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When Wall Street Ambition Meets the Reality of Chronic Illness with Alex Wildeson
I didnt want to let me chronic illness take that away from me so during my medical leave I decided to launch three businesses
Episode Overview
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
What You’ll Learn
Timestamps
(00:00) – IntroductionLilly sets the stage: ambition, women’s health, and chronic illness.
(03:12) – Leaving Wall Street Dreams Surgeries, hospitalizations, and realizing work couldn’t be her whole identity.
(04:44) – Pivot to Pensions Rebuilding a $5B venture book at the Texas Teachers Retirement System.
(05:33) – A Botched Spinal Surgery Waking up paralyzed, hospital stay, and stepping away from traditional finance.
(07:29) – Finance Meets Creativity How storytelling and numbers-thinking became her edge.
(09:47) – The Birth of Calling In Sick A TikTok video goes viral, sparking a new platform.
(11:22) – A Safe Space, Not Trauma Dumping Building community around hope, joy, and connection.
(13:21) – Seeds of Hope Why Alex refuses to resign to “just being sick.”
(17:34) – Boundaries & Delegation Protecting energy, knowing her work hours, and building a team of chronically ill women.
(20:40) – Letting Go of Guilt Owning your time, not responding to every DM, and the $/hour mindset.
(25:25) – Redefining AmbitionFrom promotions and bonuses to impact and human connection.
(31:04) – Alex’s Secret Sauce Analytical brain + high EQ fueled by chronic illness = magic in social media growth.
(33:51) – Advice for Entrepreneurs Find environments that celebrate your superpower.
(34:37) – What’s Next for Alex Growing Calling In Sick, launching a new app, and pitching a TV show.
(39:21) – What Being a Chronic Boss Means Making little Alex proud: honoring past versions of herself and embracing the whole identity.
Connect with Alex:
✨/ https://www.instagram.com/AlexandraWilderson/
✨/ https://www.tiktok.com/@alexandrawildeson
✨/ https://www.justmediahouse.com/podcasts/calling-in-sick
✨/ https://open.spotify.com/show/1FbzAVRNAYGWW8l8IPQew5?si=64a284c358a94e75
Connect with Chronic Boss:
🖤 / https://chronicboss.com/
🖤 / instagram.com/chronicbossco/
🖤 / https://www.linkedin.com/company/chronic-boss/
🖤 / https://www.tiktok.com/@chronicbossco
Connect with Lilly:
🖤 / https://lillystairs.com/
🖤 / https://www.linkedin.com/in/lillystairs/
🖤 / https://www.instagram.com/lillystairs
View all episodes
By Lilly StairsI didnt want to let me chronic illness take that away from me so during my medical leave I decided to launch three businesses
Episode Overview
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
What You’ll Learn
Timestamps
(00:00) – IntroductionLilly sets the stage: ambition, women’s health, and chronic illness.
(03:12) – Leaving Wall Street Dreams Surgeries, hospitalizations, and realizing work couldn’t be her whole identity.
(04:44) – Pivot to Pensions Rebuilding a $5B venture book at the Texas Teachers Retirement System.
(05:33) – A Botched Spinal Surgery Waking up paralyzed, hospital stay, and stepping away from traditional finance.
(07:29) – Finance Meets Creativity How storytelling and numbers-thinking became her edge.
(09:47) – The Birth of Calling In Sick A TikTok video goes viral, sparking a new platform.
(11:22) – A Safe Space, Not Trauma Dumping Building community around hope, joy, and connection.
(13:21) – Seeds of Hope Why Alex refuses to resign to “just being sick.”
(17:34) – Boundaries & Delegation Protecting energy, knowing her work hours, and building a team of chronically ill women.
(20:40) – Letting Go of Guilt Owning your time, not responding to every DM, and the $/hour mindset.
(25:25) – Redefining AmbitionFrom promotions and bonuses to impact and human connection.
(31:04) – Alex’s Secret Sauce Analytical brain + high EQ fueled by chronic illness = magic in social media growth.
(33:51) – Advice for Entrepreneurs Find environments that celebrate your superpower.
(34:37) – What’s Next for Alex Growing Calling In Sick, launching a new app, and pitching a TV show.
(39:21) – What Being a Chronic Boss Means Making little Alex proud: honoring past versions of herself and embracing the whole identity.
Connect with Alex:
✨/ https://www.instagram.com/AlexandraWilderson/
✨/ https://www.tiktok.com/@alexandrawildeson
✨/ https://www.justmediahouse.com/podcasts/calling-in-sick
✨/ https://open.spotify.com/show/1FbzAVRNAYGWW8l8IPQew5?si=64a284c358a94e75
Connect with Chronic Boss:
🖤 / https://chronicboss.com/
🖤 / instagram.com/chronicbossco/
🖤 / https://www.linkedin.com/company/chronic-boss/
🖤 / https://www.tiktok.com/@chronicbossco
Connect with Lilly:
🖤 / https://lillystairs.com/
🖤 / https://www.linkedin.com/in/lillystairs/
🖤 / https://www.instagram.com/lillystairs