In this episode of the On Purpose podcast, host Kristin interviews Jessica Chang, founder and CEO of Upwards. Jessica shares how her upbringing in post‑Cultural Revolution China, where community members helped raise her, shaped her view of collective childcare. A personal catalyst was her younger brother’s autism, which led her to study psychology and early childhood development. When she became pregnant, she struggled to find affordable, timely childcare, eventually leaving her job and later purchasing a preschool to understand the problem firsthand. She explains the U.S. childcare crisis: average costs of $1,200‑$1,500 per month per child exceed public college tuition in many states, forcing parents out of the workforce and costing the U.S. economy an estimated $300 billion annually. Upwards tackles the issue by building a nationwide network of small, local providers that offer 24/7 care, making childcare about 40 % more affordable for families, especially in rural areas. Jessica emphasizes the entrepreneurial mindset of persisting through repeated rejections—she recalls hearing roughly 100 “nos” for each “yes”—and argues there is never a perfect time to launch; passion and personal stakes should drive action. The conversation blends personal narrative, economic analysis, and practical solutions, offering lessons for aspiring entrepreneurs and highlighting Upwards’ mission to solve childcare sustainably and equitably.
With a lot of entrepreneurs, the question is always like, when is the right time? And what I've learned over the years is there's no right time.
Hello and welcome to On Purpose. Today I'm joined by Jessica Chang, the founder and CEO of Upwards. Welcome, Jessica.
It's great being here, Kristin.
So I wanna start with your upbringing. I often find that people's upbringing help shape the leaders they become. So talk to me a little bit about where you were raised and how that helped shape you.
I actually grew up in Asia, well, specifically China, right after the Cultural Revolution and at the start of the one-child policy. So, like in most Asian cultures, parents expect their first child to be a boy. And when you only have one shot and you get a girl, my parents were like, okay, we're gonna put everything into her.
No pressure.
No pressure at all. We're gonna raise her like a boy, but we want her to be independent. And it was really interesting because back then both my parents were working and the community actually raised me. And that was kind of the earliest setting that I had. I thought it was normal for my next-door neighbor to raise me or for my grandma to raise me. And that was exactly how we thought about Upwards as well.
So what brought you to the idea of, you know what I need to solve? I need to solve the childcare crisis.
Actually, there's a lot of things that kind of brought me here. When I went to college, I actually studied psychology and early childhood development. And the reason why I did was my brother, who's 17 years younger than me, was born with autism, and my parents didn't I didn't really know what to do. And so I really wanted to understand how minds would evolve, but how would preschool impact him and how my family would be able to deal with it. So pretty early on, I had the degree, didn't do much with it until I actually decided to get pregnant. And that actually wasn't the greatest experience because when I got pregnant, I went to look for childcare and everything I looked at was either unaffordable or waitlisted for 6 months to 2 years. I ended up having I remember having to leave my job because I couldn't find childcare. And long story short, I actually became a preschool owner and operator because fundamentally I didn't understand why it was so hard and why this was a problem for generations and no one had solved it. And until I became a preschool owner and operator, I finally understood all the complexities of childcare, which really then catapulted to say, hey, this is what I'm meant to do.
The first time you and I met, one of the stories I remember you told me was how would you When you would bring your idea to investors, they're like, what childcare crisis? So walk our listeners through what the business case is to solve the childcare crisis in the US.
Childcare's a really complex issue. Like, if you talk to anyone, everyone will say it's really unaffordable. I mean, $1,200 to $1,500 a month for one child. It's even more expensive than the cost of public college in more than 50% of the states. So when you come and you speak to families, they'll say, I can't afford childcare. And if I can't afford childcare, Someone's gonna have to stay at home. So you're losing potentially a parent to the workforce. Think about it. If half of your workforce isn't participating because they don't have childcare, the US economy literally loses $300 billion a year. That's an economic issue.
So talk to people who don't know Upwards well what you really transformed in the sense of access at a local community level to childcare.
So when we first started the company, we've always been on a really local, ambitious mission, which is how do we solve care for good? And good has basically 2 meanings. One, it's how do we solve it sustainably so that, you know, the future generations, they don't have to face the same thing that we have. But also, how do you solve it for good for like, hey, how do you do good? How do you solve it for the person that truly needs care? So when we built out our network, we really focused on small childcare providers, right? The people that are actually Providing care, the people that need to get paid to stay in the industry. And when we did that, we ended up actually having a network that was nationwide in rural areas that could do 24/7 care. So when you think about it, that actually made it, one, a lot more convenient for every employee, the person that's working a second, third shift, or weekend shift. But on top of that, because we supported the infrastructure of our providers, It made it 40% more affordable for families, which meant that families that traditionally couldn't actually consume that childcare or pay for it, suddenly that was actually now available to them.
One of the interesting insights I had from listening to you is how many nos you had to get to get to a yes. So talk to me a little bit about what it was like to prepare yourself for— I think you said it was 100 nos or something for every yes that you would get. And what lessons you'd share for, you know, young entrepreneurs about what it takes to succeed?
I think this is actually ingrained into me at a very young age. It's like, if someone says no, then it makes you even more motivated to say, okay, well, I'm gonna find the person that's gonna say yes, 'cause I believe in what I'm doing and it matters a lot. And it doesn't matter how long it takes. That might be called stubbornness, but—
To be an entrepreneur, you gotta be stubborn.
But I think that's the amazing part to it. And I think with a lot of entrepreneurs, the question is always like, when is the right time? And what I've learned over the years is there's no right time. You just need to jump in if you're super passionate about it and this motivates you or affects you in a way that you can't sleep. Go do it because someone will say yes, because someone is looking at you and saying, this is the person that regardless of how hard it is, they're going to push forward.
Well, I want to thank you for all you've done to address, I think, one of the biggest crises in America around childcare. And I want to thank you for joining me today. And thank you for joining this episode of On Purpose. I look forward to seeing you next time.
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