Hello and welcome to another edition of the ride. That podcast today. My guest on the show is Jonathan Sposato. Jenison is a local Seattle entrepreneur. Investor in the community Activist. He's also chairman of Geek Wire and Pick Monkey. We talk about his childhood, and it was like to be growing up in a mixed family in a time in place when it was definitely not the norm, how that shaped his life and his outlook on the future. We also talk about his interpreting your endeavors, his investments and how it will translate into a community involvement and the way he's parenting his son. Personally, I really enjoyed sitting down with Jonathan for this conversation. And I think you would, too. Without further due Jennison Sposito. Well, Johnson, thank you for coming. Yeah.

Thank you, Carol, for having me a pleasure toe sit and work with you here.

Yeah, I'm super excited to have you here on dhe thio here. Like your story about how you grew up. You know how you start your companies and how that made you as a person. And you as a parent? Yeah, you bet. And so let's quickly start with your childhood because I think it's very low. Yeah, it's a very unique childhood where you were in Asian American in the time where it was still not prevalent. Yeah, you lived in Hong Kong for a little bit, then. Your parents. Ah, you mom remarried and you can tell that story. Yeah, Yeah. I was born to

a single mother in London and actually my mom and my birth father, Ah, whom I only met for the first time a couple of years ago when I was when I turned 50 I think they met. They fell in love and they could not get married. That's sort of the families didn't allow them to get married. Because, amazingly, amongst Asian Americans at the time in the late sixties, if one person was Chinese, any other person was Korean. Oh, yeah, that's that's a big problem, right? So she she had me out of wedlock and then she went and they met in New York. And so they she went to London, where she had some family,

and then So that's where I was born. And so and then and then we came back to New York and we lived in Brooklyn Heights back at a time when Brooklyn Heights was nowhere near what it is now. I mean, I hesitate to almost say Brooklyn or Brooklyn Heights because people understand it very differently now. It's not at all. It was old people, poor people, single mothers. I mean, it was like it wasn't the ghetto per se, but there were parts that were like that, and but But it was. But it was just very working class, blue collar. And we didn't actually have two dimes to rub together, Really?

And and at some point, she couldn't afford to keep me. And so she sent me to Hong Kong Thio, where I had never been to live with my grand parents to live with my maternal grand parents. And that was a fantastic experience. You know, I think my mother still feels guilty like, Oh, I'm sorry I sent you away. I'm like, you know, actually, that was great, because I got to know my grandparent's. I got to know my my auntie. They get my youngest aunt who was still living at home as a teenager at that time and just had a great upbringing on, Learned a lot and I actually think a lot of it sort of defined who I later became. So

it's interesting because you had this piece and let me quote that real quick when you wrote it on your ah lengthen and I'm gonna link to that old podcast. It says it's 2 a.m. I'm eight and I'm alone. It has been six years since my mom placed me into a yellow cab in Brooklyn into the arms of a Chinese grandmother I'd never met. And I was whisked away to a country where everybody speaks a language I do not understand, you know, and continues. So by that tone it feels like it is fairly dramatic experience.

You know, it's funny. It was, Ah, that yet that was, I think, um, excerpted from my book Better together Eight ways. Working with women leads to extraordinary products and profits, which is really about It's kind of a tricky title better together. But it's really about gender. It's really about how we can do better and in the business ecosystem. Thio have more women, be in positions of senior leadership and see NBC EOS and have really truly unequal seat at the table and do away with the institutional biases that that have caused that have held women back and any underrepresented minority back. So I felt that it was important, and a publisher and my editor and I thought that it was really important that people understood that I was coming from a place of less than myself because optically and this is a problem, like,

you know, we're all very quick to judge based on the way that someone might occur. So, you know, there's nothing more insufferable than than Thio hear about gender equality from a tech entrepreneur, a male tech entrepreneur, right? And so So I had to very quickly in the first chapter talk about my past and to make sure that that I conveyed that that was that was a pretty traumatic thing. Although although I would say that for years I didn't really focus on it. And it wasn't a source of trauma for me, at least not that I understand. Maybe someone maybe my good friend, who was that? Andy Sack was just great about talking about the value of understanding your past on Dhe, how it's a creative too who you are and maybe he would say, Oh,

no, no, no. That that's something that clearly has some impact on you. And so, But anyway, I look forward to learning more about that. But But it's not something that I thought about at all growing up until more recently so

interesting, because it feels like in hindsight, a lot of things you do are very much influenced by the early years, right? And maybe that's what Maybe that's why the book was written that the way it is. But it does feel like you have the knowledge that enables you to in fact, comment on issues like inequality or homelessness and so forth because of your early experience. Yeah, I

think so. I Yeah, I think so. Is that what you mean? Yeah. Yeah, I think what is true are common for better for worse is that I can always see it from the point of view of somebody who is less advantaged. And I joke, you know, I'll just be honest. I mostly feel like and I've joked with people who I work with all the time that these days I or I have always felt really growing up that I was like the nick care away to somebody else's Jay Gatsby. If that makes sense, if you understand sort of what it's like to be the outsider. Uh, you know, in The Great Gatsby, I think I think I think Nick Nick was the poor kid from the wrong side of the tracks that somehow finds himself included in,

You know, the cool kids and and and he's always kind of reflecting and observing and understanding. Like what? You know what? How are these people behaving and what drives them? And and, uh and so I find that stuff interesting. And there's this insider outsider mentality where if you've been more lucky than good in your life like I have, I've certainly been more lucky than good. Whatever successes, conventional definitions of success that you can point out that I've been a part of, I can assure you luck was a huge component of it. And so when you've had some luck over time, you find yourself, ah, part of some world that you didn't help to create,

that you never thought you never dreamed when you were that seven or eight year old living in Hong Kong and and in a kind of these sort of very humble, humble two bedroom apartment in a you know, a very packed and danced apartment building that you would never dream that someday you would be in those situations. Number one. I'm grateful, but number two you keep on outsider's perspective, I think, almost defensively you think that that's a way to maintain some grounding, to not take things for granted and to always appreciate how far you can go, the miracle of possibility for others and what can happen if you allow room a seat at the table for for others and that I still believe that this is the greatest country in terms of social mobility and entrepreneurship. So if you if I believe those things, which, as the chairman of Key Choir, I I absolutely believe, Ah, and as a serial entrepreneur, I believe if you believe in those things, you have to also maintain your grounding. I hope that makes sense.

It does, and you've written about this before and how you basically keep it perspective, right? Regardless of the wealth and the remember reading somewhere about the Microsoft Days, where everybody became a millionaire, you were saying that statistically like 90% of lottery winners and broken three years. And you've seen that happen, too? Millionaires coming out off the company's,

too. So I may not say that 90% of Microsoft millionaires, but the general statistic about a lottery winners was that it's like it's over 90% that they become broke in in a very short amount of time, whether it's in two or three years or something like that. But But, yeah, there were a lot that we didn't know what we nobody taught if they taught us to be great engineers and program managers and marketers and strategists and technologists. But very few of us had any kind of mentoring on How do you preserve your wealth or or invested and to do right by it or be or be philanthropic with it at that time early on early on? I think it's a different cohort or a more mature ah group of folks now that are there or have stay or they have themselves evolved and grown into that. But yeah, I'm sorry to cut

you off. You know, it's great question, but we'll talk about Michael something a little bit. Can you tell me more about what it was like, though, to be a kid who just got pulled out of America and moved to Hong Kong. You don't speak the language. Grandparent's. You met them three days ago. Yeah. What was it like? Do you remember?

Yeah. Um, I remember very clearly my first e night and days in Hong Kong. I didn't understand what being jetlagged was, and I couldn't fall asleep. And I remember just laying there looking. I slept on a cot just looking around this dark apartment, and it was hot and everyone was sleeping and I couldn't sleep in her. I have those memories. I was definitely a stranger in a strange land. I didn't speak Chinese, which in Hong Kong is was and still is Cantonese. And so I had to learn how to speak Cantonese very quickly. I don't have a very accurate memory of how long it took for me to learn it, but I did become fluent in it and went to school and everything and didn't feel as though I was at a deficit in any way. I did feel different from the other kids. I knew that I had a British passport.

I knew that. You know, my friends knew that I was from the from Barry's, born in London and lived in the States. I went to Ah, really great school, which I visited actually a couple of years ago. For the first time, it's called Rosary Hill Academy. And it was great, you know, with the uniforms and the blazer and a tie and all that stuff. And, uh, and it was run by Spanish nuns. S O.

I joke that I was the only Chinese kid born in London who went to ah school in Hong Kong, run by Spanish nuns s. So it was a lot of fun for me. I really have nothing but fond memories of my childhood in Hong Kong. I love my grand parents and my Aunt Marianne and I learned so much, and I think it's it's it was for me healthy to be a street kid. I think later when I would come back to the United States, I was in the suburbs of Edmonds Washington, and that was a huge culture shock for me. But tow have both to grow up, sort of appreciating both. Okay, so here's what you get when you live in one of the biggest cities in the world. Hong Kong. And here's how you, you know,

navigate the city on your own. And back then, I think people weren't particularly uptight about, like, you know, if you're, you know, 789 years old, you can't go anywhere alone. I mean, I could just go down the street and by myself a snack or comic books and come back to the apartment. You know, that was, like, Okay, I think it's good to have that. And then at the same time, it's good to also appreciate the good and bad of being in the suburbs. Right? And then you can hopefully have that choice for your own family and kids.

I'll make a mental note to talk about this about you, you know? Yeah. And

am I going to say I'm sorry? Yeah. Let me know if you want me to be more succinct.

ID? No, it's ah. If in fact, if you want to go in more detail, please D'oh! Because I think it's really interesting. Do your, uh How many years did you end up spending in Hong Kong with you?

It was between the age age of ages of three and nine and 1/2. I think so. That's six and 1/2 years.

Did you get to see a mama told during? That's

No, Not at all. I didn't see her at all. In fact, I know I didn't know who she was. Really? When I was in Hong Kong, I knew there was a mom. I knew that she was in New York. Uh, and then she would send back money. Anna and the Christmas. Like, I remember a big red fire engine that I would get, which I wish that I still had, actually, you know, things like that.

Yeah. So for six years, you grew up knowing you had a mom start kind of having a memory of leaving your mom, but your brother But your grandparents were basically a pair. They were my parents. Yeah. Uh, yeah. How did you wreck reconnect back with your mom when you're finally matter at nine. Something? Yeah.

Yeah, it was what she was. Very I mean, I I loved her and, you know, it was, but it was She was a stranger to me when I was nine and 1/2 10 came back. I remember my the man that she married a really lovely man. Still, I'm in contact with him. Dawn Sposato. That's how I have an Italian last name, right, Because he legally adopted me. And I honor him by keeping his last name and all that. He stuck out his hand, picked me up at the airport in Vancouver and said,

Welcome, son. And I thought that was great. My mother was more shy, praying more a little more introverted, and I got to know her more slowly over time. But I remember the very first night when she was showing me in my bedroom and and, ah, kind of how it was set up so beautifully. And and, um then there was like a big Snoopy. Well, big to me. But probably at the time, you know, actually,

like quite small, Probably like, you know, 14 inches tall or something like that. But like a Snoopy stuffed animal. Ah, and it was on my bed and I recognized that Snoopy from our apartment in Brooklyn, and so that was a nice touch. And I still have that which eyes kind of funny to me, but I'm not actually that nostalgic about my childhood. You go into sleep, I still snuggle that. Yes. Uh, no, it's It's probably in a sort of cardboard box somewhere.

So I hope it's not throwing throwing out by now. But but But I remember that she was really great. And but, you know, I'll be candid that the things that I struggled with them moving forward are in Edmonds, Washington in 1976. You know, people didn't know what to do with a family where there was a Caucasian husband and an Asian wife, and so they would always ask like it was your mom a war bride. Was she a war bride issue from Vietnam? Are you Vietnamese? And that bothered me and yeah, you know, it was that was hard. And I was, and at some point I stopped.

I just decided to not over function anymore to explain to people what it waas and so I would just say, Yeah, you know, it's Yeah, whatever. Just I just let them assume what they want to do, assume and because it was just too hard to explain it. Well, no, he's actually, you know, he's a you know, And no, we're not Vietnamese and here's what happened. It was just too much of a long story.

See, I think that Israel is That's very important because to an average, why did Racism doesn't exist And sexism doesn't exist either, right? Because they've never experienced it. And ah, but it clearly does. In fact, people were so ignorant that it's comical.

Yeah, they can be. Yeah, there was all kinds of stuff. I mean, growing up was I actually thought that was really good dust both the good and bad of being out in the suburbs of Edmonds, Washington. If you're the only person of color as a kid growing up the experiences that you end up having really galvanized you, right And I know you know in this day and age I'll go on record to say that in the context of this day and age, where at schools with our kids, because this is ultimately about being a parent, right? If our kid gets picked on, you know, we don't condone fighting or anything like that. But I will go on record to say that I have told my 10 year old boy, especially when he was younger,

that if anybody hurts you physically, you stand up for yourself and you you punch back Because because number wonder Doctor, they're not gonna hurt each other there. Dear. Look, they're not. They're flexible. They're flexible. Don't grow a limb back. No, But in all seriousness, it's it's Maur This concept of if you learn If you learned that bullies can very quickly become a shrinking violet if you hit back, I think that's a powerful lesson. And that's a lesson that benefits you moving forward. And I think that if you if you learn to then sort of apply your power judiciously and fairly. I just think that those are good lessons.

Let's talk more

about this because Indy, sure, all kinds of people are gonna be mad at me now explore administrators. And now we're gonna get kicked out of our school

anyway, Uh, right. You're not behaving like the right type of parent they were looking for. When yeah, which schooling in the fact that they select parents not actually Children. And by the way,

to be clear, I'm saying, if the other kids, if there's a pattern of bullying, the other kid is like picking on your kid. And then And then the other kid hits first. Yeah, as a father. And I would say this to a daughter or a son. You have my permission to hit back?

Yeah, I've implied that to my four year old already. So I I'm with you on this, but it's interesting because we grew up in the bubble. I also grew up in this city in ST Petersburg, Russia. And so it was a very different love to know more. Yeah, it was a very different experience to, you know, being in suburbs right now. My kids are growing up just for the record. Jonathan Dogs, they're running around and they're a door or they bothering. You know, they're a door.

Can you hear the little trip trapping on the

floor? It's great. It's audience live audience. So what do you think of this environment with creative for ourselves and our kids? The suburbs? A great They're safe ish, you know. But that's boring, and it goes from the way we live to exactly the way because I've also experienced bullying in school. And that's why no, it's fine. I in fact, I'm nodding because I think it was valuable experience because if you've never experienced that, you just assume that everybody's happy go lucky. You know, world is nice

and danger and everybody's just gonna give you whatever you want. And they're everyone's gonna like you. You just show up and great things happen. No, if you've experienced bullying or you've been a person who's made to feel less Stan, maybe only person of color somewhere whatever or or or convert. You know, I've heard stories where if someone is the only white person in a in a community of color and if you've ever been experienced being a minority and you've been picked on for that, I think it you lose very quickly this notion that you can just show up in your charming self and people give you things.

But at the same time, I think you learn that, actually, bullies have no power. Yeah, visit. Physical strength is like the last resort. But when I got there, they already lost. Yeah, right. So how do we give the star of kids that dynamic? I mean, you don't really want your kids to get hurt like you kind of don't want them to experience bowling. But at the same time, you want them to experience the dynamic range of life. Yeah, you know, not now that you're so honest in years old. How have you been approaching this?

Well, I would say, you know, there's there's good and bad in a sense, it nowadays. I think there's so much that we know about social emotional learning and how they're teaching kids to recognize when someone is being a bully and to also understand that bullying is not. It is hurtful. I think that's really good. But having said Dad, it does happen still, and I and I think again my approach is to make it okay for him to stand up for himself and and to stand up for others just to be clear, to stand up for others. I think that's an important thing. Toe activate in a young person like like that I think are most powerful. Lessons are around when he comes home and talks about Hey, you know, everybody was sort of,

you know so and so was being sort of stupid or silly. And then we were all kind of making fun of her. And I'm like, uh wait a minute. Let's tell me more about that. Why would she do that? Was that deserve that? And why were you all jumping on? You know, on her And what What? What did you realize? That it's It's many against one. And that's inherently probably unfair. And And how would she feel being on the receiving end of that? So do you feel like that you needed to join that? Or might you take a step back and think,

Oh, wait a minute. Now I think where we could be wrong and how we're looking at it, she didn't intend to you no disrespect us. And maybe we don't all need to jump her jump on her case. And so anyway, so I do. Hopefully that answers your question. I think I hadn't being very realigned. Candid about those issues with your 10 year old is

important. I love that you're saying this because I think in general, parents love to preserve the kid's childhood, and I'll find the segment and added to the podcast. But I remember people talking specifically. It was, I think, either a school instructor, somebody basically with a lot of experience, working with Children how she was saying that you can teach kids a lot of things, adult things. You just don't have to name them the same things. You if you bring the subject's down to their level. They're actually very curious. Yeah, that's right. Oh,

that's what it was. It was a tad talk entitled How To Teach Your Kids About Consent. She was like, Usually when you say that people go, Whoa! You know, that's sexual top. I

got some funny ones that they're on that.

But but the point there was consent is not really about sex. It's about a power dynamic relationship. Person's rights. There's a lot that you can talk about it with a six year old and actually explained the whole subject as long as you talk about where they fit in the society and their friends

and so forth. Yeah, yeah, that's right. Yep, I I agree wholeheartedly. I think that there is a way to talk to Children both candidly, but but in a way that that that makes sense to them that you can kind of remove the something's Yeah, consent is one of them. Or, you know, you're doing that thing that we all have this where we're listening to NPR in the morning driving our kids to school and then, you know, you can't You can't go around switching the station every time there's news about Donald Trump sexually harassing, you know, I don't know how many it is like 32 women or something like that and, you know,

grabbing things. Your kid in the back seat, like, what does that mean? You know, then attempted to explain it in terms of consent or privacy, or your body is yours, And you have to you know, somebody else has to have put you can't touch somebody without their permission. I think that that's just that's one way of of making that issue clear.

Yeah, we got a little bit sidetracked. Yeah. Sorry about that. No, it's great. But we were talking about you in Hong Kong, and eventually you came back, sort of started rolling with your family, and then I found that from what I've read, I found your relationship with your mom sort of interesting because, you know, fast forward a little bit when you were in college and you called her to ask whether she'd like to stay over for a graduation. And that's when she decided to break news that your parents were getting divorced and that they probably weren't coming to your graduation. Correct. Was that kind of your childhood, because that's a very emotionless experience.

It just feels very cold. But you love your mom. So, like, how did you bounce that growing

up? That's a really astute observation, although I would ah, for just the benefit of the listeners. I certainly would not define my mother as emotionless. She's probably quite the opposite, but that moment was sort of in some ways, a defining moment because it lit a fire under me, too. In some ways catalyze my ambition. If you want to call it that, um, when you realize that you're not gonna be able to come home after you graduate, that was really the moment wasn't so much that they couldn't come up to see me graduate. Maybe that was okay and my mom made it on her own. I think without my dad, my dad at that point had already moved out and moved to Foster City in California.

So he wasn't gonna come up and you know what? Bookmark that there's sort of a lesson there you'd really never know. When is the last time you'll see someone like When was the last opportunity that you could have had to say goodbye to someone for a while until after the fact? Right? Ah, and that's true. When our friends die, you're like, Oh, you know, I hadn't seen him in a few months and I guess the last time we had coffee was that was it. And I never had a chance to tell him that I loved him, You know, that kind of thing. So with my dad, I felt that you and of course,

I reconnected with him later. But But it was more that I couldn't come home because she said that, you know, don't bother coming home when you pack up your stuff, you know, and drive home. Don't come home because we're selling a house. So you you're kind of on your own here. And so I literally hung up the phone. It was on a Friday or Thursday, and I got in my car, drove home, interviewed with my old boss. Ah, it really asked him like, you know,

Hey, when you said that I could always come back and work here. Did you mean it? Yeah, you know, But I still had toe go and get that taken care of and talk with some other people interview with some other people so that they didn't think that I was not up to snuff. And and and so, God, you know, shook hands on a verbal job offer, drove back Saturday or Sunday, packed up my stuff. Oh, and I took fine. Finals week was I hadn't taken my finals yet, then took my finals and graduated.

And so I had a job lined up before I took my finals, which was good, and then I never really looked back. I always thought that that was it was sort of my path to move forward to make something of myself toe toe, carve out my place in the world, and I have to admit that I reflexively kind of bristle at, you know, if someone was to say I remember a good friend saying, You know what you're gonna look when Holden is graduating from college. Aren't you gonna help him with his first get his first job or and then help him with his, you know, first and last month's rent on his first apartment. And then later, when he gets married, When once you start a family, aren't you gonna help him with the down payment on this house?

And I understand that maybe the world is different than it was in 1989 and that it's harder for young people to do those things. But reflexively, I sort of bristle at that stuff. I'm like, No, I'm not gonna do that. I'm not gonna deny him the opportunity at the American dream and the satisfaction of earning all of that through your own efforts. No disrespect to anybody who got to live at home after they graduated. You know, I got to live with their parents for a few years, no respect to anybody that had their parents help him get a job or, you know, first and last month's ran or when he bought a house, you know, Mom and Dad gifted them the down payment. I don't disrespect those folks at all.

In fact, I feel like That's lovely. That's wonderful. But for my child, I want him to feel like yeah, man. Fucking a. I did that from us. You're smiling like I'm not sure if you're like Oh, my God, this guy's off his rocker or ah,

no, I think it's great, because I can I can feel both, Like, you know, from what you were saying, when when I graduated, I moved out to Seattle because I wanted to start a startup and I didn't want to go, you know, work. It's Starbucks so that I could like. So I guess you're young enough

that Starbucks with an option for you when you graduated.

Yeah, it just seems silly to me to go get somewhere a temporary job into waste time where I could learn that the much faster pace doing something that I really wanted to D'oh that on one hand. On the other hand, you know, parents contributing to the down payment. I can also relate to that. Yeah,

and so did that started me. Nobody's respect. It's man again. You're younger. You're like a younger generation. It's houses are expensive.

Yo. Yeah, so but no, uh, curious. Giving your experience investing in entrepreneurs and doing your own companies. Do you feel this is one of the defining factors for entrepreneurs? The ability to actually move fast and make these otherwise hard decisions very quickly and the very unassumingly in the sense. Because finals week, most people are cramming, you know, getting really anxious about the testing, taking. They don't get cold from their mom saying There's no house, we're divorced. I'm not coming, you know. And then you just figured it out and it was just another day. Um, do you think that's actually an important aspect? That

yes, I think so. I think it's a kind of a cluster of attributes that might include maybe, as you said, decisiveness and then or stupidity on, and also this quality of moving fast and not wasting time. It's like once you've made a decision and that's moved that you don't need toe fret over it for weeks and you're some very interesting thinking around that you know that that old in fact, one of the most influential books that I read when I was in my early twenties was the one minute manager, which I've kind of forgotten the details. But there's some understand new updates to that school of thought and and there is also similar thinking about the one minute decision or or how you can make decisions quickly and or give yourself like a day to make that decision and and then whatever it is that you decide, you just commit to that and move on. And so you kind of limit the amount of analysis paralysis that we might all naturally are pretty supposed toe have. And I think that's the very interesting. Thoughts may not work for everybody, but but I do think that ah kee a critical set of factors for entrepreneurial success, our decisiveness moving fast commitment to a path like you don't always. Sometimes it's good to hedge your bets,

but you know, you generally don't you commit and and maybe there's an escape route or or a way that you're hedging. But you're spending the vast majority of your energy, and resource is on the committed path. So I never assume that my parents would somehow magically like my mom would get her apartment situation figured out once she sold the house. And then I could, you know, live in her spare bedrooms. I never, never, never assumed that, and it was good, right? Because actually, as a matter of fact, I think it was within my first couple of paychecks that my parents both separately now that they're divorced,

needed my fan of financial support. So I helped them out, and that were those were some powerful lessons, too. So But, you know, either you can't rely on, you know Oh, self sufficiency, I think. Is that third element were you? The buck really stops with you. You don't have some other giant HR division in another building helping you hire people. You don't have another marketing division or product support division, you know, and I've been there.

I've been inside the belly of the beast, so to speak. Bennet. I was at Microsoft for 12 years. I was at Google twice. You have. When you're at a big company, it is completely set up optimized to let you do you. You just If you're a product manager, you just think up of cool new shit. Cool new features to create. That would be a creative to the company's success. And they don't need you to also worry about how to figure out payroll. How to deduct this new city tax out of somebody's, you know, Ah,

paycheck. Because the city of Seattle change their loss. Eso eso eso. As an entrepreneur, you really have to understand that the buck stops with you and you have to be incredibly self sufficient. So thes air, all cliche things that I'm sure you're audience, you know, has heard many times before from smarter people that I Oh,

I think you're pretty smart. And actually, I do want to know about, you know, you think you downplay the fact that you're pretty smart. Sounds like you've always done pretty well in school because that was the Asian household where, you know, a minus was

not a thing. No, a minuses. You might as well gotten a d. This is. You learn to be tricky. You learn to work that you learned it? No, I was always a hack man. I am was not? No. I mean, I was always on the receiving end of my mother, telling me like, Oh, you should see my girlfriend. Millie's daughters.

They both got into Brown. Oh, actually, one got into Harvard, but said no because she wanted to be a ground with her sister. You know, he'd be like that. I'm like, Oh, okay. Thanks, Mom.

See what I mean is like, Well, my, um my wife is Asian, so I can kind of fuel. It'll actually didn't know that I have better. Yes, way could have a whole other podcast. Exactly. Just asian. Uh, I'll bring my wife. What can we do that? Can we have that podcast, I think would be lovely. Yeah. It might get a 1,000,000 downloads in the first date.

Absolutely. What? Yeah, yeah, but that's what I was implying what I said about, you know, like of emotion and delivering that message because I think a lot of Asian parents don't even think about that as needing emotion, right? Like some things that just straightforward facts. This is what it is. You go, do you, Which is interesting because I think it's shaped you to be who you are. And is that how you're gonna be, Ah, treating your son? Or are you trying to be more warm and fuzzy,

more warm and fuzzy with him? I think it's important to show that affection is important, Verbal, Whatever your love languages, I think I'm doing them all with him, right? Whether it's acts of kindness or words of affection or physical affection and maybe not the gifts part physics, you know, actual gifts. Because I think that kids don't need to be spoiled with, you know, needless stuff. So But I tell him all the time that I love him. Probably a couple of times daily, if we're just If there's a low or a dull moment, if I'm feeling it, we're cuddling.

I say, Hey, buddy, I love you, you know, no matter what, and he and he will come back with something sincere almost always. Sometimes you'll tell me to shut up or we're not sure, Dad. Okay, enough. But most of times like, I love you too, Dad. And that's Ah and that I think, to normalize,

especially men or boys, to grow up to be the kind of men who can say things like that. It's not a bad thing. Wait. So So I would say that I'm not unemotional or I try to express emotion and a show of range of human expression with him to model the right behavior. You know, the key thing is also model behavior, where you always come back to a good place if you can always say whether it's too another loved one, like my wife or to my mother. Whatever. After a heated argument or you're not talking for a couple of hours, you say, Hey, I'm sorry about that. And even though we may still disagree, I love you anyway,

right? And so now my 10 year old, he's He's hilarious about that. Like sometimes he'll have a tantrum stomp off into his room, slammed the door And then, like, now, five minutes later goes Dad, I love you anyway. Slam. So I think that's hilarious. Always remember that.

That sounds pretty cute. I think people can find a lot of information about you and your startups, and, you know, that has been talked about. Well, you did pretty well. Like you said, You're

more lucky than good,

my friend. Yeah, but you're still the only person to have sold to companies to Google. I mean, that's pretty tricky in a row. Yeah, Yeah. Oh, yeah. Um, while had been raised by Spanish nuns. That's right. Yep. There you go. But everything you know about entrepreneurship and what you learn in the Microsoft in 12 years, plus your startups, plus the people you've invested in, What do you How do you take that and influence your own life. Your kids and people around us? Yeah, with that knowledge.

Yeah, Um, a couple of things. One is three importance of taking risk and to be so. Of course, if you were to say, it's almost like I heard of it, that's saying like if you ask someone if they're you asked 100 people Hey, are you racist? You know, there were 100 people would say, No, I'm not racist. Why does racism exists? So things like the like the following things about entrepreneurship, like taking risk, recognizing value,

add ideas or hiring really well all those critical success factors to entrepreneurship in building great companies. If you were to ask people, would you agree? What would you agree with those things? They would all 100 people would say, Yeah, those are all the things that we do or want to do. But I think what happens What prevents some people from doing those things is that they lack a certain self awareness. So I think you start there. So I try to tell Holden Hey, have self awareness. This is where maybe you're getting into a pattern. This is where maybe you're letting your anxiety get the better of you. Like you're saying No, you don't want to go to this coding camp because you don't know anybody there right now. Remember how last week you also did the same thing?

But then when we went, you loved it. Like after the first day. You're like, Oh, my gosh is the best camp ever. So it's possible. Would you agree that that could happen again? And so So things like that. Just being self aware is a great place to start. Then I think things like taking risk and and not being afraid to try new things. You know, they're the other framework that sometimes I've heard people put it in is whether you're in a growth mindset or in a fixed mindset. And it is incredibly important to entrepreneur, successful entrepreneurs to be in a growth mindset. Starting geek wire with John and tied,

I believe, was the result of being in a growth all of us being in a growth mindset with me in particular, I had no, I was not a journalist. I'm still manager. Was I had nothing to do with that kind of a media play a media business. I knew that I had been on the receiving end of especially John Cooks interviews, and I knew what that was like. I also knew that what the what? The ecosystem with the Pacific Northwest tech ecosystem, which was at the year, If you rewind the clock back 10 years, Amazon was not as big a deal. Microsoft was kind of Maurin a law. Ah, Facebook had not opened an office here yet.

Google's office was incredibly small here, and there weren't as many companies. And it wasn't as much money going into starting startups. If you go back to that time, you had to really make that bet. Take that risk. You know what? We have a shot. This is really division. We have a shot at creating the Seattle Tech ecosystem and a community around it. Tohave it be just as respected and vibrant and dynamic and interesting as the Bay Area. Everybody wants to talk about the Bay Area and how amazing Silicon Valley is and has been, and it is amazing. But we can be that to be even better in many ways, that culturally were better because of these values that are more endemic to the Northwest. So taking that risk is a great example of being in a growth mindset because it's like,

Well, I'm not gonna do another consumer Internet or a sass business like I had been doing doesn't have to be another photos company, although I did that too, you know, because I didn't feel like I was done with photos. Let's do a media company. Let's do news. How about that? As it turns out, uh, it's gonna joke. John and Todd covered your ears. You know, reporters are a lot cheaper than engineers. Yeah, and I've told those guys down already already to know this,

but But you know, the cost structure of how you can yield a lot of output and page views. And you know what? Whatever subscribers downloads, whatever it is that that is a creative to your business of success, you can. The ratio of the cost per employee is radically different then in consumer SAS software development. So that was interesting to me. Other things interesting to me were the fact that there were nine ways to Sunday to monetize right, You weren't locked into necessarily assassin model. There was a sponsorship model. There was an events model. There's a membership model. There is, um, just an advertising model of all else fails.

You can just, you know, have your page views be monetize. Herbal. So So So those that was interesting was the vast degrees of freedom on monetization. The last thing that I thought of which is just a bonus. Or, you know, the thing that I didn't think of and it just became his bonus was really our place in the community and how it's become a convening platform to bring all kinds of people together. You know, whether it's it's elected officials, mixing and networking with the area's top CEOs or the top scientific researchers or academics or gamers or sort of or other media folks. That is just a bonus of that and that. And that's by the way, Like, you know,

the credit goes to John and Todd for having if they're really the operators and builders and workers, the people doing doing things, working to provide this output in hiring great people and and thinking through processes, you know, I just kind of coming on occasion and try not to cause too much trouble.

So it's been almost 10 years of geek wires. Yes,

that's why it's about 10. Yeah, it's the age of our Children. We were all our wives were pregnant or actually holding had already been born. I think Jack James, John's son, had already been born just a few months holding with six months. James was three months and then Todd's wife might have been pregnant or something like that.

We can reference with John's podcast. Yeah, we'd reference back. My memory's foggy. Yeah, yeah. Do you think you guys have been overall more successful? Ah, in the last 10 years with a goal of geek wire. And like you said, the idea was to enabled second premiership in Seattle. Bill, that community or ah, I mean, you obviously have been successful, but you know what has worked and what didn't

What do you say? Yeah, yeah, you bet. Happy to talk about that So largely We've been successful in some ways and in some ways not so I think that we did succeed at the things that I talked about prior, Like being kind of a convening platform we've built, you know, way sort of coalesce. The community. And to be clear, the community would have if market forces were left alone. The community would have called us in some other way, I'm sure, but I think we way enabled a slightly different version of it. And where I would like to think of more interesting and dynamic version of it, where it was also more inclusive prior to geek wire, all of the industry events in the tech industry here in Seattle,

where, AH, lot of stuffed shirts, they were sort of boring events at hotel lobbies where, where it's a lot of, you know, old guys in suits, bad suits, nothing wrong with the good guys in bad suits per se. But if that's all you have, that isn't very fun for a budding say woman of color younger who was trying to be an entrepreneur and pursue her version of the American dream, right? So So I think that we've succeeded there. We've succeeded in Jack the core function of the core value of being a nationally recognized technology news, you know, business news site that is rooted in the Pacific Northwest.

You know, I think that gives us a different flavor than TechCrunch are wired, which you know on a tech mean leaderboard. We're right up there with right? So that's I'm very proud of that. So we succeeded. In that way, I would say the ways that we have not succeeded and I know that I own it. Ah Maur than John and Todd are really on the business side of maximizing our potential. There are ways in which we need to be Maur or can be much more thoughtful about customer lifetime value. What causes people to come back? What causes us to lose them and they don't wanna look at us anymore or come to our events? Is there more value we can imbue in our membership programs that would make it even more value? Add Are there better partnerships we can foster? And strategically, what are the new areas of growth that that would not growed for growth sake,

but where we could get a one plus one equals three, right? So the Portland area is a really great example of that where we had am a desk, a bureau chief down there Ah, for a while and and I think that that didn't really work out for us a CZ Well, is that I think that it was fine while it lasted. But then we went our separate ways and and but But that was a good example of where one plus one equals three, right? Portland is kind of synergistic with Seattle. Are there other? Is Austin Another one is L A Another one is New York. Another one is even Hong Kong overseas, right? So I think getting past hour operational and procedural hurdles are growth and scale challenges are all things that, quite frankly, I could be much more of a hard ass on.

But as I was, I think, describing over a cup of coffee with you before we actually started a podcast. You know, there was a period of a number of years. I think at least 45 years were I did necessarily take my eye off the ball a little bit with geek wire as my other company pick Monkey really started to grow and had those very same business challenges. And I, the businesses needed me a little bit Maur and spent more time on pick monkey and and kind of changed the allocation of number of days of pick monkey versus geek wire and and pick monkey, you know, got outside shareholders and they were sort of, you know, I think scratching their heads like a wallet. What is this other geek wire thing? And and so So I am taking my eyes off of the ball a little bit Icky choir, which which, by the way,

John and Todd, being amazing business partners enabled me to do so right? It was okay, because I'm, like, okay to businesses in good hands. I no longer have to sign off on every higher Or, you know, back in the old days, you know, I interviewed every employee and and and we would meet and huddle on, like if we did have to let someone go, we would all three talk about that and kind of look each other in the eye to make sure that we were on the same page. Those things started that toe happen with less and less frequency. They were less necessary because they were making the right calls. So that enabled me to to step back a little bit from geek wire, which which may change now that I have more time from away from the other things. So So I think that we've won on some things and we still have a lot more headroom to grow and do other things.

So requires doing great. You could definitely expand, and I think you should totally expand to Hong Kong and other places because it would give Seattle readers window into other places. You're

having a heart attack if they hear this, what we're spending Hong Kong. Hong Kong was just one example of just kind of ah ah, wacky example of where I think that a while we already have a national presence. It would be interesting to try something international.

It would be really interesting. And all you need is like you said, reporters are cheaper than engineers, so you can hire one guy and places like Hong Kong, Taiwan and other places in Asia or this plenty people who write beautiful English, right? So you don't even have to worry about that. But you're also, um you did the photo cos you get a gaming company, G choir, among other things. But you're also out spoken about other issues like normal people's issues, like homelessness. Or, you know, the fact that women are not being paid as much as man. Oh,

why? Because I mean, it's kind of tongue. And she questioned, I guess because it's just a so many wealthy people who don't care at least publicly don't seem to invest in those areas. And you're very public about it, about actually trying to create a community around you that will survive and strive right like, Is that your upbringing? Is that just Johnson being the good guy who wants the world to be a better place?

Oh, no, no, no, what it is. I think it's more upbringing and the influence of others and good people in our community who have been great role models. And there are many because I think that our actions are even our values. To some extent, you know, probably someone like Sam Harris will talk about how in our thoughts are the result of something else. So I don't know if you pull on that thread really far. I don't know how much any of us could really credit ourselves or pat ourselves on the back for being a good person or whatever. I think it were all sort of the product of our own of upbringing in context and things like that and and influences. And so I would say that I'm the same and I feel like there's so much more work to do. And as it relates to being a parent, I know one thing that I think about a lot is you have to model the right behavior for your child. You cannot expect your son or daughter to do the right things.

If you yourself are not doing those things, I think they learn much more by observing what you do than being told. So I think that is probably a powerful driver of my philanthropy, and I don't even have it exactly right either. By the way, I think I fumbled around with Oh, I'm going to say yes to this. I'm gonna say yes to that. And over time, you're like, well, in terms of philanthropic things, these are things that are maybe they're not really that important versus this other philanthropic cause, which affects all of us in King County. Or there's a way to very efficiently move the needle with thousands of people, versus just a few who may be already there anyway who are OK at the end of the day.

So that's how I focused on homelessness and also gender as my two top issues. I mean, nobody needs to be told that we have a problem with homelessness in King County, and there's been a lot of cynicism around that stuff. There's been a lot of you know, Seattle was dying, and I say, Heck, no, Seattle's not dying. It's really thriving as a matter of fact. And because we're thriving. A certain segment of Seattle is sick. Has the cold or the flu, right? That's what I say,

but we're not. Seattle in general is not dying, so we need to not be cynical. We need to not blame the victim. We need to understand, cause ality and lean into it and face the music and not be defensive. We need toa understand that when the city does things that seem counterintuitive but based on research, say, for example, safe injection sites right that that's coming from a place of where they have the data that tells them that that's the way toe on ramp. The drug addicted to health service is that that has a very high conversion rate, right and so it seems counterintuitive. What wise public money being spent on safe injection sites. Think it through, man. Before you react emotionally and be like,

Oh, what? We're condoning drug use. And that's the freakin problem, right? We're not tough enough on criminals. And by the way, this there's this myth that all the homeless, especially from this you know, co Moh new special Seattle is dying. There's this myth that the homeless, they're all drug addicts just say meth myth go. Oh, that's a math. Yeah, I'm kidding. Yeah. Are you referencing

Andrew Gang? No, Uh, just the fact that there is, ah, notion that all the homeless drug addicts meth Oh, man, I'm sorry. I misunderstood. Yeah. Yeah.

So only as it turns out, only 23 or 26%. I'm off by just a couple of a little bit there on Lee. That percentage is addicted to things like our narcotics didn't general segment of drugs that's considered our count ka ticks. And then an over an overlapping and super set. A broader percentage. If you add in alcoholism, then that's, like, 40% of the total. So you take the 12,000 people who are homeless in King County every night, right? What is 60% of 12,000? That's like, you know, almost 7000 people there are 7000 people were homeless who live in their cars and your RVs who are not on drugs, right?

And maybe they lost their apartment. They maybe I lost your job. You got sick. Maybe they got divorced. A couple, usually a couple of factors, and a lot of them even have jobs if they go to and they're secretly homeless, right, the shower at work or at their school anyway, they deserve our help. And even the folks who are using drugs, they deserve our help, too. But but so I think it's wrong to get super cynical about it and have a combative attitude and be negative about it.

And I gotta admit, I might be one of the cynical people, but also listening to you. It's, um it's great to put things in perspective because you just said 12,000 homeless people, right? And I think about it. That's like 10 high school buildings full of homeless people, like a small neighborhood that's entirely homeless. So when you kind of visualize what that number means. And then think of everybody talking about homeless people being on drugs here. We talked over, you know, or people who are clearly just using. Homelessness is a business. But now we're talking about a few people. Russia's thousands and thousands of people who are actually need help so soon. That perspective, I Yeah, I do love this argument. Yeah,

you really do have to look at the math as I thought that he had alluded to earlier and and it's we only react to the worst cases right toe What we can see. I I to this day. Just yesterday, Ah, homeless man approached me, who was pretty incoherent and was physically kind of was just that kind of in some ways a worst case scenario, Like what kind of physically a little repulsive in terms of hygiene and things like that smelled really bad. And it was harder for me, I admit, find a place to approach from a place of compassion. He approached me. It was very aggressive, about like, Hey, can I borrow? You know, I couldn't even understand him.

At first I think there was mental illness. There clearly smelled really bad And so I remember after I gave him $20 sometimes money is not. Oftentimes money is not the right answer, but and I we don't have the dye aggress, but But I can explain why I felt that that was appropriate at that time to give him $20. But as I drove away as I got in back into my car and drove away, I felt that I had this very visceral reaction because we're hard wired as human beings. A certain way to be like, Oh, that was so unpleasant and I sort of didn't want to. I wanted to blame him. God, why can't what does he have to, you know, wise, you have to be so aggressive or why is he But then But then,

after literally like 20 seconds, I'm up. You know, I don't have the full context of his story. He's clearly been on the streets a long time, and it is hella hard toe live on the streets to get beat up. Get your money stolen from you. The only way that you can stay warm is to drink tohave everybody not to look at you with dispersion and kind of treat you like a second class citizen. Those were not fun things, so I So I get it. I get the reaction that a lot of people have, where it's like a freakin Seattle's dying. And, you know, why don't we do something and you know and we should do something? And just to put a positive,

there are a lot of things that are working. The number of homeless has actually gone down from about 12,000 toe. About 11,000 went down by about 88 or 9% this last year. Precisely because there are great organizations like United Way of King County and Mary's Place. And many, many you know, there's eviction, reform and diversionary tactics and and rent assistance that we keep people from becoming homeless. We get the homeless rapidly, re housed these air great organizations, and these things are working. So again, don't. Don't you know that we shouldn't be cynical and say what? We're still a bunch of homeless people, so clearly these agencies are bozo,

so screw them. See, I was dying, right? No, that's that's not it. Double down on that. Things that are working and you're seeing now that the problem is getting addressed.

This is excellent point to wrap things up because, honestly, I think you're so multidimensional. We could probably talk for another four hours and record all of that. That would be interesting. So maybe that's for the next bit more about you. The next time were on, I want to be excellent. So we've got at least three more episodes with Jonathan May. But what? Speaking of you know, opportunity for the city and we talked a little bit about you are bringing in how yours apparent with everything combined. Like, what do you think we should do as parents, as a society to kind of move us forward in a positive direction, holistically, like you're already doing a lot of philanthropic,

Lee. But, you know, it starts with your Children, like you teach them right things to do. You teach them the right logic. What else do you think? Like anything that comes to my, you know, in between, Like the coding camps to being good to your peers, right? Like what? Maybe the top 5 10 things you think parents should focus

on? Yeah. Yeah, I'll give you some in kind of rough descending order of importance to us. Number one is self sufficiency. And with that also a lack of entitlement to things. Nobody's gonna give you nothing for free here. So go and earn it. And that kind of self sufficiency. He will do well, no matter what the second thing is. Always look for ways to build bridges. So in a society that's becoming increasingly more divisive, let's not add to the divisiveness. You know, let's find common ground. And I really think it's true we whether it's it's it's conservatives versus progressives or whatever.

We actually have Maurin common as Americans as then. We do differences, and I think that's important. Doesn't mean we shouldn't be passionate about where we're different. But there's always a way to say it more kindly to say something more respectfully, to say things in a way that doesn't prematurely make the other person disagree with you because you're pushing them away and angering them. So that's that's another one. Another important one is either change that you want to see. A lot are human reflexes to step back, and two complain. If you don't like something, be the change that you want to be. And oftentimes I think people are surprised when they do that that oh my gosh, I actually did catalyze that to change. You know, Leslie finds it is a great example.

The female Founders Alliance. You know what? There's no incubator technique debater for women. I'll start that right, and she's doing great. You know, there are others that are like, Who do you know the first example that popped in my head here? But there are many others, and I think lastly, never underestimate. And I'm wanting to be realistic about this, But humans have a capacity to be both good and bad. Never underestimate the capacity for us to be good if given a chance. So it's sort of related to the find a way to build common ground. It's a little bit different,

like like like find a way to enable others to be good. Yeah, so those are the things that I tryto talk to Holden about to varying degrees of success. Most of the time, I feel like I'm just asking him toe, get a shoes and socks on. We gotta leave. We're late.

Well, like you said, he's 10 and that's Ah There's still plenty of time and, ah, you're doing all the right things by the sounds of

it. And there's a lot of heat. I think there's a lot that I can learn from you. Cruel.

Any time. Yeah, but, you know, thank you very much for coming for sharing your story. We'll see what the listeners think about this. You know, if there are any questions, we can always do Part two. Yeah.

And happy. Too happy to do so. And thank you for giving me the opportunity and really appreciated your thought. Appreciative of your thoughtful, thoughtful questions. And we'll absolutely do it again if you if you want to. So, listen. Thank you. Yeah. Cool. Awesome.

That said, folks, thank you for listening to another episode of the ride, that show. And if you've got this far, I'm gonna go assume that you kind of liked it. So if you could, could you please send it to one of your friends? Somebody who needs to listen to this message or you found something interesting in this story? Just send to them, let him know. And the more people listen to the podcast, more of them, I can create. Also, if you go to smash notes dot com, you can find some notes on this and many other podcasts so that you can send interesting bits from every podcast to your friends wherever you find them. All right, well, until next time Goodbye.