Written Word Media's Ricci Wolman on Immigrating to the US, Entrepreneurial Freedom, and the Paradox of Choice

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/