This week's episode is a special treat. Mark Rosenberg is the earliest and most "AI-pilled" founder in the Tweener portfolio, and this conversation covers two very different topics, but all based on ‘How I AI’.

The first part of the discussion is the backstory of how mark founded Hip Commerce and then we jump into how Hip eCommerce leverages AI across customer support, finance, the warehouse/fulfillment operations, and product engineering, often replacing whole SaaS tools in the process and super-automating the business. The second part is a fascinating experiment: a fully autonomous, agent-run mini venture fund Mark spun up "as a fun side project" that started funding companies, emailing real people, and trying to route around its own guardrails. There’s a mix of fascinating learnings and a cautionary tale of why it’s important whether you are OpenClawing or building your own agents, to make sure you have guardrails and a very tight sandbox.

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Who is Mark?

Mark Rosenberg is the founder, CEO, and now also CTO of Hip eCommerce, a company that builds niche marketplaces and communities for collectors. Mark has been in collectibles and e-commerce for almost exactly 30 years. Back in 1996, when eBay was first emerging, he started a business with his father buying and selling stamps on eBay.

He ran that for about a decade, then built BidStart, a marketplace that grew out of a want-list tool, which he sold in 2012 to Stanley Gibbons, the largest collectible stamp company in the world, based in the UK. That sale is what brought him to Raleigh; he chose the Triangle for its entrepreneurial spirit and talent. He left in 2015, and about a year later founded Hip eCommerce.

Mark has a computer science background and is once again hands-on, shipping features himself with heavy use of Claude Code. Hip eCommerce raised its seed in 2018, another round in 2019, and its Series A in 2020.

How we met…

I’ve known Mark for a long time. Hip eCommerce was one of the very first investments at Tweener Fund, and I also invested personally, before the fund came along, so I sit on Mark's board. I enjoy the show from both seats: watching what Mark builds, and watching the other board members' reactions when a demo lands ("Oh my God, this is magic"). We got to know each other better around Hip's 2018 seed raise, and my only regret is that he should have had Mark on the podcast sooner!

Listen/Watch Our Interview:

This episode comes in two parts. In the first, Mark walks through how Hip eCommerce uses AI across the business: customer support, finance, the warehouse, product, and even people management. Along the way he shares the real numbers and the guardrails he’s put in place so that AI can take action, not just answer questions.

In the second part, the conversation takes a turn into the experimental. Mark describes a side project he spun up “in about a day”: an autonomous, agent-run venture fund called Prompt Capital, where AI partners generate ideas, review pitch decks, and fund and build companies largely on their own. What started as a fun experiment quickly produced some surprising, funny, and occasionally unsettling moments that taught him a lot about where this technology is headed.

It’s 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. Enjoy the conversation.

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.

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📌 What’s Next

Subscribe to NC Tweener Talks for more conversations with North Carolina founders, operators, and builders shaping the future of the ecosystem. Paid subscribers help us keep creating more episodes, events, and founder-focused content across the state.

In the last 90 days, I’ve talked to at least 10 founders who have the exact problem illustrated above. They could raise their 1X-2X their pre-seed or seed round amount based on “I’d put in $X if you had a lead” - add those together and you’re there! But sadly it doesn’t work that way. You have to find that lead.

BUT FIRST!

🦞 The Claw Is Back!🦞

We’re back. After a ton of feedback from friends across the Triangle, we’re hosting our second OpenClaw meetup in RTP. If you want to speak, or have a topic you’re dying to see covered, jump in our Discord or email contact@tweenerfund.com.

RSVP on Luma → https://luma.com/ij8dbav1

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What Does a Lead Do? And Why Does Everyone Want One?

In VC-land the word ‘lead’ has a lot of meaning embedded in it. It includes some or all of these assumptions in the one term:

• Term setting - At it’s core, ‘lead implies’ that someone is setting the price and terms of the round. Most institutional VCs as leads implies a priced round, but in pre-seed/seed and angels lead can apply to SAFE and convertible notes as well.

• Large investment - the typical rule of thumb is that a lead will invest 33-50% of the round

• Governance - for priced rounds, wrapped in the ‘lead’ branding is the firm taking a board seat.

• Due Diligence - the lead is committing to performing due diligence on the company. For syndicated deals, this can introduce a perceived liability. e.g. if the company is up to something shady and the lead misses it, but another 2-6 investors come into the deal, what happens to the lead when this surfaces?

• Water carrying - finally implied in ‘lead’ for the institutional investor is that they are going to use the reserves to help bridge the company between rounds, support future rounds, and stay at pro-rata (if they are pleased with the progress).

Understanding Venture Capital Structure

Before we dig into why there’s a shortage of leads and how to support it. Let’s cover a couple of basic structural elements of institutional VC that drive the upstream trends causing a lack of Leads.

What’s an LP?

In VC-land you’ll hear the two-letter acronym - LP - Limited Partner. Here’s a graphic that describes it:

in other-words, the VC has investors and those investors are called LPs. Some of these are individuals, some are Family Offices, most, from a $ perspective are huge pools of capital in pension funds, insurance capital, endowments, and foundations.

How Does Venture Fund-Size Impact Founders?

As a fellow founder, I have to admit, this took me a long time to understand and even realize I had to really understand a couple metrics of the firm I was pitching or it was a waste of time. At the end of the day the math starts at ‘fund-size’.

I this table, we take the fund size and:

• Set aside 50% of the fund for reserves

• That leaves 50% for fresh investments, what I call First Round Capital

  • Note: this used to be 25-30% but over the last 5yrs VCs have been increasing it due to the lack of reserves.

• Then we have a range of 10-15 companies per fund that VCs invest over the investment phase of the fund.

Looking at a range of fund-sizes, you can see that the average check size for 10-15 yields a range of $650k-$1m up to larger numbers. This is handy because if you’re raising a $5m seed - a $20m fund is too small and a $250m fund is out of your range.

Therefore, the most data points as you’re looking to find a lead is ‘what’s your fund size’. Crunchbase and online research can help you narrow this down quickly.

The other thing first-time founders don’t think about is ‘target ownership’. When a VC leads a round, they are typically trying to get to at least 20% in earlier rounds and in later rounds they will consider 15%.

Here if you are doing a $2m seed and you want a lead to invest $2m, that’s implying a $8-11.3m valuation.

You can’t for example, raise $1m on a $10m pre-money - that math doesn’t math with institutional VCs.

For a tactical example, here’s the progressio of the three local Triangle funds:

Bull City Venture Partners (Durham)

• Fund I — ~2010–2011, $15M

• Fund III — June 2014, $26M

• Fund IV — May 2022, $53M

Cofounders Capital (Cary)

• Fund I — June 2015, $12M

• Fund II — April 2018, $31M

• Fund III — March 2023, $50M

IDEA Fund Partners (Durham/Chapel Hill)

• Fund I — 2007–2008, ~$20M (targeted $25M)

• Fund II — January 2015 close

• Fund III — May 2019 close, ~$25M

Using this math on the BCVP and Cofounders $50m fund:

• $25m first rounds

• $1.7m-$2.5m checksize

• That’s leading $3-5m rounds

• $3m implies $12-$17 pre-money

• $5m implies $20-$28m pre-money

At $25m IFP:

• $12.5m first rounds

• $830k-$1.25m check range.

• $830k implies $3.3m pre-money

• $1.25k implies $5m pre-money

There are always exception to the rule, but hopefully this helps you think through how to best identify a target lead and how to craft your round to improve your chances of landing a lead.

Where Did All the Leads Go?

With that backgrounder, first for most pre-seed and many seed rounds, the local institutional firms got larger which, using the math above has priced them out of many early rounds.

Looking at the broader market, one outcome of companies staying private longer and M+A being somewhat frozen, has caused a liquidity crunch:

Here you see that LPs have been investing in firms and not getting distributions from exits since 2021. That’s a 5yr severe deficit in capital expected by LPs.

The good news is with the IPO filings of SpaceX, OpenAI and Anthropic each of those firms are going to raise $50-100b each at > $1T valuations. After the lock-ups that’s $3T in liquidity flooding back to LPs. Hopefully this will work it’s way back into new funds and fresh capital looking to deploy it into early stage NC companies!

Found More Leads - in secondaries!

Another downstream challenge with companies staying private longer:

The chart above shows that venture funds are increasingly buying their ways into unicorns by buying secondary offers. Every time this happens, a fresh round isn’t done, instead the big unicorn/decacorn companies (stripe, databricks, etc.) soak up the capital into bigger and bigger companies.

What can I do TODAY?

That gives us some of the reasons, what about the remedies, what can you do to increase your changes of getting a round done.

Flush out a lead as fast as possible

For institutional investors, when someone says they want to invest a largish amount (25-50% of the round size you’ve articulated), but after you get a lead, what they are saying one of two things:

1. They like the deal, but don’t have conviction to commit to lead and use one of their ‘10-15’ shots on goal.

2. They don’t want to tell you ‘no’ and if you get a lead they can always reconsider.

Your job as founder is to get to the bottom of this. One strategy, especially if you have a solid ‘plan B’ is to press a bit and ask some qualifying questions. It’s best to have these ready should they give you the “We’d like to invest, let us know when you have a lead…” Here’s some questions you can use that fit the situation. The goal is to get any more information out of them you can:

• “Any feedback you can share as you and the other partners evaluated the opportunity?”

• “When we get a lead, what were you thinking as far as range of investment to help us put the round together?”

• “From a lead perspective, would guidance on valuation help get you over the hump on leading?”

• “Great, can you give me some of the reasons you wouldn’t lead so I can work on getting you through those?”

If that doesn’t work, you can just say something like: “What would it take for your to lead. If all that falls through, time to move on to B1.

Execute Plan B1 - Get an Angel to Lead

Angels have a lot more flexibility to lead rounds and at the pre-seed/seed level, angels tend to be open to SAFEs which reduces the long list of ‘lead responsibilities’ to ‘setting terms’ - SAFEs strip away the governance, Due Diligence and water carrying. Friendly angels have kick-started many a round by setting prices, committing a first check and getting the ball rolling.

If that doesn’t work, time for Plan C→

Execute Plan C - Company Sets Terms

In the absence of a lead - institutional or angel there’s no rule that the company can’t set your own terms. I recommend putting your price on the low side of your range to entice investors (note we published data on these ranges back in this piece, this has not changed materially since the 12/25 publication date). In addition to lowering the price, you should also start as low as gives you 12-18months of runway - both to manage dilution and these ‘community rounds’ have a way of getting rolling. I’ve seen many start at $500, then grow to $750 and finally the founder cuts it off at $1m. It’s easier to raise the amount you’re raising (no savvy investor ever got mad that an early stage company raised more capital than initially discussed!) than it is to raise less. Starting small and raising creates momentum, buzz and excitement and hopefully a little FOMO. A large round sitting around not getting nibbled on has the opposite impact.

Summary

Let’s face it, fundraising in NC is hard. It’s been especially tough in the last 2yrs as the lack of leads has caused many startups to never close a round, even when they had the round committed but couldn’t land a lead. Hopefully, understanding where the leads have gone and providing some tips on how to find your lead, and get the round done. Good luck out there!

Before we jump in, shout out to our sponsors! 👇 None of this would be possible without them 💪🏻

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🦞 Tweener News: The Claw Is Back!🦞

OpenClaw Meetup #2 — RTP this time…

We’re back. After a ton of feedback from friends across the Triangle, we’re hosting our second OpenClaw meetup in RTP.

Whether you’re already running an OpenClaw agent, just curious what it can do, or building something with agentic AI, this is your crew. Come grab a drink and geek out with us.

Agenda:

• 4:00 – 4:30 — Arrive & settle in

• 4:30 – 6:00 — Lightning talks

• 6:00 – 7:00 — Q&A, open discussion & networking

We’re still putting the content together, and we want to hear from YOU. If you want to speak, or have a topic you’re dying to see covered, jump in our Discord or email contact@tweenerfund.com.

If you missed the first one, we have three videos from those presentations to give you a feel for the range beginner to expert.

⚠️ No livestream! this is IRL only. Block off your calendars now.

RSVP on Luma → https://luma.com/ij8dbav1

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📅 Events Around the State

A loaded few months across NC. Here’s what’s on our radar:

• June 8–12 — Charlotte Fintech Week

• June 10 — Fintech & Insurtech Generations

• June 10 — PitchBreakfast Charlotte

• June 11 — The Revvy Awards

• June 13 — GRINDfest 2026

• June 18 — SYNTHESIZE: A Juneteenth Celebration of Innovation and the Power of Community

• June 19 — Juneteenth at Hub RTP

• June 30 — NC TECH Awards Application Deadline

• June 30 — Joules Accelerator Application Deadline

• July 6 & July 13 — WEBB Squared: Build Financial Confidence

• July 15 — ConvergeSouth Startup Exhibitor Application Deadline

• July 27–28 — Future Grid 26

• August 27–28 — ConvergeSouth

🔍 What Stuck With Us This Week

Karpathy: From Vibe Coding to Agentic Engineering

Andrej Karpathy (OpenAI co-founder, former head of AI at Tesla, now founder of Eureka Labs) sat down with Sequoia’s Stephanie Zhan at AI Ascent 2026 to revisit “vibe coding” a year after he coined it. A few things that stuck with us:

• He’s never felt more behind as a programmer and why that’s exactly the point.

• Agentic engineering is the more serious discipline taking shape on top of vibe coding.

• Don’t think of LLMs as animals, think of them as ghosts: jagged, statistical, summoned, and needing real taste to direct. You can outsource your thinking, but never your understanding.

👉🏻 Watch here

Are You Just a .md File?

Right on theme: Death by Clawd — “The SaaSpocalypse Survival Scanner.” A tongue-in-cheek tool that asks the question every founder is quietly wondering. A few things that stuck with us:

• It scores whether your SaaS could be replaced by a single Claude Skill, a humble little .md file.

• Equal parts funny and uncomfortable, depending on what you’re building.

• A genuinely useful gut-check on where your real moat actually lives.

Check it out: https://deathbyclawd.com/

The End of the Funnel

Rob May (Investing in AI) makes a sharp argument that pairs perfectly with the agentic theme: the 30-year obsession with UX is ending, because agents don’t use your interface, they hit the API and skip every screen you designed. What replaces it is HX, or “Harness Experience.” A few things that stuck with us:

• The job shifts from driver to director: you stop operating the tool and start managing it like a talented employee.

• Good HX rests on three pillars: steerability, auditability, and clean intervention points.

• He maps five places the value lands for investors from agent audit infrastructure to the “Figma of HX.”

Worth the read 👉🏻 investinginai.substack.com/p/the-end-of-the-funnel-why-hx-is-the

You Need Better Storytelling

Kyle Poyar (Growth Unhinged) on a trend founders shouldn’t sleep on: storytelling has quietly become one of the most in-demand skills in tech, with US LinkedIn “storyteller” posts doubling last year. A few things that stuck with us:

• The signals are real: Anthropic posted a $300K+ Head of GTM Narrative role, and OpenAI is backing a tech talk show.

• Why now: attention is scarcer than product, traditional media keeps collapsing, and AI-flooded noise means only the best rises.

• He lays out five storytelling archetypes for 2026, Advocate, Analyst, Teacher, and more, to find your lane.

Find it here: https://www.growthunhinged.com/p/you-need-better-storytelling

🤝 Asks: How You Can Help

A Founder Needs Host Locations

Nearby Nearby Network is looking for host locations in Charlotte, Raleigh/Durham, and two stops on the coast. Each event is a public community conversation about disaster preparedness, resilience, and understanding what rural communities actually need before, during, and after a crisis.

If you (or your org) have a space and a real connection to your community, they’d love to hear from you. Reach out to Rhonda Jean directly at Rhonda@nearbynearbynetwork.org.

And honestly, this rolls in nicely with our last podcast. We just sat down with Jeffrey Kaplan of Optimist Ventures and Venture Asheville on rebuilding Asheville after Helene and his novel funding mechanism, the SPA note.

Same through line: communities figuring out resilience and recovery from the ground up. If you missed it, give it a listen, and then go help Rhonda find a spot.

Hiring? Looking?

There are fresh openings on the Tweener hub! Founders, if you’re hiring or looking, start here:

Tweener Hub Job Board → https://www.tweenerhub.com/job-board-20

Final Thoughts

We’re bringing you more reads, more ecosystem news, and whatever we’ve been cooking up at Tweener. Block your calendar for OpenClaw #2 🦞 and we’ll see you next week!

This week we sit down with Jeffrey Kaplan, CEO of Optimist Ventures and Director of Venture Asheville, to dig into one of the most unusual funding mechanisms we’ve come across: the SPA note.

It’s roughly a third company-talk (how Asheville’s startup ecosystem works and how it’s recovering from Hurricane Helene) and two-thirds founder-and-funder lessons (why VC math doesn’t fit an ecosystem builder’s job, and how Jeffrey designed a fund to back “singles and doubles” instead of swinging for unicorns). If you’ve ever wondered what comes after the SAFE note for Main Street businesses, this is the episode.

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Loving our content? It wouldn’t be possible without our amazing sponsors and our paid subscribers, so THANK YOU!

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And special thanks to our friends at Walk West for partnering with us to produce this pod!

Who is Jeffrey?

Jeffrey Kaplan earned his master's in entrepreneurship at the University of Florida, where he stayed on at the entrepreneurship center running co-curricular programs (a disabled veterans program, a women's entrepreneurship summit, a business plan competition, a student incubator) and TA'ing graduate and undergraduate courses.

He's had a couple of startups of his own, one in Charlotte, one in Asheville where"one did okay, one was a pretty big failure", but says he's learned he thrives more on the intrapreneurship side, with structure, accountability, and a budget, as long as the institution lets him be entrepreneurial.

After moving to Asheville, he worked at the software development agency Anthware under John Jones before landing at Venture Asheville, where he's now been eight years. At Venture Asheville he runs the Elevate mentorship program (built on MIT's Venture Mentoring Service), the financing initiatives, and the ecosystem events.

How we met…

Jeffrey has been a key connector for the NC Tweener Fund's statewide expansion. When the fund became the North Carolina Tweener Fund in February, Jeffrey helped me and the team get to know the startups out west. Think: Asheville, up into the Boone area, and beyond, and has sent a steady stream of great companies our way.

Listen/Watch Our Interview:

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.

Highlights

• Moneyball 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.

Visit Tweener Talks to listen for all audio podcast players

We have a video version on YouTube (make sure to subscribe!)

📌 What’s Next

Subscribe to NC Tweener Talks for more conversations with North Carolina founders, operators, and builders shaping the future of the ecosystem. Paid subscribers help us keep creating more episodes, events, and founder-focused content across the state.

We need help with upcoming episodes! Who's the most underrated AI builder you know? Someone running real systems inside a real business? Send us a message at contact@tweenerfund.com because we want to get them on the show!

What’s Redacted?

[Redacted] is a YouTube-first, twice-monthly show where we:

• Walk through what they actually shipped that week

• Screen share real systems inside their business

• Break down what worked, what didn’t, and why

Episode 3

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).

How to watch:

It’s best viewed on YouTube to fully see the examples (make sure to subscribe!)

But also available on all audio podcast players through Tweener Talks!

PLUS we have a new spot for show notes and files discussed in the episode. Check cit out: https://github.com/instanttaylor/redacted-podcast

What’s Next?

New 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 here.

This week on NC Tweener Talks, Scot sits down with two of the three co-founders of Opine, a Research Triangle Park startup building an AI-native context layer for revenue teams.

About a quarter of the conversation is about what Opine does. The other three quarters is a master class in founder lessons: how to pivot without losing your mission, how to argue with your co-founders without breaking the company, and how to build an engineering org where agents run for 8+ hours at a stretch (TokenMAXXING For the Win! 💪 💪 💪)

Subscribe now

We couldn’t bring you 100% original founder-to-founder content like this without the support of our awesome-sauce sponsors:

Loving our content? It wouldn’t be possible without our amazing sponsors and our paid subscribers, so THANK YOU!

Featured Platinum Sponsor

Featured Gold Sponsor

Featured Silver Sponsor

And special thanks to our friends at Walk West for partnering with us to produce this pod!

Opine’s DNA…

Akash Ganapathi is the CEO and co-founder of Opine. He’s a second-time founder; he dropped out of UNC Chapel Hill in 2013 to start Trill AI, a deep-learning startup selling risk signals to quant hedge funds. After Trill reached its “natural conclusion,” he spent three years as the first solutions architect at JupiterOne, the local cybersecurity unicorn.

Austin Kelleher is a co-founder of Opine and runs much of the technology side. A Penn State CS grad, he moved to North Carolina out of college to work at Interactive Intelligence (later acquired by Genesys), then spent time at eBay working on open-source software before joining JupiterOne as one of its earliest engineers. Along the way he built a game with over 100,000 users, a hint at his appetite for building things early.

Their third co-founder, Charlie Duong, also came from the JupiterOne crew. Austin and Charlie have known each other for over a decade.

How we met…

I got to know Austin during the eBay years, back when Austin was dating Melinda, who happened to work at Spiffy (Melinda is now Austin’s wife. I told her to make sure she knew what she was getting into.)

Akash entered the picture once he and Austin connected at JupiterOne. A year before Opine even existed, I told Austin: “If you ever leave to start a company, I want to be the first check in.” Austin said okay. A year later an email arrived, and, as a man of my word, the Tweener Fund wrote the first check into Opine’s $2M pre-seed.

Listen/Watch Our Interview:

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 Covered

• Founder 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.

How to watch:

Visit Tweener Talks to listen for all audio podcast players

We have a video version on YouTube (make sure to subscribe!)

📌 What’s Next

Subscribe to NC Tweener Talks for more conversations with North Carolina founders, operators, and builders shaping the future of the ecosystem. Paid subscribers help us keep creating more episodes, events, and founder-focused content across the state.

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Recap: What Happened to Tweener Talks?

Earlier this month we launched [Redacted], a new podcast under the NC Tweener Talks network.

This podcast shows you the messy middle of how AI is made and tested. As we made some of the first episodes, we learned that we frequently had personal information and business secrets on screen. Instead of deleting that par…

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After Tweener Madness, we’re back to regular programming with a special conversation featuring Marc Minor, CEO & Co-Founder of Higharc.

Higharc is one of the Triangle’s most compelling growth-stage companies, building AI-powered software for home builders. The platform helps builders move from design to sales to construction by generating homes in 3D, producing construction documents, estimating data, and buyer-facing sales experiences directly from a generative model.

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We couldn’t bring you 100% original founder-to-founder content like this without the support of our awesome-sauce sponsors:

Loving our content? It wouldn’t be possible without our amazing sponsors and our paid subscribers, so THANK YOU!

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And special thanks to our friends at Walk West for partnering with us to produce this pod!

Marc Minor: One of the Best Story Teller Founders You will Ever Meet.

One of the reasons I was especially excited for this conversation is because I consider Marc one of the best storytellers I’ve met. Beyond Tweener being an investor in Higharc through NC Tweener Fund, I have spent time with Marc over the years and consistently walked away impressed by how clearly and compellingly he explains complex ideas. The Higharc pitch deck is the best deck I’ve ever seen, bar none.

Throughout the episode, you’ll notice I repeatedly point out that Marc’s ability to tell a story, whether in fundraising, product vision, or company strategy, is a major part of what makes Higharc so compelling. It’s not just about the technology itself, but how Marc paints a picture of the future in a way founders can learn from.

When you listen/watch this one, see i fyou can decode the techniques he’s using.

Listen/Watch Our Interview:

In this episode, Marc talks about the long road to building fundamental technology, why Higharc spent years developing before going fully to market, how he found his co-founders, what he learned from early fundraising, and why AI has become a major tailwind for the business.

Highlights Covered

• How Higharc applies advanced manufacturing concepts to homebuilding

• Why the company spent four years building before going to market

• How Marc raised Higharc’s first $4.7M seed round

• Why founders need confidence, conviction, and a willingness to ask

• How Higharc thinks about spatial AI and proprietary data

• Why “buildings as data” is a major competitive advantage

• What founders can learn from great storytellers

• Why peer groups are so valuable for CEOs

If there’s one takeaway from this conversation, it’s that great companies are rarely built overnight, but clear vision, strong storytelling, and relentless execution can take you a long way.

How to watch:

Visit Tweener Talks to listen for all audio podcast players

We have a video version on YouTube (make sure to subscribe!)

📌 What’s Next

NC Tweener Talks is all about learning directly from the people building companies here in North Carolina, from early experiments to scaling teams, raising capital, and finding product-market fit.

In upcoming episodes, we’ll keep sitting down with founders across the state to unpack the real stories behind their companies: the pivots, failures, breakthroughs, and lessons they picked up along the way.

Subscribe to NC Tweener Talks for more conversations with North Carolina founders, operators, and builders shaping the future of the ecosystem. Paid subscribers help us keep creating more episodes, events, and founder-focused content across the state.

Introducing Our Tweener Claw Discord Community

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Michael Tavani is the CEO and Founder of Switchyards, a fast-growing “neighborhood work club” concept redefining how people work outside the home. Based in Atlanta (woahhhh, what???) Michael has spent his career building consumer-focused startups at the intersection of design, brand, and real-world experiences, one of the toughest corners of startup land.

What?! Someone From Atlanta on our NC Founder Pod!?

We don’t break the NC-only rule often but when we do, there’s a good reason. Switchyards isn’t just an Atlanta story anymore. It is expanding into Raleigh and already operating in Durham, so Michael Tovani is building right here in the Triangle. That makes this one very much a local story.

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We couldn’t bring you 100% original founder-to-founder content like this without the support of our awesome-sauce sponsors:

Loving our content? It wouldn’t be possible without our amazing sponsors and our paid subscribers, so THANK YOU!

Featured Platinum Sponsor

Featured Gold Sponsor

Featured Silver Sponsor

And special thanks to our friends at Walk West for partnering with us to produce this pod!

A sneak peak inside Raleigh’s Switchyard

Listen/Watch Our Interview:

In this episode, Michael unpacks the story behind Switchyards. We dive into why Michael chose one of the hardest startup paths (consumer + physical), how he built a moat through difficulty, and why investors had to physically visit a club before writing a check.

With Switchyards expanding into Raleigh, this conversation is especially relevant for founders thinking about category creation, brand, and building in the real world.

Highlights Covered

• Why “coworking” is the wrong label: Switchyards positions itself as a consumer product, not office space, a “neighborhood work club” designed for flexibility, not full-time desks.

• The hardest startup combo: consumer + physical: Michael intentionally chose a path with high barriers to entry, creating long-term defensibility once scaled.

• Work is becoming a consumer decision: The shift from assigned offices to choice-driven environments was clear even pre-COVID and Switchyards was built around that insight.

• The “third place” opportunity: Not home, not office, Switchyards fills the gap as a social, productive environment people actually want to use.

• Fundraising lesson: make investors feel it: Switchyards requires in-person experience—every serious investor had to visit a location before investing.

• From unfocused to obsessed: Early versions of the business tried to do too much. Growth came from narrowing down to one clear concept and executing relentlessly.

Switchyards is a reminder that some of the biggest opportunities are in rethinking the physical world, one neighborhood at a time.

How to watch:

Visit Tweener Talks to listen for all audio podcast players

We have a video version on YouTube (make sure to subscribe!)

✨Exclusive Offer✨ For Paid NC Tweener Times Subscribers

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First, we highlighted 2025 Triangle Tweener companies that executed on the top exits and fundraising rounds (note: the awards are backwards looking so this…

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Today, we’re launching something new under the NC Tweener Talks network. It’s called [Redacted]. One of our most popular episodes recently was our two parter from Feb 12th where David Shaner showed us how he has automated big portions of Offline with AI:

After that episode - I said to David, you’re a natural at this, you should do a new podcast series fo…

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On April 9th we hosted the Triangle’s first OpenClaw meetup (more info here).

We had well over 100 attendees come to hear 4 OpenClaw experts share their experiences and learnings, and this week we’re featuring Ryan Eade!

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Good Morning NC Builders! I hope everyone is recovering from RDSW, we’re finally digging out of a huge avalanche of emails and work that piled up while we were busy networking, talking, volunteering and RDSW’ing with everyone - what an amazing week.

As part of our activities, I was invited to speak at the Strategy talk about Competitive Moats in the AI …

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We had well over 100 attendees come to hear 4 OpenClaw experts share their experiences and learnings. It was really invigorating to see this many people that were completely and absolutely Claw Pilled and ClawMAXXing on one room. Everyone’s jaws dropped when an 11 year old started talking abo…

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The offic…

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Tweener Madness would not be possible without our awesome sponsors.

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Tweener Madness would not be possible without our awesome sponsors.

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Q1 marked a fundamental shift in the future of the Tweener Fund.

We announced a strategic partnership with NC IDEA, and changed the fund from the chrysalis from, Triangle Tweener Fund to it’s new form: NC Tweener Fund.

This partnership includes:

• $4M committed over 5 years

• Expansion beyond the Triangle to cover the whole state→ Charlotte, Wilmington, Triad, Mountains, and beyond

• A significantly larger pool of companies and opportunities and capital to deploy 🔥

Why now? We’ve effectively covered the Triangle “tweener” market:

• ~300 companies on the Tweener List

• ~100 bootstrapped (not raising)

• ~40–50 too late-stage for our model

• Leaving ~150–200 investable companies → most already in our portfolio

The NC state-wide expansion unlocks hundreds of new investable companies across the state and dramatically increases our long-term upside.

As shared in the Q1 LP meeting:

“We incubated this in the Triangle, it worked very well, and now we’re ready to take it statewide.”

Check out the ✨official✨ announcement here!

Thank You, LPs 🙌

Before we jump into the recap: thank you to our investors! This milestone doesn’t happen without you. With your support: We’re approaching $12M invested across 170+ companies, while maintaining a ~10% failure rate, far below traditional VC benchmarks

Always open for new investors/LPs!

Do you want to join with our 200 lifetime Limited Partners (or LPs, what we call our investors in VC) in helping us support NC startups? We’re structured as a rolling fund, which means, unlike closed funds that only let investors in every 5-10 years, we are ‘always open’ for new LPs. Here’s the details:

• Must be an accredited investor - SEC rule, not ours

• 1yr commitment, $30,000 for the year or $7,500/Q

• 1% management fee, 20% carry and a small AngelList administrative fee

For more details - visit www.tweenerfund.com where you can see our pitch and hit the invest button to get started!

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

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Our amazing sponsors have also put out an official Q1 press release here, check it out!

Q1 Investing Highlights

Our Tweener Fund Q1 2026 Snapshot:

• $700K invested

• 14 total investments

  • 7 new

  • 7 follow-ons

• 10 tweeners / 4 pre-tweeners

What stood out this quarter?

1. Statewide deals are already happening

• Investments in Winston-Salem, Wilmington, Charlotte

• Early proof that expansion is working immediately

2. Stronger mix toward “true Tweeners”

• After feedback, we’re leaning more heavily into later-stage, revenue-generating companies

3. Fundraising environment improving

• More priced rounds returning

• Less reliance on SAFEs as bridge capital

• Early signal: market thawing

New Portfolio Companies

• Beam Dynamics (PT) - Operating system for managing enterprise physical assets, compliance, and lifecycle data. (Winston-Salem)

• BEAMRaiL (PT)- Building public safety intelligence platform. (Cary)

• Lucid Bots (T)- Builds drones and software for automated cleaning of large structures like parking garages. (Charlotte)

• NeuroTech Insights (PT)- AI platform combining gait and cognitive analysis to measure brain-body function for clinical care. (Wilmington)

• OOGA Technologies (T)- NDT (Non Distruptive Testing) platform connecting organizations with experts and AI tools for faster, reliable inspections. (Cary)

• Skillmaker (PT)- AR platform upskilling blue-collar mechanics to address national workforce shortage. (Carolina Beach)

• Spidr (PT)- Unified API platform providing payment processing, KYC, and fraud monitoring infrastructure. (Charlotte)

Also, Tweener Fund made additional investments in 7 portfolio companies:

• Futureproof Ops (PT) - AI-powered financial operations platform for startup bookkeeping and cap table management. (runfutureproof.com)

• Truentity (T) - AI platform enabling community pharmacies to offer clinical services and generate revenue.

• Keebler Health (T) - GenAI platform accelerating insurance claims coding and processing.

• Blue Sky Robotics (PT) - AI vision systems and robotics for warehouse and hospital automation with 50% labor savings. (crunchbase.com/organization/blue-sky-robotics)

• Arpio (T) - Cloud-aware disaster recovery software for business continuity.

• Cycle Labs (T) - Testing platform helping retailers validate new warehouse management system implementations.

• Troupe AI (PT) - AI platform measuring and optimizing go-to-market messaging performance across channels.

Q1 Tweener Events

Q1 was one of our most active quarters on the community side. Our Q1 event was the LP + Founder Happy Hour at Ruckus. With the close knit crew we enjoyed the amazing weather and had some high-quality conversations.

Other Key moments include:

• 2026 Founder Productivity Series (4 parts): one of our best-performing content series ever

  • Part 1: Productivity Hacks for Founders

  • Part 2: Founder Health Optimization

  • Part 3: GTM Tech Stack Playbook

  • Part 4: DevStack for Ludicrous PR-Production

• First Wilmington event at UNCW CIE

• Multiple NC IDEA shoutouts across podcasts and collaborations

• Tweener Madness now in championship the Fab 4 round!

Become a Sponsor

Would your company benefit from exposure to NC’s fastest-growing startups?

Our audience is made up of NC founders and operators, primarily at startups doing over $1M/year and many much larger. When a company hits Tweener status, they’ve got real traction, funding (usually), a growing team, and momentum.

Thanks to strong demand, we’re upgrading our sponsorship opportunities across Tweener Times, Tweener Talks, and more.

If you’re looking to connect with this high-impact community, now’s the time. Send us a message or an email to contact@tweenerfund.com.

Let’s build together!

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🙌 Thank You

This quarter marks a clear shift:

Before:

• Triangle-focused

• Limited deal pool

• Early-stage heavy

Now:

• Statewide platform

• Larger, more diverse pipeline

• Truer tweener-stage companies

• Stronger ecosystem integration

We’re entering the next phase of the fund:
👉 More scale
👉 More access
👉 More impact

From a strong investing quarter → to a statewide expansion that redefines the future of the fund.

We’re just getting started.

Tweener Madness would not be possible without our awesome sponsors.

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