Diane von Furstenberg created the iconic wrap dress in her twenties and built her namesake company DVF into one of the most recognizable fashion brands in the world. More than fifty years later, as she approaches 80, she's entering a new chapter — with a lifetime of lessons to share.

In this episode of Aspire, Emma sits down with her longtime friend and idol for a deeply personal conversation about self-belief, independence, motherhood, aging and becoming the woman you want to be. Diane opens up about the choices she made as a working mother, why guilt and fear are not options, the mistakes she's made along the way, and what it takes to like the person you've become.

Diane shares:

• How to build the kind of self-belief that carries you through every stage of life
• Why the most important relationship you'll ever have is the one you have with yourself
• How to stop comparing yourself to other people and own who you are
• Why guilt and fear should never drive your decisions
• What motherhood taught her about raising independent children without losing yourself
• Why independence has always mattered more to her than money
• How to learn from mistakes without letting them define you
• Why kindness is a currency — and how it compounds over time
• What getting older has taught her about confidence, clarity and becoming more yourself

On this special birthday solo of Aspire, Emma Grede shares 44 rules for life, business, and success—her personal operating system for nearly everything. This is everything she knows to be true about money, work, marriage, and motherhood, plus the beliefs she actually uses to make decisions, build companies, and recover from her mistakes.

In this episode, you’ll learn:

• Why taking responsibility for your life is the biggest power move you'll ever make
• How to build confidence before you feel ready
• The question that exposes whether your full schedule is progress or avoidance
• Why you should ask for more money before resentment sets in, and how to do it
• The case for treating your choice of partner as the biggest business decision of your life
• What most successful people get wrong about happiness
• Why your reputation is built when there’s no immediate reward

Andrew Rosen has spent nearly five decades building, investing in, and shaping some of the most influential brands in American fashion. As the co-founder of Theory and an early investor in brands like TWP, rag and bone, Veronica Beard, Alice + Olivia, Good American and SKIMS, he’s also one of Emma's closest mentors. His advice comes from doing the work — and learning what happens when things don't go to plan.

In this conversation, Andrew shares the lessons he took from his father, the setbacks that shaped how he built Theory, and the advice he gave Emma when she was becoming a brand owner. They explore how to trust your instincts, choose the right investors, and build a profitable business with staying power.

They get into:

• Taking over as CEO of the family business in his twenties
• Losing control of the company — and what he did next
• Getting fired, and why he never saw it as failure
• The experience he brought to starting Theory at 40
• Why profitability has to be part of the plan from the start
• What founders should actually look for in an investor
• The lessons he took from his father that still shape how he does business