Tweener Talks: Bootstrapping a Self-Publishing Book Empire: Ricci Wolman's Journey from Wall Street to Written Word Media
Ricci Wolman got the typical Wall St. job out of her MBA, but decided to follow her passion and built a platform that has helped over 45,000 indie authors achieve their entrepreneurial dreams
Who is Ricci Wolman?
Ricci Wolman didn’t set out to revolutionize indie book marketing. After moving to the U.S. from South Africa, she followed a traditional path: liberal arts college, Wall Street analyst job, and an MBA at Harvard. But the entrepreneurial spirit never left her.
In this episode of Triangle Tweener Talks, Ricci sits down with us to share how a deeply personal mission helping her mother market a self-published book sparked the idea for Written Word Media. What began as a Facebook page promoting free Kindle books evolved into a full-fledged platform used by tens of thousands of authors and millions of readers.
We dive deep into Ricci’s non-linear journey, how her early experiences in finance and retail laid the groundwork for a data-driven business, and why she chose to bootstrap instead of raise VC despite building a wildly profitable SaaS-style marketplace.
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And special thanks to our friends at Walk West for partnering with us to produce this pod!
How I met Ricci
Ricci and I first crossed paths through the Triangle startup community, but it took some time (and a break from her national park adventures) to finally get her on the podcast. I joke about needing a pith helmet to track her down, but honestly it’s a compliment. Ricci’s the kind of founder who’s always in motion: whether she’s growing her business, supporting other entrepreneurs, or exploring the next big idea (or big mountain), she brings the same energy and curiosity to everything she does.
Listen/Watch Our Interview:
This episode spans Ricci’s remarkable journey:
Immigration & Early Career: From her family's 10-year immigration process to her first culture shocks in a Connecticut winter, Ricci recounts how resilience and adaptability shaped her entrepreneurial mindset.
Wall Street & Purpose-Driven Work: Ricci details her time at Bear Stearns, witnessing 9/11 firsthand, and making a pivotal leap into the nonprofit world with Axion and a side hustle importing fair trade goods.
Retail to Startup: After earning her MBA at Harvard, she joined The Body Shop’s ecommerce team, later moving to Lulu Publishing, where she first saw the business of self-publishing up close.
The Birth of Written Word Media: What started as a side project to help her mom became Freebooksy and eventually Written Word Media. Ricci breaks down how they built a profitable platform without outside funding, using clever strategies like affiliate marketing, email personalization, and niche community-building.
Bootstrapping, Balance & Impact: Ricci shares candid insights into how she and her co-founder/husband Farrell balanced risk, family life, and building a business aligned with their values. Plus, how the company has supported over 45,000 authors—and why that impact drives her more than public recognition.
The Latest Project: Ricci’s reflections on private vs. public barometers of success, the power of books, the evolving reading landscape, and her latest side project demystifying AI: theflop.ai.
How to watch:
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