Today we’d like to introduce you to Helaine Knapp
Hi Helaine, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
My entrepreneurial journey is probably not what you’d expect. I was actually that shy kid who wore a paper bag over her head when guests came over – literally, not metaphorically. Growing up overweight and insecure, I was always the outsider trying to find my place. But those early experiences shaped my ability to observe, solve problems creatively, and eventually lead with empathy.
After college at the University of Michigan, I landed in NYC’s tech startup world, working at companies like Buddy Media (acquired by Salesforce) and Olapic. I was thriving in sales and account management, but also falling in love with boutique fitness. After years of struggling with my weight, I’d finally found my groove, booking classes with friends and taking clients to workouts.
Then my back started giving me trouble. The doctors told me to find something low-impact – no more spinning, dance cardio, or running. When my trainer suggested rowing, I initially rolled my eyes. I thought rowing was for Winklevoss-type guys or CrossFit bros – not me and my SoulCycle crew. But as I researched it, I discovered something fascinating: rowing works 85% of your muscles and is incredibly efficient. I saw an opportunity no one else seemed to see.
In 2013, I launched CITYROW while still working my tech job, pioneering the concept of a boutique rowing workout that combined rowing intervals with strength training. Ironically, six weeks after opening our first studio, I ended up having emergency back surgery – nothing says “I’m ready to be a fitness CEO” quite like not being able to walk! But that experience reinforced what would become our core mission: creating smart, effective workouts that are sustainable for life.
Over the next decade, we grew from one NYC studio to a national brand combining brick-and-mortar studios, digital fitness, and connected hardware. We weathered countless challenges – from early lawsuits to COVID-19 – ultimately raising millions in venture capital and being acquired by our long-term partner WaterRower in 2024.
Today, I work as a keynote speaker, business strategy consultant, and advisor, helping other founders and executives navigate their own waves of change and uncertainty. The shy kid with the paper bag became someone who helps others find their confidence and resilience. It’s not the journey I expected, but I wouldn’t have it any other way.
My story shows that sometimes your biggest setbacks create your greatest opportunities – if you’re willing to ride the wave.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Smooth? [laugh] Building CITYROW was like navigating a decade of tidal waves. While we had incredible successes, the challenges tested every fiber of my being.
We got hit with a lawsuit within four days of opening our first studio over noise complaints. When we opened our second location, the floor literally turned into a waterbed due to flooding, forcing us to close for six weeks. These are the kinds of challenges they don’t teach you about in business school.
The real tests came during COVID-19. We had to close our studios overnight, with record-breaking pre-sales for new locations about to open. While our digital business thrived during the pandemic, our franchise partners were fighting for survival. Having to support them while maintaining a brave face was one of my hardest leadership challenges.
The fundraising journey was particularly grueling. Despite building a strong business, we didn’t fit neatly into investor categories – we were part brick-and-mortar, part tech, part hardware. I heard “no” hundreds of times. There were months where I couldn’t pay myself, let alone my team. The highs of closing our Series A were quickly followed by having to let go of 75% of our staff as market conditions changed.
Perhaps the hardest part was the emotional toll. As a founder, you’re expected to always project confidence and strength, even when you’re barely holding it together. I remember having to go from sobbing through a board meeting to appearing on live TV 30 minutes later with perfect hair and a huge smile.
But here’s what I learned: resilience isn’t about avoiding the waves – it’s about learning to surf them. Each challenge made me stronger and ultimately contributed to both my personal growth and the company’s success. Today, I’m grateful for every struggle because they’ve given me the experience and empathy to help other founders and leaders navigate their own challenges.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
After a decade of building CITYROW from concept to acquisition, I now work as a business strategist and advisor, helping founders and executives navigate their own waves of change and uncertainty. My work spans several key areas: I serve as a fractional executive helping companies through critical growth phases, sit on boards, deliver keynotes on leadership and resilience, and provide focused coaching to founders, executives, and teams.
What sets me apart is that I’ve recently lived the full founder journey – from side hustle to Series A to acquisition. I understand firsthand the challenges of building an omnichannel business, managing complex stakeholder relationships, and leading through crisis. When I work with clients, I bring not just the highlight reel but the raw, practical lessons from both successes and setbacks.
I specialize in helping leaders and teams navigate pivotal moments in their business – whether that’s fundraising, scaling operations, managing through crisis, or preparing for exit. My approach combines strategic thinking with practical execution, always focusing on what’s actually feasible with available resources. As a coach, I help teams work better and smarter together, building the trust and resilience needed to achieve ambitious goals.
What I’m most proud of is my ability to help others find their resilience and confidence as leaders. Having gone from the shy kid wearing a paper bag over my head to leading a national brand through unprecedented challenges, I understand the personal growth journey leadership requires. I love being the advisor I wish I’d had during my early days – someone who’s recently been in the trenches and can provide both strategic guidance and emotional support.
My recently launched book, “Making Waves,” captures many of these lessons and provides a raw, honest look at the entrepreneurial journey. Whether through speaking, consulting, or advising, my mission is to help others navigate their own waves of change and uncertainty with clarity and confidence.
We love surprises, fun facts and unexpected stories. Is there something you can share that might surprise us?
Despite being known as a fitness founder, I spent my early years struggling with my weight and feeling like an outsider. What might really surprise people is that I was incredibly shy – so shy that I literally wore a paper bag over my head when guests came to our house. The idea that I’d go on to be a CEO, much less a public speaker, would have shocked anyone who knew me then.
I also never set out to be in fitness. When my trainer first suggested rowing after a back injury, I completely dismissed it as “something my grandpa did in his basement.” That resistance to an idea before completely embracing it has become a pattern I now recognize – sometimes our biggest opportunities come disguised as things we initially reject.
But perhaps what surprises people most is that while CITYROW’s acquisition looks like a classic success story from the outside, the journey was far from smooth or traditionally successful. In fact, it was so raw and full of unexpected challenges that I wrote a book about it. “Making Waves” reveals the real story – the sleepless nights, the tough decisions, the tears before TV appearances. Success stories often look different from the inside, and I believe sharing that reality helps other founders feel less alone in their struggles.
Contact Info:
- Website: https://www.helaineknapp.com
- Instagram: @helaineknapp
- LinkedIn: https://www.linkedin.com/in/helaine-knapp/
- Other: https://a.co/d/8hQPUAm
