The Digital Executive – Ep 1085:

Eric Winegard: From Adversity to Eight Figures—The Power of Reinvention and Grit
Date: July 18, 2025
Host: Brian (Coruzant Technologies)
Guest: Eric Winegard, Co-Founder & CEO, Rare Blue Moon Marketing

Episode Overview

This episode spotlights Eric Winegard’s extraordinary transformation from a turbulent youth—marked by homelessness and the criminal underworld—to heading an eight-figure digital marketing agency alongside his wife, Alexis. The conversation revolves around pivotal life moments, lessons from the corporate world, entrepreneurial values, and hard-hitting advice on self-reinvention.

Key Discussion Points & Insights

1. Eric’s Early Life and Turning Points

• First Major Shift – Arrest & Redemption:

  • At 23, living recklessly and involved in illegal activities, Eric was arrested and narrowly avoided a lengthy prison sentence.
  • This “luck of God” moment changed him permanently, prompting a return to education (GED, college degree in two years) and kickstarting a successful corporate career.
  • Quote: “I realized you know, I had to take control of my own future.” (02:45)

• Second Major Shift – Leaving Corporate Success:

  • After climbing to the top in digital marketing, earning $300,000-$500,000/yr, Eric had another awakening at age 40.
  • Amid the uncertainty of Covid, he felt compelled to control his destiny again, resigning after a 17-year tenure.
  • He and his wife Alexis left Rochester for South Florida, founding Rare Blue Moon Marketing despite “a couple of lean years.”
  • Quote: “I had to put my future and my results in my own hands.” (03:33)

2. Lessons Gained from Corporate Experience

• Eric accredits his 17 years in corporate life for providing a “prime position” to succeed in entrepreneurship, absorbing both best practices and lessons on what not to do.
• He emphasizes learning from both organizational strengths and weaknesses, then curating his own entrepreneurial toolkit.
• Quote: “I can take all the good that this company does, and then I can also learn from some of the things that I don’t align with... I can choose to not repeat that.” (04:53)
• Eric believes that wisdom and experience were instrumental to his rapid business growth; leaping at 25, he “very unlikely” would’ve succeeded as he did starting later.

3. What Sets Rare Blue Moon Marketing Apart

• Deep personal investment: Eric and Alexis lead as a “mom and pop” operation at heart, never losing sight of the real people behind client businesses.
• Shared adversity bonds the leadership, lending a grounded and passionate approach to serving clients.
• They view clients’ investments as family money, not just business capital, aiming for an authentically caring partnership.
• Quote: “There are no other owner-operators like my wife and I that are more passionate about helping the people behind the business.” (07:22)

4. Advice for Those Seeking Reinvention

• Eric encourages distinguishing between “traits” (work ethic, character, heart) and “skills” (technical abilities).
• He declares: “Skills will pay the bills, but it’s really your traits that will make you great.”
• Personal readiness is key—he recommends working on “mind, body, and spirit” before taking risks.
• His own transformation involved losing 40 pounds and regaining confidence; only then did he feel ready to risk everything.
• Quote: “Traits will make you great.” (09:15)

Notable Quotes & Memorable Moments

• Redemption & Change:
  “I should have went to jail for seven or eight years... by the luck of God, I didn’t get in any trouble at all. And that’s when everything changed.” – Eric (02:15)

• On Corporate Lessons:
  “If I just tried to make that jump at the age of 25, very unlikely, I would have had the same success as fast as I did.” – Eric (05:44)

• On What Makes the Company Different:
  “Her and I are... still a mom and pop. That’s how we look at ourselves. And the two of us couldn’t be more human and grounded than any other CEO and number two at any other company.” – Eric (06:42)

• The Essence of Reinvention:
  “The skills will pay the bills, but it’s really your traits that will make you great. And I’ve never even said it like that before, but it couldn’t be more true.” – Eric (08:25)

Timestamps for Important Segments

• Eric’s Background and First Turning Point: 01:50–03:36
• Second Shift & Founding Own Business: 03:36–04:25
• Corporate Lessons Applied to Entrepreneurship: 04:39–05:52
• Company’s Differentiators: 06:22–07:39
• Advice for Reinvention, Traits vs. Skills: 08:09–09:23

Tone & Style Notes

Eric’s language is candid, direct, and humble, peppered with gratitude for his second chances and praise for his wife and partner. The episode is motivational, energetic, and human-focused, sticking to the “real talk” rather than business jargon.

Summary Takeaway

Eric Winegard’s journey is a moving blueprint for anyone facing adversity or considering personal transformation. His story testifies to the power of unshakable grit, learning from one’s environment, leading with humanity, and prioritizing character over skill in both life and business.