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Civic Engagement and Government

Jason's civic life runs on two tracks that rarely appear in the same sentence: federal government technology under the Obama administration and local democratic organizing in suburban Massachusetts. The Presidential Innovation Fellowship gave him a front-row seat to the specific difficulty of changing institutions from the inside — and left him with a theory of change rooted in networks and people rather than programs and products. His father Anping's Newton School Committee campaign, meanwhile, demonstrated what civic engagement actually looks like at the scale where it can still be won door by door. Together, these experiences have shaped a view of government as something you participate in personally, not something that happens to you.

Presidential Innovation Fellows (PIF) — The Federal Experience

How He Got There

The Presidential Innovation Fellowship was not a planned career move. It was an escape hatch. In 2012, Ridejoy — Jason's long-distance rideshare startup, which had been featured on the first page of a Vanity Fair piece about Y Combinator, raised $1.3 million, and was briefly positioned as the American answer to BlaBlaCar — collapsed in a single month. Their iPhone app launched, generated press coverage and App Store featuring, and attracted almost no downloads. Then Craigslist, which had been supplying most of their user traffic, threatened legal action. Supply disappeared; demand evaporated; the marketplace was dead.

After eight months of failed pivots from a shared apartment — a social quote website, a laundry service, various dating and parking ideas, none of which the co-founders could agree on — Jason applied for the Presidential Innovation Fellowship almost as a private act: "I didn't even just say guys. I don't know if I can do this anymore." He applied without telling his co-founders, didn't expect to get it, and was surprised when he did. He told them, they processed it, and a month later they shut Ridejoy down, returned money to investors, and went their separate ways.

The decision was noted at the time by Gary Tan (then a YC partner, later YC president), who called the shutdown a mistake and suggested they could just pivot into solving problems for YC portfolio companies. They couldn't. "We ran out of resilience," Jason later wrote, "not money." The fellowship was the off-ramp they needed.

What He Did There

Jason served as a Presidential Innovation Fellow at the Smithsonian Institution under the Obama administration. The PIF program's premise was that the federal government needed technologists, designers, and entrepreneurs embedded inside agencies to apply private-sector methods to public-sector problems. The Smithsonian was one of those agencies; Jason worked on product and technology initiatives there. His LinkedIn bio still lists it alongside Etsy and Facebook Groups as a major product role.

The healthcare.gov crisis — which happened during his fellowship period — became an accelerant for the broader government technology movement. The emergency "fixit team" that was assembled to repair the broken ACA enrollment site included both of Jason's Ridejoy co-founders, who were recruited by Google engineers parachuted in to fix the site. Those co-founders went on to found Nava, a government technology services company that is still operating today with around 50 people. The fellowship, in other words, created a network that branched: Jason went to New York and eventually to Etsy; his co-founders stayed in D.C. and built a company around the problem.

The Theory of Change

The PIF experience produced a theory of change that Jason articulates directly in the archive. The program's design assumes that technology projects will change government. But the actual mechanism of change, as observed from the inside, is something more diffuse: it's about building networks of people willing to say "I am a change agent." The program cohorts — roughly 40 fellows per batch, a cross-section of tech entrepreneurs, designers, researchers, and civic innovators — function less as project teams and more as a class of people who now know each other and know that government change is possible.

Practical lessons from the first PIF cohorts included in the archive:

  • Prototype fast and find "internal innovators": Every federal agency has people who want to do things differently; the fellowship's job is to find them and give them cover and momentum.
  • Use White House air cover strategically: The association with the White House provides credibility that helps get meetings, but it's a limited resource. Deploy it for the most important conversations.
  • Celebrate agency victories: Government work produces wins that go uncelebrated because agencies don't have marketing functions. Making those wins visible — internally and externally — creates momentum and makes the change agents feel seen.
  • Advertise success stories rather than always building new things: The instinct to build is strong among technologists; the government context calls equally for documentation, replication, and evangelism of what already works.

The broader observation is that government change is primarily a human problem, not a technical one. The same insight shapes Jason's coaching practice — change requires finding the internal change agents, giving them air cover, and celebrating small wins to create momentum toward larger ones.

The D.C. Decade Later

When Jason returned to Washington D.C. a decade after the fellowship — accompanying Amanda to PCAH (President's Committee on the Arts and the Humanities) events — the city produced a specific kind of reflection. The DC Walk essay reads: "the street grid, fall air, and grand monuments reminded me of my time in this city a decade prior in a government tech fellowship where I understood very little about how organizations worked."

The self-assessment is pointed: he didn't understand how organizations worked then. He does now — partly because of the fellowship, partly because of everything that followed. The walk becomes a meditation on risk and guarantees: "I had taken a leap after my startup Ridejoy had run aground, not knowing what would happen after the 6 month program ended. Unlike traditional government jobs, this one carried no guarantees. I moved to New York and spent 9 weeks sleeping on different friends' couches until I landed a job and then an apartment." The fellowship was a risk that worked. It was also a useful reminder, for the executive coaching clients he now serves, that operating without guarantees is the normal condition — not an exception.

Anping Shen's Newton School Committee Campaign

The Race

In 2017, Jason's father Anping Shen ran for Newton, Massachusetts School Committee, representing Ward 3 — and won. The campaign story is documented in multiple raw files and has become a reference point in how Jason talks about civic engagement at the local level.

The mechanics: Anping raised $12,000. He knocked on more doors than any opponent. He mobilized the local Asian American community in ways that had not been done before for a local race of this size, increasing Asian American voter turnout in the ward. The organizing demonstrated directly that the conventional wisdom — "Asian Americans don't vote," "Asian Americans don't run" — was not a fact but a self-fulfilling expectation.

The key moment was not strategic but personal. When a constituent claimed that Newton's schools were antisemitic, Anping responded: "I lived through the Cultural Revolution. You have no idea what you're talking about." The response worked not because it was tactically smart but because it was true. His credibility came from lived experience with actual ideological coercion, which gave him standing to call out what was and wasn't comparable to it.

What It Demonstrates About Local Politics

The campaign produced a set of civic lessons that Jason returns to repeatedly:

Door-knocking outperforms digital outreach for local races. At the local level, personal contact is still decisive. Anping's willingness to knock on more doors than anyone else reflected a different theory of voter contact than digital-first campaigns assume. In a city ward, you can actually reach a meaningful percentage of voters in person if you work at it.

Mobilizing underrepresented communities can shift outcomes. Newton's Asian American community was not highly activated civically before this campaign. The Shen campaign created activation in a community that was already there — it just hadn't been invited to participate at scale. This mirrors broader arguments in Asian American political organizing: the limiting factor is often mobilization, not registration or interest.

Personal credibility and trust matter more than party affiliation at the local level. Anping ran on the strength of who he was — an educator, a community member with a long track record — rather than as a partisan. The personal relationship with voters was the product.

The experience challenged a stereotype that functions as self-fulfilling prophecy. The assumption that Asian Americans don't vote had suppressed outreach and organizing in the community for years. The campaign broke the assumption by simply organizing as though it weren't true.

See also family-and-personal-history for Anping's full biography and the Confucian milestones letter he wrote Jason the same year.

Civic Frameworks in the Archive

Eric Liu's Civic Saturday and Power Literacy

The Fairness raw file includes notes on Eric Liu's framework for understanding civic power — the same Eric Liu who founded Citizen University and developed the Civic Saturday concept (democratic engagement modeled on a faith gathering, but organized around civic participation rather than religion). Liu's "three laws of power" appear in the notes:

  1. Power is always accumulating or decaying — it is never static.
  2. Power is like water; it flows in different directions depending on the landscape.
  3. Power compounds.

Liu also catalogs the sources from which power can be drawn: physical force, wealth, state action (law and bureaucracy), social norms (peer-to-peer), ideas (changing how people think and act), and numbers (large groups expressing organized interest). The distinction between "read power" (understanding how power works) and "write power" (exercising it) runs through his work. Jason's family history — immigrant parents who raised a son who now coaches other founders — is itself a story of power accumulation across generations.

The Walking-as-Public-Health Proposal

One raw file documents a White House Fellowship application that proposed a six-month federal walking-break pilot program. The proposal called for using agency-level competition — modeled on the same logic as FitBit challenges or team step-count competitions — to study the effects of regular walking breaks on productivity, absenteeism, and metabolic health.

The proposal sits at the intersection of several of Jason's persistent interests: the research on movement and cognitive performance (see stress-and-performance-science), the government as a design and product challenge, and the specific leverage point of using federal agencies as research platforms and demonstration sites. The logic was that if a federal agency ran the experiment at scale, it would generate both data and a replicable model that private employers could then adopt.

Restorative Justice and Deviant Heroes

The archive includes notes on restorative justice — the set of practices that offer alternatives to punitive justice systems by focusing on repairing harm rather than assigning punishment — as a civic framework worth understanding. Related notes on "deviant heroes" document research on how nonconformists and rule-breakers have historically driven social change and justice reform.

These appear less as a practiced commitment and more as intellectual frameworks Jason tracks — part of a broader interest in how institutions change, how power works, and how individuals operating outside conventional expectations end up shaping the systems they're embedded in.

Government as a Product Design Challenge

One of the recurring reframings in the archive is that government is a product — and that the product management principles that apply to software apply, with modifications, to civic institutions. The PIF fellowship was essentially an attempt to embed PMs and product thinkers in federal agencies. The healthcare.gov crisis was a product failure with enormous stakes. Anping's campaign was a campaign, but it was also a distribution problem: how do you get your message to the right people at the right time through the right channels?

The Singapore dinner conversation in the archive offers an example of what government-as-product can look like done well: Singapore planned to digitize all consumer-facing government services by 2024 and finished two years early. The comparison to U.S. government tech timelines is implied. Jason's interest in this space is not merely academic — it's rooted in having spent six months inside a federal agency trying to move it.

The broader principle: civic engagement is not just about voting or running for office. It's about treating public institutions as systems that can be designed, improved, and iterated — the same way you'd treat a product — with the additional constraint that the stakeholders include everyone, the feedback loops are much longer, and the political environment changes the context constantly.

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