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 Marketing because he believes marketing is seriously fun. He helps clients combine strategy, data, and authentic storytelling so they can inspire people to act instead of simply throwing ideas against the wall to see what sticks.

Connect with Stephen:
Website: https://www.dryhumormarketing.com/
LinkedIn: https://www.linkedin.com/in/stephen-custer/

Shawn Sundsvold — GoldBear Media
Shawn Sundsvold is the co-founder and COO of GoldBear Media, a marketing agency based in Westminster, Maryland. After years of solving business problems across sales, operations, management, and marketing roles, Shawn joined his wife Kelly full-time in GoldBear Media to help small and medium-sized businesses improve their marketing, branding, online presence, social media, email marketing, and growth.

Connect with Shawn:
Website: https://goldbear.media/
Instagram: https://www.instagram.com/goldbear.media/
YouTube: https://www.youtube.com/@GoldBearMedia

💡 The Questions That Shape Better Founders

Mary Gunther: “Is this CEO-level work?”
Mary’s question is a direct challenge to every entrepreneur who confuses motion with momentum. Not every task deserves the founder’s time, energy, or attention. If the business is going to grow, the leader has to grow too — and that means protecting the calendar, saying no more often, and focusing on the work only the CEO can do.

Key reminder: Busy is not the same as building.

Shawn Sundsvold: “Where can I buy back my time?”
Shawn’s question reframes time as something entrepreneurs can intentionally reclaim. Instead of assuming every task belongs on your plate, ask what can be delegated, automated, systemized, or handed off. The time you buy back becomes the space you use to lead your team, grow the business, and be present in the rest of your life.

Key reminder: You do not have to do everything yourself.

Brent Newton: “Why did it take me so long?”
Brent’s reflection is both personal and generational. As a first-time founder building myOwl alongside his daughter, he reminds us that entrepreneurship can start at any age — but when we see that spark in someone younger, we should nurture it. Sometimes the most important question is not just how we build, but how we help others believe they can build too.

Key reminder: It is never too late to start, and never too early to encourage someone else.

Stephen Custer: “Why not?”
Stephen’s question is simple, but powerful. Many founders default to asking “why?” from a place of fear, scarcity, or pessimism. But adding one small word — “not” — changes the energy of the entire question. “Why not?” opens the door to possibility, experimentation, hiring, scaling, and trying the thing you might otherwise talk yourself out of.

Key reminder: Sometimes your next breakthrough starts with a better question.

Nate Hebbert: “What is my highest priority right now?”
Nate’s question goes deeper than urgency. Your highest priority is not always the loudest task, the nearest deadline, or the thing someone else wants from you. It also includes your growth, your energy, and your ability to do quality work. For entrepreneurs especially, protecting your physical, mental, and emotional capacity is not separate from business performance — it fuels it.

Key reminder: Your energy is part of your operating system.

1484: The question I ask myself most often... (collab episode!)

Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

1484: The question I ask myself most often... (collab episode!)