The founder who turned the empty chair into a company
Shawn Shivdat grew up around his mother's practice, trained as a neuroscientist, then built Penciled - an AI that quietly fills the appointment slots most clinics write off as lost.
The most expensive sound in a physical therapy clinic is silence. It is the phone that does not ring back, the reminder that never lands, the 2 p.m. slot that opens at 1:45 and stays open because nobody had time to work the waitlist. Multiply that by a few slots a day, across a small practice trying to make payroll, and the number gets serious fast. Shawn Shivdat has been listening to that silence his whole life.
He grew up around his mother's private practice, close enough to the front desk to understand the part of healthcare that never makes the brochure - the scheduling, the confirmations, the awkward calls chasing a cancellation. Years later, that early view would turn into a company. But first he took the long way around.
The long way inFrom the brain to the front desk
Shivdat studied computational neuroscience at Harvard, which is not the resume line you expect from someone who ends up automating appointment reminders. While there, he built patient-outcome prediction software at Massachusetts General Hospital - the kind of work that lives at the intersection of data, medicine, and the very human question of what happens to a patient next.
Before Penciled, he stacked up a set of experiences that look scattered until you notice the pattern. He built and launched a jobs board product at a health tech startup. He founded a global education nonprofit aimed at Caribbean students facing high-stakes secondary-school entrance exams - the students most likely to be left behind by a system that was not built for them. Neuroscience, a hospital, a jobs board, a nonprofit. The through-line is simple: find the people doing overlooked work, or getting overlooked, and build them a tool.
That sentence, which he wrote for the Penciled blog in early 2025, is more than a marketing line. It is basically his worldview compressed into ten words. Small clinics spend real money attracting patients, then lose a chunk of it to no-shows and cancellations they cannot see clearly enough to fix. If you cannot measure the leak, you cannot patch it. He watched that dynamic up close long before he had a company name for it.
The ideaWhat Penciled actually does
Penciled, founded in 2022 and part of Y Combinator's Winter 2024 batch, is an AI front office assistant for physical therapy clinics. In plain terms: it does the administrative grind that eats clinician time. It schedules out plans of care, tracks the visit frequency a patient was actually prescribed, sends reminders, handles last-minute cancellations, and fills the openings through an automated waitlist. The AI scheduling assistant even has a name - Nicole - which is a very Shivdat move, giving the boring machinery a friendly face.
The clever part is what Penciled chose not to do. It did not try to rip out the software clinics already run on. Instead it plugs directly into existing systems like WebPT, so a practice does not have to replace its stack to get the benefit. For a founder trying to spread a product across dozens of independent clinics, that decision - build on top, do not fight - is the whole game.
When it is fully deployed, the results are the kind clinic owners repeat to each other. Penciled's AI fills roughly 79% of the cancellations it detects, and it takes about three minutes on average to fill an appointment - the window between a slot opening and a patient texting back "yes." One practice reported a 35X return on cancellation automation. Others point to double-digit gains in visits and steep drops in inbound calls. The pitch, as one WebPT-using owner put it, becomes almost blunt: "If you are on WebPT, this is a no-brainer."
The buildA small team, a big grind
Penciled runs lean out of San Francisco - a small team booking thousands of appointments a month on behalf of therapists who never see the machinery working in the background. The company raised over $2.6M from Y Combinator, Initialized Capital, and a group of healthcare founders including Derek Lo and George Hadjigeorgiou, the kind of backers who have already lived the problem of selling software into clinics.
Reflecting on the YC W24 batch, Shivdat has described the experience in the plain, slightly stunned language founders use when a few months compress into what feels like a few years. The batch was, in his words, insane - the good kind. It is the tone of someone who spent a long time on unglamorous problems and finally found a room full of people who take those problems seriously.
The characterWhy the boring problem
There is a version of the founder story where the neuroscientist chases the flashiest AI problem available - a model that writes, paints, or reasons its way onto a conference stage. Shivdat went the other direction and aimed the same technology at a physical therapy clinic's waitlist. It is a deliberate choice, and it says something about how he thinks. The boring problems tend to have the biggest, most stubborn bills attached, and almost nobody wants to do the unglamorous engineering to solve them.
You can trace a straight line from the kid watching his mother's front desk to the CEO shipping software that works that same front desk at scale. The nonprofit for overlooked students, the hospital software for patients at a fork in their care, the AI for clinics losing revenue they cannot see - it is one instinct, expressed three different ways. Build the tool that gives overlooked work its due.
What is next reads like the natural extension of everything before it. Penciled started with physical therapy and the systems clinics already use, but the underlying idea - automate the administrative burden so clinicians can focus on care - is not specific to any one corner of medicine. The empty chair problem exists everywhere someone has to book, remind, and rebook a human being. Shivdat has spent his whole life learning to hear that particular silence. He is now building the thing that answers it.