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🏔️ Think Big, Start Small 🏔️

By Drew B | Wednesday, October 26, 2022

David wipes his desk clear. He holds up his computer's camera, with recording turned on, and showcases the empty desk and absence of any cheating devices. Then he gets started on algebra problem after algebra problem. He talks out loud and explains his reasoning as he solves the Khan Academy problems effortlessly. David is taking a proctored assessment, and he's rocking it. Afterwards, he'll share this video recording (both of his room and his screen) with a set of peer reviewers who will confirm that he is not cheating.

Except David is cheating. On every question, in fact.

Below David's desk is his mom, hunched over with a tablet. She is feeding him not only the answers, but a transcript of exactly what to say so that it sounds like he knows what he's talking about.

And there I am-thousands of miles away from David and his mom-but remotely tuning in through a background Zoom call. David is discreetly screensharing his Khan Academy window so I know what problems he's being given. And I am the one typing in the correct answers and a Google Doc transcript of what he should say, which his mom is then sharing with David on the tablet beneath the desk.

It's quite clever, and all David's idea at the age of 15.

Although hard to see at first, we are cheating for a cause. This is not a real exam. Instead, we are trying to build our own system for proctored assessments, one that will not be susceptible to such cheating, and this is us stress testing that system. Folks sometimes call this whitehat testing (or ethical hacking).

While not a real exam, the stakes are still high.

It's September 2020, Schoolhouse.world is just a few months old, and as an online tutoring platform, the focus has been on learning and tutoring. Yet, as the number of volunteer tutors has grown (with many of them being just 14 or 15 years old), the need to certify these tutors in a more rigorous way has also grown. Schoolhouse will need to be not just about learning and tutoring, but also certifying who can tutor whom.

Even better if this system can be done remotely and asynchronously. That's exactly what we're building: a type of remote proctoring that validates that you yourself have gotten to a certain level of mastery in a Khan Academy unit exam.

Jim Nondorf, head of admissions at UChicago, sees this potential, too. Just a few weeks earlier, he came to our team with an offer: figure out how to reliably certify math mastery, and he'll include it as part of their undergraduate application. Getting certified on Schoolhouse won't just enable you to become a tutor; it'll also mean proving your math mastery to colleges. So much that Jim is now ready to announce this to every person on their email list.

So here we are, mid September, and just weeks away from Jim's Oct 1 announcement. From start to finish, we've had only 4 weeks.

The assessment system only works if we can prevent cheating, which is why David's whitehat testing is so important.

Fortunately, we can. As it turns out, David's fake cheating doesn't work.

As we skim through the recording of David's video, it's clear that David is looking at another screen. Another giveaway for reviewers are his frequent pauses while he waits for me to type what to say, making it clear he doesn't understand the underlying math.

Essential to this system are the verbal explanations David must give while solving the problems. It's hard to fake this-especially when the recording will be forever linked to one's portfolio and college applications. The evidence is there for others to see.

The Oct 1 launch occurs, void of any cheating, and we sigh in relief as everything goes smoothly. Jim takes a moment to thank the ragtag team of volunteers that built this robust system in the span of 4 weeks. No one knows it yet, but two of those volunteers will go on to become a UChicago student themselves-after certifying on the platform they helped build.


Every project has humble beginnings. What made this one unique was the sheer potential we all saw from Day 1, and the way Schoolhouse volunteers like David leaned in to make it a reality. We were thinking big, yet starting small.

We were not just building a one-off system that might work for a few hundred tutors. No, we were thinking ahead to the potential of a free, mastery-based certification system that could work at scale - not only at Schoolhouse, but also in partnership with university admission offices, thus driving a powerful incentive for high schoolers to tutor on Schoolhouse.

Yet, we started small. Volunteers, including David, Emi, Arnav, Varun, Raymond, Akshat, Sejal, Kareena, Kevin, Ada, and James (almost all high schoolers), got their hands dirty. They experimented with everything from oral exams to tiered levels of mastery. Most ideas were eliminated. But with each new experiment, new ideas emerged and momentum grew.

Few questioned the audacity of the goal-a free, mastery-based certification system-which is surprising for a few volunteers launching a new system for thousands of people, in just a month. Not to mention the stakes for UChicago in entrusting us to execute.

What these volunteers focused on was much simpler: How can we get started?

This certification system, with its humble beginnings, now forms the backbone of our platform. Every tutor on Schoolhouse certifies their mastery by recording a video of themselves completing Khan Academy problems while explaining their reasoning out loud. This video is then reviewed by 2–3 peer reviewers, who check for cheating. Cheating is incredibly rare, but just like with David, we have robust systems for catching it.

UChicago is also not the only school that recognizes these certifications. They have since been joined by MIT, Case Western, Georgia Tech, Florida State University, and WashU. Tutors like Karen J can highlight both their certifications and their tutoring on their Schoolhouse portfolios, which these universities now ask for as a question on their undergraduate applications.

I often look back to the early days of Schoolhouse with a tint of nostalgia. The volunteers that built certifications made up a dream team.

Yet, I am then reminded of the numerous ways in which Schoolhouse volunteers and product team members regularly embody this core value of Think Big, Start Small.

It seems that each month we are confronted with yet another monumental task. And we'll often find one or two high schooler volunteers paving the way.

Those early days of the certification team set the stage for what has been repeated dozens of times: our special ops volunteer team developing a curriculum from scratch for the SAT bootcamps; our engineer Anees building group messaging for our website over a weekend; volunteers prototyping a new series format of tutoring when all we had were one-off sessions, eventually leading our product team to incorporate this as a core feature; and many more examples.

Think Big, Start Small is about approaching things with creativity and an open-mindedness-what some may call naïveté. You don't need to make something perfect the first time you try. Instead, you iterate and learn from experience.

Even a first-time tutor about to host their first tutoring session on Schoolhouse must think this way: Let me get started, see how this goes, get some feedback, slowly start to improve, and eventually I too will leave my mark on this world through my tutoring impact on others. Perhaps I'll even grow a tutor tree.

Many organizations like to think big. Others like to start small and iterate.

At Schoolhouse, we do them together, every day.



Thank you to Maya, Ishani, David, and Jim for providing feedback on this post.

Written by Drew Bent, COO of schoolhouse.world. [email protected]

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