Betting on Myself: How I Took the Leap to Start 1987
(& Tips If You’re Ready to Start Yours)
In 2019, I had just graduated from UC Berkeley’s top 10 MBA program. I had recently placed second in an accelerator competition and won funding to build an AI startup. Looking back, maybe I could’ve gone that route–Chat GPT and all that–but tech was never my true love. Fashion was calling, and I’m so glad I picked up.
In 2020, the world shut down: fundraising got strange, and as a female founder, the odds were stacked even higher–only 2% of all venture funding goes to women-led businesses. I decided I wanted to build something I could fully self-fund.
At the time, I was staying with my dad, fresh from a breakup, trying to figure out my next step. I pitched him the idea for 1987. He looked at me and said: “If you love it, go do it.”
So I did.
From Seaport to Something Bigger
I moved into Boston’s Seaport district and never looked back. Loungewear was just starting to really take off in 2020, partly because of the pandemic. Before then, it wasn’t as common to wear a hoodie around town and still look chic, let alone to brunch or to run errands.
I saw an opening–especially for women. Most hoodies on the market were unisex, boxy, and didn’t feel tailored. So our first product, the Back Bay hoodie, was designed to be cropped, refined, and flattering, while still being comfortable. It was our MVP (minimum viable product) and the thing that got people talking.
Then came TikTok. At that time, it was still in its early-adopter phase–meaning almost anyone could get views. We started hiding hoodies around Boston and making videos about it. It was playful, it was different, and it went viral. That’s when things really started moving.
Five Tips If You’re Thinking About Starting a Business
1. Get Clear on Your Idea
Have a business plan. Understand your total addressable market (TAM). You should be able to describe your idea in a couple of sentences–your “elevator pitch.” If you can’t explain it clearly and concisely, no one else will get it either.
2. Timing Is Everything
Ask yourself: is the market ready? Entering during a boom—like loungewear in 2020—can give you momentum, but you’ll face competition. Entering too early (like my undergrad UCLA friend who built an Uber Eats concept before Uber Eats even existed) can mean no one’s ready yet. Entering too late means you’ll need to radically change the game to stand out.
3. Start Small with an MVP
What’s the simplest version of your product or service you can launch to test the market (Minimal Viable Product or MVP)? This could be an email interest list, a single design, or a low-tech demo. Get it out fast, gather feedback, and see if it “flies” before investing heavily.
4. Understand Early vs. Late Adopter Advantage
Sometimes being first (Tesla, for example) is a huge win. Other times, coming in later but better can work too. Be honest about where you fall and adapt your approach accordingly.
5. Validate Before You Scale
Once you’ve tested your MVP, let the results guide you. If it takes off, double down. If not, refine or pivot your ideas.
The Biggest Lesson
Starting 1987 was a leap of faith–one that combined market timing, gut instinct, and a willingness to bet on myself. I didn’t always have every answer, I still don’t, but I began anyway. It’s all about preparing the best you can, and then learning as you go–learn by doing. The courage to start small–mixed with some good timing and clear ideas–can take you far.
Xoxo, Jen