Nick Grayson Bet on Himself. Then He Learned to Trust.

I.Seven a.m., every morning

Early on, Grayson was running NG Media, a freelance agency that was just him. He had saved about $15,000 from a corporate job he'd held for eight months. Then he moved to Nashville, which he admits "may not have been a great call at the time," because it's an expensive city and he didn't have much money. He watched the savings drain until his bank account sat at about zero.

So he set a recurring reminder on his phone. Every morning at around 7 a.m., the same three words lit up his screen: bet on yourself.

"I continued to bet on myself for like a long time," he said, "and I still do."

About a year ago, he changed it. He'd come to see that it wasn't all about him and that he couldn't do this alone. His faith had grown into a big part of his life. So one day he opened the reminder and typed something new: trusting God.

"Every day that pops up," he said, "and that's been huge for me."

II.The pressure, and the punch in the face

Ask Grayson who he is and he starts with a high bar. "Nick Grayson is someone who wants the best out of himself for the good of others," he said. He puts a lot of pressure on himself to use his strengths, because not using them would be "doing myself a disservice and I'd be doing others a disservice." That goes for his work, his health, and his faith. He said he isn't perfect, but he's made huge strides this year and he's proud of them.

The other half of him is the guy who doesn't take things too seriously. He tried to find the right word for it and landed on agile. He tries to meet everything with a sense of humor, partly because it makes life more fun and partly because he's paid the price for the opposite. "I've spent a lot of time being super stressed out, being super anxious, and it holding me back from whatever it is I was trying to achieve."

His rule for it is blunt. Put any one area of life on a pedestal and "you're just getting punched in the face. Every single time." What works better for him is just being himself, whether that's on a sales call, getting to the gym every day during the week, or showing up at church on Sunday.

III.He was the bottleneck

The line that stuck from the interview came when Jim asked how the person and the business fit together. "All of my business problems have been kind of disguised as personal problems," Grayson said. "And as I've kind of figured out the personal part, the business has gotten way better because I'm the bottleneck."

He walked through how it spirals. If he isn't sharp on sales, the company suffers. If he isn't building the right systems, they lose clients. Then the money stress comes back, he puts it on a pedestal, and it bleeds into everything else. When he skips the gym or isn't getting his steps in, or feels further from God, the stress shows up at work, and it goes the other way too.

Now that he has a team, he said, his energy spreads to them. "If I come in with the energy, right, that people buy into, you're going to have way better results in all areas."

These days he's selling, running the business, building operations and systems, and appearing on camera in a lot of the ads the team makes for clients. He thought that last one would push him out of his comfort zone. Mostly, it felt natural.

IV.The bar app and the bigger why

Grayson knew he was creative back in college in Kentucky, where he helped launch a food and drink specials app for local bars and restaurants. He ran its social media and found out he was "pretty witty," good at coming up with ideas and concepts.

He admits there's some irony in what he does for a living. "I'm sometimes very antisocial media, which is kind of ironic given I do social media for a living and I market apps." He worries about screen time like a lot of people do. What settled it for him was the products. A fintech app that helps people save or invest, a fitness app that helps them get in shape, a travel app that helps them see the world.

About a year into making ad creative for apps, he figured out his why. He wasn't only helping founders and growth teams hit their numbers. He was reaching the people on the other end of the ad. "That was a different unlock for me in terms of my motivation." It turned the work from a side project into a career.

His team's job, as he put it, is finding "creative that clicks for a given audience" so an app gets a lot of users at an affordable cost, and the right users, the ones who become paying subscribers. He treats it like a game. A fitness app needs one ad for "a mother of three trying to lose 10 pounds" and a completely different one for "a gym bro trying to gain 20."

V.The client who almost quit ads

Asked about someone whose life changed because of his work, Grayson picked a current client, a fintech app that had been running ads for two years, maybe three, and had never turned a profit. It was about to shut down its paid ads program. Grayson's team was, in his words, "kind of their last shot."

The first few ads his team delivered brought a 3x return on ad spend, and the client had its first profitable month right away. Over the next five months, the team scaled the client to 14 times its starting ad spend while staying profitable.

"That changed the whole trajectory of kind of like what their business model was and how they were going to grow," he said. It also opened doors for his own agency in fintech.

Part of what made it work, he said, is that he and his head of creative, Ryan, were in a lot of those ads themselves, and they were some of the top performers.

VI.Nashville Acting Studio

Grayson says he doesn't know a single other mobile app ad creative agency that puts its own team on camera. They sit in the client meetings and understand the customer, and then they go film the ad.

That skill came from somewhere unexpected. About a year and a half ago, before he'd filmed a single ad, he was working so much that he decided he needed a hobby. He signed up for an acting class at Nashville Acting Studio. "Shout out Rebecca Lions, the goat," he said. For four or five months he did on-camera scene work, learned lines, and worked with scene partners.

It gave him respect for actors. The hard part, he found, is "not just to memorize lines, but to really feel that emotion and put yourself in the mindset of that character." He doesn't claim to be great. "It helped me be good enough to be able to get on camera, deliver lines, and put things out there that are high converting."

Then Ryan came aboard. Grayson described him as one of the most successful UGC (user-generated content) creators in the space. Ryan started asking Grayson to jump into concepts with him, and the two had chemistry from the start: skits, street interviews, whatever the idea called for. Knowing how creators actually deliver lines now shapes the team's scripts and formats. "Just knowing how to lead from the front, like literally the front, it makes everything so much easier."

VII.Learn all of it, then hire killers

If he had to train someone to replace him, Grayson's first lesson is to get your hands into every part of the business from day one. "That's going to suck and you're going to be working a lot of hours, but you need to know everything." In his early days, back when he served real estate clients before apps, he did cold email, ran ads, wrote ad scripts, and built CRM systems in GoHighLevel. Along the way he learned to sell and build relationships.

He also learned where he wasn't the best. He taught himself paid media well enough to land clients and get decent results, and he knew that was the ceiling. So he had a choice: find someone cheap, or find "an absolute stone cold killer," even if it meant giving up some margin. He picked talent. "I'm just a collaborative person. I'm a social person. I need a team, right? So, might as well have a good one."

That's how Patrick, whom he hired to run media and now calls his co-founder, and Ryan, now his head of creative, ended up beside him. "Learn all of it," he said, "prioritize talent, and let them cook."

VIII.Trusting others

The reminder on his phone ties the whole story together. Betting on himself got him through the zero-balance months in Nashville. Trusting God, and trusting the people around him, is what took the pressure off.

"That's what happens when you put it all on yourself," he said. Handing some of it to others, helping them get better and giving them a platform, "and also trusting the Lord. I think that's been the biggest unlock for me."

Disclosure: Jim Morris, the editor of The Emerson Review, interviewed Nick Grayson for this feature on November 11, 2026.

About the Featured Leader

Nick Grayson

Founder and Head of Growth, RoundSquared

Nick Grayson runs growth at RoundSquared, a Nashville performance creative agency for mobile apps that makes ad creative and runs paid acquisition for consumer apps. Before RoundSquared he ran NG Media as a solo freelancer. More at roundsquared.io and on LinkedIn.