Regina Sunderland, a digital business strategist and mentor, is the founder of Start With Regina and Start To Succeed. These platforms offer guidance to professional and busy mothers, helping them transition from stressful routines to successful digital entrepreneurship, even without prior business experience or technical skills. Regina’s approach focuses on providing mentorship and a user-friendly digital system that supports women in creating online businesses that provide flexibility, financial independence, and a sense of purpose.
Born in the Philippines, Regina’s early life was shaped by challenges. Growing up in a developing country, she moved abroad as a foreign worker to support herself and her family. Over three decades, she worked as a caregiver and mental healthcare professional, balancing multiple jobs in different countries before settling in Canada. Like many immigrant women, Regina faced personal and professional challenges, often sacrificing her time, health, and peace of mind to provide for her family in both Canada and the Philippines.
Despite her dedication, Regina struggled with feelings of self-doubt and low self-esteem. She faced language barriers and the pressure to succeed in a foreign land, often feeling overwhelmed by the demands of multiple jobs that only barely covered her expenses. Over time, the physical and emotional toll of balancing these responsibilities led her to a breaking point.
In 2019, a pivotal moment changed her life. Her elderly mother in the Philippines fell seriously ill, and Regina found herself unable to be by her side due to the limitations of her job. This moment of frustration, combined with the emotional and physical strain of her work, led Regina to reconsider her situation. She realized that working long hours for insufficient pay was not the path to fulfillment and wanted to find a smarter, more sustainable way to live, earn, and support her family while regaining control over her time and financial stability.
This moment marked the beginning of Regina’s transition into digital entrepreneurship. From this need for change, Start With Regina was born, followed by Start To Succeed—a business partnership program tailored for women who feel stuck in a routine of survival. These platforms provide a step-by-step system that enables women to create online businesses from the comfort of their homes, offering an opportunity to regain control over their time, finances, and sense of self-worth.
Regina’s brand focuses on values and emotional empowerment, with a strong emphasis on mentorship. The programs are designed to help women not only navigate business strategies but also address the mental and emotional barriers that often prevent success. By offering user-friendly tools and mentorship, Regina’s system provides a clear path for women to start their online businesses, whether it’s through launching blogs, creating online stores, or setting up automated marketing systems.
I know what it feels like to be overwhelmed and unsure where to begin,” Regina says. “My business partners and I provide access to our system, tools, and global support because we’ve been there. Let’s face it: most of our lives are spent working for others, building their dreams while putting our own aside. Yet, when we can no longer work, everything can be lost. Our jobs aren’t truly ours. Others hold significant power over our lives, our children’s futures, and our retirement. We spend decades trying to break through, but the reality is, working alone is not security—it is survival. It means trading your time, health, and dreams for a paycheck that stops the moment you do.
That is why we offer business partnerships—to help women rise from burnout to breakthrough.”
One of the key aspects of Regina’s approach is simplifying the business-building process. The programs are designed to be accessible, even for those with no technical experience, and aim to have participants up and running in as little as two weeks. Beyond the business tools, Regina’s mentorship program offers emotional support, focusing on helping women overcome self-doubt and build the confidence needed for entrepreneurial success.
A distinguishing feature of Regina’s approach is the sense of community she fosters. The Start With Regina and Start To Succeed programs go beyond business building—they create a network of like-minded women committed to personal growth and entrepreneurship. With lifetime access to a global support community, participants can share experiences, learn from each other, and celebrate their achievements together.
Regina’s target audience is women over 40, especially those who may not be tech-savvy but are eager to embrace a new chapter in their lives. Many of her clients are former healthcare workers, overworked professionals, or mothers who have spent years working abroad and missed out on family time. Through Regina’s mentorship, these women can transition into business ownership and create a more flexible, meaningful lifestyle that aligns with their values and goals.
“We are building a community of women ready to take a fresh start,” says Regina. “Your dreams are within you—you just need the right guidance and support to bring them to life. This is your chance to break free from the ordinary and step into a life of purpose.”
Regina’s mission to empower women over 40 and 55 has touched the lives of many who have made transformative changes in their careers and lives. By providing accessible systems and emotional mentorship, Regina’s platforms are helping women around the world build businesses that align with their personal and professional aspirations.
Regina’s story is one of resilience and transformation. From a struggling foreign worker to a thriving digital entrepreneur, she proves that it’s never too late to start over. Her journey underscores the power of mentorship, determination, and the belief that women deserve to live lives full of purpose and abundance.
For those interested in exploring digital entrepreneurship, Regina’s programs offer the tools, mentorship, and community support necessary to succeed. Her guidance is helping women break free from the constraints of their current situations and build businesses that provide financial freedom and time flexibility, all while making a meaningful impact.
To learn more about Regina’s mentorship programs and how to get started with your own digital business, visit her social media profiles:
Facebook – Start With Regina
Facebook – Start To Succeed
YouTube – Start To Succeed
YouTube – Start With Regina
TikTok – Start With Regina
Instagram – Start With Regina
Regina Sunderland is a mentor and advocate for women looking to create businesses that support their lifestyle and goals. Her story proves that through mentorship and community, women can overcome challenges and achieve success on their own terms.
