About Us

Sailwinds Financial Strategies was founded in 2016 by Bernadette "Bernie" Strout, though the roots go back further. The name comes from Bernie's sailboat—and later, the software company she built during a career in technology before transitioning to financial services more than 21 years ago.

That technical background isn't just a blip on the radar. Bernie holds two software patents, including work on pattern recognition and self-teaching systems that predated today's AI. That same analytical mindset—visualizing complex problems, identifying multiple solutions, and translating them into actionable plans—shapes how we as a firm approach financial planning today.

From the beginning, Bernie practiced holistic wealth management: focusing on investment returns while also integrating taxes, income, protection, and legacy into one cohesive strategy. That approach was ahead of its time, and one that remains central to everything we do.

Bernie was also a co-founder of the Gay Pride Business Network in Asbury Park, New Jersey, around 2005, driven by the belief LGBTQ+ individuals deserve a unique space in commerce, and that people prefer to do business with people they like, know, and trust. That principle still guides the way we build relationships with our clients, many of whom have been with us for years and have become genuine friends.

Sailwinds is now entering its next chapter as a family firm, with Bernie bringing on her nephew, Jack Strout, to carry the work forward. Together, they’re committed to helping clients across New Jersey and beyond live more confident, fulfilling lives through wealth managed smarter.