Triangle Tweener Talks

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it’s a clash of categories—govtech vs. asset tech—as two AI-powered platforms pitch their visions for transforming outdated systems.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 the secondary market.

Let’s meet the contenders.

🔹 CivicReach (Chip Kennedy) – A voice-based AI platform that helps cities and counties improve the customer experience of government services—think tax appeals, pothole complaints, and zoning requests. CivicReach replaces confusing forms and long hold times with AI that actually solves your problem.
🔗 Learn more about CivicReach

🔹 Valuable (Amy Wolpert, John Wolpert, John Bozeman) – A platform for estate sale pros and collectors to inventory, research, and manage valuable items using AI. It’s Kelley Blue Book meets digital asset curation, solving a huge pain point in a growing secondary market.
🔗 Learn more about Valuable

🎤 Chip’s Pitch (CivicReach)

🎤 Valuable’s Pitch

Selection Committee Insights

💡 Dave Neal (Duke Capital Partners): CivicReach impressed with a sharp pitch and a clear understanding of the problem they’re solving—one that affects millions and is long overdue for innovation. Valuable, meanwhile, offers an intriguing product with potential applications beyond estate sales, including insurance and asset management.

💡 Kevin Mosley (Jurassic Capital): CivicReach has strong early traction, a capable team, and a clear roadmap to growth, especially as governments look to modernize. Valuable is tackling a unique and under-the-radar opportunity in the secondary market and could evolve into a much larger platform over time.

💡 Evan Shear (Oval Park Capital): Valuable has an exciting long-term vision and a product that could scale rapidly into multiple verticals, from collectibles to insurance. CivicReach, on the other hand, is already gaining momentum with a smart, apolitical solution to an outdated civic challenge.

Who Will Move On? 🏆

After a thoughtful debate, one startup gets the nod to move forward in Tweener Madness and the chance to compete for the $25K investment. Which company did the committee choose? You’ll have to tune in to find out!

📌 Timestamps

(00:00:39) – Host Scot Wingo introduces the matchup: CivicReach vs. Valuable, and welcomes the selection committee.
 (00:02:03) – Chip Kennedy (CivicReach) pitches a voice-based AI platform to modernize local government service delivery.
 (00:08:06) – Judges dive into Q&A: competition, procurement cycles, onboarding, and why CivicReach resonates across political lines.
 (00:20:56) – The team from Valuable (Amy, John & John) pitches their AI-driven platform for estate sale pros and collectors.
 (00:28:02) – Judges ask about business model, market size, product features, pricing, and long-term vision.
 (00:40:07) – Marketplace models, expansion potential, and monetizing unique features like expert appraisals and asset provenance.
 (00:43:18) – Final deliberation: Judges weigh immediate traction against longer-term scale potential.
 (00:45:17) – The votes are in. One company advances to the Fabulous Four.
 (00:47:00) – Closing thoughts from Scot and the judges.

🎙️ Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.

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