In this episode of Bearing It All, host Kate Ginsberg, founder and CEO of Queen of To Do, sits down with comedian and event producer Jason Dudey (@jasondudey) for a candid conversation about resilience, reinvention, and how humor helps navigate life’s biggest challenges.

Jason, a recent divorcee and cancer survivor, shares his unique perspective on life: “Life happens, and it keeps happening. And then, when you’re not looking, it happens again. I never thought cancer would be funny, but when you lose hair in places you didn’t even know you had hair, you have to laugh and move on.”

Jason’s journey is filled with humor, heart, and the wisdom gained from overcoming life’s toughest moments.

You’ll hear about:
• Laughing through life’s hardest challenges
• Using humor as a powerful tool for healing
• Reinventing yourself after loss and change
• Finding meaning and resilience through comedy

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In this solo episode of Bearing It All, host Kate Ginsberg, founder and CEO of Queen of To Do, gets radically honest about what it really means to build a business that puts people first.

From ethical hiring to setting unapologetic boundaries, Kate breaks down how values-driven leadership can shape every part of your company culture. This isn’t just a conversation about business, it’s a call to lead with empathy, integrity, and courage, even when it’s hard.

Kate shares the behind-the-scenes of Queen of To Do’s evolution from a one-woman operation to a thriving team of 19 W-2 employees, and what it took to stay aligned with her values every step of the way.

You’ll hear about:
• Building a people-first business
• Why boundaries create stronger teams
• Hiring for values, not just skills
• The impact of culture on retention
• How kindness can be operational, not optional

If you’ve ever wondered how to balance leading with heart and strategy, this episode is for you.

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What does it really take to start over after success?

In this episode of Bearing It All, host Kate Ginsberg sits down with award-winning entrepreneur Heather Emerson, founder and CEO of Offshore Launch, for a raw and empowering conversation on fear, identity, grief, and the courage to rebuild.

Heather opens up about closing a multimillion-dollar company, navigating early pregnancy, and finding purpose again through a new venture built on integrity and execution. Together, she and Kate explore how COVID reshaped entrepreneurship, why humility is an underrated strength, and how to lead with honesty, even when it costs you comfort.

You’ll hear about:
• Fear as a roadmap, not a stop sign
• Why execution matters more than ideas
• Integrity as a lasting competitive advantage
• The power of sharing knowledge instead of guarding it
• How to lead with honesty and still win

Whether you’re pivoting, rebuilding, or redefining what success looks like, this episode reminds you that starting over doesn’t mean starting from scratch.

About the Guest:
Heather Emerson is the founder and CEO of Offshore Launch, a global staffing company connecting businesses with international virtual assistants. She’s a Forbes Next 1000 honoree and was named to Austin’s Under 40 list in 2021.

Follow Bearing It All for real conversations with entrepreneurs who are building bold, meaningful businesses.
If you enjoyed this episode, don’t forget to rate and follow the show on Spotify, it really helps us grow!