What happens when you grow up on a tobacco farm in rural North Carolina, turn down a million-dollar offer from Microsoft, and then build multiple groundbreaking software companies?

In this episode of Triangle Tweener Talks, host Scot Wingo sits down with Richard Holcomb—serial founder, mentor, investor, and a driving force in the Triangle’s tech scene.

Richard recounts his early days in Whiteville, NC, shares the backstory of his game-changing Microsoft Excel royalty deal (yes, it’s taught at Microsoft as a cautionary tale!), and reveals how he built and exited startups like DataDirect, HAHT Software, and StrikeIron—right through the dot-com booms and busts. 

From organic farming to “hillbilly negotiation,” Richard’s story is a fascinating blend of life lessons, tactical advice, and big-picture trends shaping the future of tech M&A.

Tune in to hear:

• Why Richard turned down a lump-sum Microsoft buyout and got monthly royalties instead.
• The rise and fall of early Triangle startups—from mainframe code to dot-com mania.
• How he used “hillbilly negotiation” to outmaneuver corporate giants in high-stakes deals.
• Why paying it forward is so important and how Richard became a mentor and angel investor for dozens of Triangle founders.
• The secrets of M&A success in today’s market and why “Rule of 40” matters more than ever.
• Life after software—including Richard’s two-decade stint as an organic farmer and restaurateur.

Where to Find Richard Holcomb:

• Linkedin: https://www.linkedin.com/in/richard-holcomb-b427a/
• North Carolina Venture Capital Fund: https://www.ncvcf.com/
• Corum Mergers and Acquisitions: https://www.corumgroup.com/

Where to Find Scot Wingo:

• Linkedin: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:

[00:00:03] Farm to Tech
[00:05:03] Early Developer Tools
[00:14:00] Hillbilly Negotiation
[00:18:06] Turning Down Microsoft
[00:26:00] Excel Royalty Windfall
[00:31:20] HAHT, Dot-Com Crash
[00:42:00] StrikeIron and Web Services
[00:47:00] Farm Life Experiment
[00:54:00] M&A, Consolidation Wave

In the news:

• Confessions of a serial entrepreneur: https://www.bizjournals.com/triangle/inno/stories/inno-insights/2021/09/14/confessions-of-a-serial-entrepreneur.html
• Farmer to table: Tales and recipes from a fiercely local kitchen: https://www.newsobserver.com/living/food-drink/article172064357.html
• Fresh Direction: A Farm-to-Table Restaurant (Published 2010): https://www.nytimes.com/2010/04/25/magazine/25food-t.html

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

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Triangle Tweener Talks is sponsored by:

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