From hosting some of New York's hottest supper clubs to teaching kids mathematics, co-founder and CEO of City Smarts, Danielle Florio, talks about how she found her passion in helping kids get through school and raising a few glasses along the way.
Do you remember your first week in New York?
I do. It was actually an interesting situation because I had gotten my first full time job out of college. I had been working desperately to get a full time job for about a year and a half before it happened. I had been living in West Chester previously, where I went to college.
It was really exciting, exhilarating and really empowering to be here because I had always wanted to live here since I was a little girl.
Where were you working?
I had graduated from college with a History and Journalism degree and I was trying to get into the magazine or production world but I really had no experience in those fields. So I was kind of knocking my head against the wall, applying to magazines and newspapers left and right and not hearing anything back for over a year.
Eventually one of my friend’s from college had a contact at Jones’ Apparel Group which is a huge fashion conglomerate. I got a job as the assistant to the VP of Sales and Nine West Apparel. I was working in the corporate headquarters. It was a really good first job experience. I loved the women that I worked with and I learnt so much, although I knew from day one that it was my way to get into New York. It was not the industry I wanted to be in, but it was a solid paycheck and it helped me make the transition.
When was this?
This was back in 2005. Growing up in upstate New York I really wanted to go to college in the city, that was the goal. I looked at a few CUNY schools but it was really expensive so it made sense for me to go to a state school.
I went to Purchase College in Westchester and I’m really glad I wound up there. I spent as much time in the city as I could.
Growing up did you come to the city a lot?
Not as often as I would have liked. My dad grew up in Long Island so we would constantly be driving by the city to see his family. I would also come down for field trips. One trip in 8th grade was particularly memorable, that’s when it kind of hit me that I needed to be here. I came down with one of my best friends and it was just magical. It was the culture and diversity here. I really love where I grew up but it’s really homogenous. There can be a lot of narrow mindedness.
Were your parents encouraging you to explore?
Yeah, they were really supportive of whatever I wanted to do. My dad has said many times that he would love to raise us kids in New York. I don’t know if my mom would have been happy in New York, she’s from upstate. I think it just wasn’t in the cards.
Do you think you would have a family here?
Yes. I can’t make any predictions about what the future will bring. I would love to say ‘oh I’m staying here and I’m not going anywhere else’ but sometimes it gets a little daunting, the financial climate here is difficult. Brooklyn is now the most expensive place to buy a home in the country.
If it’s doable then, hell yeah, I would definitely stay. I think there are ways to make it work. I think I’m a low maintenance person but at the same time I do want to have a family and I don’t want to be super stressed.
For now I’m here and I hope that it remains that way.
So how did you end up tutoring math?
That’s a good question [laughs]. My very good friend and roommate, Mark, is totally the reason that all this happened. I was approaching my two year anniversary at Nine West and I was getting to that place, like with any 9-5 job, where I was beginning to complain about it a lot. My roommate pointed out that I was complaining about the job left and right and said ‘why don’t you quit your job and let’s start a tutoring company’.
He had been tutoring on his own while he was at college and he thought about going to grad school but he was doing really well with his tutoring and he had a lot of clients. He was turning down families because he had so many people interested.
As I lived with him and watched him move through that part of his career I said ‘you know, you work half the hours I work, you make more money than I do, you love what you do, you have all these fantastic stories about the kids you work with. This is really a neat job!’
Even when I was saying these things to him I never thought ‘oh, can I do this?’ I was just making an observation. So when he suggested it I was like ‘wait, really?’ He said ‘I’ll teach you how I do it. Let’s do this!’ and I said ‘ok!’ [laughs].
It was the perfect time to take a risk like that. I have to say I don’t know if I would have done it without that kind of encouragement because I’m definitely very practical, I need to know I’m going to have an income and that I’m not going to be floundering for months.
So I took a vacation that January and went to Portugal for a week, came back and handed in my notice at Nine West. My bosses could sense I was going to leave and they were awesome about it. I learnt a lot there that I could apply to my business these days. I’m really grateful for that job.
It took a while to get started in tutoring, because I didn’t have a full roster of clients in the beginning. Luckily for me, Mark had such a strong reputation and he started giving me the clients he didn’t have time for.
I was always very good at math so I just had to refresh my memory on the curriculum, the flow of curriculum, how things are taught. I sat with Mark for hours and hours just refreshing and I sat in on classes that he taught.
He had been teaching at a school too?
We both actually teach at Baruch College for their continuing education program. He’s not a professor and neither of us have ever been full time employed at a school. He was teaching some classes at the time so I sat in on them and literally took notes on everything that he did. Then he had me teach the class! He threw me to the wolves, but it was the best way because I studied so hard and I was so dedicated.
I got a waitressing job in the neighborhood, just around the corner, which was such a saviour. Waitressing in the New York, you can make great money. It allowed me to make some extra cash.
It was about 6-7 months of part time waitressing and taking on a couple of clients here and there before I could take on a full schedule of students.
This is blowing my mind.
I don’t know what possessed me to take this leap but I’m really glad I did it. It’s funny because I grew up around educators, my mum was a teacher, my aunt… I even remember when I was a senior in highschool I did this brief internship at a third grade classroom and I really did not enjoy it. Maybe it was the age, because the children were so young it was intense. I don’t know if classroom teaching would be my bag. I went to college with an undeclared major. For a while I thought I wanted to be a psychologist. I didn’t really know what I wanted to do.
What does tutoring entail?
It’s changed so much since I started. When I begin I only tutored in math and I was working with a lot of younger kids, 4th - 6th grade. My experience, initially, was ‘wow, these kids are so bright’ but the way their teacher is teaching just isn’t getting across to them.
In a public school, the teacher has 35 fourth graders to deal with, there are going to be some kids who are spacing out. So my work with these kids wasn’t even that challenging, it was just getting them to build study habits of their own and become more willing to want to learn math, which even I still find challenging.
If a kid had a bad experience back in grade two they hate math forever. They could be in eighth grade and be excellent at it but they think ‘I don’t like it. I’m not good at it’. You have to find a way to derail that inner thing that has been planted in them.
That sounds like some of your psychology stuff is a part of it.
Yeah, I guess so. Nowadays, I do teach predominantly math and a lot of standardized test prep which isn’t my favorite part of what I do but it is a necessary evil.
In New York there are a whole set of high school entrance exams that need to be completed for a kid to get into the best private or public schools in the city. If you don’t make an effort preparing for these exams then you may as well not take them, that’s how hard they are. There’s this competitive nature in New York which I didn’t grow up with at all.
I just enjoy the relationship and connection I build with the kids. I think that our company is unique in that we wind up working with a lot of families long term. It’s not intentional, you want to teach these kids the skills so you don’t need to work with them years on end, but we found that we end up building a mentorship relationship. It just kind of happens.
You might be working with a kid for six months and they start to get it together and then the mom will come up to me and ask if I can help them with organization, or with their writing. They start really liking your presence. It’s really malleable what the tutoring can be.
You get closer with some families than others. There’s definitely a line you need to draw between their personal lives and yours. I’m constantly being asked all sorts of questions that I can’t answer. The kids are always trying to dig for gossip about my life, it’s hilarious.
It sounds so rewarding on all these different levels. Does the curriculum get repetitive or does it evolve?
It’s a little bit of both. What I do like about it is that I work with kids from so many different schools. There are patterns and it is repetitive in a way but what keeps me engaged is that every single student is so different. Even siblings are completely different. I was working with these fraternal twins for the longest time and they were polar opposites. It was kind of a trip because I was teaching them the same material but I had to approach it completely differently for each one.
One benefit of the repetition is that I can do it now without thinking. In the early days I never wanted to get caught not knowing the answer to a question. Now I’m confident, if I get asked a question I don’t know the answer to, it doesn’t bother me at all.
What do you say?
‘Oh that’s a really good question, let’s look that up together’ or ‘I’m not really sure. Let’s find a way to use your textbook to figure it out.’ In the early days if I was caught off guard with a question I would probably have felt really insecure about it. Are they going to the tells their parents that I don’t know? That was a big motivator to keep studying and make sure I knew what I was teaching. I was always so much more prepared than I needed to be which wound up being a benefit.
It sounds like the business is doing really well! And the other aspect of your life is the amazing Supper Club ...
Yes, the last few years have been big time growth spurts for us, which has been exciting. At the time we started City Smarts, we were also putting our free time into the Supper Club.
Supper Club had really taken off in a way that we did not expect it to. It was part of the serendipity of moving into this loft. Mark and I moved in 2006 with a woman named Nora, who was the leaseholder. She’s such an awesome lady and we’re super good friends now.
From the very beginning we established such a great rapport with Nora that it just felt really natural, really organic. We felt like a family right away. Mark and I asked Nora if she’d be OK if we had some friends over for dinner, we literally meant having a few friends over and cooking some dinner, super casual. Nora was like ‘I love having friends over for dinner. I actually used to do this thing called the Whisk & Ladle Supper Club.’
Nora is the founder of the Supper Club and when we moved in with her she started explaining the concept to us. She had been debating between going to law school and culinary school. She chose law school but she grew up with parents who just cooked all the time and that was something that she grew up with. For the holidays they would have these really formal five course dinners, her whole family would dress up in ball gowns. But it was a riot, they were not stuffy at all. They did it for the fun and hilarity of it.
So Nora and her sister started throwing these elaborate dinner parties as a way to maintain this tradition that they grew up with. When she explained this concept, Mark and I thought it was the coolest thing we’d ever heard. So she suggested that we start the Whisk & Ladle Club up again.
When we told all our friends they were like ‘wait, so you want us to come over and pay you to have dinner at your house?’ It was such a minimal cost, it was really just to pay for the meal. That first dinner was more of a party with food everywhere and we printed these cards that explained what the supper club would eventually be.
We met some people that night who were really excited and interested in what we were up to so we wound up throwing a couple of dinners in the fall and it just snowballed. Our friends had so much fun that they went and told their friends, their roommates, their coworkers. Mark suggested that we launch a website and instead of mailing out invitations, which is what Nora used to do, we’d organize the whole thing through email.
There was no intention that this was going to be a big thing. I think there were definitely a few supper clubs around in the city but we never looked into it. I had no idea that there was a “thing” happening in supper club culture.
Our first bit of press happened about six months after our first dinner. What was funny was that we actually had Gawker and Thrillist at a dinner but we didn’t know it. They had signed up for a dinner and we had no idea. We had this amazing night where we had so much fun with the guests that we went out with them after, which rarely happens. At the bar one of them mentioned they worked at Gawker and were going to write us up.
We were nervous but we wound up having a couple of great pieces of press in the beginning and because Gawker and Thrillist posted in close proximity of each other we got a ton of emails from people who had seen those articles. So it grew into something much bigger.
Our focus at that time of ours lives started to turn to the Whisk & Ladle club which was so fun and so rewarding, even though we weren’t really making any money. It was so exciting and we were meeting such amazing people. Some of ours closest friends are people we met in those early years of the supper club.
About 6-7 years after that, we were getting a little older and the tutoring business was growing, and we said to ourselves ‘we need cool it with the Whisk & Ladle a little bit’.
How often do throw dinners now?
Nowadays, we do it every three months or so. Sometimes we’ll do two close together and put something on the books ahead of time. We’re finding out now we have so much desire to do them but so much less time to commit to the dinners. It often happens that we’ll put it on the calendar and when it comes up we’re so busy with the business that we’re kind of shooting ourselves in the foot.
How do you decide who’s going to come to these dinners?
Our mailing list is insane so we can’t actually email each schedule to every subscriber. We usually wait until we have 2-3 dinners lined up before we email a schedule. We also do events, for example we’ll have two dinners and a music event or an art auction or mixer. We’ve done some really interesting whacky events here.
We’ll start ‘piece meal’ emailing it out to parts of our mailing list. Our friends and family always have priority. We’ve found that when we have the room half or a third full of friends and family, people who know us and the space, it makes the dinners so much more successful. It winds up making a better dynamic.
This whole lifestyle sounds great, really rewarding, a really great network ...
It’s been so serendipitous. I think moving into this space changed my life. It was not something I ever expected, it was not something I intended.
So you like living in Williamsburg?
I do love living here. The neighborhood is changing a lot. It’s been a bit tricky to get used to. I’m totally part of the gentrification but it’s becoming so much more crowded and it’s so expensive here now. I’m really lucky I moved here a long time ago.
There are great restaurants, a lot of my friends live here and I feel safe in the area and I can bike around easily.
In terms of favorite places, I love Cafe Mogador, it’s so good and healthy and the people are great. The restaurant I worked at when I started tutoring, Sweet Water on N 6th street, is one of my favorites. It’s been in the neighborhood for a really long time.
I don’t go out drinking a ton but I love Glasslands, which I know is going to close at the end of the year but that’s a really great venue.
There’s a lot of energy here. The building is awesome too. The neighbors are awesome and a lot of us have been here for a really long time. We have more of a community than we’ve ever really had here. One of our next door neighbors actually works for us as a tutor.
Despite everything going so well, is there any advice you would give your 18 year old self? That’s not just ‘keep going, everything is going to be great!’
Probably the same advice I would give my 32 year old self, which is to slow down a little bit. Stay present with what you’re doing. As I’m sure you’ve noticed, I’m very hyper and I have a lot of energy and I think I take on a lot, I say ‘yes’ to a lot of projects. I’m always happy with the projects I’m involved in but sometimes I think ‘I overdid it this week.’
I want to be a bit more grounded and present and not constantly thinking about what I need to do next.
What do you think of when you think of New York?
I think NYC has really embodied the idea of ‘freedom’ to me. In that - you can do anything in this damn town if you work hard and set your mind to it. We are all little sponges soaking up everyone and everything the city has to offer.
I never felt this kind of freedom growing up in upstate NY. It’s like that feeling of getting your license and driving away from your parents house for the first time. It’s exhilarating.