Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

In this special Collab Week episode of Wantrepreneur to Entrepreneur, four founders answer one powerful question:
What is an opportunity you almost ignored — but now realize changed everything?
You’ll hear from Jane Alexander of Emma Advisor, Shawn Sundsvold of GoldBear Media, Mike Gross of Michael J. Gross LLC and Management System Certification Training Solutions, and Nate Hebbert of SelfWare Consulting as they each share a moment they could have easily dismissed.
A bootcamp that felt intimidating.
A cold email that could have been deleted.
A coaching opportunity that seemed inconvenient.
A local resource that could have been overlooked.
Each story reveals the same lesson: some of the biggest entrepreneurial breakthroughs do not arrive looking obvious, polished, or perfectly timed. Sometimes they show up as discomfort, doubt, outreach, community, or an opportunity you do not yet feel ready for.
For any wantrepreneur or entrepreneur wondering whether to take the call, join the room, ask for help, invest in themselves, or say yes to the thing that scares them, this episode is a reminder to look twice. The opportunity that changes everything might already be sitting right in front of you.
✨ What You’ll Take Away
In this episode, you’ll learn how to:
Recognize opportunities even when they do not look like opportunities at first.
Bet on yourself when you feel underqualified, intimidated, or unsure.
Use new tools, AI, and accessible technology to move faster without waiting for permission.
Reframe cold outreach, local events, and free resources as potential doors instead of distractions.
Invest in personal growth before you feel “ready” to become the next version of yourself.
Build a stronger entrepreneurial support system so you do not have to figure everything out alone.
🎙️ Meet the Collab Week Contributors
Jane Alexander — Emma Advisor
Jane Alexander is the founder and CEO of Emma Advisor, an AI platform helping families navigate the path from high school to college with more clarity, strategy, and confidence. Her own path included homeschooling in rural Idaho, community college, transferring to a private university, graduate work at Harvard University, and more than a decade advising leaders at over 200 colleges and universities on enrollment, student success, and strategy. Emma Advisor grew from her belief that access to college strategy should not depend on money, insider knowledge, or social capital.
Connect with Jane:
Website: https://emmaadvisor.ai/
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 problems across business development, sales, marketing, operations, and management, Shawn joined his wife Kelly in building GoldBear Media full time. Today, they 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
Mike Gross — Michael J. Gross LLC / Management System Certification Training Solutions
Mike Gross is a trainer, training provider, consultant, and auditor who helps organizations make sense of ISO standards and apply them in practical ways. With more than 35 years of experience, including growth into executive leadership roles, Mike focuses on helping organizations build understanding through training first, then refine and improve their systems. As a committed solopreneur, his approach is practical, straightforward, and centered on leaving people more capable than when he started.
Connect with Mike:
Website: https://mj-gross.com
LinkedIn: https://www.linkedin.com/in/mj-gross/
Company LinkedIn: https://www.linkedin.com/company/michael-j-gross-llc/
LinkedIn Showcase: https://www.linkedin.com/showcase/mscertts/
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 solving one problem: how to escape the cycle of burnout. Today, he is the founder and CEO of SelfWare Consulting, helping tech companies beat burnout without pressing pause.
Connect with Nate:
Website: https://selfwareconsulting.com
LinkedIn: https://www.linkedin.com/in/beat-burnout
YouTube: https://www.youtube.com/@SelfWareConsulting
💡 The Opportunities They Almost Missed
Jane Alexander: The intimidating room that changed the trajectory of the company
Jane’s opportunity came through a bootcamp that felt outside her comfort zone. As a non-technical founder building an AI platform, it would have been easy to assume she did not belong in a room full of technical builders and Silicon Valley expertise. Instead, she said yes. That decision helped her learn new tools, build with more confidence, save significant money, and rethink what she was capable of creating herself.
Key reminder: Do not let your current skill set define the limits of your vision.
Mike Gross: The cold email that became a hidden door
Mike’s opportunity arrived in the form many entrepreneurs are trained to ignore: cold outreach. But instead of immediately dismissing it, he paid attention to the way the opportunity showed up — professional, persistent, respectful, and not overly demanding. A simple exploratory conversation opened the door to a global business opportunity that expanded what he thought was possible.
Key reminder: You do not have to say yes to every opportunity, but you should learn how to recognize signal through the noise.
Shawn Sundsvold: The coaching opportunity that expanded his vision
For Shawn, the opportunity was not a tool, lead, or sales call. It was personal development. At a time when he was still trying to figure out what business ownership could look like, coaching helped him see a different future for himself. It challenged how he thought about life, work, possibility, and what he was capable of building.
Key reminder: Sometimes the opportunity is not about the business yet — it is about becoming the person who can build it.
Nate Hebbert: The local resource that became a community
Nate’s story is a reminder that entrepreneurship does not have to be as lonely as it often feels. By exploring local business resources, libraries, councils, and community networks, he found support, connection, and momentum. One small step into a local ecosystem created a ripple effect of relationships and opportunities.
Key reminder: The support you need may already exist closer than you think.
🚀 Action Steps For Wantrepreneurs and Entrepreneurs
Look back at one opportunity you recently dismissed and ask whether it deserves a second look.
Say yes to one room, event, call, or learning opportunity that feels slightly intimidating but potentially expansive.
Take one low-risk exploratory call before deciding whether an unfamiliar opportunity is worth pursuing.
Search for local business resources in your city, region, library system, chamber, or industry community.
Invest in one personal development opportunity that challenges how you currently see your future.
Identify one AI, no-code, or automation tool that could help you build something you previously assumed you had to outsource.

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.

In this first-ever Collab Week episode of Wantrepreneur to Entrepreneur, four past guests come together to answer one powerful question:
What’s a tiny decision you made that changed everything?
You’ll hear from Stephen Custer of Dry Humor Marketing, Nate Hebbert of SelfWare Consulting, Drew Dorenfest of Client Magnet CRM, and Janice Kephart of ZipID as they each share a seemingly small moment that created a major ripple effect in their entrepreneurial journey.
From writing down a goal, to helping a friend for free, to saying yes to a terrifying opportunity, to using a job as a training ground for future business ownership, this episode is a reminder that transformation rarely starts with a grand master plan. More often, it starts with one small, decisive action.
For any wantrepreneur or entrepreneur feeling stuck, this episode offers real-world proof that the next move doesn’t have to be massive. It just has to be intentional.
✨ What You’ll Take Away
In this episode, you’ll hear how small decisions can become major turning points, including:
Why writing down your goals can help shape your identity and future direction.
How one free project can become the proof of concept that launches a business.
Why scary opportunities often become the moments that create credibility and confidence.
How your current job can become a paid training ground for your future company.
Why you don’t need perfect clarity to begin — you just need one committed step.
How tiny moments of courage, service, and curiosity can compound into major entrepreneurial momentum.
🎙️ Meet the Collab Week Contributors
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/
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 experiencing burnout firsthand, he 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
Drew Dorenfest — Client Magnet CRM
Drew Dorenfest is a marketing expert who has worked with global brands including Netflix, Apple, Warner Bros., the NFL, and more as a video editor. Today, through Client Magnet CRM, he helps small business owners grow their brands through more clients, more 5-star reviews, and more sales.
Connect with Drew:
Website: https://clientmagnetcrm.com
Janice Kephart — ZipID
Janice Kephart is the founder of ZipID and brings decades of experience at the intersection of law, policy, national security, identity verification, and biometric technology. Her work has included drafting the federal identity theft criminal statute, serving with the 9/11 Commission, contributing to REAL ID and biometric border entry-exit systems, and now building technology to bring greater trust and integrity to identity verification.
Connect with Janice:
Website: https://www.zipidapp.com
LinkedIn: https://www.linkedin.com/in/janicekephart/
💡 Key Lessons From This Episode
Define who you’re becoming.
Nate’s story shows the power of writing down your goals and allowing that act to shape your identity, attention, and future decisions.
Create proof before you chase perfection.
Drew’s story is a reminder that helping one person, even for free, can become the case study that gives you confidence and opens the door to paying clients.
Say yes before you feel ready.
Janice’s story reveals how one intimidating opportunity can become the moment that changes how you see yourself and how the world sees your expertise.
Use where you are to build where you’re going.
Stephen’s story shows how your current job, role, or environment can become the place where you develop the exact skills you’ll later use to build your own business.
🧠 Memorable Moments
“Your environment and the experiences that you've had in the past do affect who you are right now, but the future in so many ways is for you to decide.” — Nate Hebbert
“That small decision just to help a friend and try something changed everything for me.” — Drew Dorenfest
“It gave me the confidence that I had something to offer in a way that I never had it before.” — Janice Kephart
“I learned how to make videos that engaged people and educated them and most importantly caused them to act.” — Stephen Custer
🚀 Action Steps For Wantrepreneurs and Entrepreneurs
Write down one goal you want to grow into and keep it somewhere you’ll see it often.
Find one person or business you can help this week to create real-world proof of your skills.
Say yes to one opportunity that scares you but could stretch your credibility.
Look at your current job, project, or environment and ask: “What skill can I develop here that my future business will need?”
Stop waiting for the huge breakthrough and identify the tiny decision you can make today.

In this very special Solo Sunday episode, Brian shares his biggest and most personal announcement ever. After a decade of sharing his entrepreneurial journey on the show, he’s opening up about a life-changing milestone that is already profoundly shifting his perspective on business, priorities, and success. He ties this beautiful moment back to the single most important element of any business strategy: making it about someone other than yourself. If your motivation ever fades or you find it easy to pause when life gets hectic, this episode reveals the ultimate key to creating unstoppable momentum and accountability in your business.
✨ Why This Matters for You
Building your strategy around others isn't just a feel-good idea; it's a powerful business advantage:
It provides an unshakable purpose that fuels you through the toughest challenges.
It transforms your business from a self-centered project into a meaningful mission.
It creates built-in accountability, making it much harder to quit on your goals.
It forces you to think about service and value first, which naturally leads to greater success.
It gives you a reason to get creative and find solutions, even when you feel like pausing.
📝 Key Takeaways
Your Strategy Needs a "Who." A powerful strategy isn’t just about your "why" — it’s about who you are doing it for. When you build your goals around serving and uplifting others, your motivation becomes infinite.
A "Me-Focused" Strategy Is Fragile. When your business is only about you, it’s easy to quit, pause, or disappear when things get hard. There's no one else to answer to.
People Create Accountability. Whether it’s your family, your team, your clients, or the people you hope to inspire, making them part of your strategy ensures you show up consistently.
Service Is the Ultimate Motivator. Brian shares how his commitment to the podcast listeners is what drove him to find creative solutions to keep the show going during a hectic personal time, rather than stopping like he might have in the past.
Success Becomes a Shared Reward. Growing a business becomes infinitely more fulfilling when you see it as a vehicle to support your team, delight your customers, and be an example for your community.
🚀 Put It Into Action
This week, take a moment to redefine your strategy around people:
Who, besides yourself, are you building this business for? Write their names down or visualize them.
Is it for your family? To make your parents proud? For the friend who never believed in themselves? For the community that looks up to you?
The next time you feel like quitting or procrastinating, look at that list. Let your commitment to them be the fuel that drives your next action.
🔗 Stay Connected
Subscribe to the show so you never miss an episode
Connect with Brian on Instagram @imetbrian
Share this episode with a fellow entrepreneur who needs a powerful reminder of who they're fighting for

We’re often told that to grow, we need to do more, add more, and say “yes” to every opportunity. But what if the real secret to strategic success is doing less? In this Solo Strategy episode, Brian flips the script on traditional business strategy, arguing that what you choose not to do is just as important as what you do. Drawing on powerful examples from icons like Steve Jobs at Apple and retail giant Costco, Brian reveals how simplification and subtraction are not signs of retreat, but the ultimate power moves for creating focus, clarity, and explosive growth. If you feel bogged down by complexity and spread too thin, this episode is your guide to getting back to what truly matters.
✨ Why This Matters for You
Embracing subtraction as a strategy can fundamentally change your business:
It frees up your time, energy, and resources to double down on what’s actually working.
It sharpens your focus, allowing you to become the undeniable expert in your niche instead of a jack-of-all-trades.
It simplifies your operations, reducing overwhelm and eliminating the chaos that holds you back.
It positions you to attract the right opportunities and clients by making it crystal clear what you do best.
📝 Key Takeaways
Strategy is Subtraction. Deciding what not to do is as crucial as deciding what to do. Your "to-don't" list is as powerful as your to-do list.
Complexity is the Enemy. Your ego might love complexity because it feels impressive, but simplicity is what scales. Complexity creates chaos and kills momentum.
Focus Your Firepower. When Steve Jobs returned to Apple, he cut dozens of products to focus the company’s best talent on just a few. This intense focus is what created iconic products.
Less is More. Costco carries only 4,000 products compared to a typical grocery store's 50,000. This simplifies their business and strengthens their purchasing power. What can you simplify to strengthen your position?
Stop Doing What Doesn’t Matter. As Peter Drucker said, "There's nothing so useless as doing efficiently that which should not be done at all." Actively remove tasks, processes, and even clients that drain your resources without moving the needle.
🚀 Put It Into Action
This week, conduct a "subtraction audit" in your business:
Where are you offering too many products or services? Identify one thing you could remove to create more clarity for your customers.
Who is your "PITA" (Pain In The A**) client? What would it look like to strategically part ways and free up that energy for dream clients?
What is one task or workflow you do every week that doesn't produce a tangible result? As Brian did with his social media, just stop doing it and see what new opportunities arise.
🔗 Stay Connected
Subscribe to the show so you never miss an episode
Connect with Brian on Instagram @imetbrian
Share this episode with a fellow entrepreneur who is doing too much and needs to find their focus