Andrew Rosen Built Theory and Backed SKIMS – Here’s What He’d Tell Every Founder

September 15, 2026

AI Summary

5 min read

Andrew Rosen didn’t set out to become the most networked person in American fashion. He started in a knit mill on Long Island at nineteen, worked on a sewing floor in Massachusetts, and learned to read a garment from the inside out. By twenty-six, after his father died, he was CEO of a New York Stock Exchange company. By thirty, he had been fired from Ann Klein. By forty, he founded Theory. Along the way, he invested in SKIMS before it had a name, backed Good American before it had a product, and became the kind of investor founders call when they don’t want to hear what they want to hear.

The only way to learn is to do everything

Rosen’s operating system was built in his father’s factories. He did not study fashion in a classroom. He worked in a warehouse, on a sewing floor, in a showroom, and eventually in the CEO’s office. That full-spectrum experience is, in his view, the only reliable teacher. “What’s taught me the most is being involved in doing everything that a founder is doing every day,” he says. “Selecting fabrics, manufacturing, retail, dealing with customers, dealing with wholesale accounts.” He believes that founders who skip the operational depth and try to scale too fast miss the signals that keep a business alive.

Survive first, then plan

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What you'll learn

1 (00:09) **Introduction to Andrew Rosen** - Emma Grede introduces Andrew Rosen as a mentor and one of the most influential figures in American fashion.
2 (04:02) **Andrew’s First Meeting with Emma** - Andrew recounts their first meeting, where Emma tried to pitch him on celebrity/influencer marketing and he dismissed the idea.
3 (07:35) **What Teaches You About Business Success** - Andrew explains that being deeply involved in every facet of the business — fabric, manufacturing, retail, wholesale — is what taught him the most.
4 (08:57) **Advice for Ambitious Founders** - Andrew advises founders to set their sights on three to six months, not years, and to focus on survival first.
5 (11:23) **Listening to the Customer** - Andrew tells Emma she must listen to her customer because she needs to address their feedback in the next season.
6 (12:36) **Andrew’s Early Career and Father’s Influence** - Andrew describes growing up in a three-generation fashion family and being groomed to take over the business.
7 (14:50) **The Calvin Klein License and Early Success** - Andrew recounts getting his father’s license to make Calvin Klein jeans at age 22 and growing the men's business to $100 million in three years.

+ Full timestamped outline available in the app

Show Notes

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