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Welcome to Tweener Madness, the high stakes startup showdown where 8 promising companies go head to head for a $25,000 investment prize from the Triangle Tweener Fund.
Each round, 3 members of the selection committee will vote on which startups advance leading up to the finals in early April where one company will take home the top prize.
Before the competition kicks off, let's meet the people making the tough calls.
Where to Find David Gardner:
About Tweener Madness: https://www.tweenermadness.com
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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:
Welcome to Tweener Madness, the high stakes startup showdown where 8 promising companies go head to head for a $25,000 investment prize from the Triangle Tweener Fund.
Each round, 3 members of the selection committee will vote on which startups advance leading up to the finals in early April where one company will take home the top prize.
Before the competition kicks off, let's meet the people making the tough calls.
Where to Find Mitch Mumma:
About Tweener Madness: https://www.tweenermadness.com
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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:
Welcome to Tweener Madness, the high stakes startup showdown where 8 promising companies go head to head for a $25,000 investment prize from the Triangle Tweener Fund.
Each round, three judges will vote on which startups advance leading up to the finals in early April where one company will take home the top prize from the judges.
Before the competition kicks off, let's meet the people making the tough calls, the judges.
First up, Jan Davis.
Where to Find Jan Davis:
About Tweener Madness: https://www.tweenermadness.com
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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:
If you ask Alexa who invented Alexa, she'll tell you it was Amazon.com. While that's kinda true, the Alexa foundation was developed by Igor Jablokov and his team at Yap, which was acquired by Amazon in 2011.
Today, we talk to Igor and get the entire story - from a childhood in a Greek cave to pioneering AI advancements that shape the way we interact with technology today. As the founder of Pryon and an early force behind Amazon Alexa, Igor has been at the forefront of AI for over two decades. That's right, two decades in AI.
In this episode, we hear about Igor's journey, the origins and vision for Pryon, the AI revolution, and his predictions for the next wave of technology.
Tune in to hear:
Where to Find Igor Jablokov:
Where to Find Scot Wingo:
In this episode:
(00:03:00) From a Cave in Greece to AI Pioneer – How Igor’s early years shaped his curiosity about language and intelligence.
(00:10:21) Discovering Computers & Engineering – Learning to code on a Tandy Color Computer and choosing a career in tech.
(00:17:55) IBM & Early AI – Leading IBM’s AI team in the early 2000s and the technology that laid the groundwork for Watson.
(00:27:42) The Yap Story – Founding the first voice-to-text AI startup and working secretly with Apple on Siri.
(00:39:58) Amazon’s Surprise Acquisition – How Yap became the foundation for Alexa and why the deal almost didn’t happen.
(00:50:26) The Dream That Led to Pryon – The moment of inspiration that led Igor to start his next company.
(01:00:01) Raising $100M+ for Pyion – The challenges and wins in building a leading AI company in the Triangle.
(01:14:03) The Future of AI & AGI – Igor’s take on artificial general intelligence, AI risks, and ethical dilemmas.
(01:24:43) Why the Triangle is an AI Hub – The unique advantages of building AI startups in North Carolina.
In the news:
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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:
Few Triangle founders have experienced as many highs and lows as Jud Bowman.
From launching his first startup as a high school student to navigating the dot-com bust, leading Motricity through a billion-dollar market cap, and pivoting multiple times to stay ahead of industry shifts, Jud's entrepreneurial journey is nothing short of legendary.
In this episode, Jud discusses the evolution of his companies—Pinpoint, Motricity, Appia, and now Sift Media. Everything from cold-emailing VCs in the '90s to the rise and fall of ringtones, the power of persistence, and what’s next in the world of mobile advertising.
Tune in to hear:
Where to Jud Bowman:
Where to Find Scot Wingo:
In this episode:
(00:00:03) The Internet Bubble Wake-Up Call – Jud’s first taste of dot-com economics with a $500K “opportunity” from NBC.
(00:05:00) From Dorm Room to First Funding – How two high schoolers convinced investors to back their startup.
(00:14:00) Surviving the Dot-Com Bust – The hard lessons of a fraudulent CEO and a failing business model.
(00:26:00) Pivoting to Mobile – How a chance discovery of early mobile search led to a billion-dollar business.
(00:42:00) The Ringtone Gold Rush – Why ringtones were the first billion-dollar mobile market.
(00:53:00) Raising Big Money & Going Public – From pitching VCs to working with Carl Icahn.
(01:02:00) The iPhone Effect – How Apple’s closed ecosystem changed everything.
(01:10:00) The Fall & Rise of Sift Media – Pivoting again in a world of privacy-first advertising.
In the news:
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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:
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:
Where to Find Chris Evans:
Where to Find Scot Wingo:
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:
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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:
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:
Where to Find Richard Holcomb:
Where to Find Scot Wingo:
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:
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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:
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:
Where to Find Todd Olson:
Where to Find Scot Wingo:
In this episode:
[00:05:03] Ringing the Gong & Celebrating Deals
Todd 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 Origins
Hear 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: Cerebellum
Todd 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 Russia
Managing 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 Slootman
Todd 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 Crunch
Diving 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 Chip
Writing 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-Founders
Why 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 Investors
Todd 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 Obsession
From 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 AI
Todd opens up about reinvigorating Pendo’s culture post-COVID, re-committing to product, and the looming wave of AI-driven software.
In the news:
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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:
How do you grow a 350-person, globally distributed tech company—without outside venture funding?
In this episode of Triangle Tweener Talks, we chat with Peter Zaitsev, Co-Founder of Percona, who bootstrapped his open-source database services and software company from a scrappy two-person startup in the U.K. to a $50M+ revenue business headquartered right here in the Triangle.
Peter’s story is anything but linear. He talks about growing up in the Soviet Union, teaching himself assembly code on paper before he even touched a real computer, and starting his first company at age 19—where he quickly realized that “business risk is one thing, but risking a kidney is something else!” After stints with MySQL and a move to Seattle, he eventually settled down in Durham, North Carolina, growing Percona into an open-source industry leader that competes on pure value and top-tier support.
Whether you’re an early-stage founder, a bootstrapper at heart, or just love the behind-the-scenes tales of pioneering in open source, this episode is packed with candid lessons on innovation, risk tolerance, and how to “grow or go” without losing sight of what matters to you and your customers.
Tune in to hear:
Where to Find Peter Zaitsev:
Where to Find Scot Wingo:
In this episode:
(00:03:44) Growing Up in the Soviet Union: Peter describes learning code by writing assembly on paper and dreaming of real computers.
(00:08:09) Founding Spylog at 19: The excitement (and danger) of launching a web analytics startup in late ’90s Russia—“equity or a kidney” decisions included.
(00:13:15) MySQL & the Open-Source Spark: How Peter’s early clashes (and collaborations) with MySQL’s founders shaped his approach to open-source performance.
(00:26:30) Leaving MySQL & Moving to the UK: Peter’s leap from a corporate gig to founding Percona in London—and how consulting work morphed into something bigger.
(00:30:33) Percona Lands in California: Navigating the 2008 financial crisis, Sun’s acquisition of MySQL, and the unexpected tailwinds for open-source databases.
(00:40:01) Why the Triangle? Peter shares what drew him (and eventually Percona) to Durham, NC—seasons, startup culture, and less traffic than Silicon Valley!
(00:45:45) MySQL vs. PostgreSQL in the Cloud Era: The shifting momentum in open-source databases and why “tuning by credit card” happens on AWS and beyond.
(00:52:10) Building an Open-Source Ecosystem: From support subscriptions to new ventures like Altinity and Coroot—Peter explains his passion for transparent software.
(00:59:10) The Zero-to-One Founder Mentality: Why Peter thrives on the excitement of small, agile teams—and how he handles “too many good ideas” before breakfast.
(01:03:05) CEO Lessons: Knowing when to hire a CEO, evolving as a founder, and final thoughts on putting customers (not licenses) first.
In the news:
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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:
How do you turn a simple “what if?” into a thriving venture—especially when you’re blending creativity, technology, and a dash of entrepreneurial courage?
In this episode of Triangle Tweener Talks, we sit down with Tina Tang, Co-Founder and CEO of Bristles, an AI-driven platform that helps furniture refinishers and DIYers reimagine their projects before picking up a single paintbrush.
Tina shares her journey from civil engineering and data analytics into the world of startups, navigating the messy middle of product-market fit, and iterating her way from a broad concept to a laser-focused solution for a passionate niche audience. She talks candidly about how she used customer interviews, no-nonsense feedback, and evolving AI tools to refine Bristles into a tool that’s now cutting DIY project mock-up time from hours to minutes.
Tune in to hear:
Where to Find Tina Tang:
Where to Find Scot Wingo:
In this episode:
(00:06:23) Immigrant Sacrifices and the American Dream
(00:13:27) Modeling Brain Functions Through Code Replication
(00:16:34) Legacy System Analysis for Modernization Success
(00:21:50) Advancements in Neural Networks and AI Technology
(00:27:47) Revolutionizing Photo Editing with Generative Models
(00:30:31) Geographical Constraints in Adobe's AI Product Management
(00:38:06) Interactive AI Photo Painting Tool Development
(00:46:26) Precision Photo Editing Tool for Home Improvement
(00:55:58) Enhancing User Experience Through Feedback Insights
(01:02:30) Bristles and Simplifying Furniture Design Tools
(01:15:52) Demand-Driven Strategy for Business Success
(01:18:15) Zero Friction Addiction: Customer Engagement Strategies
In the news:
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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:
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