From Living In A Tent To 8-Figure Company

My father was my idol. He built a chain of twenty-seven women’s clothing stores from scratch. And when I say from scratch, I mean from nothing. This is the true tale of how one entrepreneur went from living in a tent to running an eight-figure company. 

The story starts out West. My mom and dad were happily living in California when my grandfather convinced my dad to pick everything up and move to the thriving metropolis of Millington, TN. This would have never happened had there been the internet in the ’70s because nobody willingly moves to Millington, but there wasn’t so the story continues.

A long and brutal trip

My parents tell their California friends bye, pack up all their possessions, and load up my two brothers for the trip across the country (I was still a year away from joining the world so I’m not a character in this story). This was no luxury trip because my parents had no money.

Imagine trekking across the country with a six-year-old and two-year-old in the middle of the summer. Now imagine eating nothing but Vienna Sausage and Spam. And finally, wrap your head around having to set up a ridiculously heavy (and suffocatingly hot) canvas tent every night instead of settling down in a nice cushy hotel bed.

It was a brutal relocation to say it kindly.

My parents finally made it to Millington running on fumes, but that’s not the end of their struggles. Remember, they had no money so they couldn’t just pull into town and post up in a hotel or rental. They spent two weeks camping in a park called Shelby Forest in the middle of July in that ridiculously hot canvas tent.

If you haven’t been to Memphis (Millington is a suburb) in July, let me reassure you that it’s hotter than Satan’s butt crack. My mom finally had enough. She took my two brothers and went back home to Louisiana to visit family and enjoy some running water. Her parting words to my dad,

“I’ll be back when we have a house.”

Now my dad is living alone in a tent in the middle of Shelby Forest. No money, no job, no family with him, and not exactly the brightest looking future. 

I can only imagine the doubt, anger, helplessness, and fear he must have been feeling. Describing him as desperate is an understatement. He had one shot to make it work so he pulled himself out of the tent and headed to the bank. Without a loan, he can’t move out of the tent, start a business, or bring his family back to be with him. 

Even though he smelled like sasquatch, the bank saw something in my dad. He and my grandfather were able to secure loans for $2,500 each, and that brings us to the founding of Holliday’s Fashions. 

Whatever it takes to survive 

Although Holliday’s eventually became a chain of women’s retail clothing stores, it started as a wholesale business. My dad would drive a Uhaul down to Baton Rouge to purchase inventory from a jobber. He’d bring the inventory back and put it in the warehouse in Millington. 

He then loaded up the family station wagon with samples and drove to mom and pop shops in small towns across Mississippi, Arkansas, and Missouri all week. He’d sling whatever he could and then come home for the weekend, restock, and head back out again on Monday. Some weeks were good and some weren’t. He just sucked it up and did what needed to be done to survive. 

This repeated for the first couple of years until my parents were finally able to convince a bank to give them an $80,000 line of credit. Getting access to capital was huge. Looking back, this was the turning point that eventually led to Holliday’s becoming a successful retail operation. 

The money allowed them to begin buying goods from the Dallas apparel market and stocking more inventory in the warehouse. Inventory meant they could open to the public in Millington once a month. Opening to the public once a month became once a week, and once a week became daily. Additional retail locations opened, buying moved to New York, and eventually, Holliday’s became strictly a retail business. 

The great Lee jeans debacle 

Growing the business was anything but a smooth ride. My favorite story is the great LEE jeans debacle of the ’80s. I’ll let my brother (Brad) share this story because he’s still scarred from it to this day…

“Dad got a huge wholesale shipment of LEE jeans when I was in fifth grade. This was the early ’80s so some people were wearing bell-bottoms, but everyone was wearing faded Levi’s. 

Because we had access to these jeans, I literally had a dozen pairs of dark blue straight-leg LEE jeans that I wore every day. I guess the good news was that they didn’t have holes, but mom would press them so they had a crease like slacks because that’s how dad liked them. 

It was not cool. 

All I wanted was a pair of faded Levi’s but every day I showed up in those dark blue jeans with large LEE letters embossed in leather on the back. 

By the time 6th grade rolled around my nickname was The LEE Rider because that was their ad campaign at the time. 

It was the bane of my existence.”

I feel for my brothers. They spent years sporting LEE jeans when they were anything but cool. I guess you could say the whole family made sacrifices. Here’s the original LEE jeans ad featuring yours truly…

LEE Jeans Ad

The entrepreneurial lessons to be learned

Holliday’s went on to become a chain of twenty-seven stores doing eight figures of business each year. Hundreds of people were employed and I still get notes to this day from former employees, vendors, and friends of my dad. This little company started from a tent had a massive impact on my life and the lives of countless other folks in Memphis. 

A few entrepreneurial lessons hit me as I revisited this story…

There are no shortcuts – My dad spent years driving around slinging goods door-to-door. There’s no better way to figure out what product will sell than being face-to-face with buyers. You can start hiring, training, and outsourcing to other people once you’ve done it yourself, but there’s no shortcut to becoming an expert at anything.

Dip your toe and then double down – Holliday’s started as a wholesale business. A one-time test of opening the warehouse to the public turned into an eight-figure retail business. Don’t be afraid to pivot if a test shows you a different direction, but don’t change direction without testing your assumptions first. 

Know your strengths – My dad wasn’t a trendsetter. He would have been the first one to tell you that he was really good at copying trends and fulfilling the demand for hot items at a good price. His competitive advantage was operations. Growing up as a scrappy wholesaler showed him how to spot needs and fulfill them faster and cheaper than anyone else. He leaned into this fact and owned it rather than trying to set the trends himself. 

Being an entrepreneur is hard and stressful. There are far easier ways to make a living. Only the select few embrace the hard work, sacrifices, and stress it takes to create something remarkable. I don’t say all of this to chase anyone off, I lay out these expectations so you know what you’re agreeing to when you start a company. 

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