Chronic Boss Unfiltered

Turning Pain Into Punchlines: Life As A Comedian With Type 1 Diabetes with Ivana Bonetti

“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:
How Ivana transformed her Type 1 diabetes diagnosis into comedic inspiration
The cultural role of food in her Italian-American upbringing—and how she navigates it with diabetes
Why support from family and community is essential for chronic illness management
How humor builds resilience and breaks down stigma
The lessons chronic illness teaches about adaptability, identity, and authenticity
Why embracing your story—messy parts and all—can empower both you and your audience
What it means to be a Chronic Boss when your life literally depends on balance
Timestamps:
(00:00) – Introduction: Meet Ivana Bonetti, comedian, storyteller, and Chronic Boss. (04:47) – Navigating Life with Type 1 Diabetes: Diagnosis, shock, and self-discovery. (10:08) – From Medicine to Microphone: The career pivot that changed everything. (14:54) – Building a Comedy Career: Finding her voice, her audience, and her punchlines. (19:54) – Living with Diabetes: Daily management and emotional resilience. (25:00) – Comedy as Advocacy: Turning medical moments into laughter and awareness. (30:11) – The Secret Sauce of a Chronic Boss: Humor, heart, and unshakable grit.
 Connect with Ivana:
 
✨Instagram
✨Tik Tok
✨Youtube
 
Connect with Chronic Boss:
🖤 chronicboss.com🖤 Instagram🖤 LinkedIn🖤 TikTok
 
Connect with Lilly:
🖤 lillystairs.com🖤 LinkedIn🖤 Instagram

Transforming Chronic Illness Into Your Sales Superpower with Justine Beauregard

“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:
Justine has worked with 700+ clients, helping them generate millions in revenue.
Vulnerability and openness about her chronic illnesses became a powerful branding asset.
ADHD reframed as a superpower: hyperfocus, efficiency, and system-building.
Sales anxiety can be reduced through frameworks that allow authenticity.
Business sustainability comes from flexibility, not rigid hustle culture.
Community recommendations are more powerful than Google searches—especially for health
Defines a Chronic Boss as someone who fully integrates ambition and chronic illness
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 
 

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
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
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 

How A Life Changing Diagnosis Sparked a Clean Beauty Empire with Indie Lee

“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.”
Episode Overview
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.
What You’ll Learn
How Indie transformed a devastating brain tumor diagnosis into her life’s mission.
The tough realities of entrepreneurship with chronic illness (including going 10 years without a salary).
Why vulnerability and storytelling are powerful leadership tools.
How to set boundaries and build support systems that protect healthy.
Why “failure” is often a catapult forward.
Timestamps
(00:00) Introduction – Lilly introduces Indie and her inspiring story.(01:22) Diagnosis Journey – Living with RA, Crohn’s, and ovarian failure.(04:16) Brain Tumor Diagnosis – A six-month prognosis reframed as a turning point.(07:26) Spark for Clean Beauty – From greenhouse calendula to skincare.(09:30) Launching Indie Lee Skincare – Funding with jewelry sales and 401k cash-outs.(11:52) Surgery on Earth Day – A life-saving moment that shaped her mission.(12:21) Leading with Vulnerability – How transparency became a brand strength.(16:09) Entrepreneurship with Chronic Illness – Travel, boundaries, and hospitalizations.(19:27) Asking for Help as a Superpower – The role of support systems.(22:20) The Hustle Culture Trap – Rejecting “do it all” culture.(26:11) Pioneering Clean Beauty – Ignorance is bliss and blocking out doubters.(28:27) Reality of Building a Business – Ten years without a salary, losing her house.
(31:41) Redefining Failure – Turning setbacks into lessons.(33:02) Secret Sauce – Blending branding, writing, and vulnerability.(35:47) Reconnecting with Self – Baking, gardening, and writing.(42:58) What Being a Chronic Boss Means – Perseverance and purpose.
 
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/ 
 

Isn't It Crazy That People Can't Say The Word Vagina? -- The Knowledge Gap In Women's Health with Priyanka Jain

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.
What You’ll Learn
Why vaginal health is central to closing the gender health gap.
How the vaginal microbiome connects to conditions like infertility and endometriosis.
What it takes to build the largest dataset in women’s health.
Why community is critical in breaking stigma and advancing research.How resilience and balance fuel Priyanka’s leadership.
Timestamps:
 (00:00) Introduction – Lilly introduces Priyanka and Evvy’s mission. (00:52) Meet Priyanka – Forbes 30 Under 30 and vaginal health pioneer. (02:00) Lilly’s Story – Recurrent UTIs and silence around vaginal health. (03:19) Breaking the Taboo – Why vaginal health remains stigmatized. (06:42) What Evvy Does – Using metagenomic sequencing for diagnostics. (09:00) The Vaginal Microbiome – Good bacteria, pH balance, and disruptions. (11:06) Priyanka’s Patient Journey – Chronic conditions and dismissal in care. (14:42) Why the Vaginal Microbiome Matters – The tipping point moment. (16:49) Largest Dataset Built – 75,000 patients, 2,000 doctors, 98% consent. (18:20) Surprising Insights – Links to infertility, endometriosis, PCOS. (23:21) Building Community – How the Facebook group empowers and fuels research. (27:58) Imposter Syndrome & Leadership – Turning doubt into a strength. (31:20) Advice for Founders – Resilience and the chronic illness edge. (34:03) Balancing Health & Entrepreneurship – Priyanka’s non-negotiables. (37:05) Solidarity & Research Day – Equal Research Day and the power of community. (39:38) Breaking Silence – Normalizing vaginal health conversations. (42:25) What Being a Chronic Boss Means – Picking yourself up again and again.
Connect with Evvy:
✨/ https://www.evvy.com/ 
✨/https://www.instagram.com/evvy  
✨/ https://www.tiktok.com/@evvybio 
✨/ 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 
Links Mentioned
/ https://www.equalresearchday.com/

The Truth About Work, Sex and Chronic Illness with Ali DiGiacomo

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.
What You’ll Learn
How Ali turned her RA diagnosis into a platform for advocacy and empowerment.
Why authenticity and humor resonate more than “perfect” highlight reels.
The realities of freelancing and health insurance with chronic illness.
Tips for traveling and working while managing RA.
Why breaking the silence around intimacy and pelvic health matters.
Timestamps
 (00:00) Introduction – Lilly welcomes Ali to the podcast. (00:46) Meet Ali – From “Another Day with RA” to trainer and advocate. (02:07) Diagnosis at 15 – Balancing RA with competitive swimming. (05:24) Losing Swimming, Finding Fitness – Rediscovering movement through inspiration online. (07:39) Becoming a Personal Trainer – The path back to fitness. (08:14) Launching “Fuck It, Let’s Slay” – Creating workouts for chronic illness. (11:35) Community Feedback – Stories of transformation from users. (12:53) Building a Social Following – Growing to 160K with raw honesty. (14:48) Authenticity & Dark Comedy – Why humor resonates online. (18:27) Setting Boundaries – Managing DMs, burnout, and online pressure. (22:47) Freelancing Realities – Wearing many hats and navigating insurance. (32:19) Nomadic Lifestyle – Living in an Airstream and traveling with RA. (38:13) Travel Hacks – Meds, injections, and business on the road. (42:14) Attitude as a Superpower – Resilience and rolling with the punches. (47:29) Getting real about sex & intimacy – Talking openly about pelvic health. (55:46) Authentic Women’s Health Conversations – Breaking taboos. (57:18) What Being a Chronic Boss Means – Ali’s empowering definition.
 
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 to Chronic Boss Unfiltered

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