He picked the right headline, IMO. There are a gazillion profitable software businesses. Some work reasonable hours. There are very few funded software busin

He picked the right headline, IMO. There are a gazillion profitable software businesses. Some work reasonable hours. There are very few funded software businesses and I can think of exactly zero that work 4-day work weeks. I think Ryan's path is an awesome one. Step #1- get internet famous. Pay your dues, run conferences, build a popular blog, become a thought leader. Not a ton of equity to be built doing this, but it's a solid business. Step #2- Build a product tailored to the audience you've created. Step #3 - Tell everyone how effortless Step #2 is. :-) 37Signals took this path. Sarah Lacey did, too-- with PandoDaily. Om Malik is now an (awesome) partner at True Ventures (after being a really well regarded writer and entrepreneur with GigaOm). Edit: Actually, it could be argued that Patio11 of HackerNews took this path (but perhaps not on purpose). To be entirely clear-- I'm not being sarcastic. I think this is a smart/awesome path. Not much gives you more leverage than an big audience that's chock full of influencers.