Let’s get down to brass tacks here.
Who am I?
And how did I get here?
I am not a household name, and you may want some background info on me because, well, I’m giving you advice.
I lived twenty-four eventful years prior to launching Bulletin with Alana, and while my ten-year battle with chronic acne or brief stint as a horse lover may serve up some juicy entertainment, there is very little to learn from some drawn-out autobiography about my early life. And that’s kind of the point, here. I didn’t have parents plugged into the tech community, a well-connected group of founder friends, or financial resources at my fingertips. I never thought about entrepreneurship, launching a brand, or weaseling my way into Silicon Valley. I never joined a business club or got an MBA or even followed founders on social media. But business nestled its way into my lap, and into my life.
I had frantic entrepreneur parents that fled New York right after I was born because raising a baby in the city seemed literally impossible. They’d just started a small production company and, after nine months of carrying my stroller up a six-floor walkup, moved to LA, where they could, presumably, have a more steady, predictable life in the media and entertainment industry.
My family is (not super, but very) Jewish, and so they sent me to a religious day school for my entire life. I knew the same one-hundred-or-so classmates until I was eighteen. As I got older, if I wanted something, I had to buy it myself. I started working at the age of fifteen as a barista at a local bakery and did a whole camp-counselor-tutor-babysitter shuffle. My life in LA was very non-LA, or at least, not the LA reflected in Beverly Hills, 90210 or The Hills. When I tell people I’m from the sunny West Coast, I always have to add that no, I didn’t see celebs on the daily. And no, I didn’t go to any of the LA clubs or hot spots they’ve seen on Keeping Up with the Kardashians. I spent most of my Friday nights at Shabbat dinner or flopping around the house with my closest friends.
My parents were entrepreneurs, hustlers, hunter-gatherers. Some years were fruitful, and others weren’t so much. For the most part, though, my early years were very privileged and very steady. I always had a beautiful roof over my head, food on the table, clothes on my back, a great education, and woke up knowing how each day was going to go. My parents gave me the world and worked their asses off to build a business that supported our entire family.
We spent my later high school years struggling with my dad’s medical issues, our financial woes, and their marital tension. All three things converged into a giant, unruly tornado that threw our lifelong stability out of whack and turned every day into a suspenseful fourteen-hour slog for me and my younger brother. My parents struggled to make consistent money, we were drowning in hospital bills, and my brother and I were acutely aware that shit was hitting the fan. (Hi, Ben! I love you. We made it!) To make things significantly worse, because of our tight-knit community, our fall from grace was quite public. A lot of other people knew shit was hitting the fan, too. It was one of the most challenging, upsetting periods in my life. When it was time to go to college, I was eager to move very, very far away. I wanted to expand my worldview, meet new people, break out of my narrow day school bubble, and start living a life I could fully control. I got into the University of Pennsylvania off the waitlist, and I’m pretty sure I peed, cried, and booked my ticket to orientation that same day.
Outside of classes, I gorged on extracurriculars—a cappella, theater, sorority stuff—and was a work-study employee at a literary nonprofit on campus called the Kelly Writers House. The Writers House was a magical place. They had famous authors, journalists, and playwrights visit almost every day, and I helped run the readings and Q+As, which really meant I cut up baguettes and cheese and spent most of the night talking books with my brilliant co-workers and trying to steal sips of wine during the receptions.
Then, right before my sophomore year, my parents decided to divorce, their shared business finally fell apart, and it was up to me and my mom to cover tuition. To make sure I could graduate, I spent my summers working at restaurants, tutoring, teaching kids to sing, manning a boutique—literally anything to make some money. I eventually took on another part-time job during the school year writing copy at a local ad agency, where I got to dress up in my Urban Outfitters blazer and feel professional.
When graduation reared its head, I did what every Type-A freakazoid overachiever kid does: OCR, which stands for “on campus recruiting.” Despite my math and Excel anxiety, I applied to endless consulting, banking, and finance jobs. I just wanted money. A stable income. Financial security for the first time in a long time. I thought zero about my own strengths, skills, and pleasures, but I studied really hard and begged my Wharton friends to train me (insert a Rocky-style montage here). By the end of the first semester, I landed a job, which I would start after graduating. It was in asset management, which meant a 60K salary, benefits, and the envy of my employment-thirsty peers. At the time, I was making an average of $10 an hour and saving like a maniac. 60K a year would dramatically change my life.
Then, I quit. I quit before I even started. As May loomed, I started to think of my actual day-to-day in said asset-management role, and I kind of wanted to jump out a window. It just didn’t feel quite right, like being in an unhealthy relationship you know is doomed to end. I didn’t want to spend my days deep in Excel, dealing with numbers, building a career in financial services. I’m not knocking anyone who does this—it just didn’t seem fulfilling to me personally. It didn’t play to my strengths. I didn’t have a backup job, but I knew I’d be comfortable in a ton of other roles, whether working at a store again, finding another barista gig, bartending, or becoming a hostess— all jobs I’d happily done before. I was set on moving to New York and making it work no matter what. I called up the HR department and asked them to void my contract.
I met my first boss, Alison, at an a cappella reunion at University of Pennsylvania. She was forty, in the midst of a divorce, and needed an assistant. She worked in the marketing department at Condé Nast and without a job description, salary, or really even knowing her for more than five minutes, I said yes. I loved magazines. I grew up reading Vogue and Allure (and OK! magazine and Us Weekly and Life & Style, of course). When I was young, I used to cut up my mom’s old magazines and make new, original magazines with Elmer’s glue. I knew I’d be doing bitch work, but I figured I’d be doing it at the most prestigious magazine publisher in the world while working for a woman I admired. That, to me, was light-years better than faking my way through managing some rich guy’s money.
I worked at Condé for about a year, and yeah, I was totally right— I did a ton of bitch work. I had to supplement my abysmally low salary with babysitting on weeknights and weekends, so I was working seven days a week that whole year. I was a Hamptons au pair throughout my first summer, so I was there Friday nights through Sunday nights. And in the fall, I trekked from Astor Place to the Upper West Side, my Saturdays and Sundays lived on and off the 6 train. And because I was broke, I shared a bedroom with my boss’s seven-year-old daughter for six months. In exchange for free housing, I was an on-call babysitter and would help out around the house. I slept on a twin trundle bed beside Eden, her youngest, and commuted with Alison to work every morning. I know the privilege of going to a prestigious school with a strong alumni network afforded me this opportunity and others, but not every alum gives a fresh New Yorker a place to live and food to eat. I am forever indebted to Alison for making my New York life possible. Without her, I would not have been able to move to the city after graduating. My trajectory, and my entire professional life, would have looked very different had Alison not opened her home to me.
Thanks to Alison—for both the job and the free rent—my first year in New York was pretty magical. I was reading about three magazines a day and meeting tons of New Yorkers who’d “made it.” Sure, I was mostly making copies, getting coffee, and booking conference rooms, but I also sat in on every meeting I could. I shadowed older employees who I thought did interesting things, and I asked my bosses to give me mini research projects. Alison always obliged and gave me every feasible opportunity. I was exhausted, but I was home.
After a year, I hit a ceiling. Alison had left. I wanted to do more than my limited role required. It was clear that proactive projects weren’t necessarily welcome or expected, especially from an entry-level employee. No one in my department, aside from Alison, was going to give me interesting work. I was a department coordinator. That’s all they needed and wanted from me.
I like to say I was poached by a company called Contently because it just sounds so divine to be poached. But really, I did some very aggressive stalking and the LinkedIn equivalent of sliding into my soon-to-be new boss’s DMs. Elisa had come to the office to pitch Contently, and, from my desk, I heard the entire meeting go down. I knew instantly that I had to get in touch with her. Contently provided an editorial team on-demand. Meaning, if brands needed content—video, articles, infographics—Contently would vet and recruit the perfect freelancers to make it happen.
I hit up Elisa via a thoughtful LinkedIn message, and she responded that same day. By the end of the week, I had interviewed with the Contently founders, got poached, and had a new employment contract in hand. It was enough of a salary bump that I could finally stop working weekends. That’s all I needed to know.
My title was sales strategist, which sounded mega-fancy. But really, I was just helping my sales executive close deals with brands that needed quality content. My exec got let go within the year, and I was haphazardly tasked with filling the gap. As it turned out, I was damn good at sales. I was a smooth talker, sharp, and a little cheeky. But most important, I knew content better than most others on my team because of my time doing all that bitch work and squatting in meetings at Condé. I got promoted twice in a year’s time, was pulling in a six-figure salary, and making bank on my commission. I was able to help my mom pay for my brother’s college tuition and get her thoughtful gifts for her birthday. At twenty-four, I was proud of myself.
But the repetitive nature of my sales role eventually started to wear on me. I was having the same quasi-scripted pitch conversations every day, even telling the same stale joke at the start of every call. I loved that I was able to fuse together my content expertise and sales skills to make a ton of money, but when I got frank with myself, I didn’t want to sell writers to big brands. I wanted to be a writer.
And this is the part of the story where Alana changes my life…