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Managing the Emotional Rollercoaster of the Entrepreneurial Life — Vanessa Gabriel

When we are at our best, then we can contribute our best.

I had the opportunity to sit down with Vanessa Gabriel, Co-Founder of Drop Delivery. We discussed her backstory, the challenges and advantages of being an entrepreneur, and how she deals with the mistakes, stress, and work-life balance of the startup life. 

What’s your backstory prior to Drop Delivery?

My journey as an entrepreneur started ten years ago when I was a freshman in college. In 2011, flash sale sites like Gilt Groupe, Rue La La, and Hautelook were a shopper’s best friend when buying on a budget. None of those options quite fit my style as a young woman, and so I was inspired to create a flash sale site called aSociete right out of my dorm. 

With the mentorship of my dad, I gathered some friends, including Marc (Drop Delivery Co-Founder) and even my little sister, Jade (Drop Delivery Co-Founder) , to join my team. Before we knew it, we were attending the biggest fashion trade shows, signed the lease of a warehouse, and had a stock room full of inventory. We had tried everything under the sun from allowing customers to pay for orders in installments (think afterpay, but we called it flex-pay), working with influencers to create content, and creating shoppable lookbooks and videos. (How did Instagram barely make this a reality in 2018?)

I went for it! I applied to all the incubators/accelerators, participated in all the pitch events I could find, raised a friends & family round, and even applied to Forbes’ 30 Under 30 at the young age of 20. But after almost two years, we sadly called it quits as the business model was too hard to upkeep financially. I thought this company was going to be the one. It had been the most fun and hardest two years of my life. The lows of entrepreneurship didn’t seem so bad with your best friends by your side, but accepting the fate of failure was a scar on my heart.

Although embarrassed and ashamed for my first company being a failure, Jade and I knew we had something exceptional with our shoppable media. From that, our second company WNDRLUST was born. I believed in the idea so much that I dropped out of school to focus on it full time. 

We learned from aSociete that we didn’t want any overhead of inventory. So, WNDRLUST would strictly be an interactive shopping platform that allowed consumers to shop looks and engage with brand lookbooks and videos. While viewing or watching, you could shop for that outfit, follow that model on Instagram, or listen to that song on Spotify. All of this in 2014 and it still blows my mind that we were so ahead of our time! While we were building this, I was experiencing a huge change as I had just moved to New York City from a small California suburban town.

We had no funding, and I knew I had to make ends meet with a day job. During that time, surviving in NYC got the best of me, and unfortunately, WNDLRUST never even launched. 

Two companies and two back to back failures. It was a hard pill to swallow. 

For the next year or so, I worked odd jobs from being a personal assistant for a handbag designer, a receptionist at a PR firm, assisting someone in selling random items on Amazon, then running the US e-commerce department for a european beauty brand. Throughout that time, though, I was never truly happy and knew I wanted to be my own boss again with something to call my own. 

What inspired you to become an entrepreneur? 

Growing up, my parents had always encouraged me to follow my dreams, and that entrepreneurship was always a path I could and should explore. 

As young parents with two kids by the age of 20, they matured quickly and knew they needed stable and secure corporate jobs to provide for us. They crushed the young parents struggling stereotype and gave my sister and me an amazing childhood. As the story usually goes, they knew corporate life in Silicon Valley wasn’t forever, so they set out to be entrepreneurs. From a commercial development company, flooring, e-commerce to digital streaming — no idea was too big for them to tackle. 

I had the best role models and inspiration right in front of me. 

Business was always the talk around the dinner table. I have memories of helping my dad with his businesses, whether it was organizing payroll checks, handing out flyers, or visiting his job sites. I came to understand the world through a business lens, and from then on, I knew I wanted to own my own business someday — unsure of what that would eventually look like. 

What are some of the biggest challenges you’ve faced as an entrepreneurial team (or individual)?

Entrepreneurship is hard, and it always will be. It’s not a guaranteed paycheck every month. A quote that has always stuck with me is: 

Entrepreneurship is living a few years of your life like most people won’t so that you can spend the rest of your life like most people can’t.

It’s not so much the end destination with entrepreneurship but about the journey you embark upon. It’s so easy to get wrapped up in the day to day of running a business and when you look back at everything you’ve been through to get to this point is something to be truly proud of. 

Some of the biggest challenges early on included a lack of fundraising opportunities due to age, ethnicity, and gender. Scaling is also challenging to anticipate, but it’s necessary to grow your business, which is something you learn quickly. 

Working with different clients, you begin to realize that trust plays a huge role, and clients want to trust and rely on you for the services you provide. If we diminish that trust and reduce our reliability, then it will be significantly harder to gain it back. 

How do you maintain a work-life balance at a startup? 

We like to work hard and play hard. 

We make sure, as a team, that we spend quality time together outside of work — whether that’s a team happy hour, after work dinners, bonfires in the summer, hanging out on the roof of our office, etc. We know that when we’re strong as a team, we can help each other problem-solve to succeed and achieve our goals. 

We also know that time to recharge and reset is valuable. Everyone needs a break sometimes, and the team is always there to support that and do what they can to make sure things are still taken care of. When we are at our best, then we can contribute our best. 

What strategies or hobbies do you use for work-related stress management? 

I love making to-do lists and checking things off. If there are things I really need to focus on, I’ll prioritize what those are and classify them as my must-dos for the day. 

I recently adopted a dog, so he’s the perfect excuse to take quick breaks throughout the day to walk outside, get some fresh air, and give my mind a mental break. Lastly, work is always important no matter the time of day really, but when I am away, I try and really be present with whatever I’m doing and remind myself that it’s ok not to check your slack messages or email all the time. 

What are some of the common mistakes as an entrepreneur that you’ve learned to overcome via experience? 

Working remotely away from your team and normal office environment is hard! It takes a lot of discipline to stay focused amongst all the distractions and creature comforts of your own home. As easy as it is to just roll out of bed and work in your pajamas, sometimes that won’t lead to a very productive mindset and day. I’ve had to establish my own routine that works for me to keep me motivated and ready to attack every workday. 

If you have an important meeting and you have the freedom not to have anything scheduled at least 1 hour prior, then do that. You need to feel like your best self and go into that meeting feeling like a million dollars. If you have constant meetings up until that point, you won’t be giving yourself enough time to reset and recharge. There’s no worse feeling than going into a meeting and not feeling confident and prepared.

Finally, always follow up a day before for scheduled meetings to double confirm because sometimes people forget even if it’s on their calendar! Meetings should be straightforward and direct. Nobody wants to waste their time in a meeting. 

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