In the latest Founder's Shares podcast episode, I talked to Chris Heivly, a serial entrepreneur, investor, and startup expert, about his entrepreneurial journey, from co-founding MapQuest and The Startup Factory, to writing his book “Build The Fort.”

Chris discussed the 1996 launch of MapQuest in Lancaster, Pennsylvania, and how the innovative company was one of the first major internet mapping services. A team of 50 cartographers and map enthusiasts transformed paper maps into a digital platform, revolutionizing navigation. "Think of it as Google Maps before Google Maps," Heivly explained.

From there, Heivly discussed how his move from a traditional career to entrepreneurship was driven by curiosity and a desire to innovate, with an emphasis on why those two characteristics are crucial for entrepreneurs who are looking to start companies and build communities.

With a background in geography and experience with the US State Department, he approached problem-solving and technology applications uniquely, helping his team build MapQuest despite lacking initial business knowledge. Heivly also recalled how facing these challenges allowed him to learn that adaptability and on-the-go learning were crucial, as his team’s first meetings in Silicon Valley required them to quickly adjust to the casual tech culture.

Heivly went on to share tips on how Founders can develop confidence, recalling that his confidence came from understanding the startup process rather than self-belief. "I'm confident that I understand the process about how to get something off the ground and that gets easier the more you do it, right? Like a muscle…I know how to get a group of people to do things together," he said. This collaborative mindset helped establish credibility and partnerships with major tech companies like Apple.

He then expounded on his transition into venture capitalism and emphasized the importance of adaptability, collaboration, and continuous learning in all forms of entrepreneurship. Those tenets led him to want to help other entrepreneurs with his book, Build the Fort, and foster his own startup communities. “Why is it fun? Well, you get to now see your impact across lots of different people and you get to see and maybe help them on their journey. And, you know that's when investing does right,” he reflected.

Heivly's story is a testament to the power of curiosity, community, technology, and determination. For more inspiring insights, tune into the Founder's Shares podcast.