Builders Series

The Co-Founder of Orchard Mile Shares How She Handles Investor Rejection, Manages Startup Hype and Deals With Doubt

Jennie Baik opens up about what she's built and the lessons she's learned along the way.
The Co-Founder of Orchard Mile Shares How She Handles Investor Rejection, Manages Startup Hype and Deals With Doubt
Image credit: First Gen Fashion
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Founder and CEO of Grayce & Co
7 min read
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Editor’s note: Builders Series features no-holds-barred in-depth interviews with female leaders in different industries to give you insight into what successful women have done to push through feeling stuck, frustrated and uncreative in order to build incredible brands and businesses.

Jennie Baik is the CEO and co-founder of Orchard Mile, a digital retail company that enables women to shop the full assortment of their favorite contemporary, luxury brands all in one place. She’s a next generation retail strategist, and it’s interesting to see how she moved from her role as head of strategy for Burberry Americas to running her own digital retail platform.

I loved the conversation I had with Baik about what she’s built and the lessons that she’s learned along the way.

Related: Refinery29's Co-Founder Discusses the Tough Women Who Inspired Her, Surviving Gunfire on the Job and Finding Strength in Vulnerability

What have you built, and what inspired you to build it?  

Orchard Mile is a digital shopping street representing the full collections of over 220 best-in-class designers’ sites. We also created “My Mile,” a way for consumers to curate their very own Madison Avenue based on their personal tastes. By selecting which brands you love (and product categories within those brands), we ensure the consumers receive real-time updates about new arrivals, sales and more from their own edit of the platform.

But above all, I have built a team of people that surround an idea with the right values. They have grit, and together we have created a culture at Orchard Mile that embodies next-gen corporate values.

Were you born a builder or did you have to learn to be one?

I have always been a builder, but in the past preferred to go it alone. My mom said I liked to take over the sandbox by myself. However, the biggest lesson in my career is that most of the time you can’t do it alone.  You need other people. Not only do they bring their talents, time and energy, but also they look out for your blind spots and push you to be a better builder, too.

Who was the first woman you looked up to, and why did you want to be like her?

Besides my mother, I really adored my third-grade English teacher. She would command a room of 30 kids and make us all sit cross-legged for a whole hour while she read from a book with no pictures and no sounds! (She didn’t even do the funny storytelling voices, which is usually table stakes when trying to get kids to focus.) I have always believed that if you can teach someone something, that is the most valuable use of your time, no matter what the payscale.  

What’s the greatest risk you’ve taken?

I like taking risks in my career. I’ve never been afraid of it, nor have I ever really done the pros and cons spreadsheet before making a move. For me, if it sounds kind of intellectually challenging and interesting, and if I think I can contribute in a unique way, the decision is already nearly made.

I always think the biggest risk you can take both personally and professionally is to be truly committed to an idea, or institution, in which there is no easy escape hatch. Whether it’s a startup that you’re bootstrapping or deciding to get married those are all “risky” endeavors in the sense that you might never be able to go back to the same starting place. But you start to realize that the things that stir that combination of passion and fear are probably the things that help you grow and feel most alive.

When have you broken down, personally or professionally? How did you break through?

Learning how to pick yourself up after being rejected is just a part of life. No matter how successful people are, everyone has been told ‘no’ and felt bad about it. And not all the areas of their life are perfect. I remember coming out of undergrad post 9/11, and it was hard to get an internship.  I got turned down by nearly every i-bank on the street, and ended up crying at an IHOP over pancakes in front of my dad. But then after knocking on a few more doors, I did eventually land one. Now, raising funds for a new company, I find that talking to venture capitalists is kind of a similar experience. Sometimes it’s just not a fit, but rather than taking it personally now -- of course, sometimes I do feel a little bad -- I just shrug and say, well, your loss, buddy. And let’s be honest, all this career drama really pales in comparison to real hardship in a deeply personal or health related way.

What makes you doubt yourself, and how do you manage it?

I think most entrepreneurs, despite the popular lore, do doubt themselves ALL the time. It’s hard not to, as some other person over there is raising more money, getting better partners etc., etc. You have to stop comparing yourself to stories that may not be true anyway. There’s a lot of over-positive fluff in startup land. As I’ve learned, the inside story may be very different. So when I have a down day and feel like I’m not going to get over it, I remember the last time I felt like that (probably like, a week ago) and remember how time and perspective can make things seems like a small drop in the bucket.  

How do you know when to leave someone or something?

When you personally stop learning or having anything to teach anyone else, it’s time to go.

Related: Jessica Alba on Being Brave, Dealing With Self-Doubt and Overcoming Major Breakdowns

When was your bravest moment? How do you practice being brave?

Bravery is all in context. I think my bravest moments are often in the toughest, lowest or most stressful moments, when you think your number is up and you have no more cards to play. I’ve stayed up nights wondering how I was going to pay my team, I’ve gone on stage to talk about Orchard Mile in front of thousands of people right after a deal fell apart and was told we would never make it, and I’ve kept my cool when disagreements have happened amongst our team. The continuous grit to keep going when things aren’t fun or aren’t easy defines bravery for me.

Knowing what you know now, was it worth it?

On a personal growth level, yes. In reality, there are lots of sacrifices that are made when you commit to anything. At a startup you have a real opportunity cost; you’re making a bet that this new thing you create will be better than a job you could find out in the market. But there is no truer test of one’s resilience than trying your hand at building something.

What can you see yourself building next?

Orchard Mile has been so all consuming in our first couple years that in the next few years I’d like to see myself investing more in my local community and balancing out professional passion and the need to win with a larger focus on how I can help or teach without expecting typical “market” rewards. As I’ve had this startup journey, I’ve realized that there is a different type of satisfaction to be had in giving without expecting much in return. And beyond my professional skillset, I’d like to learn more about what I have to contribute in other areas of my life as well.  

Related: Comedian and YouTube Star Grace Helbig Shares Why She Loves Tina Fey, Dealing With the Haters and When to Leave

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