A Vision for a More Equitable Future: An Interview with Jonathan Sposato

Updated: Nov 4, 2020

With the YPOS 8th anniversary party approaching this weekend, we spoke with event ambassador and United Way of King County co-chair Jonathan Sposato on topics ranging from the anniversary party to his career to poverty and homelessness to his passion in investing in female founders.

Sposato is chairman and co-founder of Geekwire, and PicMonkey, as well as a serial startup entrepreneur and angel investor. Since his early days as a senior manager in Microsoft’s consumer division and as a key player on the first Xbox and Xbox games business, he has gone on to win awards for innovation and became the first person to sell two companies to Google. He recently promised all his future investments to female-founded companies—another first in the tech industry. He is the author of the bestselling book Better Together: 8 Ways Working with Women Leads to Extraordinary Products and Profits.

Clarissa Marzán: You spent over a decade at Microsoft and have since focused on founding companies like Geekwire and PicMonkey. What drew you to the startup world and what inspired you to pivot to angel investing in women-owned companies in recent years?

Jonathan Sposato: You always want to make sure that your last success was not a giant fluke and you want to prove to yourself that you can figure things out on your own and make things happen, even if the world looks vastly different than when you started in your career. At Microsoft, we were enjoying a great deal of success and it felt like we couldn’t do any wrong, whether it was in the consumer division or in Xbox (where I had a producer credit on Halo). After 12 years of that I wanted to know if I could do it 100% on my own—start from scratch, ideate a completely new product, hire my own team, and build a culture that’s different and doing so organically.

The reason I pivoted into angel investing is frankly a personal one. I was born to a single mom and we didn’t have two dimes to rub together; we were living in a crappy part of Brooklyn back in 1966-68 and she couldn’t afford to raise me, so she eventually had me live with my maternal grandparents in Hong Kong. I saw how hard she struggled, back then women were only earning 67 cents to every man’s dollar. Fast forward to 2019 and white women may be earning about 77 cents to every white man’s dollar, but if you’re an African-American woman, you’re back down to earning 61 cents, and if you’re Hispanic /Latina, you’re down to 53 cents. That’s just grossly unfair. In the tech sector, I thought that the problem started with the amount of funding that was going through women-owned companies. Just 2.7% of all investible dollars go to women-owned companies, despite the fact that over 50% of all STEM graduates from colleges and universities are women. There’s a huge disparity there, and I think social equality is coupled with economic equality.

Ahmad Corner of YPOS interviews Jonathan Sposato & Avni Patel, whose company Poppy, Jonathan invested in. (Photo Cred: United Way)

CM: You’ve been committed to supporting female founders and gender equality in the workplace.  With International Women’s Day coming up on March 8, it’s a good time to check in on what areas have been excelling and where are we still not making the grade?

JS: There’s so much more awareness about gender equity.  We’ve also accelerated on a tangential issue related to economic disparity, sexual harassment. With #MeToo and #TimesUp, people are more able to talk about these things. While sadly still prevalent, women are more heard. There are also more dollars total going to tech companies with female co-founders, whether it’s venture dollars or angel dollars. And there’s numerically a higher amount of female-founded companies year to year than in the past. There’s always been a lot, frankly, and that’s the power of women being just as innovative and creative and smart as men, even more so in certain areas.  

In sobering news, I still give a poor grade to how we handle interpersonal communications in the workplace. Culturally, we still value the louder, more assertive voice, and we’re still defining leadership in the traditional framework of conventionally masculine traits. We need to alter the way we communicate to equal the playing field for women and tilt toward qualities more traditionally defined as feminine: being collaborative, communicative, nurturing, and a good listener. Businesses would benefit if they actually did that. I would be remiss if I didn’t add that we don’t get a good grade in how the most critically important issues at the national level net out. With Brett Kavanaugh, you can’t find a more canonical example of the established male chauvinist patriarchy, if I could use these fighting words, and he’s now a Supreme Court justice. That’s where I feel like we’re nowhere near good enough.  We need to re-examine not only our processes but also how much we want to be results-driven in how we measure progress.

Become an Emerging Leader 365 at the YPOS Anniversary Party & have lunch with Jonathan Sposato. (Photo Cred: United Way)

CM: At the YPOS Anniversary Party people will have the opportunity to have lunch with you by becoming an Emerging Leader 365. What do you see as the focus of the lunch and what should they expect?

JS: They should expect to have a lot of fun! I’m not a stuffy guy, I  love getting to know new people, and I love hearing from folks younger than I about what’s on in their mind, what’s important to them, what are they worried about and  how Seattle can do a better job–where should be focused more and applying more resources, and what new trends we should looking at more closely and be concerned about. I have the utmost respect for Millennials and Gen Z, and I love hearing and learning from them. You can expect a fun conversation of mutual sharing.

CM: YP Impact will be hosting a silent auction at the YPOS Anniversary party, benefiting United Way and FareStart. Can you talk about the importance of raising funds to help support the missions of United Way and FareStart’s work? Why should people bid on the items?

JS: Rest assured that every dollar spent for United Way of King County and FareStart is spent smartly and in an operationally efficient way. Because of a generous endowment to help cover the costs of running the organization, on average 94 cents of every dollar that you give to United Way goes directly to someone in need, and FareStart is one of those programs that UWKC supports. Both organizations work hand in hand and are linked in how they break the cycle of poverty. United Way has a Streets to Home program, which helps people get off the streets and into an apartment. Complementing that is FareStart’s job training programs and the way they onboard disadvantaged folks who otherwise couldn’t get jobs, either they have a criminal record, some credit issues, are homeless–they’re given this second chance. FareStart has this category expertise to help in a high ROI way with your dollars. It’s great to have a cohort of individuals in the community help break the cycle of poverty. You can feel good about supporting both organizations, which have been around for a long time and whose missions are mutually supportive of each other.

Jonathan Sposato and wife Heather Lowenthal volunteer on MLK Day (Photo Cred: United Way)

CM: YP Impact was founded in partnership with United Way of King County’s Emerging Leaders. They both have a focus on young professionals and follow the same cycle of focusing on poverty alleviation, high school graduation, early learning and homelessness. In your view, what is the importance of these programs?   

JS: What’s most important about these programs is that they’re all adjacent issues. They all accrue to a greater whole, which is breaking the cycle of poverty. I have a nine-year-old and would love it if fifty years from now the community that we live in could be a shining example. Seattle is a city that is smart, educated, and motivated. A city where we are used to being innovative and breaking things. Why can’t we be just as innovative and socially progressive in terms of breaking the cycle of poverty and making sure no one falls through the cracks; that we treat everyone with the dignity that they deserve, and that everyone has an equal opportunity? All these issues you mentioned are not unrelated; they reflect different sides of the same issue and they’re important because they all help make our community a much better place to live.

Seattle has the largest homeless problem in the country outside of New York and Los Angeles, On a per capita basis, Seattle is actually the worst. Against the context of one of the highest-growth, most captivatingly and beautifully progressive cities in the country. There’s a staggering wealth that has been created across two generations of tech workers. You have that first generation of Microsoft people and then you have the second-generation tech giant in Amazon. The wealth creation is incredible in stark contrast to our homelessness problem. This is the number one social issue that confronts us, whether you’re a new transplant or someone born and raised here, this is what we should be trying to solve when we wake up in the morning and when we go to sleep at night.