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Jonathan Sposato

Serial entrepreneur, Jonathan Sposato, was the first person in history to sell two companies to Google. Since then, he's become chairman of Geekwire and PicMonkey and has recently made waves in the Seattle community by announcing he will only invest in female-founded companies moving forward. Hear from Jonathan firsthand on how he’s always felt like an outsider but hasn’t let it stop him from achieving incredible success. His unique childhood and growing up as an Asian-American in a predominately white community shaped him to become, in his words, “more of a Nick Carraway than a Jay Gatsby.” Jonathan's wisdom on family, business and life in general is something everyone needs to hear. 

Updated on June 28
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Key Smash Notes In This Episode

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Jonathan Sposato is a serial entrepreneur, investor, and CEO. Currently a chairman of GeekWire and Pic Monkey. Jonathan is the first person to ever sell two companies to Google.

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A few years ago, Jonathan Sposato announced that he would only invest in female-founded companies.

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It took him a while to discover this, but helping others is what drives him. Whether personal friends or strangers.

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The seeds of that person were always there when Jonathan was young. He has always felt like an outsider.

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Jonathan's parents were Chinese and Korean, and at the time, his parents were not allowed to get married; it was seen as a very shameful thing. Jonathan ended up living with his mom, and had only met his dad recently, at the young age of 49.

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He wondered, "Will I like him?" or "Will I see him as a complete drag?" and considered many other questions. Jonathan has always viewed himself as an outsider in life. With his birth father showing back up in his life, in some ways that took away part of his story because he now has more of a sense of belonging.

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Absolutely. With a Chinese mom and Italian father who adopted him when he was young, there was no escaping it. Anything lower than an "A-" grade was not acceptable as his parents had high expectations for him.

Now that Jonathan is a parent, he realises that part of pushing kids to achieve high marks and extracurricular achievements is driven, at least in part, by a parent's ego and a desire to see them succeed.

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He has learned to lean into parenting and spend as much time with his son as possible.

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Jonathan figured out that other kids were just insecure, and if he could get good at various activities, like sports and music, and could become a popular kid, and put himself in a position where he was admired, not bullied.

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Jonathan looked all over for schools. He applied to Harvard, Stanford, and many other Ivy League schools and was rejected. He says life is still ok if you don't get into those institutions! Whitman College rolled out the red carpet for him and made him feel wanted.

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Relationally, he had friends from all over and found it very fulfilling. Academically, he was tracking to be pre-law at Whitman and had his eyes on Columbia Law School. His academic advisor questioned him on whether he REALLY wanted to be a lawyer, which sent Jonathan down the path of trying to determine where he wanted to go in life.

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During his senior year, his parents divorced. He had a lot to figure out and did not want to commit to 3 more years of school and the debt associated with law school.

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He wanted to get a high ROI on his efforts. When he opted out of law school after his parents divorced, he decided to go into the gaming industry and started a company that grew very quickly.

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When Jonathan worked at Microsoft, he met Heather. He was with Microsoft for 12 years.

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He saw it as a meritocracy, a lot of fun, and also rigorous. It was intellectually challenging and a great company to work for.

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He likes renaissance people who like to color outside the lines. In order for businesses to break out, he suggests to find individuals who don't focus just on their functional areas.

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Jonathan thinks you must be a student of it, but you don't have to be great at it.

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Only 2.7% of venture capital funding is allocated to female-founded businesses. He believes this must be remedied. Jonathan is trying to highlight a disparity and encourage others to lean in.

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