Chronic Boss Scholarship Winners on Building Businesses, Managing Flares, and the Power of Community
What does it look like to build a company while your body is working against you? In this episode, host Lilly Stairs sits down with two Chronic Boss Scholarship recipients who are doing exactly that — and doing it brilliantly. Jolie Wyatt, founder of If the Shoe Fits and newly minted Babson grad, is revolutionizing the footwear industry with custom-fit heels built from 3D foot scanning technology. Amanda Berk, co-founder of Liora Health, is building a digital platform that matches women with chronic conditions to care advocates who show up with them — literally and figuratively — before, during, and after medical appointments. Both women are students, entrepreneurs, community builders, and chronic illness patients navigating it all at once.
What makes this conversation so special is how candidly Jolie and Amanda talk about the intersection of chronic illness and entrepreneurship — not as a liability, but as a lens. They cover the very real tension of scheduling your week on a Monday when your Thursday body is completely unpredictable, why stress is the common thread connecting conditions as different as hidradenitis suppurativa and chronic migraine, and how learning to block time for rest (not just work) has been a game-changer. They also share the moments that almost stopped them — including the belief that they weren't "sick enough" to deserve this scholarship — and why they applied anyway.
This episode also gets into the power of mentorship and community in a way that will light you up. Both Jolie and Amanda share the relationships that have changed everything for them — from cold DMs that turned into advisory board seats, to connections forged at the Chronic Boss launch party that are still going strong. If you've ever wondered whether putting yourself out there is worth it, this episode is your answer.
WHAT YOU'LL LEARN
* Why stress is the hidden trigger connecting wildly different chronic conditions — and what Jolie and Amanda each do to stay ahead of it
* The scheduling hack that every chronic illness entrepreneur needs (hint: it's not just blocking time for calls)
* How to think about transparency with your community, your friends, and your network when you have a chronic condition — and why sharing opens more doors than it closes
* Why cold outreach works, even when you have 250 Instagram followers — and how both guests built their advisory boards entirely through DMs
* The "not sick enough" myth that almost stopped Amanda from applying to the scholarship — and why that thinking is worth confronting head-on
* What the Chronic Boss Scholarship has meant to real recipients over four years and $36,000 in awards
* How to build a reciprocal mentorship relationship that actually fills both people's cups
TIMESTAMPS
[00:00] — Welcome & Episode Introduction Lilly sets up the episode and shares why the Chronic Boss Scholarship has been the most rewarding part of running Chronic Boss.
[01:30] — Introducing Jolie Wyatt and Amanda Berk Quick intros on both guests: Jolie's custom-fit heels company If the Shoe Fits and Amanda's patient advocacy platform Liora Health.
[02:01] — Jolie's Chronic Boss Elevator Pitch Jolie introduces herself, describes the technology behind If the Shoe Fits, and shares her diagnosis of hidradenitis suppurativa at age nine.
[02:54] — Amanda's Chronic Boss Elevator Pitch Amanda walks through her journey from Hashimoto's to chronic migraine, from healthcare communications to grad school, and how it all led to co-founding Liora Health.
[04:24] — Managing Chronic Conditions While Building a Business Both guests get honest about day-to-day impact — flare cycles, mental health as a chronic condition, and the emotional weight of being a "doer" whose body doesn't always cooperate.
[06:26] — Why Mental Health Belongs Under the Chronic Illness Umbrella Lilly makes the case for reframing mental health conditions as chronic conditions — and why that framing gives them the visibility and depth they deserve.
[10:01] — The Monday/Thursday Problem Every Chronic Entrepreneur Knows Jolie names something so many founders feel but rarely say out loud: how you feel and what you can do on Monday is not the same as Thursday, and there's no way to calculate that.
[11:20] — Practical Hacks for Juggling Entrepreneurship, School & Chronic Illness Time blocking for breaks (not just tasks), listening to your body before a flare hits, and why rest is a business strategy — not a weakness.
[13:51] — The Power of Community and Radical Transparency Amanda and Jolie on being open about their conditions — with friends, founders, and followers — and how that honesty unlocks connection rather than closing doors.
[16:55] — Jolie's Origin Story: How If the Shoe Fits Was Born From a business dress day in high school to a prototype she built by hand in Johannesburg — the full arc of four years, multiple pivots, and a manufacturer in New York City.
[25:15] — Amanda's Origin Story: How Liora Health Came to Be The four-month migraine flare that changed everything, the realization that women with chronic conditions shouldn't have to navigate the healthcare system alone, and the case for patient advocacy as a sustainable business model.
[31:36] — The Role of Mentorship: Jolie & Emily Levy How a cold LinkedIn message before the Chronic Boss launch party turned into one of Jolie's most important mentorship relationships — and the "sit under a tree" advice that still resonates.
[38:57] — The Role of Mentorship: Amanda & Alex Wilderson How Amanda cold-DM'd a podcast host she admired, and how that casual FaceTime turned into an advisory board seat, a South by Southwest partnership, and a friendship.
[44:05] — The Chronic Boss Scholarship: What It Meant to Each of Them Both guests share how they found the scholarship, the self-doubt that almost kept them from applying, and what it meant to finally feel seen.
[52:25] — What Does Being a Chronic Boss Mean to You? Closing reflections from both guests on wearing your chronic illness on your sleeve, the superpowers it gives you, and what it means to live fully — not just between flares.
Connect with Jolie & If the Shoe Fits:
🖤 / instagram.com/iftheshoefits.co [https://instagram.com/iftheshoefits.co]
🖤 / linkedin.com/in/joliewyatt [https://www.linkedin.com/in/joliewyatt]
🖤 / iftheshoefits.co [https://iftheshoefits.co]
Connect with Amanda & Liora Health:
🖤 / instagram.com/liorahealthadvocates [https://www.instagram.com/liorahealthadvocates/]
🖤 / liorahealth.io [http://liorahealth.io/]
🖤 / linkedin.com/in/amanda-berk [http://linkedin.com/in/amanda-berk]
Connect with Chronic Boss:
🖤 / https://chronicboss.com/ [https://chronicboss.com/]
🖤 / instagram.com/chronicbossco/ [http://instagram.com/chronicbossco/]
🖤 / https://www.linkedin.com/company/chronic-boss/ [https://www.linkedin.com/company/chronic-boss-collective/]
🖤 / https://www.tiktok.com/@chronicbossco [https://www.tiktok.com/@chronicbossco?lang=en]
Connect with Lilly:
🖤 / https://lillystairs.com/ [https://lillystairs.com/]
🖤 / https://www.linkedin.com/in/lillystairs/ [https://www.linkedin.com/in/lillystairs/]
🖤 / https://www.instagram.com/lillystairs [https://www.instagram.com/lillystairs]
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