Celebrating Women Business Owners
As business owners, we’re always looking for ways to work smarter. And yes, this predates AI!
It’s learning through connections and relationships. Finding people who inspire you.
This year, we’re celebrating women business owners who we think you’d like to meet. They’re inspiring, dynamic, brave, resilient and authentic.
This is an expanded version of content from our July 2026 newsletter.
Angela’s Charter Service
Our first profile is Angela Motola owner of Angela’s Charter Service.
I originally started Angela’s Charter Service when my daughter was young and I was a single mother looking for a way to create financial stability while building something meaningful of my own.
Before entering the yacht charter industry, I worked in corporate America. I enjoyed many aspects of the corporate environment, but I was drawn to creating experiences and connecting people.
What fascinated me about the charter business was that it brought together two worlds that don’t often intersect. On one side were executives, entrepreneurs, and professionals conducting business. On the other were celebrations, friendships, families, and life milestones. The common thread was people coming together.
Dealing With Challenges, Building Connections
I saw an opportunity to create experiences that allowed people to connect in a way that doesn’t happen in conference rooms, restaurants, or through a screen.
Chicago’s skyline and waterways provide an incredible backdrop, but the real value is creating an environment where people can slow down, be present, and enjoy each other’s company.
Over the years, I’ve welcomed guests from different cultures, industries, and countries.
While people may come aboard for different reasons, I’ve found that the things people value most are remarkably similar: meaningful connection, beautiful surroundings, good food, shared experiences, and time spent with people they care about.
And then there’s yoga…….
That same desire to help people connect and grow eventually led me to become a yoga and fitness instructor.
Whether I am leading a class, coaching someone through a life transition, or hosting guests aboard a yacht, the goal is the same: create an experience that helps people feel more connected, empowered, and engaged in their lives.
Staying Focused Despite Constant Change
One of the greatest challenges of entrepreneurship is learning to navigate constant change while staying focused on your long-term vision.
I’ve operated through economic downturns, changing consumer behavior, advances in technology, shifts in marketing, and evolving customer expectations.
Business owners are expected to be marketers, salespeople, customer service representatives, financial managers, problem-solvers, and leaders all at once. In the charter industry, those responsibilities are compounded by the logistics, maintenance, regulatory compliance, staffing, and operational demands of a commercial vessel carrying guests safely on every voyage.
Another challenge is balancing growth with presence. We live in a society that is more connected through technology than ever before, yet many people feel increasingly disconnected from one another. As business owners, it’s easy to become consumed by emails, social media, notifications, and endless responsibilities while losing sight of what truly matters.
I’ve learned that success isn’t about doing everything. It’s about maintaining clarity, adapting when necessary, building strong relationships, and staying committed to the purpose behind what you’re creating.
Taking Pride In What I Do
I’m proud that my work has never been solely about chartering yachts or teaching fitness classes. It’s always been about creating opportunities for people.
Whether it’s helping a company strengthen relationships with clients, providing a memorable experience for employees, celebrating a family milestone, supporting local vendors, employing crew members, helping someone improve their health through fitness, or guiding students through a yoga practice, the common thread has always been connection, growth, and creating positive experiences.
There are many parallels between operating a charter business and teaching yoga and fitness. In both, people arrive carrying stress, distractions, responsibilities, and expectations.
My role is to create an environment where they can be present, connect with others, gain a new perspective, and leave feeling better than when they arrived.
After more than three decades in hospitality, events, fitness, coaching, and the charter industry, I’ve watched Chicago grow and evolve. I’ve witnessed businesses succeed, industries transform, and countless people come together to celebrate, collaborate, and build relationships.
Through it all, I’ve remained passionate about creating experiences that help people connect with themselves, with one another, and with their community.
Relaunching the Gypsy Spirit
Today, I am especially proud to be relaunching Angela’s Charter Service aboard the Gypsy Spirit at Navy Pier.
Building a business requires courage. Rebuilding one requires even more.
This chapter represents not only a new beginning for the company, but a renewed commitment to creating exceptional experiences while contributing to the vitality of our city and the people who make it special.
Contact Information
Angela Motola, Founder & Charter Experience Director Angela’s Charter Service, Inc.
877-751-7175
info@angelascharters.com
Note: Rickey and Iris have enjoyed many wonderful charters on the Gypsy Spirit — special events, Girls Nights Out, Tall Ships viewing, fireworks cruises and more. There’s no better way to enjoy Lake Michigan. And Angela is an amazing host.