Please, introduce yourself and your business.
My name is Tiffany, I’m 34 y/o and I am the Co-Founder & Creative Director of a NYC-based sustainable work bag brand called OLEADA.
How did you start your business?
Before founding OLEADA, I had a pretty extensive professional background. I didn’t go to design school, nor art school. I started my professional career as a trained engineer— more specifically Technology-related Strategy Consulting. In my late 20s, I then pursued my MBA in New York City, and landed a job in private equity.
After spending more than a few years in the industry, I realized there would be a glass ceiling above me as a female minority in a heavily male-dominated field.
The idea to quit my job and start a handbag brand really came from my background in finance: as a professional woman, it was so hard for me to find a handbag that fit my bulky work laptop, all my daily essentials, and still remain lightweight. More importantly, it was hard to find a bag that could easily be taken from day to night.
People told me I’d fail in this business because handbags are a very saturated item. But I thought to get creative, to see things differently: most handbags are just an accessory to your entire outfit, they aren’t seeking to solve problems for the people that wear them.
Bringing my engineering process into fashion design, coupled with design thinking methodologies I learned while working in tech projects, I was able to take charge of women’s fashion in a different way.
How much revenue was your best year? (include margin if possible)
We’re hitting our 4th year on the market. As of right now, we are at the multi-million dollar level globally.
When did you notice traction when building your business? The “Oh S**t!” moment, what did that feel like?
Because I’ve always been an investor, money has always been just a number to me. I’ve never had a concrete idea of how numbers and sales earnings really represent a company. At a multi-million dollar level, my brand’s operations are still so small, but they’re already very complicated.
My real “Oh sh*t!” moment was when I realized the companies I used to work with on Wall Street had revenues over $200 million.
Their boss’s and CEO’s looked so much different to me then compared to how I look at them now.
Although I consider myself a small fish to fry in a big market, I have to remember where I am is already considered “big” to those just starting out. I have thousands of consumers buying OLEADA handbags every year.
What was your childhood like? Were you slinging candy on the playground?
Despite the extroverted qualities I’m known to have today, I was actually extremely introverted as a kid. I would read a whole wall of books and delve deep into my school studies because my parents didn’t spend much time with me.
What has been your best marketing marketing channel?
We have several marketing channels because we are an online brand, and each market has us taking a different approach. But for the United States specifically, 40% of our sales is generated by organic traffic.
If there’s one thing I knew to do as Creative Director, I wanted a brand image that’s already anchored in people's minds: hence the term “work bag brand”. We make the distinction between a work bag and a handbag by showing one as an engineered essential and one as just an accessory.
Eventually, when people think about the term “work bag” I want them to immediately think of OLEADA, just like when you think about yoga pants, Lululemon pops into mind
Because I was once a woman in the corporate world, I always had a strong target audience and referral system within the corporate girl groups.
My number one rule of thumb is to not waste effort and limited resources by tapping into other markets. Focus on what you know, and what works.
If you’d like to know more about our global market (East Asia, UK, etc.) feel free to connect with me!
How many attempts at building something did you make before you found what you’re working on now? Did you always have an entrepreneurial drive?
OLEADA is my second attempt in entrepreneurship, and we’ve been on the market for almost 4 years now.
Before formulating something as complex as an accessories/fashion brand, I wanted to explore more about branding, marketing, and building a team. So my first business was a side hustle, as a Brand Consulting Agency, and I also co-founded a cosmetic e-commerce brand at the time.
I wouldn’t say I have an entrepreneurial drive as much as I live by the saying “live as your heart desires.”, I literally wear it on my sleeve (I tattooed it!) I am a person who pursues entrepreneurship because of the ultimate freedom it gives me: not financial (although finances play a huge role in accessibility), but for me, freedom means soul-free or mind-free. And only entrepreneurship can give me that.
It’s the ultimate life training for you to understand the world and people, to experience dynamics and challenges, and to live life to the absolute fullest. And eventually, you won't be bothered by any situation. You find peace at any time. That’s free.
What is your biggest overhead expense?
My biggest overhead is my content team, because OLEADA is a Direct-to-Consumer brand. We’re very driven towards making sales off of user generated content on all of our social media channels.
We also prefer to create all of our content in-house.
What’s the most important skill you’ve learned?
The most important skill I’ve learned is how to deliver information based on people’s personalities. I look to curate a staff that brings the workplace balance: some introverts, some extroverts, some in-between.
By knowing how to approach each of my staff members when it comes to delivering tasks, constructive criticisms, and/or praise, I am able to make my office run much more efficiently.
Eventually, people are the most important asset to build up a business. That’s why it’s called a company.
What do you spend the majority of your time doing, in a given week? (I think a lot of people hear entrepreneurs “work,” but may not understand what that means on a day-to-day basis.
I work almost 90-100 hours per week, dealing with the time difference in managing two offices in New York City and Hong Kong. My weekly schedule tends to look like this:
Monday-Wednesday: 8am - 12am meetings
Monday/Tuesday is for in-house operations— we discuss marketing plans and content strategies. Wednesday is for meetings with outside vendors / partnerships with agencies.
Thursday-Friday: I typically fill up my calendar with 1-2 industry events and/or networking socials. On these days my goal is to expand my network of contacts, so I usually schedule lunch/dinner appointments with people I’ve met at past events.
I also devote my office hours on product designs with my team these two days too.
Saturday: I block this time to spend with close friends and family. I also like to go out for music/dj related events. Music on, world off. (I might even do some DJ gigs in the future!) This is my day off and I do NOT think about work or return any work-related calls and emails unless it’s urgent.
Sunday: Depending on how much work I've done during the week, if there’s something urgent that I didn’t finish, I use this day to finish it before the new week starts.
If not, I use this day as extra leisure time or networking or personal development.
What do you know now that you wish you knew when first starting your business?
I’ll be real with you: there are so many mistakes you will make. My biggest mistake was spending too much of our marketing budget on product photoshoots. When I started I was heavily invested in the fashion industry and how they would shoot based on each season.
Then I learned that those that need to shoot for Spring/Summer and Fall/Winter are wholesale brands: they need to present products to retailers and in turn they have to spend money in March or in August before the seasons start.
Brands put effort in their lookbooks after all.
As a DTC brand, however, you are not just selling during that month—you’re selling year-round and you need to stand out and be relevant.
So now, I chopped my shooting budget to small amounts per month to push out more UGC to a targeted audience, in line with our own content marketing calendar.
Another thing I wish I knew was to be confident in having a different approach. Becoming a creative director and designer without a design background shifted my mindset— using engineering approaches to fashion design later became a huge differentiator for us. I put logistics first: function over form.
After all, there are already so many cute and lovely bags on the market, but they’re not convertible. They’re not light weight. They’re not meant to hold a laptop.
I used to doubt myself and my capabilities. Now, I know you can use what you lack to create something new, something unique & special to you and your brand.
The world of entrepreneurship can be misleading. Many people think it’s always easy and always glamorous. What’s a big problem you’ve faced as a business owner and what were the emotions behind it?
It’s never easy. I’m working so hard to live this life!
Most of the time I feel responsible knowing how many of my staff members' lives depend on me and my performance within this company. Naturally, I would never tell them this out loud, because as an entrepreneur you always have to remain positive and secure in your capabilities. A good leader protects her team.
The way you act and the way you hold yourself will be imitated by those that work for you. If you remain strong, they’ll see you as an impenetrable security net, and focus their efforts on their work, not their anxiety of job stability.
But I think it goes without saying— the daily stress-levels of entrepreneurship cannot be taken by everybody. But entrepreneurship is about taking calculable risks, and knowing how many risks you can take, how big your business has the potential to be.
And seriously—You can’t put your stress or negative emotions into your work. You can’t snap, and shouldn’t avoid it. It just creates a malicious cycle.
On social media every entrepreneur is showing the best side of their lives. There's an illusion for the audience. Sure, I go out to parties, I wear nice clothes, have nice dinners, but they do not see the effort behind the lifestyle.
I have about 100 emails and text messages to sift through every morning with the time difference between NYC and HK. I get 5 hours of sleep a night during weekdays. You only see 10% leisure, and not the 90% effort and tireless work entrepreneurs put in.
Many people don’t know where to start in the business world, they feel stuck. They may want to start a business to become their own boss and create their hours. What is your best advice for someone who feels completely stuck?
My best piece of advice is not to start a business that is completely irrelevant to you, and to your lifestyle. You can’t hope to one day become something you’re not for the sake of business. Find a commonality between what you like, and what you’re good at, and that’s your idea.
Yes you need basic necessities like ambition and skillset, but then you have to think about resources: who can help you in your current network, what money do you have or have to earn from investors, and when you have to build your team.
Entrepreneurship is a constant trial-and-error process. There is no recipe for you to follow and immediately be successful.
