One year of olives

Our currently indicted mayor Eric Adams said this last winter about New York City: “This is a place where every day you wake up, you could experience everything from a plane crashing into our Trade Center to a person who is celebrating a new business that’s open.” Though there’s certainly no way he could have known it, one of those new businesses was 18 Olives, which we launched a year ago today.

I think some people would say it’s a fool’s errand to start a comms and content agency at a time when this work is constantly devalued (primarily by people who don’t and can’t write, I should mention), and when some people still operate under the misguided impression that generative AI is sophisticated enough to competently do our jobs. I say: it beats working for someone else for a living. 

The material work we’ve done over the past year is illustrative of my desire to have a “year of yes” — we’ve started newsletters for consumer brands with massive, engaged audiences; we’ve overseen the social media strategy for activist investors taking on entertainment giants; we’ve done thought leadership and written product copy and blogs and website copy. All of our clients have come through my network — a blessing, yes, but also the unintended result of a decade of networking and making connections with good people.

There are also a lot of things I think we need to improve. I want bigger scopes of work. I’m hungry for more ambitious revenue goals and larger companies to work with. I want bigger challenges. I also want us to be able to charge enough money to not only keep ourselves paid, but to grow our team and hire writers and make this an actual agency. We have a lot of learning to do about operating a business before we get to that point. I need to get comfortable with lead generation and doing cold outreach. I need to be a better self-advocate in negotiations. I need to ask for more money without feeling like I’m going to puke. I need to be better at having hard conversations and handling rejection. The list goes on.

I could not have done any of this without Eliza and I mean that in a very literal sense — would I ever registered an LLC for the business without a partner willing to take the reins? (No.) Would I let myself be cowed by the occasional former client who treated us badly and took advantage of our newness? (Yes.) It’s exceedingly rare for me to find someone who matches my temperament and sense of humor in near-equal stride, and it feels even rarer for that person to be my cofounder. 

When we started 18 Olives, I was operating in survival mode. I was coming off of two layoffs in 11 months; my savings was drained and founding a business felt like a last-ditch effort and a hope and a prayer and a bet on myself. But it also felt like the right thing to do, maybe the only thing to do. 

We’re starting to think deeply about year two of 18 Olives and what that looks like. For the first time in as long as I can remember, I don’t want to come at it from a position of scarcity — I want to continue to build a healthy business I’m excited about every day, and to do it with intentionality. I want this to be sustainable. I want an office. I want to hire. I want to be profitable, and I want to share those profits with other partners in the business. I’m grateful to you for reading these reflections and bearing witness to the messy and imperfect first year of 18 Olives. Here’s to year two!