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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:
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
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:
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