Starting a Business from Scratch When You Know Nuthin About Nuthin

Ester: Hello! They’re doing road work on Flatbush outside my window so it smells like the Elephant House at the zoo in here. How are you?

Rachel: Hot! It is very hot in my apartment, overwhelmingly hot. The thing about how heat rises — it’s true! I live on the top floor and it is as hot as 7th grade science teachers everywhere said it would be.

Ester: That’s rough. At least your apartment isn’t defying the laws of physics, though. That might be dangerous. Ok, so, you and I were talking about starting a business! Perhaps you’d like to introduce yourself briefly before we launch into it?

Rachel: I’m a writer who was until recently a staff writer and has now become a freelance writer, which has been alternately exciting and paralyzing. But I just got a “standing desk” (a bar table, whatever), which I feel is really going to turn things around.

Ester: Totally. And you and I met for coffee yesterday to co-work and also commiserate about how many jobs we’ve had and lost since college even though we are smart and hard-working Good Girls because New York chews people up and doesn’t even bother spitting them out most of the time, so we’re like lodged behind a molar in New York’s mouth and will be until the city decides to floss. Whew. So we were like, maybe we should start a business!

Rachel: We were! Given that we have had All the Jobs, we are obviously in a strong position to start at least one of the businesses.

Ester: My pitch to you was Swarthmore & Swarthmore LLC: College Consultants Extraordinaire, since we both went to the same ritzy liberal arts school and were obsessed with the college admissions process. Kind of still are, frankly. Also we have experience walking students through the entire process from picking their schools to fine-tuning their essays.

Rachel: I was thinking this morning about being obsessed with college admissions still, many years out, and what that says about me, which is probably nothing good. But! Given that we boast a combined twenty-plus years of being obsessed with college admissions, I feel like this is something we are well-suited for. And we’ve both tutored. And edited. And edited people we were tutoring. SSLLC:CCE could be the business we were born to run! And also, a pillar of consistency in the uncertain writing world.

Ester: Quite! As the genie in Aladdin would say (RIP Robin Williams), though, “there are some provisos, some quid-pro-quos …” Like, no one in my family or my immediate friend circle has started a business. I do not really know how one goes about it. Put an ad on Craigslist? That’s so 2002.

Rachel: Well, my mother has a MBA, but MBAs are annoyingly not genetic. My best idea was to put a flyer on a bulletin board, so, you know, case in point.

Ester: Hey, don’t knock flyers. I hired a lady to watch babygirl once because I really liked the flyer she put up at a coffee shop. The flyer turned out to be brighter than she was, but still. It did its job.

Rachel: I feel like we could make real nice flyers. And then … what happens? Given the number of long-form articles about people who have started businesses I have read, I am embarrassingly clueless about the logistics of business-starting. Flyers + winging it?

Ester: Flyers go well with winging it! At least sonically. Maybe plus word-of-mouth, plus an amateur-ish website, plus a well-crafted ad placed in neighborhood parent listservs? Or maybe we need someone with actual experience to advise us. A Board of Directors. The nice thing is we don’t need too many clients.

Rachel: That’s true! We just need a few clients — ideally, clients with many, evenly-spaced college-bound children.

Ester: Right! When I’ve done this freelance, that’s sometimes how it’s worked. I helped one woman’s older son navigate the whole process and then I helped her younger son.

Rachel: Where did that client come from? To the extent that I’ve done this/anything like this, it’s been through friends who are teachers and relatives who have children.

Ester: Oh, she was my boss at my actual job, so she knew I was good at writing and advising. It was both good and bad: when she asked, I felt like I couldn’t say no, but she also disregarded the disgustingly low amount of money I asked for and paid me something more market-rate.

Rachel: That is admirable! Or just ethical. The idea of pricing myself — here, and everywhere — is overwhelming and I don’t think I’ve ever done it well.

Ester: I’ve gotten better at it, in part because I’ve had to. Research helps, looking online at what other people charge, and reading things to pump me up about how women need to advocate for themselves, not be shy about asking for what they’re worth, and so on. FEMINISM. LEAN IN. LENA DUNHAM.

Rachel: That’s helped me, too! Making it political! It feels better to ask for better rates when it’s not about me, it’s about THE CAUSE.

Ester: Absolutely. The cause of “food” or “self-respect” isn’t enough, somehow. But having two of us in the business will be good because we can bolster each other. My best friend is an illustrator/graphic designer and I’m much better at encouraging her to price her work according to its actual worth than I am about following my own advice; but if you can do that for me, I can do it for you, and we’ll be okay.

Rachel: Definitely. As soon as we design our flyers. Ones that are brighter than we are, ideally.

Rachel Sugar is a writer and editor in New York. Ester … you know Ester.