What's Luck Got To Do With It?

On a scale of 1 to 5, how lucky are you?

This, I would learn at Project Entrepreneur, is Rent the Runway Jennifer Fleiss’ favorite interview question to ask candidates. And not because of some deep spiritual reason. But because she wants to know whether, faced with rejection and failure, you will be a glass-half-full or glass-half-empty kind of person. When it feels like you could hit rock bottom, do you trust your gut and continue to create opportunity, or just call it quits?

Moments before attending this conference, I was listening to NPR’s “How I Built This” podcast with Guy Raz during my morning run. I noted that almost all of his interviews ended with a final question: “How much of your success do you attribute to your skill, your intelligence, your hard work—and how much of it to luck?”

Each answer was pretty telling of the entrepreneur’s personality. One that resonated with me, from Instagram’s Kevin Systrom and Mike Krieger:

“I have this thesis that the world runs on luck; the question is what you do with it. Everyone gets lucky for some amount in their life and the question is are you alert enough to know you’re being lucky or you’re becoming lucky? Are you talented enough to take that advantage and run with it and do you have enough grit, do you have enough resilience to stay with it when it gets hard?”

As a Latina woman in business, I always rejected that the idea of “luck” played any role in my success. A McKinsey associate once told me, “I don’t think you realize how lucky you are to be a minority: If you perform as well as your male counterpart, you’ll get the promotion over him because The Firm values diversity”. Nah… Hard work was going to get me that promotion, not luck.

But as an entrepreneur, I’m beginning to embrace the meaning of luck on a different level. Yes, entrepreneurs want to know that their perseverance, preparation, and talent (things they can control) impact their success. But to some extent, entrepreneurs also have to feel lucky. It’s the illusion of luck that fuels the confidence needed to move mountains when all odds are against you, when you have to listen to a thousand no's before getting a single yes.

Thinking back on the past few months, I look at Pepper’s progress and feel extremely lucky! Here’s a quick update (I’ll let you decide if it’s due to luck or hard work ;) )

1.     We got accepted into NYU’s Summer Launchpad, a two-week intensive accelerator that trains students on Steve Blank’s Lean Startup methodologies, and won the Stern Venture Fellowship, an immersive summer program that offers incredible workshops, mentorship, and resources to advance our venture. We’ve had the opportunity to meet advisors from amazing startups like Zola, CourseHorse, and Birchbox.

2.     We were featured on MSNBC’s Your Business with JJ Ramberg. Being on TV was definitely a once in a lifetime experience! And the best news is that the judges loved our concept, awarding us a spot pitching at the BlogHer Conference in front of thousands of influencers.

3.     We received our first two term sheets, one from a micro-seed fund and another from an angel investor. After a lot of soul searching, we ended up walking away from the former offer because the terms weren’t right for us. (We were incredibly lucky to have had proper legal counsel). We took this as a huge learning experience that gave us clarity on what the ‘dream’ partner looks like for Pepper. This led us to form a long-lasting relationship with our first ever angel investor, someone who possesses not only the strategic thinking we need but who also showed passion, patience, and respect for our team.

4.     We’re working with (the best) sample-making fashion studio in New York to create our next style: a comfortable, well-fitting, and supportive wire-free bra designed with the small-chested frame in mind.

5.     We partnered with a handful of social media female influencers who are committed to advancing Pepper’s mission around body confidence and are helping us spread this movement.

Lia Winograd of Pepper