From Wall Street to Watersports: Stephanie Shideler’s Journey in Stand-Up Paddling

From a former finance professional, to one of the strongest female stand up paddling athletes in the racing world, we are honored to have had the privilege to speak with Stephanie Shideler. Steph is a true testament to finding happiness by following your passions and chasing your dreams. Now 49, Steph’s journey from the fast-paced world of Restructuring Investment Banking in New York to the serene waters of Florida offers a fascinating perspective on pursuing passion over corporate success. She shares her experiences with her early days from SEAPaddle NYC, her partnership with Flying Fish, and her current goals as a professional team rider. We are stoked to explore with Stephanie how paddling has not just shaped her athletic career but revitalized her entire outlook on life.

Hi Steph! Thank you for joining us on TotalSUP today! Can you introduce yourself to us?

Hi Maddi! I’m 49! I grew up in California and then moved to New York for work in my 20s. I’ve been in finance for all of my “career” – mostly focused on Restructuring Investment Banking (dealing with large companies in distressed situations and bankruptcy). I retired from that career in 2018 and moved to Florida in 2021. As far as family, I have one sister who lives in France, a bunch of rescue dogs, and my boyfriend Troy.

Thanks Steph! That sounds so lovely! We would love to know, how did you first discover stand up paddling? What was your first experience like? Can you walk us through what that day looked like?

I definitely remember my first time paddling! The impetus was the SEAPaddle NYC, which I believe started back in 2007 – a roughly 26-mile circumnavigation of Manhattan. I was a cheerleader on the support boats for the first couple years, but then I decided to attempt the race. Originally I thought I would paddle it prone, I surfed a lot and that seemed like a natural choice. But I started training on the prone board and realized it might be a lot more fun on a SUP. I got a 10’6 surfboard style SUP made by a local shaper on Long Island in 2010 or 2011 (I can’t quite remember). But what I do remember is my legs feeling like wet noodles the first time I got on the board! However the second and third time got a lot easier. Luckily, someone got me a 12’6 touring style board right before the race and I managed to make it around Manhattan at a pretty decent clip. It was the most incredible way to experience the city!

For the first few years of my paddling life, I just trained a little bit for the SEA Paddle and another local race known as the Dean Randazzo, also a grueling island circumnavigation in New Jersey. I suffered through those during the summer months and then put down my paddle and went back to corporate life for the rest of the year. I didn’t know much about the growing paddling scene and thought all races were over 20 miles at first! Then I discovered some local races that were in the 6 – 10 mile range. We were lucky enough to have guest appearances from professional women like Annabel Anderson, Candice Appleby and April Zilg, which was inspirational and started to light the fire for me. After a few years I started to travel to bigger races and in 2018 I left my job mid-year and solely focused on paddling. I was able to go to Europe for a couple races and I spent a lot of time in the Gorge in Oregon.

Wow! What a journey! Can you please tell our readers how you partnered with Flying Fish and how you have worked extremely hard to be a professional team rider for them?

I remember first meeting John after the Key West race in 2018. I’d had an outstanding race, coming in not too far (for me at the time) behind Seychelle and Terrene Black. I remember John going out of his way to congratulate me on a great performance. He seemed genuinely happy for me. I didn’t really know who he was or anything about Flying Fish at the time. I just thought it was such a kind gesture. Fast forward another year, and I was traveling through Florida for a couple races. I was dropping a board off at the Flying Fish factory for a friend and John gave me a tour and said if I ever wanted to join the team, to let him know. I was really impressed by what they had going on and I loved the custom aspect. It took me a year, but I finally went back to him and said I wanted to join. I realized that, sponsorship or not, those were the boards I wanted to be riding. They are so light and fast – my times were instantly better when I got my first Flying Fish board. Little did I know I would be joining the most incredible group of people within the Flying Fish community.

We are so stoked you have the Flying Fish family to support you and your athletic career! What is your go-to Flying Fish board that you ride?

Right now, my go-to is my 14 x 21 Freedom Pro full dugout (about 5″ deep) 273 liters. I got it as my “flatwater” board, but it’s so stable I can use it as an all-around. I also have a 14×22 Freedom Pro full dugout 283 liters for nastier conditions. They both have the cool drizzle colors, and I love how creative the guys are! After some trial and error, I have discovered I really like the softer rails and “flow” of the Pro model. I also like the stability and responsiveness of the higher sidewalls with the full dugout.

That is incredible! The Pro definitely seems like the most popular board choice for Flying Fish team riders! Can you talk to us more about how paddling has changed the course of your life?

Paddling has had such an immense impact on my life. It allowed me to leave my finance career with a purpose and a very specific pursuit in mind. It took me a very long time to have the courage to leave my career. I knew there was no going back if I left and the golden handcuffs can be very compelling. But I knew I was happiest paddling and going to races and being in the paddling community. I felt like you never know how many more days you have and I should do what I love and reconnect with nature while I can. I really think paddling saved my life in a way. I’ve never regretted leaving my career for a second.

What has your journey been like over the past few years, from living full time in New York and being in the financial world to now being in Florida and running a bed and breakfast?

It’s been a wild ride! I knew I wouldn’t last in my career forever. The hours were grueling and while I was good at and enjoyed the challenges of my job, it wasn’t everything to me. Paddling gave me the escape I needed. I wasn’t sure where I would land geographically. I knew I didn’t want to stay in NY full time, especially with the winter. After spending a few months in California in the winters of 2019 and 2020, I decided Florida would be a nice escape, a better fit, and a drivable distance to NY. I stayed for a month in Melbourne Beach in February of 2021 and found myself driving south to Stuart and Jupiter to train with the team many days a week. I decided to look for a house to buy, and after a lot of time on Zillow, I found a fixer upper in a cute little neighborhood in Jensen Beach, which is about 20  minutes north of the Flying Fish factory and 45 minutes to TNRL (Tuesday Night Race League). The built-in community of paddlers has been life-changing. I was always training by myself. Now, I have an entire community to paddle with and it has been incredible! I am a bit of a house renovation addict and I’m just about to start my 4th renovation in Jensen Beach. Last year I bought a tiny little hotel, which I run mostly solo. There have been some fun distractions as well as some personal challenges that have taken me away from training and racing to my full potential, but I feel re-invigorated this year.

Jensen Beach is a beautiful spot! That sounds like a great place to live! What are you looking forward to most this year? For yourself? For Flying Fish? Any goals you have in mind?

I’ve been enjoying getting back to training with a bit more focus this summer. I’m looking forward to continuing to build my fitness and skills. At 49, I keep waiting to fall off the proverbial cliff. Every time I have a bad race, I think “this is it, it’s over. I’m old.” But then, I come back and have a good race and I realize I was just drastically undertraining – I’m not quite off the cliff just yet. My goals right now are to try to stay focused, put the hours in, and most importantly, have fun out there. Every time I race I’m just really grateful to be out there, pushing myself with good people. It’s a privilege I don’t take for granted. As for Flying Fish, it’s been really exciting having Shrimpy come on board. I think it’s a testament to how great the boards are and I’ve really enjoyed seeing our team riders shine over the last couple years; in particular Kim Barnes and Jake Portwood have been getting better and better.

Are you excited for the upcoming ICF World championships to be in Florida later this year? If so – why and what excites you the most?

Yes, I’m very excited. Not having to travel far for a World Championship event is pretty nice! I’m most excited for our entire extended Flying Fish family to gather at the event.

We wish you the best of luck at the World Championships this year! Are you excited for the USA national championships coming up? How are you hoping to place?

I’m definitely excited. I love the venue and Batson really puts on a fun race! I’m just hoping to go out and paddle my best for where I am in my training. Where I place matters less – I just want to give it my all and feel like I raced my best race.

Thanks for taking the time to talk to us today Steph! Before we let you go can you tell us what the stand up paddling community means to you?

It’s everything! I love the paddling community – the adventures I’ve had, the friendships, the physical challenges. I can’t say enough about our local community. We gather almost every Tuesday night for our race league. We push ourselves and then we get to chat afterwards – usually about how our races went and how we can tweak the board design to be better and better. I almost always have someone to paddle with on the other days of the week – most of them are faster than I am which is such a gift. There have been moments out on the ocean in solid conditions, doing a smoking downwinder, and I look around at my friends, most of whom are around the 50-year-old mark, and laugh – this is how we are taking on middle age! It’s such a blessing.

Thank you so much Stephanie for taking the time to share your experiences with us today! We hope that your story continues to inspire others to pursue their passions and keep paddling! We wish you the best of luck at nationals this weekend and the ICF World Championships later this year in November!

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