
20 Questions with Rod Hsiao ’82, Equity and Entrepreneurism
Any parent of school-aged children will tell you: filling kids’ summers is hard. But Rod Hsiao ’82 knows the problem goes deeper than the scramble to find summer camps. Those months away from school can torpedo students’ momentum in the classroom and deepen achievement gaps along socioeconomic lines. He’s spent his career trying to close that divide by improving access and outcomes for students, moving from academia to government to the private sector and back again. Commonwealth (and Polly Chatfield in particular) helped propel him down the winding path that eventually led him to co-found InPlay, a nonprofit that helps under-resourced families find the summer and after-school programs that can change the trajectory of students’ lives. Keep reading for a deep dive into his entrepreneurial adventures, followed by our twenty questions interview where he shares memories of Mrs. Chatfield, the misconceptions undermining summer programs’ success, and his definition of nirvana.
An Entrepreneur’s Journey
Fast forward a couple years after Commonwealth, when Rod took a year off between his sophomore and junior years at Oberlin. “That's where I took the road less traveled,” he says. First, friends convinced him to travel to Alaska, where he lived in a tent city and worked at a salmon canary for $6 an hour—a generous wage at the time. He then hitchhiked down to Seattle before making his way back to Cambridge, where he worked at a futon factory, saving up to go teach English in China. “That was such a great experience, being on my own, exploring things, and just trying to piece everything together along the way.”
Rod finished teaching in China and took advantage of visiting Tibet when it had just opened up to visitors, and he decided to explore the Indian subcontinent by bus and hitchhiking. Seeing people living on the street, particularly young children, shifted his perspective and priorities. “It didn't seem like there was any system to take care of them, particularly in Tibet,” he recalls. “So I thought, there ought to be something we can do to help.” He went back to Oberlin, changing his major from history to economics with a focus on international development. After graduating, Rod took a job in Yale’s Economic Growth Center doing econometric modeling and research, but he felt “too far away [from] helping kids and families on the ground,” he says. “I want to be at the table where we're funding and designing programs to help these families.”
Following a stint with a social service agency that helped recently arrived immigrants in New Haven, Rod went to work in various congressional offices in the U.S.: first for Louise Slaughter (D-NY), then with the banking committee for international development trade finance, and finally for Bob Matsui (D-CA). Working for the latter, Rod saw firsthand the potential and pitfalls of trying to convert staff and expertise at military bases to engage in private commercial work—“converting swords to ploughshares”—when four military bases in Rep. Matsui’s district closed. That experience, in part, inspired Rod to get his Master of Public Policy from the Harvard Kennedy School, with a focus on technology transfer and manufacturing modernization.
“I'd been in academia, I'd been in government, and I really wanted to help businesses transition from being reliant on defense contracts…to more competitive markets, but I realized I didn’t know anything about business,” says Rod, remembering that post–grad school period. So he moved to Menlo Park, California, at the advent of the dot-com boom, to work in management consulting, helping businesses implement new technologies. He managed to stay out of politics (“all that messiness”) for ten years, but he “eventually realized: I'm too far away from my true passion in economic development, helping people, and policy work in the public sector.” Friends pushed him onward once again: “it's time for you to get back into the policy world.”
Elected to the San Mateo County Board of Education in 2006, Rod served for fourteen years, “always trying to close the achievement gap” for school-aged children. That gap, he learned, could turn into a gaping maw over the summers, with even more acute learning losses for low-income kids. One Johns Hopkins study looking at summer learning loss struck Rod in particular. “If you could get kids in the bottom quintile engaged in high-quality summer programs,” he relates, “you would close two-thirds of the achievement gap in reading and math skills.”
At that time, the startup world was taking off, and Rod “caught the bug,” deciding that there ought to be some technological solution that could help underserved families find and enroll in enrichment programs. “I just started interviewing grocery-store clerks, truck drivers, custodians, and they all shared how hard it was to find programs,” he says. “If you ask any parent, regardless of their educational level or their income level, about summer programs for their kids, they all say it's hard, but lower-income families really struggle.” Maybe they don’t speak English or they work two jobs or grandma watches the kids during the day. They have to figure out what works with their schedule, who can manage drop off and pick up, what they can afford. It's really complicated, and they don’t have the information they need at their fingertips, like many more affluent families do, Rod says.
Rod started looking at this problem through the lens of behavioral design, particularly the work of Stanford professor B.J. Fogg. If you want somebody to take an action, say, taking care of their teeth, three things that have to happen: First, you have to give them the motivation. “Here are photos of people who have tooth decay; you don’t want to lose your teeth.” Second, you have to give them a social cue. “Hey, don't forget to brush your teeth.” Third, you have to make it really easy for them to take action. “The floss is right there next to your toothbrush.” And all three things have to happen at once. “So I thought, Okay, how should I apply this model to helping underserved families discover summer programs?”
In 2014, Rod formed InPlay and started going to some district superintendents, pitching them on a small group of summer programs that offered scholarships. Those programs were struggling to find families eligible for financial aid, in part because the scholarship applications were so onerous that parents didn't even apply: “you have to provide evidence of your household income, and it can ultimately feel very demeaning" if a family is denied financial assistance or if they do not technically qualify for enough money, Rod adds.
Looking for ways to reduce the friction of applying for summer programs, Rod and his team had the school districts include a flyer from InPlay when families qualified for free and reduced-priced lunch: "Do you need assistance for after-school or summer programs? Here are three steps you need to take, and here's a QR code you can scan right now.” They sent out about 100 flyers, heard back from ten percent of parents, and texted them a list of the programs with scholarships. “All the program providers understood that when we refer a family to them, they don't need to ask for a financial application and should treat them like any other family,” Rod notes. And it worked. They placed kids in summer programs with pricetags as steep as $5,000, for free. “That scholarship matching service was pretty cool,” Rod says. They ran similar pilot programs in lower-income neighborhoods in San Francisco and San Jose, too. “All well and good,” Rod says, hinting at a hunger for something more.
In 2019, Rod had just finished giving a talk at a conference when a summer program administrator from Seattle Public Schools came up to him with a slightly different problem: once he opens up registration, all the more resourced families rush in and grab the spots. Families from low-income backgrounds, the English language learners, even kids with some special needs: they miss out. “Could you offer an online registration system just for these families?” the admin asked. “Sure,” said Rod. “So we moved from the scholarship-matching service to a one-stop shop where we would text the family a unique link to sign up and strip off all of the bureaucratic red tape and just say, ‘Do you want your child to be enrolled in a free summer program? If so, click the link below.’ And they each got a unique link, and they got to shop and browse programs like any other family.” From there, the application process is seamless, using prefilled information families had already opted into sharing. All they have to do is confirm their info, and it can be completed on a smartphone.
“A lot of parents who work hourly wage jobs are just so busy,” Rod says. “We stripped out all of the friction that was stopping a lot of the families [from applying].” Soon, school districts in Oakland, San Francisco, San Diego, and Central Valley wanted in; today, InPlay serves about 45,000 students in 160 school districts across all fifty states.
“We're still small, but it gives us a lot of satisfaction that we're giving first dibs to the people who most need it, and these kids are getting wonderful out-of-school time programs,” Rod says. “And who knows where things are going to go next.”
20 Questions
1. What was your favorite Commonwealth class?
Man, I loved Geometry with Leland Giovannelli—and that was the only math class I really enjoyed, because I struggled in all the others. Or my favorite might be U.S. History with Paul Jefferson or Renaissance History with Polly Chatfield. We were getting below the text and putting ourselves in the shoes of the revolutionaries or philosophers, and having such original creative thoughts—that's what I really enjoyed about the discussions we had.
2. What is your favorite memory of Mrs. Chatfield?
I was a struggling student, and she pulled me aside sophomore year in her Renaissance History class. I remember putting the textbook in front of her, and she said, "All right, Rod, let's look at the question. What do you think the key point is?” She helped me to sharpen my thinking and answer in a more lucid, articulate way. And it took a few tries, but I eventually did get an A on one of her Monday quizzes, and I was so happy with that. I've always cherished that memory of having somebody who saw I needed help and said, "Let's go sit down in the library and get this done.” (I ended up exchanging Christmas letters with her for almost twenty years.)
3. What is your favorite memory of Commonwealth?
I really enjoyed announcements, where everybody got to stand up and just say, "Hey, I'm going to go to this demonstration, or I'm going to go to this theater play. Does anybody want to join me?” I just thought, “Wow, it's okay to really care about something so early on.” I loved that. There was so much debate and deep engagement, and I thought that was part of the unseen connective tissue that made Commonwealth a community.
At Commonwealth, yes, the academics were great, but I felt like I had this social awakening. I loved [assembly]. It just gave me a little window into what all these different people did with their lives and what they cared about. I just remember, for the first time, I really saw how passionate someone could be.
4. What’s your #1 piece of advice for Commonwealth students?
Create your own opportunity. Go out and do informational interviews. Don't wait for somebody to post the job you want; go in and just show your interest, show your love for what they're doing, and your curiosity. And then show that you can take the ball and run with it by doing a bang-up job.
5. What myth(s) would you like to dispel around your work?
Thinking of summer and after-school programs as daycare, babysitting, when they could be something much more rich. If kids have more opportunities to get hands-on learning outside of school, where they demonstrate their agency, their creativity, their critical thinking, that's going to serve them well, especially in this new world of A.I. When students in K–12 systems have more experiences where they can develop a passion around what they do, and with some caring adults around as well, that can help them discover more about themselves and what they're good at, which can undergird their sense of identity and intrinsic motivation, and ultimately carry them forward.
6. What is your favorite aspect of your career?
Definitely starting InPlay, because it wove together everything I’d done so far: working on policy, operational efficiency and effectiveness, and social justice. All three came together with the ability to be an entrepreneur and dive deep into solving a problem.
7. What do you imagine/hope for InPlay in the next ten years?
My vision for InPlay is to not just work with school districts but include cities and other organizations to create a true one-stop shop. I would love to knit together this very fragmented market to make it easier for families. A working parent doesn’t have time to look at what their kid’s school offers, what the city’s parks-and-rec department offers, what other community-based organizations offer. It should be all brought together, particularly if the programs are free or low cost, so parents can find them easily.
8. How do you define success?
Feeling like I was able to bring my very best to help certain people and make a difference for those people. We’re not solving global hunger, but we now serve about 45,000 kids a year, and, at least in my little corner of the world, we offer something that makes sense to people who use it and strips out all the friction that stops families from accessing these opportunities. It's a two-generation solution, because it’s helping the kids have great experiences and hopefully do better in school, and you're helping their working parents.
9. If you could study any field aside from your own, what would it be?
I started off in economics, which has these great quantitative models, but underneath that it's human behavior. So I would have liked to study something around user experience and behavior design.
10. What does your ideal afternoon entail?
Having a good workout, and then being left alone to read. I love fiction: The Three-Body Problem. Demon Copperhead. I just read The Correspondent. Anything where the writer is able to develop the inner life of the characters—I just think that's such a talent.
11. Whom do you most admire?
I was surprisingly sad when Jim Henson died. I just thought, Oh my gosh, if I could look back on my life and know I helped create this world [on Sesame Street] that helped kids and became a vehicle for all these people who care so much and want to teach social-emotional learning and reading and do it in such a creative way—that'd be a life worth living.
12. What are people surprised to learn about you?
A coworker once said, "Rod is surprisingly passionate about equity." I’ve been saying we have to invest in access and equity for our students for about eighteen years! That is what I'm pouring my life energy and time into.
13. What book do you wish you had read sooner?
In college I read Getting to Yes [by Roger Fisher and William Ury]. I was so glad I read it, and it really did change a lot of how I dealt with people, particularly in times of conflict. I don't know if I would have benefited from it if I had read it, say, at Commonwealth. But it definitely opened my eyes to seeing things from another person's point of view.
14. What is your favorite museum?
It’s not a particular museum, but I just love those spaces that feel accessible and convenient—where I can pop in and feel like I’m having that part of my soul filled with somebody’s vision. The Allen Art Museum at Oberlin was like that. Even art galleries where you can walk in and say, “Hey, that's pretty cool. I'd like to learn a little bit more about that artist.”
15. What do you bring to a potluck?
Usually, some Chinese side dish, like a leafy green stir fry with a little bit of oyster sauce or rice wine.
16. What was your go-to Boston eatery?
I used to collect my money from delivering newspapers, and every Saturday, my friends and I would come into Harvard Square, and I'd deposit half of it at the Cambridge Savings Bank and spend the other half. There was a diner called Lee’s Sandwiches on Church Street—I think it’s a Dunkin’ Donuts now—where you could just get a plate of hamburgers and French fries. That was nirvana.
17. If you could live as a local for 48 hours anywhere in the world, where would you go?
Probably somewhere in Southeast Asia. I'm actually trying to find a place where I can take the whole family and we can volunteer for a month. My kids live in the Silicon Valley bubble. I’d like them to be around more people who have their priorities straight: have good health, a roof over your head, food to eat.
18. If you could join any past or current music group, which would you want to join?
I once dreamt that I was playing the banjo with REM…
19. What is the best gift you have ever given?
I organized a Jeopardy game for my now-wife’s birthday, turning various aspects of her life into trivia questions. I invited all her closest friends, coworkers, and our church friends, and I made a big Hawaiian dinner. So it wasn't a physical gift; it was a birthday experience.
20. What is your motto?
Just because you can doesn't mean you should.
