A letter grade can conceal an astonishing amount of information. A student gets a C, and the conversation promptly becomes about the C. Which ideas clicked? Which ones need another attempt? The alphabet, having delivered its verdict, declines to elaborate. Riley Eynon-Lynch’s first education company grew out of that problem. Years later, after co-founding Pear Deck and selling it with his colleagues, he began asking a related question about Iowa City: what should a community put on its report card?
The scale of that second question is visible in a decision he and his wife and fellow founder, Michal Eynon-Lynch, made in 2021. They established Resilient Sustainable Future for Iowa City, or RSFIC, and donated $20 million, representing most of the proceeds from their entrepreneurial success. The money went toward a foundation concerned with neighbors, shared resources and the practical business of living together. A technology exit had acquired a distinctly local destination.
There is an appealing continuity here, though it would be too tidy to call every chapter part of a master plan. Grades, classroom presentations and neighborhood institutions are different things. Yet each raises a question Riley has returned to in public: who gets to participate, and what information helps people do something useful next?
A spring-break call, then a gradebook
Before the companies, Riley taught high-school math and science. His education included a bachelor’s degree in computer science and mathematics at the University of Maryland, College Park; his working life also included directing summer camp. The programmer and the teacher were therefore already acquainted before they went into business together.
In eastern Iowa, Riley and Michal experimented with standards-based grading, tracking students’ understanding in spreadsheets. The spreadsheets eventually proved inadequate. During spring break in 2010, Riley called Michal with a proposal: “I think I could make an awesome tool for SBG.” They moved to Iowa City that summer, and he began programming in the fall.
The resulting company, ActiveGrade, brought them together with designer Dan Sweeney. Its gradebook organized progress around concepts and skills, with color-coded views that helped teachers see where students needed attention. A completed assignment could contribute evidence of learning without becoming the whole definition of it. That distinction gave a teacher something more useful to discuss than the final arithmetic of a grade.
By early 2013, Haiku Learning had acquired ActiveGrade. The team stayed in Iowa City and worked for Haiku. A sale might have supplied a satisfactory ending to the story. For this group, the pleasure of starting something remained inconveniently persuasive.
The same hands kept going up
Pear Deck followed in 2014, co-founded by Riley, Michal, Sweeney and Anthony Showalter. Its starting point was familiar to anyone who has watched a teacher ask a room a question: a few students answer; the rest become an audience. Silence is wonderfully easy to mistake for comprehension, particularly when the clock is running.
The product let a teacher put questions into a presentation and receive responses from students on their own devices. Text, drawings and other interactions made it possible to hear from more of the room. Teachers could inspect individual answers privately and share responses anonymously with the class. A student could contribute an idea without having their name projected beside it.
Riley’s teaching experience mattered to the way he built. In 2014, he described an online network of roughly 1,000 teachers reached through his blog and Twitter. Those relationships gave him people to consult and a way to get reactions to prototypes. Familiarity with classroom work also meant familiarity with the difference between a lovely demonstration and a tool someone would actually use on a busy Tuesday.
“Having experience struggling and succeeding as a teacher helps me relate to teachers and helps me design tools for teachers.”
Riley Eynon-Lynch, 2014
That is a modest account of expertise, and a useful one. Struggling belongs in it. A product built for teachers has to survive the daily demands that made its creator want to build it in the first place.
Sixty seconds is a serious unit of time
At ISTE in 2015, Riley demonstrated an integration with Google Classroom’s API. One benefit was small enough to sound unglamorous: students could join without the customary business of entering a six-character code. Teachers could send invitations to groups instead. He described a minute of frustration at the start of class being reduced to zero.
A minute is an unimpressive trophy in a pitch deck. Inside a lesson, it is time the teacher can spend on something else. This part of Riley’s work makes the business easier to understand: the technology was supposed to fit around teaching, with less ceremony at the point of use.
By July 2016, Pear Deck reported more than one million student users across 40 US states and 15 countries. It had opened a Kansas City office to develop its sales team while keeping its Iowa City base. Riley spoke appreciatively about the entrepreneurial community there. The expansion carried the practical recognition that a good product still needs people who can introduce it to customers.
In March 2017, Growth Street Partners and existing investors announced a $4 million investment. Riley said the partnership would support product work, growth and the company’s mission of helping teachers engage students. Building something useful and building the organization capable of delivering it had become parallel jobs.
The camp director stays in the picture
Riley’s account of education reaches beyond the classroom. In a 2018 essay about summer camp, he wrote about helping children believe, “I can do some hard things!” He placed that aim across his experiences as a teacher, camp director, father and Pear Deck co-founder.
It is a revealing choice of sentence. There is room in “some” for judgment, practice and another attempt. Children do not need an extravagant promise that everything will be easy. They need occasions to discover that effort can change what they are capable of doing. Read beside the gradebook and classroom products, the camp essay offers a more personal vocabulary for the same educational interest.
By 2019, Riley was demonstrating Pear Deck’s Microsoft integration at ISTE. His stated aim was to use technology to support human relationships in school and create meaningful learning moments. The human interaction remained the point of the exercise, even when the demonstration required an impressive number of accounts, screens and product names.
A sale, and a different use for the proceeds
GoGuardian announced its merger with Pear Deck in November 2020. At the time, Pear Deck was used in more than 17,000 schools and by eight million educators and students worldwide. Those figures describe the company at that moment, rather than Riley’s current reach or a promise about what came afterward.
The transaction’s financial terms were undisclosed. The next public chapter, however, included a specific financial commitment: Riley and Michal’s $20 million donation to establish RSFIC in 2021. They chose Iowa City as the place to work on resilience and sustainability, bringing resources from an education business into local buildings, organizations and relationships.
That choice changes the shape of the founder story. The interesting question becomes how money can help people organize, share resources and develop the ability to do things together. Owning an asset is one matter. Making it useful to a community requires arrangements, trust and people willing to keep showing up.
The awkward education of a foundation
RSFIC’s early Building Equity program offered entrepreneurs access to property at low or no rent, reducing the financial risk of trying an idea. Three organizations participated. The foundation later stopped accepting new participants into that program, explaining that a building or major piece of equipment could be too large a commitment before a relationship had developed enough trust.
There is something refreshing about an institution admitting that generosity does not automatically settle the difficult questions. Who makes decisions? What happens during a disagreement? A building comes with a roof, but rarely with a complete theory of cooperation.
In 2022, RSFIC set out to interview 50 local leaders and ended up speaking with almost 100. Its account describes people with overlapping intentions separated by mistrust and old divisions. The foundation’s own shared premises also provided lessons, including questions about room allocation, meetings, signage and who should pay for toilet paper. Civic ambition eventually has to visit the supply cupboard.
Its work now includes neighborhood projects, gatherings, skills sharing and Neighborhood Resilience Groups. Riley is listed as vice president of RSFIC’s governance board; Tyesha Perry is executive director. The division matters: the work has an organization and other leaders, rather than existing only as an extension of its founders.
Who writes the report card?
In December 2023, Riley wrote about Iowa City’s bond rating. He questioned the habit of treating an outside investor’s assessment as a primary measure of civic success, arguing for indicators chosen to reflect residents’ own priorities. The former gradebook builder had found another grade worth interrogating.
RSFIC’s collaboration with FilmScene gives that concern a public, enjoyable form. Their short films celebrate neighbors organizing projects, sharing skills and making things happen locally. The subjects include a repair cafe, community food projects, murals and neighborhood music. These are stories with recognizable people in them, offering an invitation to participate.
Riley’s current RSFIC biography lists intentional communities, online videogames, teaching, entrepreneurship and summer camp among his experiences. Its book list runs from Ishmael and Braiding Sweetgrass to Gödel, Escher, Bach. The combination suits a career spent moving between systems and the people inside them.
The foundation’s published strategy looks toward neighborhood groups that can eventually support themselves. That remains an aspiration, requiring work and revision. It also supplies a fitting next question for Riley: after building tools that helped teachers hear more students, how might a city make more room for its neighbors to act?