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

    Jesse Lipson, CEO & Founder of Levitate: Building AI Features Won't Save You but Here's What Will
    2026/06/25

    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.

    Timestamps
    00:00 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/
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    26 分
  • FLASH: Validic (NC Tweener!) acquired by ChartSpan - Live Interview with Drew Schiller, CEO, Validic

    FLASH: Validic (NC Tweener!) acquired by ChartSpan - Live Interview with Drew Schiller, CEO, Validic
    2026/06/22

    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: xxxx
    Front 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/
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    16 分
  • Rob Walter, Founder & CEO of RevBo: "Nobody Has It Right; The GTM Playbook Is Still Being Written"

    Rob Walter, Founder & CEO of RevBo: "Nobody Has It Right; The GTM Playbook Is Still Being Written"
    2026/06/18
    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://...
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    52 分
  • [REDACTED] Episode 4: We Stopped Using Claude Code Mid-Build. Here's What We Built Instead

    [REDACTED] Episode 4: We Stopped Using Claude Code Mid-Build. Here's What We Built Instead
    2026/06/17
    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 CoverNo 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 & TaylorShow notes from the episode: https://github.com/instanttaylor/redacted-podcastWhere 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 ...
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    42 分
  • Mark Rosenberg, CEO & Founder of Hip eCommerce: "It's Like Sims, But With Real Money"

    Mark Rosenberg, CEO & Founder of Hip eCommerce: "It's Like Sims, But With Real Money"
    2026/06/11
    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 toolsWhere 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.orgGold 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/
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    56 分
  • Moneyball for Main Street: The Fund That Bets on Singles, Not Home Runs

    Moneyball for Main Street: The Fund That Bets on Singles, Not Home Runs
    2026/06/04
    Most of us know Asheville as beer city, foodtopia, a playground for retirees and 14 million visitors a year. Jeffrey opens by updating that picture. Eighteen months out from Hurricane Helene, which hit on a Friday in late September 2024, the data is starting to come in. The long-term employment hit was about half that of COVID. Decades of population growth stopped in 2025 and even declined for the first time, but the in-migration that remains is now strongest among 25-to-34-year-olds: prime working-age professionals, not retirees. Jeffrey walks through what’s back (Biltmore Village, the River Arts District, High Wire’s new year-round pickleball courts) and what’s gone forever, and lands on a word he keeps coming back to: optimism.From there, we steer into the heart of the episode: Optimist Ventures and the funding mechanism Jeffrey invented, the SPA note. The origin story is its own lesson in adaptation. Optimist began as a half-million-dollar grant from the Dogwood Health Trust. Then Helene hit, and within the same week a founder in the program, Ginger Frank of Poppy Popcorn, called wanting to commit $100,000, but to a grant program, not a fund. Rather than walk away, Jeffrey spent days thinking until he landed on a hybrid: half the capital as grants and philanthropy, half in a for-profit vehicle for accredited investors, with every for-profit dollar matched by a donation.Boom: enter the SPA or shared profit agreement. The conversation closes on what’s next, whether this model can scale to Charlotte or Raleigh, and a heartfelt ask about how the rest of the state can help Asheville finish its recovery. HighlightsMoneyball the Portfolio: Instead of chasing one home run, Jeffrey set out to build a book of “singles and doubles”… companies that just need to survive six years. The VC / Ecosystem-Builder Dissonance: An ecosystem builder is measured on jobs and revenue creation, not outlier exits.The SPA Note, Decoded: A “Shared Profit Agreement” combines a SAFE capped at 3.6% of a $1M valuation with a shared earnings agreement. The Investor Pitch: Every LP dollar is matched by a donation. But the real sell is community impact.Applied Technology vs. Developing Technology: The program defines “tech-enabled” broadly. The Funding Runway: Approximately $225M is flowing into the region through HUD programs, with $17M dedicated to small-business grants. A Curriculum Built on Competencies, Not Basics: The accelerator is built around entrepreneurial competencies, including opportunity recognition, resilience, and network-building. The North Carolina Hallmark: “It’s not a zero-sum game. We’re all trying to grow the size of the pie.”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. Enjoy the conversation.Timestamps01:52 Scot's intro: SPAs, Asheville, and a new funding mechanism04:31 Meet Jeffrey Kaplan04:50 Asheville, the loading-dock office, and a Russian-nesting-doll of titles06:31 Jeffrey's background: Florida, intrapreneurship, and Anthware10:13 Eighteen months after Hurricane Helene13:14 The economic data: jobs, population, and a younger in-migration14:50 Is Biltmore Village back?17:31 The River Arts District rebound18:01 Asheville's startup ecosystem and why it's so CPG-heavy21:21 The Fresh Market CEO and the "buy local" effect22:42 Asheville's tech wins: Craft Peak, Sprin, Level.io, SDV24:40 How Optimist Ventures came to be25:19 The VC vs. ecosystem-builder cognitive dissonance27:03 "Moneyball the portfolio": singles and doubles27:36 The Dogwood grant and Ginger Frank's $100K call29:41 Splitting the fund: grants plus a for-profit vehicle30:26 The SPA note explained31:42 The shared-earnings math and negative 10% interest34:00 LP economics, the ~13% IRR, and private inurement37:10 The $855K HUD grant: funded for four years38:37 Inside the accelerator and "tech-enabled," broadly defined39:37 Carolina Flowers and the $40K freezer44:00 A curriculum built on entrepreneurial competencies46:27 What's next: bigger cohorts, applications June 347:56 Can this model scale to Charlotte or Raleigh?50:49 How the rest of the state can help Asheville52:42 The connector: Asheville's collaborative ecosystemWhere to Find Jeffrey: LinkedIn: https://www.linkedin.com/in/jeffdude/Front Porch Optimist Ventures: https://www.optimistventures.co/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.orgGold Sponsors: - Balentine: https://www.balentine.com/triangle-entrepreneurs - EisnerAmpner: https://www.eisneramper.com - Robinson Bradshaw:...
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    55 分
  • [REDACTED]: Episode 3: A Sentient HubSpot for $2 a Brand

    [REDACTED]: Episode 3: A Sentient HubSpot for $2 a Brand
    2026/06/03
    In episode 3 of [REDACTED], we (David and Taylor) run a live demo of an agentic CRM-cleanup pipeline (and finds out, on air, what it costs). We also walk through a landing page workflow that compresses what used to take five people and a month of meetings into something one person can do in an afternoon.The bulk of episode 3 is a live demo, just what we wanted. Plus, the best part of Redacted is that nothing is finished. Every episode is a midstream demo of something that might break, might cost more than it should, or might be the thing that quietly changes how a whole category of work gets done. Enjoy the conversation.What We Cover$1.98 to clean a brand: Taylor’s CRM pipeline ran live on air with one restaurant with two locations, 64 turns, 95% cache hit, total cost under two dollars. The code-vs-agent slider: Taylor built an interactive slider with pros and cons on each side. Fully deterministic code can’t handle ambiguity, fully agentic can’t be tested or priced. The “no brand graph” problem: There is no canonical source of truth for the restaurant industry. Google Places, SERP, and Yelp all return ranked top-20s — you can’t reconstruct the full graph locally. This is what makes the cleanup problem agentic by necessity.n8n’s flowers, n8n’s thorns: Taylor’s running joke is that every local agent he builds eventually looks like n8n. But debugging n8n at scale meant pulling down a million-token JSON dump every morning just to grep it. Local won on debuggability, not capability.Confidence tiers for copy extraction: “Act on it” = recurring in 6+ meetings. “Pattern” = 4–5. “Emerging” = 1–3. The model can suggest copy at any tier; the operator decides what gets shipped.The headline no human wrote: “Get found by foodies who are paying to find you.” This sidesteps the #1 objection in the space (is this a free deals site?) in one line. David says no one on his team has produced anything like it in ten years of writing copy.Claude Design as a brand harness: David came in skeptical that it was just a Claude Code wrapper. He left convinced: same model, but the design harness around it makes the outputs materially better.15–20 hours, one person: Total wall-clock on the landing page from raw transcripts to live wireframes. Historically the same work needed five people (founder, sales, copy, brand, design) and weeks of calendar time.Skill folder structure: David’s pattern for non-trivial skills: a tiny top-level skill file that orchestrates, plus subfolders for context (inputs the skill ingests), data (outputs by run), and prompts (exposed so they can be QA’d independently).Timestamps: 00:00 — Intro + choosing the Redacted logo live on air 03:22 — Taylor demos a “sentient HubSpot” CRM cleanup agent 04:37 — The messy CRM problem: duplicate restaurant brands & locations 05:23 — Running the AI pipeline live 06:07 — Why they moved away from n8n workflows 07:15 — Live cost tracking for AI agents 09:31 — “Architect agents” creating before/after CRM graphs 10:29 — The agent fixes HubSpot records autonomously 12:27 — The vision: a fully AI-maintained CRM 13:07 — Why every company’s CRM eventually becomes chaos 16:16 — Why HubSpot workflows can’t fully solve this problem 17:20 — The missing “brand graph” problem in restaurants 18:23 — Live demo success: AI cleaned the CRM in real time 19:52 — Human time vs AI time: CRM cleanup economics 20:27 — Code-driven vs agent-driven systems 21:56 — The tradeoffs of n8n vs local AI infrastructure 24:05 — When n8n still makes sense 26:57 — David’s AI-powered investor update workflow 29:17 — AI-generated shareholder updates with minimal edits 29:53 — Building AI-generated B2B landing pages 31:20 — Why landing pages are one of the hardest startup projects 32:07 — Mining 876 sales calls for “voice of customer” insights 33:11 — AI transcript tagging + metadata classification 34:14 — Extracting high-confidence marketing copy from sales calls 36:24 — Using Claude + Opus to synthesize a landing page 38:07 — First impressions of Claude Design 39:07 — “Get found by foodies who are paying to find you” 40:22 — Why the AI-generated copy shocked them 41:06 — How AI compresses cross-functional startup work 42:14 — Why positioning + copywriting still matter in AI 42:49 — The need for show notes + publishing workflows 43:31 — Closing thoughtsNew episodes drop twice a month/every other Wednesday. If you want to be on the show as a guest and show your [REDACTED] builds, email us: contact@tweenerfund.comShow notes from the episode: https://github.com/instanttaylor/redacted-podcastWhere 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...
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    44 分
  • Akash Ganapathi and Austin Kelleher, co-founders of Opine: Pivot the Plan, Not the Mission

    Akash Ganapathi and Austin Kelleher, co-founders of Opine: Pivot the Plan, Not the Mission
    2026/05/21
    This is a slightly different Tweener Talks. Akash and Austin are reflective founders. They think in frameworks, they read widely, and they’ve clearly spent a lot of time pulling patterns out of past wins and failures. So, we leaned in and made the episode less “tell me what you do” and more “tell me how you think.”Highlights CoveredFounder math: 5–7 months of zero salary, Costco bulk ramen, and a long-running Soylent habit dating back to Akash’s 2013 startup.Product-market fit is not binary: Akash and Austin use First Round Capital’s “Levels” framework and honestly place Opine between “developing” and “strong”, extreme PMF is when you can’t keep up with inbound demos.The inverse rule for co-founder debates: “Attack the person, not the idea” delivered as a straight-faced joke between three people who trust each other completely, with the real work happening in scrutinizing every argument from first principles.Two Amazon frameworks worth stealing: one-way door vs. two-way door decisions (Charlie’s favorite for cutting Akash off when he’s spending too long on something reversible), and disagree-and-commit (which they’ve barely had to use).Dev stack philosophy: Claude Max 20x for everyone (some engineers have more than one), agent-first development, Cursor BugBot finding bugs so reliably that engineers often skip local testing until BugBot signs off, and a north star of every engineer with one agent running 24/7.The go-to-market stack: Clay for top-of-funnel research agents, HeyReach for LinkedIn sequencing, AirOps for SEO content.Culture by osmosis, not documentation: No values poster on the wall. Instead, Austin’s personal framework, “you can increase your luck”, and the pay-it-forward principle as load-bearing parts of how the company actually operates.The best thing about being a founder is that no matter how many times you’ve done it, you learn something new every time, and Akash and Austin sent us home with a whole new reading list. Enjoy the conversation.Timestamps: 00:00 Cold open — Akash on pivoting the plan, not the mission00:40 Welcome & sponsor reads02:00 Scot's intro: why this episode leans into founder lessons04:15 Meet Akash Ganapathi and Austin Kelleher of Opine05:02 Akash's background — Trill AI, dropping out of UNC, JupiterOne08:53 Austin's background — Penn State, Interactive Intelligence, eBay, JupiterOne10:50 How Scot got to know Austin (and shout-out to Melinda)14:17 Founding Opine — bars, beers, and laptops after work15:46 Quitting JupiterOne with no salary — Soylent, ramen, and a supportive spouse18:01 The first check: Scot's year-old promise to Austin19:21 The product-market fit journey and First Round's "Levels" framework22:50 Pivoting the plan without pivoting the mission26:16 How three founders debate without breaking the company30:48 Amazon frameworks: one-way doors, two-way doors, and disagree-and-commit34:36 What Opine actually does — the elevator pitch36:43 State of the business: 15 people, doubling revenue39:42 The go-to-market stack — Clay, HeyReach, AirOps44:57 The dev stack — Claude Max, agents running 8+ hours, Cursor BugBot50:30 Knowledge sharing, custom skills, and an NC-based engineering team53:17 On company culture: lived, not documented57:39 Austin's philosophy — you can increase your luck01:00:46 Wrap and creditsWhere to Find Everything:Akash Ganapathi: https://www.linkedin.com/in/akash-ganapathi/Austin Kelleher: https://www.linkedin.com/in/austinkelleher/Opine: https://tryopine.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.orgGold 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/
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