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:

• Why Doug was initially hesitant to get involved with TransLoc, a company focused on "mass transit technology".
• The red flags he ignored when joining TransLoc , and how he turned the company around after discovering it was not financially healthy.
• How TransLoc expanded its services beyond tracking buses to create a "mobility network" and provide data-driven insights to transit agencies.
• The story of TransLoc's acquisition by Ford , and the delicate process of bringing a Fortune 15 M&A team back to the table after walking away.
• Dr. Kaufman’s philosophy on how to run a board, including the importance of setting clear roles and fostering a collaborative team environment.
• A candid account of his experience with his next startup, Belongly, and the painful lessons learned from market shifts and fundraising challenges.
• The psychological impact of founder ups and downs , and why Dr. Kaufman believes vulnerability is a "superpower" for entrepreneurs.

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:
(00:01:00) 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:

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

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/