How SoftwareCW moved from eBay sales to instant downloads
Colton Wiles, Founder and CEO of SoftwareCW, leads an online retailer selling discounted, instantly downloadable software licenses. Wiles describes how early eBay sales grew into a business, why the company shifted from boxed software to digital downloads, and what new sellers should learn about sourcing, brand permissions and fraud.
New software sellers should learn the business basics, including procurement, brand permissions and fraud protection, before investing in paid courses and tutorials. SoftwareCW’s shift to digital downloads also reflects customers’ expectation of fast delivery, with orders arriving in under 30 seconds.
How did the business start, and what makes it different from others in your space?
I started dabbling in business in high school. I took several Computer-Aided Drafting (CAD) courses because I enjoyed them, and it turned out I was quite skilled. I was sent to regional, state, and national competitions, where certain brands sponsored the events. I ended up winning a lot of CAD software, which I then sold on eBay.
In short, by 10th grade, I would leave school at 3:10 p.m. and spend the afternoon returning calls from established companies, selling tens of thousands of dollars’ worth of CAD software.
What sets us apart today is how frictionless, clean, and instant our ordering process is.
How did you win your first customers, and where does most new business come from today?
As mentioned above, my first customers came from eBay in 2006. I wouldn’t call it a business at that point—more of a side gig. By 2026, the business has grown significantly and built a strong reputation not only with customers, but also with suppliers and brands.
What is one decision that changed the direction of the business, and one mistake that taught you the most?
The biggest decision that changed the direction of the business was shifting from selling only physical boxed software to offering only digital downloads.
The mistake that taught me the most came early on: I learned how much counterfeit software is on the market. I imagine that is true in many industries.
What has changed in your industry or in what customers expect, and how have you adapted?
Across industries, not just software, customers now expect to receive what they ordered almost immediately. We adapted by streamlining our systems so that customers receive their digital software orders in under 30 seconds after placing them.
If someone were starting a business like yours today, what should they do first, and what should they ignore?
They should first research and learn the basic mechanics of running the business, including the following: – Inventory procurement – Legality of selling certain Brands without their permission – What E Commerce platform to use (Shopify, Magento, etc) – Advertising channels (SEO, Google/Microsoft ads, Social Media, etc) – What policies they will offer to customers – Fraud Protection (fraud is rampant in the digital download software industry)
One thing I recommend ignoring is the flood of paid ebooks, courses, blogs, and tutorial subscriptions. They rarely teach anything you cannot learn yourself. In reality, their main lesson is how to make money by selling paid ebooks, courses, blogs, and tutorial subscriptions.
Thank you to Colton Wiles and the team at SoftwareCW for sharing what actually worked with Leaders Perception readers.
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