When Jennie Baik and Morty Singer first met, it was to discuss the future of a business idea they, and a handful of other entrepreneurs, were working on: Orchard Mile, a customizable digital shopping mall for the internet age. As the company (and Singer and Baik’s working relationship) solidified, Baik assumed the role of Orchard Mile CEO while Singer stepped in as chairman and close advisor to the team. (Singer is also CEO of TRAUB consulting firm.) Despite some initial skepticism, the CEO now looks to her co-founder as a valuable mentor, sounding board, and friend.
Women Entrepreneur: How did you two first met?
Morty Singer: I think we’re currently sitting at the very table where we met.
Jennie Baik: We were introduced through a mutual co-founder of Orchard Mile, and the first time we met, we had a long conversation about the future of retail. Morty is the chairman of Orchard Mile, but he also incubated us through his company, Marvin Traub Associates. So he’s technically a co-founder but also is our eyes and ears to the industry. At the beginning of our meeting, I remember saying, “Morty seems so busy, does he actually have time for this?” You know how some advisors are advisors in name but don’t really do that much? I was skeptical. But I was quite wrong. Our relationship is the one in which I’ve been the most surprised and grateful.
WE: How has it evolved over the years?
JB: At first it was quite tentative. He has his own clients and things to take care of. Morty’s family is made of very strong women — I’ve met his mother, his wife is a big deal at YouTube and he’s got two young daughters. He’s always been a champion of women, and hearing him speak about his own family helped me get comfortable and made me realize that there was the potential for him to really be on our side. He’s a great cheerleader, and he helps cut down on things I’ve found difficult. I can be very defensive and tend to act like everything is under control. Morty has the ability to say, Is it under control, really? He gives direct feedback.
MS: But I oftentimes feel like Jennie doesn’t really need me, she might just need a whisper on something. She’s juggling 20 balls at any moment. We joke that for the first two years of Orchard Mile, the last person I spoke to before I went to bed was not my wife, but Jennie. My wife would even say, at night, “Have you had your Jennie call?” But we’d do a data dump and make sure we could tackle the next day. As the team has grown, and we’ve all grown, there’s less need for daily consoling. But as the company grows, the question marks get bigger.
JB: With entrepreneurs it can be easy to get so in the weeds that you miss the trees. So in the beginning it was like, what should I do? And now it’s about, how should I do these things? I incorporate some of the vision that he naturally has. It’s funny, before Orchard Mile, I worked in strategy and thought execution was easy. But now that I’m in the execution part, I really need help with strategy!
MS: I’m a huge believer in 360 listening and learning. While this interview is set up as me being the mentor, if you take an approach of 360 listening and learning, you end up being the mentee as well. Everyone has to learn continually, otherwise you get left behind. I have a view on the industry and financing and capital markets, which Jennie values and welcomes. But her ability to understand the intricacies of digital marketing? I’d be crazy to not believe she’s my mentor in that respect. You’re never too old or young to learn, and you can learn from anybody and everybody.
WE: What are some specific ways you two have changed the way you work?
MS: I’m an over-communicator, and I think I’ve pressed Jennie to communicate for the sake of communicating. Even if you don’t have the answers, people want to hear from you and know you’re thinking about them.
JB: I still work on that. Morty says over and over, investors hate surprises, whether good or bad. Communicating all the time is something I’ve learned. And in terms of mentorship, Morty has really changed how I think about working with my mentees. Morty doesn’t delegate the hard stuff, the tough, emotionally charged stuff. He’s there. I’ve had other mentors in the past and they were happy to advise you at 3 p.m., but at 11 p.m., they’re nowhere to be found.
WE: Jennie, how actively are you positioning yourself as a mentor to other people in your industry?
JB: I think of every person on my team as a mentee. If we’re not mentoring them, we’re not doing our job. We should teach them ways to think rather than what to think. I’ve learned from Morty the importance of meeting people. I used to think it was most important to get work done. But networking isn’t about having cocktails, it’s about learning what’s happening in the market. People tell you things, not the internet.
MS: I can’t take credit for that, unfortunately. I learned that from probably the greatest communicator, the late Marvin Traub, who’d famously take three breakfasts and two lunches. It was a curiosity and a thirst for information.
WE: Other than help with the business, how important is having emotional support as you get a company off the ground and work to scale it?
JB: If you would have asked me four years ago if I ever needed emotional support, I would have said absolutely not. But it’s the most important thing you can have. Feeling okay affects your work. You need people to tell you sometimes that maybe this one thing isn’t a big deal. And I’m working to divorce myself from always trusting the data. Businesses are about people, which I often forget. But people have emotions that can drive decisions, and measuring those emotions is valuable — but you have to make sure it’s not just the loudest voice steering the ship.