How my failed part-time businesses took my career to the next level (and made me 25k outside of work)
“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”
~ Steve Jobs
I didn’t fully understand Steve jobs quote until recently. In 2012, I had a full-time job working in IT Support, one that paid the bills. I had also thought about starting something on the side, but didn’t really know where to start. At the time, Twitter was already huge and Instagram was just coming up — so I was very fascinated with social media, and had heard whispers of people making money on it. I had to learn more.
Exploring Twitter with Read the Throne
I was fortunate to have a friend that had a Twitter account doing just that. He introduced me to social media marketing. His Twitter account had around 150k followers, tweeting random facts, and he was able to monetize his account retweeting smaller accounts doing a similar thing. I then started my own Twitter account and named it Read The Throne.
I literally had a book with 700 random facts, and used that as my content. I was able to grow that account to about 10K before I actually retired it. I was losing more money trying to grow that account, than actually making money…
But the cost was worth it. When I got that first paying customer for advertisement, it was mind-blowing. This customer paid $10 for a retweet, which for the amount of time and effort involved (like 30 seconds), it was a steal. I wanted more!
Exploring Instagram with The Style Stack and Eat Spray Love
Around the same time, Instagram was gaining popularity, I thought I could apply the same social media strategy to Instagram. I created an Instagram account called The Style Stack with two other friends. It was based off of fashion trends that we like, primarily in the streetwear industry.
Through research I was introduced to black hat marketing, which I didn’t realize at the time. (Don’t do it, kids!)
I found a free Instagram bot that would allow me to automate the follow and like process based off of the hashtags in our target niche. In about a month I grew the account to 10k followers, and thought we could monetize by selling a t-shirt that was a fusion between streetwear and Marvel’s Iron man..
I created a WordPress website, that had a PayPal buy button. I was actually familiar with WordPress because during the my Twitter phase, I also tried to start a blog called Eat Spray love with five friends, but that didn’t last very long.
We launched our website, had the t-shirt on pre-order hoping to get tons of orders, only to get 1 person interested. We decided not to ship it, not only because of the lack of interest, but also no one did research on where to get our t-shirt. This felt pretty demoralizing, since we all had high expectations.
We stepped back and did more research and did two more t-shirt releases, to say the least were unsuccessful. I like to refer them as limited edition.
Even after three failed attempts, something inside me wanted to figure this out. There are lots of successful businesses, I wanted to make one of them.
Drop shipping with the Style Stack
After about a year of trying to gain followers on The Style Stack, I began to run the account solo trying growth hacks to drive traffic to my website. In 2014, I was introduced to drop shipping, which at the time I didn’t even know what drop-shipping was until I read a article on how to start an e-commerce store from Shopify.
It was finding pretty cool under the radar brands and advertising them on Instagram, so I figured I could consolidate some of these products into my own website and make a commision of sales.
Since WordPress did not support a shopping cart function, at least not for free, I switched to Big Cartel. I picked five products from five brands and started selling. I finally started making some extra profit. My commission was very small, less than 10% of the cost of the item.
In addition to my miniature commissions, I started getting a inquiries about doing sponsored posts. I had no pricing structure and no one to compare to, so I started charging $40USD per instagram share. I would try to post during peak times, which I assumed was in the morning, lunch or right after work, on pay day. Sponsored posts were doing so well that I would advertise for anyone, regardless if they fit The Style Stack’s audience. This was a huge mistake. Posting photos that don’t fit your audience doesn’t always go well with your followers. I lost engagement and it completely shifted my followers from streetwear to casual wear. I started to find it harder to curate content because it was no longer in my interests.
Selling Custom Products
I put The Stack Stack on pause and started to look at custom made products. Dad hats were trending (c/o Bryson Tiller). I had this idea to have a logo inspired by Drake’s OVO owl and the Toronto Blue Jays. I found a designer on Fiverr to create the design and connected with a supplier on Aliexpress, and I came up with this.
I had them in three different colours, black, white and pink. I was able to sell them to friends and family, somehow a couple were former NBA players! The supplier could never get the stitching right, so I never sold them online. I actually lost quite a bit of money on this project, but everytime I wear it, people will still ask me where I got it.
I quit The Style Stack, and started a new instagram based off my cat. I know it’s silly, but it was even more niche, and it was really easy to create original content, which was way harder to do on the The Style Stack.
I was able to quickly grow my Cats instagram account to 20K followers, so I started a store on Etsy, purchased animal bows ties on aliexpress and started selling those. Although I was able to grow my social following quickly, the quality of the product wasn’t very good, which lead to poor sales, and no sponsored posts.
So about five failing businesses in, and a few more I haven’t mentioned, I decided to take a break…
Selling Real Products with NA Stock Company
At the end of 2016 I landed a job in IT at Shopify. I don’t think I’d have known about Shopify if I hadn’t tried all these experiments. During my interview I talked about all these past projects, even though they were failed projects, I believe these stories helped me get this job.
My very good friend Huy Nguyen, who had co-founded The Style Stack and Eat Spray Love with me, had this idea for a stylish travel luggage tag. This luggage tag could be worn in many different ways, which made it more modern than the current country flag on your suitcase version.
We had a hunch on who our target market would be. I learned from past projects that going with a global audience makes it very challenging to connect with your customer, so we decided start local and stick to one audience. We were able to source a supplier ahead of time that shared some great photo samples with us.
We produced 200 luggage tags, did some in person marketing and sold it to friends and family. Doing this validated our product. I set up a store on Shopify fairly quickly since I was already familiar with other platforms, and took some high quality product shots. I used Instagram influencers to push leads to our website (pretty much what I did with The Style Stack, but on the other side of our table). We were able to scale our business online by continuing to work with other blogs and influencers. I also learned quite a bit about Reddit marketing and press release pitches, it’s like free marketing! Thanks Braveen, Amir and Lindsay for the tips!
These strategies, built on my past experiences, generated $25,000 in revenue in our first year of business. In just the first couple of months 2018, we already made one third of what we made in 2017. Looking back at all questionable things I tried, each one set the stage for the next. Each one was just a side hustle, but now could be something much bigger.
Closing Thoughts
A lot of these product-based business experiences fed my curiosity in product management. PM was something I was interested in, but not sure how to get there.
I think side hustles are a great way to explore areas you are curious about, and will give context around those areas. My side hustle selling luggage tags exposed me to a whole new set of problems that merchants face. I used that as a opportunity to try and solve that issue.
I’ll talk about intrapreneurship on my next post, but I’m now product manager on Shopify’s garage team working on experimental products. It feels like just the beginning for me, and I’m excited to see what’s next.