I'm sympathetic to his goal because I have similar aspirations to have more freedom.
What I might miss in his situation is working as part of a team with others: business people, SW devs, design
What I might miss in his situation is working as part of a team with others: business people, SW devs, design
That's definitely the thing that I miss most.
It's not just the social interaction but the feeling of growing together. I like working on a team because we're all learning from each other.
It's just not the same with freelancers. When everyone's a full-time employee, there's a permanence to that, and it encourages everyone to invest in each other and invest in the team. With most freelancers, they could quit at any time, so there's less incentive to take time to teach them. And the power dynamics are weirder so it's much harder for freelancers to tell me I'm doing something stupid, whereas peers or people senior to me felt much more comfortable doing that when I was an employee.
Technically he does have a team of freelancers...
Ideally I'd find people I enjoy working with and who have complementary skills.