START UP INTERVIEW SERIES: Meet Anna Yoshitsugu at Wolilo
In the final startup interview of 2025, our team sat down with Anna Yoshitsugu, co-founder of Wolilo, to discuss her motivation to innovate and the ways our WIN community has helped to facilitate that process. Wolilo, an adult learning platform that focuses on teaching practical skills, is Anna’s approach to using technology to boost not only productivity but communication, networking, financial literacy, and habit-building.
Anna is the co-founder of Wolilo, an educational company for busy professionals. She comes from a background in consumer packaged goods and tech, having worked at companies like Coca-Cola and Uber, where she launched new products across Europe and North America. She’s building Wolilo to help people understand what’s happening in the world and get ready for the future, and we couldn’t agree more!
What’s the story behind Wolilo?
I’ve always loved learning, but after university I found it increasingly difficult to carve out time for self-development. With so much happening in the world, it’s hard to keep up, let alone learn and actually apply new skills. At Wolilo, our goal is to identify the most important skills and knowledge people need right now and in the near future: from AI for daily productivity, to communication and networking, financial literacy, resilience, and habit-building based on the latest longevity and neuroscience research.
Today we offer three ways to start learning with us: in-person events in NYC, online masterclasses, and online bootcamps where experts teach, guide, and provide personalized feedback. My next goal is to integrate AI to amplify what our experts deliver, making the learning process even more customized and ensuring people can implement what they learn in real life.
How did you know what you wanted to innovate and what was your aha moment?
I always felt there was a clear gap in the adult education market. Some EdTech companies focus on engagement with beautiful production, great UX and gamification, but they often lack real effectiveness. Others provide deep knowledge, yet completion rates are low, especially in online learning. Most adult education companies concentrate on corporate training or technical skills, while we focus on people who want practical skills for life beyond work, so they feel ready for whatever comes next.
I want to build a place that brings together experts, technology and community. I’m still at the beginning of this journey and excited for what’s ahead.
What were the biggest challenges you faced when getting your company off the ground?
One of the biggest challenges for me was shifting my mindset from large corporations to the fast-paced startup world. In big companies, you have a solid budget, many teams of talented people supporting you, and plenty of resources to make a project succeed. The risk of failure exists, but it is relatively low. When you build your own startup, failure becomes a natural part of the process, especially in the beginning. We are currently testing multiple hypotheses and some of them do not work, but each one helps us understand our customers, their motivations and their needs.
If you could go back and change something, what would it be?
I would start building small projects and businesses earlier in my career, even as side hustles or volunteer initiatives. It would have helped me learn how to create something from scratch, adapt quickly and make progress with a limited budget.
I used to believe that you needed experience in top companies before starting your own business. While corporate experience teaches valuable skills like project management and stakeholder or team management, it does not always teach you how to innovate when you have very few resources.
What is one thing you’d tell someone looking to start their first venture?
Be prepared for the journey ahead of you, but don’t wait until you feel fully ready. You can never be prepared for everything, but it truly helps to have your mindset in a good place, your finances and savings organized, and supportive people around you. Building a strong environment around yourself is essential for long-term goals, and communities like WIN make a real difference because they bring together people who face similar challenges.
How has the WIN ecosystem impacted you?
I am very glad to be part of the WIN ecosystem and genuinely grateful to be recognized as a Mover and Maker. I’ve met incredible women along the way and felt supported and inspired throughout this journey. I’m especially thankful to Amanda Ramos and the entire WIN team for their guidance as I navigate the transformation from a corporate professional to a business leader.
How do you see your company connecting with the WIN ecosystem in the future?
I would love to co-host events and workshops on innovation for women in NYC, and eventually co-create a course on different aspects of innovation, from creative thinking and innovative mindset to practical tools that help bring an idea to life. I’m also excited to explore ways to engage more deeply in the WIN entrepreneurship ecosystem by learning from women leaders further along in their journeys and creating internship opportunities for junior colleagues.
If you’re interested in joining on this journey, follow @wolilo.galaxy on Instagram