ASHLEY SHAPIRO lines up sponsors for the South Beach Wine and Food Festival

Ashley Shapiro says she was "very confident and very competitive" growing and that she hasn't changed. Today, she's the sponsorship director for the South Beach Wine and Food Festival, securing $5 million in sponsorships from 150 companies, to benefit Florida International University. She also oversees ticketing for the 65 thousand Festival attendees- the largest event in Miami outside of the Super Bowl. Between work and her family, Ashley tells us, "I have a very fulfilled life."

FAST FACTS ABOUT Ashley

Where she’s from: Miami, Florida
Grew up with: mother, father, two younger sisters
Education: Bachelor’s degree in journalism from Northwestern University; Master's in hospitality management from Florida International University
Where she lives now: Miami, Florida
Growing up she wanted to be: a writer
Now she’s: sponsorship director at the South Beach Wine and Food Festival

Tell us about yourself growing up!

As a teenager, I was a know it all. I was very confident and I was very competitive. Actually, I’m still all of those things. I played a lot of sports. I was really into softball, but I also ran cross-country. My mom was a swim coach, so I swam. I played water polo. I didn’t love school, but I loved that right after school every day I was involved with sports.

Who were the adults you were close to when you were growing up?

I’m very, very close to my parents. In fact, they still live ten houses down from us, and help me take care of my kids. My dad worked a lot, but we were still very close. My mom first and foremost was always the consistent role model that I had in my life. For as long as I can remember, she always had like 12 different jobs. She owned her own property and managed property. She did accounting work for a state senator. She coached our swim team and water polo team, at our high school, well past when my sisters and I had left high school. My mom was always doing something constructive, and whether or not it was paying her a lot of money, it was keeping her busy and keeping her focused and energized.

Can you tell us about going to journalism school at Northwestern?

I went to journalism school because I fell in love with writing. I was always really good at communicating by writing. There’s a statewide writing competition that every high school student in tenth grade has to enter called Florida Writes. The top one percent get recognition by the state, and I got that for what I wrote. When I got that recognition for my writing, it boosted my confidence so I was like, “Great, I want to go to journalism school. I want to write for a living.” When I was in high school, in addition to loving writing, I was also really into TV and movies. I thought it would be really cool to be like an entertainment writer, so went I went to Medill, for journalism school. I focused on magazine journalism, because I wanted to write for entertainment magazines. My junior year, as part of the journalism program, I had to spend a semester working.

I applied and got an internship with TV Guide in New York. I was so excited. It was at that internship that I realized that I wasn’t going to be a writer. They put me in a cubicle. I would write really small, two to three hundred word articles, like a review of a show for the magazine. It would get published, with my name on it, but it would have been completely changed by an editor. An editor would never talk to me about it. They would just rewrite it and post it with my name on it, and that drove me crazy. I realized yes, it might be something fun, but it wasn’t a career that was going to sustain me. It convinced me that that’s not what I wanted to do for a living, but the writing skills were really great to have.

Why did you decide to go to graduate school for hospitality?

What I did love, actually, was living in New York. I ended up staying through the winter vacation, and I got really into the food scene. I was trying all different kinds of food, and going to different restaurants. I really got into watching the Food Network and cooking, and I was like, oh, I want to own a restaurant.

My parents said, “Well, finish your degree at Northwestern, and then go to hospitality school because if you want to own a restaurant, you’re going to have to know how to do it.” It just so happened that one of the top five hospitality schools in the country, Florida International University, is down the street from where I grew up. I applied to the master’s hospitality program at FIU, and I got accepted.

When I started my master’s degree, the South Beach Wine and Food Festival was going into its fifth year. They had one internship position available in their office, so my friend who was working there connected me with the festival founder and director, Lee Schrager. I interviewed with him, and I got the job. At the time, there were five people working there. I learned by interning for the festival. The internship was supposed to be ten or 15 hours a week, and I ended up working more like 30 or 35 hours a week because I loved it so much. I wanted to be a part of everything, so I would go in all the time and just sit and observe and try to help wherever I could.

What did you like about working for the Festival?

It was hectic, but in a way that had this end goal. I interned for two years. The first year I didn’t know what the end result was. The festival is in February every year, and when I finally got to see it happen, I was like, "Oh my god!" We basically take over Miami. The Convention and Visitors Bureau of Miami found that our festival brings more people to South Beach than any other event, with the exception of the Super Bowl. I felt like I was a true part of this massive event. It became more than just a job. It became something I loved, and not only that, I love the people I was working with.

Before I had even graduated, my boss had offered me a full-time job. When I was an intern, I was running their auctions and doing a couple of other minor things. When he offered me a job, he said, “Okay, I want you to take over all of our ticketing,” which I had no experience in. My boss said, “I want to do something for families. I want to do something that’s lower priced and about healthy eating and fitness.” He threw these two things on me that I was had zero idea how I was going to accomplish. I would try to figure it out as I went, and I definitely made mistakes, but I gained the respect of the people around me.

My Boss had confidence that I would keep working at it until I got it right. I would do it because I wanted to prove that I could do it.

Do you think your boss gave you those assignments because he knew your work from your years as an intern?

He knew I worked my tail off until it was right, so he knew I was not going to be satisfied with producing something that wasn’t good. He had confidence that I would keep working at it until I got it right, whether it meant working every day, from nine a.m. to midnight. I would do it because I wanted to prove that I could do it. He’s been an incredible mentor to me because he’s allowed me to take on things I don’t know anything about and learn them and make them my own, and that’s fueled the confidence that I’ve had.

What is your role now?

For the first six years that I was working full time, I was the ticketing director, and I produced that kid’s event, “Fun and Fit as a Family.” Then I told my boss, “You know, this was fun. I like producing the events, but I’d really like to take the next step with the festival, and take more of a management role.”

They offered me the position of sponsorship director. What that means is that I am responsible for writing all of the contracts for sponsors, and also making sure that all of the sponsors get what they are contracted for. We bring in about five million dollars in sponsorship each year for the festival. I reach out to all of the sponsors. I have a team, about eight people that work under me that help manage the sponsors. I sell them real estate, or I sell them an opportunity.

Once I sell the sponsorship, and write the contract, I pass it along and it goes into production. I still will be on all of the calls to make sure the sponsor is happy and that they’re getting an experience that’s going to make them want to return the next year. I’ve been in sponsorship for the last five years, and I still oversee all of the ticketing for the festival. We’re at about 65 thousand attendees.

Who do you work with?

We have a sales agency that works with us. Between myself and a colleague in my office and the sales agency, we go out and secure sponsors. We actually have a 90 to 95 percent return rate on our sponsors, so a lot of times, it’s just contacting our old sponsors and reviving the sponsorships they had the year before and just tweaking what they do. I work with each and every sponsor to determine what it is they want to get out of their sponsorship. I write the contracts. We have a legal department that helps me execute the contracts. There are about 150 sponsors, and I have a team of 12 sponsor managers that are subcontracted, and what I do is I assign each sponsor a sponsor manager, and that sponsor manger works with them on all the details.

Then the next step is that there are people that manage all of the events, so then our sponsor managers and I work with the event managers to say, “Hey, this sponsor has this desire at your event. How will it work within your space? Does it work with your venue? Do you have this power that they need? Do you have the Wi-Fi that they need?” Then it’s just tons and tons of emails and phone calls to make sure that sponsor is getting all of the things that they need to highlight themselves at an event.

What does your year look like?

My full-time job is the South Beach Wine and Food Festival, but I also work part time on the New York City Wine and Food Festival, which is in October. I work very heavily on South Beach from about August through March. Even though the festival is over in February, in March I’m very busy because we do recap calls with every single sponsor.

April and May are a little slow for us, which is nice because we’re going, going, going hard so long, all year. From to June to October, I’m doing a lot of New York-focused work. The overlapping time for New York and South Beach, August to February, is really the craziest time for me.

What keeps you interested in and excited about your work?

My day is never the same. Every festival poses new challenges, and every year my boss has higher expectations for how much money we raise. Both festivals, New York and South Beach, are charity events. The charity in South Beach is FIU, where I went to school, and the charities in New York are our two hunger charities. Our goal is to raise more and more money every year. At FIU, we’ve given back two million dollars every year for the last several years. Some of that money has gone into building a state of the art teaching restaurant at the school, and also it goes into scholarships, so tons of kids get to go to school for free, or for much cheaper.

In New York they raise about a million dollars a year, and it goes towards the Food Bank for New York City, and Share Our Strength, [which provides] tons of school breakfasts and lots of ways that the city is able to feed kids that may otherwise be hungry. The charity aspect keeps me going because I know that my job is actually giving back. At the same time, I’m also always doing something new and different and have new challenges. 

What fills your time outside of work?

Now that we have kids, what fills our time is our kids, spending as much time with them as possible. My husband and I have totally opposite hours. We just have Sundays together, and we usually make it a big family day. We hang out at the house; we’ll go to a park. Life has really changed in the last two years, but before that my husband and I love to play golf. We would travel all around to play. We play golf together because we love to compete against each other, and we’re hoping when the boys get a little older we can pass that along to them and that’s something we get to do with them.

You learn to produce an event of this magnitude, by doing it and by making mistakes and fixing them, and by learning from the people around you.

What do you think is valuable about going to school for event management?

The great thing about hospitality schools is that they’re almost always going to have an opportunity for you to be involved in an event. School didn’t prepare me for the job, but it gave me the opportunities I needed to get the job I have. You can’t learn how to produce an event in a classroom. You learn to produce an event of this magnitude, by doing it and by making mistakes and fixing them, and by learning from the people around you. I was working with event professionals that had been doing it for 30 years, and I just watched them, and watched what they did, and how they did things, and how they made decisions, and how they reacted in heated situations, or had to make decisions on their feet. I watched all of that and then just kind of did it myself, how it made sense to me.

What advice would you give someone who is interested in event management?

It’s all about experience, so volunteer wherever you can. Events, like the ones we do, are always looking for people to volunteer. Volunteer your time and learn from the people that are already doing it. It’s one of those things you just have to see it to understand it. Sometimes I will go to other events and see what they’re doing right and what they’re doing wrong, look at it from a consumer angle and look at it from a sponsor angle. If you’re a guest, what is the experience that you want to have? What is this event that I’m attending doing to make my experience better, and what could they change or make better? Look at it from a sponsor angle. If you had a company, and you were trying to promote your brand, how would you like to see that reflected in an event? It’s about a lot of experience.

I found this job that I loved, and it’s not glamorous in any way. It’s a lot of hard work and physically and mentally exhausting, but what I feel at the end of the day is accomplishment, and I feel fulfilled in what I do.

How did you picture adult life when you were a teenager?

My life is not anything like I imagined when I was a teenager. As a teenager, I never thought of myself as being married with kids. I think I thought of [life being] a little bit more fairytale-ish. I was going to be this famous writer, writing stories about my favorite TV shows and being a single person living in New York City and having fun all the time.

I realized that I was so close with my family, and I loved Miami so much, that moving back home was where I wanted to be. Then I found this job that I loved, and it’s not glamorous in any way. It’s a lot of hard work and physically and mentally exhausting, but what I feel at the end of the day is accomplishment, and I feel fulfilled in what I do. On top of all that, I got really lucky and I met like the man of my dreams. I have a very fulfilled life of work that I love and a family that I love coming home to and spending time with. I don’t have any time to feel like I’m missing out on anything else. I don’t know that, as a teenager, I ever understood what that feeling would be like, or that it existed.  

This interview has been edited and condensed.