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Jason Gillikin
Triangle Podcasts
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Episodes
10
26 February 2026
Spotlight: Bailey's Fine Jewelry
A university…for brides? Hang out with Raleigh Magazine as Publisher Gina Stephens chats with local mainstay Bailey’s Fine Jewelry about its free, immersive class for couples—designed to cut through the confusion, try on rings, and ask real questions before buying. In partnership with Bailey’s Fine Jewelry
13346 h 24 min
26 February 2026
Is SaaS Dead? AI, Vertical Moats, and the Future of Venture with Joe Mancini
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...
14034 h 16 min
24 February 2026
Pricing Out Downtown?
When parking becomes a barrier, people don’t fight it—they leave. Gina Stephens and Melissa Howsam dig into Raleigh’s looming parking debate, the revenue shortfall driving it, and why rolling back free parking or upping rates could hurt the very businesses downtown is trying to keep alive. Free DTR Parking Pays Off Stay in the Know Get Social Meet Our Sponsors:Timber Pizza Woodhouse Spa...
10632 h 25 min
20 February 2026
Announcing: NC IDEA and Tweener Fund Partnership
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 -...
3754 h 15 min
17 February 2026
Dr. Helen Gu on Building InsightFinder, AIOps, and the “Last Mile” of Enterprise AI
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...
12861 h 6 min
17 February 2026
Talking Trash
Overflowing bins. Illegal dumping. Grime spreading beyond downtown. Publisher Gina Stephens and Editor-in-Chief Melissa Howsam dig into months of reporting to ask the uncomfortable question Raleigh residents keep whispering: is the city getting messier—or are its systems quietly falling behind its growth? Trash Talk: City’s Growing Trash Troubles Stay in the Know Get Social Meet Our...
13689 h 33 min
12 February 2026
From Founder to Chief of Staff: How Offline Runs on AI with David Shaner
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...
12189 h 30 min
10 February 2026
Raleigh Magazine’s Best Bars of 2025
The trophies have been handed out, the cocktails poured, and the industry showed up. Publisher Gina Stephens taps bar titan Matt Bettinger to break down Raleigh Magazine’s Best Bars—sharing standout winners, bartender of the year—plus the party, the afterparty and the people who make the scene hum. Meet Our Sponsors:Timber PizzaWoodhouse SpaVillage Tavern Get the issue to your door! Subscribe Now
24428 h 31 min
05 February 2026
Three Companies, One Brand: Building Offline Over 13 Years with David Shaner
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 1Offline 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...
12247 h 44 min
03 February 2026
Why Is Dating in Raleigh So Hard?
It’s an (un)Hinged world, and we’re just dating in it. After Raleigh landed 9th on a list of the worst large metros for finding love, Publisher Gina Stephens and Editor-in-Chief Melissa Howsam sat down to talk relationships. From dating apps and real-life connections to wins, disasters, and where to meet people beyond the apps, this is what dating actually looks like in Raleigh. Swipe Life: A...
10175 h 24 min