Most people who dream of leaving their corporate job never do. They wait for the right moment, the right market, the right amount in savings — and the moment never comes. Eric Winegard didn’t wait. At 40 years old, he walked away from a $500,000-a-year sales role, dissolved a marriage that wasn’t aligned with his vision, moved out of the zip code he’d lived in for four decades, and bet everything on himself.
Today, as CEO and co-founder of Rare Blue Moon Marketing, Eric runs an 8-figure digital marketing agency with 300+ clients — built from scratch alongside his wife. In a recent episode of Outside the Corporate Box, he shared the raw, unfiltered story of how he got there. This is that blueprint.
1. Commitment Means Eliminating Your Options — Not Just Deciding
There’s a version of entrepreneurship where you keep your day job, dip a toe in, and “see how it goes.” Eric tried the other version. He calls it burning the boats — a reference to the ancient military tactic where commanders would destroy their own ships upon landing, leaving their troops with no choice but to win or die trying.
For Eric, burning the boats meant making retreat psychologically impossible. He left behind financial security, a familiar environment, and relationships that didn’t support his goals. The result? His brain stopped looking for exit ramps and started solving problems.
"Commitment is the elimination of options. I made it to the point where there was no other option."
— Eric Winegard
This doesn’t mean recklessness. Eric is clear that not everyone has the psychological capacity for this approach — and that’s okay. But if you say you want entrepreneurial success, the question you have to answer is: do you actually want everything that comes with it?
2. It’s Never Too Late to Reinvent Yourself — Eric Started at 40
Eric grew up in a household where entrepreneurship was never discussed. No business talk at the dinner table, no role models who’d built companies. The path was clear: go to college, get a job, climb the ladder. And he did — becoming a top sales performer and eventually a sales leader at a marketing firm, earning half a million dollars a year.
But something kept pulling at him. The idea that he could build something of his own. It took until age 40 — and a level of self-belief he hadn’t previously found — to finally make the leap. He’s 46 now, and the message he wants every person who hears his story to walk away with is simple:
"It's never too late to reinvent yourself."
— Eric Winegard
His Navy background helped. Four years of military structure gave him discipline, adaptability, and an ability to receive direction while keeping an open mind — qualities that translated directly into running a company under pressure.
3. Sales Skills Are Your Entrepreneurial Safety Net
One of the fears that keeps professionals locked inside the corporate box is the terror of financial freefall. What if there’s no revenue? What if no one buys? Eric had a powerful answer to that fear: if you’re genuinely great at sales, you should never be afraid of going broke.
He didn’t launch into the unknown as a first-time hustler. He launched as a proven sales leader who knew how to walk into a room, build rapport, and close. His mental model was straightforward: even if he was a mediocre CEO on day one, he’d bring in money. The question was whether he’d do the right things with it.
When asked what he’d do if his entire company disappeared tomorrow and he had to start from zero, he didn’t hesitate. Put on a suit, comb his hair, go door-to-door to local businesses, sell consulting at $5,000 per month, build up 20 clients, and be making $1.2 million a year — then rebuild the agency from there.
"There's no such thing as an unemployed good salesperson.
If you're not selling, you weren't good at it."
— Eric Winegard
4. The Digital Marketing Mistakes Costing Small Businesses Money
As CEO of a full-service digital marketing agency, Eric has a front-row seat to the mistakes business owners make when investing in growth. The two that come up most often: spending too little, and failing to test.
On budget: if you’re an HVAC contractor running $1,000/month in Google Ads while your competitors are spending $10,000–$12,000, you’re not going to win. Underspending isn’t cautious — it’s ineffective. You have to be competitive to get results.
On testing: too many businesses run a single ad creative at $20/day and wonder why nothing converts. The answer is A/B testing — different hooks, different visuals, different on-screen talent — before committing budget. Scale what works. Kill what doesn’t.
And for any professional wanting to build a brand from scratch with zero budget? Eric’s answer is free: claim every major social profile, get comfortable on camera, post raw video, and do Facebook Lives. The platforms algorithmically reward live content — and authenticity outperforms polish every time.
5. The CEO Skill Set Is Different From the Sales Skill Set — Own Your Weaknesses
One of the most honest moments in Eric’s conversation comes when he talks about the gap between being a great salesperson and being a great CEO. These are different jobs. A salesperson executes. A CEO leads, hires, structures, strategizes, and manages people across every function of a business.
Eric didn’t go to business school. He didn’t have a mentor handing him an HR playbook. What he had was the self-awareness to know his gaps — and the ego-strength (he’d argue, the ego requirement) to invest in fixing them. He spends heavily on mentorships, masterminds, and high-level consulting specifically in areas where he knows he’s weak.
"Your ego should be big enough to realize you have weaknesses — and big enough that you want to improve them."
— Eric Winegard
His advice for anyone building a team: hire slow, fire fast. Pay up for quality. And surround yourself with people who are better than you at the things that matter — because that’s the only way to scale beyond yourself.
Key Takeaways
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- Commitment isn’t a feeling — it’s the act of eliminating your fallback options.
- Starting over at 40 (or 50, or 60) is not too late — reinvention has no expiration date.
- Strong sales skills are the most resilient foundation you can build a business on.
- Underspending on digital marketing is just as costly as wasting money on the wrong channels.
- The CEO skill set must be developed deliberately — acknowledge the gaps and invest in closing them.
- Authentic, raw content consistently outperforms polished production on social platforms.
Guest Bio:
Eric Winegard is the CEO and co-founder of Rare Blue Moon Marketing, a South Florida-based digital marketing agency that has scaled to 8 figures and serves 300+ clients across SEO, paid ads, AI automation, and tech stack consulting. A Navy veteran and former top-performing sales leader, Eric started his entrepreneurial journey at 40 and has been building ever since — with no plans to slow down.
Connect with Eric:
LinkedIn: https://www.linkedin.com/in/eric-winegard-93892717/
Instagram: https://www.instagram.com/ericwinegardofficial/
Rare Blue Moon Marketing Website: https://rarebluemoon.io/
About Outside the Corporate Box:
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