In this special solo episode of Triangle Tweener Talks, Scot goes beyond the two-part Tweener Times report to walk founders through what the data actually means in practice. This episode exists for one reason: to give Triangle founders clearer goalposts, better context, and fewer surprises when they sit down to raise capital.
Tune in to hear:
Where to read each part:
Part 1: https://www.tweenertimes.com/p/part-iii-triangle-startup-venture
Part 2: https://www.tweenertimes.com/p/part-iiii-the-triangles-first-and
Where to Find Scot Wingo:
In this episode:
00:00 – 03:00 Why this data exists & the founder questions it answers
03:00 – 07:00 How the Tweener Fund dataset was built (and anonymized)
07:00 – 15:00 The origin of the Tweener List and index strategy
15:00 – 22:00 How funding stages are defined by company progress
22:00 – 35:00 SAFEs, convertible notes, priced rounds — explained
35:00 – 45:00 How deal structures change from Pre-Seed to Series A
45:00 – 59:00 Valuations, raises, and dilution by stage
59:00 – 1:07:00 What founders should actually do with this data
If this is your first time really digging into venture fundraising, you’ll hear a few terms that investors use casually but aren’t always obvious. Here’s a quick guide to the most common ones we reference in this episode:
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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.
We couldn’t share posts like this without our amazing sponsors:
Gold Sponsors:
Silver Sponsors:
2025 Sponsors:
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Triangle Tweener Talks is sponsored by:
In Part 2 of this two-part deep dive, Triangle Tweener Talks host Scot Wingo sits down with legendary Triangle founder Mike Doernberg to explore his journey on scaling multiple companies, spinning out new ventures, navigating private equity, and why he never left North Carolina.
Tune in to hear:
Where to Find Mike Doernberg:
LinkedIn: https://www.linkedin.com/in/michaeldoernberg/
PlayMetrics: https://home.playmetrics.com/
Where to Find Scot Wingo:
In this episode:
00:05 — Welcome to Part 2 with Mike Doernberg
00:12 — Coming back from “Home Depot retirement”
00:18 — The origin and explosive growth of ReverbNation
00:27 — Solving the cold-start problem before it had a name
00:33 — Building Promote.it → the foundation for Adwerx
00:42 — Spinning out Adwerx and structuring the deal
00:52 — Should Mike run a venture studio? Scott pushes him
01:00 — Why incubating ideas is easier than incubating founders
01:10 — The spinout challenge: talent dilution
01:15 — The path to PlayMetrics and modernizing youth sports
01:27 — Selling Reverb to focus fully on PlayMetrics
01:38 — Navigating private equity the right way
01:47 — How PE can empower (not suffocate) founders
01:55 — Running a 450-person org and learning a new leadership mode
02:03 — Why Mike stayed in the Triangle — and how the ecosystem evolved
02:16 — Triangle vs. Bay Area: culture, risk, and quality of life
02:30 — Final reflections & Scott’s challenge on a future venture studio
02:38 — Outro & sponsor thank-yous
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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.
We couldn’t share posts like this without our amazing sponsors:
Gold Sponsors:
Silver Sponsors:
2025 Sponsors:
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Triangle Tweener Talks is sponsored by:
In Part 1 of this two-part deep dive, Triangle Tweener Talks host Scot Wingo sits down with legendary Triangle founder Mike Doernberg to explore the earliest chapters of his career, from CPA to multi-exit entrepreneur.
Mike walks through the founding of Marathon, the rise of early PC-driven consulting, the creation and spinout of SmartPath, raising capital through the old-school angel gauntlets, navigating the DoubleClick acquisition, and why “retirement” lasted all of three months.
Tune in to hear:
Where to Find Mike Doernberg:
LinkedIn: https://www.linkedin.com/in/michaeldoernberg/
PlayMetrics: https://home.playmetrics.com/
Where to Find Scot Wingo:
In this episode:
01:02 – Mike’s early background & move to NC
03:30 – Becoming a CPA but wanting more
05:54 – Early exposure to startups at Ernst & Young
07:50 – Why entrepreneurship became inevitable
09:50 – Story of Burl Software and Y2K
12:10 – How Marathon was formed
13:22 – Rising PC adoption and early web consulting
14:51 – Early e-commerce and building internet applications
17:00 – How the GlaxoSmithKline project inspired SmartPath
19:06 – The power of deeply understanding a customer problem
20:34 – Building early commerce & workflow applications
23:40 – SmartPath as an early low-code platform
24:59 – Why selling SmartPath was his biggest mistake
26:00 – Raising venture in the 90s & 2000s
28:20 – The TIG pitching gauntlet
30:00 – A founder’s early-career fear of the unknown
31:10 – The SmartPath exit to DoubleClick
33:00 – Life at DoubleClick & post-acquisition changes
35:20 – Mike retires for 3 months (Home Depot era)
36:50 – Why founders struggle not to build
38:45 – The addiction and community of company building
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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.
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Triangle Tweener Talks is sponsored by:
Mark Flickinger is the COO and General Partner at BIP Ventures, one of the Southeast’s most active venture firms. Based in Atlanta, Mark brings a rare dual perspective, an operator who scaled startups before joining the investing side. Since 2015, he’s helped BIP expand from an Atlanta-centric firm into a major player across the Southeast and Midwest.
Every year, BIP Ventures releases its State of Startups in the Southeast report, arguably the most comprehensive snapshot of our region’s innovation economy. In this episode, Scot sits down with Mark to break down the 2025 findings, from AI and valuations to where the capital is really flowing.
Tune in to hear:
Where to Find Mark Flickinger:
LinkedIn: https://www.linkedin.com/in/mark-flickinger-24295538/
BIP Capital: https://www.bipcapital.com/
Where to Find Scot Wingo:
In this episode:
02:00 – Meet Mark Flickinger & the BIP Ventures origin story
05:30 – How the State of Startups report began
10:00 – What makes the Southeast data different
15:00 – Why the 2025 report matters
18:00 – Trends: AI, capital concentration, and valuation health
23:00 – The Southeast’s unique resilience
27:00 – North Carolina’s rise to #2 in regional investment
31:00 – Triangle Tweener Fund and other active players
37:00 – Atlanta’s current momentum and industry strengths
42:00 – What founders should take away from the data
46:00 – Closing thoughts and Mark’s advice for founders
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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.
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Triangle Tweener Talks is sponsored by:
From the world of tech startups to the high-stakes world of sneakers, Walk West CEO and founder Greg Boone is a serial entrepreneur with a unique journey. With a background in computer science and a history of building and investing in companies, Greg brings a fresh perspective on how to navigate the current "AI tsunami."
Tune in to hear:
Where to Find Greg Boone:
LinkedIn: https://www.linkedin.com/in/gregboone/
Walk West: https://walkwest.com/
Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo
In this episode:
(00:06:00) The evolution of Walk West from a marketing agency to a content studio.
(00:10:00) Greg’s "Four P" framework for business growth.
(00:16:00) Greg's entrepreneurial journey, including his background in computer science and his various ventures.
(00:23:00) A deep dive into sneaker collecting and the business of Michael Jordan.
(00:32:00) Walk West's growth and the importance of partnerships.
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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
What happens after you sell a company you helped turn around?
For Dr. Doug Kaufman, it’s a story of new ventures and hard-won lessons.
In this second part of a two-part series, Doug discusses his time at TransLoc, a mass transit technology company he helped lead to a successful sale to Ford.
He shares how he navigated a challenging acquisition process and the importance of a strong, collaborative board. He also talks about the challenges of his most recent venture, Belongly, including the difficult decision to pivot the business and raise capital in a shifting market.
Now, as a Duke professor, executive coach, and partner at an AI consulting firm, Doug offers insights on the critical importance of founder mental health and the power of vulnerability in leadership.
Tune in to hear:
Where to Find Dr. Doug Kaufman:
LinkedIn: https://www.linkedin.com/in/drdougkaufman/
Where to Find Scot Wingo:
In this episode:
(00:01:00) Dr. Kaufman describes how he got connected with TransLoc after leaving Spring Metrics. He initially thought "mass transit technology" was boring until a board member convinced him to talk to the founding CEO, Josh Whitten.
(00:06:00) Dr. Kaufman became the CEO and raised over $6 million in equity from investors like SJF Ventures and Fontinalis, and another $2 million in debt from Square One.
(00:11:00) Dr. Kaufman reveals that he and his team did walk away from the deal once.
(00:17:00) Dr. Kaufman describes the big idea behind Belongly as an effort to address the mental health crisis in young people
(00:28:00) Dr. Kaufman describes his specific type of executive coaching
(00:33:00) The conversation shifts to founder mental health.
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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
What happens when a classically trained psychologist leaves the world of academia to shift careers?
For Dr. Doug Kaufman, it was to become a serial entrepreneur (obviously).
Doug's story is defined by a relentless curiosity about human behavior, a series of successful ventures, and some hard-won lessons in the chaotic world of startups.
In this first of a two-part series, Doug recounts his unconventional path from a psychology PhD to joining a hyper-growth tech company, starting his own bootstrapped business, and facing the ultimate test of a founder's resilience in the Triangle.
Tune in to hear:
Where to Find Dr. Doug Kaufman:
LinkedIn: https://www.linkedin.com/in/drdougkaufman/
Where to Find Scot Wingo:
In this episode:
(00:02:00) Dr. Kaufman's lifelong fascination with psychology, human behavior, and the personal reasons for his interest.
(00:04:00) The decision to leave academia to start his first company, Alley Dog, and a computer repair side hustle.
(00:08:00) Joining Blackboard in 1998 and his experience in a hyper-growth tech startup.
(00:15:00) Why he left Blackboard to move to the Triangle and start his own company.
(00:18:00) Founding ClearTXT and navigating a major PR crisis at a large university.
(00:24:00) The lessons he learned from the chaos of startup life, including a patent troll lawsuit and a successful acquisition.
(00:29:00) The origins of Spring Metrics and joining the Triangle Startup Factory's first cohort.
(00:37:00) A frank discussion about his first board meeting at Spring Metrics and the difficult experience that followed.
(00:44:00) His eventual transition out of the CEO role and the valuable lessons he took from the experience.
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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
From her upbringing in Johannesburg, South Africa, to a career spanning Wall Street, an Ivy League MBA, and the early days of e-commerce, Ricci Wolman’s journey is a all about problem solving, resilience, freedom, and...the paradox of choice?
As the CEO and co-founder of Written Word Media, she has built a bootstrapped and profitable business by solving a problem her own mom faced: book discovery in a crowded market.
Tune in to hear:
Where to Find Ricci Wolman:
LinkedIn: https://www.linkedin.com/in/ricciwolman/
Written Word Media: https://writtenwordmedia.com/
The Flop.ai: https://www.theflop.ai/
Where to Find Scot Wingo:
In this episode:
(00:04:00) Ricci’s immigration from Johannesburg, South Africa and the major culture shock of moving to the US.
(00:11:00) Her path to Wall Street, working as an investment banking analyst at Bear Stearns, and leaving after 9/11 for a more impactful role.
(00:17:00) Running an e-commerce side hustle on a Yahoo store and the decision to get her MBA at Harvard Business School.
(00:24:00) The move to North Carolina and her career in e-commerce marketing at The Body Shop and Lulu Publishing.
(00:30:00) How her mom's self-publishing journey inspired the idea for Written Word Media.
(00:48:00) The birth of Free Booksy as a sandbox to test marketing and the accidental funding from the Amazon affiliate program.
(00:58:00) The decision to formally start the business with her husband, Ferol, who left ReverbNation to become her co-founder.
(01:04:00) The unique challenges of balancing the two sides of a marketplace business and keeping authors and readers happy.
(01:07:00) Ricci's bootstrapping philosophy and why she optimizes for "private barometers of success."
(01:14:00) Her new passion project, The Flop.ai, a newsletter to help demystify AI.
(01:18:00) Advice for founders on taking risks, choosing the right path, and leveraging the Triangle's supportive community.
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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
What happens when a North Carolina native, seasoned by Silicon Valley and Wall Street, returns home to build a company that marries profit with purpose? For Jason Massey, co-founder and CEO of Ndustrial, it's led to a 14-year journey developing cutting-edge technology that makes industrial facilities more efficient and sustainable.
In this episode, Jason shares his unique path, from a childhood in Mebane and studying physics and finance at NC State, to navigating the dot-com bubble in New York and the vibrant startup scene in Silicon Valley. He opens up about the "dysfunction" that birthed new companies from his own efforts and why he ultimately returned to his roots to build Ndustrial into a global leader in industrial energy management.
Tune in to hear:
Where to Find Jason Massey:
LinkedIn: https://www.linkedin.com/in/jasonmnc/
Ndustrial: https://ndustrial.io/
Where to Find Scot Wingo:
In this episode:
(00:06:00) Growing up in Mebane, North Carolina, and his path to entrepreneurship through Wall Street and Silicon Valley.
(00:13:00) The velocity of failure in Silicon Valley and his first exposure to clean tech.
(00:17:00) Returning to North Carolina and settling in Mebane with his family.
(00:20:00) The Tap Tap Revenge angel investment and the lessons learned.
(00:28:00) The serendipitous founding of Sustainable Industrial Solutions (SIS) and building foundational tech with NC State engineering students.
(00:37:00) The pivot from SIS to Ndustrial, focusing on industrial production data and the Coincident Peak breakthrough.
(00:45:00) Why Ndustrial embraces a hybrid model of SaaS and professional services, and their approach to hardware.
(00:49:00) Ndustrial's $26 million fundraising journey and the strategic value of corporate VCs.
(00:53:00) Dominating the cold chain market and its massive energy and sustainability impact.
(01:02:00) The value of being "Switzerland" in the energy markets and building a truly sustainable business.
(01:10:00) The significant AI play at Ndustrial, using LLMs for contextualizing data and enhancing user interfaces.
(01:15:00) Jason's commitment to mentoring and supporting the Triangle's entrepreneurial community.
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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
In Part 2 of our conversation with Eric Boduch, Pendo co-founder and CEO of Revcast, we explore the world of venture studios. Having left Pendo to pursue his vision of parallel entrepreneurship, Eric shares how his studio, 24 and Up, identifies, builds, and funds new companies.
This episode unravels the unique model of a venture studio, differentiating it from accelerators, incubators, and traditional venture capital. Eric also offers a candid assessment of the Triangle's startup ecosystem, highlighting its strengths and identifying key areas for growth.
Tune in to hear:
Where to Find Eric Boduch:
LinkedIn: https://www.linkedin.com/in/eric-boduch-a1b61/
24 and Up: https://www.24andup.com/
Revcast: https://www.revcast.com/
Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo
In this episode:
(00:00:03) Eric's plea: Entrepreneurs must buy from other entrepreneurs to build a stronger ecosystem.
(00:04:46) What is a venture studio? Eric breaks down his model for co-creating and funding companies.
(00:06:33) Why Eric chose the venture studio model over accelerators, incubators, or traditional VC.
(00:12:00) The birth of Revcast: from an internal Pendo idea to a revenue optimization solution.
(00:17:56) The origin of Wayfound: an AI play in agent performance management.
(00:21:47) Introducing Troop: leveraging AI for brand story consistency and improving win rates.
(00:24:34) Sesame: an external idea for a digital identity verification marketplace.
(00:26:17) Looking ahead: New ventures in social selling, e-commerce, and AI agent technology.
(00:28:30) Managing multiple companies and the strategic advantage of asymmetric information for early-stage investment.
(00:33:15) Building the 24 and Up team and the strategy behind raising more capital for the studio.
(00:36:13) Comparing the Raleigh and Pittsburgh ecosystems: strengths, weaknesses, and the need for "Pendo Mafia" spin-offs.
(00:43:56) The critical need for early-stage "YOLO" VC funds in the Triangle to back generational companies.
(00:49:32) The entrepreneur's responsibility to buy from other startups and foster local growth.
Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
This is Part 1 of Eric Boduch's story. Tune in next week for Part 2!
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Triangle Tweener Talks is sponsored by:
From co-founding one of the Triangle's most successful tech companies, Pendo, to quietly building a new venture studio, Eric Boduch has a deep well of entrepreneurial experience. In this first of a two-part series, Eric sits down with Scot to reflect on his journey, the lessons learned from the dot-com bust, and the evolution of product management.
Eric gets into his early days, his path to co-founding Pendo, and the strategic decisions that helped shape its unique brand and culture.
If you've ever wondered about the behind-the-scenes of building a high-growth startup and the critical role of product, this conversation offers invaluable insights.
Tune in to hear:
Where to Find Eric Boduch:
LinkedIn: https://www.linkedin.com/in/eric-boduch-a1b61/
Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo
In this episode:
(00:05:38) Growing up in Western Massachusetts, the home of Friendly's Ice Cream, and his early start in coding and sports.
(00:08:28) How Eric chose Carnegie Mellon for computer engineering and developed his entrepreneurial bug.
(00:12:22) The founding of Cerebellum with Todd Olson and the tough lessons from the dot-com crash.
(00:17:12) Post-Cerebellum ventures, including ProductSoft and his time at Embarcadero and Vitria.
(00:22:08) The timing challenges of Smash Technologies and the rise of mobile apps.
(00:25:19) The genesis of Pendo: from initial ideas with Todd Olson to the early days of building the product.
(00:28:46) Eric's role in Pendo's early marketing, the struggle to define a category, and the origins of the pink dinosaur brand.
(00:39:01) The rapid growth and culture-building at Pendo, including the challenges of scaling from 1 to 30+ employees quickly.
(00:41:44) His transition to leading Adopt (now Pendo for Employees) and the future of software usage.
(00:44:33) Eric's vision for Pendo as a $100 billion company and the critical role of product data in the age of AI.
(00:49:06) Why Eric was drawn to venture studios and why now felt like the right time to launch his own.
Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
This is Part 1 of Eric Boduch's story. Tune in next week for Part 2!
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Triangle Tweener Talks is sponsored by:
What happens when a seasoned entrepreneur spots a gap in the market and decides to take a risk on something entirely new? For Jason Widen, it’s led him from founding Raleigh Founded, a cornerstone of the Triangle’s startup ecosystem, to creating Blue Co. – a flexible warehouse solution designed for service-based businesses.
In this episode, Jason shares his journey of building community-driven businesses, from his early days working at a ski resort to launching Raleigh Founded and now expanding his vision with Blueco. If you’ve ever wondered what it takes to pivot, scale, and truly make an impact in your community, this conversation is packed with valuable insights.
Tune in to hear:
Where to Find Jason Widen:
Where to Find Scot Wingo:
In this episode:
(00:03:00) Jason’s early years and how a ski resort job sparked his entrepreneurial spirit.
(00:10:15) The start of Raleigh Founded, a co-working space that grew into a hub for Triangle entrepreneurs.
(00:18:00) The inception of Blue Co., a flexible warehouse solution for plumbers, electricians, and moving companies.
(00:26:30) Real-world lessons from Jason’s ventures, including the challenges of starting a restaurant and building a real estate empire.
(00:38:05) Scaling Blue Co. and Jason’s plans for expanding across the Southeast.
In the news:
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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
Chris Heivly’s journey through the tech world is one for the books, literally - thanks to his deep-rooted love of maps. From his early days studying geography and computer mapping to shaping the future of internet navigation with MapQuest, Chris shares an inspiring story of innovation, risk, and community-building.
In this episode, we explore Chris’s entrepreneurial journey, discussing everything from his time building map systems for the U.S. State Department to his pivot into founding one of the Triangle’s first startup accelerators, the Triangle Startup Factory.
Tune in to hear:
Where to Find Chris Heivly:
Where to Find Scot Wingo:
In this episode:
(00:03:00) Chris's love of maps and how it shaped his career from geography major to tech innovator.
(00:10:15) The breakthrough moment: from computer mapping to building mapping systems for the U.S. State Department.
(00:17:45) The story of MapQuest’s creation, why it was so ahead of its time, and how it revolutionized navigation.
(00:27:30) Chris’s time at Donnelly and the strategic decisions that led to MapQuest's success.
(00:38:05) The evolution from VC to accelerator: Chris’s journey building the Triangle Startup Factory and shaping the local ecosystem.
(00:46:52) Chris’s key lessons for startup founders and how to build a lasting legacy.
In the news:
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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
If you ask someone what’s at the heart of a successful engineering team, the answer might involve tools, talent, or tech. But Hersh Tapadia, CEO and co-founder of Allstacks, believes it all starts with one thing: measurable productivity. While we all know engineering teams face unique challenges, Allstacks is tackling the toughest one—how to measure and improve engineering productivity at scale.
In today’s episode, we talk to Hersh about his journey, from growing up in Raleigh to leading a company that's reshaping the way engineering teams operate. Hersh shares how Allstacks went from a consulting business to a product-driven company, the challenges of raising capital, and what he’s learned about engineering productivity in the process.
Tune in to hear:
Where to Find Hersh Tapadia:
Where to Find Scot Wingo:
In this episode:
(00:03:00) From Raleigh to Allstacks – How Hersh’s journey led him to build a product that’s changing the game for engineering teams.
(00:10:15) The Early Days – Raising capital, finding product-market fit, and making the leap from consulting to product development.
(00:17:45) The Allstacks Approach – How data can drive engineering productivity and why it’s more than just tracking output.
(00:27:30) Navigating the Tech Space – The challenges of scaling in the dev-tech world and the lessons learned along the way.
(00:38:05) The Future of Engineering Productivity – What’s next for engineering teams and how AI is shaping the way they work.
(00:46:52) Lessons for Founders – Hersh’s hard-earned wisdom on building a company, raising capital, and navigating the startup rollercoaster.
In the news:
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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
If you ask anyone about the entrepreneurial ecosystem in the Triangle, one name that keeps coming up is Dr. Tom Miller. Known as the champion of engineering entrepreneurship at NC State, Tom has been pivotal in shaping the region’s startup culture for over 40 years. From his early days in eastern North Carolina to founding the Engineering Entrepreneurs Program, his influence is felt across generations of entrepreneurs.
Today, we sit down with Dr. Miller to hear his journey, the creation of the Engineering Entrepreneurs Program, his work with students like Bill Nussey and Chris Evans, and his thoughts on the evolving role of entrepreneurship in education.
In this episode:
Where to Find Dr. Tom Miller:
Where to Find Scot Wingo:
In this episode:
In the news:
Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
Who will be crowned champion of Tweener Madness and take home the $25K investment from the Triangle Tweener Fund?
The championship features two radically different approaches to innovation:
ZW (Robert Fu)
InviteJet (Brian Watson & Paul Davis)
Selection Committee
Key Discussion Topics
🧠 ZW’s Highlights
📅 InviteJet’s Highlights
📌 Timestamps
(00:00:04) – Championship kickoff with Scot Wingo
(00:01:25) – ZW fields questions on product, AI architecture, and industrial go-to-market
(00:27:04) – InviteJet dives into scaling, technical differentiation, customer retention, and future roadmap
(01:02:47) – Selection committee debrief and reflections on both companies
So who wins? 🏆 Tune in to find out!
This episode wraps up the Tweener Madness series, where eight Triangle startups competed for a $25K investment and plenty of local bragging rights.
🎙️ Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
Who’s Advancing from the Fabulous Four - CivicReach or InviteJet?
Welcome back to Triangle Tweener Madness, the high-stakes startup tournament where eight companies go head-to-head for a $25,000 investment from the Triangle Tweener Fund!
We’re down to the Fabulous Four, and this week’s semifinal is a clash between a calendar-powered marketing platform and a voice AI company transforming local government services. Two bold visions. One coveted spot in the finals.
Let’s meet the contenders.
🔹 InviteJet (Paul Davis & Brian Watson) – A marketing platform that lets brands send calendar invites—yes, calendar invites—to their customers. With integrations into tools like Klaviyo and Mailchimp, InviteJet gives brands a new channel for time-based marketing. Early traction shows that calendar invites can outperform email when it comes to urgency and engagement, especially with unengaged audiences.
🔹 CivicReach (Chip Kennedy) – A voice AI platform built to modernize how local governments serve their residents. CivicReach helps cities and counties automatically answer incoming calls, reducing costs and relieving overworked staff. With integrations into CRMs and payment systems, CivicReach is on a mission to improve public service delivery—without increasing headcount.
🎤 InviteJet’s Pitch
🎤 CivicReach’s Pitch
Selection Committee
📌 Timestamps
(00:00:35) – Scot Wingo kicks off the InviteJet vs. CivicReach semifinal showdown.
(00:01:31) – InviteJet answers questions on market education, technical complexity, customer success stories, and pricing models.
(00:23:34) – CivicReach fields questions on ROI, government buying cycles, integration strategies, and its founding story.
(00:41:36) – Founders reflect on the mission, momentum, and long-term potential.
(00:43:12) – The selection committee deliberates.
(00:50:33) – One company advances to the Tweener Madness finals!
🎙️ Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
What if the most powerful tool for success as an entrepreneur isn’t the latest strategy or tech hack—but the way you perceive and process every challenge you face?
In this episode of Triangle Tweener Talks, guest host Rebecca Ross sits down with Katherine Krupka, a leadership strategist and executive coach, to dive into the powerful connection between leadership, perception, and decision-making. Katherine has worked with leaders around the world, from embassies to startups, helping them unlock deeper levels of wisdom and navigate uncertainty. She’s bringing all of her expertise to Raleigh Durham Startup Week as a keynote speaker, and she’s here to share a sneak peek of what attendees can expect.
You’ll hear Katherine discuss:
If you’re a founder or executive struggling with uncertainty and high-stakes decisions, Katherine’s talk is not to be missed at Raleigh Durham Startup Week on April 8th.
Key Takeaways:
Links Mentioned:
🎙️ Triangle Tweener Talks is (usually) hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
Who’s Advancing from the Fabulous Four - Moxie or ZW?
Welcome back to Triangle Tweener Madness, where four startups remain in the race for a $25K investment from the Triangle Tweener Fund!
In this week’s matchup, we’ve got two very different companies: one’s building AI to protect the integrity of academic research, and the other’s helping manufacturers optimize glass and ceramics production with deep tech. The stakes are higher than ever—only one will move on to the championship round.
The Contenders
🔹 Moxie (Jessica Parker) – An AI-powered research writing platform designed for PhD students, faculty, and academic researchers. Moxie helps streamline the writing and review process while preserving intellectual integrity and preventing misuse of generative AI. It’s a closed system, workflow-oriented, and focused on fluency and complexity—going far beyond what tools like Grammarly can do.
🔗 Learn more about Moxie
🔹 ZW (Robert Fu) – A precision AI platform for the materials science industry. ZW’s suite of tools helps manufacturers of glass and ceramics reduce R&D time, cut costs, and lower emissions by optimizing material formulas and manufacturing parameters. With traction in enterprise settings and deep subject-matter expertise, ZW is turning AI into ROI for an overlooked vertical.
🔗 Learn more about ZW
Key Highlights
🎤 Jessica’s Q&A (Moxie)
🎤 Robert’s Q&A (ZW)
Selection Committee Insights
💡 Mahati Sridhar saw opportunity for both platforms to scale but emphasized the importance of refining go-to-market and self-service onboarding. She noted ZW’s long-term expansion potential into other verticals.
💡 Jan Davis appreciated Moxie’s collaborative model and grassroots traction via content marketing, while noting ZW’s deeper tech and need for pricing adjustments. She voiced concern about whether ZW can scale without heavy customization.
💡 David Gardner leaned toward ZW’s B2B focus and high-value contracts, noting the risk of Moxie being overtaken by generic LLM tools if defensibility isn’t strengthened.
Who Will Move On? 🏆
After a close and thoughtful debate, the selection committee made their call. Which of these future-forward startups will compete for the $25K prize in the championship round? You’ll have to listen to find out.
Today's Selection Committee:
📌 Timestamps
🎙️ Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by:
Welcome back to Triangle Tweener Madness, where 8 startups go head-to-head for a $25K investment from the Triangle Tweener Fund!
This week, it’s a battle between a logistics platform built for scrappy e-commerce sellers and a surprising new marketing tool using your calendar.
Only one can move on to the next round. Let’s meet the contenders.
The Contenders
🔹 Deliveri (Jason Brown) – A full-service logistics tech stack for small e-commerce businesses shipping across the U.S., Canada, and Latin America. Deliveri helps brands compare rates, insure shipments, automate duties and taxes, and create branded tracking pages—all through a single platform that plugs right into Shopify and other storefronts.
🔹 InviteJet (Brian Watson and Paul Davis) – A marketing platform that lets brands send calendar invites—yes, calendar invites—to their customers as a new way to drive engagement and conversions. With integrations into tools like Klaviyo and Mailchimp, InviteJet is showing strong early traction with e-commerce brands eager for alternatives to crowded inboxes.
Key Highlights
🎤 Jason’s Pitch (Deliveri)
🎤 Brian & Paul’s Pitch (InviteJet)
Selection Committee Insights
💡 Robbie Hardy appreciated that both teams showed strong command of their business and were confident without overselling. She was intrigued by InviteJet’s novel approach and experience-driven founding story.
💡 Michael Jones noted how polished both pitches were and was impressed by the capital efficiency of both companies. He saw strong acquisition potential for both Deliveri and InviteJet.
💡 Jason Caplain pointed to the early traction InviteJet has achieved with limited resources, calling it "best of class" in terms of scrappiness and growth. He also highlighted Deliveri's strong vision and founder-market fit in the logistics space.
Who Will Move On? 🏆
After a thoughtful debate, one startup gets the nod to move forward in Tweener Madness and the chance to compete for the $25K investment. Which company did the committee choose? You’ll have to tune in to find out!
Today's Selection Committee:
📌 Timestamps
(00:00:35) – Host Scot Wingo introduces the matchup: Deliveri vs. InviteJet and welcomes the judges.
(00:01:18) – Jason Brown (Deliveri) kicks off his pitch, outlining a logistics tech platform for small e-commerce sellers.
(00:09:59) – Judges ask about scaling, competition, customer fit, and what makes Deliveri sticky as customers grow.
(00:24:12) – Brian Watson and Paul Davis (InviteJet) pitch their calendar-based marketing solution.
(00:30:53) – Judges dive into potential spam concerns, unsubscribes, and use cases beyond e-commerce.
(00:36:41) – Paul shares case studies from his own brand, Mozie Tea, showing 400%+ sales lift from calendar invites.
(00:46:51) – Judges reflect on the pitches, share feedback, and cast their votes.
(00:51:02) – Final decision and closing thoughts from the selection committee.
🎙️ Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.
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Triangle Tweener Talks is sponsored by: