved and I got full access to the books, he hadn’t paid taxes in a bunch of years. He was behind paying his employees. When I walked in the door, the two key employees were ready to hand in their resignation and had both said, “We are just waiting until you got here to see if it was going to be different” and so it really started as a turn around.

And again, you think starting off with the business already like I’ve broken one but one already there. You think it is going to be easier and again, you don’t know what you don’t know right? And just because you’ve been successful before it doesn’t mean you know what you are getting yourself into again.

[0:47:52.0] RN: Yeah, did you put any cash on this business at all?

[0:47:54.2] CW: No I didn’t. I had taken a very small salary and then equity as the compensation.

[0:47:59.6] RN: So less risk right?

[0:48:00.2] CW: Yeah, so less risk but at the end of the day and this is where you’ve got to choose your partners carefully because he had signed a statement with me saying that there is no pre-existing debt within the business before I got involved because the second your name gets put on it, the liability of the company now becomes my liability and he sign it. It was a fraudulent contract and what we ended up having to do was we really realized how big the problem was when there wasn’t enough money in the business for me to turn it around.

And so him and I sat down and we talked and at that point, he was focusing on one or two services and he knew that I had always dealt or evolved into a company that was doing a larger service scope and I told him that we needed more money in the business and then went out and leveraged one of my contacts, brought them on board. He knew it was going to be a change more into an agency than a specific service house and we talked about that.

Went for a bunch of walks in the park and he was like, “All right let’s do it” and the second that we got that $50,000 deposit and it hit the bank account, it was garnished completely by the government and that’s when I started to see the truth of “okay, this guy has not been paying taxes.”

[0:49:14.8] RN: So when you were going on a walk on the park with this guy, you hadn’t known any of this yet?

[0:49:18.7] CW: I didn’t know it yet, the financials that I was working with were troublesome but were fixable and then we realized though we didn’t understand all of the debt, again, who doesn’t pay taxes for five years? Choose your partners carefully.

[0:49:36.9] RN: But any red flags like looking back on this guy?

[0:49:39.4] CW: Looking back on it, there were a thousand red flags.

[0:49:41.7] RN: Okay so why did you ignore this?

[0:49:43.5] CW: The reason why I ignored it and the reason why I particularly gravitated towards him was he was on the brink of a depression and he was starting to get anxiety attacks.

[0:49:52.4] RN: So you could relate.

[0:49:53.1] CW: And I built the story in my head that perhaps I went through what I did so that I can help him avoid it and to be honest, even over it, I hung with him way too long. He is no longer with the business. He exited on his own, tried to steal the business from me as a thank you but my COO from day one was like, “We need to fire him” and I was like, “It’s never going to happen, learn to work with him” and I stuck by him and so many red flags.

Like from the day where he’d sign the agreement saying there was no pre-existing debt, he put himself before me. He was actually opening me up to a huge amount of risk and he was okay doing it. When I look back at it I remember when I said, “Hey, here’s this read and sign it” he got up and he went for a walk because he knows, he was processing and he made the conscious decision at that moment to lie. “I need out, he could help me get out and I don’t care if this puts him in a world of trouble.”

And so we had that deposit garnished. That kind of started to show how bad things were. The books that we have had from a revenue or an accounts receivable standpoint, he had created duplicate invoices and a lot of the work that was in there, the AR was so aged. It was bad debt at that point. There was no way that it was recoverable so the revenues were inflated, the losses were hidden, there we so many things along the way as I was trying to fix the business and sometimes we had to take some hard stances with his clients.

And say, “Hey, he’s been under charging you, he didn’t know the market value, we’re upping our prices” and obviously clients aren’t happy in that state but we had to do what was right for the business and then I would find out that he was sitting there and when the client would complain with him because he had a relationship, he’d be throwing me under the bus.

[0:51:37.5] RN: Bad mouth you, “it’s him changing the prices.”

[0:51:39.6] CW: Exactly, I wish this wasn’t happening to you in all of that and him and I actually had a couple of talks where I remember I took him outside one day, not to fight him but I looked at him and was just like, “I know you’re doing this, this, this and this and you’re undermining what we are trying to do and I am trying to fix your business and trying to get this back on track” so looking back there were so many signs but I was blinded by my want and my need to help someone who was on the brink of going through of what I went through which was the worst experience of my entire life.

[0:52:10.2] RN: So outside of choosing your partners carefully, what’s going to be the biggest takeaway and learning lesson for you in that experience as painful as it is?

[0:52:19.7] CW: So like I said, no longer with the business. He ended up, we had to talk grade him on moving around a lot because he was not even a great employee and he ended up leaving and trying to steal a bunch of clients and employees when I was away traveling. So for me my advice in terms of choosing a partner is do your due diligence. It’s a business relationship. Don’t let the personal or the emotional side and a lot of people going to business with their friends is the wrong fucking reason.

And so do your due diligence, make sure that when you partner with someone that there is an equal contribution and a value. That there is something that you provide that they don’t and there’s something they provide that you don’t. That wasn’t true, like I said not only was he not a partner, he was actually one of the more dysfunctional employees that we had and so that would be it. Do your due diligence, know who you’re getting into bed with and make sure that there is an equal value contribution that’s made.

Because I think on both side there was a resentment when we took the company, turned it around it was doing about 300,000 a year maybe 350 and losing money and within 11 months, we had turned it into a seven figured business that was profitable. You would think that that would make someone happy but I think he almost resented that I could do something that he wouldn’t and you’d see that with the constant undermining right?

And so just be careful, partnership is like marriage. Don’t partner up with the first person that is willing to let you feel some stuff up over the shirt, right?

[0:54:00.7] RN: Yeah, that’s a good point. So where’s the business at now?

[0:54:04.0] CW: So the business is doing well. I feel like we are really positioned to help disrupt what I think is a broken agency model. My previous agency, we were always one spoke in a larger wheel. What we’ve done here is a really diversified the service bases so that we can handle everything from initial market research all the way through campaign retrospectives and what this allows us to do is it removes the multivendor agency model.

So you are not getting markup upon markup upon markup which creates this inflated budget for the clients. You can have a variety of great companies but that doesn’t mean that they are always work together well and so it eliminates that. It allows us to move faster and since we own a digital campaign, we don’t do anything traditional but because we own a digital campaign from start to finish, we are willing to be tied to results because if something is happening along the way, we can’t blame the advertising team.

Or we can’t blame the branding team, we are all of that right? So I think like the sales cycle literally has gone from six months to six days like when we sit down and we explain our position, it’s a pain point that every client feels and so right place, right time. There’s been growing pains. It has not been anywhere – like I figured based on previous success this was going to be super simple. Again it’s amazing how many times my thinking is just complete.

But it allows me to bullshit my way into scenarios but we faced some growth which caused problems, we didn’t have the right team members to start. It’s a very different business managing as broad as a service goat because you are getting very different people like your devs are a culture completely separate from your creatives and trying to get them to play together like I can understand why they were broken apart before.

I feel like I have created this mad house trying to bring them all in but when we get it right, the results are something that I am extremely proud of. We’re well into seven figures, we’ve been profitable since inception which is a really beautiful feeling. I think we’re poised for great things. This year we are focusing on culture and systems and process. Doing that same thing, it was a different problem starting this because I had a reputation and so the business came fast and it came easy.

But then what I found was we didn’t have the foundation, we didn’t have the systems, we didn’t have the process and that’s okay when you’re starting up but now that we are at the level that we are, we need that foundation for the business to be able to take more and more and more weight. We can’t sit there and just fire fight or be agile all day long. That component always exists within an agency to make a client happy but we really need to get that culture in place, get the system in process.

So when we’d look at another year of growth the business can maintain it because we did grow to a point where again it was like one in one out just because we didn’t have the right business model set up.

[0:57:03.1] RN: Got it. So that brings us up to speed right? Up to date so out of all of the struggles along your journey, all the trials and tribulations, the success, if you had to pin point I guess one moment in time or one thing that happened to you that makes you say, “Man I wouldn’t be here if that didn’t happen” what is that moment?

[0:57:24.9] CW: Oh that’s a big question. I’ve got to be honest, when things were not working out at the beginning, I had the support of two people, my girlfriend at the time and my dad and them looking at me and just basically saying, “You’ve been through a lot worst, you can do this” it was the gasp of air that I needed just so that I could get back to the surface and that was right at the tipping point where I was like the conversation was like “I am packing up, I failed at this,” I have given myself two years to make this work, if I wasn’t then I was going to try to parlay that experience well on a resume and go get a job again.

[0:58:07.4] RN: This is two months into your first or two years into?

[0:58:10.0] CW: Two years into the first business and that moment was really the – if this was easy everyone would be fucking doing it and again, it was that reminder that I’ve been through worse. It was that reminder that always when you want to give up, it’s literally just on the other side.

[0:58:25.0] RN: I was about to say that.

[0:58:26.1] CW: And I know that sounds cliché but that has been true a hundred, every time I’ve thrown my hands in the air and said “fuck it. I’m done” within a week I’m like, “How could I ever say that?” it’s just the way that it works.

[0:58:39.4] RN: Yeah, you even said that three years in is when business really took off. If you would have quit at year two, who knows where you’d be right now.

[0:58:45.9] CW: Right and I’d probably be in a job miserable. So very thankful that support network and making sure that you have people that are going to back you up not just in the good times because what I really found is the amount of people that are around when things are going well you can’t even keep track of it but when I was down, there were a few people and so for me, it’s not about having the biggest network or the biggest crew possible.

It’s about having a couple of people that you know have you in good times and bad and if you have that, you have a rich life and you’re positioned for success on a very difficult road at times.

[0:59:26.6] RN: So Fail On is the mantra that we live by here and I love that one of your core values is fail forward because it’s perfect and I’m so glad you are able to come on and share some of this stories but the idea is if you are not failing, you’re not growing right?

[0:59:40.5] CW: A 100%.

[0:59:41.0] RN: So how do you force yourself even on a day to day basis just in your life to get out of your comfort zone?

[0:59:46.3] CW: I think I’m actually horribly uncomfortable on my comfort zone at this point. It’s something that you definitely need to learn to push yourself. I remember all of the excuses when I was first starting to keep me in my comfort zone. I’m like “I won’t do that today I will do that tomorrow” and it was just a delay to make sure that I wasn’t outside of my comfort zone but now I get really uncomfortable sitting there and be like, “Hmm everything is running really smooth”.

“I need to fuck it up” right? And whether that’s trying out a new model or bringing on a new service scope or I am sitting here and getting out of my comfort zone and supporting my body on my podcast, this is again the imposter syndrome. It is still very strong, self-promotion is not something I do well. I like my work to speak for itself and I like my clients to speak for me and could I have done better? Probably if I was a little more self-promotion-y 100% but this was an experience that I feel that people needed to hear about.

I always assumed that when you look at a successful entrepreneur that it was so easy and you work a couple of hours a day and it just came naturally.

[1:00:50.6] RN: It’s all you hear about, right?

[1:00:51.3] CW: No it’s all you hear about and what you don’t understand is that overnight success story was 10 years in the making. You just hear about it when it’s big. You don’t hear about the blood, sweat and the tears and the constant times that they almost gave up and as my network with entrepreneurs and colleagues have grown, you realize there is not a single person that got it easy, except for maybe Mark Zuckerberg.

Yeah, again really out of my comfort zone but I feel like it was a message that people needed to hear. I love the premise of this because I think it gives a realness and a true picture of what an entrepreneurial life is like and like I said, I wouldn’t change it for anything. I’ve traveled the world, I’ve seen things I’ve never thought I’d be able to see. I’ve been able to carve out a good time for myself instead of just trading my time for two to three weeks’ vacation a years.

I’ve met some fantastic people and I’m grateful on all of that sponsor by an entrepreneurial lifestyle. So I love this. I love what you are doing here and it’s a message people need to hear because it’s not easy but it’s worth it.

[1:01:59.5] RN: What does failure mean to you?

[1:02:00.5] CW: Failure means at this point learning. Failure used to mean crawl into your bed and figure out what the hell is wrong with you. Fair enough. No, but for me again it’s one of those things like we screw something up and my first question is “okay, what do we learn from it and what are we doing next” and that’s it and if that vernacular is what that follows “hey we made a mistake,” then the meeting doesn’t happen until the vernacular changes because it’s okay. It’s okay to fail, nobody gets it right all the time.

[1:02:30.4] RN: So if there is somebody right now out there that they know they want to start a business, they don’t know what to start or maybe they are looking for the perfect business idea which we know doesn’t exist right? But if they came to you and said “how the hell do I get started, what do I need to do? Just tell me” what’s one action item or directive that you could give them at least as step one?

[1:02:53.3] CW: So the first thing that I would do is figure out and again this is something I did so poorly, figure out the type of lifestyle that you want first. You can have a lifestyle business that gives you all of the freedom that you want that allows you to be location independent but there’s most likely going to be certain sacrifices that comes with that. You want a lifestyle business, it’s going to be hard to build a hundred million dollar empire.

[1:03:18.1] RN: Exactly but to make a couple hundred grand a year very doable.

[1:03:21.7] CW: But if you are sitting there and you are traveling the world half the year and you are working from where you want to and you’re pulling out a 150 to $200,000 a year and I am not talking revenue, make sure that that’s your take home pay, then hell, that’s a life that most people would sign up for. There’s nothing wrong with that and for me, it was just like I need to build an empire and what I realized now it’s the lifestyle that’s the most important thing.

Like I want to go see my niece and my nephew, I want to be able to hang out with my parents at least once a week. I want to see my friends at lunch. All things that I could not do in my last job and I have made sacrifices right? I’ve clearly laid out in the vivid vision of our company. We are not aspiring to be a thousand clients nine figure agency. It’s just not what I want but this is something that I just learned in the last year or two and I’m still getting coaching from some of my friends.

Like how did you shape it so for me it’s get clear because the idea of only going to a business for something that you love so it doesn’t feel like work is such horse shit. If that happens, awesome, blessed position but if you are going to wait for that, then enjoy your job. So for me figuring out the type of lifestyle that you want and then figuring out what type of businesses would fit that and then from there, figuring out what skillsets you have that would lend well to one of those business models.

And then figuring out from there what your first step would be, that’s the four step sequence but you’ve got to do that in that order and then actually start at the end game not how do I take my first step. Reverse engineer that and then that way you make sure that your first step is the one ai8ming you towards the right goal post.

[1:05:04.8] RN: Love it, I hope you guys paid attention because that is the step by step directive in getting started and getting out of a situation that maybe you are not so happy in.

[1:05:13.8] CW: Absolutely.

[1:05:15.1] RN: Who’s had the single most profound impact on your life? If you could name one person or two if you need.

[1:05:20.4] CW: I’m going to name two because I don’t do well with rules then I’m going to name three. No honestly, I don’t idolize or get star struck by celebrities or big business icons or anything like that but that impresses me on a level that is beyond belief is Richard Branson and I know that seems like it’s an easy answer but the reality is, is he is involved in 400 different businesses, he’s done I think it’s eight billion dollar companies which no person on the planet has done.

Like you got a telecom or a real estate tycoon and everyone has their one spot, he’s duplicated it eight times and his lifestyle is amazing. Like dude sits there with his two personal assistants for an hour and a half in the morning, that’s his business stand and he goes out and he plays. So I feel like he got the model right in a way that nobody else has been able to do it and that might not be the end game but that type of lifestyle is something that I honor and I value which is why I look up to him.

[1:06:30.9] RN: And not necessarily the $8 billion companies but just necessarily to design your life in a way he has.

[1:06:36.2] CW: It’s just the way that he has. He has a ton of fun with what he’s doing, he spends his time the way that he wants to spend whether that’s work or whether that’s play and as long as you are always on the line with what you want to be doing, you are going to be a happy person at the end of the day. So again, just based on that it’s not the dollar amount. It’s not the fact that he is one of the billionaires in the world. It’s rally how he was able to create his life with his business.

I feel like that’s something that entrepreneurs fail at. You either have a good life in your business to shit or you have a wicked business in your life to shit. So that would be that and then to be honest I think the person in my personal life that kind of impacted me the most was my best friend that I met at Meager Palm. He ended up passing away in 2000, November 6th, 2000 which was really hard to go through but he was – you had the family that you’re born into.

And I really feel like the universe screwed him up because him and I were supposed to be brothers and we just missed but he was instrumental at giving me the comfort zone to turn myself around. So that’s when I was still rebellious. I was getting in trouble, I had AWOL-ed from the group home, I had spent time in jail and he was the anchor that really settled me down and put me what was then a 20 year journey but the first step toward me being where I am today happened when I met Alex.

And so eternally grateful and in all honestly his death and his passing away was a reminder of how short and how lucky this thing is and so for me that’s part of the hustle right? You just don’t know so get it done.

[1:08:22.1] RN: Yeah, that’s beautiful. Thanks for sharing. I know it’s not easy to reflect on when he means a lot.

[1:08:26.6] CW: Yeah, I just want people to know that this shit is not easy. Life is not easy, it’s full of troubles, it’s full of trials, it’s full of failures but if you’ve got the right people everything is manageable. Everything is doable and you just got to keep the faith in yourself and if you can do that, trust me you’ll get past everything.

[1:08:43.0] RN: Yeah so looking forward for you, what’s next on the horizon? Obviously you are building your company but what are you most excited about right now?

[1:08:51.5] CW: I’m really excited, it’s one of those things that I’ve always had a very different approach to what I was doing in this business. I’m excited because we’re disrupting an industry that’s right for disruption but I’m also building the business the way that I want to and arguably I failed in the first couple of years when you’re starting something up and you’re turning something around, I’m just wired to be in the trenches and getting shit done.

We’ve got the term GSD in our company right? It’s a GSD day like just get shit done. But it’s all with an end goal of me actually kind of stepping back form the day to day, my COO is fantastic, putting her more on the front lines, me moving more into an advisory and so I can work on other pillars of what I envision kind of like the blue moon universe to look like over time.

It’s not just about the agency, we’ve got a couple of plans, we’ve got like adventure arm, there’s a bunch of things that we’re doing and this is allowing me as I was saying before to play where I want to play.

It’s giving me the freedom to play when I want to play and so I’m just really excited that all of these lessons have not been lost. I’m actually, you know, doing what I coach my team to do which is fail forward and I’m just getting

[1:10:03.5] RN: Yes.

[1:10:04.0] CW: Yes.

[1:10:04.9] RN: I love it. I couldn’t agree more man and I love that like I said, one of your core values is fail forward because it embodies what we believe here with fail on. I’m going to respect your time though, we’re running about an hour and 15 so I’ll let you run man but thank you so much for sitting down and chatting, I know you don’t do it often.

[1:10:22.4] CW: I don’t, my pleasure though. I love what you're doing here.

[1:10:25.3] RN: thanks man.

[1:10:25.7] CW: till next time.

[1:10:26.8] RN: Cheers.


[1:10:27.8] RN: All right, so you could find Corey through email at corey@bluemoon.digital. That’s Corey@bluemoon.digital and of course, all the links and resources Corey and I discussed including more information on his company, can be found at the page created especially for this episode, that would be at failon.com/019 and keep an eye out for the next episode, Will be sitting down with the brilliant marketing mind in Toronto, Dev Basu. Dev is the founder of Power by Search.

Canada’s fastest growing digital agency, he’s absolutely crushing it and we sit down in his beautiful office based in Toronto to go deep into his journey and if you're interested at starting a business from scratch, bootstrapped, this is definitely an episode you don’t want to miss.

As I continue to belt this project to fail on with a simple goal of getting people to once and for all decide that they’re going to fail their way to creating inspired life, if you could do one thing to support the cause I’d be super grateful. When you click on the subscribe button and leave a rating and quick review, this allows the podcast to simply be visible to more people. To rate and review the podcast, it’s super easy, just go to failon.com/itunes or failon.com/stitcher.


[1:11:36.1] ANNOUNCER: That’s all for this episode of The Fail On Podcast. For more resources, show notes and action items to help you find success in your failures, sign up for our mailing list at failon.com.

For more actionable inspiration, we’ll catch you next time right here on The Fail On Podcast.


Leave a Comment