Zendesk’s CEO built an app with his son and learned AI the hard way
There’s a version of AI adoption where you read the reports, attend the briefings, and delegate implementation to your team. Tom Eggemeier, CEO of Zendesk, chose a different path. He built a real piece of software with his college-aged son, shipped it into the world, and let it break in front of him.
The project was a sports recruiting app for college basketball. Will, Tom’s son, plays at Boston College and had an idea for tooling that could help general managers work smarter. The two of them started vibe coding together, and for a while it felt straightforward.
When the Excitement Wore Off
“We were vibe coding, and it was exciting because of the cool features that were coming out,” Tom said. But the cracks appeared fast. Will noticed the AI generating recruitment suggestions that didn’t hold up to scrutiny. The speedy development cycle had created technical debt across security and API protocols. Hours of debugging followed.
Two college basketball general managers evaluated the finished app and told Will and Tom it matched roughly 70% of what’s already available commercially. That’s a useful benchmark, not a failure verdict, but it’s honest about the gap between what vibe coding produces and what the market already sells.
There’s also a practical constraint. Will is still on BC’s roster, which means he can’t sell to rival schools. The app stays in development mode until he graduates.
What Tom Took Back to Zendesk
The build changed how Tom thinks about AI at work. His takeaways are concrete enough to be worth stealing.
Use the technology yourself, personally. Tom used a personal AI agent to renegotiate his insurance coverage, internet bill, mobile plan, and subscriptions. His words: “I’m a little embarrassed to say it saved me $3,150 a year.” That’s the kind of number that recalibrates how seriously you take the tooling.
He also trained ChatGPT Work to write in his voice, then noticed it kept ignoring his instruction to avoid contractions. He had asked it to avoid them because contractions are harder for non-native English speakers to follow. The repeated failure became a lens. As he put it: “That recurring mistake has led me to think more deeply about how memory and skills affect our products and internal use of AI.”
His other guidance for CEOs:
- Keep hiring young employees. AI natives bring a fluency that creates a useful dynamic alongside experienced workers.
- Address the anxiety around AI directly, while actively helping people build skills.
- Create projects that put AI to work on real problems, not demos.
- If your kids want to build something with you, do it.
The Transferable Lesson
Will says he wants a career in sports business and believes deploying AI is essential to getting there. He credits Tom with helping him develop grit, citing “suck it up” as a guiding phrase from his father.
Tom says the project made him “a better leader for our R&D organization, our product, and AI.” That’s a high return on a few weeks of vibe coding with your kid.
For any operator running a team or building a product: the lesson isn’t that vibe coding is bad. It’s that hands-on contact with the tools, including the failures, is what actually changes how you lead. Reading about technical debt is not the same as debugging it at midnight.
I’m founder of BizStack at Cagri Sarigoz LLC and a passionate advocate for entrepreneurs.
With over 14 years in tech, marketing, and AI, including my role as Head of SEO at CitizenShipper and co-founder of TaleBot at Intale AI, I’m dedicated to sharing genuine, useful product insights and tips.
At BizStack, I aim to cut through the digital noise to provide clear, actionable advice.
And more than all else, I’m a father to a (always) little girl and a husband.
Contact me at [email protected] for assistance.
