A Conversation with Cassie Winterowd

Welcome back to Time-Tested Mastery: Life Lessons Sell! In this interview, we sat down with Cassie Winterowd of M5 Financial, an industry expert in mortgage lending who has built her success through resilience, adaptability, and a deep commitment to personal and professional growth. Her journey from an aspiring anthropologist to a top-performing lender is an inspiring story of perseverance, mindset shifts, and learning from setbacks.

The Myth of Perfection: Mastery is a Process

Cassie opened the conversation by addressing a common mistake many people make—striving for perfection. She shared that she once fell into the trap of expecting major life changes to happen overnight, only to realize that mastery is about incremental progress. Whether it’s goal setting, professional growth, or personal development, she emphasized the importance of focusing on one change at a time and allowing space for learning through mistakes.

“Everybody makes these big changes at the beginning of the year, and most of them fail. The best thing you can do for yourself is to be easy on yourself. Take one thing and master it.”

The Unexpected Path to Mastery

Cassie’s journey into mortgage lending wasn’t planned—it happened by accident. Originally pursuing a degree in anthropology, she realized fairly quickly that it wasn’t the right fit. Instead, she took an administrative job in a mortgage company, where she was exposed to the industry’s fast-paced environment. Over time, she absorbed knowledge from top-performing loan officers and realized she had the skillset to thrive in the industry herself.

This pivot underscores a valuable lesson: sometimes our greatest opportunities arise from the unexpected.

Thriving in a Changing Industry

Mortgage lending, like many industries, experiences cycles of boom and bust. Cassie recalled witnessing the 2008 financial crisis, watching companies implode, and navigating market downturns. Instead of panicking, she took these moments as opportunities to learn and grow.

“I didn’t have any wrinkles before then, but I got my first forehead wrinkle during that time.”

Her ability to stay calm and focused during times of uncertainty is what sets her apart. She emphasized that success in any industry requires embracing change and constantly refining skills to stay relevant.

Empathy and Mastering Client Relationships

A standout quality in Cassie’s approach is her emphasis on tactical empathy—understanding her clients’ emotions without letting emotions dictate the process. She recognizes that buying a home is one of the biggest financial decisions people make and that clients often feel vulnerable during the process.

“Trust is one of the most important things you can establish. I always put myself in the client’s shoes and make sure they feel like I’m in it with them.”

The Power of Goal Setting and Continuous Learning

Cassie follows a structured approach to goal setting, dividing her focus into the Four Fs: Family, Fun, Finance, and Fitness. This balanced framework ensures that while she excels in her career, she also prioritizes her family and well-being.

She is also a firm believer in lifelong learning. From informal mastermind groups with her peers to industry newsletters and business books, she actively seeks out knowledge that will help her grow.

The Psychology of Influence: Prospect Theory in Sales

One of the most fascinating takeaways from our conversation was Cassie’s application of Prospect Theory—a behavioral finance concept that suggests people are more motivated to avoid loss than to achieve gains.

Instead of asking a prospect, “Are you still looking to buy a home?”, she now asks, “Have you given up on buying a home?” This subtle shift makes clients more likely to engage and clarify their intent, demonstrating how small psychological tweaks can create better outcomes in business.

Final Thoughts: Embrace the Journey

• Embrace change—it’s the only constant in business and life.
• Master one thing at a time—small wins build confidence and momentum.
• Keep learning—seek out mentors, books, and mastermind groups.
• Trust the process—failures are simply steppingstones to growth.
• Prioritize relationships—whether with clients, partners, or family, trust is the foundation of lasting success.

If you’d like to connect with Cassie, you can reach her at cassie.winterowd@m5financial.com or 858-999-1778.