When we first started Gilt Groupe, our invitation-only website that sells luxury fashion at a steep discount, I turned to my co-founder Alexis Maybank, and said, “What do you think the office dress code should be?”

Alexis, a Silicon Valley professional in a pencil skirt, had come from eBay and AOL, where she assured me she had never had to follow an office dress code. I’d come from Louis Vuitton where I wore interlocking LV’s from heel to handbag and while on a stint at Bulgari only wore their (very nice) jewelry and watches.

We decided not to enforce a dress code at our New York HQ and if there was a fashion emergency down the road, we would deal with it then.

As Gilt Groupe has grown to a 200+ person firm we adore the personal style of every employee. And just like high school there are fashion cliques.

The blokes in our warehouse in the Brooklyn Navy Yard are the coolest distribution guys in Kidrobot tees and John Varvatos jackets, of course, all bought on Gilt.

Our creative director Leah Park arrives at work in white Converse sneakers and like Wonder Woman pulls a pair of strappy silver Manolo Blahnik’s out from under her desk and she’s suddenly a show-stopping, iMac-clicking genius and fashion plate.

And our fashion buyers are a perilously on-trend gaggle who not only make the best deals in the business they own their style — in micro minis, swinging tops and layers of Vera Wang jewels.

But it’s the engineers who deserve a special shout out. The first time I met the brains who built our Gilt Groupe website I was wearing a Christian Lacroix three-quarter length jacket, sublimely-tailored Alvin Valley pants and ridiculously high Louis Vuitton platform shoes. To be honest, I think they were slightly aghast.

But now I feel they’re accustomed to their new fashionable milieu. Our engineers arrive at orientation in denims and, horror of horrors, comfortable-looking shoes and within a few Red Bull-fueled months they’re decked in Dolce & Gabbana. They can also spot a crimson Christian Louboutin sole at a hundred paces. I challenge any other IT department to do the same!

It was at the Gilt Halloween party last Fall that I realized that the whole dress code kerfuffle would just crush our nimble worker’s creativity. One of our key executives came as a realistic Karl Lagerfeld, we had two perfect John Gallianos and a buyer as a convincing Coco Channel.

It takes a lot of fashion irregulars to make the business world tick, but gosh, I love working in it. Did I mention while typing this I’m wearing a Gilt-sourced, shoulder-bearing silk chiffon Milly dress with a peppermint and coral paisley print? Of course, I got this frock from work. Talk about business with benefits.

In just one short year, we have seen NYC shift from a city of “keeping up with the Joneses” to one focused on “outsaving the Joneses.” Now what does this mean? We have started to see a sea change in behavior.

Instead of comparing weekend homes, vacation destinations or slapping down the Black Amex, New Yorkers are now making “saving” a game of one-upmanship. Out with conspicuous consumption in with conspicuous savings. We of course have no anthropological proof of this trend, however it is something we are witnessing more often when out to dinner with friends or in conversations with work colleagues.

It is neither gauche to compare deals obtained on a new dress, nor is insider savings through, say, cardholder benefits taboo to mention in polite conversation. Instead, people point to their “Staycations” in place of former far-flung vacations and to practical vehicles purchased instead of to a husband’s new Maserati. To show one’s savviness in savings is to show your intelligence and general shrewdness.

Some might say we experience this so often because of our role in starting an online fashion sales site, Gilt Groupe, focused on extending our members designer fashion at insider prices (up to 70 percent off). And yes, our members do flock to us in the interest of showing us a new dress, a pair of earrings or work suit they purchased at a great price. They proudly display purchases on our site and are quick to mention the price point with a sense of satisfaction.

However we have personally witnessed this new behavior outside of work: amongst friends and family members. We do think that this general shift in behavior signals a new culture of saving in New York and nationally. There is self-assurance and a sense of “winning” when obtaining value that suggests the intelligent and in-the-know consumer… saves! This makes sense given Goldman Sach’s recent prediction that “the national unemployment rate will reach 9 percent by end of 2009, and could continue rising into 2010.” While times are certainly tough nationally, especially here in NYC, Gothamites are trying to promote their savviness in savings — and we think they are intelligent for doing so. To miss this trend as a company or marketer is to be out of touch with the times.

From our vantage point at Gilt Groupe, people are stampeding online for our insider deals. And even though they are saving, and proudly so, they are still spending… And spending a lot! They spend, however, in a way that shows they are not willing pay for the overhead that comes with the prices at retail stores any longer. They spend not wanting to leave a store with three bags in each hand a la Sex and the City. And they spend, as long as in their spending, they are obtaining savings. Counterintuitive, but we think this new era of obtaining value in shopping is with us for at least another three years. We would love to hear your read on the topic. Are you seeing what we are seeing?

It is not every day that one gets to start up a business with a close friend of 14(+) years. Over the past 18 months, our start-up has grown from a small room of six people to a booming office of 200+ and counting. We have put in much of our own blood, sweat and tears into what has truly become an experience of a lifetime for us both. Here’s a glimpse of where this wild ride all began and where we are today…

October 31st, 2007, Halloween night-

The evening before our official November 1st launch… We were a small but determined team of six people wholly dedicated to successfully launching our start up concept of Gilt Groupe. Our amazing engineers each pulled an all-nighter to make final tweaks to the code for our site before we would officially blast invitations across the country.

November 1st, 2007, Gilt Groupe’s membership launch-

Show time. Over the course of the day, we sent out invitations to join Gilt Groupe to every single person we had ever met. Several tens of thousands of emails left our servers to sprinkle inboxes (and unfortunately spam filters) of potential Gilt Groupe customers throughout the United States. We were aiming to create a viral business model, but it depended on getting an initial critical mass of loyal style mavens to become members of our company. We thought that once they joined and hopefully quickly became obsessed with Gilt Groupe, they would in turn spread the word to all of their nearest and dearest.

Fortunately, our friends — fashionable, highly educated and tech savvy — were the perfect demographic for Gilt Groupe, so it took almost no convincing to get them to join our website as members… membership was free… We promised to find our Gilt Groupies the very best brands, for unbeatable prices. Our platform also removed all of the stress of NY sample sale shopping. No lines… No getting strip searched… No crazy women grabbing shoes out of your hands… No sneaking out of work and faking a doctor’s appointment. No being forced to pay with cash and running frantically to ATMs across the garment center… No nastiness… No damaged or shopworn merchandise… why wouldn’t someone join Gilt Groupe?

November 13th, 2007, Gilt Groupe’s first sale-

Zac Posen was our first sale on our site. We were so nervous. Would anyone buy anything? Even more important, would anyone visit the site during our 36 hour timeframe? In the 13 days that we ran our membership launch, we amassed approximately 15,000 registered Gilt Groupe members. Between the two of us, we knew almost all of these people — they were our friends and the friends of our friends. We thought 9am seemed like a good start time for the sale because a lot of our NY friends would just be arriving in the office and could probably do some online browsing before their days got hectic. However, we didn’t think about the West Coast… 6am over there. Painfully early! The morning of the sale, we were positioned to act as customer service. We did not know if our phones would be ringing off of the hook with questions from our members. Or perhaps our members would email us with their specific questions. Does a dress run particularly small? From what season was the merchandise? What if a top didn’t fit, could it be returned? Was the product authentic? We were intimately familiar with the product since together we had hand-selected it in Zac Posen’s showroom.

As the sale went live, our engineers noticed a traffic spike on our site. Lo and behold, sales began to trickle in… Our first purchase was from state of Missouri! We were puzzled. How did someone on Missouri hear about us? Neither of us knew anyone there. It was our first sign that viral marketing works. Our next order came from zip code 90210. It was 6:05am in Beverly Hills! We couldn’t believe that someone in California had woken up so early to shop from our site. The concept was working and after 8 hours, the Zac Posen sale sold out and we were elated.

Today, 18 months later, we have truly experienced hyper growth during a time that has been trying for many businesses and we are so gratified to have been a part of every single step of the process. We changed our start of sale time to 12pm EST, friendlier for the West Coast. We now offer our members over 25 sales per week. We have over 1 million members in the US. We launched our business in Japan in February 2009. Our warehouse space has expanded from one small room to three bustling studios that are in constant use. It’s gratifying to see how far we’ve come and thrilling to think how we will grow. Stay tuned for updates on our adventures, challenges and continued growth.

My mother died because she didn’t have health insurance. She was in her late fifties when all six of us grown kids were told that she had gone to the emergency room in extreme pain. The doctors and nurses didn’t even need to test her blood or run a scan to diagnose her. They took one look at Lupe’s yellowing eyes, one touch of her distended belly that she’d hid from us with bulky clothes and they made the correct diagnosis: fatal colon cancer. We all had the same questions we wanted answered right away: Why had she waited until tumors had grown into every organ? Why did she wait until she’d started wasting away, telling us that she just didn’t feel like eating, chalking it up to her divorce from our father? We had no idea what kind of pain she was in by the time she was diagnosed with stage-four colon cancer. What sane person would not go to the doctor with her symptoms and suffering? A person who knew that going to the doctor costs money. Money that we found out she didn’t have.

My Dominican-American mother was good at keeping secrets. At the time, about eight years ago, she had had just finished divorcing her second husband, our father, with whom she’d had a relationship with for over 30 years. I was the product of their affair before she’d divorced her first husband, Peter Wong, a secret she kept from everyone, including me, until death came knocking. So what do husbands have to do with health insurance? Well, in her divorce, she was able to stay on our father’s medical coverage, which is normal. However, in another secret act, Lupe decided — probably in a fit of loneliness and a quest for financial stability — to re-marry a third time, to an old family friend. She told us afterwards. And no, even though he was a business-owner for fifty-years, her third husband did not have health insurance — a typical scenario in the immigrant community. No matter, because they divorced a few months later (my mother had become too ‘American’ for his old-fashioned Latin needs) leaving my mother without medical coverage for the first time in almost 30 years.

Little did we know that Lupe had also gotten herself into substantial credit card debt. The mother of a personal finance expert wouldn’t allow her daughter even a peek into her money. She knew better because she was the parent, of course. Her independent, guarded streak lead to common scenarios growing up like coming home from college discovering Lupe’s eyes taped shut, leaving us kids incredulous that she didn’t tell any of us that she was having cataract surgery until the bandages gave it away. Nope. We’d just worry. Don’t worry.

Now we were worried. A very preventable cancer was set to kill our mother in four months or less. She had had a ticking time bomb eating away at her body, causing symptoms that would have brought any of us to the doctor, but she didn’t go because it would have put her more into debt. How many other Americans are in this position? How much less would it have cost the system for her to have a colonoscopy when she was at stage one or two, or even stage three which they found the same year in her younger sister, our aunt, who survived? Fear of cost, especially for those who don’t qualify for Medicaid, prevents too many of us from seeking the care we need to keep us not only alive, but well. We know that prevention pays off. In the debate over health care, I want to hear louder the cry of those who understand that we all need preventative care paid for in order to save the system billions and to make it work.

In the end, my mother did qualify for Medicaid, especially since she was too sick to work. And not only was she incredibly well taken care of (thank you state of New Hampshire and St. Joseph’s Hospital in Nashua) but her doctor had the foresight and thoughtfulness to get her access to free clinical trials of a cancer-drug that kept her alive, not for the mere months that the emergency room gave her, but for two long and grateful years.

How much longer would our mother, our children’s grandmother, have been with us if she had health insurance? Guadalupe Altagracias Giannotti was sixty years old.

I learned my deepest lessons about money as a kid. Our family of eight did OK, but we struggled to make it through several recessions. We went from what seemed like flush times, when all eight of us would dress up on Sunday nights to try the new restaurant in town, to what seemed like overnight taking donations from our church for Thanksgiving dinner.

By my teens, post-1987 market crash, I carried with me some young, hard-earned, hard-learned wisdom when it comes to money: It’s no fun to have your quality of life determined by something so outside of your control. I learned that if you lived too large when times were good, you lost out on the chance to be the ‘ant’ rather than the ‘grasshopper’ when the winter of a recession comes. I decided early on that I’d rather make sacrifices to live a smaller, more moderate life than risk my financial future on living it up when times were good and then letting an economy completely determine my fate when times were bad.

Granted, there’s a limit to what we have control over when it comes to life and money, and I’ve taken on some major risks that have thankfully paid off, such as loading up on student loans to get through graduate school. But I took advantage of a gift to see the patterns in life (and the economy) and realize how it’s not how much money you have or make, but what you do with it that determines the life you lead.

I’m thrilled to have a platform to share hundreds of stories and questions in times like these and to hopefully spread the word on the importance of taking control of your money. But my true fear is this: Have we really learned our lesson as a nation? Will we forget all this when times get good again?

When the market shot past 13,000 points, I was filled with anxiety while others celebrated. I knew what was coming. My book editors told me I was too conservative. That there was nothing wrong with spending more than 40% of your take-home income on a mortgage. I held my ground (it’s no more than 30% and that includes taxes and insurance). And I still do. Because everything is cyclical. So as we start to recover in 2009, take all these lessons and tips and changes in how you spend and save to heart, no matter what lenders, Wall St. or credit card companies say. It’s the difference between surviving and thriving.

What if … we focused on and appreciated “the good” in people instead of looking for and magnifying “the bad”?

I know, I know, we have all done this at one time or another but some, well, let’s be honest, many, do it all the time. Unfortunately I believe, as a culture, we are more conditioned to see what’s “wrong” in people (and circumstances) than what’s “right”. It can definitely be considered a social disease.

This weekend I was sitting outside with a group of my friends enjoying the amazing weather and one of them, a relationship expert for a hit TV show, was telling us why he believes so many relationships fail or never even get started. The first thing he said was, “Everyone is so focused on finding the faults in other people that they can’t even see or appreciate all the positive qualities a person may have.” Sadly, I agree with him, hence the inspiration for this article. But this goes well beyond the intimate relationships he was referring to and extends into every relationship of our lives; most importantly the relationship that begins with ourselves.

Let’s seriously think about how just this one behavioral change or paradigm shift could positively impact the world around us. I believe it could instantly spawn a higher sense of internal happiness and fulfillment and definitely increase the positive affect relationships have on our lives. The domino effect from that could be increased productivity, self-worth, self-esteem and willingness to take risks and pursue our desires. Additionally, the gratification that we would get from spending time with the people around us would add so much more value to our lives that we would seek it less from material validation.

Think about how you feel when someone compliments you. It makes you feel empowered and proud; it probably increases your confidence too. So imagine if we personally committed to looking for all the positive qualities in others around us and even complimented them on it. What impact could that have? How many lives could you positively affect each day?

If you understand the effects of positive reinforcement and the evidence that surrounds it, imagine what would happen if we applied that to our own lives and how we interact with others. Wouldn’t we then be able help others see the good in themselves? And by complimenting we could reinforce, therefore encourage the continued behavior. For example, if someone does something thoughtful and you compliment him or her on it, doesn’t that encourage more thoughtful behavior, which then equally discourages selfish behavior?

So why do we do it? I don’t think there is one answer here but I would definitely say some of the top factors are bad habits becoming acceptable behavior, ignorance, fear of vulnerability and lack of confidence. I am by no means asking people to be naïve or trusting of people who may not be trustworthy, but simply suggesting to shift the focus and see what happens.

I am very fortunate to have many wonderful friends who have conditioned themselves to see the positive in people and situations (for the most part, no one is “perfect”) that sometimes I forget how much of an epidemic this is. But after discussing it this weekend I couldn’t stop thinking, “What if … we all became more aware of how we should appreciate people and chose to focus more on their great qualities instead of finding “what’s wrong” … what a game changer that could be; independently to globally.

So, why not try it, if even for a day?

One of my mantras is “Do not judge; be inspired.” Judgment is part of human nature. But instead, it makes more sense to stop and be mindful of the way something works or is built and ask, “Why is it this way? Does it have to be?” Mindfulness comes when you just observe things in the moment. It’s an incredible tool. I try to practice mindfulness everyday–stepping out of flow of what I’m doing for a brief time and just being in the moment, appreciating what’s going on around me. When you can do that, you can see in a new way. Mindfulness creates fertile ground for inspiration. You become inspired to change things.

How many products, companies, and industries have started because someone saw past the judgement of a problem or an obstacle and had the audacity to say, “Can’t we do this differently?”

When you are inspired everything becomes possible and passion becomes your fuel. It is a powerful state of mind to be in. However, if you are stuck in harsh judgment, you are shutting off possibilities around you.

The next time you are about to “judge” something, catch yourself and say, “What can I learn from this?” Committing to be more mindful can be the simple habit that changes your life.

To find out more, check out my new book What if? & Why not?: How to Transform Your Fears Into Action and Start the Business of Your Dreams

Entrepreneurship is not about business. It is about self-transformation. It is about becoming who you have always wanted to be. It is a 180-degree shift in perspective and mind-set — then living everyday in that mindset. You stare at yourself everyday, see your weaknesses close up, and find new ways to overcome them. If you’re approaching entrepreneurship correctly, it is transformative. As an entrepreneur, you should be in a constant state of personal growth. Launching yourself out into space with nothing but a wing, a prayer, an idea and a business plan. Being this far outside your comfort zone, will change who you are and how you live more completely than any self-help program, religious conversion, or psychotherapy.

One day I would love to poll entrepreneurs who fall into two groups: the wildly successful and the ones who gave up after a short while. I’ll bet you that 90 percent of the wildly successful ones spent more time working on themselves than their companies. They have cultivated their passion, their self-belief and their ability to inspire others everyday. They spend less time working on balance sheets and fine-tuning marketing plans and more time finding new ways to overcome their fears and bring audacious new ideas to light. That’s what entrepreneurs do: they change the world by changing themselves first.

Ideas aren’t just about product development or financial success; they are part of your identity. You show the world who you are through expression and development of your ideas. When I talk to aspiring entrepreneurs who never got their idea off the drawing board, I hear the same sad story: it’s not the idea they don’t believe in, but their own ability to make it work. They don’t believe they have what it takes to be a Tommy Hilfiger or a Jeff Bezos or a Mark Zuckerberg, the college kid who created Facebook. But do you know the only quality separating these moguls from other people? Self-belief and the willingness to shove the fear back in the corners of their minds and trust their ideas.

The first question to ask yourself when you think about taking the entrepreneurial leap isn’t “What kind of business do I want to start?”, it’s “Who do I want to become?” The first thing you must change before you can realize your dream is yourself. Call it the spiritual path to entrepreneurship if you like, but ask anyone who has built something great from nothing and he or she will back me up. When you start there, everything else falls into place.

To find out more, check out my new book What if? & Why not?: How to Transform Your Fears Into Action and Start the Business of Your Dreams

Once you work at overcoming self-doubt and the fear of failure it gets easier to take action to bring your entrepreneurial dream to life which can also lead to many other personal dreams coming to life as well, because starting a business is about more than making a living. It’s about the fulfillment of your creative spirit and personal vision. It’s about pushing yourself constantly to live up to your full potential. That’s why the hardest part of getting started and sustaining your business is overcoming your own thinking. Yes, there are external challenges when you’re trying to start a business: funding, competition, product development, hiring, and so on. But what really matters is whether you believe you have the ability to face and overcome those challenges. Until you can jump over your inner roadblocks, the outer ones will stay firmly in place.

Overcoming your inner obstacles is about learning to rethink
the fearful thoughts that can lead you to quit before you start. It’s
about changing your mind-set. This is the crucial tipping point that
will allow you to unlock the door to what you deserve. I have found
that many people don’t pursue their dreams because they don’t feel
that they deserve them. But what if you do? As Penn State football
coach Joe Paterno says, “Believe deep down in your heart that you
are destined to do great things.” I believe we all are–that each and
every one of us has a special purpose and meaning.

For example, one day a woman told me that she wanted to open
her own boutique, and she wanted to ask me a few questions about
getting started. She said it had been her dream since she was a little
girl. She was now forty-eight, her kids were grown and in college,
and time was no longer an excuse. I listened to her story, and it was
like so many others I’ve heard: excuse after excuse–not enough
time, not enough money, not enough connections.

I have heard this story so many times that I was frustrated.
So when this woman finished, I simply said, “What if you could
do it? What if it became the most successful boutique in the area?
What if you won awards? What if you could impact the community
in ways you never imagined?” I kept going for a minute, and the
woman’s eyes got bigger and bigger. She was clearly thinking, “I
never thought of it that way before.” We are programmed to look at
the “everything that could go wrong” side of our dreams, and we’re
told that to look at the “everything could go right” scenario is naïve
and childish. Maybe too idealistic. I beg to differ.

In my journey, one of my greatest strengths has been my ability to rethink
my fears and doubts by asking two huge questions: “What if?” “Why not?”
“What if?” and “Why not?” are powerful questions in
my universe. They empower me by reminding me to embrace the
“everything could go right” scenario and to imagine all the great
possibilities.

I remember when I developed my habit of asking these questions
into a strategic tool. When I was launching the Butler Bag Company,
everyone in the industry told me that my concept wouldn’t work.
The first few times I sat in meetings and heard the doubts, I became
defensive. That only prompted others to defend their points of view,
which got us nowhere. One day, I was sitting in yet another meeting
with people questioning my ideas and telling me what I couldn’t do.
Finally, I realized that I needed to stop defending myself. Instead, I
asked, “What if my idea does work? What if it redefines the indus-
try and you had a chance to be a part of it and chose not to?” The
change was stunning. The person sitting across the table from me
was no longer defensive. He stopped and gave serious thought to
what I had said. The power was all flowing toward me, allowing
new perspectives to emerge. This changed everything.

When you start asking these kinds of “What if?” and “Why not?”
questions, you rethink your fears. You turn them into potential and
then into reality. Today, when someone says, “Jen, that’s crazy,” I
think, “Fantastic! I must be on to something!” Original thinking is
always ridiculed until it becomes accepted wisdom.

Try it now. Make it a habit. Every time you start to flood your mind with thoughts of self-doubt or some else does it to you, hit the mental reset button and begin thinking of all the great possibilities and potential. Then put your ideas into action to pursue your dreams.

I was approached recently by a woman anxious to pursue her childhood dream of opening up her own boutique. At 48 and with her kids now out of the house, she sensed that her opportunity had finally arrived but wasn’t sure where exactly to begin. She, like most who want to start a business, was feeling very trepidacious about taking those first crucial steps. So, I asked her to fill me in on the whole story of her vision in the hopes of getting a clearer idea of how my experience may help.

As someone who gets asked about this subject often, it came as no surprise to me that her explanation was laden with self-doubt and excuses – not enough time, not enough money, no connections, etc… In fact, she had already set herself up to fail before she we were even two minutes into the conversation. It was at that point I stopped her and began the reprogramming that would be necessary if she was ever going to see her dream through.

“What if you could do it?” I asked. “What if it became the most successful boutique in the area? What if you won awards? What if you could impact the community in ways you never imagined?”

This clearly caught her off-guard but as I continued this line of questioning, I could see her eyes begin to brighten up and a new energy fill her aura. She clearly had never thought this way and was turning a corner from the “focus on the negative and everything that could go wrong” mentality.

Unfortunately this sort of failure mindset is all too common these days. Too many have been programmed to immediately identify why we shouldn’t follow our passions instead of first considering all the happiness and vitality that doing so would bring. Overcoming our own limits in thinking and redefining the way we look at success has been the first and most profound step that many of us had had (and will have) to take.

Starting a business is about much more than making a living. It’s about pushing yourself to constantly live up to your potential in order to fulfill your creative spirit and personal vision. Of course there will always be external challenges when starting (and maintaining) a business: funding, competition, product development, hiring and so on. But what really matters is whether you believe you have the ability to face and overcome those challenges. Until you can jump over your inner roadblocks, the outer ones will stay firmly in place.

In my journey, my greatest asset has been teaching myself to rethink my fears and doubts by asking two huge questions: “What If?” and “Why Not?”

“What If?” and “Why Not?” are powerful questions in my universe. They empower me by reminding me to embrace the “everything could go right” scenario and to imagine all the great possibilities. When you start asking “What If?” and “Why Not?” you’re forced to confront, rethink, and reframe your fears; turning them into potential and then into reality. For example, if you’ve been feeling intimidated by the idea of all the hard work that goes into starting your own business, ask yourself, “What if working hard and having fun were the same thing?” (That’s the wonderful secret of entrepreneurship that no one tells you, by the way: when you’re doing something you love, even if you’re working longer hours than ever, you’ll never get tired because you’re doing what you love.)

So, why not add these two simple questions to your inner vernacular?

What if it led you to discover passion and success in not just business but every aspect of your life?