Jake Gibson is a prolific angel investor in SF whose investments include the likes of Datafox, Meadow, the new on demand delivery service for marijuana and TripleByte, the amazing recruitment platform for engineers co-founded by YC’s own Harj Taggar. Prior to his transition into investing Jake co-founded NerdWallet, a startup focused on offering price-comparison tools for financial products where he is to this day an advisor and if that was not enough he is also a mentor with our good friends, 500 startups. In Today’s Episode You Will Learn: 1.) How Jake made his way into entrepreneurship and made the transition into the world of investing? 2 2.) Why did Jake decide not to take external money when growing Nerd Wallet? What does Jake think are the pros and cons of bootstrapping? 3.) What was it that attracted Jake to the world of investing? In the opening days, how did Jake operate as an angel? What was Jake’s deal sourcing like? 4.) Why has Jake decided to have a sector diverse approach when it comes to investing? Does Jake think investor specialization can be beneficial? 5.) Looking back at your time investing, has there been a pareto’s principle happening? Has 20% of the work produced 80% of the results? If so, what 20% was that and how do you plan to further increase this segment? 6.) How does Jake aim to differentiate himself from the mass of other angels? How important do Jake believe angel personal branding is? Has differentiation been the hardest aspect of the investing experience for Jake? Items Mentioned In Today’s Show: Jake’s Fave Book: Leaving Microsoft To Change The World Jake’s Fave News Source: Twitter Jake’s Most Recent Investment: Meadow As always, you can learn more about SyndicateRoom here: www.syndicateroom.com and see Jake's latest tweets here: www.twitter.com/iamjakestream

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“What did the council decide on item 42?” — answered with the speaker and the moment.

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