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Bridget Firtle: “The mental health toll is real”

The mental health toll is real. Being an entrepreneur is a very lonely endeavor. It is extremely emotionally exhausting and that manifests in a variety of ways. You will find it hard to relate to most people in your life and although they will be super supportive (if you’re lucky) they will not truly understand […]

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The mental health toll is real. Being an entrepreneur is a very lonely endeavor. It is extremely emotionally exhausting and that manifests in a variety of ways. You will find it hard to relate to most people in your life and although they will be super supportive (if you’re lucky) they will not truly understand what you are feeling. Accept that. It is just the way it is. Try to find a network of entrepreneurs to talk and relate to if you can. If not, find a way to manage the stress, anxiety/fear of the unknown, instability and loneliness in the form of “release” which I discuss in a former question about burn out.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Bridget C Firtle

Born and raised in the Rockaway Beach neighborhood of Queens, Bridget’s true happy place is the beach. After receiving her MBA in 2007, Bridget began her career on Wall Street at a hedge fund as a consumer goods investor with a focus in global alcoholic beverage companies. In 2012, Bridget saw an opportunity to join the renaissance occurring in American distilling and founded Owney’s Rum — New York City’s only rum distillery — where she was recognized as a Forbes 30 Under 30, Zagat 30 Under 30 and one of Imbibe’s 75 People to Watch. Within five years of the launch, Bridget formed a strategic partnership with international spirits company Proximo Spirits, and in early 2020 she successfully sold the company to launch Rockaway.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I come from a long line of entrepreneurs on both sides of my family, so I felt as if being in my own business was in my blood. In business school I was drawn to studying finance because math and numbers always came naturally to me. I’m also pretty competitive and that’s where all the alphas were going and I wanted to beat them at the game. After a Bachelor of Commerce and an MBA, I landed a nice job as an investor at a hedge fund where I developed a specialty in investing in global alcoholic beverage companies (I like to invest in what I like to consume :)).

Several years into my hedge fund career, I came to a realization that I needed to move out of the company if I was to move up in the industry. I had sort of maxed out my potential there. I began to contemplate my next move and do some soul searching, networking, interviewing, the usual routine. My interest was in private company investing and moving into the VC world and out of public markets (or so I thought). Over six months of thoughts and observations about myself and the opportunities around, I concluded that I should build a distillery in Brooklyn and make rum. Definitely not something I thought I would do when my kindergarten teacher asked what I wanted to be when I grew up! But, I had ended up unintentionally cultivating a vision to bring rum distilling back to my hometown of NYC (where it was first distilled in the US in 1664) while watching a TED talk on Venture Capital at my desk at the hedge fund. In retrospect, I guess months of opening up my mind to opportunity resulted in an ‘Aha moment’ based on my experience watching trends in the resurgence of American distilling, a white space gap in the rum category, my desire for a big change, and an entrepreneurial spirit asking to be ignited.

About five years after building the distillery and launching Owney’s Rum, I was approached by a large spirits supplier (Proximo Spirits) to form a strategic partnership with the intent to fully divest my interest over the following 3–5 years at my option. It felt like the right time to align with a national partner and increase distribution as I had come to learn that getting Owney’s as big as I thought it could be was going to be nearly impossible as an independent company, given the market dynamics. So, in 2017, I inked a deal that began integrating my first baby into a large organization and scaling it to max capacity. The next three years were an invaluable experience in learning about bigger companies and also learning lots of things about myself. As I journeyed through this, I had time to come up for air for the first time in 5+ years (starting a business can be a true whirlwind, like a hamster in a wheel) and think about what I wanted next. I also experienced some major life defining moments from 2017–2020 that impacted who I am today and what I wanted out of the next part of my life. Again, soul searching whether deliberate or not. Conscious or subconscious…

It all amalgamated in 2 business concepts that I set out 2020 to launch after a planned departure from Owney’s and Proximo Spirits. The first a boutique strategic management consulting and financing business for CPG start ups — The Cyclone Group. This progression seemed natural — I had the analytical and financial theory skills from business school and Wall Street combined with real life, hands on operational experience from start to finish with building a consumer goods business (PS that professor was right in the TED talk back in 2011 — there is NO better education than starting a business). I could use all of that to help entrepreneurs in the thick of it.

The second idea was purely a “for fun, passion project, side thing” born out of my love for my hometown of Rockaway Beach, New York City, the ocean and my constant pursuit of balancing health + wellness with partying + fun. I wanted to can this essence of myself. The result was Rockaway — a line of canned sparkling waters infused with adaptogenic herbs embracing the unique energy of Rockaway Beach, NYC and mission driven to save the ocean. As the vision came to life, I have become more and more fired up about it and now truly ignited by the potential I see for it. We have a dual X dual internal mission statement: dually functional (good for you X good for the ocean) and dually accessible (taste profile X price point). Although we just launched nationwide digitally, I am so pumped and going all in. The Cyclone Group may have to take a back seat for a bit. Time to execute, iterate, and re-execute. Put in the work. You heard it here first, it’s going to Rock (pun intended?).

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

I think I have enough of these stories to write a novel. How much time do you have? Ha! Looking back, I think when I first started Owney’s I really had no clue what I was doing, but I definitely thought I did jumping in! (It should be noted that I think you need to be naive to an extent when you are starting a business or else you’d never do it! So there was a lot of hardship as I learned on the fly (totally alone for the first 2 years). Securing Start Up Capital. Managing Working Capital while Operational. Driving Sales. Navigating as a tiny brand in a market of HUGE companies and strong market forces — distribution, marketing, promotions. Managing the intensity of the regulatory environment of the US liquor industry. Ensuring a consistent message in public communications. It’s more about how you handle and adapt to all shit flying at you constantly. Putting out fires while staying calm. Problem solving. The storm never stops, you just get used to dancing in the rain.

Where did you get the drive to continue even though things were so hard?

I never lost my initial vision for Owney’s. I adapted to the market and digested information as it changed to keep pushing for success, but I never lost that burning feeling in my gut that what I saw as an opportunity was real. I kept visualizing the goals (a practice I was taught as a competitive swimmer, but SO impactful in many facets of life). That’s not to say there weren’t one million times I wanted to run far, far away. I’m not really sure why I didn’t — I guess I have a good amount of strength and also probably some ego in there. Oh yeah, and I still truly believed in the opportunity in front of me.

Ultimately, at the lowest of lows — every time I felt like I was up against the ropes getting worked about to tap out I would try to find the tiniest bit of energy from somewhere in my soul, concentrate hard on it and push it through my body to keep swinging. Then inevitably, things would *CHANGE* and shift slightly positive, momentum would build and the pendulum would be on the upswing. Only to eventually swing the other way at some point, but you become more and more tolerant with each swing.

It also shouldn’t go unnoted that I have a tremendous support network in incredible family and friends. They helped (and continue to help) pick me up when I’m falling. There is no success without them. End of story.

So, how are things going today? How did grit and resilience lead to your eventual success?

Hardwork and perseverance are a BIG part of the battle. Understand that being patient (but persistent) is imperative to success. Put in the work. Hang. In. There. Hold the vision, change the strategy as you listen and adapt to the market environment and keep moving forward. Practice learning when to keep using the same tactic to see a result and when to abandon ship. It’s not easy. Also accept that and be kind to yourself.

Things are really good right now! But, I know that’s only temporary. Everything is. I will try to enjoy the moments more on this next adventure with Rockaway — it’s like a new baby, very exciting, lots of happy and positive energy. But, I will continue to practice everything I just mentioned. I am very far from having it all figured out.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I have 2 funny stories that come to mind at first thought (one from each of the first 2 chapters of my career):

  1. When I was right out of school and job hunting (and therefore giving my cell # out to a lot of people) I once picked up my phone to a blocked number and said “heyooo what’s up?” To be fair, the only line I knew at the time that was blocked was my parents so I instinctively thought it was one of them. It was not. It was a recruiter who proceeded to ream me out. I was mortified and quite upset afterwards. But, I think it’s hilarious now. Lesson: don’t answer your phone like a fool unless you’re certain you know who is on the other line.
  2. The first time I ran a distillation for Owney’s was long after the still was actually installed (because it took what felt like a million years for the city and DOB to sign off on the construction). Apparently, there was a cap missing on the back of the pot that needed to be replaced (but I had forgotten about it) and by the time the liquid inside of the 265 gallon still started to boil, burning hot alcoholic molasses water started to project like a geyser from the back of the equipment and rain down all over my distillery. I VERY stupidly ran underneath the burning liquid and managed to cap the hole while “the geyser” was very active. I was alone and it was just instinctual but so dumb — I could have been severely burned. Lesson: you probably should not run a manufacturing plant alone (but I continued to do so for a couple of years) and you should just turn off the still and let the liquid cool down after the mess is made next time.

TBD on a funny story Rockaway related, but I’m sure it’s imminent.

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

I think being real and authentic goes a long way — aka having integrity. No gimmicks. We are what we say we are. We do what we say we are going to do. My current company, Rockaway, was born out of true passion and love from my soul and you can’t really fake that. Honestly, it started as a “for fun thing” after selling Owney’s Rum (learned that I am incapable of doing anything on the side, and must go all in) that combined my love for my hometown of Rockaway Beach, NYC, the ocean, and my constant pursuit of balancing health + wellness with partying + indulgence. Work hard, Play Hard.

Aside from that, I think the way we approach the ‘market opportunity’ with Rockaway is unique. We make a high quality, functional product but we don’t make it too precious or exclusive. We aim to be having fun all the time and make our product available to as large of a demographic as possible with the right price, taste profile, and aesthetic. We want to make these niche and somewhat esoteric ingredients accessible to the masses. And we are driven by a mission to combat climate change and plastic pollution through helping our beautiful oceans which I think most people can get behind.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Find places to release! Take care of (and be kind to) yourself. I have two main outlets: exercise and fun!

I push myself into physical discomfort regularly through exercise. It helps me deal with everyday stress and emotional discomfort because I get used to feeling uncomfortable. I practice the difference between thoughts and feelings in that regard. Sometimes this involves shaking my body and yelling — That type of energy release is a great antidote for anxiety. It causes a release of tensions and a shift.

I also make lots of time for friends, family and fun. I love to laugh hard and dance wildly to rap music. Take the trips. Plan to disconnect.

Day to day, I advise colleagues to recognize when they are having a bad day. Accept it. Treat yourself. I tend to choose french fries and wine. Maybe a funny show or movie. Go to bed. Tomorrow is a new day, it will be better. Onward!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I am who I am because of my parents. My entrepreneurial spirit comes from them. My strength comes from them. I’ve inherited a tremendous amount of knowledge from them. Not only genetically of course, but in the way they raised me and lessons learned along the way. They were both middle class street kids from Brooklyn that came from families of small, local business owners (bars, candy stores, toy rack companies) and crossed paths during their PhD program at the CUNY Baruch business school (note: my mom was the only woman in the program). After their doctorates, they both went on to develop rich resumes — my Mom, a renowned professor and commercial real estate entrepreneur and my Dad published textbooks and had an extremely successful marketing research consulting business that serviced many Fortune 500 companies.

During my childhood, my Mom spent a lot of time at home while working on the side while my Dad ran his business. She sacrificed and put her professional career on hold to dedicate herself to me and my sister. I can’t imagine that was an easy decision for a woman of her stature at that moment in time — especially having come from nothing to achieve what she had before children. Of course her efforts are pivotal in making me who I am and for that I am so grateful. Later in life, my Dad sold his business and my Mom cultivated her commercial real estate success. Because of this timing, I spent a tremendous amount of time with my father coaching me through and supporting my first entrepreneurial venture in the rum business. He was my biggest supporter and confidant — definitely the unofficial Chairman of the Advisory Board. He gave me strength, could relate to my feelings and was just so smart and capable to help direct my decision making. I’ll forever cherish that I could share that part of my life with him and the success of the business would not have been possible otherwise. Our stereotypical ‘father-son’ relationship would not have existed without my mother molding me from the onset, of course.

I’m so happy they are mine.

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

I am using my new company, Rockaway, to drive a mission close to my heart — helping save the oceans from climate change and plastic pollution. Donating a portion of gross sales is a great way to use business to fund non-profit actions you are passionate about.

I also try to give my time to counsel people trying to start a business or to advise on certain things as they move through their career. I think it’s important to make yourself available to share some insight and experience when you can. It’s good karma for when you are asking others for help yourself 🙂

But, just as important as both of those actions, I think starting a business and being an entrepreneur inherently brings goodness to the world. You take risk, you create jobs and employ people, you proudly pay taxes that (ideally) help people who need government assistance. I truly believe the future lies in the hands of businesses taking on responsibility to make the world a better place. Responsible consumers will also dictate and drive the success of those businesses. Unfortunately, I have little faith in the government these days.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

  1. The mental health toll is real. Being an entrepreneur is a very lonely endeavor. It is extremely emotionally exhausting and that manifests in a variety of ways. You will find it hard to relate to most people in your life and although they will be super supportive (if you’re lucky) they will not truly understand what you are feeling. Accept that. It is just the way it is. Try to find a network of entrepreneurs to talk and relate to if you can. If not, find a way to manage the stress, anxiety/fear of the unknown, instability and loneliness in the form of “release” which I discuss in a former question about burn out.
  2. It takes a long time. Be patient. Temper the Ego a bit. Starting a business 101: “It takes longer than you think” — I definitely heard that before I started my first business. But, I think the better advice would be to say ‘practice patience’ to someone like me who is not very patient. I also think explaining to the entrepreneur that it is important and probably imperative to success to think they can ‘do it better’, ‘do it faster’ etc than anyone else — but that needs to find balance with reality. Bring your head a little closer to the ground and try to make a practical and realistic timeline to achieve goals. Then cut it in half — that should be a good jumping off point to check your ego.
  3. Don’t give up control of the books. Closely monitor your bank accounts for as long as possible. Almost daily (definitely weekly), look at your balances, register what bills are coming in in the next week, note what revenues you expect (and how much is firm) — rinse and repeat. Don’t just let an accountant ‘keep your books’ — they will only tell you you have no money when it’s too late. I outsourced my back office too soon with Owney’s, I am doing things differently with Rockaway. CASH IS KING is a saying for a reason.
  4. Change is the only constant. Pivot quickly when necessary. Having a plan is essential, but understanding that nothing is going to go as planned is equally as important. When you are starting, you need to stay nimble — it’s one of the advantages small companies have over big companies — the ability to change course quickly. Change is the only constant — accept it, digest it and then adapt to it. If you can get lucky or prepared enough to anticipate it, you’re really competitive.
  5. You should wait as long as possible to do a priced equity round when raising money. Opt for convertible debt notes instead. I pitched a decent number of investors when I first set out to raise money for the rum project. I can’t believe nobody guided or advised me towards issuing a convertible note (or something of the like). I guess it was because they were also young and inexperienced in private equity investing (mainly public markets people). Anyway, in retrospect, and as both an entrepreneur and an investor I can tell you setting a price or valuation for your business will constantly be a cause of tension at any round (the entrepreneur will always think the business is worth more and the investor will always want a better price or deal — ideally, both sides walk away from the table satisfied in the end). Furthermore, it is nearly impossible to value a pre revenue investment as all the value is on the come and essentially made up (hopefully well researched) numbers in an excel spreadsheet. Therefore, the longer you can push off setting an initial price for the company, the better for both sides. Convertible debt notes, or similar instruments, allow you to compensate you investors in multiple ways for taking on great risk in the nascent stages. They also allow you as the entrepreneur to execute and grow the business to a bigger price tag so you don’t take as much of a hit to your equity position (aka don’t give up as much of a %age of your business) when the priced equity rounds eventually come into play.

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. 🙂

I really am perturbed about the food supply in schools. As a proud product of the NYC public school system, I think we can do way, way better. I was fortunate enough to have home-made and healthy meals, but I know lots of kids in the city do not have that luxury. In retrospect, I do not take that for granted — I was lucky to have a very smart and educated mother who curated a balanced diet. I’ve recently observed the school meal options as an adult with a lot of friends who are teachers and it’s very upsetting. We need to teach and offer children much better food from the earliest possible age. Not only will it save lives in the long run, it will save the healthcare system a lot of money. ou truly are what you eat. Is it rooftop gardens with fresh food on every building? Is it more subsidized lunches? I don’t have the answers as I haven’t had a chance to do the work yet — but I know there are plenty of people out there trying to solve this problem and I’d love to join them eventually.

How can our readers follow you on social media?

Personally on instagram, @bridgetcfirtle or linkedin Bridget C Firtle

And please follow my new business baby, @drinkrockaway

This was very inspiring. Thank you so much for joining us!

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