Triangle Tweener Talks
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. Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West. We couldn’t share posts like this without our amazing sponsors: Gold Sponsors: Balentine: https://www.balentine.com/triangle-entrepreneurs EisnerAmpner: https://www.eisneramper.com Robinson Bradshaw: https://www.robinsonbradshaw.com Silver Sponsors: Automated Consulting Group: https://automated.co Bank of America: https://business.bofa.com/en-us/content/technology-industry-group.html 2025 Sponsors: Extensis HR: http://www.extensishr.com/
Episodes
This episode is a big one. There’s a lot of noise right now around AI, venture, and whether SaaS is fundamentally broken. Public markets are re-rating software companies. Seed rounds are shifting. Pricing models are changing. And founders are asking the same question:
“Are we toast?”
Joe Mancini from Front Porch is in a unique position to answer that. His firm sits inside dozens of funds and startups across the Southeast and...
We started the Tweener List in 2015 with the idea of local founders paying it forward to help amplify and support our local startup ecosystem. Based on the popularity of that list and a grassroots effort to innovate a new way to help fund and support local founders, in 2022 we started the Tweener Fund.
That’s good, but it’s not enough. We’re always asking the community of founders we support - what else can we do to help yo...
In this episode of Triangle Tweener Talks, we unpack what it really takes to go from professor to CEO, how InsightFinder built trust in a skeptical enterprise market, and where LLMs help (and don’t) when you’re dealing with machine telemetry data. They also explore multi-agent workflows, “composite AI,” practical enterprise adoption hurdles, and Helen’s advice for students navigating an AI-shaped future.
Highlights cove...
In Part 1 of this conversation on Triangle Tweener Talks, we walked through how David built Offline over 13 years, three companies, multiple pivots, and a subscription model that finally worked.
In Part 2, we shift gears. This episode is about leverage. David breaks down how he went from running a ~34-person team to operating a multi-city business with ~2.5 people, not by cutting corners, but by rebuilding the company aroun...
This is Part 1 of a two-part conversation. In this episode, we focus on Offline’s origin story and business evolution, not AI (yet).
Highlights from Part 1
- Offline has effectively been three different companies under one brand
- Early versions tried to reinvent Meetup, and failed
- A city-guide app reached ~3M people/month but couldn’t monetize
- Consumer businesses can look successful while quietly breaking
- Subscription was the f...
Part 2 picks up where the origin story ends, and where the real work begins.
Tony breaks down the three phases of Phononic: proving the science, surviving productization, and ultimately finding the market where solid-state cooling wasn’t just better, but mission-critical. It’s a candid look at why deep-tech companies require patience, capital discipline, and brutal focus to survive.
This is the episode for founders navigatin...
In this episode (Part 1), we cover the origin story.
Tony walks through the decisions, failures, and inflection points that led to Phononic’s founding: leaving the Northeast for graduate school at USC, working on applied energy systems at JPL during the Mars rover era, and learning painful but formative lessons from a university spin-out that didn’t work.
Then comes the moment you can’t script. In the fall of 2008, while th...
In Part 2 of the conversation with Brice Englert, we move from origin story to execution and scale. We cover:
- Pricing without overthinking: how TradePending set pricing before having perfect data
- Sales-first growth: building an outside sales motion that paid for itself quickly
- Scaling with discipline: reaching profitability fast and choosing when to reinvest
- Private equity, from the founder’s seat: rolling equity, staying ...
In this episode (Part 1), Brice shares the early story: how the idea formed, how he got the first version built, what the market told him at the beginning, and what he did to push through the inevitable uncertainty that comes with building from scratch.
This is the origin story and early foundation of TradePending, before the scaling years.
You’ll hear:
- How Brice got started and why he chose automotive as the arena
- What th...
In this special solo episode of Triangle Tweener Talks, Scot goes beyond the two-part Tweener Times report to walk founders through what the data actually means in practice. This episode exists for one reason: to give Triangle founders clearer goalposts, better context, and fewer surprises when they sit down to raise capital.
Tune in to hear:
- How founders can self-service fundraising expectations using real Triangle ...
In Part 2 of this two-part deep dive, Triangle Tweener Talks host Scot Wingo sits down with legendary Triangle founder Mike Doernberg to explore his journey on scaling multiple companies, spinning out new ventures, navigating private equity, and why he never left North Carolina.
Tune in to hear:
- How ReverbNation grew from a side project into a 6M-artist platform
- The spin-out journey behind Adwerx, and why it worked
- Mike’s ...
In Part 1 of this two-part deep dive, Triangle Tweener Talks host Scot Wingo sits down with legendary Triangle founder Mike Doernberg to explore the earliest chapters of his career, from CPA to multi-exit entrepreneur.
Mike walks through the founding of Marathon, the rise of early PC-driven consulting, the creation and spinout of SmartPath, raising capital through the old-school angel gauntlets, navigating the DoubleClick a...
Mark Flickinger is the COO and General Partner at BIP Ventures, one of the Southeast’s most active venture firms. Based in Atlanta, Mark brings a rare dual perspective, an operator who scaled startups before joining the investing side. Since 2015, he’s helped BIP expand from an Atlanta-centric firm into a major player across the Southeast and Midwest.
Every year, BIP Ventures releases its State of Startups in the Southeast ...
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...
Popular Podcasts
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Saskia Inwood woke up one morning, knowing her life would never be the same. The night before, she learned the unimaginable – that the husband she knew in the light of day was a different person after dark. This season unpacks Saskia’s discovery of her husband’s secret life and her fight to bring him to justice. Along the way, we expose a crime that is just coming to light. This is also a story about the myth of the “perfect victim:” who gets believed, who gets doubted, and why. We follow Saskia as she works to reclaim her body, her voice, and her life. If you would like to reach out to the Betrayal Team, email us at betrayalpod@gmail.com. Follow us on Instagram @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.
The official podcast of comedian Joe Rogan.
The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com