What were your career aspirations in college?

In retrospect, it’s hard to say whether I even had any aspirations. I always find it fascinating when I meet kids in high school who already know what they want to do. I got a B.S. in Media, Culture and Communication from NYU. I knew I liked marketing and I had an interest in corporate communications and in editorial. I started as an intern the summer after my junior year and that’s when I fell in love with working with brands. That’s the direction my aspiration grew.

My brother was an entrepreneur and started his first business when he was a senior in college and, of course, I looked up to him. So I think I always had an entrepreneurial spirit just from that. I don’t think there was a clear path but I was interested in the communications and marketing realm.

What were you doing before work before starting your company?

My path was dependent on the stars aligning. I started my career as a brand strategist for an Omnicom agency, Wolff Olins. As luck would have it, the hair care company Living Proof came to our agency prior to their commercial launch. At that point it was a startup in stealth mode. It’s now part of Unilever.

They came to us and we did everything for them on the visual identity end, including the name. I was very early to the company, I was one of the more junior hires. So, by the nature of being more junior and ne of the first, non-executive hires, I got to do a ton of stuff because I was early-stage and able-bodied.

Even though I sat on the brand marketing team, I was sitting cross-functionally in almost every meeting—product development, supply chain, sales and education meetings. I was helping on fundraising to whatever extent I could. That was how I came to learn what it actually took to operationalize a business.

I wasn’t in a big corporate environment where the teams are incredibly siloed and you might be a brand manager that sits with other brand managers on one particular product line never to see the likes of HR and finance and supply chain and all of these other folks. I was actually in the room representing brand marketing cross-functionally across the entire company so I got to learn very quickly what everyone else did and then how it all came together.

I ended up joining Living Proof around September of 2008 and was there until 2012 as a brand manager. I learned so much in my time there and it was what gave me the confidence to start The Sill, which launched in the summer of 2012. Without that insight I don’t think I would have understood or appreciated what it took to start a company or what puzzle pieces even needed to be put together.

Where did you first get the idea for The Sill?

My early career was split between New York City and Boston. As a young professional, my time was spent focused on work, mostly. My apartments were always small studios on the top of a six floor walk-up, or garden level with little to no natural sunlight. I realized early on that I missed the natural world of my childhood I had completely taken for granted.

When I started to try and incorporate plants into these spaces I found it incredibly difficult. I wasn’t getting the right information in the stores, of which there were few, and I was pretty much killing them all! It occurred to me that this major shortfall was actually a big opportunity for me to make a positive impact. By creating a consumer brand that delivered plants in a more convenient way and educated novices like myself on taking care of them, I could encourage more young people to incorporate plants into their day-to-day lives.

When did you know you wanted to leave your previous career path behind? What did the transition from your previous career to launching this company look like?

The more I dug in to the market and the customer experience and the existing landscape of options, the more excited I got. I couldn’t not do it. That’s how it felt. It seemed impossible not to try to build this company.

I worked on a basic concept on nights and weekends and then quit my job at Living Proof once I felt I had something solid. I consulted for a bit on the side in the first few months but even that seemed like a distraction. After completing a small Kickstarter, The Sill was my full-time gig. It’s been over seven years now!

Letting go of a stable job is scary for most people, did you have a financial safety net?

I started thinking about The Sill conceptually about six months prior to leaving my full-time job so I was able to start to save money. I was living in Boston so, first things first, Boston isn’t nearly as expensive as New York City. So that was super useful. I also had a long-distance partner, now my husband, who was incredibly supportive.

I didn’t go out as often, and was mindful of what I spent at the grocery store. In the first year of the business, I wasn’t buying clothes. You know, you eat a lot of peanut butter sandwiches and are not booking big trips and living a lifestyle that you would if you had a steady paycheck.

But I knew I needed a certain amount of money just to get by. I knew that I was going to join my boyfriend in New York, which is where I eventually launched The Sill. Prior to that I had moved in with my friend and there were three adults living in a two-bedroom apartment. You basically do what you need to do to save money. They were saving for their wedding and I was saving up to quit my job.

There were hard conversations I had with my boyfriend. I spent a lot of time on a Bolt Bus or working. We became domestic partners so that I could go on his insurance. I did have a consulting gig early on in the first couple of months so I had some income still coming in, but other than that it was just my savings. I knew I had to get comfortable going to zero. This is partially what inspired the Kickstarter: I realized this was going to cost money and it couldn’t just be my money.

Has your understanding of financial stability changed since starting The Sill?

Yes, but honestly, it’s more because I’ve literally grown up while running The Sill. I went from being in a relationship in my twenty-somethings to married with a kid in my thirty-somethings. It’s a lot of change! The real difference is how your concept of time and money warps when you’re running a high growth start up. Everything takes more time and costs more money.

I started the Sill when I was 26, I had worked at Wolff Olins, I had worked at Living Proof, and had a slew of internships. I had something I could fall back on. I knew if this didn’t work I had a viable resume and was confident that I am marketable and could get a job—that was my safety net. That said, I never took a real paycheck in the early days. It was constantly: “Do I need this money? Or does the business need money?” And it is a struggle. Now, I take a salary but that’s like five years into the business.

Honestly, I’m still probably making below market value. If I went out and got another job right now I’d probably make more money than I do being CEO of my company. The trade-off is that I’m doing what I love.

How has your company been raising capital?

I bootstrapped the business for the first five years. In retrospect I probably should have raised earlier. We’ve raised $7.5 million since 2017. The bootstrapping definitely taught me to be frugal and pragmatic. Some investors like this mentality, others don’t at all. I want to see The Sill [go] all the way. That changes the way we approach running the business and how we consider profitability.

What’s currently your biggest business challenge?

It’s all hard—and I actually think that’s fine. I relish in the challenge and the fact is, if it wasn’t hard, it wouldn’t have a meaningful outcome. It’s obviously a cliché, but if it was easy everyone would be doing it. It depends on the day, probably whatever I’m doing, if it’s hiring or raising money or coming up with a strategy. It’s just finding the coping mechanism for facing challenges every single day. That’s what’s hard.

What’s been your company’s biggest victory so far?

It’s a lot of small victories that build up over time. Going west has been one of the biggest challenges we’ve faced. We have three physical locations on the west coast since the start of this year. We now have a California distribution center, a store in Los Angeles, and a store in San Francisco.

I was literally on maternity leave when the distribution center and the lease for the Los Angeles store were signed, so to be able to delegate and have confidence in my team and be sort of at an arm’s length was new. Those were big hurdles, both as a founder and as a company.

As a founder, you want to be involved in everything. For LA, the official store opening was the first time I stepped foot in the store. We’re based in New York, so it’s very far away and there are a lot of operational and logistical and people challenges that go along with having a dispersed workforce. That said, it’s been incredible. Now we feel like a national brand and like we’re really moving upward.

What does your self-care routine look like?

I’m still figuring this one out. I should do more. I just went to the gym on Sunday and I feel very good about it. I think I spent 30 minutes there. It’s amazing that some people do the whole bootcamp at 5 a.m. and go into the office by 7 a.m. and work 14 hours. But when people actually ask me what I do for myself I say I work—it is what I love to do.

I have goals and aspirations to do more yoga and gym-going, but I’m honestly just not there. If I get to eat lunch I’m excited. It’s not at all the glossy magazine cover of “Oh, I’m an entrepreneur!” I shower every day and I go to bed by 11 p.m. and sleep for eight hours. That’s as much as any CEO and mom can ask for. I genuinely love every crazy minute so I honestly don’t have a lot of complaints about my lack of self-care. But I should probably exercise more.

Do you ever suffer from imposter syndrome?

Yes and no. More than seven years into the business I doubt myself less, but I struggle with the outside world’s perception of success. It’s hard when you get to a place of confidence in yourself but the goal line for investors and the media keeps pushing further and further away.

What are some resources that have helped you on your journey?

I read more than books and podcasts. I live five blocks from the office so I don’t have a commute every day. When I have time to read, it’s pure fiction, I’m not really reading business books. But, I’d say, find yourself a tight network of like-minded founders that you can connect and commiserate with. My time with other founders anf CEOs is far more important to me than any book or blog.

What’s your advice to someone who is considering taking “the leap”?

Do it! Sometimes people just need a kick in the butt. For me, it came down to someone who would just say, do it—stop overthinking, stop second-guessing. You won’t know until you try, so go try.