David Haisha Chen and the useful art of getting it wrong

David Haisha Chen went looking for money and found a website. At the University of Chicago, where he served in student government, people kept arriving with projects that needed funding. His first startup offered an answer: a crowdfunding platform for campus groups. Let members contribute. Let the projects happen. It was a reasonable idea, with one inconvenient detail. The people using it seemed more interested in having somewhere to explain themselves.

They needed a public face for a campaign, an organization, a weekend experiment. The fundraising platform was doing an unadvertised second job. Chen and his collaborators had built a way to collect contributions; their users were treating it as a place to say, here is what we are making. The useful business was tucked inside the unsuccessful one, rather like finding the only good room in a house you intend to demolish.

That observation became Strikingly, the website builder Chen cofounded in 2012 with Teng Bao and Dafeng Guo. Its early promise was straightforward: get something online without first becoming a programmer or a designer. For Chen, the customer was unusually easy to picture. He had been that customer, repeatedly, and he was tired of asking a technically capable friend for another favor.

The budget line nobody could escape

Student government gave Chen a view of a problem that was both ordinary and expensive. Alongside food for events, website building kept appearing in requests for funding. Organizations needed to tell people what they did, and putting that explanation online could absorb thousands of dollars. A modest student project arrived with a surprisingly immodest technical bill.

Chen himself depended on Bao to make websites for his activities. That meant waiting until Bao had time, while Bao inherited another task. Their inconvenience was small enough to sound trivial and persistent enough to become a company. There is a particular kind of product insight available to the person who keeps having to ask, sorry, could you help me with this again?

His campus work extended beyond websites. He cofounded Moneythink, the nonprofit focused on financial education, and handled fundraising and events. He also helped establish the university’s Uncommon Fund Board for entrepreneurial student projects. Before he was selling software to people with ideas, he was already involved in the machinery that helped those ideas get a hearing.

A friendship with a slightly modified iPhone

The founding team came together through existing friendships. Chen and Bao had lived in the same dorm during their first year. Bao worked on Moneythink’s design and development and managed Chen’s campaign for student government vice president. Their working relationship already included deadlines, persuasion and the practical business of making something other people could use.

Guo met Chen during a Goldman Sachs internship in 2010. Their friendship began after Guo helped jailbreak Chen’s iPhone. The detail is almost too well suited to a software origin story: banking supplied the introduction, and a small act of technical disobedience supplied the friendship. They put internship earnings into JoinStart, the crowdfunding venture that preceded Strikingly.

The first idea ended; the team stayed together. This distinction matters. Abandoning a project can also dissolve the relationships built around it. Here, the collaborators had enough confidence in one another to keep looking. Chen’s later account of applying to Y Combinator makes their shared history part of the argument for the business. The founders had already worked through a disappointment together.

The landing page won the argument

When the team tested the website idea, the response changed. A landing page attracted roughly 800 to 1,000 signups in about a week and a half, Chen recalled in 2015. That exceeded what the crowdfunding project had collected over nine months. The comparison gave the founders something more useful than encouragement: a reason to change what they were building.

Interest still had to survive contact with software. Chen has described an early first version that people did not like, a second that found only one user, and a third redesigned around feedback. A waiting list could demonstrate curiosity. It could hardly fill in for a working product. The team had discovered a need, then had to learn how to serve it.

The principle behind the design was equally practical. On a phone, a page that stacks information vertically makes sense. A visitor can scroll through a story instead of navigating a collection of separate rooms. Chen saw single-page design and mobile use reinforcing each other. A smaller screen imposed limits that could make the whole experience easier to understand.

His measure of progress was time to publication. In 2018, he described an average of 15 minutes to get a site online. That figure belonged to that period, but it captures his priorities. A first-time founder or student organizer usually has a project to launch. Becoming accomplished at arranging boxes on a screen may be an unexpectedly lengthy detour.

The rejection that made the decision

Y Combinator initially turned the team down. They had been hoping acceptance would provide the assurance to commit fully. When it did not arrive, the founders had to answer the question themselves. They continued, applied again and joined the accelerator’s Winter 2013 batch.

Years later, Chen opened his advice to applicants with the uncomfortable test he had once struggled to answer: would they keep working full time if rejected? The question removes the committee from the center of the story. An accelerator can supply money, introductions and advice. It cannot make the founders want their own business enough to continue building it.

His application advice is full of useful, unromantic preparation: write clearly, show what you have built, divide speaking responsibilities and rehearse. He also recommended matching team T-shirts, while conceding that he could not prove they helped. Even a carefully argued application apparently has room for a small wardrobe theory.

“People. Always the people.”

David Chen, 2017

When the company becomes the design problem

As Strikingly grew, Chen’s work changed. Product and customers came first, then growth, then the systems that let a larger group function. Communication became a design problem of its own: information had to travel without every conversation passing through the CEO. The person who helped remove a dependency for website builders now had to avoid becoming a dependency himself.

In 2017, he described a recurring concern that the company might grow beyond his abilities. He used that concern to keep learning. This is a revealing admission from someone whose job involves supplying direction. His account leaves room for the possibility that the person running a company must change as thoroughly as the product does.

The practical questions were about hiring, matching people to work they could do well and getting teams with different responsibilities to understand a shared purpose. An engineering team and a customer-facing team do not spend their days looking at the same problems. A coherent company needs ways for them to understand one another before every disagreement becomes an appointment with the founder.

A bigger map, the same first step

The business also developed a Chinese counterpart. SXL, Strikingly’s local brand, offered website and WeChat mini-program tools for businesses moving online. Restaurants, retailers and education businesses presented different contexts for the same underlying ambition: give someone a manageable way to establish a digital presence. Expansion meant adapting the route to the customer.

In his writing about Strikingly’s mission, Chen treats publishing as a form of participation. Reading what other people make is one experience of the internet; having the means to put your own work there is another. His stated aspiration is to make that second experience more widely available. A website builder is a fairly concrete instrument for such a broad belief.

He has also emphasized customer conversations as part of product development. A question arriving through support can expose a missing feature or an assumption that has failed. The exchange carries information both ways. For a company that began by discovering users wanted something different from what its founders intended, listening is more than a pleasant customer-service habit.

The calendar after the dorm room

By November 2020, Chen said Strikingly had more than four million entrepreneur users. His description of his working day was less cinematic: an HR meeting, hiring interviews, emails, decisions and work on one or two projects he personally wanted to advance. He made room for those projects among the obligations that came with running the company.

His everyday tools included Gmail, Google Docs and Google Sheets. His recommended reading included The Hard Thing About Hard Things, Creativity, Inc., Zero to One and Winning. For all the language of entrepreneurship, much of the work looked familiar: recruit carefully, write things down, answer people and decide what deserves the next block of time.

That is the appealing continuity in Chen’s story. He began among people trying to get projects off the ground. He encountered an expensive obstacle, helped build a solution and kept revising it when users disagreed. The original crowdfunding plan did not survive. The willingness to notice what was useful did, and it gave the three friends something worth continuing to work on.