The Boss Box with Hillary Gadsby

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TSP BE04 | The Boss Box

Episode Summary

TSP BE04 | The Boss BoxInstead of competing, team up and learn from and with each other. Hillary Gadsby’s success isn’t defined by how much money she has, it is the people in her circle who paints the most honest picture of who she is. As the founder of The Boss Box, Hillary aims to help women entrepreneurs by showcasing their products through collaborations and educating each other with the many facets of wellness, beauty and fashion. Have fun, be different and rock those stilettos like the boss you really are.

Today’s guest on The Successful Pitch is Hillary Gadsby. She is the Founder of Stiletto Gal and has a fascinating story about how she came up with that name. From there, has launched a company called The Boss Box which is a box that comes to female entrepreneurs with everything from mindset to usable tips on how to be a better business person. She’s really created something big and interesting here. She said, “If you help people to give them the tools to thrive, they will use those tools.” Her big question that we talked about is how do you define success? It’s much bigger than just money. She said, “When we’re all about collaborating versus competing, things really take off.” She said, “Be at peace, not in pieces.” She’s got something on there called Bossfidence, which is a play of confidence that I think you’ll really enjoy.

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The Boss Box with Hillary Gadsby


Today’s guest is Hillary Gadsby, a marketing dynamo whose international career spans the US, the UK, and France. Hillary is known for creating and producing outstanding and diverse events including a wide range of corporate events, public relations, corporate meetings, product launches, fashion shows, you name it. Her extensive experience in sales and marketing event management shows that she has gained recognition among some of the world’s best brands like Ralph Lauren, Gucci and Vera Wang. She’s been nominated as a Woman to Watch for 2016 Women of Influence Awards. I’m thrilled to have her today. Hillary, welcome to the show.

Thank you so much for having me, John.

It’s always interesting to me how people and women like you have their hands in so many different things. If you wouldn’t mind, would you take us back to your story of origin? You can go back as far as you want of when you were in college or before you went to college. Did you always know you wanted to do this?

Yes. My mother has always been an entrepreneur. Unfortunately, she’s failed miserably each time but she really was somebody who would pick herself back up and start over again. I’ve followed that in my life as well, in my business. I’m from Sun Valley, Idaho. It’s a prominent area. You know that you can charge a good amount of money for babysitting services and that’s what I did. I started out with one family and then it built up to several different families. I can’t be in the same place at one time so I recruited some girlfriends. I charged $20 an hour for my services. I gave my girlfriends $15 an hour. I created my little staffing company, if you will, at ten years old. I stopped doing that thing. I went into school and life happens.

TSP BE04 | The Boss Box

A Gadsby Affair: Strategic Marketing Solutions

Fast forward to 2008, I was working with a concierge firm in San Diego helping them to build their LA business. I was a consultant and I had one client who came in and wanted to do some client appreciation events. I had not really done anything entrepreneurial ever since my ten years old. This client was coming in. We haven’t signed the contract yet. It was an accounting firm and they wanted to do client appreciation events for their clients. We were working with this other firm and I decided that I was not going to continue with them. I called up the client who I had brought in and I said, “I’m not going to be working with this company anymore. I know you’re going to sign the contract, but I just wanted to let you know I won’t be there.” He said, “Hillary, the reason why I signed this contract was to work with you. I want your skills. I know you can do this. I want to work with you. Why don’t you just work with me instead?” That’s how A Gadsby Affair was born. Within a couple of seconds, I became a business owner. Within that weekend, I had a domain name. I had a logo. I had it all. Then I had to start pitching myself. I was lucky to start with this one client. He said, “We’re going to do one event with you and then we’ll see what happens.” We did the event and then he hired me for nine more.

You had the ultimate proof of concept there, didn’t you?

I did, definitely a big boost in my self-esteem there.

Also to prove to him and other people that you can deliver what you say you’re going to deliver, which is so important, the integrity. People want to know that they can trust you to do what you say you’re going to do. I see that time and again in successful entrepreneurs like you. You deliver, people trust you, then they give you more money for your startup or they give you more clients or more business. That repeat business is everything, isn’t it?

It is everything. That’s what I’ve actually built my company on, is the repeat business. It’s people referring me. I have never really done a lot of marketing in my company. It’s been more referrals through other clients. It’s been really, really lucrative. I’ve had some amazing clients like Four Seasons and Toyota and it’s because of the reputation that we’ve built over the years.

Now, you’ve got your hands in a couple of other things. Let’s talk about Stiletto Gal a little bit.

Stiletto Gal came about in 2012. Going back to when I started A Gadsby Affair, I didn’t really have any mentors. I’ve just started. I was like, “I’m going to fake it until I make it.” I called upon some people within my sphere, my circle who were men. I didn’t have any female mentors and female advisers. Stiletto Gal came about because not only do I want to create my own personal brand, which is all about confidence and women, and I was always known for the shoes that I wore. I came up with Stiletto Gal because it has nothing to do with shoes. It had to do about walking a mile in my shoes and doing the things that I did. I wanted to create something where women could look at the content and feel inspired by it and also to give them tools on what they need to do, “Here’s what I did wrong. Here’s what you can do right.” That’s how Stiletto Gal was born. It started out as a blog in 2012. It was all about a day in my life as a woman entrepreneur. I did it five days a week, which I’m sure a lot of bloggers know that five days a week blogging is a lot of work. People loved walked a mile in my shoes and then I created Walk a Mile in her shoes every Thursday where I featured another woman in business. I feel like learning from other women was a great platform for not only myself but others. In 2014, it turned into a Speaker Series called Secrets of Successful Woman Entrepreneurs where it was a fireside chat between myself and a woman entrepreneur. It started out with Toni Ko, the founder of NYX Cosmetics.

Don’t you find as a host you learn so much from your guests?

Yes. I want to write a book from the stuff that I learned from my guests.

I literally did. That’s so funny you said that. I took ten of my favorite podcasts and took the transcripts and turned it into a book. That’s another takeaway for everyone listening today, is there are all kinds of ways to repurpose your content.

I definitely want to write a book one day from the stuff that I’ve learned from the speaker series. One of the questions that I ask that’s so important is, how do you define success? A lot of the women do not say money. I love that because I don’t believe in that either. I don’t believe that success equals money. I believe that success equals happiness. I believe that success means the people you surround yourself with, the people who are in your circle, I believe that that’s where success comes from. It’s being well-known and having the integrity in your circle of friends and colleagues.

If you don’t enjoy the people you’re working with or the people you’re hanging out with, your life is miserable no matter how much money you have, is what I found. Unfortunately, seeing people like that in the media that you go, “Why are they so unhappy?” It’s because of one of the things you said. They’re not purposed. They don’t have integrity. Stiletto Gal led to The Boss Box. Is that correct?

Yes. I had always wanted to do a subscription box for women in business. At the time, I was like, “There’s nothing out there like this.” There’s the Birchboxes and the FabFitFuns, all these different subscription boxes for women but there wasn’t anything that provided some educational material or tools. We actually call it #ToolstoThrive. I found a couple of women on social media who were doing similar things. They wanted to empower women. They wanted to inspire them and give them the tools to do so. The first person I met was Shalini Vadhera. Shalini has Passport to Beauty, which is this global beauty brand. She took all kinds of ideas from beauty tips all around the world and creates her own product. She wrote a book, a best-selling book. She also has Power Beauty Living, which she launched on the floor of the UN a few years ago. It’s all about empowering women through their not only beauty but inside and then also their business.

She and I met on Instagram and we were just, “We have to meet. Let’s help each other.” That’s what Boss Box is about. It’s helping other women. It’s helping showcase other women’s products and not only that, it’s getting women to collaborate instead of compete. Shalini and I started that. It had a different name. The Boss Box popped into my head one day. It’s funny, a lot of things pop into my head daily that turn into great businesses. Stiletto Gal popped in my head as I was having coffee with a girlfriend. She said, “I like your stilettos.” That’s how it happened. Boss Box was the same way. Then, we brought in another partner about six months ago named Heidi Nazarudin. She’s The Ambitionista. She’s a lifestyle influencer in fashion and lifestyle and she’s building some really amazing brands. The three of us together wanted to just collaborate with each other and help as many women as we could. It’s a quarterly subscription box for women in business. Everything from leadership to education to wellness, mindfulness, fashion and beauty, all in one box every quarter.

[Tweet “Collaborate; don’t compete.”]

I also love that you’re connected with Dale Carnegie in doing this. That’s the mindset’s impart, yes?

Yes. The soft skills and the leadership skills are so important especially when you’re pitching yourself and how to do that effectively. We partnered with Los Angeles and Ventura County Dale Carnegie, and an amazing man named Brian Barry who’s a top coach there. He has been a friend of mine for many, many years. We’ve always wanted to work together. He’s always seen the stuff that I’ve done with my events and always really admired everything that we’re doing. I came up to him with this and he was, “I’m in.” We created The Boss Box Academy series with him. Every box has its own booklet, which is the lesson and then the workbook as well. You have to go back and do the lesson yourself on your business. Not only that, each one comes with a 60-minute online live coaching session with him.

That alone is worth the cost of the subscription.

He’s one of the most amazing coaches I’ve ever seen. We did a training a couple of weeks ago and it was just incredible.

I work with people all the time on their confidence before they get up to pitch to get a new client or to get funding for their startup. You have a really clever word that I have never seen, Bossfidence.

TSP BE04 | The Boss Box

That’s how Bossfidence was created. She is our case study for what we do.

Bossfidence is a brand that this lovely girl, Ashley Gibson, created. I’ve known her for a couple of years now. When I was doing my events with LA Business Journal, she worked for the LA Business Journal. I mentored here along the way. She started writing pieces for our Speaker Series. I thought she was a great writer. I said, “We’re building The Boss Box and we have and there’s going to be content on it. Why don’t we give you your own column?” That’s how Bossfidence was created. She is our case study for what we do. She has this whole brand and she’s doing well. She’s got 1,500 people following her so far. She’s only been doing it for a couple of months.

The one that really jumps out at me is be at peace not in pieces.

She’s brilliant when it comes to that stuff. I’m really proud of her. We’re excited to have her with The Boss Box.

It’s quite exciting to watch all of that happening. What is your strategy on getting people to subscribe to The Boss Box?

We’re lucky the three of us combined we have over a million followers on social media so that helps. I’m not going to say that that’s the only thing because I think it’s important that we get our faces out there too. I’ve done an event where there was a room of ten women. It was a small mastermind and I sold six boxes out with that. It’s really important for us to get in front of people because they have to see the passion. With social media, you could have so many followers but it’s also the engagement. Luckily, we do have the engagement and a lot of our subscribers come from Instagram. I think that you really have to have people who are ambassadors for you, really believe in the brand to get it out there. That’s really what sells is when people are saying, “I love this product. This is what has helped me do with the case studies that come from it.” That’s what sells a product.

Let’s hear one of your stories of who this is for and who this is not for. I think that’s always so helpful to have that down and very clear who your avatar is. If you wouldn’t mind sharing that, I think it will give people not only a great example of how to define their avatar, but also determine whether this is a good fit for them or not.

We have two target markets, which is interesting. We have 18 to 35, the millennial market. They may have a corporate job but they want a side hustle. They want to start their own business but they just don’t know how. We give them those tools. It’s also for a corporate executive who maybe wants to level up in their career, who’s stagnant right now. Not only does the educational materials help them, but also there’s really fun, inspirational items in each box that do that. With those two target markets are really who we target. People who are more established in their business, the entrepreneur who has maybe had an exit. That’s not for them.

You’re solving a problem for people who have an urge but don’t know how to do it and they stumble and fall without your guidance. The Boss Box is a clever way to get some inspiration, get some guidance and be part of a network. This is what I see is happening.

We have a network of around 15,000 between all of us. If you don’t subscribe to the box, you do have the network. You can come to our events, which are going to be launched later this year in other cities. Boss Talks will be launched in Dallas, in New York. We’re only in LA at the moment but later this year, we’re going to be launching in other cities. It’s really exciting. We’ll be inspiring women all over the country and giving them tools to thrive.

[Tweet “Be at peace, not in pieces.”]

I think it could be its own reality show in a way. I think this is really great stories. Speaking of stories, can you share a story of what it was like to work with either Ralph Lauren, Toyota or Four Seasons?

Ralph Lauren was quite an experience. I unfortunately had the experience during 9/11. I was in Paris. I worked for Ralph Lauren in Paris, which is really close to the American Embassy. It was so fun to work with them. I worked on the women’s side, the men’s side and the children’s brands. It was so fast-paced. These women were incredible. I was in the marketing and PR department. Every single day was different whether it was a product launch or PR press materials, anything like that. I had a really great time. I learned a lot. I would say, John, I learned a lot more from another brand that I worked with in luxury and it was the France Luxury Group. A gentleman by the name of Mounir Moufarrige is one of my mentors. He’s a man. He took Phoebe Philo to Chloé, Stella McCartney to Chloé. He’s all about making brands better; taking older brands and revamping them. I worked for him for about a year and watched everything he did. I did everything from marketing to PR to being his executive assistant to sales to watching dresses in haute couture being made from a sketch to putting beading on a dress. I learned from him what a brand is and not only what a brand is, how to make it different, how to stand out from anything else. In my business today, I use every skill that he gave me.

Can you share what are the secrets of how do we make our brand stand out?

You have to be different. With Stiletto Gal for example, I took a shoe and made women feel confident, “It makes me feel confident. Why can’t it make other women feel confident?” That doesn’t have to be wearing a stiletto. It could be wearing a flip-flop but what makes you feel confident. That’s one of the things that I can say is, you can take things that resonate with you and that gives you something different.

I love that because for me I’m known as The Pitch Whisperer, you’re known as the Stiletto Gal and now the founder of The Boss Box. When you have something catchy that people can remember more than your name or your company, I think it really helps get the sticky factor and the awareness up. Yes?

I agree, 100%.

If you had one piece of advice for our listeners about either branding or networking, what would it be?

TSP BE04 | The Boss Box

I would say for networking, meet as many people as you possibly can in your early stages of your business.

I would say for networking, meet as many people as you possibly can in your early stages of your business. One of the things that I did is I worked with a lot of financial services firms. That was my niche because of the CPA firm that I started with. I thought, “They definitely need some help. We need to get some return on investment. It’s all about bringing them new clients. Not just throwing an event, but giving them that return on investment.” I started going to accounting firm events, associations, business forums international where it’s all finance firms and networking with those people. It’s really important to network with the people who you want as your clients because that’s where you see the pain points. They’ll tell you what they need. It’s not about going to just random networking events where there’s all kinds of different people there, which is great. You want to build your Rolodex as fast as you possibly can. However, if you do more targeting and re-targeting of the people that you meet, you’ll go much further in business.

Have a laser focus of who you connect with so you’re not talking to people who are not in your sweet spot. Is that the essence of it?


Since you’ve been so successful producing so many events, what makes a good event in your mind?

There are a couple of things. I think a really good event needs to have education. I think that’s so important. What are you going to learn from it? What’s the takeaway? Great networking and then also, it’s got to look good. You’ve got to stand out. If you’re a brand and you want people to talk about you, you have to stand out.

That means investing in lighting, flowers, food and all of that stuff.

Not only that, investing in somebody like me who’s going to build an entire strategic marketing plan for you so that you can get business out of it instead of spending $400,000 on an event that doesn’t result in anything.

I imagine part of your strategy includes helping people get publicity out of it to keep it going. Yes?

Absolutely. I can tell you one of our clients Joiful. They are an on-demand wellness app. They started out as beauty and wellness. Now, they’ve gone into massage and we did two events for them. The first one was all about getting artists. Getting the artist, the hairstylist, the makeup artist, the massage therapist, and the aestheticians to get onto the app and be the artist on the app that you use. Then, the other one was the consumer one. For the artist one, they invited about 200 people to this event and we got 75 artists to sign up on the app that evening. It was really good for the first one. Then the second one, funny enough we brought on Heidi in Marque Media, my business partner on Boss Box. We wanted to have something that had a lot of influencers for the consumer launch. Heidi brought in 17 million hits in two days for the event.

What do you attribute that to? Having a really good hook?

Our event was incredible. What we did was we created these vignettes where you could see exactly the type of service that you were getting in the event. We had this really big 10×10 boxes with a landscape behind them. There were massage therapists doing massage, facialists doing facials, hair stylist doing hair and braids and curls, and then makeup artists so you could really see and feel and experience what it would be like to use the Joiful app.

What you just did there is you painted a picture for us with all those details. It almost makes you feel like you’re in the movie and that you created the cinematic experience for people way above what you would just think of in terms of an app for wellness and massage. It became something much, much bigger and that’s what you need to do when you’re pitching anything is paint a picture, get people in the story, and then you have the big wow effect that you consistently have. Congratulations. It’s thrilling to watch and see.

It was a lot of fun to produce as well. A lot of work but a lot of fun to produce and the results were incredible. The client loves us. I think it’s really important. I agree with you, John, that telling the story is probably one of not if the most important part of selling your brand.

Now with full circle to what we’d started off the episode with was how do you define success? You just gave a great example of it, all that great outcome and having fun.

[Tweet “How do you define success?”]How do you define success?

It’s really important to have fun. If you’re not having fun, you might as well not do it.

People can feel that energy at the event even looking at the pictures whether it was fun to be there or not. I think that’s contagious and that’s ultimately what people want is they want a feeling when they’re buying or trying any new product or service. There’s a feeling that you’re going to get. When you get The Boss Box, you’re going to feel, I imagine, that you’re not alone. That’s an a-ha moment right there because being an entrepreneur can be scary and lonely. If you got The Boss Box coming to you quarterly, you feel like, “There’s other people out there doing what I’m doing, cheering me on and I’ve got some real tools that I didn’t even know where to go to find them and they’re all here in one box. How wonderful.”

TSP BE04 | The Boss Box

That’s why we created it is really to show people that they’re not alone and we are here.

That’s why we created it is really to show people that they’re not alone and we are here. Our earlier subscribers in the first box, we give them access to us. I reached out to a couple of people on Instagram when we launched our first box and loved what they were doing. I reached out to them and I talked to them about The Boss Box and they bought it. This one young lady was on the training the other day and she said, “I didn’t even realize I needed this.” That was the nugget. That was it.

That’s my favorite definition of luxury. When I was calling on big brands like Banana Republic and Lexus, we always had conversations of luxury is giving someone something they need without even knowing they need it. For example, Lexus would allow your phone to ring and be connected to your music so the music volume would go down so you can hear your phone. “I didn’t know I needed that but that’s really great.” Banana Republic started putting phone charges in their flagship stores so that people could charge their phone while they’re shopping. That’s really nice and the sales went up because people kept shopping while they waited for their phone to fully charge. It just keeps going and going, doesn’t it?

It definitely does. I like that idea, it’s smart.

How can we follow you on Instagram, Twitter, all that great stuff? How can people sign up for The Boss Box? Tell us everything about knowing more about keeping in touch with you, Hillary.

Personally, you can go to all the social media Facebook, Twitter and Instagram as @TheStilettoGal. The Boss Box is @TheBossBoxOfficial on Twitter, Instagram and Facebook. If you want to buy the box at

Thank you so much for being such a great inspirational guest with amazing stories. Please, how many people have worked for Ralph Lauren in France no less? It’s just fantastic. Thanks again, Hillary.

Thank you, John.

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Tags: A Gadsby Affair, Bossfidence, Hillary Gadsby, John Livesay, sellingsecretsforfunding, Stiletto Gal, successful pitch, The Boss Box