
Finding Fearless Podcast is an exploration of human-centric leadership and a celebration of ambition. Join host Madeline Reeves, CEO of Fearless Foundry, as she digs deep to learn from the lived experiences of underestimated entrepreneurs, innovators, creators, and fearless founders. Every episode presents an opportunity to learn from their successes—and struggles—while building a company on their own terms.
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Meet the host
Madeline Reeves is a coach for ambitious entrepreneurs and the Founder and CEO of Fearless Foundry. She has spent her career serving as a business development leader working for technology companies ranging from small startups to large publicly traded companies. She launched Fearless Foundry in 2018 to help innovative leaders boost their branding and internal strategies to build better businesses and work with clients they love.
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Reach out to podcast@fearlessfoundry.com and we’ll be in touch!

You Are Your Best System: Finding Freedom in Intuition and Strategy with Mary Williams
In this episode of Finding Fearless, Madeline sits down with Mary Williams, founder of Sensible Woo. Together they explore Mary's journey from corporate librarian and digital archivist to intuitive business strategist, focusing on helping entrepreneurs integrate intuition with practical business systems.
Key themes include: the evolution of online business landscapes, building systems that honor individuality, shifting away from hustle culture toward sustainable practices, and the importance of self-awareness in entrepreneurial success. Mary also introduces her Woo Crew subscription, which combines intuitive readings with strategic business guidance to help clients navigate their business challenges authentically.

Growing a Business Without Sacrificing Your Soul with Holly Howard
In this episode of Finding Fearless, Madeline sits down with Holly, founder of Ask Holly How and host of the Cultures Within Capitalism podcast. Together they explore Holly's diverse journey from professional ballet and music therapy to business consultancy, focusing on building businesses that align with personal values.
Key themes include: navigating intuition versus fear in entrepreneurial decisions, the flaws of the capitalist "hustle culture" and its impact on well-being, building values-driven businesses in a rapidly changing technological landscape, finding purpose and balance beyond work, and the challenges of entrepreneurship.
Holly also shares insights into her approach to business consultancy and emphasizes the importance of ethical practices and creating sustainable, meaningful work.

From Purity to Liberation: A Conversation with Erica Smith
In this episode of Finding Fearless, Madeline sits down with Erica Smith, sex educator and founder of Purity Culture Dropout. Together they explore Erica's journey from nonprofit sexual health work to entrepreneurship, focusing on helping individuals deconstruct harmful messages about sexuality.
Key themes include: the challenges of becoming an entrepreneur, ethical sales practices, the importance of community, and the impact of political climates on sexuality education. Erica also announces her upcoming programs and a new book aimed at addressing sexual health for those raised in purity culture.

Redefining Wealth: Inclusive Investment Strategies with Kelly Ann Winget
In this episode of Finding Fearless, Madeline delves into human-centric leadership and the spirit of ambition as she converses with Kelly Ann Winget, the founder of Alternative Wealth Partners (AWP). Kelly shares her journey of raising nearly a billion dollars in private capital, advocating for financial empowerment, and redefining wealth. The conversation spans various topics, including Kelly’s experiences in male-dominated industries, key moments of realizing her potential, and her strategies for making investing more inclusive and equitable. They also discuss the importance of understanding private equity and different pathways to generational wealth, emphasizing the vital role of purpose in driving long-term success. Additionally, the episode highlights Kelly's book, "Pitch the Bitch: Grab Your Financial Future by the Bags," and navigates the practical steps and benefits of strategic investing.

Season Wrap Up
In this special season wrap-up of the Finding Fearless podcast, host Madeline revisits the powerful conversations of the past year. She reflects on the theme of liberation in entrepreneurship, exploring how guests have turned their challenges into opportunities for personal and professional freedom. The episode highlights impactful discussions with inspiring figures like Podge Thomas, Lauren Burgess, Meredith Fennessy Witts, Brianna Franklin, and Mary Bailey, who share their unique journeys and insights on breaking free from traditional constraints. Madeline also introduces upcoming opportunities for listeners to engage with her work through the Figure 8 program and the Finding Fearless community.