There Is No Easy Online Business: My Eight-Year, -$27,000 Proof
Let me save you $27,000 and eight years in five minutes
Every online business model promises freedom. Most deliver expensive lessons. Don’t chase models—build an audience while you sell services and build products. The numbers and milestones that make it work are below.
Back in 2018, I started digging into all the ways people were supposedly making money online—affiliate marketing, dropshipping, print-on-demand, digital products, day trading, crypto, NFTs, freelancing, you name it. Every guru had their “best model,” and every video made it sound like the perfect shortcut to financial and locational freedom.
Eight years later, here’s the uncomfortable truth: I’ve invested roughly $120,000 into online ventures and made back about $92,000. That’s a $27,000 loss.
I’m not writing this as another success story. I’m writing it as someone who paid full price for an education you can’t get in any course—while building and selling a successful landscape mapping business that grew to over $120,000 in annual profit. My online experiments happened during evenings and weekends, funded by real revenue from solving real problems.
Here’s exactly where that money went, what failed, what worked, and why I’d probably do it all over again.
Dropshipping (Boldd Outdoor, 2018–2019):
My $2,800 Lesson in Cart-Before-Horse Syndrome Investment:
$2,800 | Return: $0 | Time: 6 months
About a year into running my mapping business (my actual source of income at the time), I dove into my first “passive income” experiment. I read Tim Ferris’ 4 Hour Workweek and I was ready to be the next millionaire digital nomad. I spent $2,400 creating an LLC for “Boldd Outdoor” and another $400 on Shopify hosting, themes, and apps.