Meet Chasing Red Flags
FOUNDED BY
Teri & Ella Macduff
LOCATION: Needham, MA
THE INTERVIEW
Written by Boston Women’s Market & Teri and Ella Macduff
BWM: Can you tell us a bit about what led you to begin your journey with your business? Was there an aha! Moment?
Teri & Ella Macduff: During an eight-hour road trip in the summer of 2023, my daughter Ella and I opened up to each other about our experiences with red flags in relationships, painful breakups, friendship losses, and the challenges of living with anxiety. Through these honest conversations and the growth we’d both gained from therapy, we discovered a shared passion for helping others prioritize their mental health. That’s when the idea for Chasing Red Flags was born. In January 2024, we officially launched Chasing Red Flags with one guiding belief: being REAL outshines being perfect.
BWM: How have you continued to manage the growth of the company, while also finding time and ways to invest in yourself?
Teri & Ella: We’ve made it a priority to grow Chasing Red Flags in a way that aligns with the values we built it on: authenticity, vulnerability, balance, and connection. That means being intentional about how we work, protecting time for our own mental health, and continuing to do the things that light us up—such as therapy, journaling, long walks, and staying connected with the people who ground us. By investing in ourselves, we show up better for the business and for the community we’re building.
BWM: Our Members are often just beginning to grow their business, and many are interested in learning from other successful businesswomen. What key pieces of insight have you learned from launching your business?
Teri & Ella: Launching Chasing Red Flags has taught us that success isn’t about getting everything right from day one. It’s about showing up, staying true to your “why,” and being willing to learn as you go. We’ve learned to celebrate small wins, ask for help when we need it, and not be afraid to pivot when something isn’t working. Most importantly, we’ve realized that authenticity is our biggest asset and that people connect with people, not perfection.
BWM: With the business acumen you have now, what's one piece of advice you wish you could tell yourself five years ago?
Teri & Ella: Five years ago, we were in a very different place emotionally, and even three years ago. Before launching Chasing Red Flags, we would have told ourselves, 'Don’t wait until you feel “ready” to start; start.' You’ll never have all the answers, and that’s okay. The lessons, connections, and confidence come from taking action, not from waiting for the perfect moment. Trust yourself, lean into the messy parts (no matter how hard), and remember that the most meaningful growth happens outside your comfort zone.
BWM: We think the stories of failure are just as important as the stories of success. Can you talk about a time that you failed in an entrepreneurial venture or objective? How did you face and overcome this failure? What was the lesson learned?
Teri & Ella: In our first few months, we trusted the wrong printing vendor. We liked them personally and assumed that meant they were the right fit for our vision. We didn’t ask enough questions, didn’t use our voice enough, and ended up with a final product that didn’t reflect what we had worked so hard to create. It was a costly and discouraging mistake, but it taught us two big lessons: liking someone personally doesn’t automatically make them the right partner, and your voice matters, even when it feels uncomfortable to speak up. Now, we approach every partnership with clarity, questions, and the confidence to advocate for what our business truly needs.
BWM: Do you have a favorite go-to business tool or resource you can recommend to our members?
Teri & Ella: One of our favorite go-to tools is Canva—we use it for everything from social media graphics to event flyers to mock-ups for new products. It’s affordable, easy to learn, and perfect for creating professional-looking materials without needing a full design team. As a mom-daughter team from different generations, we’ve had to juggle finding tools we both feel comfortable with, and Canva has been that sweet spot for us. And honestly, one of our best “resources” has been our community; asking other businesswomen what’s worked for them has saved us time, money, and more than a few headaches.
