A business podcast where ideas become opportunities
Deal Flow Diaries podcast explores the minds of visionary founders, fund managers, and cultural leaders, revealing how bold ideas become real success stories.
Mission
Deal Flow Diaries is a high-impact business podcast, offering listeners a rare window into the minds of the titans shaping today’s economy.
From private equity and real estate to fashion, tech and entertainment, Alexandra Fairweather and Elaine Chamberlain sit down with visionary founders, fund managers and cultural leaders.
Together, they reveal the untold stories behind big deals, hard setbacks and bold bets, giving listeners unfiltered lessons in risk, ambition and strategy.
Hosts
Two founders. One shared mission to rethink how business is told.
By connecting investing, innovation and cultural impact, they show how bold ideas and real leadership can transform industries and empower the next generation of entrepreneurs.
Alexandra Fairweather
Since 2017, Alexandra Fairweather has served as Director of the John Chamberlain Estate, where she preserves and advances the late artist’s legacy through visionary stewardship and strategic growth.
She has built a multidisciplinary team overseeing all aspects of the estate—from conservation and digitization to operations, finance, and property management—transforming it into a dynamic and sustainable force within the art world.
As Chamberlain’s stepdaughter, Fairweather brings a uniquely personal insight into his inventive, fearless spirit, curating projects that honor his legacy through exhibitions, partnerships, and digital storytelling.
Under her leadership, the estate has expanded its archival initiatives and forged collaborations with major institutions to present Chamberlain’s work to new global audiences.
A graduate of Columbia University, Fairweather divides her time between Shelter Island and New York City and serves on the boards of leading arts and educational organizations.
Elaine Chamberlain
Elaine Chamberlain is the founder and CEO of Láyn, a purpose-driven fashion house using elevated streetwear and community initiatives to raise awareness for mental health.
She also founded the Stay in Your Láyn Foundation, a 501(c)(3) nonprofit that provides grants and scholarships to expand access to mental health resources.
A graduate of Georgetown University Law Center, where she focused on international legal rights and served as a journal editor, Elaine previously lived in Thailand advocating for hill tribes on human rights issues.
After earning her J.D., she joined The Yucaipa Companies under investor Ron Burkle, gaining deep expertise in investments, strategy, and business development.
Through her entrepreneurial and philanthropic work, Elaine champions creativity, authenticity, and community as forces to break stigma and empower others to live fully and fearlessly.
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Learn how real deals happen, from bold risks to breakthrough results.