When we talk about leadership, disruption, and creating impact, few people embody those qualities as powerfully as Anne Kennedy. As the Co-Managing Director of Masters Fund, Anne is not only a trailblazer in the digital marketing and SEO space, but also a fierce advocate for women entrepreneurs who continue to face uphill battles in funding and investment. Her story is one of resilience, transformation, and unwavering commitment to paying it forward — and that’s why I was honored to feature her on C-Suite Success.
Anne’s journey began in the early days of digital marketing, well before Google became a household name. She co-founded Beyond, Inc. in 1997, building one of the first digital marketing agencies that helped power the online launches of household names like Zillow, Jib-Jab, and Avvo. From working with startups to securing massive contracts with industry giants like Hearst, Anne experienced both exhilarating highs and gut-wrenching lows.
One of those lows came during the 2008 financial crisis, when the economic downturn forced her to make the painful decision of closing offices and letting go of her team. That moment left an indelible mark, teaching her a powerful truth: business success isn’t just about growth, it’s about resilience—and resilience requires funding.
Anne’s uncle, a longtime newspaperman, once shared advice that has stayed with her: “Always allocate a third for your current business, a third for profits, and a third for the future.” Like so many fast-growing entrepreneurs, she admits she didn’t follow that wisdom closely enough, and the financial crash exposed the danger of being under-capitalized. That hard-learned lesson is now a driving force behind her mission: making sure women entrepreneurs have the financial resources they need to weather storms and seize opportunities.
The numbers paint a stark reality. In 2023, QuickBooks reported that more than half of women-owned businesses are still financed primarily through personal savings. While women-owned businesses received 28.4% of SBA 7a and 504 loan dollars, they continue to receive less than 2 percent of venture capital allocation. Even more disheartening, the percentage decreased from 2022 to 2023. And yet, decades of research prove that women-led businesses consistently outperform their male-led counterparts in profitability, market share and overall shareholder returns — delivering 35 percent higher returns at exit.
Of the S&P 500 companies, 94 percent of them (468) have male CEOs, and only 32 female CEOs. However, those female-led companies have significantly outperformed the rest with a 384 percent difference in returns versus 261 percent from male-led companies, according to the National Girls Collaborative Project.
It doesn’t make sense, and Anne is determined to change it.
At Masters Fund, Anne and her co-founder, Gillian Muessig, have built something radically different. Instead of following the traditional high-risk, high-failure venture capital model, they developed a revenue-based funding model that aligns incentives and lowers risk. Their portfolio companies — each led by women CEOs — commit to paying back investments over time from revenue, rather than relying solely on uncertain future exits. This model not only supports entrepreneurs but also provides investors with predictable, sustainable returns.
That’s real disruption.
Anne calls attention to the systemic bias in traditional venture funding, where the overwhelming majority of dollars still go to founders who fit a narrow mold: tall, white, Ivy League-educated men. “Money to go into different hands must come from different hands,” she says. That’s why she and her team are intent on broadening the net by not just taking a slice of the existing pie but doubling its size.
And the best part? Investors are starting to pay attention. Anne points out that many of her investors are women, but increasingly, men are stepping up too, especially those who want to create a better world for their daughters. They see the numbers, they see the opportunity, and they see the injustice.
What strikes me most about Anne’s story is how she threads together resilience and disruption with a genuine passion for impact. She didn’t just pivot after hardship; she built a whole new model to help others thrive. Her belief in women founders isn’t based on charity, it’s based on smart business. Supporting women-led ventures creates stronger companies, stronger economies, and stronger communities.
As we wrapped up our conversation, I asked Anne what she’s most excited about today. Her answer was immediate: the possibilities of artificial intelligence. She compared the rise of AI to the early days of the World Wide Web—another seismic shift that will reshape the way we do business. Just as the web democratized access to information, she believes AI will create new opportunities that we can’t yet fully imagine.
That sense of curiosity, continuous learning, and forward vision is exactly what defines true leadership.
Anne Kennedy is a disruptor in the best sense of the word and does so by challenging outdated models, creating smarter pathways, and championing those who have been overlooked for too long. Her story is a call to action for all of us: to invest wisely, to lead with courage, and to ensure that the next generation of women entrepreneurs has the resources they deserve.
Because at the end of the day, success isn’t just about breaking the glass ceiling—it’s about building a stronger foundation for everyone to rise.
Listen to more incredible gems from Anne by downloading the podcast on C-Suite Radio or watching the entire interview on C-Suite TV.
