Ramon Ray on Getting Fired, Selling Businesses, and ‘the Celebrity CEO’ Framework
Ramon Ray didn't quit his job at the United Nations. He got fired. Specifically, his contract wasn't renewed because he refused to stop running side hustles after someone got jealous and complained.
He had a wife, two kids, and a few months of money in the bank.
He didn't have a backup plan.
What he had was 20 years of relationships and a willingness to pick up the phone.
This week on Success, Rewritten, Ramon shares the story of getting fired from the UN, building five companies, selling three of them, recently writing The Celebrity CEO, and the entrepreneurial depression he still navigates today.
The Side Hustle That Built Everything
Ramon started his career at the United Nations right out of high school. He worked there for many years, eventually getting promoted into a role that required him to finish his college degree.
Outside of work, he was already building. He bought his first domain in April 1999, back when launching anything online meant downloading a Mozilla browser, saving your blog file, and FTPing it manually to a server.
"AOL, Prodigy, CompuServe," he says. "Before blogging was popular, you would save your blog several times and FTP it."
He started Family Computer Consulting Services, installing modems and motherboards. Then he bought smallbiztechnology.com and started interviewing early players in the space. He grew an event business at the UN. He had permission for the side work.
Until he didn't.
Why He Got Fired (and What He Did the Next Day)
Someone at the UN got jealous. They escalated. Ramon was investigated. His permission to side hustle was pulled.
He didn't stop.
"I didn't stop after the permission was taken, because I already had a bite of the entrepreneur apple."
A DHL letter arrived on a Wednesday. Three days notice. By Friday, his contract was over.
He had a young family. He had a stay-at-home wife who, in his words, held the home and never stressed him about the money. He had enough in the bank for a few months of draws.
He had to make it work.
How to Ask for Money After Losing Your Income
Ramon's strategy after getting fired was specific, and counterintuitive.
He refused to lead with the story of getting fired.
"I wouldn't carry the story, 'I've just been fired, need your help.' Wrong way to approach people."
Instead, he picked up the phone and called the brands he'd been working with. He didn't ask for help. He pitched their next event. "Hey, I know we're gonna do an event in six months. Could you have some budget to fly me there, give me a hotel? Maybe you can give me an honorarium of 3,000, 4,000."
Do that over and over again, he says, and that's how you build a book of business.
He also said yes to writing gigs at one dollar per word. The trick wasn't the rate. It was the volume. "Then I kept reading, and they said, 'Could you write 5,000 words?' I said, 'Whoa, stop, stop, stop. 5,000 words?'"
The chintzy rate isn't the rate. It's the start of the conversation.
Selling a Business Isn't What You Think It Is
Ramon has sold three companies: Small Business Summit, smarthustle.com, and smallbiztechnology.com.
He's honest about what selling actually means.
"Selling a business, it means different things to different people. You could sell the business and lose money. You could've sold the business and had a massive amount of debt and saw none of it. You could've sold the business and the IRS took half of it."
The first sale was a good feeling. The hindsight was the lesson.
"How can I be smarter regarding paying the IRS? Can I try to be a bit more debt-free so when I sell it for $2, I'm not giving up $2 to pay off something else?"
The number you celebrate is rarely the number you keep.
Why 20 People in a Room Beats 300
Ramon's newest project is Genius Talks Events, an intentionally small format. Twenty to thirty people in a room.
He's done the big events. He's good at them. They're great for sponsorships and visibility.
But he's been told the small rooms create something the big ones can't: real conversation, real introductions, real value.
"Imagine me and you and 18 of our high-value friends. The person who knows this president, the person who knows that million dollar deal, the person who knows MrBeast. That, that's what I'm aiming to bring together."
It's a niche-down move from someone who could go bigger and chose not to.
The Celebrity CEO Framework
Ramon's most recent book, The Celebrity CEO, lays out a personal branding framework he's been refining for years.
It's three parts: attraction, trust, sale.
Attraction is the work of getting known in your market. Awareness, visibility, presence.
Trust is what makes a sale possible. It's built through consistency, content, and showing up.
Sale is what closes the loop. It's the easiest part if the first two are in place.
"Sales are good. Everybody wants the money. But the only way you can make a sale is if you've built trust. And the only way you can build trust is how do people know who you are."
His central claim is that this isn't reserved for the founders with massive followings.
"Everybody can be themselves and make a bigger impact in their personal brand."
On Entrepreneurial Depression
Ramon has spoken publicly about depression and self-harm. He gave a talk on entrepreneurial depression at South by Southwest.
He doesn't perform the version of himself that only laughs.
"I've suffered with darkness and pangs of depression, and I'll use the word self-harm."
He's healed in his own framing. But he's clear that even at 53, with the wins, with the books, with the brand partnerships, the dark days still come.
"Even as I sit here today, I could be going into, not a deep funk, but I have to be careful. It's quiet. Nobody's here. Did I do a good job? Maybe Emily really doesn't even like me. Maybe I'm a loser because I don't have as many page views as the next guy."
He says the noise of being around people fills him. The quiet is where it gets tough.
"It's in the silence. It's in the early morning when maybe the payment didn't come through and I gotta pay some family stuff."
The guardrails don't go away when the business takes off. He's still using them.
Find Ramon Ray
Website: RamonRay.com
LinkedIn: Ramon Ray
Instagram: @ramonraysmarthustle
His platform: Zone of Genius
If this conversation gave you a clearer way to think about your next move, you'll find more episodes and insights at Success, Rewritten. It's all there to help you keep moving forward and build something that actually works for your life.
