Chronic Boss Unfiltered

This solo episode digs into the transformative power of giving—especially for women navigating career growth, advocacy, and the realities of living with autoimmune conditions. Through personal stories and lived experience, the conversation explores how authentic, aligned giving can open doors, build community, and spark meaningful change. It also highlights the importance of protecting mental health and honoring boundaries, reminding listeners that giving is most impactful when it comes from abundance rather than obligation. By weaving together advocacy, business strategy, and self-care, the episode encourages women to lead with their values, share their stories, and use generosity as a catalyst for both personal and professional growth.

Themes:

Giving can be a powerful force for opportunity and change.

Authentic generosity thrives when it comes from abundance, not pressure.

Advocacy often begins with personal lived experience and expands into broader impact.

Community building is a cornerstone of meaningful, sustainable advocacy.

Showing up authentically can accelerate career growth and deepen connection.

Clear boundaries protect mental health and prevent burnout.

Empathy and intuition are powerful assets in business and leadership.

Self-care is part of the giving equation—pouring into yourself matters.

Infusing generosity into business strategy can drive deeper success and alignment.

00:00 — The Power of Giving

02:05 — Balancing Giving and Self-Care

05:44 — Reflection and Integration of Giving

Connect with Chronic Boss:

🖤 chronicboss.com

Connect with Lilly:

🖤 lillystairs.com

In this conversation of the Chronic Boss Unfiltered Podcast Tiffany Yu shares her inspiring journey as the founder of Diversability, a disability-owned community business. She discusses her personal experiences with disability, the evolution of her identity, and the importance of community in fostering disability pride. Tiffany reflects on the key moments that shaped Diversability from a student club into a global organization, and she highlights the impact of her TikTok series and the Anti-Ablism Manifesto in advocating for disability rights and inclusion. In this conversation, Tiffany Yu shares her journey of navigating life with a disability, her advocacy work, and the creation of her book, 'The Anti-Ablest Manifesto.' She discusses the importance of community, the impact of her content on the disability community, and her aspirations for the future. Tiffany emphasizes the need for action-oriented advocacy and the significance of finding magic in one's identity, while also addressing the challenges faced by individuals with disabilities. What You’ll Learn: The importance of community in embracing one's identity.

The proverb 'the nail that sticks out gets hammered down' shaped her understanding of identity. Diversability started as a student club and evolved into a global organization. Key inflection points for Diversability included community events and leadership transitions. The pandemic prompted a shift to virtual events for Diversability. Tiffany's TikTok series on disability has gained significant traction and views. Content creation has connected Tiffany with others in the disability community. The Anti-Ablest Manifesto aims to empower individuals and organizations. Community is essential for personal growth and acceptance. Grief and gratitude can coexist in the journey of self-acceptance. Tiffany's book serves as a legacy for disability advocacy. The importance of action-oriented advocacy in creating change. Rediscovering joy and playfulness is vital for well-being. Finding their unique voice and community. Success is defined by self-acceptance and integrity.

Timestamps:

00:00 Introduction to Tiffany Yu and Diversability

03:15 Tiffany's Personal Journey and Identity

10:31 The Evolution of Diversability

22:55 The Anti-Ablism Manifesto and TikTok Success

24:57 Navigating Life with a Disability

25:53 Creating Content for the Disability Community

28:12 The Journey to Writing a Book

30:34 The Anti-Ablest Manifesto: Purpose and Impact

35:45 Finding Magic in Disability

41:16 Legacy and Future Aspirations

Connect with Tiffany Yu:

✨Website: https://www.tiffanyyu.com/bio

✨ YouTube Channel: https://www.youtube.com/@imtiffanyyu

✨Facebook: https://www.facebook.com/imtiffanyyu

✨Instagram: https://www.instagram.com/imtiffanyyu

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

In this insightful and empowering episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with Dr. Kara Wada — quadruple board-certified physician, autoimmune warrior, and founder of the Immune Confident Institute. As both doctor and patient, Kara bridges two worlds with empathy, expertise, and authenticity.

Diagnosed with Sjogren’s syndrome after years of symptoms and normal lab results, Kara experienced firsthand how challenging it can be to navigate chronic illness — even as a medical professional. What began as a personal health struggle has evolved into her mission to transform the patient experience and redefine what it means to thrive with autoimmunity.

Together, Lilly and Kara unpack the intersection of medicine, mindset, and self-advocacy. They discuss Kara’s Four Rs framework for healing, the “Perfect Storm” concept behind autoimmune disease, and how Kara built a values-driven medical practice rooted in compassion and connection. This episode is a masterclass in resilience, authenticity, and reclaiming your health on your own terms.

 What You’ll Learn:

(00:00) – Introduction

Connect with Dr. Kara Wada:

✨Website: https://www.drkarawada.com/

✨ YouTube Channel: https://www.youtube.com/@drkarawada

✨LinkedIn: https://www.linkedin.com/in/karawadamd/

✨Instagram: https://www.instagram.com/drkarawada/

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

“I make fun of it on stage. I call it the “Betes”. The pump doesn’t wear me—I wear the pump.”

In this hilarious and heartfelt episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with Ivana Bonetti, Italian-American stand-up comedian, storyteller, and proud Type 1 diabetic. A Boston native from the North End, Ivana brings her sharp wit and resilience to the stage—transforming her chronic illness into comedy gold.

Diagnosed with Type 1 diabetes at 17, Ivana’s world shifted overnight. What began as a medical challenge became the foundation for her humor, advocacy, and perspective on life. From growing up in a food-loving Italian family to performing at legendary venues like the Laugh Factory and Apollo Theater, Ivana shares how she’s turned her “sweet” condition into a superpower.

Together, Lilly and Ivana dive into the healing power of laughter, the importance of representation in chronic illness spaces, and how comedy can bridge the gap between vulnerability and empowerment. This episode is a beautiful mix of humor, heart, and hard-earned wisdom—proof that even life’s toughest moments can be punchlines in disguise.

 What You’ll Learn:

Timestamps:

(00:00) – Introduction: Meet Ivana Bonetti, comedian, storyteller, and Chronic Boss.

 Connect with Ivana:

✨Instagram

✨Tik Tok

✨Youtube

Connect with Chronic Boss:

🖤 chronicboss.com

Connect with Lilly:

🖤 lillystairs.com

“When people meet me they always go you are so organized, you are like systems oriented, youve got frameworks for everything and im like  Ive literally trained myself to have these skills because of my chronic illness”

In this inspiring episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with Justine Beauregard, powerhouse sales strategist, entrepreneur, and Chronic Boss Collective member. Justine has helped hundreds of clients generate millions in revenue through her innovative approach to “feel-good sales.” But what makes her work extraordinary is how she’s woven her experience with multiple chronic illnesses into her sales philosophy.

Together, Lilly and Justine unpack what it means to lead with authenticity, why chronic illness can be a secret advantage in business, and how entrepreneurs can embrace frameworks that reduce sales anxiety. Justine shares her own journey of embracing vulnerability, building sustainable systems in business, creating boundaries, and cultivating a supportive community that empowers rather than drains. This conversation is equal parts strategy, wisdom, and soul

.What You’ll Learn:

Timestamps:

(00:00) – Introduction ambition meets chronic illness in the world of entrepreneurship.

(02:19) – Chronic Illness as a Mirror of Entrepreneurship  How flare-ups and uncertainty prepared her for the highs and lows of business.

(03:14) – Leading with Vulnerability Why Justine decided to openly share her conditions on her website and the impact on her clients.

(06:49) – Relating Through Authenticity  Opening up as a business strategy that deepens client trust and relatability.

(07:41) – Reframing ADHD & Other Conditions Turning hyperfocus and efficiency into strengths.

(10:07) – Confidence as an Output How confidence is built through action, not a prerequisite.

(13:37) – Process as a Superpower How medical routines taught Justine the power of systems and accountability.

(16:56) – Feel-Good Selling Defined Frameworks that empower entrepreneurs to sell authentically without anxiety.

(23:31) – Building a Business that Supports Health Sustainability, systems, and learning through trial and error.

(27:31) – Community as Medicine Why Chronic Boss connections provide both health and career solutions.

(37:25) – Finding Your Inner Circle The power of supportive, challenging, and uplifting friendships.

(43:40) – Having the Hard Conversations Growth through discomfort, curiosity, and open dialogue.

(46:16) – The Magic of Chronic Boss Networking Leading with vulnerability to create instant connection.

(51:59) – What Being a Chronic Boss Meansm Embracing all of yourself—conditions and business—as one whole identity.

Connect with Justine: 

✨/ SellWithJustine.com

✨/MonthlySpeedNetworking.com

✨/ https://www.instagram.com/sellwithjustine/#

✨/ https://www.linkedin.com/in/sellwithjustine

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 

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

(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 

“I was told I had six months to live after being diagnosed with a brain tumor. Instead, that day became the beginning of my life’s purpose.”

Indie Lee shares her extraordinary journey from multiple chronic illness diagnoses—including rheumatoid arthritis, Crohn’s, and a brain tumor—to founding one of the pioneering clean beauty brands. She opens up about entrepreneurship with illness, setting boundaries, losing everything while building her business, and how vulnerability became her greatest strength.

(00:00) Introduction – Lilly introduces Indie and her inspiring story.

(31:41) Redefining Failure – Turning setbacks into lessons.

Connect with Indie: 

✨/ https://indielee.com/ 

✨/ https://www.instagram.com/indielee/ 

✨/ https://www.instagram.com/indie_lee 

✨/ https://indielee.substack.com/ 

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 

Show Mentions

✨ / Relaxed Woman Book: https://www.amazon.com/Relaxed-Woman-Reclaim-Empowered-Joy-Filled/dp/0593719301

✨ / Michelle Irving and the Chronic Economy: https://www.linkedin.com/feed/update/urn:li:activity:7370584158756302848/ 

30% of women are experiencing a vaginal infection at any given time—yet most are more likely to be misdiagnosed than correctly diagnosed. Priyanka Jain is on a mission to change that.

Episode Overview

Evvy co-founder & CEO Priyanka Jain shares her personal journey with chronic conditions and why she’s determined to close the gender health gap. She explains how Evvy is building the largest dataset on the vaginal microbiome, the surprising links to conditions like infertility and PCOS, and the vital role of community in breaking stigma.

 (00:00) Introduction – Lilly introduces Priyanka and Evvy’s mission.

Connect with Evvy:

Connect with Chronic Boss:

Connect with Lilly:

Links Mentioned

/ https://www.equalresearchday.com/

Diagnosed with rheumatoid arthritis at 15, Ali thought her athletic career was over. Instead, she built a global following by embracing authenticity, humor, and resilience.

Episode Overview

Ali DiGiacomo—known as Another Day with RA—shares how she went from teenage athlete to patient advocate, trainer, and creator of the “Fuck It, Let’s Slay” fitness app. She opens up about building a 160K+ social following, freelancing struggles, intimacy and pelvic health, and why humor and resilience are her superpowers.

 (00:00) Introduction – Lilly welcomes Ali to the podcast.

Connect with Ali: 

✨/ https://www.instagram.com/anotherdaywithra/ 

✨/ https://www.tiktok.com/@anotherdaywithra 

✨/  https://www.anotherdaywithra.com/  

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 

Links

Ali’s Fitness App: https://my.playbookapp.io/ali-digiacomo 

Welcome! Chronic Boss Unfiltered is the podcast where ambition meets women’s health. Hosted by Lilly Stairs—two-time founder and three-time autoimmune patient—this show dives deep into what it really takes to build a business or climb the career ladder while living with chronic illness. Each week, Lilly sits down with powerhouse women who are chasing big dreams while navigating flare-ups, fatigue, and everything in between. Expect raw, unfiltered conversations that move from the hospital bed to the boardroom, giving you both inspiration and practical insights to balance health and ambition.

Connect with Chronic Boss:

🖤  / https://chronicboss.com/ 

🖤  / instagram.com/chronicbossco/ 

🖤  / https://www.linkedin.com/company/chronic-boss-collective/ 

Connect with Lilly:

🖤  / https://lillystairs.com/ 

🖤  / https://www.linkedin.com/in/lillystairs/ 

🖤  / https://www.instagram.com/lillystairs