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Jonathan Sposato

Jonathan is a Seattle entrepreneur with two successful exists under his belt. He is currently the Chairman of PickMonkey and Geekwire, a prolific angel investor, and a generous donor to various non-profits. When Jonathan was a little kid, due to circumstances he ended up living in Hong-Kong with his grandparent until eventually reuniting with his mother in Edmonds, Washington in the 1976. Presented a new set of challenges for a kid who did not fit in, Jonathan learned to adopt and to persevere. This episode is his story of success and challenges, and what is going to impart on his child for the life ahead.

Updated on December 27
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Key Smash Notes In This Episode

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Jonathan was born in London to a Chinese mom and a Korean dad. Due to circumstances, his mom ended up raising him on her own. At first, they lived in Brooklyn Heights, NYC, and although it was not quite a ghetto, it was not a great neighborhood at the time. They were poor, and unable to provide great care to Jonathan, his mom sent him to live with grandparents in Hong-Kong.

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Even though Jonathan did not speak Cantonese, nor did he really know much about Hong-Kong or his grandparents, he says it was a fantastic experience. He learned a lot and got to meet his extended family.

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Jonathan Sposato wrote a book about this called Better Together, in which he talks about gender and how we can do better in the business by having more women be in positions of senior leadership.

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Having some luck in life enabled Jonathan to feel very grateful for what he already has, while giving him grounding to not take things for granted and to always appreciate how far one can go. He knows first hand how much impact one can make even by simply helping others to have a sit at the table, so to speak.

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Microsoft taught their employees to be great engineers and managers, and marketers and strategists and technologists, but very few had any kind of mentoring on how preserve wealth or to be philanthropic with it.

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Jonathan says he knew he had a mom, that she lived in New York, and that she would send back money and Christmas presents, but he did not actually see her for six straight years. However, he has nothing but fond memories of his childhood in Hong Kong, growing up in a massive city, gaining independence, learning a lot.

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Jonathan's mom married Dawn Sposato, who subsequently adopted Jonathan as his son, and to honor that gesture Jonathan is keeping with his Italian last name.

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When Jonathan arrived back to the US, after more than six years abroad, his parents made an effort to make sure he felt welcomed. Non-the-less, it was still the suburbs of Edmonds, Washington in the 1976. People didn't know what to do with a family of a Caucasian husband and an Asian wife.

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Yes. If anybody is bullying you and hurts you physically, you stand up for yourself and you punch back.

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When someone else is being bullying, do not be a passive bystander, stand up for them.

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Jonathan says that the "American Dream" is all about attaining the feeling of satisfaction that comes through achieving success on your own.

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Decisiveness (or stupidity) and the ability to move fast without fretting over decisions. Commitment to a path, where you spend vast majority of energy and resources. Also, ability to work independently, without any outside support, but all of the responsibility.

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Big companies are set up to optimize individual's performance. All you have to do is to be good at one thing, and the company will support you being the best at that one thing. Startups require entrepreneurs to be extremely self sufficient and to take on all the responsibility.

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Affection is important. Whether you use words of affection or acts of kindness, your kids need to know that. In today's day and age, that's especially helpful to normalize this behavior for boys and let them know that showing emotions and affection is a good thing.

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Take risks. Have self-awareness. Stay in the growth mindset.

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Starting a media company in Seattle was not an obvious startup, but it felt right. Jonathan knew that Seattle needed a company that would champion local startup ecosystem, the cost to try it out was relatively cheap, and there was an endless stream of ways to monetize this business.

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