Triangle Tweener Talks

By: Triangle Tweener Fund
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  • Summary

  • 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.
    2024 Triangle Tweener Fund
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Episodes
  • Chris Evans: 80s Founder, 40yrs of Davinci (1st Windows Email) and Accipiter Unicorn Exit

    Chris Evans: 80s Founder, 40yrs of Davinci (1st Windows Email) and Accipiter Unicorn Exit
    Jan 23 2025

    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/


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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/
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    1 hr and 31 mins
  • Richard Holcomb: Using "Hillbilly Negotiating" to Create an Excel-lent Microsoft Deal

    Richard Holcomb: Using "Hillbilly Negotiating" to Create an Excel-lent Microsoft Deal
    Jan 16 2025

    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/
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    1 hr and 19 mins
  • Todd Olson, CEO of Pendo: Pendo Founding story and What Makes Him Tick?

    Todd Olson, CEO of Pendo: Pendo Founding story and What Makes Him Tick?
    Jan 9 2025
    What drives someone to leave a cushy corporate role, start (and sometimes stumble at) multiple tech ventures, and finally build one of the Triangle’s most iconic unicorns? On this episode of Triangle Tweener Talks, we sit down with Todd Olson, Founder and CEO of Pendo—a leading product analytics platform now powering hundreds of the world’s top software experiences.Todd pulls back the curtain on his early days coding in a bank at age 14, his near-miss exits that fueled an enduring chip on his shoulder, and how he and his co-founders built Pendo into a 900-person juggernaut. Along the way, Todd dives into the heart of “Founder Mode,” evolving your culture (when everyone’s giving you a million reasons not to), and why relentless customer focus might just be the ultimate growth hack.Tune in to hear:Todd’s Unlikely Start in Tech: How a 14-year-old data-entry temp turned into a Unix-wielding problem solver at a major bank.Roller-Coaster Beginnings: The heartbreak of Todd’s first ventures, what went wrong—and why he kept going.Building Pendo from Scratch: The aha moment that sparked a mission to help software companies measure adoption and drive true customer value.Scaling to 900+ People: How Todd keeps the magic of a small startup culture alive while serving a global enterprise customer base.Customer-Obsessed Leadership: Why Todd personally calls customers with less-than-stellar feedback and how it’s created a near-cult following among Pendo users.Founder Mode & Culture Shifts: Hear Todd’s take on revamping core values mid-flight, returning to in-person collaboration, and leaning in on product.Raising Capital vs. Growing the Pie: Practical wisdom on why picking the right investors (and not sweating ownership percentages) is a path to real success.Where to Find Todd Olson:Linkedin: https://www.linkedin.com/in/toddaolson/Pendo: https://www.pendo.io/X: https://x.com/tolsonWhere to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn this episode:[00:05:03] Ringing the Gong & Celebrating DealsTodd shares a big customer win, the excitement around “gong moments,” and why team collaboration fuels success.[00:07:48] Bank Life at 14: Todd’s Early Tech OriginsHear how Todd’s mom bragged to the right person at the right time, launching him into a data-entry job turned accidental programming career.[00:12:55] First Startup Heartbreak: CerebellumTodd recounts his early venture, the near-miss acquisition, and the board drama that ultimately shaped his “chip on the shoulder.”[00:18:06] TogetherSoft & 250 Engineers in RussiaManaging a global dev team while hopping planes monthly—Todd explains the pressure cooker that taught him real product management.[00:25:45] M&A Lessons at Borland & Working with Frank SlootmanTodd gets a front-row seat to high-powered leadership under a now-legendary CEO and learns what high growth really looks like.[00:31:20] Sixth Sense & the 2008 CrunchDiving into Todd’s second startup, nearly running out of money, and how radical transparency pulled the team together at the eleventh hour.[00:39:10] Rally Software’s IPO & the Enduring ChipWriting parts of the S-1, standing on the NYSE balcony—yet realizing it wasn’t truly his company, pushing Todd to keep going.[00:44:45] Founding Pendo & Picking Co-FoundersWhy Todd returned to Raleigh for his next venture, how the early Pendo crew came together, and the story behind the name.[00:52:15] Choosing the Right InvestorsTodd recalls how a single “yes” check started the seed round—but why aligning with good humans is even more critical than a big valuation.[01:05:05] The Power of Customer ObsessionFrom personal phone calls to instant problem solving, Todd reveals why old-school “MBNA-style” service still wins hearts in SaaS.[01:08:10] Entering ‘Founder Mode’ & Betting on AITodd opens up about reinvigorating Pendo’s culture post-COVID, re-committing to product, and the looming wave of AI-driven software.In the news:Pendo CEO talks ‘founder mode,’ going public and his Raleigh software firm’s first profit: https://www.newsobserver.com/news/business/article293725529.htmlHow Todd Olson of Pendo Got His First Customers: https://www.inc.com/alexa-von-tobel/todd-olson-pendo-customer-journey.htmlOlson’s ambitious journey: https://www.bizjournals.com/triangle/news/2022/04/08/todd-olson-leads-pendo-ambitious-journey.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/
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    1 hr and 30 mins

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