It pretty much boils down to funds and streetcred. A first time entrepreneur starts out with 5-20K in savings and no connections. A failed entrepreneur is also

It pretty much boils down to funds and streetcred. A first time entrepreneur starts out with 5-20K in savings and no connections. A failed entrepreneur is also in the same boat, no money, maybe a few connections. Meanwhile a repeat successful entrepreneur has a few mil in the bank, street cred to get VC $$$ and free media coverage. And that gets them that starting core of users to help grow the service during hte early days.