NC Tweener Talks

Round 2 of Tweener Madness is here. With a spot in the next round on the line, Iguana Cyber and HAM (Hierarchical Agent Memory) go head-to-head in a high-stakes pitch battle.

One is building next-gen cybersecurity to stop AI-driven exploits. The other is helping engineering teams cut AI costs and improve performance. Both are technical. Both are ambitious.
 
But only one moves forward.

🧠 What you’ll see in this episode:

•  A cybersecurity startup tackling unknown AI threats 
•  An AI infrastructure company optimizing token usage and cost 
•  Live investor Q&A and real feedback 
•  What founders get wrong (and right) when pitching technical products

👇 Featuring the Round 2 Selection Committee:

•  Jan Davis - RTP Angel Fund / Triangle Angel Partners 
•  Robbie Hardy - Accel Ventures 
•  Jen Summe - Primordial Ventures 

👉 Subscribe for more episodes as we move through the bracket
👉 Follow along as we go from the Exceptional 8 → Fantastic 4 → Championship

⏱️ Timestamps

00:00 — Welcome to Tweener Madness 
00:45 — Round 2 Intro: Iguana Cyber vs. HAM
01:15 — Iguana Cyber Pitch
06:20 — Iguana Cyber Q&A

15:30 — HAM Pitch
18:00 — HAM Q&A

27:20 — Judges Feedback Begins
27:30 — Feedback on Iguana Cyber
29:50 — Feedback on HAM
31:00 — Pitch Lessons (Clarity, Jargon, Slides)

31:30 — Final Decision (Winner Revealed)

🎯 About Tweener Madness

Tweener Madness is run by the NC Tweener Fund, Powered by NC IDEA and showcases top startups from across North Carolina. The winner receives a $25,000 investment and statewide exposure.

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Tweener Madness is hosted by Scot Wingo, run by NC Tweener Fund, Powered by NC IDEA, and brought to life by Walk West, who leads production and podcast creation.

We couldn’t share posts like this without our amazing sponsors: 

Platinum: 
NC IDEA: https://ncidea.org

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 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

8 founders. One bracket. $25,000 on the line. Welcome to Tweener Madness 2026, the high-stakes startup competition where North Carolina’s most promising companies go head-to-head.

In this Round 1 matchup, Utilyst and BeneDoc step into the arena to pitch their businesses to a panel of experienced investors. Each founder has one shot to make their case, answer tough questions, and prove they deserve to advance.

One moves on. One goes home.

🧠 What you’ll see in this episode:

•  A power infrastructure startup tackling knowledge loss in utilities 
•  A healthtech company rethinking regulatory workflows with AI 
•  Live investor Q&A and real-time feedback 
•  Behind-the-scenes judge deliberation (what actually matters in a pitch) 

👇 Featuring the Round 1 Selection Committee:

•  Jan Davis - RTP Angel Fund / Triangle Angel Partners 
•  Robbie Hardy - Accel Ventures 
•  Jen Summe - Primordial Ventures 

👉 Subscribe for more episodes as we move through the bracket
👉 Follow along as we go from the Exceptional 8 → Fantastic 4 → Championship

⏱️ Timestamps

00:00 — Welcome to Tweener Madness  
00:45 — Meet the Selection Committee  
03:05 — Format + What’s new this year  
05:05 — Matchup Intro: Utilyst vs. BeneDoc  
05:35 — Utilyst Pitch  
10:30 — Utilyst Q&A with Judges  
20:40 — BeneDoc Pitch  
26:15 — BeneDoc Q&A with Judges  
40:00 — Judges Deliberation Begins  
41:10 — Feedback on Utilyst  
43:10 — Feedback on BeneDoc  
46:20 — Pitch Lessons + What stood out  
49:05 — Final Decision (Winner Revealed)

🎯 About Tweener Madness

Tweener Madness is run by the NC Tweener Fund, Powered by NC IDEA and showcases top startups from across North Carolina. The winner receives a $25,000 investment and statewide exposure.

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Tweener Madness is hosted by Scot Wingo, run by NC Tweener Fund, Powered by NC IDEA, and brought to life by Walk West, who leads production and podcast creation.

We couldn’t share posts like this without our amazing sponsors: 

Platinum: 
NC IDEA: https://ncidea.org

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 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

This episode kicks off Season 2 of Tweener Madness and sets the stage for what’s ahead. You’ll get:

• The evolution of Tweener (from list → fund → statewide platform)
• Why this competition exists (and why founders love it)
• How the bracket works
• What judges are actually looking for
• And of course… the reveal of all 8 competing companies

This isn’t just a competition. It’s a behind-the-scenes look at how early-stage investors think.

🔥 What Were the Biggest Takeaways From the Selection Show?

• Tweener officially expands statewide with NC IDEA partnership
• $4M investment from NC IDEA fuels the next phase
• 50+ startups applied from across North Carolina
• Focus on venture-scale, IP-driven companies (not lifestyle businesses)
• Real investor judges, real feedback, real decisions
• Founders iterate pitches throughout the competition
• Episodes drop starting March 31, leading to a live championship

The stage is set. The pitches are ready. Now it’s time to see who can rise above the rest.

Timestamps

•  00:00 – Welcome to Tweener Madness 2026
•  00:40 – Tweener origin story (List → Fund → Media)
•  02:40 – NC IDEA partnership + statewide expansion
•  04:00 – Why founders love this format
•  05:00 – Sponsors + ecosystem support
•  06:20 – Meet the judges
•  10:10 – How the bracket works
•  12:00 – Selection criteria explained
•  15:20 – What didn’t make the cut (and why)
•  17:40 – The Exceptional 8 revealed
•  22:20 – Bracket matchups
•  23:30 – What’s next + episode schedule

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This episode of Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West. 

We couldn’t share posts like this without our amazing sponsors: 

Platinum: 
NC IDEA: https://ncidea.org

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 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

What does a go-to-market engineer actually do, and why is this role suddenly showing up everywhere?

In this episode, we unpack one of the fastest-evolving roles in modern startups. Evan shares how he went from using ChatGPT as a college student and new BDR to helping build AI-powered systems inside one of the Triangle’s best-known software companies.

The conversation covers how AI is changing outbound sales, why intent signals matter more than generic research, how tools like Clay, Cursor, Cloud Code, Lovable, n8n, and Supabase fit into a modern GTM stack, and why great go-to-market engineering is about making humans better, not replacing them.

Highlights Covered

• What a go-to-market engineer is and why the role is growing fast
• How Evan turned experimentation as a BDR into a new AI-focused role at Pendo
• Why intent signals + research create stronger outbound outreach than either one alone
• How Pendo uses AI to make BDRs faster, more focused, and more effective
• The difference between SDR inbound signals and BDR outbound signals
• How tools like Clay help enrich leads, personalize messages, and trigger outreach quickly
• Why the CRM still matters as the source of truth in an AI-heavy workflow
• How Evan builds internal dashboards using Salesforce, Supabase, Lovable, n8n, and Cloud Code
• Why GTM engineering is likely to split into multiple specialties over time
• How AI can increase sales productivity without replacing the people doing the work

If you’re a founder, operator, or revenue leader trying to understand where AI fits into your go-to-market motion, this episode is a practical look at what that future already looks like inside a fast-moving North Carolina company.

Timestamps:

• 05:05 — Meet Evan Inscoe from Pendo
• 08:05 — Evan’s background and discovering AI early
• 10:28 — What a BDR actually does
• 13:04 — How Evan created his own path into GTM engineering
• 16:29 — What the go-to-market engineer role looked like at the start
• 19:05 — Breaking down the BDR workflow
• 21:40 — Where Pendo is today after nine months of GTM engineering
• 23:00 — How Pendo uses Clay
• 24:45 — What counts as an intent signal
• 26:00 — Inbound vs outbound signals
• 31:00 — Why CRM still matters
• 35:20 — Measuring impact and efficiency gains
• 36:00 — Building dashboards with Lovable, Supabase, and n8n
• 42:35 — Tools Evan recommends most
• 43:40 — Driving adoption across the team
• 45:20 — Where GTM engineering is headed next
• 48:00 — Why AI won’t replace BDRs
• 48:45 — Evan’s next big project

Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo

Where to Find Evan Inscoe:
LinkedIn: https://www.linkedin.com/in/evaninscoe/

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This episode of Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West. 

We couldn’t share posts like this without our amazing sponsors: 

Platinum: 
NC IDEA: https://ncidea.org

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 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

This episode is a special one. We’re replaying NC IDEA’s Ecosysteming Podcast episode featuring Scot and Robbie following the announcement of the new North Carolina Tweener Fund, powered by NC IDEA. (Check out the announcement.) 

The conversation covers the “why” behind the partnership, how the Tweener model works, why statewide startup data matters, how founders can connect with the fund, and why this effort could attract even more outside capital into North Carolina. It’s part ecosystem strategy, part founder playbook, and part invitation to think bigger about what’s possible for startups across the state.

Highlights covered

• NC IDEA and the formerly Triangle-focused Tweener Fund have joined forces to create the North Carolina Tweener Fund powered by NC IDEA. The partnership expands the Tweener model from the Triangle to all of North Carolina
• Robbie shares his own story of receiving an NC IDEA grant in 2009 and how that support helped launch his startup journey
• Scot explains the origin of the Tweener List and how it became the foundation for the fund’s index-style approach
• The fund is designed to invest in a basket of promising North Carolina startups, helping reduce risk through diversification
• The discussion reinforces the idea that North Carolina has a uniquely broad startup base across sectors like AI, healthtech, agtech, aviation, manufacturing, ecommerce, and more
• Thom Ruhe highlights how better startup data helps ecosystem builders, policymakers, and funders make smarter decisions
• Scot and Robbie explain how increased visibility and deal activity can help pull more outside capital into the state
• Founders are encouraged to reach out directly, the approach is intentionally founder-friendly and operator-led
• The episode also outlines how accredited investors can participate, including through AngelList and, in some cases, retirement vehicles like self-directed IRAs

North Carolina’s startup ecosystem has been building toward this moment for years, and this conversation makes one thing clear: the next chapter is going to be bigger, broader, and more connected than ever.

Timestamps:

2:00 – Thom Ruhe introduces the episode and announces the NC Tweener Fund powered by NC IDEA
2:49 – Scot and Robbie react to the early excitement around the statewide expansion
4:00 – Why the NC IDEA and Tweener relationship makes sense from an ecosystem perspective
6:17 – Thom explains the bigger mission: creating a virtuous cycle for North Carolina’s economy
7:20 – Robbie’s background, his 2009 NC IDEA grant, and why NC IDEA mattered to his startup journey
11:05 – Robbie on joining Scot and helping grow the Tweener Fund
12:08 – Thom sets up the fund thesis and why the Tweener model stands out
14:03 – Scot’s background, startup history, and “pay it forward” approach to ecosystem building
16:47 – Scot explains product-market fit and why “tweener” companies are such an important stage
18:59 – The origin story of the Tweener List
20:18 – How the Tweener Fund grew out of the list and why diversification matters
22:50 – The index-fund analogy and how the Tweener model works
23:30 – How AI is changing startup timing and why Tweener is selectively moving earlier in some cases
25:07 – Why the Tweener List matters for policymakers and ecosystem builders
28:03 – Why mapping startups is harder than most people think
29:12 – What North Carolina startup formation data says about the state’s momentum
30:50 – Why becoming one of the most active funds matters for attracting attention and capital
33:20 – How outside VCs discover North Carolina through Tweener’s activity
35:28 – The case for bringing more outside capital into North Carolina
37:30 – How entrepreneurs can approach the North Carolina Tweener Fund
38:47 – How LPs and accredited investors can get involved
41:44 – Fund structure, fees, and why the model aims to be accessible
44:10 – Where to learn more and how to invest through the website
46:53 – Final thoughts on ecosystem impact and investment opportunities
47:52 – Quarterly LP webinars and using retirement vehicles like Alto
49:10 – Closing reflections on building a statewide startup ecosystem

Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo

Where to Find Robbie Allen:
LinkedIn: https://www.linkedin.com/in/robbieallen/

Where to Find Thom Ruhe:
LinkedIn: https://www.linkedin.com/in/thomasruhe/

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This episode of Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West. 

We couldn’t share posts like this without our amazing sponsors: 

Platinum: 
NC IDEA: https://ncidea.org

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 
 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

In this episode, we unpack how a college capstone project turned into a scalable system for custom-fit 3D-printed bracing, moving from “hours in CAD” to minutes with automated design templates. We get into the origin story, the technology moat, go-to-market evolution, fundraising, and the founder mindset required to stay in the game.

Highlights covered

• How PROTECT3D started with a custom brace for a Duke teammate
• Why “one-size-fits-none” is the real problem in bracing
• The core workflow: iPhone scan → automated digital design → 3D print
• How they reduced design time from 5+ hours to under 5 minutes
• Material/printing approaches and why they use multiple technologies
• Scaling from sports to insurance-reimbursable clinical products
• Expansion into military / defense applications via non-dilutive funding
• Founder lessons: failing fast, surviving COVID-era building, and grit
• Kevin’s advice to younger founders: keep going, the grind is the game

Custom-fit should be the norm, and PROTECT3D is building the rails to make that possible at scale. If you’re a founder working at the intersection of software + real-world manufacturing, this one is packed with practical lessons and a lot of heart.

Timestamps:
00:04:29 — Kevin’s background: Greensboro → Duke mechanical engineering + football

00:05:43 — The spark: 3D-printing a custom brace for an injured teammate

00:06:37 — “One-size-fits-none”: why off-the-shelf bracing fails most bodies

00:10:23 — Turning it into a real company through Duke I&E + early traction

00:12:21 — Early funding: friends & family + NC IDEA Micro Grant path

00:16:45 — The modern 3-step process: app scan → digital fabrication → 3D print

00:17:11 — From traveling to scan athletes… to scanning with an iPhone app

00:23:29 — Scaling breakthrough: design time drops from 5+ hours to <5 minutes

00:24:19 — Growth: working with over half of NFL teams + other leagues

00:25:21 — Beyond sports: clinics, insurance reimbursement, nationwide footprint

00:32:44 — Fundraising + non-dilutive: ~$5.5M raised, including DoD/SBIR support

00:34:44 — Founder lessons: fail fast, market expansion timing, surviving COVID

00:36:25 — Team size: 12 FTE + ~5 contractors; vision for clinical-scale bracing

00:38:30 — New channel: “at-home” scanning + direct-to-consumer experiments

00:41:18 — Kevin’s message to young founders: keep at it, the grind doesn’t stop

Where to Find Kevin Gehsmann:
LinkedIn: https://www.linkedin.com/in/kevin-gehsmann/
Front PROTECT3D: https://protect3d.io/

Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo

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This episode of 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: 

Platinum: 
NC IDEA: https://ncidea.org

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 
 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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 beyond. He sees what’s working, and what’s not, in real time. So we dug into the thesis behind their “SaaS is Dead” piece, what it actually means, and what founders should be doing right now.

Highlights covered

• Why SaaS is being re-rated in public markets
• Whether this is permanent or cyclical
• AI-native vs. AI-immigrant companies
• The collapse (and split) of the traditional “seed” round
• Why vertical SaaS may explode in this era
• How founders should think about churn in the AI era
• Internal resistance to AI adoption (and why it’s dangerous)
• What venture firms are actually looking for right now

The next decade belongs to founders who deeply understand their vertical, obsess over customer value, and move fast enough to build moats before the standards settle.

Timestamps:
07:00 – From sports radio to venture capital

10:30 – The hybrid fund model explained

16:50 – Why they wrote “Yes, SaaS Is Dead”

18:00 – The SaaS public market re-rating

21:00 – The split in seed investing

23:30 – AI-native vs AI-immigrant companies

27:00 – The 3-layer cycle of every tech revolution

30:00 – The 2x2: where opportunity lives now

33:00 – Why vertical beats horizontal right now

38:00 – Internal AI adoption is non-optional

39:30 – The shift from seat pricing to performance pricing

51:00 – What actually counts as a moat in AI

Where to Find Joe Mancini:
LinkedIn: https://www.linkedin.com/in/jpmancini/
Front Porch Venture Partners: https://www.frontporchvp.com/

Where to Find Scot Wingo: 
LinkedIn: https://www.linkedin.com/in/thescotwingo/ 
Tweener Times: https://www.tweenertimes.com/ 
X: https://x.com/scotwingo

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This episode of 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: 

Platinum: 
NC IDEA: https://ncidea.org

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 
 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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 you grow your companies, raise capital, provide more resources, enhance the community, etc. So, in the last two years we launched numerous community facing resources, including Tweener Talks.

What’s Next? 👉 NC Tweener Fund, Powered by NC IDEA! In this episode, Scot and Robbie hit the highlights of our newest adventure:

• Expanding geography from Triangle to NC (strategy and everything else stays consistent)
• Increasing our investment $/Q - that means more companies will be supported
• Bigger pool of potential investors (LPs)
• We'll be expanding our events, content and more
• Stay tuned for future news!

Timestamps:
00:32 – Big Announcement: Becoming the North Carolina Tweener Fund (Powered by NC IDEA)
00:53 – The Origin Story: Tweener List (2015)
01:28 – Launch of the Tweener Fund (2022)
01:35 – Expansion into Founder Content (Tweener Times, Tweener Talks, Community Hub)
03:52 – Robby’s NC IDEA Grant Story (2009)
04:36 – Why the NC IDEA Partnership Makes Sense
05:08 – Expanding Beyond the Triangle to All of North Carolina
06:07 – What Qualifies as a North Carolina
06:53 – Increasing Investments Per Quarter
07:22 – What’s NOT Changing (Commitment + Triangle HQ)
08:32 – Breaking Down NC Regions
09:40 – PitchBook Data: Where NC Startups Are Located
10:23 – Geographic Diversification Strategy Going Forward
11:21 – How to Get Involved (Investors + Sponsors)
12:26 – Thank You + Official Welcome to the NC Tweener Fund Era

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This episode of 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: 

Platinum: 
NC IDEA: https://ncidea.org
 
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 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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 covered

• Helen’s origin story: NASA Pathfinder work → distributed systems reliability → ML-based prediction
• The Google chapter: being invited to evaluate anomaly-detection algorithms with SRE teams
• Bootstrapping InsightFinder via NSF/SBIR funding + early angels, before raising traditional VC
• The professor-to-CEO transition: prioritization over “balance,” and learning to adapt daily
• Why founders should lead early sales (especially when the product is new-to-the-world)
• How InsightFinder runs enterprise PoCs using a “replay mechanism” on historical incidents
• “Composite AI” + using LLMs to translate technical insights into understandable narratives

If you’ve ever wondered what “AI that actually works” looks like in the enterprise, and how a research-driven founder earns trust at Fortune scale, this one’s a must-listen.

Timestamps

• 00:02:12 — Intro to Helen + what InsightFinder does
• 00:04:32 — Helen’s background at NC State
• 00:05:49 — Google discovers the research
• 00:06:24 — NSF/SBIR bootstrap + company start
• 00:07:10 — Early ML roots (since 2000)
• 00:08:54 — NASA Pathfinder origin story
• 00:12:03 — Teaching + student questions evolving
• 00:13:28 — Student → PhD → InsightFinder spark
• 00:14:36 — Professor + CEO time management
• 00:17:39 — Learning sales as a founder
• 00:21:24 — Funding path: SBIR + angels + first VC
• 00:22:44 — IDEA Fund connection story
• 00:24:19 — LLM era impact + “composite AI”
• 00:26:45 — LLMs as the interface layer
• 00:28:20 — Plain-English explanation of InsightFinder
• 00:31:04 — Agent workflows (Jira, probing, reports)
• 00:32:31 — Multi-agent + SLM orchestration
• 00:35:32 — PoCs: dogfood + replay mechanism
• 00:37:41 — How early detection works (hours ahead)
• 00:39:00 — Series B + scaling go-to-market
• 00:43:00 — LLMs: maturity + “last mile” problem
• 00:45:30 — Fine-tuning + trust risks
• 00:47:14 — Advice for students + fundamentals

#TriangleTweenerTalks #TriangleStartups #NCState #AIOps #Observability #SiteReliability #SRE #DistributedSystems #MachineLearning #EnterpriseAI #LLMs #AgenticAI #MCP #StartupJourney #FounderStories #B2BSoftware #DeepTech #RaleighDurham #NorthCarolinaTech

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This episode of 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 

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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 around AI-first systems, orchestration, and context-aware automation.

This is not “AI news.” This is how a founder is actually using AI day to day.

Highlights from Part 2

• AI adoption started as a “copywriting intern,” not a silver bullet
• The biggest fork: people who learned how to talk to models vs. people who gave up
• The real unlock came when David built his first full-stack app himself
• Tools like Cursor and Cloud Code collapsed the barrier between idea and execution
• Offline stopped adding features to a monolith, and started building around it
• n8n became the orchestration layer that glued everything together
• Most business problems don’t need apps, they need glue code
• AI SDRs fail today because context is fragmented and CRMs are a mess
• The right approach is decomposing SDR work into atomic steps
• Context windows are the real constraint, not intelligence
• David now runs a personal “Chief of Staff” GitHub repo with 70–80 skills
• The company itself is slowly becoming a file system agents can read and write from

If you’re thinking about automation, agents, or headcount, this one will change how you think about all three.

Where to Find David Shaner:
LinkedIn: https://www.linkedin.com/in/davidshaner/
Offline Media: https://www.letsgetoffline.com/

Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo

Timestamps
00:00–02:30 – Why Part 2 matters
02:30–06:00 – Phase 1: AI as a copywriting intern
06:00–10:00 – Phase 2: coding, Cursor, and the “hit by a bus” moment
10:00–13:00 – Why founders need to build something themselves
13:00–17:00 – Orchestration layers and why n8n won
17:00–21:00 – Why AI SDRs mostly don’t work yet
21:00–24:30 – Context windows, atomic steps, and agent design
24:30–27:30 – Debugging workflows like a human
27:30–31:30 – How Offline reduced headcount without losing velocity
31:30–36:00 – Self-service platforms for restaurants and events
36:00–39:30 – Cloud Code, skill files, and the “singularity” moment
39:30–44:00 – The Chief of Staff repo and what comes next

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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West. 

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