Brian Tobal and the unfinished book

Brian Tobal has a small problem with the question “What are you reading?” A single title would make the conversation easier. In his case, it would also give the wrong impression. When he wrote about his reading habits in 2020, the answer was usually about a dozen books at once. Somewhere, a bookmark manufacturer should be sending a thank-you note.

He called the method Surgical Reading. A book could be approached as a place to find something useful, with its index and contents supplying directions. The obligation to proceed obediently from the first page to the last could be set aside. The reader had a question. The book had material. They could conduct their business without a completion ceremony.

That makes an inviting opening to Tobal’s working life. He co-founded Hickory, a company concerned with what employees remember after training. He later led SchoolHouse, which helped families create small classrooms around teachers. Between the reading chair, the workplace and the classroom, the practical issue keeps returning: what does a person actually carry away?

An index can be a beginning

Before the companies, there was teaching. Tobal began his career teaching science and technology at Harlem Children’s Zone. Educational research followed, then work on learning software and programs for schools, universities and businesses. His route into education technology therefore included the experience of standing in front of children and trying to make a lesson work.

He also became head of academics at Flatiron School, the coding school. These are different educational settings, with different ages and expectations. A child learning science and an adult learning software development have little reason to appreciate identical instruction. Tobal’s career crossed both, giving his later work a background wider than the familiar story of a founder discovering education through an app.

His reading method offers a compact view of his priorities. He surveys a nonfiction book before committing to it, using the cover, index, contents and preface to work out where its useful ideas might be. Notes preserve that map. He can follow a topic across several books, return to a promising section or put a volume aside.

There is something pleasantly unceremonious about this. A bookshelf can impose its own social pressure: all those spines, all that unread virtue. Tobal’s approach makes room for an unfinished volume to remain useful. The relevant achievement is finding material that changes how he thinks about a problem. A book may earn another visit without earning every evening of the week.

The test comes three weeks later

Hickory brought a related concern into employee training. The company entered Y Combinator’s Summer 2015 batch, with Tobal as founder and CEO. Its intended users included sales and customer service teams, people whose knowledge has to survive the journey from a lesson to an actual conversation.

The product was designed to estimate when a learner would forget something and arrange individual review exercises. Different employees could receive different practice, depending on what they already knew. The premise placed time inside the training problem. Knowledge needed attention after the presentation ended.

Tobal explained this through an ordinary workplace scene: a representative completes training and passes a quiz, then faces an angry customer three weeks later. Would the lesson still be available? His objection was that a test immediately after instruction could capture recognition while leaving later recall unsettled. The customer would arrive on a schedule of their own.

His writing argued for tracking knowledge at the level of individual concepts. Repeating an entire course treats familiar and shaky material alike; personalized review could spend the learner’s effort more selectively. It is an economical idea, concerned with the minutes people lose reviewing what they already understand, as well as the information they lose by reviewing too little.

“move the teacher forward and make the teacher the centerpiece”

Brian Tobal on the idea behind SchoolHouse, April 2021

The chocolate comes first

For all this interest in learning systems, Tobal’s writing occasionally begins somewhere less systematic. An article about updating employee training opens with his chocolate cravings. The office made emergency trips to Whole Foods for Icelandic bars with sea salt. After that came the second recurring business problem: changing the training when a policy or product changed.

It is a good little joke because the ranking is so confidently wrong. An operational nuisance has been demoted beneath the snack supply. Then the article gets down to work. Tobal divides organizations by the size and predictability of their updates, distinguishing a steady stream of manageable changes from the more exciting experience of constant surprise.

His advice is practical. Predictable changes can be gathered into a weekly recap. Sudden changes require decisions about the few details employees must understand immediately. Temporary adjustments need an explanation of when ordinary procedures resume. The writer who lets himself skip around a book also asks managers to decide which information deserves attention first.

The chocolate detail gives the advice a human voice. It also saves the reader from a familiar business-writing ordeal, in which even a routine policy update must arrive wearing a tie. Here, the subject is allowed to remain ordinary: people have work to do, information keeps changing, and the message needs to reach them.

A smaller room, a larger question

With SchoolHouse, Tobal and co-founder Joseph Connor worked on a different arrangement for learning. Founded in 2020, the company helped families establish microschools and learning pods. Parents could gather a small group of children, find a teacher and organize a classroom in a home or other suitable space. SchoolHouse supplied support around that arrangement.

In his guide to starting a microschool, Tobal walked families through choices that could easily become a project in themselves. The group needed agreement on curriculum and structure. A location had to be chosen. SchoolHouse would provide matched teacher profiles, including recorded interviews, so families could consider teaching style alongside credentials. The classroom began taking shape before its first lesson.

These details matter to the story because they show what the company was taking on. Recruiting a teacher is one job. Helping several families agree about what they want is another. A small school still requires administration, expectations and preparation. Reducing the room’s size does not magically reduce the number of decisions to zero.

By April 2021, SchoolHouse reported about 250 students across roughly 50 locations in 10 states. It had raised $8.1 million in funding, with Pace Capital leading the round. The average class size was reported as six to ten students, though some groups were larger. These were the dimensions of the venture at that point in its development.

Tobal described the ambition as putting the teacher at the center. He said the classrooms were becoming expressions of the needs of their students. That emphasis gives the numbers their context: the proposed advantage of a smaller group was room for the teacher to respond. Expansion meant repeating the arrangement while preserving the attention that made it attractive.

There is a useful tension here for anyone building an education company. A business wants a model it can repeat. A teacher has particular children in front of them. SchoolHouse’s proposition depended on both things being possible at once. Its support work belonged around the classroom, leaving the teacher to make decisions within it.

The people between the companies

Some of Tobal’s story sits in the connections between ventures. Tiago Forte became an angel investor in SchoolHouse after a series of conversations with him. Forte’s account also pointed to Tobal’s earlier academic leadership at Flatiron. The relationship brought together two people publicly interested in learning, even as their work took different forms.

Another connection appears in Circle’s founding account. Tobal, introduced to its founders through Forte, helped them meet a handful of angel investors. An account from investor Notation likewise describes meeting Circle’s Sid Yadav through Tobal. These are modest details beside a CEO title, but they show a concrete contribution: making the next conversation possible.

Joe Burgess is another recurring collaborator. The two appeared together in a discussion about student-teacher relationships, bringing their experience in education and software into a conversation about the human part of a classroom. Burgess had been Flatiron School’s first employee and instructor. Their shared subject extended beyond getting educational material onto a screen.

Still asking the question

Tobal later joined Burgess and Sean Dagony-Clark as a co-host of Ways We Learn. Its conversations range across storytelling, games, classrooms and technology. The published episode list includes discussions of learner motivation, learning through stories and the difficulties of scaling education. The latest numbered episode listed is a November 2024 conversation with Ariel Diaz about copyright.

His current LinkedIn profile lists TasteBud and describes him as a four-time founder with three exits. The company affiliation marks another chapter in a working life that has moved through several organizations. Hickory belongs in that history as a venture he co-founded and led; its Y Combinator listing now marks the company inactive.

The unfinished book remains a useful place to leave him. It is a specific habit, with a practical purpose, and it resists the polished career story in which every chapter closes neatly before the next begins. Tobal’s public work leaves several questions open at once: what people remember, what teachers need, and what makes an idea worth returning to. There is room for another bookmark.