Meet Jess Davidoff, serial entrepreneur and CEO of STATE Bags, a Brooklyn-based accessories company that employs a 1:1 give-back model, donating to children and families in need with every bag purchased.
Jess joined the STATE team as a CEO last year, after working with them as an advisor through her consulting company, Sprezzatura, which does strategic advisory for direct-to-consumer startups and small businesses. Prior to joining the STATE Bags team, Jess started a number of businesses throughout her twenties and continues to thrive in her every endeavor.
We chatted with Jess about making the transition to CEO, starting her first company at 22, and having confidence in business as a female entrepreneur.
THIS INTERVIEW HAS BEEN EDITED AND CONDENSED FOR BREVITY AND CLARITY.
So to start, tell me more about STATE Bags and what made you interested in joining the team.
“I loved everything about STATE [Bags]. I was consulting for them for about a year and a half, and what was so special about the company was the fact that they were able to combine these really really high quality, fashion-forward, and functional backpacks that could resonate with so many different types of people but also stay true to the core of the company’s mission which was to give back. And I just absolutely love the inspiration for founding STATE that Scot and Jacq had, which was witnessing children coming to their charity’s camp carrying their belongings in plastic bags and shopping bags. I love the origin story of the company and I saw a lot of potential for growth and thought that I could really lend the business hat to their project”
So what does a typical day look like for you as CEO?
“I would say there is no typical day. We’re making so many changes to the company right now. When I started with the company in May, the big push was putting together a really really solid three-year plan for the company and then it was determining who we needed on our team to really execute that plan so in the early days of when I started, it was really all about putting together the ideal team to execute on the vision and now we have the most incredible team ever. I’m so excited about everyone on the team. Now it’s really about focus on hitting our monthly targets and really motivating the team to grow, especially our e-commerce side of the business and so I’m playing a huge role in the digital marketing side, and the brand’s online persona, and the way that we’re storytelling through social and through our emails.”
What did your role look like as a consultant and advisor before you became CEO?
“I was really wearing the CFO/COO hat, so looking through what the big goals of the company were, creating the proper financial projections, then building out models, and looking through the different metrics each month as well as the KPIs to determine where the different drivers were that were helping the company drive the most growth and I was advising the founders and the then-CEO on different initiatives that they were thinking through and being a thought partner so that when something arose, they could bounce ideas off of me.
What big projects do you have planned for STATE in 2019?
“2019 is definitely a year where, from a product perspective, the bags that we’re creating, we’re definitely elevating the collection. We’re introducing a lot of leathers and a lot of fun small accessories into the line like belt bags or fanny packs and so I’m really excited about this collection. And this is also a big year for partnerships for us. We have a big partnership launching with American Airlines this month. We’re doing collaborations with the Moxy Hotel in March. And then in the fall, we’re launching partnerships with a bunch of different organizations so this is really solidifying our partnerships and doubling down on e-commerce.”
You’re a serial entrepreneur—tell me more about your past endeavors and your background.
“I started my first company when I was 22. It was a year after I graduated from college. I did not have a business degree. I majored in public policy so I really didn’t know anything about starting a business. My first job after I graduated was as a director at an SAT prep company and it was the year that the SAT changed so I hypothesized that a lot of students might opt to take the ACT as a backup. And I proposed to the president of the company that I wanted to write ACT prep curriculum and he thought I was crazy and said nobody in New York would ever take the ACT. So I just quit on the spot, called my dad, told him—he thought I was kidding but I wasn’t—and I said I needed to borrow $3500 because I needed a website, I needed a logo, and I needed business cards. So I spent six months writing ACT prep curriculum and then launched my business, and lo and behold a lot of kids wanted to take the ACT so we kind of blew up overnight. I ended up hiring about 22 tutors that first year and it really took off and that grew really rapidly. But it was in the services industry and we were always providing very customized, high-end one-on-one tutoring and admissions counseling. And then around 2011/2012 I got really enamored with the power of technology in education. That’s when I decided to start my prepping company Admittedly, which would allow me to distribute the types of curriculum I had developed from my first business The Edge to millions of students for free via website and our mobile app so I founded Admittedly in 2013. My first loan, which was just a loan from the parents, and then totally bootstrapped. For Admittedly, I raised about two million dollars in venture funding and we grew really really fast then we were acquired in 2016. The company that bought us changed the name to myOptions and now there are about six million kids using the platform still today which is really awesome and exciting. After that, I started a consulting company called Sprezzatura. It’s Italian for the meticulous planning that goes into making something effortless and we were doing tons of consulting for small businesses and startups, mainly in the direct-to-consumer e-commerce space. And STATE was one of my clients and the goal of Sprezzatura was to really help companies put together this detailed plan that allow them to have sustainable but aggressive growth. So that’s really what I was really working on for STATE and the opportunity arose to come onboard as an interim CEO. It was such a great fit that I ended up staying full-time as their CEO, and I had a baby in September so I thought it was gonna be super interim, but it was the perfect fit and I’m very excited about being here.”
What’s the biggest obstacle you’ve had to overcome in your career?
“I would say the biggest obstacle for me was—because I started out as such a young CEO when I was 22—it was always making sure that I really just trusted my instincts. When I first started out, I definitely was influenced a bit by people who were more seasoned and had walked down certain paths. Like for marketing campaigns by really really seasoned marketing professionals, that really didn’t feel right in my gut, but I was like “Oh, I’m only 22, I don’t know what’s right or wrong and they sound really smart and they’ve done this so I’m going to do it, even though I deep down knew that it was the wrong fit for my company. So I think growing as a CEO, it was really just trusting my gut even though I didn’t really have much experience outside of just running my own business. And now, 15 years in, I think I’m sort of there.”
What was one external factor that you feel played a role in your success?
“I would say [an] external factor would be the kind of people I surrounded myself by. One of my biggest go-to resources has been the Princeton alumni network. They have the most incredible alumni community. And I’m the type of person who’s not afraid to ask questions, and I feel like I’ve sent thousands of emails and have gotten just the most incredible responses from people who were willing to take 30-minute phone calls for free just to help me out with situations where they had “been there, done that” before so that has been truly truly helpful. And then I’d definitely say my family and my husband have been super super supportive of me being an extreme risk taker in my career and jumping off of cliffs and figuring out how to build a parachute on the way down. I think for anyone being entrepreneurial, it’s really all about surrounding yourself with people who help give you that confidence on the days where you’ve heard “no” 70 times from VCs because entrepreneurship is just a roller coaster. I oftentimes equate entrepreneurship with surfing because I would say I’m the worst surfer in Montauk, which is where I go every summer. Literally when you’re an entrepreneur, it’s like when you’re a bad surfer, you’re going out and you keep getting pummeled with waves and you’re wiping out basically all day, but for some reason you just keep going out there even though you keep getting destroyed by waves because that one good wave, it’s just like oh! The day was magical. And that’s entrepreneurship, it’s 90 percent of the time. You’re literally getting pummeled by waves, but on those days where you get a really great wave, it’s the best thing ever. And I think that having supportive people around you—family members or friends—is just super super important because you can get really beaten down by just all of the forces.”
What advice do you have for women looking to seek venture capital?
“I would say know your numbers. I’ve seen it a lot, in terms of some of the companies I mentor or some of the companies I was advising. Women in particular—maybe it’s because they heard throughout their educational journeys that they’re not good at math, but going into a VC meeting and just saying “oh I’m not good at math but I can get back to you”—that’s not going to build confidence in the VC so whether it’s meeting with someone and paying someone to really teach you what numbers on a financial statement mean, but knowing those numbers and understanding how you got them is super super important. I’ve made several angel investments and I have to tell you, it’s really really refreshing when somebody can come and really talk through the numbers and it’s really apparent when you outsource getting someone to do your financial statements, and that’s totally fine. It’s not like every entrepreneur needs to be able to build a three to five year financial plan, but it is incredible to be able to talk through it and understand it so I think that would be a big piece of advice is to get yourself to a point where you’re confident with the numbers and make sure that the person who created your plan takes the time to really sit down with you and educate you on what the numbers mean and how they arrived at them.”
What advice do you have for young entrepreneurs in general who are just looking to build and grow something?
“I would definitely say the biggest and most important element of being an entrepreneur is self-confidence. Whatever it is that gets you personally amped up and confident in yourself, do that every morning. For me, I like to listen to rap music. That gets me really pumped up. Literally every morning in the shower, that’s what I’m listening to. That’s what I’m listening to in my headphones walking to the subway because it gets me into a certain mindset of confidence. So even if it’s looking at yourself in the mirror and saying something. Anything that you can do to make you believe in yourself. I think Kanye West even says he has this massive portrait of himself in his living room and someone asked him, that’s a pretty aggressive, narcissistic thing to have over your mantle—why would you have a portrait of yourself? He’s like, “you know, if I’m not gonna cheer for myself first, nobody’s gonna cheer for me.” And it sounds condescending or overconfident, but that’s how you have to be if you’re gonna be an entrepreneur because so many people will think you’re crazy going to think that your idea is bad or it’s never gonna work, and it might not work, but you are gonna be the person who will make it work because you’re not gonna give up and it all starts from you being really really confident. Just say whatever it takes. And then if you are actually going out to raise VC funding, I tell everyone who I meet who has asked for advice, look in the mirror and say with a very straight, super confident face, “my business will be a billion dollar business.” Full stop, period. No “eh” or “maybe”. Be able to say that with confidence and that will be hugely impactful for the meetings with VCs if they see that you believe that fact first.”