Good morning. Zendesk CEO Tom Eggemeier says he’s been telling his kids since 2023 that AI will be “bigger than the printing press, the internet, the Industrial Revolution,” and that they’d fall behind without it. Earlier this year, his son Will, a Boston College senior and basketball player who’s majoring in history with a minor in business, called his bluff. Will suggested they work together on a predictive analytics app to help college athletics programs find players in the NCAA transfer portal before richer schools do. “We wanted to create something that might be able to level that playing field a little bit,” Will told me during a recent interview alongside his dad. Tom helped design the interface, and they named it Underdog AI.
At first, everything was easy. “We were vibe coding, and it was exciting because of the cool features that were coming out,” Tom said. But Will knew something was off when the AI made recruitment suggestions that didn’t sound right. Speedy development created technical debt in areas from security to API protocols, and hours of debugging that reinforced that there are no shortcuts to making software seamless and secure. Two college basketball general managers told them the app matched about 70% of what’s already for sale; Will also can’t sell to rival schools while he’s on BC’s roster, so he’s tweaking the project until he graduates.
Will says he loved seeing his father work through problems in real time. He’s hoping to build a career in the sports business and believes knowing how to deploy AI is essential to success. He credits his dad with helping him develop grit, citing “suck it up” as a favorite line.
Tom gained as much or more from the experience, saying it made him “a better leader for our R&D organization, our product, and AI.” The experience changed how Tom thinks about AI, from investing heavily in employees’ AI skills to focusing on how AI agents help people cut expenses, time, complexity, or solve other real-world problems.
Some lessons he’d share with other CEOs?
Use the technology yourself. Tom used a personal agent to renegotiate his insurance coverage, internet bill, mobile plan, and subscriptions, and says he’s “a little embarrassed to say it saved me $3,150 a year.” Having trained ChatGPT Work to write in his voice, he noticed that it kept ignoring his instructions to avoid contractions, which he thinks are harder for non-native English speakers to understand. “That recurring mistake has led me to think more deeply about how memory and skills affect our products and internal use of AI.”
Also, keep hiring young employees; AI natives bring a fluency that creates an interesting dynamic alongside experienced workers. Understand the anxiety around AI while helping people gain skills. Create projects that put AI to work on real problems. And if your kids want to build something with you, do it.
Contact CEO Daily via Diane Brady at diane.brady@fortune.com
Top leadership news
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Wall Street banks brace for ‘political theater’
The giant blue wave that swept Congress last week has left Democrats in a celebratory mood. The vibe on Wall Street, however, is less upbeat as lawmakers like Sen. Elizabeth Warren (D-Mass.), who has expressed hostility towards the financial industry, prepare to wield oversight power. But it’s likely to amount to little more than “political theater” and public shaming—at least for now.
Meet the one town that voted for data centers
In a midterm election punctuated by America’s distaste for data centers, one small town in North Dakota bucked the trend. Of the 45 ballot measures on data centers this past election, only one went the pro-data center way. That initiative belonged to Harwood, 10 miles from Fargo and home to about 940 people, which overwhelmingly voted against a ballot measure that would place limitations on large-scale industrial developments such as data centers.
The markets
S&P 500 futures are up 0.38% this morning. The last session closed up 0.31%. The STOXX Europe 600 was up 0.63% in early trading. The U.K.’s FTSE 100 was up 0.58% in early trading. Japan’s Nikkei 225 was up 2.33%. South Korea’s KOSPI was down 0.81%. China’s CSI 300 was up 0.05%. Hong Kong’s Hang Seng was down 0.13%. India’s NIFTY 50 was up 0.23%. Bitcoin is down at $74k.
Around the watercooler
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Unrest in France looks like a ‘pretty big foreshadowing’ to economists nervously eyeing national debt at 126% of GDP by Eleanor Pringle
Republicans saw Indian Americans as ‘natural conservative voters.’ But Trump’s second term undid the gains as their support for Democrats shot up by Mia Osmonbekov
CEO Initiative Insights
“Popular music is an emotional bookmark for all of us. You have the songs that you grew up with; they define a time, a place, a memory, an emotion, and that’s with you for life. It is conceivable that [AI platforms] will start to recommend music that they have generated and they own, or nobody owns that is generated with AI, and over many years, probably several decades, young people and people not yet born will come to develop their emotional bookmarks to music that is owned by the platform or owned by no one. So I think it’s really important for the music industry writ large to do everything in their power to not enable platforms to actually be able to own music.” – Jason Peterson, Chairman & CEO, GoDigital, a media and technology company.
This month, we welcome new CEO Initiative members: Altria Group’s Sal Mancuso, Kristen Sieffert of Finance of America, Vantor’s Dan Smoot, Matt Calkins of Appian, Matthew Pine of Xylem, Padraig McDonnell of Agilent Technologies, Snehal Antani of Horizon3, and Michael Riedl of Team Internet Group PLC
CEO Daily is curated and edited by Joseph Abrams, Jason Ma, Claire Zillman, and Lee Clifford.
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