"Access to venture capitalists: Raising money is incredibly hard and incredibly distracting. The faster you can get it done, the faster you can get back to building something people want. YC is the perfect forcing function to help you raise capital. Network: Being an entrepreneur is a lonely path. There are few people who truly understand what you’re going through and even if your friends (or parents) are well meanin…
Next, you are also massively undervaluing Susan's work. Did you read that she kept failing for 2 years and still kept at it? If you were already rich, would you go through that kind of hustle as opposed to enjoying your margarita on a private island? Did you also read that she was pregnant while making her attempt and with 3-year baby in hand? Do you have any idea how is it like to be pregnant and working on something as taxing as startup while also taking care of 3-year old? If you don't I humbly suggest to ask this to your mom.
Next, Loopt was innovative in its time but unfortunately way too easily and quickly copiable. Being still able to sell that is actually a business success and tells you something about Sam's ability to win over investors and break a way against odds.
[1] http://www.amazon.com/The-Launch-Pad-Inside-Combinator-ebook...