5-years of Self Employment: Wins, Losses, Beer

Originally written & shared January 2024.

How ya doin? It has been a while – just about 5 years in fact.

I figured it’s as good a time as any to give an update on my professional life and share my story about self-employment, entrepreneurship, SEO, and digital marketing.

If you’re not a big reader, that’s okay. Here are the highlights:

  • Built a surf-inspired art business that has sent about 3,000 of my posters all around the world.
  • Built a portfolio of owned and operated content websites that generated over 11,000,000 pageviews from 2020-2023.
  • Generated over 7 figures in revenue from 2020-2023 and was able to pay myself a whole lot more than anyone else ever wanted to pay me.
  • Got to collaborate and reconnect with friends and coworkers who had taken a similar self-employment path.
  • Learned a lot, tried a whole bunch of new things, and failed and stumbled a fair share too.

Here’s the story of how that all went.

Trading Digital for Physical

Halloween of 2018 was my last day of work at the second good job I had quit within the last 6 months.

Leading up until the day I gave my notice, I was really struggling with what I was doing and why. In many ways it felt like I was where I was due to no choice of my own.

While I know that’s not entirely true, I do know I wasn’t spending the majority of my time how I wanted to be. I was feeling uninterested, unchallenged, and a bit stuck.

So, I decided to cash out my retirement account and start my own surf business making fins out of bamboo, hemp-cloth, and plant-based epoxy.

The Wave Arcade project, a name I came up with when I discovered my interest for fin design while living in Utah and daydreaming of the ocean, began.

I ditched the computer, SEO tools, and website recommendations for coveralls, power tools, and product development.

At the end of my last day of work work, I headed down to Culture Brewing in Encinitas to do some initial brainstorming and celebration of the new journey I was embarking on.

After a week of full days cutting, shaping, and sanding bamboo in the detached one-car garage of the condo complex I was living in, the neighbors started to complain about all the noise and dust. Rightfully so I guess, but still – what a bummer.

I found myself facing my first challenge so early into my new venture.

Unsure of what my next move should be, I think I spent the next few days surfing, playing with my dog, and otherwise not working.

Eventually I found a maker’s space in a neighborhood I used to live in during my undergrad at San Diego State.  And once again I found myself doing a morning commute from North County down to San Diego.

About a month later I had finished my first production run of handmade fins, ordered a box of t-shirts with my first designs, and put the finishing touches on about one hundred koozies I made from upcycled wetsuits.

I updated wavearcade.com with my products and waited for the orders to roll in.

That didn’t really go how I thought it would.

But after some light PPC campaigns, a little social media, and talking to some folks at the beach, some orders did finally start to roll in.

Certainly not enough to break even nor sustain myself at that point, but things were moving in the right direction it seemed.

That was until some customer feedback and more product testing of my own that I realized my designs would need to be totally reworked.

My fins were breaking and needed a redesign.

I spent the next 6 months or so refining and testing my designs (i.e. surfing a lot) and filling in some gaps with some SEO consulting here and there (thanks Nick!).

I ventured into some new upcycled product testing with hand planes made out of dead palm fronds, one of which wound up as a finalist in the 2019 Vissla/Surfrider Creators & Innovators Upcycle Contest.

By the end of 2019 I had a design that was working, I had expanded the art & design side of the project, and I was feeling like I was getting the hang of self-employment.

At the start of 2020 I set up a table at a local marketplace that happened to be run by my favorite place for a pint, Culture.

I was getting bulk order requests for my upcycled koozies, most of which I had to turn down, but I did end up selling the rest of my stock to Smiley’s Saloon in Bolinas.

Things were feeling good, but I think you can tell where this is going.

Back to Digital

The marketplace shut down for good when COVID lockdowns hit, and all my progress of the past year felt like it came to a screeching halt.

Considering in-person stuff and even surfing was out of the picture for a while, I needed to reevaluate my options.

I launched an Etsy shop for the artwork side of Wave Arcade and pivoted more toward the digital side of that project.

But I knew that wasn’t going to be enough, and my retirement runway was getting lighter and lighter.

While grasping at any straw I could think of, I logged into the analytics accounts of some personal websites I had created as small tests.

I hadn’t touched or really looked at the sites since I had launched them, but to my surprise, they’d been slowly and steadily growing in the background.

I guess I did know a thing or two about content and SEO after all.

A year away from day-to-day digital marketing had done me some good.

It felt like an exciting and interesting challenge again.

At that point, my experience was mostly limited to content and SEO. I knew I was going to need a bit more than that to make these sites work and grow.

I got to work creating new content, learning some CSS and Javascript, setting up and optimizing display advertising, and researching affiliate offers.

And when I needed a break, I would work on some art and designs for Wave Arcade.

My working flow felt good again, and it seemed like I was onto something.

Traffic continued to grow, and my websites’ $100 months soon turned into $1,000 months while my Etsy shop continued to gain traction too.

Lockdown Lifts, Libations & Lead Forms

After some of the COVID lockdowns had eased, I met a friend and former coworker for a beer at Culture, which if you’re paying attention so far is where everything pivotal in this story occurs.

We were talking about motorcycles when I mentioned one of my websites that was inspired by some of my old bike restoration projects.

Coincidentally, he had been working with another former coworker on an advertising project that sounded like it would align well with my site.

By the end of the month we worked together on launching the network on two of my websites.

Two months later at the end of 2020, my websites had more than doubled in revenue.

My focus shifted heavily into content optimization, new content, new features, and new sites.

By the end of 2021, traffic for my projects grew by over 200% and revenue by over 1,000%.

By the end of 2022, traffic grew by another 40% and revenue by another 85%.

During that same time I was still able to refine and expand the Wave Arcade art series.

Between 2020 and 2023 around 3,000 of my posters reached customers all around the world. Appearing everywhere from people’s homes to big and small businesses and even some set dressing in some productions I can’t talk about.

In addition to content and art, which really started this whole thing, I was able to:

  • Dive deep into A/B testing and ad management.
  • Create some interactive tools, features, and resources to compliment the written content on my websites.
  • Create video content and other visuals.
  • Acquire a competitor site.
  • Manage outsourced content production with some more friends and former coworkers.
  • Incorporate some APIs into some of my sites.
  • Mess around with AI.
  • Experiment with some Python, large datasets, and programmatic SEO.

Needless to say, I was able to keep myself interested.

Troubles & Turbulence

After almost 2 full years of traffic and revenue records month over month, I figured that’s just how things were going to work.

By the first half of 2023, it was clear that was not the case.

Between Google algorithm updates and some broader industry effects for some of my biggest revenue sources, despite still doing much better than my prior day jobs, I was definitely not going to be setting any new records that year.

Throughout the second half of 2023, the hits kept coming.

Up until last year, my websites had managed to remain unaffected by algorithm changes.

Considering my background in SEO, organic was where I placed most of my focus and effort for traffic acquisition. I can see now that was a big mistake.

With each hit throughout the second half of the year, my mistakes over the past few years in terms of my own websites came into full focus.

Anyone who has worked with me before could probably tell you that I’m pretty fast and effective at getting things done.

While I consider that one of my strengths, I think it may have been a double edged sword for my work over the past few years.

One of the reasons I was able to grow so fast was because I had a process and system for building websites, creating content, and growing organic traffic.

It worked really well for a while, and for the most part, I’m proud of the sites that I’ve built.

But, with a continually growing portfolio of sites, that didn’t leave much time for me to focus on other channels nor build stronger relationships with my visitors.

While I had dipped my toes in things like Youtube, some social media, PPC, and newsletters, I hadn’t given any one of them enough time to figure it out yet.

I think the saying, “If you want to go fast, go alone…” probably applies here.

I was able to move extremely fast, but it appears I’ve hit a major obstacle that could have likely been avoided if I had worked with others to focus on different channels and nurture better relationships with my sites’ audiences.

Either that, or not try to work on 10 sites at once. But hey, what can you do, ya know?

2024 & Beyond

AI tools and search features, constant algorithm updates, super-short-form videos eating the world and our attention spans – things are changing… as they always do.

If your business’s primary focus is digital, these changes are probably front and center.

The micro niche website, which you could probably describe some of mine as, will not be as effective with an organic-only strategy. I wouldn’t recommend an organic-only or even organic-primarily strategy at this point.

Even Etsy, which has been the primary channel for my art, is getting flooded with AI-generated work and making discovery there more challenging.

The point is, while third-party platforms are a necessity, they are not your friend. Diversification is key.

The best advice is to go back a few years and start a foothold on the channels where your audience spends their time with the goal of creating more direct relationships with them via a newsletter or some other means.

If you can’t go back to do that, I guess the next best thing would be to do that now.

If you’ve mostly worked solo like I have, you’re going to have to figure out how to consolidate your efforts and/or offload some of the work to be most effective.

This year you can find me making more Wave Arcade art, taking a hard look at my portfolio of sites, exploring strategies for new channels, and probably working on some brand new projects too.

While I find myself facing a bit of uncertainty like when I started all of this in 2018, I know I can always head down to Culture and think on it over a pint or two.

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