Jason Kafer
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Jason Kafer is a serial entrepreneur, payments executive, and technology builder with more than 30 years of experience creating companies from the ground up. He started his first business at age 14 repairing computers out of his parents’ basement and went on to build a bootstrapped software and payments company that was acquired in 2012, followed by a second payments company that sold in 2022 for $24 million. His career has been defined by challenging conventional industry thinking, solving complex problems, and repeatedly proving that the ability to start over, adapt, and execute is one of an entrepreneur’s greatest advantages.
Today, Jason operates a portfolio of ventures including Payments Toolbox, a payments technology platform for software companies; Payments Therapist, a consulting firm serving banks, processors, ISVs, and SaaS platforms; GiveTech, a fundraising technology platform for nonprofits; CentsChat, a payments-focused media and podcast platform; and Finopoly, a fintech investment initiative. Known for translating complicated technology and payments concepts into practical business strategies, Jason combines grassroots sales, relationship-building, and first-principles problem solving with modern technology and AI to build businesses differently from the traditional industry playbook.
IN THIS EPISODE YOU’LL LEARN:
- That starting over is a skill you can build by adapting, rebuilding, and creating value after circumstances change.
- How adversity can become an advantage by forcing creativity and opening opportunities you would not have pursued otherwise.
- Why resourcefulness matters more than resources when money, technology, staff, infrastructure, and familiar tools are stripped away.
- That sales is one of the most transferable entrepreneurial skills for raising money, recruiting teams, and negotiating partnerships.
- Why you should question industry playbooks and work from first principles instead of automatically copying competitors or established practices.
- How technology should amplify human ability rather than replace grassroots sales, relationships, communication, and customer understanding.
- Why leadership becomes visible when the plan breaks and you must make decisions quickly.
- That you do not have to fit the traditional entrepreneur mold to build successful companies.
- Why execution beats perfect planning when you act, learn from results, and adjust quickly without waiting for certainty.
- That success is not the finish line, especially when you can still prove you can create something from nothing again.
about the show
Building a successful business requires creativity, adaptability, sales ability, and the determination to find opportunities anywhere — the exact qualities tested inside Business Race. The series follows entrepreneurs as they begin the race in Key West with no money and only a laptop, forcing them to create income, solve problems, and make strategic decisions from the ground up.
Business Race is a premium reality competition series that combines entrepreneurship with an adventure-driven challenge. Contestants must work their way north through Florida, completing business challenges and generating revenue at each checkpoint to unlock transportation, accommodation, and access to the next stage of the race.
The series takes viewers inside the real experience of entrepreneurs building from nothing. Through strategy, sales, creativity, and competitive decision-making, contestants must survive each challenge and prove they have what it takes to make it from the bottom of Florida to the top.
