From Infertility to Entrepreneurship: Building a Business Through Life's Hardest Seasons | Ashley Mastowski

If you've ever felt like you're carrying the weight of your business, your family, and your future all at the same time, this conversation is for you. This week, I'm sitting down with Ashley Mastowski, founder of First Choice Insurance Group, entrepreneur, leader, mom, and someone who knows a thing or two about navigating life's longest seasons of waiting. Ashley has spent nearly two decades in the insurance industry, building a business rooted in education, trust, and protecting families. But her story goes far beyond entrepreneurship. After eight years of infertility, five rounds of IVF, a heartbreaking miscarriage, and countless moments of uncertainty, Ashley and her husband welcomed miracle twins into their family. In this conversation, we talk about building a business from the ground up, leading with trust, finding community during difficult seasons, and what it really looks like to keep moving forward when life doesn't go according to plan.   What You'll Hear: The leap from employee to business owner and what seven years of entrepreneurship has taught her Why collaboration beats competition and how community has shaped her success The leadership philosophy that's helped her build a loyal, empowered team How to trust your instincts when making big business and hiring decisions The reality of building a company while navigating major personal challenges Ashley's eight-year infertility journey, including five rounds of IVF and a miscarriage The emotional moment she learned her final two embryos had become twins Navigating motherhood, entrepreneurship, and leadership all at the same time Why creating a business that supports your life—not the other way around—matters so much The power of vulnerability and sharing your story, even when it's difficult Why high-achieving women struggle to slow down and what Ashley is learning about taking care of herself How community, masterminds, and mentorship can help you through every stage of growth   Connect with Ashley:  Website: https://yourfirstchoice.agency/  Instagram: https://www.instagram.com/firstchoiceinsgroup/