Susan Hassett of Cocktail Sneakers: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

An Interview With Pirie Jones Grossman

Pirie Jones Grossman
Authority Magazine
Published in
18 min readJul 21, 2021


Designs take a great deal of time and many iterations before they “go to market.” I had several designs in mind, on the first run. One, in particular, we struggled with, and it became a real stickler with the factory to the point where they suggested we table (well…scrap is what they said) the entire design. I loved the style and had an inkling it would be popular so kept pushing the team to fine tune it. That particular design has consistently been our best seller! It’s important to work collectively with your team and to listen, but at the end of the day if you truly believe your ideas are the correct way to go, then express that, but always in a collaborative way.

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50's.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Susan Hassett.

Susan C. Hassett is the founder of Cocktail Sneakers, a women’s sneaker brand that is redefining sneaker culture for women. Having founded the business in her early 60’s, Hassett is also a vocal champion for late-stage female entrepreneurship, encouraging women to pursue their passions regardless of age of life stage. Prior to launching Cocktail Sneakers, Hassett also founded and operated a highly successful telecommunications business, Conferencing Services International (CSI), an outsourced audio and web conferencing company, which was acquired by Genesys Conferencing in 2001. Her leadership, sales and development skills have been tapped through multiple philanthropic roles in recent years including as president of the University of San Diego’s Parent Board, member of USD’s Parent Partnership Fund’s executive committee, and development volunteer with Room to Grow, a grassroots support program conceived and developed by Julie Burns and Uma Thurman that enriches the lives of babies born into poverty throughout their critical first three years of life. Hassett has also served on the Board of Trustees at Colby Sawyer College, the institution from which she matriculated, in 1979.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I was born in Minnesota but grew up in Upstate New York surrounded by a loving family that included four siblings and my parents. My father worked extremely hard to provide for the family while my mother worked equally as hard as a stay-at-home mom running us here and there between sports, dance, piano,

Girl Scouts and everything else my brothers, sister and I got ourselves involved in. My parents were driven to put all four of us through college; an opportunity not presented to them given their military obligations of World War II. They taught us how to work hard and pay our way — whether working at a small store, babysitting, or picking blueberries at a local farm. My father always said, “a buck is a buck!” I believe my work ethic was instilled in me years ago by my incredibly hard-working parents, and that work ethic has gotten me to where I am today at Cocktail Sneakers.

Give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“No one who achieves success does so without the help of others. The wise and confident acknowledge this help with gratitude” ~ Alfred North Whitehead

This quote literally hangs in my office (see photo below) where I can see it every single day. There are phases in every person’s life, both personal and professional. It is a rare few who can soldier on without any assistance. I’m not one of them. In fact, there has been a trail of special individuals who have guided me along my journey — offering advice, experience, counsel and humor. They are the ones who have given me both the courage and motivation to persevere.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

  • COURAGE: When one starts down the path less traveled, everyone suddenly has an opinion. It’s not always a positive one, either. Entrepreneurs need to lean-in to courage not only when they take their first steps and decide to jump in but the courage to ignore the “nay sayers” and irrelevant noise around them. I remember attending a cocktail party at which someone I barely knew decided to proclaim out loud for all to hear “the whole sneaker thing for women is short-lived and over.” Thankfully, I vehemently disagreed and soldiered on!
  • HUMILTY: This is a trait generally present in all entrepreneurs. While many have foundational mojo and confidence, it takes a tremendous amount of acumen and wherewithal to build a new business. Unpredictable mistakes, missed family meals, and intimidating meetings remind you to stay humble and grateful.
  • PASSION: I had an idea that I believed would work. Not everyone agreed, yet I quietly pursued my passion for several years prior to officially launching my business. Every last detail — from materials and colors to intricate design elements — was double and even triple-checked. I thank goodness for my design team who tolerate my attention to detail. My point of view was that Cocktail Sneakers had only one chance to launch for the “first time,” so everything needed to be perfect. We created a beautiful collection of sneakers, but needed the photographs, brand book, and website to match. If you are truly, in-your-gut passionate about the work you do or product you have designed, it will manifest in the final product. It’s just that simple.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

After giving birth to my first child I, like many women, wanted to have it all — a family and a career. I started my first entrepreneurial venture in the telecom sector. Using the extra bedroom in my house as an office, I made cold calls to clients while my son slept in the next room. Over time, the business grew, and I was able to move into a small office not far from my home. When at the pinnacle of my first business, I learned I was pregnant with my second child. I was determined, as many other working moms, to find a way to make it all work and juggled two kids, a successful business, and regular mom duties including carpools and school functions, and was always at the door when my children arrived home from school. After 11 glorious years in telecom, I sold my business and funneled my time and talent into philanthropic pursuits. I was asked to serve on the Board of Trustees at the college I matriculated from — Colby Sawyer in New Hampshire. In the seventies, when I attended Colby-Sawyer, it was a small, all womens college.

This institute of higher education instructed and guided 800 young ladies during an era when the majority of women were not expected to be much more than secretaries. During our graduation ceremonies the commencement speaker told the Class of 1979, “Don’t be what your mothers were…be more.” Now, as offensive as that was to my mother, I understood the message that was being conveyed. As young women embarking on the world we had much to give, we should be courageous and pursue our dreams. I have never forgotten that commencement or the advice given to us on that day. I also served on the Board at the University in San Diego. In this role, I met men and women from across the country who together created The Parent Partnership Fund scholarship program that provides for iunior- and senior-year students who have fallen on financial difficulty. It was a creative way to get many USD parents involved. Soon after, I got more involved in development for a grass-roots non-profit called Room to Grow, a grassroots support program conceived and developed by Julie Burns and Uma Thurman that enriches the lives of babies born into poverty throughout their critical first three years of life. The organization has since evolved into a major force battling childhood poverty.

How did you “reinvent yourself” in your Second Chapter?

In my opinion, most women evolve through several life chapters. As we become young women, many of us marry to become wives and mothers, while others, executives, caregivers, or volunteers. Interestingly, women seem to innately know when the time comes to end one chapter and at the same time, turn the page on a new one. Each chapter lifts us through the next, allowing us to impact our lives and those of others in some way — oftentimes without us even realizing. I don’t subscribe to the belief that I “reinvented” myself. Rather, I evolved through another life chapter. All that I’ve done to date steadied me as I jumped into another entrepreneurial venture, in an industry that has been historically dominated by men. I leveraged my experiences, mistakes, knowledge and skills learned from various past chapters and carried it into my current one.

Tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

For some time, I had observed how confidently men wore fashion-forward sneakers with nice pants and suits. They paired sneakers with high fashion just as readily as they did athleisure — whether in the office, out to dinner, or when traveling. Every time I’d see them walking through the streets of Boston or New York City, at airports, etc. I would wonder why this same option wasn’t available for women. Women too can wear sneakers, yet the majority of women’s sneaker designs are fitness-focused. From my vantage point, I didn’t see a sneaker out there with feminine sensibilities that allowed a woman (no matter what her daily routine) to seamlessly transition from sunrise to sunset with effortlessly chic style in her sneaker selections. Moreover, there are limited options that pair as stylishly with a skirt or dress as they do with jeans or leggings.

When away on vacation one summer, I went in search of a fashionable pair of shoes to wear to a cocktail party. The event was outside near the ocean, so I had no intention of wearing heels, but I still wanted to feel polished. Most importantly, I wanted to be comfortable as I knew there would be lots of standing and walking. I visited at least a half-dozen boutiques in town and just could not find any footwear that actually “checked all the boxes”….stylish and comfortable, all the while having a sense of femininity. It was my “ah-ha” moment! What I was looking for was a pair of ‘cocktail sneakers.’ In that instant, the concept was cemented, and my work began.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

The truth is, when I decided to start Cocktail Sneakers, I did so with no footwear industry experience. I’d started another company, in telecom not sneakers, so with my idea in one hand and determination in the other, I started my journey. I spent years doing research, meeting with sneaker designers, following trends, and educating myself on branding, marketing, materials, and the industry as a whole. Failure was not an option. There was much I didn’t know, but not knowing served as the driving force for me because I not only wanted to know, I needed to know. The more I learned, the more confident I got. When my sneaker samples arrived and I started to wear them (testing our products was crucial), women would comment on them and asked where I had purchased them. The pride of ownership (plus secretly knowing they were my designs) exhilarated me. As our first brand book took shape, it all seemed to become more real. I was building my team — all of whom were depending on me — so I had no choice but to make it work.

How are things going with Cocktail Sneakers? We would love to hear some specific examples or stories.

Cocktail Sneakers is still a young brand, as well as one forced to pivot during an unanticipated global pandemic. Even so, I’m incredibly proud of our accomplishments to date. Our sneakers are inventoried at upscale boutiques and luxury resorts throughout the country including Canyon Ranch, Miraval, Mohonk Mountain House, Everards and more, and Cocktail Sneakers have been named a “Favorite Fall Shoe” and ranked as a top gift for moms and travelers. We’ve added several new seasoned sales professionals to our team and cemented ourselves as a brand to be reckoned with, yet what we’re most excited about is how women are beginning to view sneakers as the new power shoe for women (thank you Kamala Harris, Oprah, Reese Witherspoon, Meghan Markle, Jennifer Garner and others!). We learned during 2020 that dressing comfortably doesn’t mean dressing shabbily. Cocktail Sneakers are giving women the opportunity to elevate their casual style, to be fashionable and feminine, and most importantly, comfortable. Sneakers are literally becoming as fashion-forward for women as they have been for men.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that

It may sound cliche, but I have to give credit to my husband, John. I, of course, believed I had a great idea with Cocktail Sneakers, but my husband’s support gave me even more courage to take the plunge. My husband too is an entrepreneur and inventor, and a firm believer in pursuing your dreams. He also has always believed in me and reminded me of things I didn’t see in myself. Although he’s not in the fashion world (and I’m a self-proclaimed fashionista), he would listen intently as I explained how women shop, noodled cost analysis with me, and patiently thumbed through brand books to share his opinions about layout. He encouraged me when I was feeling low and applauded every victory. Having a supportive someone by your side makes the journey more enjoyable.

Can you share the most interesting story that happened to you since you started Cocktail Sneakers?

One of the most memorable moments is when I met my all-female design team in Brooklyn, N.Y. On that trip, I was advised that I would need to travel to one of our manufacturing facilities overseas which was located in a country I’d never in my life traveled to. This was a pivotal moment as I couldn’t just staff out the assignment or ask someone else to travel in my stead. As the company owner, I needed to go myself to finalize the manufacturing run, sizes, expectations and to also negotiate future inventory plans. A week later, my husband dropped me off at the airport and I walked, with heart pounding, through the terminal doors. There was no turning back. After a little personal pep talk, I assured myself that I was mature enough to make the trip and smart enough to handle whatever came my way. So, with passport, money and cell phone in hand, off I went! Having bootstrapped Cocktail Sneakers myself, I was on a tight budget and a tight schedule. My travels would take me to several destinations, including one where I had to be driven by a stranger two hours away from my hotel to one of the manufacturing facilities. All I could think was advice my mom instilled in me as a child which was “don’t get into the car with strangers.” Yet, there I was — in a strange country being driven in a van by a stranger. My nerves and self-doubt seemed ever present, but in my heart, I knew that I was exactly where I needed to be. I had a job to do and I wouldn’t leave until that job was completed. Upon my arrival, my colleagues treated me with kindness and professionalism. We collaborated for five straight days, during which we finalized every last detail of Cocktail Sneakers’ first designs. I was absolutely exhilarated…and exhausted…and that trip taught me a lot about courage, perseverance and the value of genuine kindness.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I think people would be telling an untruth if they didn’t say that at any point in their life, both personal and professional, there are struggles in believing in oneself. Those that set out to attack the day will eventually nudge up against some type of struggle. Not enough time in a day, juggling one too many projects at the same time, missed deadlines, etc. Generally speaking, I am a very confident person however the pandemic most definitely created an overarching umbrella of concern. How would lockdowns impact our retail partners and what would the ripple effect be for our team? Could we successfully pivot to direct-to-consumer and how much time and cost would be associated with that approach? Will we succeed? For entrepreneurial leaders, it can be difficult to remain the beacon of positivity when you yourself aren’t completely sure about what is going to happen next. I can specifically recall several days during the last year when I’d walk back into our warehouse, close the door, sit on the floor, stare at our sneaker inventory, and ask myself, “how am I going to get through this?” Even in these temporary moments of insecurity, I knew I’d pick myself up, give myself another pep talk and remind myself why I started the business. I believe in the products we created and know, deep in my heart, that they may very well change how women perceive sneaker wear. Our clients too remind me often that small changes, even the shoes on your feet, can positively change how they feel about themselves. That is so valuable — knowing that something we’ve done improves the way women feel. Given my history, I believe that my life’s work has always been directly connected to changing and improving the lives of others in one way, shape or form.

How or what did you do to create a support system before you moved to your new chapter?

I am so fortunate to have an in-place support system and therefore, didn’t need to create one from scratch. My friends and family have historically been a backbone of support, often encouraging me, erasing self-doubt, and championing my creative direction every step of the way. I found it so much easier to take the plunge knowing I had this incredible group of humans in my corner from the very start.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

Starting a new chapter is very exciting, but I won’t lie, it also takes a lot of courage. When I started Cocktail Sneakers, I was officially in the “late-stage entrepreneur” phase — and a time in my life when it would have been easy to sit back and enjoy the fruits of years of labor. But, I innately knew I had more to give and that I wasn’t ready to fade slowly into the sunset. My sons and husband rallied around me, encouraging me to follow my passion regardless of my age or life stage. My friends who still held positions in business too gravitated towards my new idea, offering beneficial counsel, tips and helping make connections in the design and footwear industry so that my initial toe-dip would be supported by an incredible bank of education, knowledge and networking potential. With such a strong foundation, I felt confident that I could take the next step. Having gone through a multi-year process myself, I am now an avid and vocal champion for late-stage female entrepreneurship.

What are your “5 things I wish someone told me before I started Cocktail Sneakers” and why? (video included) Please share a story or example for each*.

  1. Designs take a great deal of time and many iterations before they “go to market.” I had several designs in mind, on the first run. One, in particular, we struggled with, and it became a real stickler with the factory to the point where they suggested we table (well…scrap is what they said) the entire design. I loved the style and had an inkling it would be popular so kept pushing the team to fine tune it. That particular design has consistently been our best seller! It’s important to work collectively with your team and to listen, but at the end of the day if you truly believe your ideas are the correct way to go, then express that, but always in a collaborative way.
  2. Building the right team can be challenging. As a later stage entrepreneur, I was on a learning curve with all aspects of my business. Each department needed to be considered and thoughtfully staffed with the right people to help get Cocktail Sneakers to the net level. At the beginning, I hadn’t yet acquired enough knowledge and ultimately made a few mistakes in how we invested our money and what teams we built out first. In the process however, we gained creative counsel, perspective, and forward momentum from numerous individuals — and I too learned many valuable lessons. As a startup, it takes a special group of people with innate passion for what you are trying to achieve, the work that you do, and the industry you serve. Building a brand takes tenacity, patience, flexibility and fortitude. Although it took us some time and patience to find just the right fit, I was a “sponge” throughout the entire process, soaking up every bit of information I could from all I came in contact with. The right team requires an understanding of how they all fit together, how they each contribute to the end game, and how to effectively collaborate while also staying in their respective lane.
  3. Marketing is very expensive — especially for startups on a budget. At the beginning, I was educated quickly on the differences between the graphics person, the social media person, the marketing person, the website designer, etc. With that education the picture became clearer that not only did I need all these people to help build the brand, but they all needed to be paid. I quickly learned that “freelancers” are a young brand’s best friend! You don’t need to work with a large, expensive agencies to get work done. You do however need to invest time in sourcing the best fit talent for every stage of business growth.
  4. All entrepreneurs have days when they ask themselves, “What the heck am I doing??” This couldn’t be clearer than during dark days after the pandemic hit, but also applies to overall growing pains when building a business. There are great days when sales are skyrocketing, press wants to interview you, and bills are easily getting paid. Then, there are also the opposing days when self-doubt tends to creep in. I have found myself alone in my warehouse, several times, looking at our beautiful sneakers and wondering what I had gotten myself in to? If others had advised that those days would occur, perhaps I wouldn’t have taken those days so personally. Some days will be stellar, and others, not so much. There will always be an ebb and flow. Perspective is key.
  5. I wish someone had told me that the word “pivot” would become vital in the brand journey. Had we seen COVID-19 on the horizon, our team could have prepared for the lunacy that marked this tumultuous time in our history rather than second guessing ourselves for months at a time. The pandemic forced us to stretch beyond our comfort zone in ways we weren’t quite yet ready to stretch. The word “pivot” became important within our everyday team dialogue. We learned that life will throw lemons at you, and if you want to be successful, you’d better learn how to (quickly) make lemonade. Maintain an open mind. Remain flexible and nimble. Take an unexpected path. Try a new approach. We did all of those things and ultimately learned that our original path improved by taking a few detours.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Interestingly, I believe we’re already inspiring a movement as Cocktail Sneakers set out to ‘redefine sneaker culture for women.’ This mission sits within the core of our company’s DNA. Our designs were created to motivate women not only to be comfortable wearing sneakers, but confident wearing them with skirts, pants, dresses, suits, capris and so on. We’ve set out to shift industry perceptions about heel-wear and encouraging women to ditch their heels for elevated footwear options that can take them from board room to brunch in comfort and style. There will always be a time and a place for heels, but our hope is that women, just like men, will gain confidence in wearing fashion-forward footwear that does not cause ankle sprains, broken toes, toenail loss, blisters or aching arches. Cocktail Sneakers are a healthy alternative to dress shoes and heels designed to dress up both casual and professional outfits. We’re on a journey, not a destination.

We are very 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 with, and why? He or she might just see this if we tag them.

I would be thrilled to meet and have a conversation with Sara Blakely. Other than her obvious, tremendous success, she is someone from whom I would welcome advice. From a distance, I’ve followed her ascendancy and realize that she started her business, in many ways, very much as I did. She had an idea to help women with an historic challenge, had a small amount of cash to invest in her idea, and heard a lot of “no’s” along the way. Sara… if you are out there and reading this, take a look at Cocktail Sneakers and let’s meet for lunch!

How can our readers further follow your work online?

Our website:; Social (FB/IG: @CocktailSneakers)

Thank you so much for sharing these important insights. We wish you continued success and good health!



Pirie Jones Grossman
Authority Magazine

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.