In this inspiring episode of Finding Fearless, I sit down with Henna Pryor, a workplace performance expert, award-winning author, and keynote speaker whose journey from corporate conformity to entrepreneurial authenticity challenges everything we think we know about professional success. Key themes we explored: Henna's bold leap from Big Four accounting to founding her own venture Why traditional definitions of success are failing us The revolutionary power of embracing professional awkwardness ...
Jul 09, 2025•58 min•Season 6Ep. 13
In this introspective episode of Finding Fearless, Madeline Reeves and Jamie Engelhardt explore the essence of human-centric leadership and the critical alignment of mission, values, and actions in business. Madeline introduces a new segment, "Tea with the Team," featuring a candid conversation with CMO Jamie. Together, they delve into: The common inconsistencies found within "mission-driven" organizations. The challenges and vital importance of cultivating authentic brand values. The necessity ...
Jul 02, 2025•47 min•Season 6Ep. 12
In this episode of Finding Fearless, Madeline Reeves sits down with Catherine Perez and Marianna Di Regolo, the queer married founders of FAMM. Together, they explore their professional journeys and their mission to build a thriving, inclusive queer economy that challenges traditional business networks. Key themes include: The systemic barriers and funding challenges faced by LGBTQ+ professionals and entrepreneurs Their commitment to community-driven solutions and the creation of FAMM How intent...
Jun 25, 2025•1 hr 2 min•Season 6Ep. 11
In our latest episode of Finding Fearless, we had the privilege of speaking with Tricia M. Taitt, CEO of FinCore and fractional CFO who's transforming how women entrepreneurs approach their finances. Her journey from Wall Street executive to financial empowerment advocate offers powerful insights into building a sustainable, values-driven business. Key themes include: The critical importance of financial literacy for entrepreneurial success Why less than 2% of women-owned businesses reach seven ...
Jun 11, 2025•55 min•Season 6Ep. 10
In this episode of Finding Fearless, Madeline Reeves sits down with Marcia Dawood, author, TEDx Speaker, podcast host, and early-stage investor. Together they explore Marcia's mission to transform angel investing from an exclusive club into an accessible pathway for everyday people to fund innovation and create positive change. Key themes include: Marcia's journey from corporate finance to passionate advocate for investment democratization The untapped potential of platforms like Wefunder, Repub...
May 28, 2025•46 min•Season 6Ep. 9
In our latest episode of Finding Fearless, we had the privilege of speaking with Catherine Gray, general partner at Silicon Valley Women Founders Fund and CEO of She Angel Investors. Her journey from advertising executive to venture capital pioneer offers powerful insights into the transformation happening in the investment landscape. Key themes include: The unique challenges women face in securing venture capital funding. The power of storytelling in shifting investment culture towards greater ...
May 14, 2025•40 min•Season 6Ep. 8
In this episode of Finding Fearless, Madeline Reeves sits down with Amanda Ralston, a queer and neurodivergent serial entrepreneur and the visionary behind Non-Binary Solutions. Together, they explore Amanda's groundbreaking work in transforming autism care through innovative and inclusive approaches. Key themes include: Amanda's 25-year journey in applied behavior analysis and its evolution The development of her innovative clinical decision support system for autism treatment The changing land...
Apr 30, 2025•59 min•Season 6Ep. 7
In this powerful episode of Finding Fearless, Madeline Reeves sits down with Tanesha Grant, founder of Parents Supporting Parents NY and Moms United for Black Lives NYC. Together, they unpack the profound impact of community organizing, grassroots advocacy, and the fight for equity within systems that have historically marginalized Black families. Key themes include: The systemic barriers faced by marginalized families within the child welfare system. The importance of digital equity and communi...
Apr 16, 2025•52 min•Season 6Ep. 6
In this episode of Finding Fearless, Madeline Reeves sits down with Deb Boulanger, founder of Life After Corporate. Together they explore Deb's transformative journey from the corporate world to purpose-driven entrepreneurship, focusing on aligning ambition with authentic leadership. Key themes include: Unlearning corporate conditioning and trusting intuition. The concept of business as a transfer of energy. The importance of community in entrepreneurship. Values-driven business practices and et...
Apr 02, 2025•1 hr 4 min•Season 6Ep. 5
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 ...
Mar 19, 2025•1 hr 13 min•Season 6Ep. 4
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-dr...
Mar 05, 2025•1 hr 5 min•Season 6Ep. 3
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...
Feb 19, 2025•1 hr 4 min•Season 6Ep. 2
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 ...
Feb 05, 2025•58 min•Season 6Ep. 1
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 ...
Dec 21, 2024•30 min•Season 5Ep. 24
In this solo episode of 'Finding Fearless,' host Madeline shares her personal journey from a global business development leader in FinTech to founding Fearless Foundry. She delves into the creation and mission of the Figure 8 community and mastermind program, aimed at supporting ambitious, mission-driven founders. The episode outlines the structure of the Figure 8 program, its focus on branding, marketing, pricing, and more, all designed to help marginalized founders create sustainable, fulfilli...
Dec 04, 2024•41 min•Season 5Ep. 23
In this episode of Finding Fearless, Madeline discusses the importance of businesses in driving social change post-2024 election. She shares her personal journey and the role entrepreneurship plays in economic empowerment. Madeline emphasizes the significance of hiring inclusively, offering comprehensive benefits, and utilizing financial influence to support marginalized communities. The episode serves as a rallying cry for socially-driven founders to use their businesses to protect vulnerable p...
Nov 20, 2024•18 min•Season 5Ep. 22
In this episode of Finding Fearless, Madeline interviews Mary Bailey, co-founder and managing director of the Last Prisoner Project (LPP). They discuss cannabis industry opportunities alongside the persisting issue of cannabis-related incarcerations. Mary shares her journey from event production in Hawaii to becoming an advocate for cannabis justice. The episode highlights LPP's work, aiming for the release of cannabis prisoners and promoting a socially conscious industry. Mary's story includes ...
Oct 16, 2024•1 hr 3 min•Season 5Ep. 21
In this episode of Finding Fearless, Madeline connects with Martin Moll, a former corporate executive who transitioned into entrepreneurship late in life. Martin shares his journey from a top-ranking position in finance to co-founding Breakaway Advisors, highlighting the importance of authenticity, mentorship, and scaling in business. They discuss the Breakaway model, its focus on flexible and equitable work environments, and its impact on both clients and advisors. The conversation also touches...
Oct 02, 2024•53 min•Season 5Ep. 20
In this episode of Finding Fearless, Madeline talks with Aundrea, a journalist turned entrepreneur, about her journey from traditional media to creating her own storytelling agency. They discuss the challenges of working in collapsing media landscapes, the importance of media literacy, and the rise of the creator economy. Aundrea shares her experiences covering significant political events and the personal decision to pivot to a new career in storytelling and media training. The episode explores...
Sep 18, 2024•59 min•Season 5Ep. 19
In this episode of Finding Fearless, host Madeline pulls back the curtain on powerful conversations happening within her community. This special episode features a panel discussion with three industry experts – Joanna Lovering, Becky Mollenkamp, and Trystan Reese – who share their unique approaches and authentic strategies for networking. They discuss the importance of individualized networking styles, the value of social media as a networking tool, and the role of connection and support in prof...
Sep 04, 2024•46 min•Season 5Ep. 18
In this episode of Finding Fearless, Madeline interviews Briana Franklin, founder of The Prosp(a)rity Project. They discuss the systemic issues surrounding student debt, particularly for women of color, and how Bri's personal experiences inspired her to create solutions to combat predatory lending practices. Bri elaborates on her nonprofit's mission and introduces her FinTech app, Cadet Prosparette, designed to educate young people on financial literacy and debt prevention. The conversation also...
Aug 21, 2024•55 min•Season 5Ep. 17
In this episode, host Madeline engages in a deep conversation with Michelle Bomberger, founder of Equinox Business Law Group. They discuss the importance of legal strategies for protecting businesses, focusing on issues like intellectual property, compliance, and employee matters. Michelle shares her journey from Northwestern University to establishing her firm, influenced by her experience with small businesses and corporate roles. They also discuss common legal issues faced by entrepreneurs to...
Aug 07, 2024•58 min•Season 5Ep. 16
In this episode of Finding Fearless, host Madeline interviews Lauren Burgess, a serial social entrepreneur and nomad who lives and works out of a van. The conversation covers Lauren's journey from building and exiting several successful businesses to embracing a more balanced and authentic lifestyle. Lauren shares her experiences with burnout, discovering her queerness, and redefining success based on her values of health, wellness, and fun. The episode dives into her unique perspective on entre...
Jul 24, 2024•1 hr 1 min•Season 5Ep. 15
In today’s episode, Madeline sits down with Nikki Lindgren, founder and managing partner at Pennock, a beauty and lifestyle brand marketing agency. Nikki shares her journey from her rural Minnesota roots to becoming a successful agency owner in San Francisco. They discuss the importance of maintaining a human-centric and sustainable approach to business, especially in the marketing sphere. Nikki outlines her path through various corporate roles, highlighting the shift from working at mega brands...
Jul 10, 2024•51 min•Season 5Ep. 14
In this episode of Finding Fearless, Madeline talks with Natalie Roberts, certified exit planning advisor and founder of iKadre. They delve into the intricacies of mergers and acquisitions (M&A) and how women entrepreneurs can navigate this space to build their business legacies. Natalie shares her extensive background in global M&A, highlighting her work at companies like Ernst Young and HP. The conversation explores the emotional aspects of exiting a business, the importance of early e...
Jun 26, 2024•48 min•Season 5Ep. 13
In this episode, Madeline interviews Charlie Sprinkman, the founder of 'Everywhere is Queer,' a platform aimed at mapping queer-owned businesses worldwide. Charlie shares their journey from growing up in conservative Wisconsin to founding a resource that now lists over 12,000 queer-owned businesses. They discuss the inspiration behind the platform, the challenges of entrepreneurship, and the recent launch of their mobile app. The episode also delves into the importance of community support, the ...
Jun 12, 2024•46 min•Season 5Ep. 12
In this episode of Finding Fearless, Madeline talks with Dr. Dee Frayne, a life and business coach with over 20 years of experience in building and strengthening communities. They discuss the power of channeling anger to enact positive change in the world and delve into Dr. Frayne's journey of transformation from working in non-profits and higher education to coaching individuals to achieve their world-changing goals. The episode explores themes of human-centric leadership, entrepreneurship, rad...
May 29, 2024•1 hr 10 min•Season 5Ep. 11
In this episode, Madeline sits down with Kelly George, a black Latinx queer bipolar neurodivergent, founder and CEO of Real Resilience Coaching and Consulting, and a pioneering coach in neurodivergence and mental health. They discuss the importance of empowering neurodivergent leaders to create business models that align with their strengths and advocate for their needs. George shares her journey from growing up in Brooklyn with Caribbean parents, through her challenges and experiences of neurod...
May 15, 2024•1 hr 4 min•Season 5Ep. 10
This episode features a powerful, raw and authentic conversation between Madeline and multidisciplinary artist and activist Alex Jamieson, who discusses her journey of using art as a vehicle for social change, especially focusing on reproductive rights. Raised by politically active hippies, Alex's upbringing infused her with the drive to use creativity against societal and political norms. Throughout the interview, Alex shares her path from starting a zine in college to confronting crisis pregna...
May 01, 2024•1 hr 12 min•Season 5Ep. 9
In this episode Madeline talks to Meredith Fennessy Witts, founder of Le Chéile, about one of the most important and ignored topics while building businesses: Financial Fluency. They cover topics such as the accidental path to becoming an entrepreneur, the importance of community and mentorship, financial fluency for business owners, and the challenges and strategies of scaling a business. Meredith shares her personal story, including her background, how she navigated the transition from corpora...
Apr 17, 2024•1 hr 8 min•Season 5Ep. 8
