Triangle Tweener Talks

Triangle Tweener Talks Trailer Bonus Episode 13 Season 1

Richard Holcomb: Using "Hillbilly Negotiating" to Create an Excel-lent Microsoft Deal

Richard Holcomb: Using "Hillbilly Negotiating" to Create an Excel-lent Microsoft DealRichard Holcomb: Using "Hillbilly Negotiating" to Create an Excel-lent Microsoft Deal

00:00
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

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

------
Triangle Tweener Talks is sponsored by:
  • Atomic Object: https://atomicobject.com/

What is Triangle Tweener Talks?

Why is Tweener Madness taking over Triangle Tweener Talks? Visit https://www.tweenermadness.com to find out!

A podcast for builders by builders in the Triangle. We explore the startup journey and stories with local Triangle founders, from the idea to the exit and everything in between. Hosted by serial entrepreneur and founder of the Triangle Tweener Fund Scot Wingo, and produced by Earfluence.