When Wall Street Ambition Meets the Reality of Chronic Illness with Alex Wildeson

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

• 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

Prefer to Read About the Episode:

Alex Wildson is a venture capitalist, storyteller, and chronic illness advocate redefining what it means to build, lead, and thrive while living with six chronic conditions. On this episode of Chronic Boss Unfiltered, she joins host Lilly Stairs to share her story of pivots, power moves, and the radical clarity that can come from slowing down.

From Investment Banking to Impact

Alex’s journey began in the grind of oil and gas investment banking. She climbed fast, thriving on 120-hour workweeks and adrenaline-fueled deadlines. But her health was deteriorating. A series of infections, hospitalizations, and diagnoses forced her to reconsider everything. When a spinal surgery in 2023 left her temporarily paralyzed, Alex used her recovery not as a pause, but a pivot. She launched three ventures: a podcast and community platform called Calling In Sick, a creative consulting firm with her sister, and a VC role with a firm investing in celebrity-founded CPG brands.

Creating Calling In Sick: A Safe Space for Sick Girls Who Dream Big

During medical leave, Alex posted a single TikTok that went viral. Suddenly, she had a platform. But she didn’t want to just talk about illness. “I don’t want to only show chronic illness. I want to show everything.”

Calling In Sick became a podcast, a community, and a movement. It’s not a place for trauma-dumping or medical advice. It’s a place for hope, connection, and identity beyond the diagnosis. As Alex puts it, “We’re the best friend group you wish you had.”

Boundaries, Delegation, and Energy Management

Entrepreneurship with chronic illness requires a different playbook. For Alex, that includes:

• Strict Time Blocking: She works when her energy peaks (10 a.m. to 3 p.m.) and unapologetically rests when needed.
• Delegation: Her team includes chronically ill women with clearly defined roles and limits. “Nobody gets overwhelmed. There’s always backup.”
• Boundary Setting: Alex no longer replies to every DM or email. “If it’s not a hell yes, it’s a no.”

Redefining Ambition and Success

After leaving her finance career, Alex struggled with whether she was still ambitious. “Did I become lazy?” she wondered. Through therapy and reflection, she realized success had to look different now. It wasn’t about titles or bonuses. It was about impact.

“When I get a message from someone saying the podcast helped their partner out of a depression spiral, that’s my success metric now. That’s what lights me up.”

The Secret Sauce: Where Finance Meets Feelings

Alex’s secret sauce is the intersection of analytical thinking and emotional intelligence. She brings her finance brain to content strategy, studying engagement trends and patterns. But it’s her empathy—shaped by personal and family illness—that gives her storytelling its punch. “I attack from both sides,” she says. “That’s where the magic happens.”

What’s Next?

From co-building a new app to exploring TV opportunities with ex-HBO creatives, Alex is thinking big. But she’s also celebrating each small win along the way. “You only get your first 1,000 likes once. I want to soak up every moment.”

What Being a Chronic Boss Means

To Alex, being a Chronic Boss is about making her younger self proud. “I was in a wheelchair in elementary school, not knowing what life would look like. Now I get to say: I’m sick and I’m all these other things.”

Follow Alex
Instagram & TikTok: @alexandrawilderson
Podcast: Calling In Sick
VC & startup work: Connect on LinkedIn

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