My Side Hustle Failures

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You may have heard about how Michael Jordan famously missed more than 9000 shots in his career or how Wayne Gretzky once quipped, “You miss 100% of the shots you don’t take.”

The wisdom here is recognizing that not everything you try will be a success, but that not trying at all is a guaranteed failure.

How about a baseball comparison? The only surefire NOT to get a hit is to never swing.

So as you might guess, I’ve had my share of side hustle failures along the way. I’d like to think of them as “valuable learning experiences,” because “failure” unfairly casts them as negatives.

But in fact when we learn from our failures, and apply that learning next time, they become immense positives in business and in life. My side hustle failures have served as my low-budget MBA program.

Here are some ideas and projects I’ve had that have flopped.

The World’s First “Open Source” Novel

I thought this would be a cool idea, kind of at the crux of crowdsourcing, publishing, and content creation. I envisioned building a community around a clever domain name like “collabowrite” or something, and having it praised as the new way to write.

But where Wikipedia and GitHub succeeded, I failed because I had no idea how to gain a critical mass of users, and didn’t apply any time toward market research, reaching out to authors, or anything of value.

Thankfully I didn’t dump any money into this.

Selling my Atlanta Condo

When I got transferred from Atlanta to California, I was in a rush to sell my 1-bedroom condo there. In hindsight, I think that was a bad move financially. Beyond recovering my down payment, I didn’t make any money on the sale, and the property could have generated positive cash flow each month if I’d rented it out instead.

I was intimidated by the thought of being a long distance landlord, and never even considered the option of hiring a property manager. I would love to have that rental income today, probably $200-400 per month in cash flow.

The Virtual Cellar / Wine Gifts 365

Living in wine country and looking for a way to carve out a tiny piece of the giant wine industry, I briefly and half-assedly attempted two wine-related sites.

The first was called The Virtual Cellar, and was built on GoDaddy’s Website Tonight software. The software was relatively easy to use, but was buggy and had severe functional limitations. The site sold a few wine club gift memberships but the volume and margins weren’t enough to get excited about.

The next incarnation of this site involved moving to a more “SEO-friendly” domain — targeting the very-competitive “wine gifts” keyword.

Initially I tried to rebuild using Joomla. Someone literally posted about it once in a forum, said it was better than WordPress, and I thought I would try it out.

Thankfully it was free software, because it’s not better than WordPress. In fact, it’s WAY harder to use and the site looked like crap.

After a few days (might have been only hours, I can’t remember), I gave up and installed WordPress.

wine gifts 365

But in the end, the platform didn’t really matter. I knew nothing about wine (and still don’t) and was not interested enough to become an expert. I was just regurgitating content from other sites and not doing anything out-of-the-box to add significant value.

There was no real reason for anyone to visit the site. And no one did.

A Sandal Site

After some initial success in the shoe niche, I tried to get even niche-ier and try sandals.

I figured since the platform was already built, it wouldn’t be too much work to change the headers and have a site that appeared even more relevant to sandal-seekers. And for a time it worked OK, but the performance was not improved enough to justify maintaining two sites with partially duplicated content.

Even though the business cycle of this side hustle was highly seasonal, it still required daily maintenance that in the end just took up too much time for the return.

A Handbag Site

After the sandal site flopped, I thought it would be a better plan to try a different vertical entirely to avoid the duplicate content issues.

With a development cost of a few thousand dollars, this was one of my worst investments.

carry my stuff

Because many of shoe advertisers also sold handbags and luggage, this seemed like a natural next step. In fact, many of my retail and network partners pushed for this expansion.

Unfortunately I did a poor job of market research and didn’t realize the breadth of sellers was much wider than for shoes. As a result, my comparison engine was not very accurate.

On top of that, product naming conventions weren’t as consistent as with footwear, which made generating useful comparison pages a challenge.

And commission rates were lower.

And it was time-consuming to manage.

And on and on.

Before Google’s exact match domain update, I had a brilliant idea to build this content-gift ideas site. It was going to rank well for every possible query because of my beautiful URL structure.

This is motivated, ready-to-buy traffic!

“Gift ideas for teachers” would bring up, and so on and so on, and the possibilities were limitless. I’m so smart, I thought. Why wasn’t anyone else doing this?

gift ideas site

Unfortunately, creating a content-rich and useful site for the limitless possibilities of search queries was either going to be incredibly time consuming or very expensive. Well, it wouldn’t have been that expensive but I wasn’t ready to make the investment on speculation.

And I overlooked the fact that I’m terrible at coming up with gift ideas in real life!

But even with the content in place, there are some well-funded and powerful companies that dominate Google for these gift-related queries. It would be a challenge to unseat them.


I hate failing. But the more often and faster I can fail, the closer I am to my next success. Like cold calling.

1. My biggest lesson: Don’t start stuff you don’t care about. 

A mediocre idea that you care deeply about has a far better shot than the “can’t miss” idea you don’t give a crap about.

2. Don’t start stuff you don’t have time to do right.

As I go along, hopefully my “batting average” improves and I can better my success-to-failure ratio.

In skiing, there’s a saying you tell people after they wipe out: “If you’re not falling, you’re not getting any better.”

It’s all about challenging yourself and trying new things. Like any unfamiliar activity, side hustles take practice.

And practice makes perfect.

“I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” –Michael Jordan

OK sorry for all the sports metaphors.

Benny Hsu, who found success in iPhone apps, shared a similar list of his past failures here. Do you have any side hustle projects that didn’t turn out the way you imagined? Let me know in the comments below!


(Edison image source)

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

9 thoughts on “My Side Hustle Failures”

  1. Love this! And totally agree that you do miss 100% of the shots you never take :-) Proud of you for continuing to ship and thank you for continuing to share your wisdom. :::High five::::

  2. This is terrific, Nick. This piece shows why you are an excellent entrepreneur: you have stamina, insight and a sense of humour.

    I’ll tweet the article. You may get a few more followers once you get over the embarrassment of having your head sticking out of the trench :)

  3. Thanks for the shout out Nick! It’s great to be honest about failures because a lot people cover them up, but they’re all learning lessons. We just have to be right once.


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