The options were: selling Rookie to a bigger media company, partnering with one of those media companies (where they’d pay us to make content that they could also use), getting investors, or asking readers for donations or subscriptions. In the meantime, we could no longer afford to have an office or as big a team of editors. We had to start publishing fewer pieces, and could not take on anything too editorially demanding, like regular news coverage. This has been especially frustrating while the world has been more on fire than usual, and because I know how badly Rookies have been wanting to read and write about it. When this became particularly distressing, I would remind myself that scaling back meant that we’d be able to do more news coverage in the future.
I was getting so much advice from different people at this time that it’s hard to remember how taking money from investors became the next step. I know that it felt too soon to sell it: I wanted it to be more sustainable first, and I wasn’t ready to give up control. I know that a partnership with a media company seemed like too much work for our small team, and not lucrative enough to get Rookie to a more financially manageable baseline. (Actually, we did do a podcast produced by MTV News, and that was great, but it wasn’t going to save the business. In fact, during that partnership, Viacom shuttered MTV News and laid off their editorial team, citing a “pivot to video,” so our podcast ended in the middle of its first season. Have I mentioned that most media companies are struggling?) I also know that the idea of taking money from readers made me feel an immediate and intimidating sense of responsibility. (In retrospect, that may have been a more manageable kind of responsibility than money from investors, and could have been a hint to how I’d feel about investors, but you can’t know what you don’t know.)
We started meeting with venture capitalists and pitching them on Rookie in fall 2017. My Bryce problem had calmed down; now, I even wanted their money, and was ready to channel my inner Bryce to get it. If some clickbait-y website could raise tons of money from investors and then eventually sell for tons more money, why not something that’s actually good? (In most cases, this question answers itself.) We had put in the work, Rookie was already influential; if this was what we could do organically, imagine what we could do with more resources.
Younger-me would be skeptical and then relieved to hear that we didn’t encounter that many Evil Bryces. We met a lot of Good ones, and Good Hayleys, and hell, even a Good Spike (*weird sincere laugh*). (My idea of Good and Evil also got a little more nuanced.) A bunch of founders and investors were enthusiastic, happy to give advice or introduce us to other people who could help. I did not have to make Rookie sound like something it wasn’t and I didn’t feel gross telling people they should fund it.
I learned from having to think harder about and explain why I thought Rookie should expand. I read books about entrepreneurship and discovered that it is so much more interesting and creative than I’d realized. For me, writing had always been the most directly communicative, expressive act, and now I liked figuring out how we could fan out that kind of voice and intimacy across a whole Rookie ecosystem: more content, more social media usage, more books, more merch, maybe even a subscription box, and/or a camp, and/or TV, and/or movies, and/or a planet, because why should planets be reserved only for Elon Musk and dead Mormons??? Some investors were hesitant to invest in a media company at this moment in the industry, but to my great surprise/fear, some were not. However, the kind of growth that would be expected—the kind of money it would suddenly have to be making, and at what speed—scared me.
When you pitch to lots of people, you get a lot of conflicting advice, which is good if you’re too closed off to criticism and would benefit from taking some in, and bad if you’re susceptible to feeling inadequate and will take all feedback as gospel, sending you in multiple directions at once. More than anything, it’s proof that there is no objective authority, and that the final decision is always yours. Thinking back on the fundraising process, the most exciting part was mining the richness of the Rookie universe as it already existed, and imagining the possibilities for the future. That’s one of the sadder aspects of having to end it now.
One woman venture capitalist told us, after hearing my very nervous pitch, “I hate to say this because I hate that it’s true, but men who come in here pitch the company they’re going to build, while women pitch the company they’ve already built.” The men could sound delusional, but they could also sound visionary; women felt the need to show their work, to prove themselves. This wasn’t a note just for my style of pitching (flat, part-Troll doll); she was encouraging us to dream bigger and start anew. What would Rookie look like if we saw everything up until that point as just research? It had started as a response to mainstream teen and women’s magazines. Many of those have gotten more progressive and more interesting, or have folded, or are less powerful (the way all publications are now less powerful). What would a teen magazine of today look like? Maybe not a magazine. As a publication, we could only be a platform for young people who were already confident enough to send in their work—what if we shifted our focus to people who don’t feel that way? Maybe it would become a journaling app—something that makes creative expression less scary, that focuses on its health benefits rather than putting on the pressure to make something shareable and cool. Or maybe that’s too limiting. Actually, the most valuable thing in my life had been relationships, mentorships. Maybe Rookie should be a matchmaking app for mentors and young people. Or a Girl Scouts that was also somehow profitable. Or maybe all of these services could live in the Rookie universe with a redesign of the website and a new app—though we were also told that if an app is good and intuitive, it only has one or two functions. Either way, we’d have to raise a smaller amount of money first, just to get the site itself to a more manageable baseline, and would explore those other directions after.
I told myself, and investors, that the hard part was over—building an audience, carving out a unique voice—and the rest would just be paint-by-numbers: hiring people, making more content, “scaling,” as it were.
But the paint-by-numbers part is actually harder if it’s not what you really want or need to do.