Today we talk to Greg Boyd — a father of three, a widower, a husband, and now an entrepreneur on a mission to help others live more intentional lives.

Greg shares the deeply personal story of losing his wife, Alison, to brain cancer in 2020. And yes, it’s a heartbreaking story.  And yet, this isn’t a sad conversation - we laughed more than we cried.  Greg talks about the storybook life he had before all this happened, and how he’s used his trauma to be a better dad, husband, friend - shit, just a better person.  And he’s channelling his experience to start a new company with his wife, Whitney, to help people get off autopilot and live the life they’ve always wanted.

This is a conversation you will never forget.  Whether you’ve had bad things happen to you, or maybe you haven’t yet - one thing is certain.  They’re coming. And that’s not a dire view of the world.  It’s life, and nobody gets through it unscathed.  When the unexpected happens, you’re going to wake up.  You’re going to realize how short life is.  You’re going to want to make some changes to live the life you've always wanted.  So the question is, why wait?

Or better yet, as Greg says, “What the fuck are you waiting for?”

Please enjoy, Greg Boyd.

Key Takeaways:

• From Autopilot to Awareness: Before Alison’s diagnosis, Greg was living the “perfect life” on paper — successful job, beautiful family, dream house — but he felt oddly disconnected from it all, a subtle warning sign that something deeper was missing.
• Post-Traumatic Growth: Greg introduces the concept of post-traumatic growth — how trauma, while devastating, can also be the catalyst for deeper connection, strength, and clarity about what really matters.
• Kids as Anchors Through Grief: Greg shares how his children, then just 5, 2, and 1, helped guide him through the darkest moments. Their resilience and curiosity about loss shaped the family’s healing in profound ways.
• Love After Loss: We talk about Greg’s relationship with Whitney — how it began, how they built trust with the kids, and what it takes to blend a new chapter of life without erasing the old one.
• Living With Grief, Not Around It: Rather than “moving on,” Greg talks about carrying grief with you — honoring it, making space for it, and allowing it to shape how you live moving forward.
• Resilience Is a Skill, Not a Trait: Greg believes resilience isn’t something you have or don’t — it’s something you build. And it starts by doing hard things and choosing discomfort over autopilot.
• Vienna Waits: Greg and Whitney founded Vienna Waits to help people live more intentionally before the trauma hits — offering tools, community, and support for taking meaningful action toward a more aligned life.
• The Million-Person Mission: Their goal is to help one million people ask themselves a powerful question: “Am I really living the life I want?” And if not, “What the f*ck am I waiting for?”

Every other week, join your host Bob Mathers, keynote speaker for conversations designed to push you out of your comfort zone. Each episode delivers boundless insights and ideas that matter by inspiring you to get off autopilot and keep chasing curiosity.

Links and Resources

Greg on LinkedIn

Vienna Waits Instagram

Vienna Waits Website

UNBLOCK Yourself podcast

Waypoint Retreat

Connect with Bob Mathers

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