Started an online business & became a digital nomad - swings, misses and lessons

jaymeedawn333

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I have run local service businesses in the past, and had a reasonable amount of success with them, and even sold one. I’ve dabbled in an online business with only minimal success, but the idea has always appealed to me. The freedom from location in particular.

The pandemic allowed me to take some time and make some changes in my life. I came across the idea of a design subscription business and decided to set it up quickly and test (validate) the idea.I went to Dribbble and DMed people looking for designers, and a guy signed up right away.

He ran an Amazon stores and wanted his product photos edited.I had a designer friend of mine do some of his jobs. His jobs were not complicated, but he didn’t really believe in providing briefs, yet had a certain outcome in his mind. This didn’t jive very well with my then understanding of a productized service should go, so I refunded him and parted ways, but… I saw the potential.

I then went on an interviewing/hiring spree, and brought on a few designers. Early on, I wanted quality to be a differentiating point vs. my competitors, so I worked on the hiring and testing process quite a bit.

I continued to use Dribbble to do outreach, and I got around 3 clients within the first 2 weeks of Feb 2021. I was now in business properly, and I registered the business as a federal corporation in Canada. Amazingly enough, a couple of those first clients are still with us ~ 3 years later!

If you’ve been thinking about starting a particular business, my advice would be to just get it started to the point that you can validate the idea. Throw up a website and get some traffic to it, or reach out to potential clients and see what happens. You might even find yourself with paying customers right away! If not, try something else.

I then made a plan to go digital nomadic on October 1st, 2021, and all I had to do was smoothly sail through the next few months, or so I thought. Over the next few months:

👉 I ran a few Facebook ads and got a couple of clients at around $150 CAD acquisition cost, which was great

👉 Lost 3 clients in 1 day, which felt pretty shit

👉 Tried a service called Cleverly that promised me the moon (clients from LinkedIn), and it didn’t work at all

👉 FB ads didn’t continue to perform unfortunately, so I hired a guy/kid who ran successful campaigns for product-based businesses to look at my FB ads; he couldn’t do anything with it, and concluded this business is not viable lol

👉 I tried out Google Ads, but got no results from them. A reddit expert reached out to me to evaluate my account for areas that need improvement, and came back and told me that he found nothing to fix or improve.

👉 Kept up the outreach on Dribbble and slowly but reliably added clients every month

I came across a couple of potential clients that wanted more commissioned art than graphic design. They were also individuals, not businesses (yet), and they weren’t easily able to afford the service. Those experiences clarified for me that I prefer working with existing companies who have ongoing design needs. They get tremendous value, and they’re not hurting for cash.

October 1st finally rolled around. By this point I had gotten rid of my car, most possessions and now my condo. I hopped on a plane to Miami to start my digital nomad journey. I really loved my ~3 months down there. While my friends and family were deep in winter, Miami was blue skies, 27 degrees (the water was 29 degrees!), windy, Cuban food and great drinks. Americans are amazing; so open to new friendships, and I got to make a few new friends.

I came across challenges that digital nomads might be able to relate to, such as balancing work and enjoying the place you’re at, but overall, 2021 went well for the business, growing the whole time.

I spent January 2022 in Dubai, and the rest of the year in Mauritius, Dubai (again), Thailand, Malaysia, Singapore and Australia.

I have to say, it felt very freeing living as a DN. Spending 1-3 months and leaving before the welcome wears off is great, as is seeing different places and different lifestyles. However, the best part might be “the fresh start” with each new place. Can’t remember what book it was, but I read a book that talked about giving yourself the advantage of a fresh start regularly.

While the DN experience was great, my main method of getting clients (Dribbble) slowed down dramatically in 2022. Compared to my competitors, my churn was actually super low. Clients tend to stick with us for long periods, and are very happy with the service, but there is still a certain amount of churn. During this time, lead gen is something that got really tiring for me and I definitely neglected it.

An aspect of this business I’ve appreciated is being able to hire people. My previous local service businesses were run very lean, and this is the first time I’ve actually hired people. I felt grateful for the ability to give people a living.

I started off being a very carefree, lax, friendly “boss” to my employees, but I noticed that gradually, a few of them started to take this for granted, and then started to abuse it. I didn’t want to have a knee-jerk reaction, but I did gradually adopt a more neutral attitude towards them, and now I think it’s more or less the correct balance.

In August 2022 my first full time hire decided to quit with basically no notice. This was quite the fire to put out, because one of my clients had signed up for a package with exclusive access to him. They really liked his style (even though it was actually not as good as other designers). I had to scramble to replace him with other designers that could do his style, and figure out Google Drive permissions, ownership and a lot of other issues. That led to me redesigning the hiring and work structure so that backup designers are always available, based on time zones.

I decided to look at lead gen again, and remembered that cold email worked really well for me in other businesses I’ve ran. I also learned that it was the main method of lead gen for one of my competitors, so I gave it a shot, using Instantly and 40 Google Workspace emails with leads from Apollo. Unfortunately, I didn’t really get any results from this, or the Instagram DM outreach I tried. I will be re-attempting this within the next 1-2 months.

I spent the last couple of months of 2022 and first few months of 2023 in Australia. The time zone in Australia is basically not on planet earth, so this was a new challenge. While down under, I had still not found a good solution to lead gen, so my partner said let’s go back to Canada and start a cleaning business (a la Rohan, aka @spiderkiller007), so we got on a 14 hour flight.

That wasn’t the only reason. I stored what was left of my possessions in my friend’s basement. He got it in his head that his wife was cheating on him, with a woman (her friend). Tracking devices from Amazon, a PI, “bro” expertise and surveillance, false assault accusations, handcuffs, lab tests of panties for DNA, stolen passports, 300 m restraining orders, and more meant that my stuff wasn’t safe, and might even take the brunt of a misdirected bout of retaliation. I had to come get my stuff and move it to a storage facility.

Once that was done, we started that cleaning business, and even made a profit from day 1, but ran it for only 7 days and then decided to sell it, because I realized it was a lot more hands-on and locally-based than I wanted it to be. However, if you are looking for something to get started with, and especially if you’re US-based (or maybe Australia-based), I would recommend it.

After selling the cleaning business, I decided to double down on the design subscription business, which was still operating, but not at the same rate as 2022 and 2021. For whatever reason, at this point, I decided to rebrand the business.Looking back, I realized that the design business is something I’ve enjoyed so more than other things I’ve done in my life so far. Realized I’m much more of an art and design aficionado than I ever previously knew, but it’s also been really satisfying being able to fulfil a need for your client base regularly.

I reached out to past clients and got some to come back, and got some referrals as well. New clients that came on loved the service, which was great to see. One of our clients runs a successful podcast in their space, and wants to feature us on it, so I’m really looking forward to that.

I’m not really big on social media, but when I sold the cleaning business, I followed the format I saw a guy in one of my FB groups use to sell his business, and improved on it slightly. I wrote a FB post and shared it in a few groups.

These posts got a lot of attention. I directed everyone interested to a Google form, and then a video I made with some numbers and projections, and had more than 100 people from across the world actually interested in buying the business, along with many others who just wanted to connect and talk.

This process worked so well, I was able to follow the exact timeline I had in my mind, and even had the money in my account the following Friday, just like I planned. I found this experience pretty eye-opening.

Through this I realized that something I’ve completely missed is networking, and how much of a part of growth it can be. I’ve wanted to network with like-minded people everywhere I’ve gone, and despite meeting plenty of people that were so curious about the DN lifestyle, I had trouble finding the right demographic that I wanted to connect with (other entrepreneurs).

What’s next for me is continuing to grow the business, testing and adding new inbound lead strategies, and getting to the point where I can hire the right growth partners. There’s so many companies needing designers out there, I wish I knew of a better way to put myself in front of the decision makers, but I’m going to keep trying different methods.I have many more things in the works, but I’ll share those as they happen over the next few months.
 

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