Mental Challenges of First-Time Entrepreneurship

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Would you ever walk away from a "dream job" to start over from scratch? And if you've spent years building a career inside big brands, does it ever feel like it might be too late to launch your own agency? Most people talk about leaving their corporate job to chase something bigger. Very few actually do it, and even fewer jump without a parachute. Today's featured guest is one of those rare ones. After nearly two decades leading social, content, and influencer teams for household brands, he walked away from his so called dream job to start his own shop without any safety net. Today, he calls himself a brand guy who happens to own an agency.

Eric Gray is the owner of Maverick Content Studio, a twelve person, social-first agency for Fortune 500 brands. After a long and successful career in corporate, where he spent eighteen years building high performing social and content teams for companies like Universal Parks & Resorts, Eric realized he did not want the future he saw in front of him. He left Universal with two months of savings and zero clients. His story is a blueprint for leaders wondering whether to leave corporate and build something of their own

Today his team works with brands like Advent Health, Winn-Dixie, and Travel + Leisure, helping them build audience, loyalty, and relevance through social-first content.

In this episode, we'll discuss:

• Why target Fortune 500 brands?

• Why most agencies fail at building their own brand.

• Leaning on the power of personal brands.

• The hardest challenge of growing a young agency.

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Walking Away from the Corporate Dream Job

At age forty-one, Eric had success on paper but a growing dissatisfaction in real life. He was leading big teams, holding a prestigious role, and doing work others envied. But he felt stuck inside a corporate machine that limited purpose and impact.

Although he's thankful for the time he spent in that world, he didn't believe he was living his full purpose inside an organization with lots of bureaucracy. With the support of his family and his pastor, Eric decided he didn't want to get to his later years wishing he had taken more risks and took the jump to find out what could happen if he bet on himself.

Leaving was messy, scary, and absolutely not the playbook move. No freelancing ramp up. No contracted clients. It was no tidy transition. Yet he trusted that his experience and network would open the next chapter. Looking back, it did.

Why Target Fortune 500 Brands?

Most new agency founders start small. Eric went in the opposite direction. He targeted enterprise brands from day one because that is where his expertise lived. He had already built the blueprint inside Universal Parks & Resorts and believed he could help other brands treat social as more than an afterthought.

Eric knew many enterprise brands still underinvest in social. They focus on one big campaign or hero asset while ignoring the loyalty and connection that is built through consistent storytelling. His agency's entire model revolves around what he calls the connection strategy. It is the belief that brands win when they create emotional relevance around the stories customers already care about.

Furthermore, large brands have large scopes, which also means you do not need forty clients. You just need the right five. That became a core advantage as they started growing.

Building the Early Client List Through Relationships

Eric did not cold call or blast DMs. He leaned into what he had spent years building. A strong network with strong relationships. Most of their early clients came from people who had worked with Eric before, or from friends of those people inside other major brands. Big companies talk to each other more than you think.

This doesn't mean it was easy for them. They still have a lot of work to do to break through. But if you invest in your network before you need it, it becomes your biggest shortcut when you step into entrepreneurship.

Why Most Agencies Fail at Building Their Own Brand

But Eric points out that almost no agencies truly build their own brand. They hide behind their walls and hope referrals save them. Others talk about themselves, focusing mainly on their people, process, and portfolio. Meanwhile they tell clients to produce consistent content, invest in story, and build an audience.

When Eric launched Maverick, he refused to be another guy who leaves a corporate job and posts the generic LinkedIn announcement. He started building his personal brand alongside the agency's brand from day one, and worked with his wife to make his agency look and feel much larger than its actual humble beginnings from their home offce. Perception matters if you want to enter rooms above your weight class.

The Power of a Personal Brand

Eric leaned into his background in sports radio and launched the Radical Content podcast. Within a few months he secured major guests like the former CMO of Chick-fil-A, the head of digital for NASCAR, and leaders from Crocs and other major brands. Those interviews became relationships. Those relationships became visibility. And that visibility opened doors for the agency.

The agency's channels became secondary to Eric's personal channels. Not because the company brand did not matter, but because personal brand builds trust faster than corporate messaging.

Systems, Volume, and Practicing What You Preach

Eric put serious resources into his content system. It started rough, with a single producer who did not fully work out. But it evolved into an eight person content ecosystem producing weekly episodes, daily clips, statics, and text posts.

He treats his own brand as the test kitchen for the strategies they deploy for clients. When you do that, the content feels authentic and the results are real. For him, if you stay in the background and don't talk about who you are and what you do, you're losing valuable opportunities to build your audience. You should be the guinea pig for everything you sell.

The Hardest Challenge of Growing a Young Agency

Two types of struggles hit new founders: agency struggles and the first time entrepreneur struggles.

1. On the agency side, Eric is unrelenting on talent. He will not hire someone just because they have experience. Their standards are high, which means the search takes longer. Orlando is growing but not a major market for high level social and content talent. They once received nine hundred applicants for a creative director role.

2. On the founder side, the hardest challenge is mental. Building a company that feeds twelve families is a heavy responsibility. The expectations you have for where you think you should be often do not match where you actually are. That gap can mess with your head.

Eric uses a list of personal non negotiables to stay mentally sharp: hard morning workouts, time with faith, reading goals daily, taking short breaks during the day, reviewing priorities, and going to bed on time. The last one is the hardest for him. But like most discipline problems, skipping the basics is usually what leads to feeling off.

Why Agency Entrepreneurship Requires a Long Game Mindset

For Eric, entrepreneurship is staring the hard thing in the face and moving forward anyway, which is where his non-negotiables come in. For his part, Jason has always treated entrepreneurship as a game. Sometimes you do everything right and still get hit with a bad roll of the dice. The goal is not perfection. It is persistence.

The memories you keep are rarely the easy seasons. They are the nights you and your team fought through the hard stuff. For this reason, his advice for agency owners is to have fun along the way. Don't wait until your kids are grown or your agency is sold to live. Make the journey the part you enjoy.

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