In this candid and energizing episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with Alex Wildson-venture capitalist, entrepreneur, podcaster, and fierce chronic illness advocate.
Alex’s story is one of resilience and reinvention. From her early days in oil and gas investment banking to private equity, to becoming a VC partner and launching her own ventures, Alex has navigated a demanding career while living with multiple chronic illnesses and undergoing major surgeries. Today, she’s the founder of Calling In Sick, a fast-growing podcast and platform redefining what it means to live and lead with chronic illness.
Lilly and Alex dive deep into the power of pivoting, creating community, redefining ambition, and building sustainable systems with boundaries and delegation. Alex also shares advice on starting a podcast, using technology to overcome limitations, and why success should be measured in more than just revenue
How Alex went from investment banking grind to leading in venture capital and creative ventures.
Surviving a botched spinal surgery and used recovery time to launch three businesses.
Built Calling In Sick, a safe space for chronic illness community with hope and connection.
Advocates for boundaries, time blocking, and delegation to sustain entrepreneurship.
Redefined success away from revenue toward impact and meaningful connections.
Secret Sauce: pairing an analytical finance brain with high EQ storytelling
