I was maybe a little too excited to read "When to Jump"
(https://www.amazon.com/When-Jump-Have-Isnt-Life/dp/125012421...) about taking a big risk in making a major career/life change against perhaps the wishes and/or expectations of your family, friends, colleagues, society, etc from an author I hadn't heard of before (but somehow got Sheryl Sandberg to write the forward for and Reid Hoffman to endorse) who left a cushy VC/finance job to travel around the world to play squash for 2 years.
After doing a little more research, I found that the author grew up in a wealthy east coast family, is a close blood relative to Sheryl Sandberg, went to an Ivy League school (likely aided by privileged upbringing and family connections), landed at a prestigious finance/VC firm straight from college (probably made possible again by an Ivy league pedigree/family connection), and could easily make the "jump" to doing something that paid nil for 2 years due to this enormous safety net of family wealth that most people simply don't have.
If there's one thing about the Travis Kalanick saga I wish the media would've told is that he is a rare successful founder who legitimately grew up in a middle class family and struggled for many years post-college trying to get to ramen-profitability on a series of failing startups before hitting it big. This is strictly in contract to the Zucks and Spiegels of the world who grew up very wealthy and went to the best schools and could take on the big risks associated with entrepreneurship because if everything failed they still had that big safety net to fall back on.
After doing a little more research, I found that the author grew up in a wealthy east coast family, is a close blood relative to Sheryl Sandberg, went to an Ivy League school (likely aided by privileged upbringing and family connections), landed at a prestigious finance/VC firm straight from college (probably made possible again by an Ivy league pedigree/family connection), and could easily make the "jump" to doing something that paid nil for 2 years due to this enormous safety net of family wealth that most people simply don't have.
If there's one thing about the Travis Kalanick saga I wish the media would've told is that he is a rare successful founder who legitimately grew up in a middle class family and struggled for many years post-college trying to get to ramen-profitability on a series of failing startups before hitting it big. This is strictly in contract to the Zucks and Spiegels of the world who grew up very wealthy and went to the best schools and could take on the big risks associated with entrepreneurship because if everything failed they still had that big safety net to fall back on.