This story comes from my conversation with Ben Callahan on The Entrepreneurial Journey Podcast.
Ben Callahan didn’t set out to be an entrepreneur.
In fact, in college, he walked past a flyer for the Young Entrepreneurs Club and thought to himself: “I never want to own a business. That sounds like an absolute headache.”
He had seen his parents grind to keep a private practice alive, drowning in paperwork and late nights. That didn’t look like freedom.
And yet, years later, Ben was sleeping in his office, writing code for someone else’s company, realizing he was sacrificing his life for a paycheck. No equity. No ownership. No legacy.
That was the breaking point.
He launched his own shop, scrappy and unpolished at first—doing anything that paid the bills. Video work. Trade show booths. Websites for $500 that quickly turned into $1,000, then $2,000, then $4,000.
By 2009, as the iPhone transformed the web, Ben and his partners rebranded as Sparkbox. It was perfect timing—responsive web design was exploding. Today, Sparkbox has worked with Adobe, Gap, Stanford, and DocuSign.
The Wake-Up Call
Ben thought for years that if he just mastered his craft, the clients would line up.
But reality set in fast.
He told me, “Doing good work is just the cost of entry.”
Excellence wasn’t enough. Every agency that survives does good work. What separated Sparkbox was how Ben shared what he was learning—through writing, speaking, and building community. That generosity created relationships. And those relationships opened the doors to blue-chip clients.
Stay in Learning Mode
If there’s one thread that runs through Ben’s journey, it’s this: curiosity.
His personal motto—Stay in Learning Mode—is taped to his desk. He lives it through The Question, a weekly research and community project where he brings design system practitioners together to learn from each other instead of competing.
That posture of curiosity, not ego, has kept him relevant for more than 20 years in a field that reinvents itself every 18 months.
And now, as Ben transitions from practitioner to mentor, he sees himself climbing what he calls the “second mountain”—a stage not just about execution, but about teaching, coaching, and building bridges for the next generation.
What We Can Learn
- Excellence is the baseline. Don’t confuse “doing good work” with building a sustainable business.
- Relationships drive opportunity. Clients come from trust, not just a polished portfolio.
- Curiosity beats ego. The leaders who last are the ones who keep learning.
- Generosity creates growth. Share what you know—someone else needs it.
Final Word
Ben told me if he could put one phrase on a billboard, it would be this: Stay in Learning Mode.
Good work may get you through the door. But curiosity—and the relationships it creates—is what keeps you in the game.
So let me ask you:
Where in your business are you treating “good work” like the finish line, when it’s really just the starting point?
You can watch the full episode here:
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