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.
Episodes
From the world of tech startups to the high-stakes world of sneakers, Walk West CEO and founder Greg Boone is a serial entrepreneur with a unique journey. With a background in computer science and a history of building and investing in companies, Greg brings a fresh perspective on how to navigate the current "AI tsunami."
Tune in to hear:
- Greg's entrepreneurial journey, from his computer science degree at North Carolina ...
What happens after you sell a company you helped turn around?
For Dr. Doug Kaufman, it’s a story of new ventures and hard-won lessons.
In this second part of a two-part series, Doug discusses his time at TransLoc, a mass transit technology company he helped lead to a successful sale to Ford.
He shares how he navigated a challenging acquisition process and the importance of a strong, collaborative board. He also talks about th...
What happens when a classically trained psychologist leaves the world of academia to shift careers?
For Dr. Doug Kaufman, it was to become a serial entrepreneur (obviously).
Doug's story is defined by a relentless curiosity about human behavior, a series of successful ventures, and some hard-won lessons in the chaotic world of startups.
In this first of a two-part series, Doug recounts his unconventional path from a psycholo...
From her upbringing in Johannesburg, South Africa, to a career spanning Wall Street, an Ivy League MBA, and the early days of e-commerce, Ricci Wolman’s journey is a all about problem solving, resilience, freedom, and...the paradox of choice?
As the CEO and co-founder of Written Word Media, she has built a bootstrapped and profitable business by solving a problem her own mom faced: book discovery in a crowded market.
Tune i...
What happens when a North Carolina native, seasoned by Silicon Valley and Wall Street, returns home to build a company that marries profit with purpose? For Jason Massey, co-founder and CEO of Ndustrial, it's led to a 14-year journey developing cutting-edge technology that makes industrial facilities more efficient and sustainable.
In this episode, Jason shares his unique path, from a childhood in Mebane and studying physic...
In Part 2 of our conversation with Eric Boduch, Pendo co-founder and CEO of Revcast, we explore the world of venture studios. Having left Pendo to pursue his vision of parallel entrepreneurship, Eric shares how his studio, 24 and Up, identifies, builds, and funds new companies.
This episode unravels the unique model of a venture studio, differentiating it from accelerators, incubators, and traditional venture capital. Eric ...
From co-founding one of the Triangle's most successful tech companies, Pendo, to quietly building a new venture studio, Eric Boduch has a deep well of entrepreneurial experience. In this first of a two-part series, Eric sits down with Scot to reflect on his journey, the lessons learned from the dot-com bust, and the evolution of product management.
Eric gets into his early days, his path to co-founding Pendo, and the st...
What happens when a seasoned entrepreneur spots a gap in the market and decides to take a risk on something entirely new? For Jason Widen, it’s led him from founding Raleigh Founded, a cornerstone of the Triangle’s startup ecosystem, to creating Blue Co. – a flexible warehouse solution designed for service-based businesses.
In this episode, Jason shares his journey of building community-driven businesses, from his early day...
Chris Heivly’s journey through the tech world is one for the books, literally - thanks to his deep-rooted love of maps. From his early days studying geography and computer mapping to shaping the future of internet navigation with MapQuest, Chris shares an inspiring story of innovation, risk, and community-building.
In this episode, we explore Chris’s entrepreneurial journey, discussing everything from his time building map ...
If you ask someone what’s at the heart of a successful engineering team, the answer might involve tools, talent, or tech. But Hersh Tapadia, CEO and co-founder of Allstacks, believes it all starts with one thing: measurable productivity. While we all know engineering teams face unique challenges, Allstacks is tackling the toughest one—how to measure and improve engineering productivity at scale.
In today’s episode, we talk ...
If you ask anyone about the entrepreneurial ecosystem in the Triangle, one name that keeps coming up is Dr. Tom Miller. Known as the champion of engineering entrepreneurship at NC State, Tom has been pivotal in shaping the region’s startup culture for over 40 years. From his early days in eastern North Carolina to founding the Engineering Entrepreneurs Program, his influence is felt across generations of entrepreneurs.
Toda...
Who will be crowned champion of Tweener Madness and take home the $25K investment from the Triangle Tweener Fund?
The championship features two radically different approaches to innovation:
- ZW (Robert Fu) – An AI-powered platform helping manufacturers optimize production and R&D in complex industries.
- InviteJet (Brian Watson & Paul Davis) – A calendar-based marketing solution helping brands reach customers at ex...
Who’s Advancing from the Fabulous Four - CivicReach or InviteJet?
Welcome back to Triangle Tweener Madness, the high-stakes startup tournament where eight companies go head-to-head for a $25,000 investment from the Triangle Tweener Fund!
We’re down to the Fabulous Four, and this week’s semifinal is a clash between a calendar-powered marketing platform and a voice AI company transforming local government services. Two...
What if the most powerful tool for success as an entrepreneur isn’t the latest strategy or tech hack—but the way you perceive and process every challenge you face?
In this episode of Triangle Tweener Talks, guest host Rebecca Ross sits down with Katherine Krupka, a leadership strategist and executive coach, to dive into the powerful connection between leadership, perception, and decision-making. Katherine has worked...
Who’s Advancing from the Fabulous Four - Moxie or ZW?
Welcome back to Triangle Tweener Madness, where four startups remain in the race for a $25K investment from the Triangle Tweener Fund!
In this week’s matchup, we’ve got two very different companies: one’s building AI to protect the integrity of academic research, and the other’s helping manufacturers optimize glass and ceramics production with deep tech. The stake...
Welcome back to Triangle Tweener Madness, where 8 startups go head-to-head for a $25K investment from the Triangle Tweener Fund!
This week, it’s a battle between a logistics platform built for scrappy e-commerce sellers and a surprising new marketing tool using your calendar.
Only one can move on to the next round. Let’s meet the contenders.
The Contenders
🔹 Deliveri (Jason Brown) – A full-service logistics tech stack for sm...
Guest host Rebecca Ross sits down with Phil Dixon, CEO of the Oxford Brain Institute and expert on neuroscience in leadership. With years of experience working with top companies like Apple, Google, and Facebook, Phil is bringing his insights to Raleigh Durham Startup Week as a keynote speaker.
You’ll hear Phil discuss:
- Why understanding brain science is crucial for entrepreneurs
- How emotional threats impact decision-maki...
Welcome back to Triangle Tweener Madness, where 8 startups go head-to-head for a $25K investment from the Triangle Tweener Fund! This week, it’s a clash of categories—govtech vs. asset tech—as two AI-powered platforms pitch their visions for transforming outdated systems. One startup is helping local governments serve residents more efficiently. The other is helping estate sale pros and collectors reclaim time and value in...
Bootstrapped vertical SaaS software company, Inn-Flow, raised $45m from Mainsail. In this exclusive interview we hear from CEO and co-founder John Erhart the history of Inn-Flow, how they got the deal done and what this means going foraward.
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Triangle Tweener Talks is sponsored by:
- Atomic Object: https://atomicobject.com/
Who’s Moving On in the Battle of EdTech?
Welcome back to Triangle Tweener Madness, where 8 startups go head-to-head for a $25K investment from the Triangle Tweener Fund! This week, two edtech startups take the stage in a battle of AI-driven learning solutions—but only one will move on to the next round.
The Contenders
🔹 Moxie (Jessica Parker) – An AI-powered research writing platform that helps graduate students,...
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