Episode Details

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 prac