Eric Winegard: From Adversity to Eight Figures—The Power of Reinvention and Grit | Ep 1085

Summary

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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

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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.

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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)

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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)

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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

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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.

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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.

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Transcript

[A]

Foreign welcome to Coruscant Technologies, home of the Digital Executive podcast. Welcome to the Digital Executive. Today's guest is Eric Weingart. Eric Weingart is the co founder and CEO of Rare Blue Moon Marketing. Eric Weingart's life is a testament to the raw power of reinvention, grit and the unyielding belief that one's past the does not have to define their future. From homeless shelters and foster homes to the helm of an eight figure business, Eric's journey is as inspiring as it is extraordinary. Determined never to squander the second chance he's been given, Eric resolved to completely change the trajectory of his life. Despite not having a high school diploma, he pushed himself to go back to school, earning his GED and later pursuing higher education. It was the beginning of an uphill climb, but Eric was no stranger to adversity. Together with his wife Alexis, Eric founded a digital marketing firm in South Florida. What began as a bold venture grew into an eight figure enterprise, serving clients nationwide with cutting edge digital marketing strategies, video production, SEO services and more. Their company quickly earned a reputation for excellence and innovation, outpacing competitors and transforming the marketing landscape for countless businesses. Well, good afternoon, Eric. Welcome to the show.

[B]

Thanks for having me, Brian. Excited to chat with you.

[A]

Absolutely, my friend. I appreciate it. You've been in South Florida there and I'm here in Kansas City. The weather's a little different. At least you get some breeze coming off the ocean if you're close enough anyway. But we're baking in the heat today, so I just appreciate you making the time. Eric, jumping into your first question, your journey from homeless shelters and foster care to building an eight figure business is remarkable. What was the turning point that made you believe true change was possible for you?

[B]

Well, I tell people I had two turning points in my life. One is a very young man. Very, very young man. When I was 23 years old, I was a knucklehead, Brian, the definition of it. I was selling narcotics and I was involved in the nightlife scene and just not living a good life at all. Coming from a background with single mother, no father, we had our challenges. And unfortunately, the world that took me in was the. Was the underworld somebody would like to call it. And I got arrested. And you know, to be candid, Brian, I should have went to jail for seven or eight years. And this is too long of a story for this podcast, but by the luck of God, I didn't get in any trouble at all. And that's when everything changed. You know, I realized you know, I had to take control of my own future. And I did. I went to college. I got a four year degree in two years. And then I started a successful career at a digital marketing company. And I just climbed my way up the corporate ladder, Brian. And by most people's standards, you know, I was making between 3 and $500,000 a year. And when you hit that level in your 30s and you come from the background that I've come from, you made it big time, right? By most people's standards, absolutely. And then the second paradigm shift I had is, you know, when I was 40, that company really wanted me to take on really the entire company and really be that company's leader and successor. And once Covid hit, it really messed with me a little bit, Brian. I realized that I had to take control again. I had to put my future and my results in my own hands. And after a 17 year, illustrious career climbing the corporate ladder, Brian, I resigned. And I, my beautiful wife and I moved from Rochester, New York, down to South Florida. We started our own digital marketing company. And yes, we had a couple of lean years, but, you know, the past couple of years have been explosive. So I had two paradigm shifts. You know, one is a young man and one is a grown man.

[A]

Thank you. That did summarize. I know the story could be a lot longer. We could probably have a three hour podcast like Joe Rogan, but we'll just skip that and do the short version for our audience. But it's important that you highlighted some of the things that were turning points. You were arrested at a young age. You lucked out and skipped out a big sentence, which is great. And then, of course, as you got older and wiser, you had this massive opportunity. At the same time, it just wasn't hitting your heart the right way. And to make a decision to just quit and then move and start your own gig is no small feat. So I appreciate you sharing your stories with our audience today. Eric, you spent 17 years climbing the corporate ladder before launching your own business. What lessons from that corporate experience help you the most as an entrepreneur?

[B]

Thousands. And the way I like to compare it is it's not that the company I was working for was perfect. It's not that they were completely imperfect. Like any organization in the world, they have strengths and weaknesses, right? Even Apple probably has some weaknesses somewhere. Right? And what I realized was, is that I can learn. 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 that I don't agree with, I can choose to not repeat that. So when I started my own organization at the age of 40, 41, almost, I really tried to take everything that I learned from sales, marketing, accounting, sales training, culture. I really tried to take all the good things and then some of the strategies that I felt were softer and on the weaker end, I said, you know what, I'm not going to go down those roads. I'm not going to make those mistakes. So really I feel like I've been blessed because that 17 year run really put me in prime position to be a very successful entrepreneur very fast. Whereas 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.

[A]

Thank you, that's very helpful. Spending that time nearly 20 years in that corporate job, racing through the ranks and learning so much absolutely contributed to your business and your business success, which is really cool. And again, you do learn a lot. As you get older, older, you get wiser. We know that. And you took all those great things and strategies that worked well and left the stuff that didn't work so well behind. So I appreciate that. Eric, your company is known for digital marketing innovation. What do you, you think sets your firm apart in a crowded and competitive landscape?

[B]

Oh, great question. And I get this question every day. Every company is going to say they're the best. Every company is going to say they have this strength here or this weakness here and they'll focus on the strengths. Obviously where I know we're different is my beautiful wife who's been the biggest blessing in my life is also my 5050 business partner. And she has a not the same tragedy that I had as a young man, but she definitely had some heartache growing up as well. She didn't have an easy climb either. So her and I are, you know, we have several dozen employees, but we're 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. So when a client invests with us, Brian, we know they're not just investing with their company's dollars. We look at it like they're investing with their family's dollars. And we know the decisions that they're making and the marketing decisions we're trying to help them remedy and make great. We know it's impacting not just their businesses bottom line, but their family's bottom line. There are no Other owner operators like my wife and I that are more passionate about helping the people behind the business, love that.

[A]

That's something that really, truly resonates with me. You truly care, you and your wife. You know that 5050 partnership light partner blessing, as you called it. Looking beyond the transaction in really trying to help folks out means so, so much. And I think your message is definitely going to resonate with our audience and I just love that story. So thank you. Eric, last question of the day. Many people feel trapped by their circumstances or past mistakes. What advice would you give to someone who wants to reinvent their life but doesn't know where to begin?

[B]

This is a very, very long conversation, but once again, I'll keep this today here. I believe there's a huge difference between traits and skills. And traits are what Tom Brady is famous for. Traits. You know, heart, character, work ethic and skills are in the business world, coding or graphic design, 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. Your work ethic and your character, those are the things that are going to matter the most. So in my humble opinion, what I think people need to do is they have to get their mind, body and spirit right before they take some monumental leap. For me personally, Brian, I had to lose 30 or 40 pounds. 40 pounds, get in the gym and start to feel good about myself. And once I started to feel good about myself, my energy went through the roof, my confidence went through the roof, and I was ready to risk take. If you're not in a good mind, body and spirit situation, risk taking becomes very, very difficult. But I want to leave it on this note. Traits will make you great.

[A]

That's awesome. Thank you. Appreciate that. And I like how you break that apart. Traits and skills. And we see a lot of entrepreneurs, successful ones, definitely lean on that trait side, which I think is important. You mentioned like heart, character, work ethic, that sort of thing. And you've got to have your mind, body and spirit all pulled together in the right direction. And I just love what you're doing with that. A lot of people have some great skills, but until you really settle that in your heart, make that decision and pull those traits together, you know, you're just not going to be a successful entrepreneur in my opinion. And what I've seen speaking to, you know, 1100 guests on the show. So I appreciate that. Eric, it was such a pleasure having you on today and I look forward to speaking with you real soon.

[B]

Thank you, Brian. Pleasure, my friend.

[A]

Bye for now.