What does it mean to be an entrepreneur?
Holly Tachovsky’s reflections on her journey paint a vivid picture of the grit and determination required to create, innovate, and move forward—even when the path is unclear. For Holly, the end of one project is never truly an ending but a stepping stone to new beginnings. Her career, marked by transformative insights and a relentless pursuit of meaning, sheds light on how entrepreneurship is less about following a prescribed path and more about navigating complexity with grace, creativity, and courage.
When Holly began her career in government, it seemed like a logical extension of her degree in political science. Yet, as she worked in the Texas House of Representatives during pivotal national moments, she quickly discovered the slow-moving nature of government did not align with her need for dynamism. The realization that this path was not for her could have been paralyzing, but instead, it sparked an entrepreneurial spirit that would go on to define her life.
Her transition into the business world was far from straightforward. Founding a company focused on selling building department software to local governments—a sector as slow-moving as the government itself—Holly faced obstacles that tested her resolve. Yet, these challenges laid the foundation for something much greater. Out of the ashes of her first venture emerged BuildFax, a company that would revolutionize how building data was gathered and utilized.
The inception of BuildFax was anything but conventional. Holly and her team fell in love with the data—massive amounts of information about building permits across the United States. But they faced a critical error early on: they built their product without fully understanding their customer. This misstep nearly derailed the business. “We fell in love with this data source rather than falling in love with the customer.”
It was desperation that ultimately led to innovation. A pivotal moment came when Holly attended an insurance innovation conference uninvited, hoping to glean insights. There, she learned that insurance companies were desperate to understand the age of roofs—a seemingly niche detail that turned out to be a billion-dollar problem. This revelation was a turning point, reshaping BuildFax into a company capable of providing invaluable data to some of the largest insurance companies in the world.
Holly’s journey with BuildFax also highlights the emotional complexities of entrepreneurship. Selling the company, a Fortune 500 acquisition, was both a triumph and a moment of profound personal reflection. For Holly, the act of creating something is deeply tied to purpose. She describes the process of building a business as breathing life into something—a process that, when completed, can leave a sense of loss, as though part of oneself has been left behind.
In the aftermath of selling BuildFax, Holly found purpose in a new way. Rather than retreating into the comforts of her success, she leaned into the power of connection and community. She serves on the board of organizations dedicated to empowering women entrepreneurs, providing not just financial support but also mentorship and camaraderie. Her work helps women, particularly women of color, build businesses that create generational wealth and foster resilience in their communities.
At home, Holly’s commitment to service continues. She and her family cook meals monthly for a local community organization, delivering food and connection to those who may feel forgotten. These acts of service remind Holly of the shared humanity that binds us all, a sentiment that resonates deeply with her belief in the intrinsic value of every person.
Holly’s story also challenges the cultural glorification of hustle. While she acknowledges the necessity of hard work, she critiques the toxic elements of hustle culture, emphasizing the importance of obligation and commitment as pathways to purpose. For Holly, true fulfillment comes not from endless striving but from dedicating oneself to meaningful endeavors, whether in business, family, or community.
Her reflections invite us all to reconsider our definitions of success. In a world often obsessed with scale and speed, Holly’s journey reminds us that the most profound impact can come from small, consistent acts of care and connection. As she puts it, “We’re all in this together, and that can be enough.”
Holly Tachovsky’s story encourages us to embrace the complexities of our own journeys and to find joy in the process of building, connecting, and growing—whether in business, in our communities, or within ourselves.
To hear more about Holly Tachovsky’s inspiring journey tune in to her episode of Navigating Complexity.