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Kevin started Work Hero in 2018. They detail the beginnings of their company in their Starter Story interview: 
Q: How did you get started on Work Hero?
After spending some time in the corporate world and hating it, I got laid off and was forced to either find another job or start something myself. The idea of another job didn’t interest me, as I couldn’t seem to fit in with work/corporate/office life.
> Finding places where small and solo business owners hang out was a much better way to attract customers. Now as we move more into content marketing, we will be attracting the right customers.
I instead went with my passions at the time with fitness and sport and started coaching a local master (adult) swim team making $12/hour for a few hours of work a week.
This led to giving swim lessons and designing programs for triathletes (swim, bike, run) to accomplish a distance or open water swim.
I started taking this online, and I eventually got my start in the world of online business with triswimcoach.com – swimming training for triathlons. I hired VA’s, then teams, to help build and run my niche business.
And this building of teams and solving problems online led me to start Work Hero.
My original plan was to offer these three categories as a productized service, where businesses could pay monthly for the design/development/VA services, instead of having to go out and hire everyone themselves.
I quickly realized this was a little too much to take on and not what I wanted to do. I dropped the admin portion and focused on design and WordPress development.
However, I eventually realized that trying to do design AND WordPress support was not only not ideal for my customers, but it was also very hard to sell. In November of last year, I hit the reset button and dropped the unlimited design.
So we focused in on WordPress support and maintenance, doing the small edits (less than 1 hour), and helping businesses with all the headaches they experience with WordPress sites.
The “new version” of Work Hero was the right idea right from the start. We were able to start with a customer, then quickly added another customer, right from the start.
The conversations I started having with leads were so much higher quality. I wasn’t trying to sell them on doing so many things- and often wasn’t trying to sell them at all. WordPress maintenance and support were much easier to explain than design + WordPress, and our prices were able to come down making it more attractive to the small businesses I was talking to.