Behind The Scenes Of 10 Years Of Entrepreneurship

In this episode, I recap what it’s been like to run my own business for the last 10 years. I talk about how I got started, and share some of the challenges I’ve faced along the way, as well as the successes I’ve had. If you’ve ever wanted an insider view on starting a business, you’ll definitely be interested in this episode!

Listen in the player or read the episode in blog format below!

Today’s post is going to be a little bit different than usual. I'm not going to be sharing any tips for your ads or ad creative specifically. Instead, I want to give a bit of a behind the scenes of the last 10 years of running my business.

It’s November 2022, and my first paying client in my company was 10 years ago, in November 2012. This was my first paying client that wasn't a friend or a friend of a friend, and that feels like a pretty significant milestone for me.

I feel pretty proud, especially looking back at everything I've built and accomplished in the last 10 years. So, I have been thinking for the past couple months about how I wanted to celebrate this, and creating this blog post is one of those ways.

I also love seeing the behind the scenes of other people's businesses, so I thought it would be cool to give my audience a behind the scenes into my business and what it took to grow it, and how I got to where I am today.

I'm going to be getting into how I got into this field, how I got my first clients, how I grew my business, the process of hiring a team and then deciding I didn't want one, and some of the biggest lessons that I've learned along the way as well.

An Early Interest In Tech

Both my parents are programmers, which meant that I was exposed to computers from a pretty young age compared to a lot of people my age. We had computers in my house from the age of 7, and I learned to code basic front-end web development (HTML and CSS) around the age of 13 or 14.

Around that age I built my first website, one that I coded from scratch, that was a Buffy the Vampire Slayer fan site (that was my obsession in my teenage years).

Working on my website was my favorite hobby and I spend lots of time adding new content to it, and every few months I would redesign the whole site, which meant recoding everything. Through all this practice I got pretty good at web development and design.

Getting Into Entrepreneurship In University (2011)

Fast forward to when I went to university, and I never even considered studying computer science. I have definitely kicked myself for that decision a few times, but I really feel a big part of that decision was just lack of representation. I didn't even think of it as an option, because when I thought of a computer programmer, I thought of nerdy men and not someone like the person that I felt I wanted to be.

So I studied psychology and when I was in university I became friends with another woman who I'm still very good friends with today who was studying business and she invited me to join the entrepreneurship club at school.

That got me totally hooked and I started taking business classes with my electives in my psych degree and got a certificate in Public Relations.

That friend and I also started our first business together, which was a partnership where we promoted local music and planned local music events for our city. We ran a blog and a website and interviewed a lot of local bands to our blog.

A lot of the local bands started asking me how we built our website and when the found out I had built it they started asking me to build them websites and I realized that there could be something there. So, I started building websites for local bands that I knew.

In November 2012 I launched my own business and I got my first paying client, which was a local pet store. Around this time, I also started working in marketing roles. My first real office job was for a non-profit where I was doing marketing and communications. After that, I got a job for a marketing agency in an account coordinator position. While I was working these jobs I was building websites on the side for local businesses.

Taking The Side Hustle Full Time (2013)

After about two years of working and running this as a side hustle, it started getting really busy and I wanted to be on my own so bad that I decided to make the leap. I didn’t have any savings. I didn’t do this in a very smart way at all.

I just figured that my business would just keep growing and I would just keep getting clients, but that's not exactly how it happened. So for the next two years, I think I probably made about $20-30,000 a year, so it was not quite the success that I thought it was going to be.

At this time, I had also started adding in help with social media, email marketing services, SEO, Google Analytics services, and I'd even made my first online course, which was a Google Analytics course. But it was a struggle for sure, I definitely didn’t know what I was doing.

Taking A Job For Some Stability (2016)

Not long after I started my company, I ended up moving to a new city. In part because of some personal changes in my life and I also just wanted something new and different.

So, I moved to Kelowna, BC and my first week there I rented an Airbnb while I was looking for my own place. And I ended up meeting the son of the woman I was renting the AirBnB from and I was chatting with him about what I do, and he worked for a local tech company.

He invited me to go and interview the next day, and I literally started the day after that. So, within a week of moving to this new city I had a job.

I was a bit disappointed, but also excited. I really wanted to run my own business, but I knew that what I was doing wasn't working. I felt like this would at least give me some more experience and some money, which I needed. So that’s why I ended up taking the job.

During the year I was at the company we grew very quickly. We were Canada's fastest growing start-up that year. We were also Canada's largest Facebook advertiser. We were focused primarily on Facebook advertising and running affiliate campaigns for other brands.

Because of my experience with building websites and Google Analytics, they put me into a CRO role doing website testing and optimization. But after about six months, I moved into a data analyst role, which was really cool.

I didn't have any experience with data analytics, but it was such a good learning experience for me. The people that I got to train under were incredibly intelligent, and most people at the company were very smart and driven.

It was such a good experience for me to work for that company. I feel like it taught me so much and gave me such a good perspective on the industry and business.

Getting Let Go: An Opportunity For Round 2 (2017)

After about a year in that job, the company had some layoffs and I ended up losing my job. It was sad and scary, but I was also very excited about the opportunity and the push to get back into doing my own thing and trying to make my business work this time.

After I lost my job I was putting a lot of feelers out. I was doing job interviews and applications, but I was also going to networking events and mentioning to people that I was open for freelance opportunities.

I actually had been going to networking events very actively for the whole year that I was at that job because I was new in town and I loved the tech community there and I really wanted to get involved.

I think that really, really helped me in getting my business off the ground because I had a network built up already, so then to mention that I was looking for work, most people already knew who I was and my experience and what I could do.

My First Few Clients (2017)

I ended up landing two clients pretty quickly who hired me on a monthly retainer. This was so crucial for me in getting up and going because they were each paying me $2,000 a month.

My previous salary was $50,000, so this was already pretty much the same, or even a bit more than what I was making monthly at the job. On a monthly basis I was doing a lot for these clients, I was definitely undercharging I would say. But it was so helpful to me to have that consistent monthly income coming because it gave me the stability to grow my business from there.

I think it's so important to not try to grow when you're desperate, because clients can feel that desperation when you're on the sales call and people are going to be more likely to low-ball you.

You're going to be more likely to take lower cost projects and get stuck in this cycle of having projects that aren't paying you enough but being so busy with these smaller projects that you can't go out and find bigger price projects, and this is not a good place to try to build a business from.

One of the questions I get asked the most is how did you get those first clients after you lost your job, and so I'll share how I got those two clients.

One of them was an ads agency that I had a previous connection with through networking. I reached out to the agency owner and I said, hey, is there any way you need some help with subcontracting any of your work? And she said, yeah, for sure.

The second one was again, someone else that I'd had a connection with, this time through a mutual friend. He had expressed interest in possibly hiring me previously, so I reached out and I actually analyzed his website and his funnel and I made a strategy for how he could improve it and I sent that to him and he was like, yeah, this looks great, let's do it. So that was how I got those first two retainer clients.

Ingredients For Success

Another thing that I feel really helped me be successful quickly was that I niched into one thing. I was a Facebook ad specialist and I only did Facebook ads. I didn't even offer Google or anything else at the time.

This was way different than when I was basically trying to do everything, I was offering email marketing, social media marketing, websites. I was trying to be a Jack-of-all-trades and as a result I was wasting a lot of my time researching.

I also couldn't actually charge as much because I wasn't a specialist. So, I think that specializing in Facebook ads really helped me to succeed much quicker with my business the second time.

It's funny because I actually initially planned to specialize in CRO since I had more relevant experience to that field, but everyone that I talked to ended up asking me to help them with Facebook ads because of my experience at the company I'd worked for previously, which was a Facebook ads company. But I had never actually even run any ad campaigns at the company, my roles was to look at the data.

I would hear everyone, all the media buyers, talking about what was working and what they were doing and how they were testing. But I don't even think I actually ever ran a single campaign at that company before going off and having people hire me to run their ad campaigns.

This is why these first two retainer clients that I have are great, especially the ad agency I was subcontracting for, because they ended up teaching me a lot about how to Facebook ads up.

Within just a few months of getting laid off, I was making five figures a month, and I thought that was incredible coming from a 50K salary. I was incredibly happy with that.  

A lot of people would ask me, how did you get this up and running so quickly? And of course, for me, it didn't feel quick because I felt like I'd been trying to start my own business for five years.

I really believe that those past five years of running my business as a side hustle really set me up to succeed much quicker, because I already knew how to manage client contracts, how to set up my company, so all of that foundational stuff was out of the way already.

Another factor that helped me succeed was the city and the environment that I was in. It was a very small, tight knit tech and entrepreneurial community and I was very involved and that really helped me to get referrals and use word of mouth to grow my business.

Another factor is that Facebook ads at this time were just beginning to grow in popularity and people were really starting to see the success that they could have with Facebook ads and Facebook ads were incredibly cheap at this time. I wish I could go back and have the add costs that we had in 2017 because it was incredible. So I think there were a lot of environmental factors that really played into things taking off for me in that way.

Someone asked me on LinkedIn recently, if I hadn't have gotten laid off would I have still tried again to launch my business and left to go off on my own. And my answer is without a doubt, yes.

Running my own business has always been what I wanted. Even as a teenager, I never really knew what I wanted to do when I grew up, but the idea of running my own business really appealed to me even at that time.

I just don't think that I'm someone that's cut out to work for other people, and I think that type of person makes the best entrepreneurs because we have to make it work.

I don't know how long it would've taken me to make the leap though. It definitely wouldn't have happened on the same timeline. I probably would have given it another year or two before I went off and started my own business.

I'm so grateful for that experience of getting laid off because I got severance pay with it, I got EI, and I also got into a government program called Community Futures, where if you're laid off, you can get training on how to start a business. It was a really incredible program, and I actually still have my advisor. I feel like that program set me up really well to create a business plan and just understand how to set everything up properly and set myself up for success.

So that was the first five years of my business, and the last five years there have been a lot of ups and downs.

The first year I would say was just kind of scrambling to keep up with taking on clients and that kind of growth. I started out charging $1200 a month at first, but I had a good amount of demand so I increased to $2100, and then $2,500, and then $3,200 pretty much within the first year.

My First Hire (2018)

A year after getting laid off, I made my first hire. I didn't really know what was the right next step to take, but I had a friend that actually approached me and said, I'd really like to work for you, so I kind of just jumped on the opportunity because he was incredibly smart and talented.

So I said yes, and I also feel like there's just this narrative in business that you need to grow all the time and be growing your team and scaling and figuring out ways to remove yourself from the business. But after he was with me for about eight months, I realized that it just wasn't a fit for me, and I let him go.

At the same time, I moved across the country to Montreal. At this point, I started hiring contractors to help me solve problems and take different pieces of work off my plate. I experimented with a lot of different ways of running my business in the next few years, which was really fun and I learned so much from.

These first few years (after relaunching) were a lot of experimentation, a lot of just getting really good at what I do and figuring out how to offer the best service for my clients.

How to have the best systems for making sure that everything that I do is high quality and consistent.  

Hitting A Plateau When The Pandemic Hit (2020)

When the pandemic hit in 2020, I did lose a good amount of clients in March. I think just because of fear and uncertainty and people wanting to cut back on budgets.

2020 was a year that I actually didn't focus a lot on my business. I think this was the case for a lot of people. I think the pandemic really made a lot of people evaluate what's really important in life.

I spent most of 2020 focused on things that were happening in my personal life. I had a lot going on (in a good way), but I did feel a bit bummed out about my business.

I just felt like I was kind of in a plateau. At this point, it had been three years and I was mainly still running client campaigns.

I knew I didn't want to hire a team, but I didn't really know what my next steps for growth were, and it stressed me out a little bit. I think another reason is that I used to always work from cafes or co-working spaces and I really struggled with working from home staying focused working from home during the pandemic.

I'm sharing this because I think it's important to note that business is always ups and downs and it's not always grow, grow, grow. I think it's important to acknowledge that.

I'm so grateful to my business though, that I was able to still make a decent income. Even though I wasn't focused on growth, I wasn't doing any sales at all, I basically just kind of kept my existing clients and kept focusing on them and their needs, but nothing really.

I felt a little directionless and normally my business in prior years has been something that makes me so excited and I can't stop thinking about it. So it was really confusing to me to not feel like that for the first time in years.

Experimenting With New Skills And Products (2021)

In 2021, things started to pick up, as soon as January hit I got an influx of referrals and clients. And that gave me a lot of excitement and energy again in my business.

Also, at this time I started learning video editing, which was something that I previously had always outsourced, but I felt like I wanted to learn. It was really exciting to me to have a new skill to learn and one that I could use to make my clients work even better.

I've always found that growth is pretty much the most important thing to me in my business. And I'm not talking about revenue growth or business growth. I'm talking about personal growth and growing my skills.

If I'm learning a new skill or pushing myself in a new way in my business, that is what really makes me so excited about it. And I think that was part of why in 2020, at that point I'd been doing it full-time for three years, I kind of felt the learnings weren't happening as quickly anymore.

I also signed up for quite a few programs in 2021. And one of them was all about how to sell digital products like eBooks, online courses, trainings, that kind of thing. This has been something that I've wanted to do in my business pretty much since I started it and just never got around to it.

I always found it easier to focus on selling services because it's a good amount of revenue upfront, as opposed to a course that you might sell for a few hundred bucks, and it's more guaranteed.

You can spend a lot of time building out a digital product, but you don't know if you're actually ever going to see a return from that. So, for that reason I've always really focused on my service clients. But in 2021, I did start to play around with some digital products and had a little bit of success with that.

I actually have a blog post on my website if you're curious to learn more about this. It's really long and in-depth, and I share the whole journey of creating that product from scratch and testing it with ads and testing different offers and different landing pages. And I've got Loom videos that I share as I'm going through the process, so you can really see what my thinking was and how I built it out into a little passive revenue stream.

I was pretty proud of it and proud to prove that I could generate passive income. But before I scale it, I really want to put a lot more time and effort into it. It's on pause for now, but it's something that I plan to get back into in 2023.

Putting My Company On Hold (2021)

Since I was planning to build out training courses, I started becoming more active on LinkedIn around September 202. After a few weeks of posting regularly on the platform, I started getting a good amount of job offers. One that caught my attention was for a senior director of paid social role out of a Toronto-based agency. And I ended up taking the job.

It was essentially an acqui-hire. They bought my clients, my systems, my processes, everything about my business kind of just got absorbed into theirs. And the reason I took it is the founder said to me that it would basically just be like running my business on a bigger scale. I was really excited about the opportunity to get to work with bigger clients, work with a bigger team and just try something different.

I was still feeling a bit of the lack of direction that I was feeling in 2020. In 2021 I had this new path that I was experimenting on with the digital products, but I still didn't feel quite certain of what my future held in my business.

I also just remembered how much growth I had at the last company I worked at, so I felt like it would be a good way to really just up-level my skills and get experienced with bigger companies and managing a bigger team. And then I could always go back out on my own in a year or two, if I wanted to.

Of course, I didn't last very long at the company. I ended up quitting. The environment at the company was incredibly toxic. I'll just leave it at that. And I should have vetted that better.

One thing that I say often, I can't remember where I originally heard this, but the phrase "action brings clarity" has always been so true for me.

As soon as I took that job, it was just so clear to me that my business was the right path for me and the uncertainty and lack of direction I had been feeling was just part of the process and that I needed to work through that and figure it out and get back to running my own business because that was the only thing for me.

I'm not saying that I'll never work for anyone else ever again, but at this point in my life, it's just not a fit for me.

Changes In The Industry (2021)

At the same time that this is happening in late 2021, there was a huge shift in the ad industry that had kind of been slowly happening over time, but iOS 14 really was the catalyst for this shift.

Facebook ads used to be about targeting and data analysis and optimizing your ad sets and all of these hacky ways of setting up your ad account. But there was a shift happening at this time towards making really good ad creative and doing UGC style videos and just making better ads in general.  

I had left that company in November and I took the rest of the year off to just analyze and figure out what was going on in the industry.

I did so much research. I spent so much time on Twitter, just following people, looking at what they were saying, and figuring out how I could make a company that was really positioned well within this new landscape.

One that would be more likely to stand the test of time because Facebook ads were changing and I knew that I had to change my business as well.

The Birth Of Carousel Creative (2022)

In January 2022, I launched my new company, Carousel Creative. I didn't actually launch the new name and branding until April because I couldn't decide on a name, and the branding and website and everything took a while.

But officially as of January, it's a completely separate company. And I like to think of it as a different company too, because it is very different than how I used to run things at Loop Digital. I feel like I really had to look at what was happening in the industry and really start from scratch and build a new offer for my clients that would help them succeed in the way advertising is now.

This year in 2022, I rebuilt my entire client base pretty much from scratch. It's been really, really fun and exciting this year. And I feel like I have gotten that excitement back in my business and I feel like this past year has been just so incredible and rewarding.

I'm going to create a separate podcast episode in the beginning of January as a year in review because I think it'll be interesting also for people to hear what I did to basically rebuild my company again from scratch. I say from scratch, but I had a lot of existing relationships and referrals that really helped a lot.  

I am really proud of what I've built this year and where I've got my company to. I'm earning more than I ever have, I am feeling better about my services and the quality of my services than I ever have, and I just feel like I'm doing really fun, rewarding, creative work for my clients.

Thank you so much for reading this blog post. It was quite personal for me, I don't normally share this much about what's going on behind the scenes!

But I love hearing about it from other people, and I really believe in transparency and being open. If this can help anyone else on their journey or provide a bit of insight to someone who's considering entrepreneurship, I think that would be amazing.

Thank you so much for reading and feel free to reach out if you have thoughts or questions about my journey.