He bought Infusionsoft for his landscaping business (he wasn't yet focused!)
He was not a good businessman early on.
He hired a bookkeeper, and she never billed many of his customers.
This all hit as 2008 was collapsing the economy, and it was too seasonal, so he shut the landscaping business down and focused on web design, and that morphed into Memberium.
One of his website clients at the time stiffed him on a big project he built that cost him $20,000 out of his own pocket.
From then on, he got paid upfront.
He went back to being a solopreneur.
He had to sell and fulfill. It was good for a while because he honed all of his skills, which helped him scale up later.
He was making free video tutorials for Infusionsoft users.