A Failed Side Hustle

Ever since I was young I was interested in small business. It started when I was 12 and picked up a book that my Dad was reading by Harvey Mackay, an entrepreneur/envelope salesman.

I was fascinated by all the stories of salesmanship, making a product and running your own business. It led me to starting a bunch of side hustle's when I was in high school and university.

First, was a clothing company I started with two friends. We got a government loan for $3,000, hired a designer to help us modify doctor scrubs and a local manufacturer produced them. We sold them to our classmates, made hoodies, a prototype baseball cap and then lost interest. That was followed up by designing websites for a summer gig. Or more accurately one website for a local car dealership (late 90’s designed with flash, just horrible). After university I switched again and teaming up with a friend, published a small business book about two sisters who started a cupcake shop friend. All of these failed.

But as Scott Adams, founder of Dilbert, would say.

goals are for losers, systems are for winners, and passion is bull#$!%
— Scott Adams

My system was to always have a side hustle. Worst case, I lose some money and I tell people I learned something, best case… it works. The next story isn’t one of those times.

It was a sock company. We saw an opportunity to create a funky sock line built around themes. Our first mistake was that we spent the first few months getting samples from all over the world from manufacturers. We tracked down factories in Lithuania, China, Korea and even found the same factory that made Happy Socks in Turkey. We had them send us a whole bunch of samples and pricing. It was exciting getting all these packages in, but it was expensive paying shipping for all of these samples. We found what we thought was a great factory and got started.

A batch of sock samples.

A batch of sock samples.

Our first line was the “City Line” with a sock patterned like chain link fence, a NY city manhole cover, a graffiti brick and finally the tube sock which looked like a London Tube map. We came up with the ideas, then posted a job on ODesk, now upwork and found designers in Romania and all over the world who created great designs in a matter of a few days. We sent these to the manufacturer and went back and forth discussing pantones, cotton thread types and all of the things we didn’t know about. We were learning the sock business.

A few weeks later our first samples arrived and they were horrible. The quality was nowhere near our samples. That’s where we learned we shouldn’t have been ordering generic samples, but our actual designs right from the start. They were thin and you could see small holes in the toe seam.

Yup, people notice these things. 

Yup, people notice these things. 


We reached out to the factory, tried to work with them, but it wasn’t going to work. So we went to a Korean factory that made Sock it to me’s socks. They were selling a ton of socks so they had to be good right? They came back with decent quality, but we still wanted it to be a premium product.

Next we tried the factory in Turkey that made Happy Socks, but our designs were complex and they had long threads on the inside which made them feel weird to wear.

Simple standard design on the right. Our complex design on left. Too hairy!

Simple standard design on the right. Our complex design on left. Too hairy!

On and on we went until we finally landed on a manufacturer who could communicate wonderfully and had a great product. We were ready to pull the trigger. Right before we ordered my partner asked “what if this doesn’t work?” You see, this manufacturer had a minimum of 2,000 pairs per design. If we couldn’t sell them, we’d be in trouble. So we made a great decision and started hunting for a manufacturer based on a low minimum. It took a few more months, but we finally found one. High quality socks, great communicator and 100 pair minimum. Jackpot.

As the factory started our order we got serious on the ecommerce front. We set up shopify, which is an amazing place to host an e-commerce site. We were new to the e-commerce world, but we found it super easy to set everything up. Next, we set up our fulfillment house, Shipwire. We designed everything to be streamlined where our manufacturer would ship directly to Shipwire, our fulfillment house and then whenever an order came through Shopify, Shipwire would automatically send the package. Genius.

Why didn’t we use Amazon as our fulfillment house? We thought Shipwire was easier to set up and they had the ability to break down packages. So you could pack things in sets of five (say for wholesale to retail stores) and then if they needed them for an individual shipment they would open a pack of five and ship the one they needed. It seemed smart. Going back in time, I’d set up Amazon. They’re eating the world.

So a year or so after we started the funky sock game continues to be filled with competitors and our product is ready. It flies to the fulfillment center and we’re thrilled.

The socks look good.

Our friends place a few orders, everything is working seamlessly. But we’re tired. We both work full time and have families that need our time too. So our pace slows down, we don’t market effectively. The cost per click for advertising was 10x what we had calculated earlier and made it impossible for the economics to work. We make a few pushes and got picked up for a big daily sale site, but nothing stuck. Weeks go by. Months go by. Our sales are not taking off and we’re putting in less time.

Looking back, I wish we pushed harder. I wish we went to trade shows, knocked on boutique doors, sent out samples to influential people. But we were tired. And we were always better at creating than marketing. Soon enough we realized we had lost our enthusiasm and should shut down the business to stop the monthly fees. But we came up with the idea to sell the company instead. We were convinced it just needed someone better at the helm to market it. So we put the site up for sale on flippa. The name, site, inventory, everything. Now flippa usually sells websites so ours got lots of attention as it had a physical product. In short order we sold for a few bucks and were out.

This is where I’m supposed to say we learned a lot. Like importing products from a different country, setting up an e-commerce site, manufacturing, etc. And we did. But we also failed and didn’t make any money. I see all these stories about side gigs that make hundreds of thousands or millions, but those are the rare stories. I wanted to share this experience to help people understand that side gig failure is common, even though we typically don’t read about them. Hopefully this helps you avoid some of the mistakes we made.

But even after all these failures I can’t stop having a side hustle. I find it fun to create and connect and as a now billionaire once said:

It doesn’t matter how many times you fail, you only have to be right once,
— Mark Cuban
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