This week,we spoke with Howie Greenspan. He is the Group President, Apparel and Wholesale Clubs, at Steve Madden, has been part of the Fashinnovation’s ecosystem — and someone I’ve had the chance to connect with both inside the Founders Table room and more recently at his office.
Business leader with 25+ years of experience driving revenue growth, market expansion, and operational excellence across consumer brands and high-growth ventures, our conversation was grounded, direct, and very much aligned with what we’re seeing across the industry right now.
What originally drew you to the fashion industry?
I actually started my career on Wall Street, so fashion wasn’t the original plan. What pulled me in was much more personal. I was dating a girl who had started a small T-shirt company called Priorities that took off almost overnight.
She was incredibly creative but needed help on the business side. I took a risk, left Wall Street, and joined her. Together, we built the brand into something special. Over the next 12 years, we grew the business, sold to every major retailer, and eventually sold the company to an overseas manufacturer.
The risk paid off in more ways than one. That girl—Stefani—became my wife, and that journey is what truly launched my career in fashion.
What is one shift or challenge shaping the fashion industry right now that leaders should pay attention to?
One major shift shaping the fashion industry right now is the need for speed and flexibility across the entire product cycle. Trends are moving faster than ever, and retailers expect newness without the long development timelines.
This puts pressure on brands to reduce sampling time, react quickly, and get product right the first time. The challenge for leaders is building teams and processes that can move faster without sacrificing quality or brand identity.
Where do you see the most interesting opportunities for technology or AI in fashion?
The most interesting opportunities for AI in fashion are in speeding up product development and reducing the need for physical samples. Teams can move from concept to visual much faster, allowing for quicker alignment and earlier decisions.
There’s also a big opportunity in creating realistic product imagery before production, helping sell ideas sooner. Overall, AI is most impactful where it helps brands move faster, cut costs, and reduce risk.
What advice would you give to founders building fashion or fashion-tech companies today?
Focus on speed, clarity, and discipline in your product. The brands winning today are the ones that can move quickly, react to what’s working, and avoid carrying too much inventory. Stay extremely close to your customer and retail partners, listen to what’s actually selling, not just what you think should sell. Small, smart bets will take you much further than big risky ones.
Also, keep your operations tight from day one. Clean costing, strong vendor relationships, and reliable delivery matter just as much as great design. Finally, don’t overcomplicate it, great product at the right price, delivered on time, still wins.
One book, one leader, and one quote that inspire you.
Book: The Let Them Theory
I like it because it’s a simple but powerful reminder to stop over-controlling outcomes and focus my energy on what I can actually control.
Leader: Steve Madden
For building a brand that turns speed and instinct into a competitive advantage, consistently staying ahead by acting quickly and trusting the market.
Quote: “Success usually comes to those who are too busy to be looking for it.” — Henry David Thoreau
