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.

1485: The opportunity I ALMOST ignored! (collab episode!)

Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

1485: The opportunity I ALMOST ignored! (collab episode!)