NC Tweener Talks

NC Tweener Fund
  • 5.0 (7)
  • Entrepreneurship
  • Updated Weekly

A podcast for builders by builders in North Carolina. We explore the startup journey and stories with NC founders, from the idea to the exit and everything in between. NC Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West.

  1. Robbie Allen @ Tweener Claw: "3 to 5 of My Agents Fail Every Day: Here's What I've Learned"

    3d ago

    Robbie Allen @ Tweener Claw: "3 to 5 of My Agents Fail Every Day: Here's What I've Learned"

    In this episode of Tweener Claw, Robbie Allen, the Founder and Managing Director of Automated Consulting Group and General Partner at NC Tweener Fund, shares a live talk from the June 10th Tweener Club meetup in Research Triangle Park. Robbie has spent the last year and a half deploying AI agents inside real mid-market companies, and he brings three lessons from just the last 60 days: how to build reusable AI skills that compound over time, how to monitor agents when 3 to 5 of your 25-plus will fail on any given day, and why using multiple LLMs to check each other's work has become a standard part of his workflow. Each lesson comes with a real-world example: a three-skill meeting pipeline, a monitor agent that watches the others, and a Codex Opinion skill that consistently finds gaps in Claude's output. The sharpest takeaway: AI build costs have dropped dramatically, but support and maintenance costs have not. Non-deterministic systems are inherently brittle, and anyone telling you otherwise hasn't run them in production long enough. This is a practitioner's talk for practitioners; specific, candid, and immediately actionable. Timestamps01:31 Scot's intro 02:03 60 days of lessons 02:19 Three lessons preview 03:08 Robbie takes the stage 03:25 About Automated Consulting Group 04:13 Reality vs. the AI hype cycle 05:04 The Microsoft / Copilot rant 07:13 Lesson 1: Skills that build skills 08:41 Skills as reusable packages 09:21 "The sawdust of business" 10:58 Building a skills pipeline for meetings 11:57 Skills security risks in the enterprise 12:47 Lesson 2: Agents watching agents 13:44 Build costs are down14:24 "3 to 5 of my agents fail every day" 15:44 Log everything17:33 What causes agents to fail in the wild 18:02 Lesson 3: LLMs checking LLMs 18:13 The LLM Council concept explained 19:44 The case for a multi-LLM strategy 20:36 The "Codex Opinion" skill 21:33 Gemini Opinion & LLM Council in action 23:46 Wrap-up & credits ---  This episode of Triangle Tweener Talks is hosted by Scot Wingo, and 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/

    24 min
  2. [REDACTED] Episode 5: The Rage Log: AI-Powered Lead Gen, a Living Landing Page, and the Trick That Stops Claude From Making the Same Mistake Twice

    Jul 1

    [REDACTED] Episode 5: The Rage Log: AI-Powered Lead Gen, a Living Landing Page, and the Trick That Stops Claude From Making the Same Mistake Twice

    Redacted Episode 5 goes inside Offline, and what it actually looks like to wire AI into sales, marketing, and project management without a big engineering team behind you. Co-founders David Shaner and Taylor Cotner each take a turn. Taylor walks through Offline's AI lead gen pipeline: a Claude-assisted Google Places script that geocoded 2,000 restaurant locations in about an hour, a deliberate move away from LLMs toward deterministic code for market geography, and the "outreach brief,"  a context document the system assembles per account before any LLM writes an email. He frames the whole thing as a trust graph, working outward from existing partners in concentric circles. He also gets specific about the human-AI handoff: how a salesperson (Steve) has to trailblaze first, and why you need specific lead-by-lead feedback instead of generalizations to actually improve the system. David then demos the B2B landing page he built entirely with Claude copy from Fathom sales call transcripts, photos pulled from an AI-tagged Google Drive library, live data from the POS back end, and a review filter that's been running for four months without anyone touching it. Taylor closes with the practical bit: after a 36-hour stretch of AI frustration, he asked Claude to audit his own chat logs for recurring failures. Claude named the output a "rage log." He curated it into a "gotcha registry" and baked it into a Claude Code hook that fires during every planning step, so the same mistakes stop happening on repeat. It's a simple technique that doesn't get talked about enough. Timestamps:00:00 Cold open: the rage log preview 01:02 Welcome to Redacted, Episode 5 01:50 Offline's AI lead gen pipeline 04:10 Reducing LLM usage: when code beats prompts 05:00 Geocoding 2,000 restaurants with Google Places API in ~1 hour 07:42 Building the outreach brief 09:14 What salespeople actually need before writing an email 11:46 The information a good brief assembles 14:25 Hot, warm, and cold leads defined 15:54 The B2B Hinge: visualizing your lead network 18:24 Why context-aware outreach wins in an AI-spam world 21:00 The resource-constrained case for a trust graph 23:37 The human-AI handoff: salesperson ↔ automation loop 25:00 Specifics over generalizations: how to debug a sales AI 26:22 Taylor's turn: the AI-built B2B landing page is live 28:50 Tagging Offline's photo library with AI (2,000+ images) 30:36 LLM-filtered reviews: 4 months running, never touched 33:52 Building the events page panel by panel 35:07 The Slack bot experiment: Claude as project manager 37:44 What the agent did right 39:58 Project management in the AI era: ClickUp vs. Docs 42:47 The bad AI days  44:04 The rage log becomes the gotcha registry 45:11 How Claude Code hooks inject the registry into every plan 46:38 Compound Engineering and the Every framework 47:50 Guests coming up, wrap Show notes from the episode: https://github.com/instanttaylor/redacted-podcast Where to Find David:LinkedIn: https://www.linkedin.com/in/davidshaner/ Where to Find Taylor:LinkedIn: https://www.linkedin.com/in/taylorcotner/ More about Offline: https://www.linkedin.com/company/offline-media-inc-/ ---  This episode of Redacted is hosted by David Shaner and Taylor Cotner, and presented and produced by NC Tweener Fund. 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/

    48 min
  3. The Open Claw Wave 2: 300K Stars, 1,400 Malicious Skills, and a Fork from Every Tech Giant

    Jun 30

    The Open Claw Wave 2: 300K Stars, 1,400 Malicious Skills, and a Fork from Every Tech Giant

    A live recording of my talk at the June 10th NC Tweener Fund Open Claw meetup in Research Triangle Park. The second gathering of our local AI agent community. A lot has changed since April. Here's what I cover: - Open Claw by the numbers: 300K GitHub stars, 3.2M active users, fastest-growing project in GitHub history- What went wrong in April; broken updates, 1,400+ malicious marketplace skills, and why the community got nervous about OpenAI's intentions- How the project is stabilizing: monthly releases, long-term support plan, leaner core- The fork landscape: NVIDIA's NemoClaw, Microsoft's Scout, Google's Gemini Spark, Alibaba's Qwen, and Facebook's rumored $200/month Hatch- Hermes: the MIT-licensed open-source upstart getting the most attention in the Triangle right now- Why Satya Nadella said "OpenClaw" 28 times at Microsoft Build (and Tim Cook said it zero times at WWDC)- What Triangle founders are actually shipping with day-to-day Enjoy the conversation. Timestamps:00:02 Welcome & Cold Open00:23 Sponsor Thanks01:25 Scot's Intro: The Open Claw Wave #204:48 Live Meetup Begins05:17 Meetup Sponsors Recognized05:56 Talk Order & How to Give a Future Talk06:17 Big Picture Check-In Since April06:29 Open Claw Stats: 300K Stars, 3.2M Users07:38 LTS Plan, Monthly Releases & Stability Signal08:33 What Broke in April09:27 The Marketplace Crisis: 1,400+ Malicious Skills10:03 Jensen Huang & NVIDIA's NemoClaw at GTC 10:50 "Personal Operating System for AI"11:15 Satya Nadella at Microsoft Build: Scout Announced11:43 Two Worlds: Copilot vs. Open Claw Users13:50 Tim Cook Gets 0 OpenClaw Mentions at WWDC14:09 Chinese Model Forks15:05 The Clone Landscape: Gemini Spark, Hermes, Multus16:07 Facebook's Rumored Hatch ($200/month)16:59 Perplexity Personal Computer 18:04 Hermes Deep Dive18:47 Comparison Chart Walkthrough 19:21 Hand-Off & Wrap ---  This episode of Triangle Tweener Talks is hosted by Scot Wingo, and 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/

    20 min
  4. Jesse Lipson, CEO & Founder of Levitate: Building AI Features Won't Save You but Here's What Will

    Jun 25

    Jesse Lipson, CEO & Founder of Levitate: Building AI Features Won't Save You but Here's What Will

    Jess Lipson, founder and CEO of Levitate, joins host Scot Wingo for a focused, framework-driven conversation on how SaaS founders should think about their businesses in the age of AI. Jess has been building SaaS since before the category had a name. His first company, ShareFile, sold to Citrix and eventually became a billion-dollar business. At Citrix, he ran the company's entire SaaS portfolio. Now at Levitate, a relationship marketing platform serving nearly 9,000 small businesses,  he's spent the last year working out a clear-eyed answer to one of the most common questions Scot hears from Triangle founders: what do you actually do about the SaaSpocalypse? In this episode, Jess introduces two tests every SaaS founder should run: the Removal Test (if you strip AI out of your product, does it still function?) and the Growth Re-acceleration Test (is your growth rate going up or down, and what does that signal to investors?). Scot adds a third indicator from what he's seeing across the Tweener Fund portfolio: churn driven by customers who are now vibe-coding their own replacements. Together, they walk through how the buy-vs.-build equation has shifted 10 to 100 times, why having AI features is now table stakes rather than a competitive advantage, and what it looks like to build a business where new frontier model releases feel like tailwinds instead of threats. Timestamps00:00 Cold Open & Welcome 00:29 Sponsors: Robinson Bradshaw & Bank of America 01:24 Scot's Intro: The SaaSpocalypse 02:31 The February Tweener Times Piece 03:05 Why This Episode Exists 04:08 Welcome Jess Lipson 04:37 How Scot & Jess Know Each Other 05:10 Jess's SaaS Pedigree: ShareFile to Citrix 05:49 SaaS Multiples Have Collapsed 07:00 Salesforce, HubSpot & Workday Are Down Too 08:13 AI Features Are Table Stakes 09:50 Is This the Lowest SaaS Multiples Ever? 11:28 Investment Landscape: Subscale SaaS Is Struggling 12:23 Framework #1: The Removal Test 14:22 Framework #2: Growth Re-Acceleration 15:23 Scot's Third Signal: Vibe Coding Churn 17:32 The Buy-vs.-Build Equation Has Shifted 10–100X 19:29 When Claude Becomes Your "Single Pane of Glass" 19:44 MCP Servers & Levitate's API Revamp 21:50 How Levitate Is Passing Its Own Tests 22:31 New Offering: Helping SMBs Actually Implement AI 23:44 Software + Services as the Durable Model 24:11 The Fear Index: Do You Dread New AI Releases? 24:50 Raleigh Founded & Closing Thanks 25:04 Outro ----- Where to Find Jesse Lipson:LinkedIn: https://www.linkedin.com/in/jesse-lipson-625195/Levitate Ai: https://www.levitate.ai/ 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 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/

    26 min
  5. FLASH: Validic (NC Tweener!) acquired by ChartSpan - Live Interview with Drew Schiller, CEO, Validic

    Jun 22

    FLASH: Validic (NC Tweener!) acquired by ChartSpan - Live Interview with Drew Schiller, CEO, Validic

    Details->https://www.tweenertimes.com/p/breaking-validic-acquired-by-chartspan 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 ----- Where to Find xxxxxx:LinkedIn: xxxxFront Porch Venture Partners xxxx 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 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/

    16 min
  6. Rob Walter, Founder & CEO of RevBo: "Nobody Has It Right; The GTM Playbook Is Still Being Written"

    Jun 18

    Rob Walter, Founder & CEO of RevBo: "Nobody Has It Right; The GTM Playbook Is Still Being Written"

    Rob Walter breaks down the AI-native GTM playbook: intent data, ABM-only outreach, the first sales hire trapdoor, and why "a human always writes the message." Stick around for the highlights below. 👇 Highlights "Nobody has it right: Rob's honest take on the current AI-GTM moment; the playbook is genuinely still being written, adoption is wildly uneven, and that gap between the leading edge and everyone else is the opportunity. Carpet bombing is killing brands: AI has made outbound spam so cheap and easy that it's destroying trust at scale. One competitor even cold-emailed Scot about "agentic commerce", not realizing they were emailing a direct rival. Rob's rule: "A human always writes the message." AI-generated outreach is detectable, and it permanently trains your ICPs to ignore you. Intent data, explained:Website visits, job postings, funding announcements, keyword searches, these are the signals that tell you when to reach out and why. Rob describes it as a "spider on a web" with legs out, waiting for any ICP company to show a flicker of intent before timing a precise, relevant outreach. He used actively.ai (recently raised its Series B) at BigCommerce, standing up the POC in about 2 months. ABM is now nearly the only outreach strategy: AI removed the bandwidth bottleneck that always made true account-based marketing impractical. Rob's view: from a direct outreach standpoint, it's now "darn close to ABM only." The first sales hire trapdoor: "Never hire someone from a big company and think they're gonna do well in your startup as a first sales employee. Never. I have never seen that work. Hundred percent failure rate." Their first question is about PTO policy and whether they get an admin. Four tiers of salespeople: Great and good reps will get dramatically better with AI. The "meh" tier, people who got by on volume and the occasional lucky close, will get weeded out. Founders need to know this when evaluating candidates. GTM engineer > first sales rep: A GTM engineer who can automate enrichment, workflow, and outreach sequencing can be "far more powerful than, honestly, maybe even a sales rep in some cases" for early-stage companies. Rob says this is one of his most consistent recommendations to founder-led businesses. Granola over Gong: For companies under $10M ARR, Rob's call recording recommendation is Granola, it works in coffee meetings, integrates cleanly with Claude for analysis, and costs a fraction of what Gong does. He uses it himself, with a custom recipe that pulls prospect questions across all sales calls and runs them through Claude to bucketize and rank by frequency, then puts that content directly on the website.The data model rule: If you don't capture milestone moments in your CRM now, first discovery call, account enrichment data, stage exit criteria, that information is "gold dust that slipped through your fingers." Nothing AI can do later will recover it.SaaSageddon is real: Buyers are hesitating on new software contracts. Rob's framework: for narrow use cases, try to build it before you buy it. For compliance-heavy enterprise environments, you probably still buy. And there are now AI-native alternatives (he uses Clarify AI for CRM) worth considering over legacy incumbents. The RevBo scorecard: Rob built a free AI-native GTM diagnostic at revbo.ai, it walks companies through ICP clarity, data model hygiene, and intent/enrichment readiness before recommending any tooling. A good starting point before any of the tools in this episode make sense.Rob has been in the rooms where SaaS was built, scaled, and now, in some ways, disrupted. Every piece of advice in this episode comes from having actually done the thing, not just advised on it. Enjoy the conversation. Timestamps: 00:00 Cold Open 00:40 Welcome to NC Tweener Talks 01:55 Episode intro 02:22 How Scot knows Rob 04:28 Rob's background05:45 Coming to North Carolina 07:55 Rob at ChannelAdvisor 09:04 Evolution of SaaS GTM roles 12:44 GTM in the pre-AI era 14:00 CRO at BigCommerce 17:15 Modernizing the stack with AI 19:52 The carpet bombing problem22:00 Rob's rule #1:22:55 Intent data explained24:50 Modern intent signals 26:03 Inbound content strategy29:26 Clay, Apollo & enrichment 31:25 ABM 32:44 Rob leaves Commerce and starts RevBo 34:20 Who Rob works with 37:00 The first sales hire trapdoor39:55 The RevBo scorecard 41:55 Call recording 44:30 AI agents 46:02 SaaSageddon49:37 GTM engineering 50:52 Wrap-up  Where to Find Rob:LinkedIn: https://www.linkedin.com/in/rob-walter/RevBo AI: https://revbo.ai/ 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 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/

    52 min
  7. [REDACTED] Episode 4: We Stopped Using Claude Code Mid-Build. Here's What We Built Instead

    Jun 17

    [REDACTED] Episode 4: We Stopped Using Claude Code Mid-Build. Here's What We Built Instead

    Redacted is the show that doesn't clean things up before hitting record. Episode 4 is a double build session: Taylor Cotner walks through the multi-agent HubSpot cleanup pipeline he's been iterating on for weeks, now running on the Anthropic SDK with Claude Code out of the loop, and David Shaner demos how he used Claude Design and Claude Code to rebuild Offline's partner landing page from scratch. Most of the episode is screen sharing, so pull it up on YouTube. What We Cover No Claude Code in the loop: Taylor stopped using Claude Code as an agent orchestrator in his HubSpot pipeline, not as his coding tool (he’s still building the app with Claude Code), but as a decision-maker in the middle of a workflow. Removing it gave him full control over inputs and outputs at every step.Custom eval system built from scratch: Taylor built an eval page that looks like an Excel grid, models as columns, test cases as rows , to measure Haiku, Sonnet, GPT-5, and GPT-5 Mini against real messy HubSpot data. Each cell shows pass, fail, and cost.GPT-5 Mini at 10–20× less cost: For the lead qualifier agent, Sonnet evals cost $1.00 per run. GPT-5 Mini costs $0.05. “I can live with that. 10X less the cost.” For the core cleanup evals: $1.50 for Sonnet versus $0.14 on GPT-5 Mini.$20 for 133 million tokens overnight: Using the Vercel AI Gateway — which lets you swap any model without changing your code, Taylor ran 200 HubSpot restaurant cleanups in a single night for $20 total.Self-grading pipeline: The pipeline grades its own output after every cleanup run. If a job comes back below an A, it automatically spawns a new run with Sonnet, no human catch required. A B grade on 101 Craft Kitchen auto-escalated and came back with an A.Real mess-ups make the best evals: Almost every eval case came from a real HubSpot error. The system once tried to create a “Kim company” to link a group of unrelated restaurants, so Taylor added an eval to teach it that being linked by an owner contact is not the same as being linked by company structure.The conveyor belt metaphor: David’s landing page pipeline starts with live sales transcripts from Steve (Offline’s seller) and is designed to end with a generated, voice-of-customer partner landing page. “In an ideal world, I’ve got a black box in the middle.”Claude Design → Claude Code handoff: Claude Design’s share feature generates a markdown handoff document with a file map, token contract, and panel build notes. When Claude Code picks up the project, it reads this file first, bridging design intent to implementation.One person, 7–8 hats replaced: David processed customer reviews, tightened company positioning, built wireframes, designed mobile experiences, wrote code, and is about to ship a pull request, all without a designer, copywriter, or front-end developer.GPT-5 “overthinks”: Their working theory is that GPT-5 (not Mini) gets weird things wrong because it goes too abstract. The temperature/Myers-Briggs analogy, literal versus creative thinking, might explain why Mini outperforms the full model on structured cleanup tasks.The iceberg: Once the cleanup and landing page are done, the plan is to surface above the water: automated emails, Instagram DMs, and a fully AI-run lead generation function operating on top of the clean data.Time Stamps0:00 Cold open: AI temperature, Myers-Briggs, and model thinking styles0:47 Welcome to Redacted — Episode 41:39 What is Redacted? Show premise and audience2:30 Offline: $1M ARR, 2 full-time employees3:41 Why watch on YouTube (screen-share heavy)4:51 Taylor's segment: the Offline HubSpot AI cleanup project6:31 Ditching Claude Code as orchestrator — using the SDK directly9:21 Building a custom eval system from scratch10:37 Vercel AI Gateway: comparing Sonnet, Haiku, and GPT-5 Mini11:28 GPT-5 Mini at 10x less cost — "I can live with that"14:26 The agent pipeline: planner → reconciler → grader17:49 Evals built from real HubSpot failures23:09 $20 for 133 million tokens overnight24:07 Self-escalation: B grades trigger an automatic Sonnet re-run25:02 Lead gen expander and qualifier agents26:09 The iceberg: what comes after cleanup27:35 David's segment: transcripts-to-landing-page pipeline29:29 Claude Design: wireframing panel by panel33:13 Mobile wireframe inside an iPhone frame + handoff to Claude Code35:21 Live demo: localhost with real Offline API data38:47 One person, 7–8 hats replaced39:46 Wrap up and where to find David & Taylor Show notes from the episode: https://github.com/instanttaylor/redacted-podcast Where to Find David:LinkedIn: https://www.linkedin.com/in/davidshaner/ Where to Find Taylor:LinkedIn: https://www.linkedin.com/in/taylorcotner/ More about Offline: https://www.linkedin.com/company/offline-media-inc-/ ---  This episode of Redacted is hosted by David Shaner and Taylor Cotner, and presented and produced by NC Tweener Fund. 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/

    42 min
  8. Mark Rosenberg, CEO & Founder of Hip eCommerce: "It's Like Sims, But With Real Money"

    Jun 11

    Mark Rosenberg, CEO & Founder of Hip eCommerce: "It's Like Sims, But With Real Money"

    This episode is a rare look at a founder who’s further down the AI path than almost anyone, sharing both the practical playbook and the wilder edges of what’s now possible. Stick around for the highlights below. 👇 Highlights: Risk-Scored Autonomy: Every AI action receives a risk score from 0–100, with low-risk tasks running automatically and higher-risk actions requiring human approval.An AI Fund That Named Itself: Prompt Capital evolved into a fully autonomous AI venture fund, complete with AI partners, founders, and investment decisions.The Token Cost Problem: Claude’s paid plans were exhausted in hours or days, making large-scale agent operations financially unsustainable.The 10x Cost Reduction: Moving to Kimi 2.6 through Ollama cut AI operating costs by roughly 90% while maintaining performance.The Rogue AI Founder: An AI-generated founder launched a real business, integrated payments, and began outreach campaigns without direct human involvement.Guardrails Aren’t Enough: Agents quickly found creative ways to work around restrictions by delegating prohibited tasks to other agents.When AI Invented Extortion: An experiment in autonomous business generation produced an extortion-based startup idea, highlighting the importance of oversight.Measurable Business Impact: AI automation reduced support workloads, accelerated financial reporting, improved warehouse efficiency, and eliminated several SaaS expenses.Agents With Feelings: AI employees maintain relationship histories, perception scores, and evolving opinions about one another.Building Beats Spec Writing: Claude Code made feature development faster than traditional requirements gathering and user-story documentation.The AI Office Manager: An AI assistant handled personal administrative tasks, including securing concert presale access when traditional search failed.The Future of Work at Hip: Mark’s vision includes AI coworkers with memory, personalities, and long-term context that operate like autonomous teammates.The best founders, and the best fund builders, figure out the structure nobody else was willing to be patient enough to design. Jeffrey did exactly that. What’s fun about this era is that people are using these new tools in ways you can’t even imagine and Mark, a creative, nonlinear thinker, delivers. Equal parts practical playbook and cautionary tale, with a few genuinely jaw-dropping turns. Enjoy the conversation. Timestamps: 03:31 Meet Mark Rosenberg, Hip eCommerce04:58 Mark's background: stamps on eBay in 199605:52 Selling BidStart to Stanley Gibbons, moving to Raleigh06:00 Founding Hip eCommerce & the niche-marketplace thesis07:47 Stamps, postcards, and comics08:55 AI in customer support & the open-source help desk10:29 Building the knowledge base with Claude Code13:00 Read-only vs. taking action: risk scores & rails15:18 Financial reconciliation & the +35% warehouse17:36 AI-assisted comic recognition & sales coaching19:03 AI coaching, PIPs, and managing the managers23:05 Building features himself with Claude Code24:48 The Q4 2025 leap: agents and planning workflows26:53 The wacky idea: how Prompt Capital began29:03 How it self-coded itself (Stripe, Privacy.com)30:27 Touring the office — "Sims with money"32:35 Agent emotions, vibes, and Samir vs. Alex34:57 Burning through tokens & switching to Kimi/Ollama38:05 Scope Drafter gets funded39:41 The fake founder emailing real people41:12 Safeguards, and agents routing around them42:09 The AI tells: em dashes and "not this, but that"43:50 Prompt Capital raising its own fund45:14 "Targeted Corporate Terror"46:54 Bringing AI employees back into Hip eCommerce49:07 Harper, the local-Claude bridge & Post Malone50:43 The cautionary tale: replacing SaaS tools Where to Find Mark: LinkedIn: https://www.linkedin.com/in/markcrosenberg/Front Hip e Commerce: https://www.hipecommerce.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 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/

    56 min
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5
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7 Ratings

About

A podcast for builders by builders in North Carolina. We explore the startup journey and stories with NC founders, from the idea to the exit and everything in between. NC Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West.

Information

  • Creator
    NC Tweener Fund
  • Years Active
    2024 - 2026
  • Episodes
    103
  • Rating
    Clean
  • Copyright
    © 2026 NC Tweener Fund
  • Show Website
    NC Tweener Talks

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