How a History Student Turned Her Side Hustle Into a Startup That's Raised $7 Million: "People Always Tell Me, 'I Thought I Had to Major In Computer Science to Be an Entrepreneur'" Audrey Wisch never imagined she'd be one of those kids who dropped out of college to grow her side hustle into a startup. But with the help of AI, her "human-centric" service is scaling up.
By Frances Dodds Edited by Mark Klekas
Ever since ChatGPT came on the scene, people have been eulogizing certain lines of work.
Audrey Wisch had plenty of reason to be freaked out by these predictions. Her side hustle, which she'd dropped out of college to grow into a startup, was bemoaned as one of those "soon to be obsolete" jobs. And honestly, at the beginning, Wisch wanted nothing to do with AI. "I'm non-technical," she says, "I was a history major!" But she decided to push through her discomfort and started spending 15 minutes a day with the chatbot. Within a month, she says, "I was using AI in every single hour of my workday." At that point, she stopped fearing AI would be her undoing, and started seeing it as the key to scaling her human-centric services. Now, she says, "I always have people coming up to me saying, 'I thought I had to major in computer science to be an entrepreneur."
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But let's go back to the beginning, in 2020, when Wisch was an undergraduate student at Stanford. While stuck in lockdown, she started tutoring high school students remotely as a side hustle. Pretty quickly, she became aware that the kids, as they say, were not alright. They were next-level checked out and disengaged. She'd teamed up with another Stanford student, Alec Katz, to offer more tutoring subjects (she wasn't passionate about math), and together they started experimenting with less traditional — or "transactional," as Wisch describes it — tutoring. Instead of helping kids prep for next Friday's test, Wisch and Katz started teaching students about things they were passionate about. For Wisch, that was criminal justice, and for Katz, aviation. When the kids saw how passionate their not-so-much-older tutors were about these subjects, their excitement was contagious.
Ultimately, this discovery led Wisch and Katz to co-found Curious Cardinals: a near-to-peer, one-on-one virtual mentoring and tutoring service that connects kids of all ages with high-achieving college student mentors and tutors. "We felt the gravitational pull on both sides," Wisch says. "College students were looking for ways to make money or do something meaningful. And in the pandemic, parents were looking for ways to inspire their kids and mitigate learning loss. A lot of kids took gap years before college. So it totally took off."
Curious Cardinals offers two mentorship tracks. One is the "passion project" track, where students are matched with mentors who can help them learn more about subjects they're excited about. And the other is academic mentorship, where kids are matched with tutors to help them with subjects they're struggling in. "I had a local math tutor in high school," Wisch recalls, "an older guy, and it didn't make the difference. But having a female engineer mentor who was crushing it in the STEM classroom, while also bonding with me over Taylor Swift's Eras Tour — that could have made the difference."
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Even as the pandemic wound down, parents continued looking for ways to help their kids make up for lost learning. And generally, there was more dissatisfaction with traditional education. So Wisch and Katz decided to ride the momentum, and dropped out of Stanford to grow their startup.
Curious Cardinals grew fast. Soon, they had thousands of college students applying to be mentors. "This is like the best part-time job for college students," Wisch says. "The sheer talent of our mentors is phenomenal. They're Rhodes Scholars, D1 athletes, presidents of clubs."
Investors were intrigued, too. As they were fundraising, Wisch and Katz kept hearing one concern from investors: How big can this business really get? Some thought it was impossible to scale a service where the product is human beings — college students, no less — because people are so unpredictable. How do you maintain consistency?
"There are some people who fundamentally don't believe you can scale this business," Wisch says. "Because the magic is the humans, the mentors — how talented they are, how personalized the matches are — and they worry, is there a ceiling for how many extraordinarily talented people there are who could be our mentors? Humans are why this business is so inspiring, but humans are also challenging. They might have a final come up or they might have their flight delayed, and changes happen."
In late 2022, as Curious Cardinals was grappling with these issues, ChatGPT splashed into public consciousness, and Wisch and Katz were deluged with another wave of skepticism.
"I don't know if you saw the GPT 4 launch — the video of the AI tutor," Wisch says. "A lot of people are like, does that mean tutors are going to be obsolete? Does that change your business? And I'm like, no, honestly. Our thesis didn't change. One-to-one human connection is the gold standard for learning. I will never tell a group of parents that AI will inspire, engage with, or instill confidence in their kids better than humans can. Because I don't believe it ever will."
Still, Wisch forced herself to start playing around with AI — as much to prove the doubters wrong as anything else. But the more she used it, the more opportunities she saw. Not to replace the human piece, but to support and make the most of human interactions. She realized that AI just might be a solution to this whole consistency issue that was scaring off investors.
For example, every session, mentors are asked to submit an overview, noting what the student learned, progress they're making, areas for growth, what they're doing the next time, and how a parent can help.
Some mentors submitted detailed, thoughtful overviews, and others just wrote, "Good job David!" Curious Cardinals would ask the mentor to submit something more thoughtful and sometimes they would, but other times they'd delay for several days or even a week. They were busy, and often had back-to-back sessions. Some of the best in-person mentors were the worst about creating session notes, because they were the most busy. So Wisch worried the parents didn't realize how high-quality those mentorship experiences were. Then, it occurred to her that they could record sessions, and use AI to create summaries of the lesson from the transcriptions. "Suddenly a range of quality notes elevated to high quality, comprehensive excellent notes, consistently delivered across the board," she says.
Another way Curious Cardinals started using AI is with the students' end-of-year report cards. Wisch describes these as "Spotify Wrapped meets your child's school report card."
They wanted to end the year on a high note for students and parents, so they asked mentors to share a summary of what's happened over the whole year, and what will happen next. But the end of year is tough for college students, with finals and graduation and everything else. "There's just been some mentors that deliver there and some that don't," Wisch says. "So now we're using AI to deliver the first draft of an end-of-year report. It takes into account a year's worth of detail, which is more than any teacher could do. It takes session transcripts and identifies what the goal of the engagement was, summarizes the progress, areas for growth, and what you can do next time. So that's another part of our experience that we weren't able to deliver on 100 percent and now we're able to."
Finally, Curious Cardinals has figured out how helpful AI can be when it comes to passing the baton of mentorship. For kids, switching to a new tutor is hard. We've all experienced the frustration of getting a new doctor or therapist and having to start all over — and the same goes for teachers and tutors. "Moving to someone else and having them learn all my context is a big shift. That's one of the biggest problems in K-12 education," Wisch says. "The teacher spends the first three months of the year getting to know a kid, and then they go on to the next teacher. There's no onboarding, no offboarding." Now, when one mentor graduates, Curious Cardinals uses AI to get the whole download on the student and fill the new mentor in, so there's a smooth transition. "You don't have to worry about, Oh, I have to start over and tell this person about my life and my ADHD and when I lose focus," Wisch says. "We are using AI to close that context gap. Adam Grant talked about the power of having a long term mentor or teacher. So we're trying to use technology to retain that context."
Ultimately, it's all working pretty well. To date, Curious Cardinals has 12 full-time staffers, and over 500 mentors on the platform. For Wisch personally, facing down her fears about AI has only made her more certain of her startup's value. "In a world where kids are lonelier than ever and mental health is in greater crisis than ever before, what kids need most is genuine human connection," she says. "By harnessing the power of AI to support our mentors, we enable them to focus on what truly matters: building meaningful relationships."
