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/