Amy Hilliard

May 7, 2007
Posted in interviews
May 7, 2007 Terkel

We met up with Amy in her Southside Chicago loft, to hear her story of how she made a leap of faith from the security of Corporate America, to the exhilarating yet exhausting world of entrepreneurship. While we devoured the best pound cake known to man, the warm and collected Amy relived the events that led to her following her passion, and the opening of her business Comfort Cake®.

Pound cake is Amy’s favorite dessert, and she has been making it forever. She would bring it to neighborhood bake sales, family dinners, and dinner parties. Her pound cake became an instant favorite with guests, and the ongoing joke became that if Amy couldn’t make the party, then her cake would just have to take her place.

Through her twenty years of marketing experience with companies such as Pillsbury, Gillette, and L’Oreal, Amy could smell a business opportunity when there was one. And with the overwhelming positive response to her pound cake creations, the scent she smelt was stronger than her famous “Awesome Almond” cake fresh out of the oven.

“I’m a marketer by nature, and I said to myself if one more person tells me that I should put this on the market, I’m going to do it. So I brought my cake to a neighborhood block party, and this woman tasted it and turned to me and said “you have a million dollar idea.” I said to myself, that’s it, that was the last one, I’m going to do it. And that’s when I decided to take the plunge and go forward with the idea.”

While she had mentally made the decision to pursue her passion, the fact was that she was still at L’Oreal and spare time was something that was hard to come by. She was heading up a marketing department with twelve people and over a hundred SKU’s, yet still had the desire to open a business for herself and her family. To create the spare time, she hired a consultant to write the business plan, which proved to be much easier for her to edit the plan instead of write it.

The next step was to put a name to the company and its delicious product.

“At a dinner party one Christmas I brought a cake to a friends house, and a lot of my cakes have liquor glazes. Whether it was because I had done too much Christmas shopping that year or whatever, I guess I poured a little more liquor on the cake than usual. So when everyone was eating it they were asking what I put in the cake. They were like “Wow, this is a comfortable cake.” And they just kept saying that over and over, and again, my marketing nature kicked in and I thought to myself “Comfortable Cake. Comfort Cake. Comfort Cake! That’s it!” And that’s how it was born.”

While Amy was getting everything in order with Comfort Cake®, she was still at L’Oreal where she was faced with a career decision. She was given the opportunity to move up in the company by heading up the marketing for a certain division where she would continue to travel the world, grow with the products, and have the possibility of becoming president one day.

But Amy couldn’t do it. It quite simply wasn’t what she wanted to do. She was traveling too much as it was, she had two children at home, and figured that it was time to live her passion and not create new products for someone else. She said to herself that for once, she was going to launch a product for herself and her family and decided that now was the time to do it. So she resigned at the end of 2000, incorporated Comfort Cake® on February 15, 2001, and is celebrating her five year anniversary in 2006.

The first year of business proved to be a true test for Comfort Cake®. Through a prior business connection, Amy had established their first prospective customer in United Airlines, and Comfort Cake® proceeded to vigorously pursue this lead. They were given a proposal by United to have Comfort Cake® samples. The order sent Amy and her team scrambling to design a logo, find a kitchen to cook out of and produce samples of the delicious pound cake…all in a thirty day span!

Her team somehow threw everything together and pitched it all to United. United sampled some of her pound cake, and a few days later they phoned Amy to tell her they wanted Comfort Cake® to supply their deserts. As Amy learned United wanted 500,000 deserts over the phone, her high spirits and overwhelming excitement led her to accidentally hang up on her first customer without gathering any details to arrange the order! She quickly realized her mistake, hurriedly punched the digits back into her phone, and professionally worked out the necessary details. She was in business!

Now if we add up everything, you might be able to see where the story is headed. Amy started her business in early 2001, and booked United Airlines as a customer in the middle of 2001 for a substantial amount of orders. In August of 2001, Amy took a complete leap of faith by selling her home in order to gsin capital enough to produce the United deserts. She was unable to find a bank that would loan her money despite the enormous United order. And then, less than a month later, the United planes went down on September 11th.

Fearing the worst, Amy figured that the order would be cancelled for sure when she talked to United. And why wouldn’t they? They were dealing with the most drastic event of our time and fighting off financial troubles in a struggling economy. But the ironic part of the story here is that the name Amy created for her product at a Christmas party was also the saving grace for United. With such a frightening time for customers, United said that they thought it would be great to have her deserts on board because the word “comfort” on the box helped relieve the anxiety passengers faced when flying. They decided to not only keep her order, but to include the deserts on other flights as well. The experience taught Amy that nothing would phase her within the entrepreneurial adventure of Comfort Cake®, and that nothing is impossible.

Since 2001, Amy has led Comfort Cake® in the right direction. With the help of her longtime partner CJ, they have grown the business to handle the amount of high volume orders they receive while catering to their corporate clients, like United. The delicious taste of her cakes have garnered national attention from publications, ranging from Ebony to Entrepreneur. Also, the freedom of doing business for herself has allowed Amy to focus on the personal things that matter most, like raising her two children. Because Amy pursued her passion, it is safe to say that she found a “comfort in the cake”.

In her spare time, Amy often talks to students and offers guidance to those who wish to receive. Here is what she offered to us when we asked what she usually tells students:

“You are born knowing what your passion is, but you sometimes don’t recognize it. I tell anyone to look at what you love to do, that you would do for free….because those are the things that are inbred in your DNA that you should pursue. If you don’t like something and it irritates you, then that is your signal to do something about it. Take the time, don’t be so busy that you don’t know what you like. I think a lot of students today are so busy doing so many things that they don’t know what they truly like. They are doing things their parents like, or what their teachers want them to do, but we don’t spend enough time to figure out who you are, and finding what really thrills you.”


I had been making pound cake forever because it was my favorite desert.  I’d bring it to the family dinners, the bake sales, holidays, parties, I’d just bring the cake.  In fact, it got so bad that if I couldn’t come to the party, they’d ask that I’d send the cake.

I’m a marketer by nature, so I said to myself that if one more person tastes the cake and says I should put it on the market, then I would do it.  I brought cake to a neighborhood block party and this woman tasted it and said, ‘You have a million dollar idea.’  And that’s when I really decided to take the plunge and get started.

It took awhile because I was still working at L’Oreal at the time.  I was running a marketing department with 12 people and over 100 SKU’s.  I was doing work with new product development, so I didn’t have a lot of time.  But I knew I wanted to get it done, so I hired someone to write the business plan.  It was easier for me to edit the plan than write it. 

The business plan got written, and in 1999 when I had served my family all the Thanksgiving meals- I always cook Thanksgiving for 35 people every year- that was another signal to me to start doing this.  There were people from all over the country that wanted my cake. 

I got a book from Borders on writing a successful business plan.  That’s what I used as a template.  We just filled out the spaces that they gave us.

At another dinner party that Christmas, I was at a friend’s house and I brought a cake with a liquor glaze.  This particular Christmas I guess I did too much shopping and poured all this liquor in there.  When everyone was eating my cake, they were like, ‘What did you put in this cake? This is a comfortable cake!’  They kept saying that and they were getting tipsy.  We had been talking about what to call the business that night, and everyone kept saying that it was a comfortable cake.  My marketing side just kicked in and said comfortable cake.  Comfort cake.  Comfort Cake!  That’s it! 

I went home that night to the website the government has, where you can start the trademark process.  I didn’t have a complete business plan or a real product, but I knew that if I wanted to call it Comfort Cake, I’d have to get it trademarked.  It was available, and put $135 down on my Mastercard.  I went to and registered the domain that night.  That’s how it was born.

Over the next year I refined the business plan and then I had to make a decision because L’Oreal wanted me to handle the marketing for a combined company.  They wanted me to keep in consideration for President of L’Oreal.  They told me that I was in line for that.  They said, ‘Isn’t this exciting! You get to travel the world with our new products!’ 

I looked the President of L’Oreal in the eye and said, ‘Not really.  That’s not what I want to do.  I really can’t continue to do that.’  I had two children at home.  I was traveling too much as it was.  I just figured that at some point I would have to live my passion and not make new products for someone else.  I had done that already.  I had launched Light Rain Shampoo in the marketplace.  I had done some pretty big products. 

I just said, ‘For once, I’m going to launch a product for myself and for my family.  Now’s the time to do it.’  So I resigned to do it.  That was in the end of 2000.  We incorporated January 15th, 2001.  And became 5 years old this year.  Here we are.

I definitely took a leap of faith.  But getting it done.  I knew I didn’t want to bake out of my home.  I was interviewing bakeries and I called a friend of mine who worked at United Airlines because they’re located here.  I knew that if I wanted to do it in a big way, and I did want to do it in a big way because I have two children that I have to put through college as a single mother.  So I wasn’t trying to just do this for fun.  So I needed a good first customer, and I tried United Airlines.  Why not?

I got an interview with the buyer.  I said, I’m not ready to ship, but if I were, what would I need to do.  He told me how big the desert would have to be, and what the price range would be.  So I kept that in the back of my mind when I was ready to come back with a sales proposal.

Two weeks later he called me back.  He said, ‘We’re reviewing deserts in 30 days.  If you ever want to sell United in the next two years, you gotta bring samples down in 30 days.  Can you have samples down in 30 days?

I’m like, ‘Sure!  No problem!  I’ll have them there in 30 days!’  I didn’t have a bakery.  I was in the middle of doing the logo.  I just had my recipes, so I could make one cake, but I hadn’t commercialized them yet.  But, I felt that I had to try for that. 

So I was interviewing six bakeries at the time.  I went to them and said, ‘Look.  We have a chance to get some United business.  Who can get me samples in 30 days?  Because whoever can do it, you’re my guy.’

One guy was able to get it done.  I was able to complete the logo.  I was driving the graphics firm crazy because we had to get the presentation just right.  I ran it all out to United on a Monday.  They called me on a Tuesday to say they really liked my samples.

I’m like, ‘Great!  Do you need some more?  I can bring some more!  I can get in my truck and bring some more!  We’ve got lots of ‘em!’  They’re like, ‘Whoa whoa.  Slow down.  We really like your samples.  We want to buy 500,000 of them.’ 

That was my very first order.  So, was I scared?  I hung up on the buyer I was so scared.  I was like, ‘Thank you very much!’ Click.  Without any information about when they wanted them.  Nothing.  I was just like, ‘That’s great!  Thank you!’ And I hung up the phone.  I was like, ‘Oh my God!  I hung up the phone on the buyer!’  I couldn’t believe I did that so I called them back and got the deadline and everything.  So yeah, I was pretty scared.  But more excited than scared.  Because it was such a great opportunity that we had to make happen.

But what really got me concerned, was United and most big companies when you’re doing food at that level have check dates where they check your progress as you go to develop production samples.  They have a taste like the prototype to check and see if they’re getting what they think they’re buying. 

The bakery that was able to do the slices and the samples couldn’t get the production samples right.  I kept trying with them and they would give me stuff that was unacceptable to me.  I had to fire them before I ever ship United.

So I had to fire my first bakery.  I had this 500,000 piece order.  And I didn’t have a bakery to make it.  I was pretty scared.  But still, more excited than scared. 

I started talking to everyone I could find in the food business to find a bakery that could do this.  I saw the owner of Eli’s Cheesecake at a party and he put me in touch with this bakery in the suburbs.  When I got there and told them what I was doing, they told me it was no problem.  They treated me as if I was Mrs. Fields.  It was great.  I came back for my first tasting and they had poundcake to fill up the whole table.  They were terrific.

But then the order was due on October, 2001.  They got the production samples approved July 2001.  I sold my house in August 2001 because no bank would give a loan.  Even with the United order.  They said I had to ship the order before I got a loan.  So I had to sell my house in order to fund the company.  And then, we all know what happened on 9/11.  The United plane went down.  So I thought they were going to cancel the order. 

But they didn’t.  They had us on the long leg flights to Hawaii.  They said, ‘You know, with everything that’s going on with 9/11, having a product in the air that has the word ‘comfort’ is a good idea.  We’re going to keep you on board.  In fact, we want to extend you to our South American lines.’ 

This company that I was so pleased with had so much of their business in the airline industry that when we were shipping and getting ready to open our website for Thanksgiving of that year, I had 5,000 cakes being shipped from Tulsa to the bakery to make the cakes in.  The owner called me and said, ‘Don’t send those boxes just yet.  We’re having a little restructuring.’  I learned the lesson to always get to know other folks in the company that are actually doing the work. 

That Monday he called me and said that the bank wouldn’t refinance his loan, and that they were going out of business tomorrow.  At this point he had all my specialized recipes, my pans, and the bank was coming to seize their assets Tuesday at noon.  So I called my team around this table we’re sitting at now and said we have 5 minutes for a pity party.  We can all cry if we want to.  But after that we have to drive down and get our stuff.  We got a UHaul and drove out to the plant at 8am.  Me, I’m stuck in traffic and frantic.  It’s like 9:30 and I’m still stuck in traffic.  I called my operations guy and he told me not to worry because they were there, and everything was loaded into the truck. 

If the bank had come, they would have seized anybody’s assets that were on the property and we would have been out of business.  But we got our stuff out. 

One of their production guys referred me to a bakery down the road, and they saved our business.  We haven’t looked back since.

But what that taught me guys, is that when that happens early on in my business, there’s absolutely nothing that phases me now.  I don’t care if my biggest customer calls and says they’re going to cancel their order.  Which did happen, because I was selling cakes to Jewel’s, but the buyer had to cancel Comfort Cake because we were going too slow.  But I had a meeting with them, and that taught me to never fold.  Never. 

My advice to anyone trying to start a business is that you’re going to have those moments.  But don’t fold.  Anyone will tell you to just keep going and you’ll be able to find a way. 

We still count paperclips.  That’s the hardest thing for people trying to transition out of Corporate America.  If you can’t transition from all the systems and all the support at your fingertips to having nothing, you won’t make it.  For example, when your computer breaks down in corporate America, you just call the IT department and someone scurries down and fixes your computer.  Well, I’ve been sitting on the phone with Verizon for two hours today because I’m not getting emails to my phone.  And I can’t operate like that. 

It doesn’t bother me because I multitask as I’m on hold.  But if you can’t make that transition, you won’t make it as an entrepreneur.  You have to say, ‘That was Corporate America.  This is entrepreneurship.’  Two different things. 

I wouldn’t trade it for anything.  The ability that I have to set my own course, to work with great people I chose who have the spirit of this company in mind, that’s worth it’s weight in gold.  CJ has been with me for 12 years, even in my corporate life.  She came and worked with me for six months at no salary when we started Comfort Cake.  You don’t get that in Corporate America.  You get some very good things.  I was able to do some terrific things and have some great teachers while I was there.  But if you have that maverick streak in you, it’s always going to be there.  You’re going to bump up against those rules and regulations and you’re going to think you can do things better.

Nothing is impossible.  So much is how you think about things.  If you think in terms of ‘I can’t do it.’  All that will come up in your mind are the things that you can’t do. If you think of what you can do, possibilities will show up.  Everything that you focus on has that impact. 

The slogan for our company is ‘Pound cake so good it feels like a hug.’  That’s worked very well for us.  My daughter created that when she was 14.  These are the things that keep me going.

I did my undergraduate at Howard, and my graduate degree at Harvard. 

I tell students and I’ll tell anyone this.  You’re born knowing what your passion is, but you sometimes don’t recognize it.  I tell anyone to look at what you love to do, that you would do for free, and look at what you don’t like.  What irritates you?  Because those are the two things that are inbreed in your DNA to pursue.  What you love is a no brainer, and you should go in that direction.  If you don’t like something and it irritates you, then that’s a signal to do something about it.  If something really gets on your nerves and you’re like, ‘Why do people have to call the airlines instead of making airline reservations online?  That is so stupid!  I rather make my airline reservations online.’  Well, somebody had that business idea.

I tell students to take the time, to not be so busy, that you don’t know what you like.  A lot of students are so busy today that they don’t know what they like.  They’re doing what their parents want them to do, what their teachers want.  We don’t spend enough time walking around saying ‘Who am I?  What thrills me?  That’s very, very important.  So take the time to understand what you like and let no one tell you that it’s wrong.  Because it’s not wrong.  It’s who you are.