Episode Details

In this special Collab Week episode of Wantrepreneur to Entrepreneur, five founders answer one deceptively powerful prompt:

What is the single most important question you ask yourself to stay focused, make better decisions, and keep building?

You’ll hear from Brent Newton of myOwl, Mary Gunther of The Social G Co., Nate Hebbert of SelfWare Consulting, Stephen Custer of Dry Humor Marketing, and Shawn Sundsvold of GoldBear Media as they each reveal the internal question that helps guide their work, energy, leadership, and growth.

From asking whether something is truly CEO-level work, to buying back time, to protecting your energy, to shifting from “why?” to “why not?”, this episode is a masterclass in the questions that shape better entrepreneurs.

For any wantrepreneur or entrepreneur feeling stretched, distracted, overwhelmed, or unsure where to focus next, this episode will help you rethink the conversations you’re having with yourself — because the quality of your questions often determines the quality of your next move.

✨ What You’ll Take Away

In this episode, you’ll learn how to use better questions to:

• Filter your to-do list down to the work that actually moves the business forward.
• Identify what can be delegated, automated, or eliminated so you can buy back your time.
• Reframe doubt and hesitation into possibility and action.
• Protect your energy as a real business asset, not a luxury.
• Clarify your highest priority by factoring in urgency, growth, and personal capacity.
• Recognize and nurture the entrepreneurial spirit in yourself and others.

🎙️ Meet the Collab Week Contributors

Brent Newton — myOwl
Brent is the co-founder and CEO of myOwl, an AI-powered platform helping student athletes and their families take back control of their time. Built around the “Play Hard, Study Smart System™,” myOwl combines homework aggregation, sports schedule syncing, and AI-generated study plans into one unified calendar. Brent built the company alongside his daughter after living the student-athlete time crunch firsthand.

Connect with Brent:
Website: https://www.getmyowl.com
LinkedIn: https://www.linkedin.com/in/brent-newton-myowl

Mary Gunther — The Social G Co.
Mary Gunther is the founder of The Social G Co., a Grand Rapids-based social media agency helping brands build strategic, authentic, impossible-to-ignore social presences. With a background in organizational development, HR, operations, community-building, and brand strategy, Mary brings a sharp mix of creativity and business growth to the companies she serves.

Connect with Mary:
Website: https://www.thesocialgco.com
Instagram: https://www.instagram.com/thesocialgco/
LinkedIn: https://www.linkedin.com/in/marykgunther/

Nate Hebbert — SelfWare Consulting
Nate Hebbert is an entrepreneur and software engineer who previously worked for 3M, KPMG, and Domo, where he developed custom Java code for Fortune 500 clients. After burnout threatened to derail his career, Nate became obsessed with helping tech companies beat burnout without pressing pause. Today, he is the founder and CEO of SelfWare Consulting.

Connect with Nate:
Website: https://selfwareconsulting.com
LinkedIn: https://www.linkedin.com/in/beat-burnout
YouTube: https://www.youtube.com/@SelfWareConsulting

Stephen Custer — Dry Humor Marketing
Stephen started Dry Humor Market