In episode 12 of Turning Pro, Andrew Rea, the founder of Taxwire, shared his inspiring entrepreneurial journey, insights into building a startup, and reflections on authenticity in business.
From growing up in a religious household to founding Taxwire, Andrew’s experiences offer valuable lessons for anyone navigating the challenges of entrepreneurship.
Andrew Rea’s story begins in Ohio, where he was homeschooled in a deeply religious environment. Raised in a strict Independent Fundamental Baptist household, Andrew distanced himself from the religion but held on to the work ethic instilled in him from a young age. Leaving home at 17, he started working multiple jobs, ranging from construction to grocery deliveries, saving money for college and exposing himself to different perspectives.
This early exposure to the real world, especially outside of his sheltered upbringing, helped Andrew realize that there were many different ways to view life. These experiences not only broadened his mindset but also shaped his path towards entrepreneurship, eventually leading him into the tech industry.
Taxwire was born out of Andrew's deep understanding of the complexities surrounding sales tax compliance, especially for ecommerce and software companies operating across multiple states and countries. The business focuses on simplifying these intricate processes for its clients, helping them manage regulatory requirements seamlessly.
Andrew emphasizes the importance of assembling a strong, capable team. Taxwire’s head of tax, a recognized expert in the field, was hired because Andrew values top talent. As he puts it, “Always spend more to get the best.” By investing in skilled professionals, he believes that startups can accomplish more with fewer people, ensuring both quality and efficiency.
Andrew’s marketing insights are especially valuable for startups navigating the tech space. A notable example from his past ventures is the viral success of New York Tech Week, a grassroots effort that exploded with the right combination of hustle and cultural relevance. Andrew emphasizes that successful marketing isn’t just about luck—although that plays a role—but also about understanding the culture you're operating in and creating content that resonates.
Andrew also points out that many B2B companies struggle with marketing, often relying too heavily on traditional strategies that fail to capture attention. His advice is to hire people who understand culture, not just traditional marketing techniques, and to focus on creating content that reflects taste and authenticity.
One of the central themes of Andrew’s entrepreneurial philosophy is the power of authenticity. He believes that being open and vulnerable about one's journey is crucial for building trust, both in personal relationships and in business. For Andrew, sharing his background, which lacks the traditional markers of success like elite education or influential family connections, has been a source of strength.
By embracing his unique story, he has been able to connect with investors, partners, and customers on a deeper level. “The more I leaned into being myself, the more people resonated with my writing,” says Rea. He encourages other founders to be unafraid of sharing their true selves, as authenticity fosters trust and builds lasting relationships.
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