Transforming Chronic Illness Into Your Sales Superpower with Justine Beauregard

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

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Prefer to Read About the Episode:

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If you think being great at sales and living with chronic illness are mutually exclusive, Justine Beauregard is here to flip that script. A powerhouse sales strategist who’s worked with over 700 clients and helped generate millions in revenue, Justine isn’t just redefining what it means to sell—she’s rewriting how we succeed while living with chronic illness.

In this heartfelt, wisdom-packed episode of Chronic Boss Unfiltered, Justine joins host Lilly Stairs to share her journey of building a sustainable business with multiple chronic conditions, and how transparency, process, and community became the pillars of her success.

From Sales Anxiety to Secret Sauce

Justine didn’t start her business by broadcasting her chronic illnesses. Like many of us, she worried: Would people think I’m unreliable? Would they question my capacity?

But something shifted. As she started opening up to clients, they responded with empathy and connection. “The more I shared, the more people said, ‘Wow, that makes me feel seen,’” she explained.

Now, she leads with transparency by listing her chronic conditions on her site. It’s not for pity. It’s for power. “I am my brand. I never want people to think I have it all together. I want them to see the real me.”

ADHD as a Sales Superpower

Instead of fighting her ADHD, Justine built her business around it. She credits her chronic illness experience for developing system-based thinking, efficiency, and resilience.

“Having ADHD means I can hyperfocus and build frameworks. My chronic illness taught me to be accountable, to plan ahead, to create systems that never let me drop the ball. That’s how I turned a weakness into a strategic advantage.”

Feel-Good Selling: Authentic, Not Sleazy

Justine’s framework, Closed Sales on Repeat, is grounded in feel-good selling—where authenticity wins over scripts.

“Sales shouldn’t feel like becoming someone else. That sales voice? That ‘doctor’s office voice?’ We’ve all done it. But the real magic happens when you operate inside a simple framework that lets you stay yourself.”

She helps clients use their natural communication style within a proven process. Through role play, AI-driven practice, and coaching, Justine helps entrepreneurs move from anxious to empowered.

Community > Google

One of Justine’s key revelations? Community advice is better than a thousand Google searches—especially when it comes to health.

Whether it’s insomnia, chronic migraines, or the best blue-light glasses, she’s found more effective solutions through the Chronic Boss community than any doctor’s office. “93% of purchasing decisions are based on recommendations. When those come from someone who gets your condition? That’s gold.”

The Myth of Hustle

Like many of us, Justine started with hustle culture in her veins. All-nighters, weekends, burnout cycles. But it wasn’t sustainable. She eventually realized: “Why am I recreating a toxic work environment for myself? I get to decide how I run my business.”

She built in flexibility: no calls on Fridays, late-morning starts, and seasonal adjustments around her kids’ schedules. That freedom didn’t hurt her business—it helped it thrive.

Her Secret Sauce

Justine’s secret sauce lies in merging her sales skills with her chronic illness superpowers. Her process-driven brain, built from years of medical logistics and life planning, now fuels her ability to create easy-to-follow, powerful sales strategies.

“It’s not ‘I run a business despite chronic illness’ or ‘I have a chronic illness and also run a business.’ It’s both. It’s fully integrated. That’s what being a Chronic Boss means to me.”

Want to Work with Justine?

• Website & Programs: SellWithJustine.com
• Speed Networking: MonthlySpeedNetworking.com
• Podcast: Why You Hate Sales

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Ready to find your own secret sauce?
Join the Chronic Boss Mastermind and access tools, events, and a community of ambitious women blending business and chronic illness with power, grace, and realness. Visit ChronicBoss.com to learn more.