It was refreshing to see how receptive he was to that feedback, though. Based on his responses, it seems like he is going to take an active look at how he handles employment status.
It by no means signifies a guaranteed success, but it is definitely a good sign when an entrepreneur recognizes legitimate criticism about issues that could make or break his business and actively seeks to address them.
Becoming compliant isn't a paperwork task. It's going to be expensive. He hasn't been withholding any taxes; he could end up owing as much as $1000 for each prior month he failed to do that.
The city and state his business is headquartered in (he's in DC Metro so it could be any of a bunch) is also going to tear into him for unemployment taxes and fees. We had drama with this even though we don't even have independent contractors.
It by no means signifies a guaranteed success, but it is definitely a good sign when an entrepreneur recognizes legitimate criticism about issues that could make or break his business and actively seeks to address them.