Elizabeth Calzadilla (Business 411)

Elizabeth Calzadilla is the owner of Business 411, a Miami-based marketing company that specializes in business growth solutions like branding, advertising, and automation.

Born in Yonkers, New York, Calzadilla and her family quickly moved to North Carolina in search of a better life, but as Calzadilla entered her formative teenage years, things quickly unraveled, resulting in her leaving the public school system before she could complete high school.

“I got expelled on two different occasions, and I ended up dropping out,” Calzadilla reveals.

Forced to enter the workforce at fifteen years old, Calzadilla started waitressing at a local restaurant, but within a year she had already tapped into her entrepreneurial spirit by starting an agency that booked women for photo shoots and roles in music videos.

“I recruited around thirty women, ranging in ages from 18 to 35. I took their headshots and added my company logo next to them. I started building their portfolios and trying to find them jobs,” Calzadilla recalls of her first business venture.

“That experience was my first failed attempt at being an entrepreneur, and I say failure because I learned that type of industry was not one that I wanted to be in long-term.”

Possessing a burning desire to escape the shackles of financial constraint, Calzadilla then contemplated departing from North Carolina, a state she says was, and still is, plagued by ignorance and blatant discrimination.

“Parts of North Carolina are very different. There’s still a lot of racism there,” Calzadilla notes.

A child of Cuban immigrants, Calzadilla was persecuted by many for the color of her skin.   

“I experienced racism from white and black people, but also from Hispanics who judged me because I was Cuban,” Calzadilla says.

“I was too dark for white people, and too light for brown and black people.”

This helps explain why, upon turning eighteen, Calzadilla bolted for Miami, where she quickly found gainful employment in the service industry, while also enrolling in community college as she pursued becoming a nurse.

That initial move appeared to be working out well for Calzadilla.

“I was making anywhere from $500-$1,000 a day at eighteen years old,” she says. “I would work weekends and go to school during the week.”

Still, it didn’t take long for Calzadilla to realize that becoming a nurse wouldn’t automatically mean she would be making more money than in her current job as a waitress.

And with the cost of tuition forcing her to take out loans, Calzadilla opted to forgo her nursing program and instead optimize the skills she already had in order to create a better life for herself.

In her case, this meant exploring the ways her dogged determination and affable personality could lead to long-term financial stability.

Friends and family suggested she go into sales, but after applying to dozens of businesses around South Beach, Calzadilla learned that her inexperience was causing companies to pass on hiring her. 

“It was crazy because what I didn’t know beforehand was that a lot of companies don’t want someone who has never sold anything before,” Calzadilla says.

“Since I had never sold anything before, no one would hire me.”

At the same time, all Calzadilla wanted was an opportunity, so instead of retreating back to the service industry, she bet on herself and took a job selling cable TV door-to-door.

That experiment only lasted a few weeks, at which point she pivoted and began working at a mall selling lotions and other beauty products to women.

That position also wasn’t a great fit, but Calzadilla never stopped trying to find a role that best catered to her strengths.

“That’s how I got into roofing,” she says.

Soon, Calzadilla was hired by iRoofing, a software company that delivers roof measurements to contractors via satellite imaging.

But working at iRoofing as a communications manager wasn’t glamorous.

For starters, the company’s office was in a rough part of town.

“And none of the furniture matched,” Calzadilla says with a laugh. “There was a tiny little stairway and one bathroom for the entire building.”

That being said, iRoofing was willing to give Calzadilla an opportunity, and for the next five years she helped the software company grow.  

During that time, Calzadilla’s entrepreneurial spirits also made a resurrection.

In addition to working forty-plus hours a week at iRoofing, she also spent her weekends doing hair and makeup for weddings and other events.

Having a side hustle was rewarding, but once again Calzadilla eventually found herself not seeing a long-term future in that line of work.

“Doing hair and makeup was fun, but it was very labor-intensive,” she says.

“Looking back, I’m happy that I went through it because it made me realize that in order to build foundational success, it wasn’t about what I could do with my own two hands, but what I could create with my mind and then have other people help bring to fruition.”

Calzadilla’s business-related epiphany coincided with returning to iRoofing after taking maternity leave, plus the continuation of her ideas being consistently thwarted by the brass at iRoofing.  

“All the marketing ideas that I execute now I actually gave to them [iRoofing] first, but they didn’t want them,” Calzadilla says.

This confluence of factors, along with roofing contractors in Miami routinely inundating her with job offers to run their marketing departments, led Calzadilla to once again bet on herself.

Soon, Calzadilla started her own marketing company, the aforementioned Business 411, and immediately began offering her services to roofing contractors not only in Miami, but in the entire United States.

From there, she rented out an office space, and despite the onset of COVID-19 two months after she signed a lease, Business 411 has grown substantially as the demand for Calzadilla’s services has skyrocketed.

“We hired more people as our clientele base increased and also better organized our services,” she says of an acceleration process that has been far from smooth, but still rewarding as Calzadilla and her team have developed systems which allow them to properly service all their customers. 

“Going through those initial growing pains was crucial in getting us to where we are now.”

These days, as Business 411 continues to generate new business, more problem points have inevitably popped up, but Calzadilla has addressed those by spending what little free time she has investing in her professional education and reading as many business books as she can.

A more academic approach likely will serve her and Business 411 well, but there are some things an entrepreneur can’t learn from a book, as Calzadilla is readily finding out.

“There is an interesting dilemma that I see developing for us. This happens to any person or company who starts to achieve success, but right now opportunities are being presented that may not be right for our company,” Calzadilla explains.

“And what I’ve learned is that instead of letting other opportunities become a distraction, I focus on what I want to do as a business owner and entrepreneur.”

Namely, Calzadilla has now partnered with some of her most profitable clients at Business 411 in ways that go beyond creative branding and marketing strategies. 

Together with her husband, who is a financier, Calzadilla helps roofing companies buy real estate and other commercial properties so that these businesses can move closer toward creating passive streams of income.

And the entrepreneurial endeavors don’t end there.

Calzadilla has also started OnlyRoofers, a YouTube channel that strives to offer contractors an insight into the way different roofers run their businesses, all while remaining impartial to any internal or external influences.

“OnlyRoofers is about creating something in the industry that is unbiased. The channel isn’t about me sharing my opinion. People don’t really care about opinions, and that’s why the goal is to give people the opportunity to share their stories so that they can inspire others or receive inspiration,” Calzadilla details.

Ultimately, Calzadilla’s success can be attributed to many factors, but perhaps the most surprising one has been Calzadilla’s insistence on writing down her future goals and aspirations at every moment of the timeline, a decision that may have been just as impactful as any other strategy she has employed.

“Journaling is powerful. Actually taking the time to write out your own thoughts can be very motivating,” she says.

“For me, I look back on all the things I used to write about wanting to do, and I’m doing them now. It’s crazy, but I’m sure all the things I’m writing about right now will one day become part of my reality.” QS


Today’s post is sponsored by Business411!

A bit about Business411:

Elizabeth Calzadilla and her team help roofing contractors across the country increase their revenue and develop their businesses by offering specialized branding, marketing, and consultation services.

If you’re in the roofing and/or home service industry and are looking to level up your business, then click this link or scan the QR code below to get in touch with them today! 


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