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:

• Greg's entrepreneurial journey, from his computer science degree at North Carolina A&T to his early career at IBM and his ventures in everything from the bar industry to e-commerce.
• How his marketing agency, Walk West, is growing 30-40% year over year by helping clients adapt to a world where AI has disrupted traditional go-to-market strategies.
• His "Four P" framework for growth: Podcasts, Partnerships, Paid Media, and Public Relations, and why being "seen, heard, and cited" is critical for success in the age of AI.
• The concept of "personality-led growth" and why building trust and a personal brand is essential when abstract brands and ideas are losing their hold.
• Greg’s love for sneakers and what he collects.
• A fascinating conversation about Michael Jordan's business acumen, his brand effect, and his successful ownership of the Charlotte Hornets.
• The "Blockbuster moment" for Google and why they had no choice but to embrace AI.

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:

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

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/