Four teenage friends decide to build the world’s first Windows-based email program—and then go on to launch a second venture that scores a legendary dot-com outcome.

In this episode of Triangle Tweener Talks, host Scot Wingo sits down with Chris Evans, co-founder of DaVinci Systems (founded in 1985!) and Accipiter, to uncover the wild backstory behind pioneering email software, negotiating with Microsoft, and navigating the frenzied dot-com bubble.

Chris shares personal lessons from youth, success, and heartbreak—including how he found his entrepreneurial tribe at Enloe High School, got “fired” by his best friend at age 27, and figured out that choosing the right market timing can change everything.

Tune in to hear:

• Teenage Startup Roots. How meeting future co-founders on a school bus led to DaVinci Systems.
• DaVinci’s Email Revolution. Building the first GUI email for Windows—and why Microsoft featured them.
• Being Bought vs. Going Public. Lessons from turning down acquisition offers and facing Microsoft’s “friendly” competition.
• Personal Ups & Downs. Chris’s 1992 “firing” by best friend and CEO, and how it reshaped his outlook.
• Accipiter & the Dot-Com Boom. Shifting from publishing tech to ad-server SaaS and meeting the right investors.
• Epic CMGI Deal. The exit that turned a 25K check into 1 million and made everyone in the Triangle take notice.

Where to Find Chris Evans:

• Linkedin: https://www.linkedin.com/in/chrisevans3/

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] From High School to DaVinci

[00:05:03] Building First Windows Mail

[00:14:00] Turning Down Big Buyers

[00:26:00] DaVinci’s Missed Exits

[00:32:00] Fired by a Friend

[00:42:22] Accipiter Launch

[00:53:08] The CMGI Deal

[01:02:00] Key Lessons Learned

In the news:

• Interview with Chris Evans: the man who created email and online advertising: https://www.netimperative.com/2021/01/08/interview-with-chris-evans-the-man-who-created-email-and-online-advertising/

---
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/