The thing is though that a lifestyle business is quite stressful in many ways: you have to innovate like a technologist while also having the enormous stress of

The thing is though that a lifestyle business is quite stressful in many ways: you have to innovate like a technologist while also having the enormous stress of bottom line responsibility for profit & loss...without the possibility of getting more hands to help you out through growth, or the margin of a large company to tide you over should times get bad. 37Signals is not the typical lifestyle business. A business you've never heard of, or which you frequent without paying much thought, is the typical lifestyle business. No one will make a movie about such a business, or be in awe at its growth rate, or fund a bunch of competitors to get into the space. It certainly has its pluses and minuses, but if you are an ambitious kind of character who loves the clang of battle, there's a reason that a lifestyle business seems like a defeat. Finally, it's not much easier to build a lifestyle business that actually makes more money (and hence provides more freedom) than your alternatives. If you have such talent, you could probably make more of an impact either at a big company or by joining/founding a top startup.