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The clothing subscription service built just for petites

July 24, 2022, 11:00 AM UTC
Isabella Sun, CEO of Short Story
Courtesy of Short Story

Clothing rental and subscription services—especially those around work and formal events—took a hit during the pandemic given there weren’t many events that called for anything beyond t-shirts, jeans, and sweatpants for awhile.

But returning to the office and the revival of parties and wedding season has many people developing minor anxiety about a trivial but still basic necessity: what to wear. That can be extra problematic for consumers who have trouble finding many options in their size.

Short Story launched last year as a new direct-to-consumer retailer with a clothing subscription service just for petites (women 5′ 4″ and under). The startup’s proprietary fit technology is touted to pinpoint a better fit for customers, leading to less surplus. Through the brand’s preliminary style quiz, customers can inform their personal stylists curate a selection of clothing perfectly suited for specific wants and needs.

Founder and CEO Isabella Sun recently shared more with Fortune about launching a clothing brand during the pandemic.

The following interview has been condensed and lightly edited for clarity.

Can you share a bit about your professional background prior to launching Short Story?

I grew up in a family of entrepreneurs, so I’ve always wanted to start a business someday. I began my career at Bank of America Merill Lynch on the Global Expansion team helping the bank expand into Latin America and Asia. Then I pivoted into sales and trading, where I structured financing deals for private equity firms and large corporations. As a 20-year-old, I was working on multibillion-dollar deals with others with much more experience, so it was a total eye-opener. It was fascinating to see how capital gets deployed to jumpstart and scale businesses.

While I’m numbers-driven, I also loved graphic design and the idea of storytelling through visual branding. I had an interest in manufacturing and read a lot about the fashion industry. It moves at lightning speed and every detail is significant. My uncle was a tailor, so at a young age I got to see garments being designed, cut, and sewn. That fascinated me, and I thought maybe one day I’d get to try my hand in fashion.

What inspired you to launch Short Story?

Two things inspired me to start Short Story. First, growing up, I saw my mom triple-tasking as a single mom running a business, getting an MBA, and raising a kid. She was really busy and had no time to shop, so she always wore the same gray sweatpants, and I so badly wanted to give her a wardrobe makeover. I wanted her to look and feel incredible. When I started my career in banking, which is known for having insane hours, I was trying to get more sleep while still looking polished at work. Many of my female coworkers were on the hunt for elevated work clothes and going through the ordeal of getting everything tailored. That one blazer or dress that you can just slip into, with no alterations or custom tailoring, just felt so elusive. I realized that there are many female professionals, parents, etc. who wanted to look put together, but they didn’t have the time or mental space. I felt like there was a need there calling for a solution that would help them feel 200%, all the time.

The other interesting thing that I’ve observed as a petite woman specifically is that for women of shorter stature, shopping can really be a really demoralizing experience. Most clothing sold is designed for women who are 5’5” or taller, and often fitted on 5’9” fit models. After years of altering my clothing or passing on certain styles altogether, I was very surprised to discover that nearly 50% of women in the U.S. were considered petite, which just means 5’4” and under (and all sizes, not just small). They were having the same frustrating experiences.

More shockingly, less than 4% of clothing is made for petite proportions. Fashion has not been inclusive for petites. I wanted to create beautifully fitting petite garments, and then help petite women dress with confidence. I wanted to create a seamless experience where perfectly curated outfits arrived at your door. The industry was in need of alterations, and I was tired of waiting for this to happen. I decided to build it, and Short Story was born.

Through the brand’s preliminary style quiz, customers can inform personal stylists, who curate selections of clothing that are better suited for their specific wants and needs.
Courtesy of Short Story

As anyone who has shopped for clothing online knows, it can be difficult to navigate size charts, even with personal measurements on hand. Can you share more about Short Story’s fit technology and styling quiz, and how customers can put those to use?

Our entire business model is premised on building a rapid and iterative learning machine in which we’re learning a ton from our customers in a short amount of time, and doing that over and over again. This allows us to create ultra well fitting garments that are perfectly matched to their proportions.
When our customers first sign up on the site, we direct them to a preliminary survey which allows us to better understand their personal fit struggles and wants, styling preferences, etc.

My cofounder, Samuel Hoffstaetter, who previously worked on self-driving cars at Google, heads up engineering at Short Story. He had done tons of interesting work around machine learning and computer vision previously, and the two of us saw the opportunity to revolutionize fit in the same way. We built an internal system that leverages the anecdotal and quantitative data, including bust, hip, inseam, waist, height and weight measurements to create expertly fitting clothes. We know that consumer preference-based returns (e.g., fit) drive around 72% of all returns in fashion product categories, so we knew fit was critical. Sizing is wildly different across brands, so shoppers resort to things like bracketing (buying the same dress in three different sizes because you have no idea if it’ll fit you, and then returning two). We’re removing the need for customers to read size charts, period.

On the backend, we use this data to create products in continuous rapid iterations where each version of a product becomes better than its predecessor. Our customers drive all of our sizing and product decisions. While typically fashion brands traditionally only use two to five fit models to inform the dimensions and silhouettes for their full sizing range, we design our clothing based on feedback from over 100,000 petite women.

One of the many insights this data has revealed is that the many petite women have a more straight body shape vs. the hourglass shape that fit models typically possess. We’ve launched over 10 private label brands to date based on our learnings from customers that we sell exclusively through Short Story. We’re continuing to expand our private labels using a learning model that allows us to be 12 to 16 times more reactive than traditional retail.

Short Story says its proprietary fit technology allows the company to pinpoint a better fit for its customers, leading to less surplus.
Courtesy of Short Story

How is the company funded? Is it self-funded or have you reached out to investors? What has the financing process been like?

We’ve raised $3 million in seed funding from institutional investors like Tribe Capital, True Global, and Y Combinator, and also brought on incredible angel investors like Adrian Mcdermott (CTO of Zendesk), Eric Richmond (director of engineering, pricing at Shopify), Nate Lew (founder of OpenFan), Katie Soo (CMO of KiwiCo), and many others onboard with us throughout this journey.

We saw all the signs of product market fit in our data, and have grown our team by 42 times over since founding in 2019. We’re continuing to aggressively hire in engineering, marketing, merchandising, and operations. Our revenue has grown 95 times since the pandemic to what is now a business with an eight figure annual revenue. We’re considering doing a Series A next. I’m proud that we’ve been able to build a business that has not only grown tremendously but also done it in a capital efficient way. Coming from a finance background has certainly helped us nail unit economics from day one.

Looking forward over the next five years, how do you want to grow Short Story?

I want Short Story to continue creating beautiful products that women actually want. My goal is to remain focused on building our community and continue to grow Short Story in an authentic way where we’re really listening to her pain points and needs. We have this unique opportunity to flip the traditional design-manufacture-retail model upside down and instead let her drive all product and design decisions. I want her to have a diverse product experience, so at some point we may build an Etsy-like marketplace where we incubate new brands and they can flourish with access to our customer base, insights, and tools.

I also hope to move the fashion industry forward. We’re working on lots of projects internally to modernize the way clothing is designed and merchandised. Apparel is a $140 billion industry, and a lot of it sits on ancient tech. Fit is the biggest pain point for everybody–customers, clothing brands, and retailers. Fit is intensely personal. We’re solving this very complex problem for petite women and eventually for everybody. Many of the problems we’re solving are applicable across demographics and the internal tools we’ve developed can address some of these challenges for every brand and retailer.

This is an installment of Startup Year One, a special series of interviews with founders about the major lessons they have learned in the immediate aftermath of their businesses’ first year of operation.