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May 15, 2025 99 mins

Chris Heivly’s journey through the tech world is one for the books, literally - thanks to his deep-rooted love of maps. From his early days studying geography and computer mapping to shaping the future of internet navigation with MapQuest, Chris shares an inspiring story of innovation, risk, and community-building.

In this episode, we explore Chris’s entrepreneurial journey, discussing everything from his time building map systems for the U.S. State Department to his pivot into founding one of the Triangle’s first startup accelerators, the Triangle Startup Factory.

Tune in to hear:

  • Chris’s early fascination with maps and how it led him to become a leader in the tech space.
  • The inside story of MapQuest and its revolutionary role in the rise of online mapping, years before Google Maps.
  • The entrepreneurial lessons Chris learned while transitioning from MapQuest to venture capital.
  • Insights from running one of the first accelerators in the Triangle and how it shaped the region’s startup ecosystem.
  • Stories of standout companies from the Triangle Startup Factory, including the success of Archive Social.

Where to Find Chris Heivly:

  • LinkedIn: https://www.linkedin.com/in/chrisheivly/
  • Build the Fort Blog: https://heivly.com/blog/

Where to Find Scot Wingo:

In this episode:
(00:03:00) Chris's love of maps and how it shaped his career from geography major to tech innovator.

(00:10:15) The breakthrough moment: from computer mapping to building mapping systems for the U.S. State Department.

(00:17:45) The story of MapQuest’s creation, why it was so ahead of its time, and how it revolutionized navigation.

(00:27:30) Chris’s time at Donnelly and the strategic decisions that led to MapQuest's success.

(00:38:05) The evolution from VC to accelerator: Chris’s journey building the Triangle Startup Factory and shaping the local ecosystem.

(00:46:52) Chris’s key lessons for startup founders and how to build a lasting legacy.


In the news:

  • Going Against the Flow: Chris Heivly, Managing Director of The Startup Factory: https://www.huffpost.com/entry/going-against-the-flow-ch_b_10596620
  • One-on-one: ‘Startup Whisperer’ Chris Heivly talks Raleigh-Durham Startup Week, Triangle’s success, new book: https://wraltechwire.com/2023/04/19/one-on-one-startup-whisperer-chris-heivly-talks-raleigh-durham-startup-week-triangles-success-new-book/


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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.


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Triangle Tweener Talks is sponsored by:

  • Atomic Object: https://atomicobject.com/
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