How to build a game-changing tech app: five tips from Jessica Wilson

A Leader in Heels is a self-starter. Someone who dares to dream, and creates her own opportunities.

Jessica Wilson, founder of the fashion app Stashd, is a true example of a Leader in Heels. After being told by a careers counselor that she couldn’t make it in the cutthroat fashion industry, Jessica did more than prove her doubters wrong.

A quick note from LH Agenda…
Did you know our award-winning planners and journals are designed in collaboration with industry experts? They feature mindset, productivity and leadership content to inspire and empower you.

LH Agenda LH Planner

After a successful stint in fashion working in Australia and New York, Jessica was drawn to Silicon Valley to learn more about the tech industry. With her trademark determination, she wanted to learn how she could use her fashion industry knowledge to create her own space in an entirely different (and competitive!) industry.

Stashd is a “fashion discovery app”, which helps you discover and buy your next favourite piece. The app presents a single item at a time: if you love it simply swipe right to “Stash” it into your virtual wardrobe, or if its not for you, swipe left to “Trash” it. Your virtual wardrobe can be shared with friends, and also helps you purchase your favourite pieces directly from the store!

So how did this Gen Y leader go from a career in fashion to being a tech co-founder? Jessica chatted with Leaders in Heels to share her five tips on creating your dream company from scratch.

1. Look for ways to make your own experience

Jessica’s entrepreneurial drive was evident in her teens. After being told that her high school wasn’t having a formal after-party, at the age of 16 Jessica learned that “when someone says you can’t do something, it doesn’t actually mean that you can’t do it”.

Jessica took matters into her own hands and negotiated with her parents to have the party on their farm. This experience, from learning how to negotiate with her parents, DJs and suppliers, through to running events attended by more than 400 people, gave Jessica important leadership skills and the understanding that you can make your own opportunities out of nothing.

2. Take set-backs in your stride and always follow your gut

After her success in running events, Jessica was more than ready to take the next step into fashion. After researching a lot of schools, she found what she thought was “the best of the best”. However, things didn’t turn out as planned when she was told that she didn’t have what it takes to have a career in fashion.

A quick note from LH Agenda…
Are you tired of unproductive meetings? Let our Meeting Notebook help make your meetings work.
LH agenda Meeting Notebooks

There’s no doubt that this was a really difficult time for Jessica. After a period of self-reflection, she knew that it was time to leave.

“I decided to not take their perception of me to heart. They didn’t know me, and they had only met me for a few minutes. It was a matter of backing myself, trusting myself and hoping it would all turn out. They weren’t supporting me and what I wanted to do, so I had to leave.”

For Jessica, this was another important lesson early in her journey: trust your gut and never settle for second best.

3. Throw yourself outside your comfort zone

After the early set back, Jessica’s determination landed her a job doing seating charts for well-known designers such as Akira Isogawa and Bettina Liano. This was a huge learning curve, and it wasn’t long before Jessica was off to New York, producing shows for Australian designers before working with industry heavy weight Kelly Cutrone at People’s Revolution.

At this time, Jessica noticed “dots in the industry that started to connect”. After deciding she wanted to learn more about the tech industry, she immediately headed to Silicon Valley. At 21 years old, Jessica threw herself out of her comfort zone and spent a week heading to different events, meeting people from Google and Yahoo, who heard about her journey and took her around tech giants such as Google, Facebook, Yahoo and Apple. After learning everything she could in a week, Jessica knew that fashion technology is exactly where she wanted to be.

4. Look for people with skills that compliment yours

One of Jessica’s greatest skills is throwing herself into meeting and learning from people with the complimentary skills to her own. After returning from Silicon Valley, Jessica went straight to a tech co-working space, and surrounded herself with the people that had the skills she needed to create Stashd.

“If you have a genuine connection with someone, it will open more doors. You need to just put yourself out there”

5. Beware of “founders’ bipolar”

Jessica admits that life as a founder is not just the perks you see in the media. After living and breathing Stashd, she recognised the importance of looking after herself to ensure that she can make it through the good and bad times.

“You need to learn how to manage your state, how you are going to take on all of these challenges and how you will cope mentally.”

These days Jessica uses meditation to help stay grounded, and get her through the busy days and often long hours involved creating a game-changing app.


Thank you to Jessica for taking the time to chat and share her advice with Leaders in Heels. After a huge few months, which have included being the youngest Australian woman ever invited to attend the Forbes Under 30 Summit, and heading to Antarctica with a group of fellow entrepreneurs, we can’t wait to see what’s next for Jessica and her tech dream.

One reply on “How to build a game-changing tech app: five tips from Jessica Wilson

  • Brian

    Great insight and excellent overview. I like number 4 the most. The right people around you is a must especially in this IT world we now live in.

Comments are closed.