(0:00) Entrepreneurship as a kid, starting a business in high school that won a $50,000 contract (6:57) Role models: Mom with her home based piano teaching business was earning 4x his father (12:49) Paying for his own college education with the money he earned in high school (15:42) Getting a job in Silicon Valley in the late 90's (17:53) Timing matters: Chamath Palihapitiya was just 1 year ahead in college - "you can crash your car into a goldmine" (18:54) Getting a job as a PM at Allaire (28:05) Switching from engineering to marketing and placing the largest ad order of the year with Google (37:54) Getting a green card and starting a business in Boston, meeting Sergey Brin and Eric Schmidt and getting turned down for a job at Google (43:10) Getting a services business off the ground and earning enough cash to start buying houses and one car a month while getting no's from VCs (57:56) Getting the first VC funding for WordStream (1:02:20) Stepping down as CEO (1:10:18) Scaling Go To Market and dealing with Product Market Fit issues at WordStream (1:20:00) Getting to $55M in ARR and selling WordStream for $130M (1:24:30) Starting Customers.ai and motivation to do the next company (1:38:10) Doing things differently as a second time founder (1:45:50) Everyone should pursue entrepreneurship