Some CEOs fail because they run out of money. Others fail because they run out of humility. As Tom Chavez told me on The Scaling CEO, ego is the single biggest barrier to growth and curiosity is the cure.
Tom is the co-founder and CEO of Super{set}, a startup studio that builds data-driven companies from the ground up. Before that, he founded Rapt, which he sold to Microsoft and Krux, acquired by Salesforce. Across his ventures, Tom has generated a 17x return for investors, proof that his systematic, repeatable approach to building companies works. With degrees from Harvard and a PhD from Stanford, he’s one of the few CEOs who have mastered both engineering and philosophy and built empires from both.
Founders Don’t Wait for Perfect People
At Super{set}, Tom doesn’t look for unicorn founders. He looks for learners.
“Sometimes entrepreneurs show up ideally scrappy, a little rough-hewn… You have to have what we call demonic intensity and a willingness to go the distance. The other things are coachable.”
For CEOs, that means stop waiting for perfect conditions or perfect hires. Progress beats polish every time.
Data Isn’t Supportive. It’s Central.
Tom has built his entire career on data and decision science. But most CEOs, he says, still treat data as background noise.
“Data isn’t something to be processed. It’s the main event… Capturing, organizing, orchestrating, wrangling, moving, activating data, that’s God’s work.”
AI has only amplified that truth. CEOs who don’t understand their data will lose to those who do. Data isn’t a byproduct. It’s the product.
Go-to-Market Is Systems Engineering
Tom’s biggest scaling mistake as a first-time founder was underestimating go-to-market.
“The go-to-market of a company is its own systems engineering challenge. It’s at least as important as whatever systems engineering you do in the product.”
He learned at Salesforce that their dominance didn’t come from technical breakthroughs. It came from “virtuosity in go-to-market.” CEOs must treat sales enablement like an engineering problem: measurable, structured and relentlessly optimized.
Stop Hugging the Product
Technical founders often stay where they’re comfortable, inside the product. Tom calls this “hugging the product.”
“Stop hugging the product. Get out of the office. Go talk to customers. Put on your safari hat and wander through the jungle. Listen.”
Scaling requires leaving the comfort zone of creation for the discomfort of communication.
Ego Is the Enemy of Learning
When Glenn asked what separates CEOs who scale from those who stall, Tom didn’t hesitate.
“If I had to compress it into a single word, I would say ego. Ego is the enemy of progress. The best CEOs I’ve ever seen are like curious children learning every day.”
Ego creates certainty. Certainty kills curiosity. And curiosity, not confidence, is what fuels scale.
Experimentation Beats Perfection
When it comes to AI adoption, Tom is clear: don’t wait for ROI to justify experimentation.
“You’ve got to start conducting experiments. The symbolic power of teaching your people that we’re going to take shots, it’s huge.”
Mindset precedes method. CEOs who delay experimentation because they can’t quantify it yet will miss the window entirely.
Keep AI Grounded in Reality
Despite his deep technical background, Tom warns CEOs not to get swept up in hype.
“AI is still software. Don’t lose discipline around what problem you’re solving. If it can’t be built in a reasonable time with reasonable resources, we’ll tell you.”
The rule is simple: problem first, model second.
Final Takeaway
Tom Chavez proves that humility scales faster than ego. CEOs must leave their comfort zones, experiment relentlessly and treat every part of the business, especially go-to-market, as a system to engineer. The moment you stop learning, your company stops growing.
I’m Glenn Gow. I coach CEOs who want to scale through curiosity and clarity, not ego. On my podcast, I reveal the strategies top leaders use to grow bigger, faster and smarter.
Listen to the full episode of The Scaling CEO with Tom Chavez for a masterclass in data, humility and scaling with discipline.
