How I Turned My Side Hustle Into A Million-Dollar Business

If you told me three years ago that the small publication I started with a work friend would grow into a company with 13 employees, two physical stores, and $2.2 million in venture funding, I would have rolled my eyes. Bulletin, our colossal effort to revolutionize retail, began as a fun side project in winter of 2015. I was 23 and worked with my co-founder, Alana, at the NYC startup Contently. We were both on the sales team and were helping big brands create editorial content. After a year or so at the company, we started toying around with the idea of building our very own digital magazine for cool, indie brands. What started as musings at work quickly turned into a full-blown side hustle the day we bought the Bulletin domain. Interestingly enough, that is not the company we’re running today. Alana and I faced many failures and multiple pivots on our path to building a profitable, venture-backed business.

Contently was a great place to work, but our day-to-day tasks started to feel dry. We were held to strict goals, and both of us were itching for a supplemental activity that exercised our creative sides. I loved to write, and Alana, an Instagram and Etsy huntress, loved discovering and supporting indie brands. Bulletin 1.0 was a digital magazine where readers could learn about cool, underground brands and shop their work throughout the story.

At first, we’d chip away at content here and there, squeezing in an hour or two after work or on a lazy Sunday. But as we spent more time on Bulletin 1.0 and nurtured our working relationship, it evolved from side project into side hustle. We faked meetings on our calendar to leave work early and interview a furniture designer. We’d wind up in a cramped and dimly lit studio in Chinatown on a Friday night, listening to a wallpaper designer recount his entire life story. We would spend full Saturdays holed up in Alana’s apartment, eating pizza while cursing our Squarespace site and perfecting a product grid. We fell in love with each other, we fell in love with our brands, and we couldn’t help but start to daydream, “What if we could do this full-time?”

So after eight months, we decided to try. We didn’t think it was crazy to go all in — we took this little publication very seriously. But our friends, parents, and partners weren’t so sure. Everyone gave us the third-degree: But how will the business make money? How will you support yourself? Are you sure this is a good idea? It was discouraging, but ultimately helpful. We wanted to prove them wrong, so we assessed our finances, built a budget, and strategized a real, feasible way to focus on Bulletin 24/7. Alana and I decided to stay at Contently until our last sales commission checks, applied to a few tech incubator programs, and tried to secure a small amount of outside funding from angel investors and VCs to provide some padding. We literally got turned down by everyone. Even with an inbox filled with rejections, we still felt determined to turn our daydream into a reality.

Through her research, Alana learned about a program called Y Combinator. At the time, they were taking applications for something called YC Fellowship, a two-month bootcamp for super early-stage companies looking for a small check and guidance from some of the smartest folks in Silicon Valley. We applied on a whim, nailed down our annual projections and growth plan, flew out to Mountain View, CA, to pitch Bulletin 1.0 and somehow got in. We were honestly shocked. And thrilled. They wired us $20,000, we quit our jobs at Contently, and on February 1, 2016, woke up to our first day as full-time Bulletin employees.

Even though $20,000 sounds like a lot of money (and it is!), it only gave us five months of runway — we only had a very small window of time to find a business model that worked. Alana and I cut costs wherever we could. We worked from her apartment in Brooklyn to avoid commuting and office costs, survived on egg-and-bean burritos for lunch and dinner, and decided not to pay ourselves a salary. We didn’t go out with our friends to avoid spending personal cash, lest we needed to tap into our commission savings.

We were giving our all to Bulletin 1.0, but the shoppable magazine model wasn’t working. We weren’t selling enough product and we were quickly running out of time. We went from six-figure salaries to making zero income, running a fledgling startup with no viable business model, and counting down the days until we ran out of capital. The brands we featured began complaining about low sales and threatened to abandon the site. It was terrifying. I’d have night sweats, tossing and turning at the thought of losing all my savings. I started serving at a local bar so I could afford things like healthcare and subway fare. We found it gut-wrenching, the thought of watching our company burn to the ground after just a few months of giving it our all.

We might have been on the precipice of failure, but we still managed to laugh and have a good time. During that rough three-month period, we learned first hand the value of loving yourself and your business, even with neither are at their best. We were determined to find a solution, so we went straight to our brands to see what they needed from us. It was evolve or fail, and we were okay with abandoning months of work in order to truly thrive.

Our pivot gave birth to Bulletin 2.0, a version of our business that actually worked.

In surveying our brands, we learned they didn’t really want or need more help selling online – they needed help selling offline. IRL. Many said they made most of their annual income at events like Renegade Craft Fair, Capsule, and Brooklyn Flea, as opposed to their websites or Etsy pages. But these IRL retail opportunities were exclusive, expensive, and infrequent. So Alana and I decided to launch Bulletin Market, an upscale, outdoor pop-up in the heart of Williamsburg, where brands could pay us a low fee to rent a booth and sell in-person for the weekend. We polled our brands in April, and our first market was in May. We found a cheap, abandoned parking lot right off the subway stop that we rented for six months. We were open every Saturday and Sunday from May through October, and hosted every product category under the sun – ranging from homemade hot sauce to soy candles to handmade skateboards. Brands were eager to sell with us, they made good money at the event, and we watched our bank account go from teetering-on-zero to flush-AF.

Unfortunately, this version of Bulletin was completely unsustainable. We’d wake up at 7:00 a.m. on Saturdays to pitch over 40 tents ourselves, sometimes in the pouring rain, sometimes in the sweltering heat. We were outdoors on the asphalt in the hot summer sun from dawn ‘til dusk. Cleanup was a bitch. The weather was unreliable. As the summer wore on, the tents broke left and right, the setup started to look janky as hell, and we were progressively more miserable. We were making money, but there was no opportunity for growth. Running the market was really hard. We didn’t leave Contently, ditch our fat salaries, and abandon our friends and family just to run an outdoor market. We wanted to do something big.

In November of 2016, we locked into Bulletin 3.0, the business you know today. As a direct response to the painfully exhausting, unreliable market model, we decided to open a permanent retail store in Brooklyn. That way, we’d be indoors (yay!), have more control over the customer experience and brand curation, and could feasibly have more than one location at once. The pay-to-play, fee-based approach remained intact. Brands pay a low monthly fee to host product in our store, see their sales in-real-time, and even host events in the space. We always loved the community feel of our markets, and we wanted to build a retail hub where likeminded brands could co-retail, collaborate, and connect. We had 30 spots to fill in our Williamsburg store. They were gone within 12 days of launching our new rent-share model. Soon, Bulletin was known as “the WeWork of retail space.”

Later that year, we peddled this new model to Y Combinator, the incubator program that had been so helpful to us when we first launched. We were accepted into the core program in San Francisco and flew back and forth every week for three months straight. The program was grueling – mentally and physically – but by mid-2017, we had solidified our business model, pitched over 100 investors, and raised $2.2 million in venture capital. It was enough money to add three key employees to the team, revamp our store design, open a second location, redo our branding and build a technology platform to make selling IRL easy. We had been operating on a shoestring budget since our launch back in March 2015. It’s been so gratifying to elevate our brand and spend on the things that make us more effective and efficient.

If you walked into our Williamsburg store today, you’d shop a store series called Bulletin Broads. With Bulletin 3.0, we open stores around rotating editorial themes rather than product categories. In this space, over 45 brands share rent through our tech platform, host weekly programming, and optimize their inventory in-real-time as a reaction to what customers like you are buying from us. All of the brands in this series are hand-picked by Bulletin, female-led, and 10% of all store sales go to Planned Parenthood of New York City. In a way, we’re helping other women turn their side hustles into full-time gigs. For internet brands that want to sell IRL, physical retail is a bitch and extremely hard to navigate. We’ve opened up a brand new revenue stream for now hundreds of female-run internet brands that want shelf-space offline.

Turning our side hustle into a venture-backed business was one of the hardest thing we’ve ever done. We failed straight out the gate, but we’ve never stopped trying. Thankfully, Alana and I have each other. But the real glue of our partnership is our dedication and belief in Bulletin.