Play It Forward: Lunch & Learn with Gymboree’s Joan Barnes

We recently had the pleasure of welcoming Joan Barnes, Founder and former CEO of Gymboree, former principal owner of YogaStudio, and author of “Play It Forward” to speak at Stitch Fix.  Joan shared with our team her experience founding and building, her personal and professional challenges, and the many tough decisions she faced along the way.

When Joan founded Gymboree in 1976, she was a female entrepreneur starting a business and raising capital at a time when it was exceedingly rare.  Joan was an early example of what is possible, and she played a big part in paving the way for entrepreneurs like myself.  

Joan spoke passionately about being able to provide women with employment opportunities through her business. This really resonated with me; the pride of creating thousands of jobs has been undoubtedly one of the most rewarding parts of the Stitch Fix journey.


A thought-provoking point of view that Joan shared was that women can’t expect to ‘do it all’. She shared her belief that the art of life is not about striving to have it all at once, but instead trying to many joys at different times. I found her perspective on the topic a refreshing alternative to the current chorus I experience of convincing women that we can and should try to have it all.

I won’t spoil too much from her book, but Joan very honestly shared about some of the leadership and personal challenges that she faced.  To hear speak so candidly to us about mistakes she made, a potential acquisition gone south, parting ways with a leadership team she deeply cared for, and an eating disorder she battled – her humility and authenticity was truly inspiring.

If you are interested in learning more about Joan and her experience, check out this clip from the Today Show and grab a copy of her new book, “Play It Forward.”

Shoptalk: New Retail Business Models

A couple of weeks ago I spoke at the Shoptalk Conference in Las Vegas where leaders in ecommerce and traditional retail gathered to “talk shop.”  It was really well attended, with 3,000 attendees, 300 speakers, more than 150 CEOs and leaders from Westfield, Honest Company, Birchbox, Bonobos, Chloe + Isabel, Sephora, and many, many more.

I sat down with Ryan Mac of Forbes, where we discussed new retail business models in general and what in retail needs to be ‘Fixed.’  Ironically, a lot of the inspiration for Stitch Fix actually originates from the high level of service that retailers are finding difficult to deliver in stores today’s environment of cost-cutting and decline comp store sales. Ryan and I discussed our approach to personalization at Stitch Fix – blending art and science and a strong and large data science team to enable scalable 1:1 personalization.

Data was also a theme we covered – in fact data was a pervasive theme in the conference in general.  We talked about the difference between big data and what we call ‘small data’, and the benefits of partnering with your customer to help make his or her experience better.  If you can gain the trust of your customer, being able to simply ask him or her what she’s looking for and how we can serve her better provides much more high-signal, actionable, and less ‘creepy’ data compared to the huge data sets of search behavior for example.  Easier said than done perhaps, but we are a big believer in the value of the trust we have with our clients and how we’re able to help make her Fixes better through that bond.

Over the course of the conference, some key themes I noticed were:

  • Big Data.  Trying to better understand customers and what they want to buy was a clear theme.  What was once just online tracking has broadened and expanded – some are experimenting with tracking movement in stores, incorporating weather, social media signals, and using this data to personalize the offers and assortment that customers see.  
  • Omnichannel powered by mobile. Conversations centered on innovations of new app experiences, how to leverage mobile around showrooming, and of course beacons everywhere to drive customers to new experiences in the real world.
  • Personalization. Speakers that discussed personalization emphasized the personalization of marketing, client acquisition, and ad targeting as opposed to the personalization of a customer’s experience of a brand or product. Figuring out how to personalize loyalty programs for example, around perks that really matter was an interesting concept I’m excited to keep an eye on.  
  • Brick and Mortar and it’s role. Many online brands and retailers –  Warby Parker, Modcloth, Birch Box, Rent the Runway, Bonobos – have found success in opening pop-ups and guideshops as an extension of the brand’s experience.  There’s a lot of interesting experimentation going on with both online and offline marketing tactics and it seemed like the brick and mortar ventures serve different purposes for many of the brands.  I think it will be interesting to see if there is convergence around the purpose or purposes of stores over time – as brand building, customer service, customer acquisition, or for good old-fashioned transactions.

For more Shoptalk coverage, check out here, here, and here.

Forbes Women’s Summit: Female Entrepreneurship in the Digital Age

I recently attended the Forbes Women’s Summit with about 300 incredible founders and leaders.  There were many inspiring business and community leaders, including one of my favorites, Ashley Graham, who spoke about the origins of her modeling career, her experiences as a plus size model, and her experiences building her business.  Confident, proud, and energetic, she was an incredible speaker and an inspiration for all women!

At the summit, I had a chance to be part of a panel including Sonja Perkins, Sukhinder Singh Cassidy, and moderated by Dina Habib Powell. We discussed the challenges and opportunities that female entrepreneurs face in launching and building businesses and I’m excited to share a bit of what we covered.

Landscape of Female Entrepreneurship.

The whole panel agreed that the current state of women in leadership is not where it should be.  There are too few women founders, too few women venture capitalists, and too few women in leadership roles. According to a Fortune study, despite the fact that just 5% of Fortune 1000 CEOs are women, these female-led companies generate a disproportionate 7% of total revenue.  Even in retail, only 6% of top 100 companies are led by women.

Despite the current landscape, we were all optimistic about the future.  We have all experienced improvement in recent years and are hopeful that the success that women are having running companies today, will lead (at least eventually) to a better representation of women.

In the bucket of optimism, I was proud to cite Stitch Fix as a counterexample to the status quo, as 50% of our board is made up of women and over 60% of our leaders are female.  Sukhinder also shared some data about leadership at Joyus, where women represent the majority of leadership roles.

(Forbes/Photo by Jonathan Kozowyk)


Fundraising was another hot topic for the panel.  A few years ago when I was fundraising for Stitch Fix, as a female entrepreneur with a business that was focused on a demographic of mostly women, I found myself pitching to a highly homogeneous, mostly male population of investors who don’t naturally gravitate toward the industry and the value proposition.  I found it difficult to find investors who were excited to be invested in the vision and mission of the company and connected to the product.

Though it’s only a few years later, I do think that there are more women investors today and more success stories on the fundraising front.  I eventually was lucky enough to have found great investors who happen to be male but also excited about and connected with the vision of the business.  My co-panelists are additional examples of success stories with Sonja having funded many women in her portfolio and Sukhinder as female founder and investor.


Although there are numerous studies showing a positive correlation between women on corporate boards and the overall performance, there are too few women on boards. The Anita Borg Institute found only 19% of Fortune 500 companies have a woman on the board. The same study shows that companies that have at least three women directors, have a higher return on sales of at least 42%.

My own experience is that many are motivated to bring on more women – I’ve been asked by several male CEO friends for recommendations for women as they’d like to add women to their boards.  Sukhinder found herself often fielding similar requests, and saw an opportunity. Last year, she launched Boardlist, a curated marketplace to connect highly-endorsed women with public and private companies looking to fill board seats. I was recently elected to the board of GrubHub (NYSE: GRUB) and have found board service has been an incredibly engaging and rewarding experience.  I hope that the Boardlist can help in opening up this opportunity for many others. So, check out the boardlist and start nominating!

There was some great coverage of the panel links which you can find here and here and some great Tweets about the panel below.

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Shaping the Next 25: Dynamic Women in Business Conference

A couple of weeks ago, I returned to Harvard Business School to give a keynote at the Dynamic Women in Business Conference hosted by the Women’s Student Association.  The theme of my presentation was celebrating possibility, and through that I shared some personal stories, the story of founding Stitch Fix, some realities of women in leadership, and what we can do to change it. Below are a few highlights…

Seeing the world through a lens of possibility

I started out with some stories about my family.  I’ve been incredibly lucky to be surrounded by strong, driven women – in legends and in real life – that gave me a lens to view the world with boundary-less possibility.  I was really proud to share the stories of my grandmother and my great-grandmother doing the impossible and overcoming adversity; they have both had a big impact on who I am, how I think about the world, and what I have perceived and believed to be possible.

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Women in leadership

This could be an entire blog post, or an entire presentation.  But in short, while American executives perceive that 23 percent of our businesses are led by women, the reality is not quite as optimistic.  Only 4.6% of Fortune 500 companies are led by a woman, and only 6% of the top 100 retailers have women CEOs.  This must change.  I am particularly appalled that in retail – an industry in which many women enter the industry, an industry which largely markets to and sells to women – that we should see so few women get to the top, or even into the C-suites (only 12% of the C-suites of retail companies are occupied by women.)

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In this crazy world of retail where women in leadership positions are far and few between, I am immensely proud of the inclusive culture we have created at Stitch Fix and the role of women in leadership at Stitch Fix, where women comprise….

  • 50 percent of our Board of Directors
  • 62 percent of our Management team
  • 55 percent of our Director level and above

A few lessons

Lastly, I wanted to share some ideas and experiences that I have had to help contribute to change and progress for the role of women in leadership.  

  • Invest in women. A very difficult reality of today is that 94% of VCs are men.  The people who are investing in the CEOs creating companies, our future workplaces, and cultures are incredibly homogeneous.  As a female CEO that raised money for a company that primarily serves an audience of women, I experienced this challenge first-hand.  In the end, our story is a positive one in that I’m very lucky to have two (male) investors who have been great partners and advocates of me and the business, but it was an uphill battle and I feel passionately that there need to be more women investors.  Even if you’re not an investor in a the traditional sense of capital, all of us can invest time, expertise, and advice.  I’d love to see greater investment in women, the businesses we start, and the cultures we create.  
  • Find and be good mentors. I was very lucky to have Sukhinder Singh Cassidy as a mentor, advisor, and advocate for me.  She had a big impact on who I became as a leader, and on the opportunities available to me and to Stitch Fix, simply by her believing in me and the company.  Find good mentors to help develop and grow, and be a good mentor to pay it forward.
  • Focus on clear objectives and outcomes.  Setting clear, objective expectations around roles and success is incredibly important in cultivating a culture free from bias.  From making sure that your culture isn’t rewarding ‘facetime’ over quality of work, to using a market-based pay approach to limit the introduction of gender or race-based bias – objectivity can help level the playing field.
  • Show and celebrate possibility. Lastly, the thing that every single one of us can do is to celebrate and propagate the stories of success, the stories of women doing the impossible, the examples of women doing incredible things.  Just seeing that it is possible alone makes a huge change in the psychology of children, in students, in any person aspiring and dreaming, and the more we can share and amplify these stories, the more we contribute to opening and expanding the world of possibility.

Finally, I want to thank Harvard Business School and the Women’s Student Association for being such a welcoming and engaged crowd. I loved all of your questions, comments, and Tweets!

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Check out here for more information on the conference and here for details on Women’s Student Association.

Dreamforce Women’s Leadership Panel


Last Thursday, I spoke at Dreamforce 2015 to a large 9am crowd (good job with the coffee, Dreamforce!) during their Women’s Leadership Summit. I was on a panel with Leah Busque, CEO & Founder of TaskRabbit, and Jane Hynes, SVP Communications at Salesforce, and a great turnout of both men and women interested in workplace equality. The full video can be found here, but I’ve included some highlights below.

On VCs, Fundraising, and Gender…

I could write an entire blog post on this topic, but the short version is that today 94% of VCs are men.  Even setting potential gender bias aside, I found it incredibly difficult to pitch an industry, business, and end customer to a predominantly male community — it was difficult to relate to. Despite a high amount of interest in our business and our financials, the reality of talking about dresses in a board meeting and imagining how he might add value in a board room setting to our women-oriented, fashion-based business, made it hard to find a match with investors. There is an ongoing need for more diversity in the investor base in order to drive diversity in the leaders and companies that get funded.

Need to see it to believe it…

I firmly believe in the value of Jane, Leah, and I bring by simply being who we are in plain sight.  A significant reason for a lack of gender or racial diversity in leadership and entrepreneurship can be traced to a lack of role models, mentors, and examples. Leah shared a great moment of defying expectations of what a typical leaders looks like:   

“When [Rob Hayes of First Round Capital] invested, we had never met in person, everything had been done over the phone because he was in New York and I was traveling and it was just difficult to meet… so we closed the round and we had a board meeting the next week. He shows up to the board meeting and I walk into the room and he says “*gasp* Oh my goodness, I didn’t realize you were so tiny! And he was totally taken aback by me because so many times, people look at me and I’m a little bit on the petite side… and they don’t expect me to come in guns blazing… that is sort of a contrast that people have to reconcile sometimes.”

I had a related experience on a recent trip to our Dallas distribution center,  where a young woman came up to me and she said “I just can’t believe it: you’re tiny like me, you’re young like me.” I could see in her face that she was having a moment of realization, re-thinking her idea of “what a CEO looks like,” as proceeded with me the entrepreneurial ideas he’d like to someday pursue.  Even feeling like I had a small part in expanding the world of possibility for her and for others adds meaning to what I do.  

For the whole event, check out here and here!


Last weekend I cosigned a letter with over a hundred other women to choose possibility. The full project, which was authored by our earliest investor Sukhinder Singh Cassidy, and list of female founders can be found here and here.

Quantifying the challenges of and solutions for gender bias are a big part of why this project important to me. However, the most important reason is that the preservation of the mindset of possibility is not just about women.

Sukhinder put it best, that “as a startup community, our most universal bias is toward possibility,” and we should all fight to preserve that mindset as the DNA of Silicon Valley and the DNA of the American Dream.

Before it was Uber, it was a regulatory nightmare. Before it was Stitch Fix, it was an inventory nightmare. Before it was Pandora, it was an unscalable human music genome project.

92% of start-ups will fail. Starting a company is not about what is likely, or even what is probable, it is about chasing visions that are, in some world, in some place, remotely possible.

All of us face challenges in starting businesses—gender, race, socioeconomic status, can be prominent among them. I hope that through this project, that we can openly and productively acknowledge all of these challenges and work toward solutions and improvements.

Even greater, I hope that this project can serve as a reminder of what is possible despite and often in spite of these challenges. We still have a long way to go for a more equal playing ground, but the more we help the world to see in possibility-colored glasses, the faster we can get there.

SXSW 2015 Recap

I can’t believe SXSW has already come and gone this year, what a blur. It was a fun few days– the panel I was on with with Julie Bornstein (former CMO of Sephora and just recently announced as our new COO) as the moderator and Jennifer Hyman, founder and CEO of Rent the Runway, was an incredibly fun and engaging dialogue, I hope the audience enjoyed it as much as I did.

The conversation streamed from personalized omnichannel retail to the importance of data to facilitating the development of female entrepreneurs and leaders. Rather than put it in my words, I pulled some of my favorite tweets …

One of the spicier moments of the panel was when Jenn from Rent the Runway spoke to the challenges of shipping costs and rallying around putting UPS and FedEx out of business. More here.

Speaking of data, Bill Gurley’s conversation with Malcolm Gladwell was a major highlight of the week. Check it out here. Selfishly, one of my favorite quotes of Bill’s was that “The best companies have a data scientist who reports directly to the CEO.” Jenn and I both have that one covered.

We concluded our session with a bit of a digression from retail to talk about women and gender bias. We weren’t the only session to touch upon this topic, it was a major theme that echoed throughout SXSW this year. Despite some awkward moments, I do feel optimistic that the conversation has started to move from establishing facts about the uphill battle facing women to finding and exploring real solutions and actions. Specifically, mentoring and championing women, having women in leadership roles and in board seats, and asking for explanations when they aren’t. It’s worthy of a stand-alone future blog post, but I felt there was energy from men and women for change.

How we Hired “One of the Most Powerful Women in Beauty”

Last week, we announced that Julie Bornstein, former CMO and Chief Digital Officer of Sephora will be joining our team. You can read more about it here on re/code or Racked here. It’s a huge, very important hire, and it was really fun to receive all kinds of congratulatory messages, texts, tweets, and emails. The most frequently used word was “wow,” but the most frequently asked question was “How did you land Julie?”
So, I wanted to share some anecdotes on my path with Julie, and some more general advice and learnings from hiring our amazing team of executives.

1 – Boundaryless pursuit: Identify and target the very best dream team of talent, and don’t feel constrained by what does or doesn’t feel achievable or likely today. Simply getting the best people aware of what you’re doing and excited about your business is an achievable short term goal that can creative significant long term value and opportunity. I was first introduced to Julie in April 2012. I encouraged her to get a Stitch Fix, and met with her again in July to share some milestones with her and get her feedback. A couple of months and a few more meetings / feedback sessions later, we were lucky to welcome her on our board.

2 – The power of ‘Not Yet’: There is a great TED talk on this topic but being able to take what might be a ‘no’ and turning it into a ‘not yet’ can transform the way that you think about relationships you build over time, whether with potential candidates, board members, or even investors. Feeling like you are on a path from ‘Not Yet’ to a potential, maybe someday ‘Yes’ is a more more productive and fulfilling pathway than being on the dead-end street that is ‘No.’

3 – Owning and sharing a journey together: The most rewarding experiences people have involve development and growth. Whether it’s raising children, developing people into leaders, or creating a company from a seedling of an idea — it’s incredibly rewarding to be part of a transformation. Over the several years that we had a chance to work with Julie, we were lucky recipients of ideas and advice that we could immediately try, test, and put to work to make the business better. I also believe that this had the indirect impact of making the experience rewarding and inspiring for Julie.

4 – Create substantial and impactful roles: Amazing, highly capable people are drawn to roles that are impactful and meaningful. Trust the team you’re building. Be generous with opportunities. Embrace hiring people more experienced, more capable, and smarter than you. Create an environment in which your team challenges each other and most importantly, learns from each other.

Last but not least, remember that it is a journey. It was important to feel confident and optimistic about the path we were on, even when I couldn’t have known that it would ultimately lead here, lucky enough to welcome Julie to our team!

How To Evaluate What You’re Really Getting Paid At That New Job

I had two early job experiences that appeared similar on the surface, but were massively different in how much they added to my life and my future capabilities. I was paid comparably in both, but in one role, I was performing similar tasks every day in a tiny office with no peers or mentors. In the other, although I worked more hours than I would have liked, I was constantly stimulated, learning, and surrounded by people I genuinely liked– many of whom I still stay in touch with.

I’ve since realized over time that there are many dimensions to what you truly get out of a job. In reality, whether you’re considering a job at a huge company or a friend’s startup, what you should be trying to maximize is your total long-term earnings potential. Not just the value of what you are earning today, but the total value of the tangible benefits and non-tangible experiences earned during your 40- or 50-year working life.

So when you are considering a job opportunity, here is a more comprehensive list of things that I think you should be considering before signing that offer letter.

Why Stitch Fix Calls San Francisco Home

San Francisco is one of the most expensive cities in the US, and one of the most competitive places to hire great talent. It’s also quite far from the fashion and media communities in New York, and not exactly the center of the US from a population perspective, making it expensive to ship Fixes from here! Did it really make business sense for Stitch Fix to call San Francisco home?

We had the opportunity to host Mayor Ed Lee in our offices recently and it gave me a chance to reflect on how we’ve benefited from being located in San Francisco and what the business case was for us to pay the high price of doing business in this beautiful city.

People– First and foremost, the high concentration of incredible people here in the Bay Area makes it almost impossible to imagine building the company anywhere else. Here at Stitch Fix, we need to have incredible merchants working alongside talented data scientists. There are so few people who have run operations as large as as Mike Smith has, or people who have run all of data and analytics at a place like Netflix as Eric Colson has; the access to incredible talent here in the Bay Area is simply unparalleled.

Innovation – There’s a culture of the city and startup scene that is also reflected in the people here– innovative, fun, ambitious, and respectful of diversity. Approaching things differently and unconventionally is a core value of our company; the culture of innovation and openness to try new things is something we benefit greatly from.

Community – Mayor Lee talked about the community of sharing — both knowledge as well as resources — in San Francisco, which applies to many industries including transportation, lab research and hospitality. We’ve been lucky to benefit from countless other start-ups in the community who have shared, given, and supported us. DropCam (who recently got acquired by Nest, congrats!) was our first landlord and not only did their CEO give me the gift of great advice for the business and building our own culture, but also gave us their furniture when they moved to a bigger and better office. Many other CEOs and founders shared their time and advice with me in the early days, but in particular Jim Cook (one of the founders of NetFlix) and Joe Kennedy (former CEO of Pandora) stand out for generously spending time with me and offering guidance that has stuck with me.

To be very honest, it wasn’t any of the three reasons above that was the primary reason for locating Stitch Fix here– I spent most of my childhood in San Francisco and being able to call this city home made it feel easier, more comfortable, and more permanent to set up here. Looking back, it has felt like it would have been a lot harder to make Stitch Fix work if we hadn’t been here and been able to take advantage of so much that San Francisco uniquely has to offer. Each company has it’s own key challenges that help inform what is most important for it’s growth and development; for us, access to and ability to recruit amazing caliber talent from a few diverse industries has made all of the difference.