From Red Lobster Waiter to a $250 Million Business
I heard a story recently that perfectly captures the journey most entrepreneurs face. A young man’s mother looked at him and said something he dreaded hearing: “You are going to have to go back to being a waiter at Red Lobster.”
He hated that job. The restaurant had just rolled out its free cheddar biscuits, which meant more work for plummeting tips. His small apparel company had already seen a glimpse of success—LL Cool J was a fan and orders were coming in. But now, he was being told to go back to waiting tables?
The hard truth was that they were out of options. They had mortgaged his mom’s house, sold everything they could, and still couldn’t afford the supplies to fulfill their orders. They’d made a rookie mistake, letting retailers order on terms that were great for the stores but terrible for them, with up to 120 days to pay. This is a common challenge when ; cash flow is everything.
So, he reluctantly went back to work. He trusted his mom, who had literally bet the house on him, and promised to earn the $2,000 she asked for. When he finally handed over the cash, she revealed her plan: she was going to buy a direct-response ad in to find an investor. He thought it was a crazy idea, but she moved forward with faith and placed the ad. It read: “Need partner to help fund 1 million dollars in orders. Serious inquiries only.”
Most of the calls weren't exactly legitimate, but a few were. They ended up striking a deal with Samsung Textiles to underwrite their manufacturing. That entrepreneur was Daymond John, the founder of the clothing line FUBU, with a current net worth of around $250 million. His journey shows how a dream becomes reality, but it's never an easy path.
The Unseen Struggle Is Universal
Daymond John’s story is incredible, but the struggle behind it is not unique. I haven’t met a single successful person who didn’t have a story filled with long hours, fear, sacrifice, and failure. My own company struggled for years. For the first decade, I thought about quitting at least once a year, even applying for jobs just to imagine an easier life. Thankfully, I never got a single call for an interview. I guess I’m just not built to work for anyone else, and if you’re reading this, you probably aren't either.
Simply by engaging with content like this, you’re already in a select group. Research has shown that nearly a quarter of American adults don't read a single book in a year. You’re seeking something more for your business and your life. The key is to start small. Focus on your best customers, find more people like them, and create great content. When you start dabbling in paid ads, keep a close eye on your return.
The Biggest Mistake in Side Hustle Marketing
One of the most important rules in marketing is that you should never try to be everything to everyone. This is where so many businesses go wrong, especially on social media. They see a trending topic and jump in without understanding the context, all in an effort to seem relevant.
Remember what happened with DiGiorno Pizza? A few years ago, the hashtag #WhyIStayed was trending on Twitter as a serious conversation about domestic violence. DiGiorno, seeing the trend but not the topic, tweeted, “#WhyIStayed You had pizza.” The backlash was immediate. Their excuse? They “didn’t know what the hashtag was about.” In the world of , ignorance is not an excuse—it's a liability.
Social media can be a powerful asset, but only if it’s getting you dollar-measured results. It should complement your other marketing efforts—like email or direct mail—not replace them. Chasing every new platform is a recipe for a watered-down strategy. It makes far more sense to hit a home run with one network than to spread yourself too thin across many.
A Smarter Path Forward
If you're serious about or growing a product-based one, you need to follow a few foundational rules for your marketing. These aren't flashy, but they work.
First, don’t just copy an ad because it looks cool. Kmart’s “Ship My Pants” video went viral, but did it actually drive sales? The company’s sales were down again the next year. A viral moment doesn't always equal profit.
Second, niches bring riches. There are specific groups, associations, and communities for almost every interest imaginable. Facebook’s tools are incredibly powerful for researching these audiences, even if you never spend a dime on ads. When you do advertise, make sure your message is tailored specifically to that niche. Too many businesses use the same generic ad for every audience segment.
Finally, base your strategy on facts, not guesses. The best way to do this is to get to know your customers. A simple survey can reveal what they truly want and need, identify opportunities for improvement, and even help you create a compelling freebie, like a report or an ebook, that solves a burning problem for your ideal prospect.
Your work has value that deserves to be shared with the world. The journey from a small project to a sustainable business—a true transition—is challenging, but it starts by finding the people who need you and serving them well.
