Triangle Tweener Talks

Triangle Tweener Fund

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/

  1. How Pendo’s Evan Inscoe Is Building the Future of Go-To-Market Engineering

    21H AGO

    How Pendo’s Evan Inscoe Is Building the Future of Go-To-Market Engineering

    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 fastHow Evan turned experimentation as a BDR into a new AI-focused role at PendoWhy intent signals + research create stronger outbound outreach than either one aloneHow Pendo uses AI to make BDRs faster, more focused, and more effectiveThe difference between SDR inbound signals and BDR outbound signalsHow tools like Clay help enrich leads, personalize messages, and trigger outreach quicklyWhy the CRM still matters as the source of truth in an AI-heavy workflowHow Evan builds internal dashboards using Salesforce, Supabase, Lovable, n8n, and Cloud CodeWhy GTM engineering is likely to split into multiple specialties over timeHow AI can increase sales productivity without replacing the people doing the workIf 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 Pendo08:05 — Evan’s background and discovering AI early10:28 — What a BDR actually does13:04 — How Evan created his own path into GTM engineering16:29 — What the go-to-market engineer role looked like at the start19:05 — Breaking down the BDR workflow21:40 — Where Pendo is today after nine months of GTM engineering23:00 — How Pendo uses Clay24:45 — What counts as an intent signal26:00 — Inbound vs outbound signals31:00 — Why CRM still matters35:20 — Measuring impact and efficiency gains36:00 — Building dashboards with Lovable, Supabase, and n8n42:35 — Tools Evan recommends most43:40 — Driving adoption across the team45:20 — Where GTM engineering is headed next48:00 — Why AI won’t replace BDRs48:45 — Evan’s next big projectWhere 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/ ---  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  ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/

    50 min
  2. A New Chapter for North Carolina Startups: Scot Wingo and Robbie Allen on NC IDEA's #Ecosysteming Podcast

    MAR 12

    A New Chapter for North Carolina Startups: Scot Wingo and Robbie Allen on NC IDEA's #Ecosysteming Podcast

    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 CarolinaRobbie shares his own story of receiving an NC IDEA grant in 2009 and how that support helped launch his startup journeyScot explains the origin of the Tweener List and how it became the foundation for the fund’s index-style approachThe fund is designed to invest in a basket of promising North Carolina startups, helping reduce risk through diversificationThe discussion reinforces the idea that North Carolina has a uniquely broad startup base across sectors like AI, healthtech, agtech, aviation, manufacturing, ecommerce, and moreThom Ruhe highlights how better startup data helps ecosystem builders, policymakers, and funders make smarter decisionsScot and Robbie explain how increased visibility and deal activity can help pull more outside capital into the stateFounders are encouraged to reach out directly, the approach is intentionally founder-friendly and operator-ledThe episode also outlines how accredited investors can participate, including through AngelList and, in some cases, retirement vehicles like self-directed IRAsNorth 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 IDEA2:49 – Scot and Robbie react to the early excitement around the statewide expansion4:00 – Why the NC IDEA and Tweener relationship makes sense from an ecosystem perspective6:17 – Thom explains the bigger mission: creating a virtuous cycle for North Carolina’s economy7:20 – Robbie’s background, his 2009 NC IDEA grant, and why NC IDEA mattered to his startup journey11:05 – Robbie on joining Scot and helping grow the Tweener Fund12:08 – Thom sets up the fund thesis and why the Tweener model stands out14:03 – Scot’s background, startup history, and “pay it forward” approach to ecosystem building16:47 – Scot explains product-market fit and why “tweener” companies are such an important stage18:59 – The origin story of the Tweener List20:18 – How the Tweener Fund grew out of the list and why diversification matters22:50 – The index-fund analogy and how the Tweener model works23:30 – How AI is changing startup timing and why Tweener is selectively moving earlier in some cases25:07 – Why the Tweener List matters for policymakers and ecosystem builders28:03 – Why mapping startups is harder than most people think29:12 – What North Carolina startup formation data says about the state’s momentum30:50 – Why becoming one of the most active funds matters for attracting attention and capital33:20 – How outside VCs discover North Carolina through Tweener’s activity35:28 – The case for bringing more outside capital into North Carolina37:30 – How entrepreneurs can approach the North Carolina Tweener Fund38:47 – How LPs and accredited investors can get involved41:44 – Fund structure, fees, and why the model aims to be accessible44:10 – Where to learn more and how to invest through the website46:53 – Final thoughts on ecosystem impact and investment opportunities47:52 – Quarterly LP webinars and using retirement vehicles like Alto49:10 – 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/ ---  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   ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/

    51 min
  3. From Duke Football to 3D-Printed Medical Devices: How PROTECT3D Scaled Mass Customization with Kevin Gehsmann

    MAR 5

    From Duke Football to 3D-Printed Medical Devices: How PROTECT3D Scaled Mass Customization with Kevin Gehsmann

    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 teammateWhy “one-size-fits-none” is the real problem in bracingThe core workflow: iPhone scan → automated digital design → 3D printHow they reduced design time from 5+ hours to under 5 minutesMaterial/printing approaches and why they use multiple technologiesScaling from sports to insurance-reimbursable clinical productsExpansion into military / defense applications via non-dilutive fundingFounder lessons: failing fast, surviving COVID-era building, and gritKevin’s advice to younger founders: keep going, the grind is the gameCustom-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 ---  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   ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/

    44 min
  4. Will AI Kill SaaS? Triangle Founders Want to Know! We Deep Dive Into the SaaSageddon with Joe Mancini, GP at Front Porch Ventures

    FEB 26

    Will AI Kill SaaS? Triangle Founders Want to Know! We Deep Dive Into the SaaSageddon with Joe Mancini, GP at Front Porch Ventures

    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 marketsWhether this is permanent or cyclicalAI-native vs. AI-immigrant companiesThe collapse (and split) of the traditional “seed” roundWhy vertical SaaS may explode in this eraHow founders should think about churn in the AI eraInternal resistance to AI adoption (and why it’s dangerous)What venture firms are actually looking for right nowThe 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 ---  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   ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/

    53 min
  5. Announcing: NC IDEA and Tweener Fund Partnership

    FEB 20

    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 - 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 supportedBigger pool of potential investors (LPs)We'll be expanding our events, content and moreStay 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 Sense05:08 – Expanding Beyond the Triangle to All of North Carolina06:07 – What Qualifies as a North Carolina06:53 – Increasing Investments Per Quarter07:22 – What’s NOT Changing (Commitment + Triangle HQ)08:32 – Breaking Down NC Regions09:40 – PitchBook Data: Where NC Startups Are Located10:23 – Geographic Diversification Strategy Going Forward11:21 – How to Get Involved (Investors + Sponsors)12:26 – Thank You + Official Welcome to the NC Tweener Fund Era ---  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  ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/

    14 min
  6. Dr. Helen Gu on Building InsightFinder, AIOps, and the “Last Mile” of Enterprise AI

    FEB 17

    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 future. Highlights covered Helen’s origin story: NASA Pathfinder work → distributed systems reliability → ML-based predictionThe Google chapter: being invited to evaluate anomaly-detection algorithms with SRE teamsBootstrapping InsightFinder via NSF/SBIR funding + early angels, before raising traditional VCThe professor-to-CEO transition: prioritization over “balance,” and learning to adapt dailyWhy 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 narrativesIf 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 does00:04:32 — Helen’s background at NC State00:05:49 — Google discovers the research00:06:24 — NSF/SBIR bootstrap + company start00:07:10 — Early ML roots (since 2000)00:08:54 — NASA Pathfinder origin story00:12:03 — Teaching + student questions evolving00:13:28 — Student → PhD → InsightFinder spark00:14:36 — Professor + CEO time management00:17:39 — Learning sales as a founder00:21:24 — Funding path: SBIR + angels + first VC00:22:44 — IDEA Fund connection story00:24:19 — LLM era impact + “composite AI”00:26:45 — LLMs as the interface layer00:28:20 — Plain-English explanation of InsightFinder00:31:04 — Agent workflows (Jira, probing, reports)00:32:31 — Multi-agent + SLM orchestration00:35:32 — PoCs: dogfood + replay mechanism00:37:41 — How early detection works (hours ahead)00:39:00 — Series B + scaling go-to-market00:43:00 — LLMs: maturity + “last mile” problem00:45:30 — Fine-tuning + trust risks00:47:14 — Advice for students + fundamentals#TriangleTweenerTalks #TriangleStartups #NCState #AIOps #Observability #SiteReliability #SRE #DistributedSystems #MachineLearning #EnterpriseAI #LLMs #AgenticAI #MCP #StartupJourney #FounderStories #B2BSoftware #DeepTech #RaleighDurham #NorthCarolinaTech ---  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  ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/

    48 min
  7. From Founder to Chief of Staff: How Offline Runs on AI with David Shaner

    FEB 12

    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 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 bulletThe biggest fork: people who learned how to talk to models vs. people who gave upThe real unlock came when David built his first full-stack app himselfTools like Cursor and Cloud Code collapsed the barrier between idea and executionOffline stopped adding features to a monolith, and started building around itn8n became the orchestration layer that glued everything togetherMost business problems don’t need apps, they need glue codeAI SDRs fail today because context is fragmented and CRMs are a messThe right approach is decomposing SDR work into atomic stepsContext windows are the real constraint, not intelligenceDavid now runs a personal “Chief of Staff” GitHub repo with 70–80 skillsThe company itself is slowly becoming a file system agents can read and write fromIf 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 Timestamps00:00–02:30 – Why Part 2 matters02:30–06:00 – Phase 1: AI as a copywriting intern06:00–10:00 – Phase 2: coding, Cursor, and the “hit by a bus” moment10:00–13:00 – Why founders need to build something themselves13:00–17:00 – Orchestration layers and why n8n won17:00–21:00 – Why AI SDRs mostly don’t work yet21:00–24:30 – Context windows, atomic steps, and agent design24:30–27:30 – Debugging workflows like a human27:30–31:30 – How Offline reduced headcount without losing velocity31:30–36:00 – Self-service platforms for restaurants and events36:00–39:30 – Cloud Code, skill files, and the “singularity” moment39:30–44:00 – The Chief of Staff repo and what comes next ---  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-en... 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/conte...  2025 Sponsors: Extensis HR: http://www.extensishr.com/ ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/

    46 min
  8. Three Companies, One Brand: Building Offline Over 13 Years with David Shaner

    FEB 5

    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 1 Offline has effectively been three different companies under one brandEarly versions tried to reinvent Meetup, and failedA city-guide app reached ~3M people/month but couldn’t monetizeConsumer businesses can look successful while quietly breakingSubscription was the first model that truly workedRestaurants don’t want “deal seekers”, they want incremental revenueOffline works because it optimizes excess capacity, not discountsCOVID forced a near-shutdown, and a total rethink of operationsToday, Offline runs across 10 cities with ~600 restaurants and ~10,000 subscribersMost founders only hear about the winning version of a company. This episode shows the cost of getting there: years of pivots, wrong turns, false confidence, and learning, sometimes the hard way, how markets actually work. Offline didn’t succeed because of a clever growth hack. It survived because David kept learning, iterating, and refusing to confuse traction with sustainability. 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 Timestamps00:00–02:30 – Introduction & what this two-part series will cover02:30–05:30 – David’s background, NC State, and discovering entrepreneurship05:30–08:00 – The original idea: human connection in a screen-first world08:00–11:30 – Era 1: trying (and failing) to reinvent Meetup11:30–13:30 – Era 2: city guides, millions of users, zero monetization13:30–15:40 – Era 3: subscriptions finally click15:40–17:30 – COVID, near shutdown, and survival17:30–23:30 – Why restaurants accept discounts (the airplane seat analogy)23:30–25:30 – Why Groupon failed restaurants — and why Offline didn’t25:30–44:00 – Productivity, systems thinking, and process obsession44:00–45:10 – What’s coming in Part 2---  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   2025 Sponsors:  - Extensis HR: http://www.extensishr.com/ ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/

    46 min

Ratings & Reviews

5
out of 5
7 Ratings

About

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/

You Might Also Like