What Fuels You on Smash Notes

#2 Jonathan Sposato

What Fuels You

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. 

Episode notes last updated on July 11, 2019 16:40

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Smash Notes summary for this episode

Who is Jonathan Sposato?

He is a serial entrepreneur, investor, and author of Better Together: 8 Ways Working with Women Leads to Extraordinary Products and Profits.

What stance did Jonathan take regarding female-led businesses?

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

What fuels Jonathan Sposato?

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

Was Jonathan always comfortable being an open book and vulnerable ?

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

What was it like to be growing up in a multi-cultural family?

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.

What was it like for Jonathan to meet a birth parent as an adult ?

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.

Does Jonathan Sposato value education ?

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.

Regarding parenting, Jonathan didn't have a father figure early on so how did he learn how to parent ?

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

How did Jonathan Sposato go from a struggling kid who got bullied to a rising star?

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.

Where did Jonathan Sposato go to college?

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.

What did Jonathan pursue at Whitman?

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.

How did Jonathan's parents' divorce influence him ?

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.

What motivated Jonathan Sposato to start a company after graduation?

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.

Where did Jonathan meet his wife Heather ?

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

How would Jonathan define the Microsoft culture during his tenure there ?

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

Is there a consistent trait Jonathan looks for in the people he surrounds himself with ?

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.

Does Jonathan believe an entrepreneur must be interested in what they are investing in ?

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

What advice would Jonathan Sposato give to his younger self?

Relax. It's all ok.