Daniel Bernstein spent much of the past decade as an M&A advisor, selling other people’s software companies. This time the company was his own, and he found a buyer in McGraw Hill.

The education publishing giant on Wednesday announced the acquisition of Teachally, a small startup led by Bernstein in Bothell, Wash., that uses AI to help teachers build and customize lessons, assignments and assessments aligned to state standards.

Financial terms weren’t disclosed. The deal has closed, and all five employees have joined McGraw Hill, with Bernstein taking the title of senior advisor for Teachally integration and growth. He declined to say what the company sold for or how much it had raised, but said the outcome was good for him and his investors.

“We didn’t take in a pile of money,” Bernstein said, explaining that the company brought in a small group of angels and was able to stay focused and effective.

The five-person team is spread across three continents: Bernstein and a colleague in the Seattle area, co-founder and CTO Rushil Makkar in Melbourne, Australia, a customer success lead in Arizona and a developer in Ethiopia.

Bernstein is best known in Seattle tech circles for Sandlot Games, the game studio he started in a spare bedroom in Bothell in 2002 and sold to Digital Chocolate in 2011, after developing casual gaming hits including “Cake Mania” and “Tradewinds.” He later founded the mobile game startup UpTap.

Bernstein spent the following decade on the other side of deals, as a software M&A advisor at Corum Group and then at his own firm, Hemisphere Partners, which ran Teachally’s sale.

Teachally raised a small round from local angels about nine months ago, and later opted to try an M&A process. An edtech M&A specialist representing the company approached a small group of potential buyers, and Bernstein said he hit it off immediately with McGraw Hill over a shared view of what curriculum and instruction should look like in the age of AI.

Teachally focuses on teachers rather than students, developing technology for what the industry calls high-quality instructional materials, or HQIM, which is the standards-aligned curriculum that many states and districts have pushed schools to adopt.

The startup was working with about eight school districts at the time of the sale — fully commercialized, Bernstein said, but “still very much an early stage company.” It was named a top edtech product for curriculum and instruction by District Administration magazine in January.

Bernstein said he had to learn an entirely new industry after two decades in games. The M&A work helped: he’d taken other edtech companies to market before building one.

Teachally itself started as something else. The company was founded as EZ Reward, maker of EZ Stickerbook, a digital sticker chart teachers used to reward students and message parents. Bernstein pivoted the company about three years ago to focus on AI for teachers.

McGraw Hill, which went public last year and reported $2.1 billion in revenue in its most recent fiscal year, said the deal will let it develop and localize K-12 curriculum faster and put AI tools in front of teachers already using its content.

“This acquisition provides a great opportunity to accelerate our AI strategy in ways that directly support educators and strengthen how we develop and deliver our K–12 products globally,” said Jana Thompson, interim president of the company’s School group, in the announcement.

Teachally is now live as a McGraw Hill product, with its own page on the company’s site.

Bernstein said it’s a second exit both for him and for some of the angels who have backed him along the way. “It’s a good Seattle story once again,” he said.

"We raised at a peak, but sold at a fraction of that," Unacademy co-founder and CEO Gaurav Munjal wrote. "I'm not going to dress these facts up."

Seattle-based edtech startup Wild Zebra has raised $6 million to expand its AI learning platform for math and reading, citing early signs that its specialized product can hold its own against the free study tools released over the past year by OpenAI, Google and Anthropic. 

One of Wild Zebra’s secrets is its Socratic approach: rather than handing over the answer, the platform works students toward it with questions, drawing out the reasoning step by step.

Another key difference: the lessons are customized to be grounded in whatever topics or hobbies the student is already interested in, such as sports, cooking, music, or anything else.

The platform also analyzes the conversations themselves, looking not just for students who are distracted or getting answers elsewhere, but for those showing persistence or curiosity — flagging those positive moments in dashboards for teachers and parents. 

The idea is “to catch kids being good, too,” said edtech veteran Edan Shahar, the company’s CEO and co-founder.

Latest funding: The oversubscribed seed round was led by Bellevue, Wash.-based Trilogy Equity Partners, with participation from Tetherpoint Capital and angel investors including Shrikesh Majithia. It brings the company’s total funding to $8 million.

Wild Zebra, co-founded in 2024 by Shahar and longtime AI technologist Erik Selberg, serves students in grades 2 through 9. The company, with a team of 10, plans to use the new funding for hiring, primarily engineers, along with sales and marketing initiatives.

Trilogy Managing Director Amy McCullough, who is joining the Wild Zebra board, said the VC firm backed the company for its potential to give parents and teachers a real-time view of what a student has actually learned, and a path to mastering the material from there. 

She said she came to the deal as a customer first: her family had used Test Innovators, the private-school admissions test-prep company Shahar ran for nearly a decade, and she was struck by how well it delivered for parents and students at a high-stakes moment. 

“When we were introduced to Wild Zebra, we knew very quickly that this was the team who could build the student-centric AI partner for the market,” McCullough said.

Competitive landscape: When GeekWire first covered Wild Zebra last year, OpenAI and Google had just launched study modes of their own. Anthropic launched a free version of Claude for K-12 teachers last month, and Khan Academy’s Khanmigo has been in the market for years. 

Shahar said the general-purpose chatbots are good at answering a single question or explaining a concept, but don’t keep track of what a student knows over time. 

Wild Zebra builds what the company calls a “learning tree” for each student — what they’ve mastered, where the gaps are, what comes next — and uses it to decide what they work on next, rather than just responding to whatever they happen to ask.

Shahar sees the big AI labs as suppliers more than rivals. Wild Zebra runs on their models, along with others. 

Traction so far: Wild Zebra says it now reaches tens of thousands of students, up from about 6,000 a year ago, and has logged hundreds of thousands of tutoring conversations.

It opened the platform to families this year at $48 per month per child. The first consumer customers, Shahar said, were parents at pilot schools who wanted it for their other kids. 

On the school side, Wild Zebra works through E3n, formed this year by the merger of the Educational Records Bureau and the Enrollment Management Association, which serve selective private schools. ERB invested in the company in 2024. 

Many member schools test students using E3n’s exams, and Wild Zebra uses those results to set each student’s starting point, though some schools using the platform don’t. 

Early results: E3n also conducted a 722-student pilot evaluation of math and reading, measuring results against ERB norm groups collectively built from hundreds of thousands of students. It found gains of four to eight percentage points among fifth and sixth graders.

Having started in private schools, Wild Zebra is now talking with charter and public schools. 

Shahar said schools and students skeptical of AI mostly don’t become customers, and the ones who do tend to share his optimism while still taking the risks seriously. 

The concern he hears most often from students is AI’s environmental impact — which, he acknowledged, is not something Wild Zebra is working to address.

“I’m not a Pollyanna. I think there are certainly potential downsides to AI in general,” he said. “There are people working on the downside mitigation. I’m working on upside opportunity.”