Stay in Learning Mode | The Entrepreneurial Journey

From coding in a college basement to leading a digital studio trusted by Adobe, Gap, Stanford, and DocuSign — Ben Callahan has walked the long, messy, and exhilarating road of entrepreneurship .

He didn’t start out wanting to be a business owner. In fact, he once swore he never would. But after years of building other people’s dreams and sleeping in his office for someone else’s paycheck, Ben had a realization: if he was going to sacrifice that much, it better be for something he owned .

That decision sparked a journey that took him from scrappy startup projects (doing anything to pay the bills) to founding Sparkbox, a digital powerhouse at the cutting edge of design systems and technology. Along the way, he discovered hard-won lessons every entrepreneur needs to hear:

• Why “doing good work” isn’t enough — it’s just the cost of entry.
• How relationships and storytelling open doors to blue-chip clients.
• What it really takes to transition from practitioner to mentor and coach.
• Why his personal mantra, “Stay in Learning Mode,” might be the ultimate entrepreneurial advantage.

This episode isn’t just about websites or tech. It’s about grit, timing, reinvention, and the courage to bet on yourself. Ben brings 20+ years of experience, but more importantly, he brings perspective — and a roadmap for anyone ready to level up their own entrepreneurial journey.

"The Entrepreneurial Journey with Dave Wescott" is a weekly podcast airing LIVE at 9:15 a.m. PST on Dave's YouTube, Facebook, and LinkedIn profiles, and available ahead of your Thursday morning commute as an audio-only podcast on your favorite podcasting platform.

This podcast is proudly sponsored by WESTERN Snow Plows. Find out more at www.westernplows.com This podcast is also sponsored by Frost Solutions. Learn more at http://frostsolutions.io