January 27, 2023

Nothing In My Size: Rashad Jackson from SlimTall | Episode 25 of Twist of Fate 

Nothing In My Size: Rashad Jackson from SlimTall | Episode 25 of Twist of Fate 

With so many clothing companies out there, it would be easy to think people of every size could find clothes for them. But while larger sizes certainly exist, the actual fit is far from ideal. Rashad Jackson started SlimTall because he was tired of searching for fashionable styles that made him look and feel good. He sat down and talked to host Douglas Younger III on Twist of Fate about how and why he started his own business. 

Trying It On 

Jackson is an athlete, engineer, and entrepreneur, and his personal drive and ambition are evident in every statement he makes. During the pandemic, he was left somewhat adrift. His degree wasn't much help, and he couldn't play arena football when everyone was in lockdown. He tried a few different career paths before he talked to his sister — who pushed him into what he really wanted to do. Coming from a family of big and tall people, he wanted to give kids what he never had: an easy and affordable way to get clothes that didn’t hang on them like a drape. 

While tall people tend to have an advantage in life, both in the personal and professional realms, they’re often ignored when it comes to fashion. The outliers will either need to buy custom clothes or improvise to make a certain item more fashionable. Douglas Younger III pointed out it’s a basic wish for people to feel good about what they’re wearing, no matter what kind of body shape they have. Like all of the best entrepreneurs in the world, Rashad Jackson of SlimTall is trying to solve a problem, and that problem isn’t ‘How can I get rich quickly?’ 

Nose to the Grindstone 

Rashad Jackson started with a bit of a leg up, thanks to a sister who already owned several businesses, but he still had to go through much of the learning process. Like many startup owners, he had to learn some lessons that challenged his assumptions. For instance, he assumed he had to stay away from credit cards, until he realized that credit cards do have their place. 

Younger opened up about his time as a teacher at Cal State, and how the personal finance section was by far the most engagement he had ever had from his students. For all that colleges teach, they don’t give students the practical information they need about personal finance. (It’s a shame when you consider how many people get hooked on the perpetual cycle of debt.) 

What Jackson ultimately learned trying to start SlimTall was the power of perseverance. He had to keep going back and back and back again before he was able to work it all out. He started with Wordpress before he went to Shopify. He talked to every tall person he could find. He had his relatives try on stuff and tell him their thoughts (spoiler alert: not all of the feedback was good). He went to the drawing board on how many items to order and how to best market them. 

The Definition of Winning 

Younger pressed him during the interview: he asked what did real success look like for Jackson? This is a key question for all entrepreneurs, particularly those who think only in terms of dollars and cents. Once you have the money, you're going to want something else to fuel you. Your definition of winning doesn’t have to look like anyone else’s, but it ultimately shouldn’t be about how much money you have in the bank. For Jackson, he didn’t want other kids to grow up the way he did: constantly searching for clothing that fit. 


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