From Rock Bottom to $100M: The Startup That Changed Everything

This is the story of how Casey Holiday went from working at a restaurant to selling over $100 million worth of silicone wedding rings from his mom's living room.

A Regular Guy with an Unexpected Idea

Casey grew up like most kids - playing sports and chasing dreams. One of those dreams was moving to LA to become an actor. But his plans shifted when he met his future business partner, Ted.

Ted, who managed a restaurant in Beverly Hills, invited Casey to work with him. A few months later, they both got married. One day, while working together at the restaurant, they realized they had the same problem.

Casey: "Hey man, are you wearing your wedding ring?"

Ted: "Yeah, but it's a pain. Every time I work out or play golf, I take it off. I always forget where I put it."

Both agreed - it didn't make sense to wear a Rolex to the gym, just like it didn't make sense to wear a metal wedding ring for active lifestyles.

Casey: "Let's see if anything like this exists."

After searching, Ted came back with an answer.

Ted: "I couldn't find anything. It doesn't exist."

And just like that, the light bulb went off.

Starting with Nothing

With zero business experience but tons of excitement, Casey and Ted decided to take a chance.

Casey: "We had this handshake agreement - Ted had some savings, I had time and energy. We decided to put everything we had into this. My goal was simple: replace my $2,000/month restaurant income."

They didn't call it "finding product-market fit" or "bootstrapping." To them, it was just two broke guys trying to figure out how to sell a product.

Casey: "When you're starting something, you don't know what you don't know. The best way to learn is to talk to people who do."

Crashing a Business Meeting

Ted had an idea.

Ted: "I have a friend with a manufacturer in town. What if we crash his meeting at this fancy LA hotel?"

Casey: "Sure, man. Let's go for it."

They showed up with a couple of cheap rings from a local store and pitched their idea: "Can you make these out of silicone?"

Manufacturer: "Yeah, sure. Why not?"

Financial Struggles & Early Sacrifices

They pooled their savings and bought the first batch of inventory. But there was a problem.

Casey: "I didn't even want to look at my bank account. Ted had a family and was risking more than I was. We had emptied our savings."

Casey and his wife moved in with his mom. She worked the 11 AM shift at the restaurant while Casey worked the early morning shift.

Casey: "She would sleep in our little red Fiat in the restaurant's back lot until her shift started. Bless her."

Their home became their office, their dining table their workspace, and Ted's garage their warehouse.

The First Big Mistake

After months of waiting, the first batch of rings arrived. But they were terrible.

Casey: "The quality was awful. They were unsellable."

They had two choices: shut down or fix the product.

Casey: "I found a tiny pair of eyebrow scissors and started trimming the rings myself. It worked."

For weeks, they hand-trimmed 50,000 rings, watching all six seasons of Lost while doing it.

Casey: "We had ring shavings everywhere - in our house, on our cat, in our bed. That was our life."

Finding Customers

The website was built. The product was ready. They launched.

Casey: "And then… crickets. No visitors. No sales."

With no budget for ads, they had to get creative. Casey reached out to Andy Dalton, then the Cincinnati Bengals quarterback, through his wife.

A few months later, Andy was featured on Hard Knocks on HBO, wearing the ring.

Casey: "The next day, we did 3–4x in sales. Orders stretched across my mom's house. It was validation."

But two days later, sales slowed again. The real challenge had just begun.

Going All In

With growing sales, Casey made a bold decision.

Casey: "I told Ted, 'I think I should quit my job at the restaurant and go full-time.' He said, 'We can't afford that.' But I took the risk. That moment changed my life."

As sales skyrocketed, they hired employees, moved to a real office, and scaled fast.

Casey: "We went from 13 people in a tiny office to hiring 2–3 people a month. Soon, we had 100 employees and were doing $30 million in revenue at a 20% profit margin."

Lessons from Building a Business

Looking back, Casey shares some key takeaways:

Start with the problem. "Figure out what problem you're solving before creating a product."

Launch before it's perfect. "Get it into customers' hands and improve from their feedback."

Don't be afraid to fail. "Nobody is thinking about you as much as you think they are. Just start."

Final Thoughts

Casey: "If you have an idea and you're scared of what people will think - remember, nobody's thinking about you. Find a problem, solve it, and take action."

Inspired by Casey's Story?

If Casey's journey inspired you, check out Starter Story - a platform where founders share real insights about launching businesses. Download our worksheet on "99 Million-Dollar Problems Worth Solving" in the description below

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