John Williamson describes himself as a serial entrepreneur striving to inspire and invest in Chicago’s startup community for the last two decades. “My whole life, not just my time with Songfinch, has always been driven by passion, and I can find it just about anywhere — almost to a fault,” he said.
As the co-founder and chief executive officer of Songfinch, Williamson has spent his career transforming the way people connect through music.
At its core, Songfinch is an artist-first music platform that empowers independent musicians by providing them with meaningful financial opportunities. Williamson’s vision has created a curated community of over 1,200 talented artists who craft original, studio-quality songs inspired by customers’ personal experiences. These artists, many of whom have Grammy credits or have competed on shows like “The Voice” and “American Idol,” have collectively earned over $40 million through Songfinch.
“For me, the impact lies in the relationships built, the milestones achieved, and the lessons learned along the way—both for the artists and for myself,” Williamson said.
Under Williamson’s guidance, Songfinch has been recognized by the Inc. 5000 as one of the fastest-growing consumer product companies in the nation for three consecutive years.
Williamson’s leadership philosophy is rooted in a balance of growth, innovation and sustainability. Over the past year, he has pivoted Songfinch from a “growth at all costs” mindset to one focused on efficiency and long-term impact. This shift has led to a multi-million-dollar improvement in contribution margin, positioning the company for a sustainable future.
Beyond Songfinch, Williamson is a passionate advocate for Chicago’s startup ecosystem. He has founded and exited multiple companies, including a creative agency and a music licensing marketplace acquired by a Fortune 100 company. He is also a co-founder of Off Center Ventures, a venture capital firm supporting early-stage startups at the intersection of technology and entertainment.
“Over the past 12 months, we’ve invested $500,000 into a dozen companies, several of which were started by young entrepreneurs from underrepresented backgrounds,” said Williamson. “Beyond the financial investment, I’ve committed my time to mentoring and advising these founders, dedicating several hours weekly to help them navigate the complexities of building a business. For me, success isn’t just about the 3x increase we’ve seen for some valuations in this short period of time; instead, I measure impact by the meaningful connections we build.”
A two-time Titan 100, Williamson said the recognition has further solidified his commitment to leadership and innovation. “This platform has strengthened my network and provided a sense of camaraderie with fellow leaders who understand the unique challenges of leadership,” he said.