Interview with Jennifer Gilbert, Founder and Chief Visionary Officer of Save The Date

Jennifer Gilbert, founder of Save the Date, serial award winner, speaker, author of I Never Promised You a Goodie Bag, and survivor of 37 stab wounds inflicted in a brutal attack. Listen in.

Learn more about Jennifer at https://www.savethedate.com/founders-message/

Podcast Transcript:

Julie Roehm: 00:00 Hello. Today I'm here with Jennifer Gilbert, who is the founder and chief visionary officer of Save the Date, which is based here in New York City. It's a hospitality and special events company, and they've just celebrated 25 years in business, which is super exciting.

What's very interesting about this company is that she pioneered a very unique approach, which has earned her several awards, including Ernst and Young's Entrepreneur of the Year, participation in MIT's three year Birthing of Giants Fellowship Program, and also Working Women Magazine's Entrepreneur Award of Excellence.

As a result, not surprising, she speaks to international companies and industry peers, facilitating discussions about resiliency, entrepreneurship, and endurance, including a TEDx talk on the entrepreneurial spirit. She's been a keynote speaker at BizBash and a fixture on a season of the Real Housewives of New York City as the event planner of choice. I love that one. That one we're going to talk about.

But one of Jennifer's greatest accomplishments is her book entitled, I Never Promised You a Goodie Bag, probably up for one of the best titles ever. She's also writing her second book right now about sales and the art of the cold call. So thank you for being here. I'm so excited to have you.

Jennifer Gilbert: 01:22 Thank you.

Julie Roehm: 01:23 You've got such an amazing ... first of all, obviously as a female entrepreneur, it's amazing, but just your story even as it reads from your bio, which doesn't even begin to have people understand the depth of who you are and how this came about, is so exciting and impressive and you do so much to try to give back, which I love about you. But I would love for you, as I try to do in all of these sessions, is give a little background about just your entry into the world. So like your childhood. I always feel like it's interesting and grounding for people to hear how people spent their early formative years.

Jennifer Gilbert: 02:02 I really think I was born an entrepreneur. I mean from the time I was little, little, four or five years old, I used to gather the neighborhood kids and I would put on a circus starring me, of course. I would swing on a tire, do acrobats and charge them. I mean I was nice.

Julie Roehm: 02:20 Shut up. Where was this?

Jennifer Gilbert: 02:21 In Westchester.

Julie Roehm: 02:22 In Westchester. Okay.

Jennifer Gilbert: 02:23 And then I would freeze our basketball court, which was basically cement.

Julie Roehm: 02:28 In the winter?

Jennifer Gilbert: 02:29 Yeah. And then I would be like ice skating rink and charge people. I mean I was always doing this. All through high school I had some side hustle going. I was selling jewelry, I was making things all the time.

Julie Roehm: 02:40 No kidding.

Jennifer Gilbert: 02:41 No kidding. I loved it.

Julie Roehm: 02:42 I honestly had no idea. I had no idea about this.

Jennifer Gilbert: 02:45 Yep.

Julie Roehm: 02:45 So where did you, did you have this, obviously the entrepreneurial thing was just sort of innate in you and natural, but did you then think, "Okay, I'm going to go to school, I'm going to go to college and I'm going to study," what was your thinking?

Jennifer Gilbert: 03:01 I went to college. I studied business and marketing. And after that I took a sort of, I would say semester, but it was really more like a year off. But I worked in London. So I got a Visa to work in London.

Julie Roehm: 03:19 Where did you work there?

Jennifer Gilbert: 03:20 I would have done anything. But it just so happens that I got hooked up with a man who did huge events and concerts at Wembley and everywhere else.

Julie Roehm: 03:30 Oh fun.

Jennifer Gilbert: 03:31 So I was sort of in charge of getting things for free, and I had never done this before, but he was like, "Oh, you're an American, you have no problem asking for things."

I was like, "All right, I don't." And I just started doing production for him.

Julie Roehm: 03:45 And a natural hustler by birth.

Jennifer Gilbert: 03:48 Yes.

Julie Roehm: 03:48 And so you had all those years of training.

Jennifer Gilbert: 03:50 I would say I'm a friendly stalker.

Julie Roehm: 03:53 You are.

Jennifer Gilbert: 03:53 And I'm very persistent.

Julie Roehm: 03:55 And people, unless they're looking at the site and see your picture, she's also beautiful. So the people who are going to talk to you anyway. And so then the world is your oyster.

Jennifer Gilbert: 04:03 I think if you're humorous and you get people to laugh. And not sound like a sale and are friendly, and they're friendly and somehow you just have to get around that strange thing. I mean, I don't know. Even now, I mean my book that I'm working on is about the cold call. I always don't understand why people are scared. I'm like, "It's a phone. No one's going to hurt you. Just ask for what you want." The worst they can say is no.

Julie Roehm: 04:30 I know. I know, right?

Yeah, it's, but it's hard. People have a very ... I talk about it and I think on a few of the other episodes of my podcast, but you know, children, you've got children. I have children. You have three children. I have two. And my son who's still in high school, my last one, he'll come home and he'll say something, some drama of course. And I'll be like, "Pick up the phone." Or, "Go and pull them aside. Don't text them, don't story."

And it's happened even twice in the last couple of weeks. And it's something that you have to learn because I think this generation especially, that's a very uncomfortable thing to put themselves out by their voice or in person.

Jennifer Gilbert: 05:13 I think so. I mean I always say it's incredible what you get when you actually ask for something. Like anyone who asks me for help, I help them. Why not? You know, and it was very sweet because we had a big celebration for our company this year. All the women in my office, because I happen to have only women, made me a sign because I love text, and it's my favorite quote and it's, "You don't ask, you don't get."

So they made it for me, a big sign. It was really, really cute. And I do that to my kids too. I'm like, "You don't ask, you don't get."

Julie Roehm: 05:48 And it's so much harder to say no to somebody in person. I find it's easy to do it digitally. It's much harder to do it when you're looking at somebody [crosstalk 00:05:57].

So things weren't always easy. And in fact, your book, I Never Promised You a Goodie Bag, goes into great detail. So I know that you've shared this before and are willing to share, but you came back from London.

Jennifer Gilbert: 06:10 I did.

Julie Roehm: 06:11 And came back to New York.

Jennifer Gilbert: 06:12 I came back from London. I mean I wrote this, but this was back in the '80s and I was wearing a Donna Karan onesie and a power suit, and I'm imagining myself working on Wall Street, because I would've probably gone right into Wall Street. And we plan and God laughs kind of, but this was not very funny.

I had really just been back maybe a week and I went into the City to visit my girlfriend, who was my roommate. And unbeknownst to me, I was followed off the subway and it was a beautiful day. I mean, the sun was shining, it was in May, like perfect four o'clock. And I was followed off the subway and this man followed me into my friend's apartment building, and I had no idea, and I will skip the gory details, but he proceeded to attack me and I was stabbed 37 times with a screwdriver. And I mean it was in the hallway and then it continued into my friend's actual apartment.

I mean, I absolutely thought I'm dead. This man's going to kill me.

Julie Roehm: 07:30 So you were running, he's attacking you, you're running, you're trying to get to her. Was she there?

Jennifer Gilbert: 07:34 She was there. She locked herself in her room, which I don't blame her for and nobody knows what they would do in that situation. But there was nowhere for me to go. I'm mean I'm running into a little square room. So I fought. I fought, I fought, I fought. I screamed. I yelled. I kicked. I beat. I fought.

And you know, as sort of as quickly as it came on, he got up and left because he saw the five women that were sitting in the room where he followed me to. I didn't see them. So he knew people were going to call the police. And I didn't even know until the trial that there were other people in the room. That's how focused I was on just my life.

So those were very dark days.

Julie Roehm: 08:27 He left, so he turned around and left. And you're laying there?

Jennifer Gilbert: 08:30 I'm laying there. I was in complete shock. I mean, I hadn't shed a tear. I was very calm actually. And then I knocked on the door of my friend. She came out and I said, "Come out, he's gone." And she took one look at me and she's shrieking at the top of her lungs.

I mean, the one thing I do not remember at all is what I looked like. I have forgotten completely physically what I looked like. I can recall every minute of the attack, but not what I looked like. So she's just shrieking and I kind of did like, not a slap across the face, but sort of a like shake, like, stop, I need you to help me call the police. Call an ambulance. Call my parents, but don't tell them what happened.

And so then I just laid on the ground and I'd lost so much blood. So you know, the ambulance driver came and he's looking at me and he's like, "Hang on." I mean, it was a movie. He was like, "What's your name? Hold on, hold on, hang on, stay with me."

And I'm going down the hospital and it's like multiple stab wounds, stat, all these doctors. And it was just crazy. And I kept saying, "Keep it together, stay focused, stay focused." And they got me on the bed and I looked at the doctor and he said, "Where were you hit?" And I said, "Everywhere."

PART 1 OF 3 ENDS [00:10:04]

Jennifer Gilbert: 10:00 ... hit, and I said everywhere. And I told him, and then I looked at him and I said, "I'm going to go now." And out.

Speaker 3: 10:10 Really? And you just- Wow. You're 22 years old.

Jennifer Gilbert: 10:10 I was 22.

Speaker 3: 10:14 You're 22 years. I mean, just the calm and the composure in such a horrific situation. But I think in your book you go on to describe, that was then ...

Jennifer Gilbert: 10:25 Oh, it was really bad. Yeah.

Speaker 3: 10:26 But then the recovery, the trial.

Jennifer Gilbert: 10:31 The trial was three years later, because he actually was a paroled murderer, so he had to go back to jail for three years. So somewhere in my mind I heard three years, and when I decided, it was about six months later, that if I let this man make me deviate my life by a centimeter, then he may as well have killed me. And I kind of stood up, and that was one of the days that I was like, "You picked the wrong girl." And I was living in Boston at the time, which was strange, because I didn't know anybody in Boston. And I packed up my things and I went back to New York. And I was like, "Okay, that girl's gone. She doesn't exist any more. There's a new girl and she's going to be polished and smiley and strong and put on her red lipstick and fight the world." And I really just became that.

But the inside of me was thinking, "I can't believe this happened. I can't believe my life would turn on a dime," which does. And I thought, "I just need to be around people celebrating," because life is today. Life is the moment. And at the end of the day, truly, what do we have? We have our happiness, we have our joyous occasions. So I thought, "I need to be around people laughing and dancing and singing or communicating." And so I went to be a wedding planner. And that was not at all what I set out to do.

But I was like, "Well, who celebrates?" So unmarried, of course, became an event planner. But we did weddings at the company I was at.

Speaker 3: 12:19 So I talk about these "holy shit moments," these hoshimos, and you had, of everybody I've ever spoken to, one of the most extraordinary. But how you turned that into something positive and turned it into focusing on joy and lifting yourself up at such a young age, where I have to imagine the majority of people at that age would crumble and take a long time to actually feel like they were themselves, much less come out and be part of business and start something, or do something that was joyous. And you were able to do that.

Jennifer Gilbert: 12:55 I don't know where it comes from. I think it was the same resiliency that helped me save my life. Because when that happens, the police actually told me that only 7% of women fight back.

Speaker 3: 13:06 Really?

Jennifer Gilbert: 13:07 Seven. And I was on it, I was with it. But I think life is a choice, right? So in that situation, if you've got the lightness on one side and the darkness on the other, which one wins? The one you feed. So I was just not going to go to the dark place. So I started working for this company, and after about a year of doing the weddings and just knowing the vendors and getting accustomed to New York City, which I had never really lived in, I wanted to cultivate, and my boss wanted me to cultivate, a corporate market. So I said, "Okay, how?" And he gave me a phone book and he was like, "Well, figure it out." For the kids listening, that's an actual book. It was an actual book. There was no Google back then, right?

Speaker 3: 14:05 That is for sure.

Jennifer Gilbert: 14:06 So I thought, "Okay, well, who needs to plan things, and who's got money, and who has volume?" Because it actually takes as much to plan 25 people as it does 2,500. Logistics are a little different, but planning is still the same. So I started to call investment banks and law firms and accounting firms, and I kept hearing the same thing over and over, which was, first it was "Shame, honey, you just missed the '80s." I was like, "Yeah, I heard, that was reggae ..."

Speaker 3: 14:41 Ra-ra.

Jennifer Gilbert: 14:41 Yeah, the ra-ra. Then it was recession.

Speaker 3: 14:43 Especially In New York.

Jennifer Gilbert: 14:44 Yes. Yeah, for sure.

Speaker 3: 14:45 Yeah.

Jennifer Gilbert: 14:46 And they said, "We would love to hire you because I can't even leave my desk. We're so busy. But that's my job."

Speaker 3: 14:53 Yeah.

Jennifer Gilbert: 14:54 And I heard it over and over again. And I thought, "Well, if I'm going to corporate, there's somebody that does it already." A lot of the times it was an assistant or human resources. They weren't planners, but they were in charge of that. And so I would figure out ways to have my fee included in the budget. I would talk to the CEO and say, "Well, you're paying your executive assistant overtime. Whatever that amount is, plus some percentage of her everyday salary."

Speaker 3: 15:26 Yep.

Jennifer Gilbert: 15:26 So slowly, slowly, slowly I started to build up my following. Because back then there was no Internet, there was no AOL. If you wanted to find a space, you hoofed around. Literally, there was a little thing in the back of New York Magazine, and maybe four people advertised. It was a very fragmented industry, because your party could be at a hotel, a restaurant, a nightclub, a random loft. There were all these places and there were all these people, and they couldn't find each other. So after about a year and a half of really doing quite well, I was tripling my business from another company, I had another one of your sort of ...

Speaker 3: 15:26 Hoshimos?

Jennifer Gilbert: 16:16 Yeah, exactly. And I thought, "Wait, these people need venues and these venues need parties, and nobody is connecting them." And I said, "Well, they need a marketplace." And so I decided to flip the business model. And I was free to all these corporations, and I was supported by the venues, because they were thrilled to have me as a salesperson. So I was either on salary or they paid me a monthly stipend. And at first I would bring a $60,000 party to nightclub and they'd be like, "Here's $500, kid." I was like, "I think I've got to figure this out a little bit better." And by month four I had all of these venues calling saying, "How do I get on your list?" And I said, "You pay." And they said, "Okay." So I started my company that way. And then I went back, it was still sort of a hard sell, because when you say "free," people are like, "What's the catch?"

Speaker 3: 17:15 Yeah, right.

And that was like, "Well, I'm not not for profit. You just don't pay me." And so I talk about in my book a lot of my crazy cold calls sitting in people's office until they saw me, until I could explain what they did. And my first real client was Sallyan Zenko. And back then it was Salomon Brothers, and she was a tough nut to crack. But once I worked with her, I then got every single one of their Christmas parties. And then I would go to a different company.

Jennifer Gilbert: 17:47 Those are epic, the investment banking parties.

Speaker 3: 17:49 They were huge. And I did everybody, literally everybody. I would do $8 million of parties in December. It was crazy. And that's what happened. And all of a sudden I was like, I had five people, I had seven people, I had eight people, I had 12 people. I mean, it was just growing. And that was my business model. And so I really-

Jennifer Gilbert: 18:14 How old were you when you started that?

Speaker 3: 18:15 25.

Jennifer Gilbert: 18:16 You were 25 when you started that.

Speaker 3: 18:16 Yesterday.

Jennifer Gilbert: 18:18 Just yesterday.

Speaker 3: 18:20 Exactly. And I really revolutionized my business. And nobody had done this before, and I won the Ernst & Young award, and I thought, "No way." All these other companies had 200 employees. They had cyber somethings and security, and here I am fluffing flowers. It was hysterical. I just have to be the token woman. And I won because really, I needed no capital. I used the phone book.

Jennifer Gilbert: 18:53 No investors, right?

Speaker 3: 18:54 I had no investors. I had a lot of phones. Because I left and I went on my own.

Jennifer Gilbert: 19:00 Not cell phones. Or did you have the big ...

Speaker 3: 19:02 Oh no, I had the big ones.

Jennifer Gilbert: 19:03 Yeah, the bricks.

Speaker 3: 19:04 The big ones.

Jennifer Gilbert: 19:05 That came in their own little suitcase?

Speaker 3: 19:08 It was a little bit after that. It was like Nextel.

Jennifer Gilbert: 19:08 Okay.

Speaker 3: 19:09 They were big.

Jennifer Gilbert: 19:10 Okay.

Speaker 3: 19:11 And house phones, let's not forget.

Jennifer Gilbert: 19:12 Right.

Speaker 3: 19:13 And so I just started, and it grew from that. And then a couple years later I decided to scale, and I had offices in five cities.

Jennifer Gilbert: 19:24 Wow.

Speaker 3: 19:24 Yep.

Jennifer Gilbert: 19:24 Across the country?

Speaker 3: 19:25 Across the country. DC, New York, Chicago, LA, and San Francisco.

Jennifer Gilbert: 19:30 Wow.

Speaker 3: 19:31 I had employees everywhere and I was traveling all over, because it had to be my business model and my culture. And it's funny, then there was the dotcom, so things started happening there. And I laugh because I'm a data person, and so even though I'm not technical, I knew what I wanted, and I basically built my own Salesforce back then. There was no such tool. People were using an Excel spreadsheet. But I-

PART 2 OF 3 ENDS [00:20:04]

Jennifer Gilbert: 20:00 ... tool. People were using an Excel spreadsheet. But I customized a database, so that all my different offices could see-

Julie: 20:08 Could share?

Jennifer Gilbert: 20:08 Exactly. So let's say the president of Morgan Stanley only liked this kind of scotch. Wherever we did his event, he'd walk in the door and there's his scotch. Those little things are about hospitality.

Julie: 20:20 Oh my God, huge.

Jennifer Gilbert: 20:21 And it's taking care of people. For me, it's always about the guest's experience. So, we've just grown from there. Now, I do a lot on the vendor side. I'm consultant for how they should actually set up their space. While some construction, we're exclusive on a lot of venues that are opening because they call me and we become their sales force before they need to hire one person. So you know.

Julie: 20:52 So in this time frame, how old were you when you had those five offices? I mean, how many years-

Jennifer Gilbert: 20:59 Probably...

Julie: 21:00 Did it take five years?

Jennifer Gilbert: 21:02 It was probably around 31, 32, 33. Around there.

Julie: 21:07 So this is huge. And somewhere along this way, your personal life happens.

Jennifer Gilbert: 21:13 I went a different trajectory because I was not doing the dating thing.

Julie: 21:23 Yeah. When was that going to happen?

Jennifer Gilbert: 21:25 I never had like a "Hey, at the bar come home with me" because I would have to explain these scars, not that I would anyway, but I would have to explain all these scars. And so until I was really close to somebody and thought they would be around, I didn't have anyone come to my apartment. I didn't take my clothes off. So it was still new and so I really just focused on work and I felt while I was experiencing other people's joy, I really didn't think I would have my own.

Julie: 21:57 Creating your own.

Jennifer Gilbert: 21:58 And so I really had nothing to give. I had a lot of boyfriends at times, but inevitably it would end because I just, I couldn't do it. So I think it was like kind of through osmosis. I did get married and I did have my kids and things like that.

Julie: 22:24 So when did you have your first?

Jennifer Gilbert: 22:27 I got married right before I was 34. I actually married my absolute best friend, which while he's great guy, we are now not together because best friends are sort of best friends.

I had my daughter when I was 36. I had my twins when I was 39. It's not like your name is picked out of the bowl of bad things happened to you and then it goes into a different bowl of " You're done." It goes right back into the same bowl.

I had twin boys and by the age of two and a half to three, one of them was completely bald. He had alopecia and it started as areata, which is patches, but by three, no hair, eyelashes or eyebrows. So that was very shocking to me. It really took a lot for me to realize that while I had my before and after, he now had his before and after. All of these old feelings for me started to come up and all of these feelings of shame because believe me, if I could have controlled one hair on his head to grow, I would've found the place to do it, the person to take him to.

And really one day I realized that if I don't make this okay for him, it won't be.

Julie: 24:05 Right.

Jennifer Gilbert: 24:05 And the only reality that he has is my reality.

Julie: 24:08 Yeah.

Jennifer Gilbert: 24:09 So we learned about different and we learned in my house about empathy and compassion and kindness because we lived it and we still do. But I have a bracelet that says "Warrior" and I make my kids warriors in the kindest way. But I just won't have them going through life like, "Why me?"

Julie: 24:32 Right. Do they know about your story?

Jennifer Gilbert: 24:36 They know because I wrote a book.

Julie: 24:38 Right.

Jennifer Gilbert: 24:38 That Something bad happened to me. My 14 year old knows a little bit more and for them it was sort of like I was beaten up kind of thing.

Julie: 24:51 Right.

Jennifer Gilbert: 24:52 The guys in jail and the police did their job and the court system works. The judge put him in jail. Which did by the way to go to trial. And he was sentenced to 27 years for attempted murder.

Julie: 25:04 Wow.

Jennifer Gilbert: 25:04 So that was a victory.

Julie: 25:07 Peace of mind for you. I would think whether or not it sounded like he randomly chose you. It sounds like but still the thought that that's out there would be hard.

Jennifer Gilbert: 25:21 Well, you go through a lot of, "Why me?"

Julie: 25:23 Yeah, of course.

Jennifer Gilbert: 25:23 And that was a big question for a long time. Like, "Did I do something wrong? Did I look the wrong way? Did I sound wrong?" and here's my son and he asked me "Why me?"

And I say, "Why not you?"

Julie: 25:39 Yeah.

Jennifer Gilbert: 25:39 Bad things happen. It's who you are after they happen. That's your choice. And you rock the bald and you're beautiful and you're here to change this planet because you have changed my life. Because he got me to actually talk about what happened to me finally 20 years later.

Julie: 25:58 Really? It was because of him.

Jennifer Gilbert: 26:00 That was my book because I started to journal what was going on with him and then I realized, "Oh my God, so much of this is about me and I better snap out of it really quick."

Julie: 26:14 Yeah. So I have to imagine that because of your story that you've impacted, and your book's been out a while, that you've impacted many people's lives. Is there any one story of somebody who's reached out to you or who's come up to you that sticks out? Because I have to believe that-

Jennifer Gilbert: 26:39 I still get at least one, some weeks three, emails, texts, messages of someone who read my book. It's really funny because it was everywhere and then it went quiet and there's sort of this resurgence somehow. I don't know.

Julie: 26:57 Well, we're going to create a new one with this.

Jennifer Gilbert: 26:58 I hope so. Nice. People reach out and they tell me like I helped them. And because of what I did and because I chose the path that I did and it wasn't easy and this book is really raw, like there was control issues and eating issues and exercise issues because when you feel so out of control. I call it like the illusion of control. Which is event planning also. We plan, we plan, we plan but we don't have control. It can rain on your tents.

Julie: 27:28 Right.

Jennifer Gilbert: 27:29 So yeah.

Julie: 27:30 The flowers can come in. There's so many things.

Jennifer Gilbert: 27:34 I call myself the chief damage control officer.

Julie: 27:36 Of course. Right. Firefighter.

Jennifer Gilbert: 27:38 Yeah, exactly. But they all make me cry. I mean they really do.

Julie: 27:43 Every time?

Jennifer Gilbert: 27:44 Every time because the fact that people feel so much to reach out to me is beautiful and it really makes me feel good.

Julie: 27:53 It should, it should. And I hope everybody listening goes out and gets Jennifer Gilbert's book.

Jennifer Gilbert: 28:00 Yes.

Julie: 28:00 "I Never Promised You a Goodie Bag", but also look out for her new one that will be... When does your new one come out?

Jennifer Gilbert: 28:04 When I-

Julie: 28:05 Finish it?

Jennifer Gilbert: 28:05 Get it together. Yeah, exactly.

Julie: 28:08 So sooner or later we'll come back to that.

Jennifer Gilbert: 28:10 Exactly.

Julie: 28:10 Yeah. That's great. First of all, it's such a pleasure knowing you, you're such a force, but also just your bravery of telling the story.

I'm so glad that you are so open about it because you have the strength that it took for you to get through is now being passed on in spades.

Jennifer Gilbert: 28:33 I mean, I just think the lesson is you can't control what happens to you ever in this life as much as you want to, but you can control who you are after it happens.

Julie: 28:41 Yeah.

Jennifer Gilbert: 28:43 Anybody can pick themselves up and say like, "Enough, enough, I've got to move on."

Julie: 28:48 Right.

Jennifer Gilbert: 28:48 "I've got to forgive. I've got to let go." I used to think my power was in the fight.

Julie: 28:53 Yeah.

Jennifer Gilbert: 28:54 The power is in the surrender.

Julie: 28:58 Wow. That brings a tear to my eyes, so thank you. Thank you for coming and sharing this for me.

Jennifer Gilbert: 28:58 Thank you Julie for having me.

Julie: 29:04 This is wonderful.

Jennifer Gilbert: 29:05 All right. Thank you.

Julie: 29:06 Thanks.

PART 3 OF 3 ENDS [00:29:07]