Jill Layfield is co-founder and CEO of fashion startup Tamara Mellon. Together they’ve raised tens of millions of dollars to empower women with a new direct to consumer apparel brand.  

I had the great opportunity to interview Jill on a recent episode of the Dealmakers podcast. We talked about the fun and challenges fashion startups, staying ahead of the competition, curating company culture, raising a Series C round, and the importance of storytelling.   

Listen to the full podcast episode and review the transcript here.  

What’s Your Story?  

Layfield had a great opportunity to be born in San Jose, California. An environment that seems to make the impossible possible.   

After spending time growing up in Austin, Jill returned to Cupertino for high school. Then it was onto Santa Clara University to study communications and journalism. Something she wishes she could go back and continue to learn, to become a better writer and storyteller for business.   

It’s an invaluable skill for connecting with customers, your board, employees, and investors. Far more so than just being able to put together bullet points and slides for a PowerPoint. It’s the writing that compels results.  

Determined to be self-sufficient as soon as possible, she paid her way through college by waiting tables at Birk’s in Santa Clara.   

There she met the team from 8×8. They offered her an internship in their Silicon Valley voice over IP technology company. Then a full-time gig after university.   

These connections led to her meeting Jim Clark (Netscape and Silicon Graphics), who recommended she joined a new company called Shutterfly. A small team of just around 50 people at the time.   

Then falling in love with rock climbing and finding a husband, Jill made the big leap to go out to Park City, UT. She found a gig at a small eCommerce company in a ski resort. They ended up being BackCountry.   

She stayed with them, growing the company from $20M to $500M and moving up to COO, President, and CEO and an acquisition.   

Staying Fearless  

It’s competitive out there. No business can just rest on their laurels today.  

It’s something Jill Layfield quickly found out as CEO of BackCountry. They were doing great at attracting online traffic. The conversions just weren’t coming through. Then they were hit with one of the warmest and driest winters on record. Not a great scenario for a winter-weather dependent business.   

Backcountry had also benefited from bringing an industry online. But, now Amazon and others were aggressively pursuing the category as well. Needless to say, there were night sweats and tough decisions to make.   

Jill lead the company through three things:  

  1. Differentiation: Finding what they could uniquely own in the market and delivering what matters most to the customer

  2. Telling New Stories: Bringing new customer and product stories to life in digital

  3. Overhauling the Team: Bringing in a whole new tech, product, marketing and management team to be the company they needed to be to win


Finding A Foothold In Fashion
 

As with most true entrepreneurs, there comes a time when the company hits a certain level of maturity where you just don’t feel the shoe fits anymore. Jill had already been CEO, so she couldn’t move somewhere else as a CMO, CTO, or CFO.   

It was then NEA suggested she would be a good fit for an early-stage company. She met Mark at Jet and Gwyneth at Goop. Then she was introduced to Tamara Mellon, former co-founder of Jimmy Choo.  

Tamara was on a mission to disrupt the luxury footwear industry. She needed tech and eCommerce, savvy co-founder. They met. They hit it off. Jill moved her family to LA so they could work together.  

They set out to build a fast-growth brand that went direct to the consumer. They created a disruptive force that made shoes in the same Italian factories as Jimmy Choo, Manolo, and Louboutin, without the 6x markup for retailers. They broke the fashion calendar and deliver new product weekly instead of twice a year.  

They discovered a big innovation opportunity on the backend of the business in an antiquated supply chain.   

Every Great Company Almost Runs Out Of Money At Least Once  

When you are doing new things and growing fast, you’re also burning money in upfront investments. Jill says when they closed their Series C round in mid-2019, they may have had only $50,000 left in the bank. They’ve now raised a total of close to $90M. Their Series C was oversubscribed by at least $15M.   

Storytelling is everything which is something that Jill was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

Jill’s key takeaways from startup fundraising:   

  • It’s always going to take longer than you think
  • No matter how great you are, you will hear many no’s
  • Spend a lot more time on writing the story
  • Write the story before you try to design a single slide
  • Make sure you connect with investors on what they get and want to invest in

If you are launching and fundraising for your own startup, Jill Layfield recommends blocking out more time to be thoughtful, instead of just burying yourself in the weeds.   

She says blocking out those 30 to 60 minutes to sweat and exercise each day will give you more energy and clarity. Use that to get back to crafting the story and writing.   

Listen in to the full episode to learn more, including:  

  • Ways to communicate more powerfully
  • Building a brilliant brand culture
  • Why you are going to hate bankers
  • Building and scaling a business that will survive and thrive

 

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