Heidi Carey: “Humility and humor”

Humility and humor. Let’s remember how small we really are as a way to release some of the pressure we will be under while starting up our business. Zoom out when you’re incredibly stressed: Remember life is very short, and we are a small part of a much bigger whole. Have fun, and laugh at […]

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Humility and humor. Let’s remember how small we really are as a way to release some of the pressure we will be under while starting up our business. Zoom out when you’re incredibly stressed: Remember life is very short, and we are a small part of a much bigger whole. Have fun, and laugh at yourself for taking it so seriously. Today is all we have.


Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles.

Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup?

In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experience about what it takes to create a highly successful startup.

I had the pleasure of interviewing Heidi Carey.

Heidi Carey grew up in Long Island and attended Barnard College in New York. She worked for Ralph Lauren and Vera Wang designing accessories in the ’80s. After her third son went to college, Heidi launched her accessory brand, Heidi Carey, at the age of 50.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I grew up in New York in the ’70s, and my best friend’s mother was Bill Blass’s muse, so right from the get go I was interested in fashion. After college, I worked in design at Ralph Lauren when Vera Wang was running accessories. I love classic style that never goes out of fashion, something Ralph had so perfectly created in the ’80s. I moved to California and started my first design business — a line of cocktail and evening outfits I sold to department stores. After raising three boys, I was dying to get back to work in design and so I launched Heidi Carey five years ago. At first I sold jewelry I designed and made myself. Eventually I got into home wear and other accessories that have sold very well.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

I’ve had the belief that classic style sold directly to customers at a reasonable price could become a great business. Until recently, with ecommerce really kicking into gear, that economic model didn’t exist. In order to sell direct and pass margin savings onto customers you had to do trunk shows, which does not scale up at all. But five years ago I saw how easy ecommerce had become, and I said it’s now or never! So I jumped in with both feet and never looked back. Direct to consumer (DTC) has been in mind since I was at Ralph, and now it’s a reality for me and all my customers.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

My husband is my partner in business. We have been married 30 years, and he is a bit more of a risk-taker. When I told him I wanted to build a DTC brand, he was super excited and has helped me build all the technology infrastructure we needed to grow. Mind you, he has no real experience in doing that! This is important for readers to understand, because I see so many women who want to start a business and the technology can seem scary. It isn’t. The tools we have today make it easy — anybody can do it, even me. I want to be the inspiration for as many women as I can, and ecommerce needs way more women involved than we have today.

What do you think makes your company stand out? Can you share a story?

It’s personal, for both me and my customers. I think it’s how real it feels to my customers. I’ve been sharing my journey on Instagram and email for five years and you can tell it’s a bit home grown! And with my designs, I’m not creating fashion pieces — I create things that resonate with customers for their simple elegance. There is a level of humility in the designs that always remembers it’s the woman wearing them who’s special, not the piece itself. So many women are beyond wearing brands. My job is to help my customer shine in her own unique way, and my designs reflect that.

How have you used your success to bring goodness to the world?

I am working hard to make the company carbon neutral, fair trade and organic. I look at Eileen Fisher and Stella McCartney as great role models for me. I believe my goal in business is to increase the well-being of everyone involved with creative invention, service and ethical action, to paraphrase Paul Hawkin from “The Ecology of Commerce.” The fashion industry has a wonderful opportunity to revolutionize the way our products are grown and sold, and I intend to join the leaders and lead myself.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Humility, humor and persistence are great assets when starting a business. I didn’t set out to change the world or overtake Polo — I started my business to make my friends happy and fill the spiritual hole the end of active parenting left. I have had so many failures and false starts. You just need to be able to laugh and wear it like a loose robe. Persistence can’t be reduced to a story because it permeates everything required to be successful. Never give up, always see the bright side, and don’t take yourself too seriously.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

I was told by marketing “experts” in my second year that I should not be the face of the brand! “People won’t necessarily relate,” they said, especially with my grey hair! Well I followed that advice and lost a year trying to introduce Heidi Carey without me — what a huge mistake. We are all looking for real connection in this world; no one needs another brand. By putting myself out there, especially at age 50, quite a lot of people related! There is a level of authenticity you just can’t manufacture with marketing.

Can you tell us a story about the hard times that you faced when you first started your journey?

Let me start by stating my belief that the hard times are where we learn, so while they may be hard they are the most valuable times we have. With that being said, there were so many mistakes; where to start? Like I mentioned above, when an “expert” tells you something that may not sit right with you, but you follow it — only to see things stagnate for a year, it’s really hard. But that pain taught me so much about what customers did and didn’t relate to. It was invaluable.

Where did you get the drive to continue even though things were so hard? What strategies or techniques did you use to help overcome those challenges?

Having a partner you trust and can rely on is crucial. We are never down on the same day, so when challenges start to really test you, one of us feels strong. I’m lucky to have my husband, but your main support doesn’t need to be someone this close. But I think to get through very tough times you do need a good partner.

The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder?

Highs and lows, setbacks and successes are all stories in our minds. I am a big believer in using our thinking to stay in balance when things are “bad” and “good”. My experiences tell me that I’m not that skilled at judging what’s good and bad, so I better just focus on the task at hand and not get too emotional.

Let’s imagine that a young founder comes to you and asks your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

How many women are being funded by VC’s? How many of those have worked? No matter what that number is, we need 100x more women in business if we are going to make real changes! If you can’t tell, I’m a bootstrap gal! That being said, “How big is your dream, and how soon do you want to get there?” would be my only two questions. My dream is to have a business that affords me a life I love, makes customers very happy, and I want to run it till I expire! I’m in no great rush, so Venture Capital is of no interest to me. If however, you have a really grand dream and you think time is of the essence, VC’s money and support may be the way to go. Personally, I would like to see more women bootstrap businesses like mine and help the younger generation of girls coming up do the same thing. We need way more women in business than we have right now, and if raising outside capital is necessary to achieve that, we will never get there. Bootstrapping is the best way in my opinion. Remember, 1,000 women running businesses each doing a million equals a billion! There’s so much strength in diversity!

Ok, super. Here is the main question of our interview: Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need To Create A Highly Successful Startup”? If you can, please share a story or an example for each.

1. You need desire. If you don’t have desire in your heart (not head) for this idea, it will never fly. I had been thinking about selling directly to customers and cutting out the middle man since I was at Polo.

2. You need a good partner. Things are going to get tough — they always do — so having a good partner you trust is essential. It’s also good if your partner has skills you don’t, so you compliment each other. My husband is a risk taker and vision guy. I am conservative and execution oriented. We compliment each other very well.

3. Profit and customer delight tend to produce success. When customers saw my jewelry designs for the first time, I could see the delight on their faces. I also knew my profit margin was in the right place for the both of us to be very happy.

4. A beginner’s mind. The world is changing so fast we need to be open minded about how little we know. This might sound crazy, but you know all those emails that are in your inbox asking you to try this or that service? I will try them all! I am happy to listen to any expert who has a product that might make my business better. I do at least three meetings a week with people who can teach me about my business as they try to sell me their service.

5. Humility and humor. Let’s remember how small we really are as a way to release some of the pressure we will be under while starting up our business. Zoom out when you’re incredibly stressed: Remember life is very short, and we are a small part of a much bigger whole. Have fun, and laugh at yourself for taking it so seriously. Today is all we have.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Too much strategy and planning and not enough execution. My partner suffers from head-in-the-cloud syndrome! Sometimes I have to say, “Stop taking over the world and ship these packages!” I see lots of entrepreneurs who are “going” to change this or that industry/world, but can’t make something people need/love at a profit. “Build it and they will come” very rarely works in my book.

Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

Very simple: Health and mental wellness come first. I know I sound like a mom, but the research shows that being tired = poor performance. Unhealthy living makes for unhealthy companies. Get out in nature often, have a strong friend group you hang out with often, and take care of your body and spirit every day. It’s the best investment all of us will ever make.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Dinner at home with neighbors once a week. I feel like we are all so isolated these days. If we all just invited our neighbors over to dinner one night a week we could solve lots and lots of problems. So many people talk about the kitchen table, but how many are actually sitting down and getting to know our neighbors? Oh, and you don’t have to cook it all — just get take-out or tell them to bring food and just enjoy each other’s company. No phones or TV allowed.

We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Eileen Fisher, Stella Mccartney, David Bronner or Yvon Chouinard.

How can our readers further follow your work online?

  • heidicarey.com
  • @heidicareydesign on IG/FB
  • @heidicareyshop on Pinterest

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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