Startup Life, Crisis, and Chaos: Psychologist Turned Serial Entrepreneur Dr. Doug Kaufman (part 1)

Triangle Tweener Talks

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/