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:

• Why Doug left the academic track to start his own online education company and a side hustle to fund it.
• His experience in the early days of a hyper-growth startup at Blackboard, and why he eventually left to seek new challenges.
• The story of his move to the Triangle and the founding of his first company, ClearTXT, a one-to-many notification system for universities.
• The unexpected challenges he faced at ClearTXT, including a televised public relations crisis and a patent troll lawsuit.
• Why his bootstrapped company consistently beat a larger, VC-funded competitor in a head-to-head competition.
• The origin of Spring Metrics and his early lessons from joining the Triangle Startup Factory.
• A candid account of his first, disastrous board meeting, and the onset of "founder burnout" that led to a painful but necessary exit.

Where to Find Dr. Doug Kaufman:

LinkedIn: https://www.linkedin.com/in/drdougkaufman/

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:
(00:02:00) 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:

• Atomic Object: https://atomicobject.com/

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:

• Ricci's immigration story from South Africa to the US and the culture shocks she faced along the way.
• Why she left a lucrative Wall Street job after 9/11 to pursue a more impactful career in microfinance.
• How her experiences at The Body Shop and Lulu Publishing laid the groundwork for her own entrepreneurial venture.
• The origin story of Written Word Media, which was inspired by her mom's self-published book and a realization about the "paradox of choice" on Amazon.
• Why the generous Amazon affiliate program in its early days acted as an unintentional seed fund for the business.
• The unique two-sided marketplace model that matches authors with hyper-personalized email newsletters for readers.
• Ricci's philosophy on "private barometers of success" and why bootstrapping allowed her to build a business aligned with her core values.
• Her passion project, The Flop.ai, a newsletter dedicated to demystifying AI and helping people overcome their fear of new technology.
• Her advice for young founders, including why it's okay to take risks and the value of a strong local community.

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:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

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:

• Atomic Object: https://atomicobject.com/

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:

• Jason's unexpected journey from Mebane, NC, to Wall Street, Silicon Valley, and back again, shaped by a series of "learning experiences."
• The wild story of his early angel investment in Tap Tap Revenge, a mobile game that became an App Store sensation.
• How the "dirty data plumbing" challenge in manufacturing led Ndustrial to pivot from a service business to a SaaS platform for industrial energy management.
• The critical insight that led to Ndustrial's first major product breakthrough: predicting and managing Coincident Peak energy charges for factories.
• Why Ndustrial embraces a hybrid model of SaaS and professional services, contrasting with traditional Silicon Valley expectations.
• His strategic approach to bringing in corporate venture capital from global giants like ABB and GS Energy.
• Jason's vision for Ndustrial, balancing profitability with environmental impact, and why they aim to build a "sustainable business" rather than chasing a quick exit.
• The company's significant work in the cold chain industry, including efforts to optimize food refrigeration and reduce energy consumption.
• The vital role of AI in industrial settings, particularly for contextualizing data and speeding up analysis, even amidst "dirty data."
• Jason's perspective on the Triangle's clean tech ecosystem and the responsibility entrepreneurs have to support each other by buying from local startups.

Where to Find Jason Massey:

LinkedIn: https://www.linkedin.com/in/jasonmnc/
Ndustrial: https://ndustrial.io/

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) 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:

• Atomic Object: https://atomicobject.com/

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:

• What a venture studio is and how Eric's 24 and Up model co-creates companies with entrepreneurs, acting as an "unpaid co-founder."
• How the venture studio model provides hands-on support, helping companies grow faster and achieve better outcomes.
• The origin stories of Revcast (revenue optimization), Wayfound (AI agent performance management), Troop (brand story consistency with AI), and Sesame (digital identity marketplace), including which ideas came from within the studio and which were external.
• The challenges and opportunities of building companies in a changing macroeconomic landscape.
• Eric's perspective on managing multiple companies simultaneously and the team structure at 24 and Up.
• A candid discussion on the Triangle's startup ecosystem, including its strengths in technical talent and successful founders, and areas needing development like early-stage venture capital.
• Why entrepreneurs have a responsibility to buy from other startups to strengthen the local ecosystem.

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:

• Atomic Object: https://atomicobject.com/

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:

• Eric's early fascination with computers and how he balanced academics with sports from a young age.
• The story of his first startup with Todd Olson (Pendo CEO) and the valuable, albeit tough, lessons learned during the dot-com crash.
• How Eric transitioned into marketing and product roles at larger companies, gaining international experience and an understanding of public company dynamics.
• The origins of Pendo, from its unique name and iconic pink branding to its groundbreaking approach to product experience and company culture.
• Eric's perspective on the "golden era of product management" driven by AI and why understanding user problems is more critical than ever.
• The personal decision behind stepping away from Pendo to pursue his long-held ambition of running a venture studio.

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:

• Atomic Object: https://atomicobject.com/

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:

• How Jason’s early entrepreneurial experiences shaped his work ethic and future ventures.
• The story behind Raleigh Founded and its pivotal role in connecting Triangle entrepreneurs.
• Why Jason saw a need for Blue Co. – a flexible warehousing solution – and how it supports small businesses like plumbers, electricians, and moving companies.
• The lessons Jason learned from building and scaling businesses in hospitality, real estate, and co-working.
• Jason’s future vision for Blue Co. and his strategy for expanding across the Southeast.

Where to Find Jason Widen:

• LinkedIn: https://www.linkedin.com/in/jasonwiden
• Blue Co.: https://www.bluecowarehousing.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:
(00:03:00) 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.

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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:

• Atomic Object: https://atomicobject.com/

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:

• Chris’s early fascination with maps and how it led him to become a leader in the tech space.
• The inside story of MapQuest and its revolutionary role in the rise of online mapping, years before Google Maps.
• The entrepreneurial lessons Chris learned while transitioning from MapQuest to venture capital.
• Insights from running one of the first accelerators in the Triangle and how it shaped the region’s startup ecosystem.
• Stories of standout companies from the Triangle Startup Factory, including the success of Archive Social.

Where to Find Chris Heivly:

• LinkedIn: https://www.linkedin.com/in/chrisheivly/
• Build the Fort Blog: https://heivly.com/blog/

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:
(00:03:00) 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:

• Going Against the Flow: Chris Heivly, Managing Director of The Startup Factory: https://www.huffpost.com/entry/going-against-the-flow-ch_b_10596620
• One-on-one: ‘Startup Whisperer’ Chris Heivly talks Raleigh-Durham Startup Week, Triangle’s success, new book: https://wraltechwire.com/2023/04/19/one-on-one-startup-whisperer-chris-heivly-talks-raleigh-durham-startup-week-triangles-success-new-book/

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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:

• Atomic Object: https://atomicobject.com/

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:

• Hersh’s path to founding Allstacks and his early struggles with raising capital.
• The challenge of measuring engineering productivity and how Allstacks solves it with data.
• Insights on making the leap from consulting to product development and what tech companies need to understand about the market.
• The future of engineering productivity—how AI is playing a role in tracking performance.
• Lessons learned from building a dev-tech startup in a competitive space.

Where to Find Hersh Tapadia:

• LinkedIn: https://www.linkedin.com/in/hershtapadia
• Allstacks: https://www.allstacks.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:
(00:03:00) 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:

• Allstacks raises $20M to help engineering teams measure productivity: https://techcrunch.com/2024/03/30/allstacks-raises-20m-productivity/
• How Allstacks is changing the way engineering teams measure success: https://www.forbes.com/sites/hersh-tapadia-allstacks/
• The Importance of Data-Driven Engineering Teams in 2025: https://www.businessinsider.com/data-driven-engg-productivity-allstacks

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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:

• Atomic Object: https://atomicobject.com/