Retaining Women: A Problem Startups Don’t Have

By Lucy Drummond 

Two early twenty-somethings catch my eye as they step out of the elevator in suits. This is an unusual sight at WeWork, where most employees dress in business casual. Comfortable wear is especially important during New York City’s humid, sweltering summer months.

The two young gentlemen sit down with wide eyes. I can tell they are in disbelief at what is going on behind me–sangria is flowing, beer is on tap, and a company is giving away free t-shirts. Relaxed lounge music plays in the background. It is 5:45pm on a Wednesday.

Park South

WeWork Park South, courtesy WeWork

I smile and turn to read the Bain & Company report I have been assigned, entitled “Everyday Moments of Truth: Frontline managers are key to women’s career aspirations.” My smile fades. The subject is women’s career aspiration in corporate America–or how it gets sucked out of them due to uninspiring management at mid-levels.

The irony is great as I simultaneously read this report and listen in on the young suits in their conversation. They have been joined by a third, a man who works at WeWork, but he wears a collared shirt and jeans. He has to persuade the younger two that the drinks and snacks are not some sort of trick, and now with beers in hand, the younger two relax.

The man who works at a startup within WeWork is a former private equity banker, and is a few years older than the other two. He tells them about the freedom and flexibility of his current career situation: the hours, dress code, amenities, events, autonomy. The two suits listen intently, occasionally chiming in with statements such as: “Yeah! I hate leaving work at 9pm, leaving at 6 sounds awesome!” I suspect their current absence from work is quite an anomaly.

The palpable excitement of the two young corporate men provides an interesting backdrop to the material I read.

Women graduate college with confidence and “wind in their sails” because academia has made significant strides in gender parity. At college, female students are encouraged to raise their hands, participate, form groups, and develop as public speakers. For their first two years of corporate experience, females carry this character strength with them–43% aspire to rise to senior level management and C-suite positions. This is more than their male counterparts: only 34% of males in entry level positions aspire to rise in the same way.

Unfortunately, this is the only time in corporate careers that women’s aspirations to rise surpasses men’s. Mid-career, the desire to climb the corporate ladder for women shrinks in an inverse relationship with the more experience they get. Some of this aspiration is regained at the highest levels of management, but it neither recovers fully nor again outpaces men’s.


By the time women are considered “experienced” employees–over two years of working on the job–their aspirations to reach the top level of management have split in half. Only 16% of female employees at this stage want to rise in their corporations, compared to 34% of males. At more senior levels, this number improves, but it never fully recovers. 34% of mid to upper level female employees desire to rise. However, more than half of men at the same level (56%) want to continue to rise. This last set of numbers may even be skewed as some of the women who lost aspiration have probably left.

Bain’s reason for this drop? Being human.

Employees today–especially millennials–want to feel engaged and inspired in their work, and are more productive when these elements are present. The more an employee feels understood and supported, the more committed she or he becomes. Especially for women, so says Bain, relationships and communication are central.

It makes sense: corporations measure success using qualitative terms. Women have been barred from many powerful positions because of exactly that; they have been considered to be “too emotional” for rational, calculated, professional decisions. However, that sort of biased thinking is long out of fashion, and has been debunked by research that proves having more women in executive decision-making positions increases the bottom line. The neglect of the qualitative actually hurts profit.

Female employees are as competent and committed as males, but on the whole they need more human and authentic relationships at work.

What will help women keep their aspirations is for mid-level managers to develop more open, interpersonal relationships with junior female employees. Two thirds of senior male employees are hesitant to have a private meeting with a more junior woman, which I imagine comes out of a respectable intention. However, the effects are detrimental because it stymies honest conversation and the possibility of a mentor relationship.

To fix this problem, Bain suggests managers share their personal stories about balancing work and family life in the conference room. Yes, you read that right, the conference room. One of the top management consulting firms says that opening up about family and personal life in typically professional-only settings will increase commitment and help retain female employees.

The surprising–albeit very welcome–suggestions do not stop there. Bain says: “Visibly reward and outwardly champion employees who break the mold, offering public recognition for those who are successful using non-traditional schedules or career paths.”

Another suggestion is–of course–having more women serve as role models in higher level management. But this is a chicken and egg problem, and will be ameliorated as the the pipeline for mid-level professional women improves.

I can’t help but feel that startups already do a lot of what Bain calls for. Granted, it comes with the territory; being small and new offers an inherent opportunity to do what big, established companies cannot. But I still wonder why so many women would choose to stay in uninspiring career paths, hoping that their superiors will change.

As I finish reading the report, I glance up. The three gentlemen are still talking, swapping stories and laughing in camaraderie. As I gather my things to go, I wonder how long it will be until I see the two younger men in t-shirts happily strolling the halls of WeWork.

Ecosystem Header

The Ecosystem for Female Entrepreneurs

There are many graphics that show the power of the male networks that supports male founders. There have been articles about the powerful and exclusive boys club. Men connect by doing business, sharing deal leads, playing sports, providing funding, and passing the hat around the table to support their buddies. It is human nature to hang with people you know and like and are similar to you. You feel comfortable and you don’t have your sense of self or ideas challenged by anyone. All of this is understandable even when it has adverse consequences.

Women of all ages are looking for ways to advance and champion each other. There are some established groups that were trailblazers as well as many new organizations springing up with purpose and commitment to open access and funding opportunity. We need all of this and more.

We have identified the organizations that have a primary and demonstrated commitment in one or more of these areas: women entrepreneurs; women building tech; women angel investors and women professional venture investors.

All of the companies and organizations in our graphic spend their time and money in the pursuit of equal access and opportunity for women and outstanding companies. This is a new age of action oriented initiatives where you use your influence and money to change things around. We did our best to include the companies we know but there are probably more to include. If you know of any additions please contact us at Keep in mind that they have to service one or more of the 3 categories above and this has to be their primary focus. Thank you.

Deborah Jackson

Ecosystem Raising Capital

Ecosystem Support Women

Sources of Economic Hope

Rising To The Challenge

The Motivations of Female Entrepreneurs

The third infographic of our series based on data from the Kauffman Foundation’s report Sources of Economic Hope: Women’s Entrepreneurship explains why entrepreneurs don’t quit.

The hurdles are many when launching a business or venture. What keeps entrepreneurs going is the creative potential in pursuing their wildest dreams. The most common reason for starting a business is the founder’s desire to capitalize on an idea.

Entrepreneurs identify factors that have contributed to their success to varying degrees. However, the most important factors consistently involve learning from the past.

Lessons learned from previous success is tied with prior industry work experience as the most common success factor in startups.

What is notable is that learning from past mistakes is a very close third. 88.2% of respondents state that learning from wins is important, while 87.3% agree that learning from failures is also so.

Those who are truly motivated will turn “failure” into an advantage–seeing it as more of a growth map than a defeat. Founding a company requires immense determination. Those who are successful turn setbacks into opportunities to refine their goal.

The last part of our infographic explores how failure is experienced by women and men. Short summary: women value hard work whereas men trumpet self-confidence.

Sources of Economic Hope

Graced by Grit

The Story Behind Graced By Grit

Interview by Sophie Pape

Kimberly Caccavo and Kate Nowlan laugh in tandem about the night before they opened their first store for their new women’s activewear – Graced by Grit. “We were up very late the night before sewing curtains! Our staff called to check up on us, realized we were still there, and came to help,” says Caccavo. “That is what we look for in our employees: hard work. We have women from all walks of life but hard work, they all have in common,” adds Nowlan.


It is apparent that the duo have learned to inject a sense of humor into their venture. Indeed, Caccavo says that whilst they are both giggling, realistically, they are most likely delirious with stress. “When our staff arrived to help, we were both sitting on the floor sewing and laughing,” says Caccavo, “being able to laugh is so important.” Especially since this store opening was not planned.

They had unexpectedly been backed by a bank who believed in them and they opened on the fly. “Being nimble and being able to make decisions quickly is very important as an entrepreneur,” says Caccavo. And so, when the opportunity arose, they thought it would be a good move and thank heavens, thus far, it has proved to be just that.

Their journey started when Nowlan was teaching Caccavo’s young son to swim. Caccavo asked Nowlan if she knew of anyone who may be able to train her for a triathlon and since Nowlan was something of an accomplished athlete, she turned out to be just the person. “I didn’t realize that Kimberly [Caccavo] had just three weeks to train – so we became friends quickly,” says Nowlan.

Store openingCaccavo’s son cuts the ribbon for the first Graced by Grit store

“I remember losing time on my transitions that she [Nowlan] had taught me the night before; I’d forgotten them,” adds Caccavo. Of course this may have been consequent upon the fact that she was prepping for the race like any normal woman, i.e. with a glass of red wine. (Incidentally, she finished very well that day – in the top third of her age group.)

The friends bonded over their love of the outdoors, both had been keen sportswomen in their youth and that love of activity had sustained itself through their eventual move to California – Solona Beach – just north of San Diego.

One day, they were out running; unsatisfied with the activewear they wore and that of their fellow female runners. Ask any woman, the correlation between feeling confident and performing well in full view of other “athletes” is strong. The better you feel you look, the more confident you are, the further you will run, the higher you will climb and the faster you will peddle.


“Women would try on our products and they would look better which made them feel better, and made them perform better,” says Caccavo, “Kate [Nowlan] needed a really advanced and accomplished fabric that would aid her performance and I needed a fabric that would hide my lumps and bumps. We both needed a fabric that would survive sea and land – and we developed just that – in colours and styles that suit every woman.”

Caccavo and Nowlan’s young business is doing well so far. Their customers range from eleven year old gymnasts to a lady of 87 who rides her mountain bike (without a helmet) every morning – and who is said to be one of their biggest champions. But it is their commitment to the business that is truly compelling.

“We wake up at 5.15am every morning so that we have a couple of really productive hours. We are really efficient, we make decisions really quickly and if they happen to be the wrong decision, we figure it out or renegotiate immediately,” says Nowlan. Chiming in, Caccavo says, “We try to do the right thing. Often you do the right thing if you make an instinctive decision. If Kate and I decide we are going to do something – and it’s wrong, we change course and we don’t dwell.”

Their final nugget of entrepreneurial advice came from Caccavo’s husband, “Don’t fool around and make it happen.” They laugh. “We were going to use ‘Just Do It’… but someone beat us to it.” Making it happen… is exactly what they intend to do.

Obstacle Course

Hard But Worth It

The Challenges of Being A Female Entrepreneur

Our second infographic in this series based on data from the Kauffman Foundation’s report Sources of Economic Hope: Women’s Entrepreneurship illustrates the hurdles of launching a venture.

Not surprisingly, having enough time and money is seen as the biggest challenge in starting a business. Next up is acquiring capital: 72.1% of people feel that finding funds is challenging. What’s even worse is that acquiring early stage funding such as venture capital is harder for women than men.

Men are more confident than women in asking for money from their networks of close friends and business acquaintances. Women need to step up that part of their game. But also, money flows more easily to men. Male founders are 3x more likely as female founders to access equity financing through angels or VCs. A funding gap turns into a growth gap and then an outcome gap.

Apparently, the least challenging aspect of starting a business is lack of industry knowledge. Only 6% (the lowest number) of respondents feel that this is extremely challenging.



Internet Week Recap

By Lucy Drummond

I attended Internet Week New York (IWNY) to better understand how our wired connectivity is affecting businesses and other fields. What I found is quite promising.

Once a year for IWNY, technology and internet luminaries descend upon New York to take part in a flurry of panels, events, and showcases. The goal is to celebrate and reflect on entrepreneurism, innovation, and the impact of technology. Of course, plenty of similar conferences and events take place throughout the year. But Internet Week–now in its seventh year–is unique in its quality and breadth.

The major victory I witnessed at IWNY 2015 has to do with its active spotlight of women. I have never seen so many prominent women recognized and given the stage at a major conference unless the conference’s theme is specifically devoted to women. Both men and women are doing creative, promising things with the internet, and IWNY successfully brought light to many of them.

In attendance at IWNY 2015 were Plum Alley favorites Jenn Shaw and Molly Hayward. These two ladies completed successful campaigns when PA’s crowdfunding services first started.

Zuckerberg, Brown, Lapin, Hayward

Hayward spoke on the panel “Taking Taboo Topics Social” with news anchor and Rich Bitch author Nicole Lapin, and lawyer cum media mogul Binta Niambi Brown. Moderated by Randi Zuckerberg of Zuckerberg Media. The panel tackled such issues as menstruation, money, and sex with humor and grace.

This was one of my favorite panels of the week.

A highlight of this year’s IWNY was Chelsea Clinton, who spoke with data visualization expert Ben Fry on their recently released No Ceilings: Full Participation Project. Clinton’s goal with the project was to make a mass of data points living and breathing through human stories.

Clinton’s humility allows her work to shine through. I was struck by her poise and eloquence.

Chelsea Clinton

No Ceilings celebrates achievements such as the increase of women who participate in the workforce around the world. The report also points to where more work needs to be done. For example, women have less access to the internet than men.

Fry has requested that developers who believe they can improve the report contribute to it on GitHub. No Ceilings is truly a 21st century report.

The co-founders of Wired, Jane Metcalfe and Louis Rosetto, spoke with Webby Media Group President David-Michel Davies. The two Wired visionaries were prioritizing web-based content in the early 1990’s when most people still didn’t know what the internet was. Metcalfe and Rosetto’s cool demeanor betrayed the secrets to their success: confidence is key.


Rosetto, Metcalfe, Davies

Another highlight of the week was its opener: Abbi Jacobson and Ilana Glazer, the genius writers and stars of Comedy Central’s Broad City.

Broad City

Jacobson, Glazer

Jacobson and Glazer owe their ascent partly to the internet. With humble beginnings at the comedy training ground Upright Citizens Brigade, they achieved viral success from their friends after filming their first “webisode.”

Their career pasts influenced their internet mastery: Jacobson did SEO and video uploading for TED, and Glazer managed social media for a skincare brand. These young ladies prove how fluency in media can propel creative projects forward.

I greatly appreciated their response to an audience member’s question about the common comparisons between their show and HBO’s Girls. They began their response by saying that it’s wonderful to be considered alongside such a successful show. But they also pushed audience members to think about the assumptions in the comparison; why must one show be favored over or measured against the other? Why can’t both shows, that center around the lives of young women, be celebrated and liked?

Overall, IWNY 2015 was a success. It provided a space to listen to others, think critically about tech and internet developments, and connect on the ways that the internet has changed lives.


Crowdfunding Success: Karla Lemmon

Karla Lemmon raised $7,765 on Plum Alley to develop an app for parents to pack, plan, and connect with their children while they’re away. Below, Lemmon reflects on the crowdfunding process.

Were there any unforeseen challenges or easy spots that you encountered while raising money?

Right before I started the campaign, I decided to leave my corporate job to pursue entrepreneurship full time.  I shared the campaign site with many of my former co-workers as an introduction to my new venture without actually asking for financial support.  I was overwhelmed and humbled by the amount of support I received from this simple act.

What did it feel like when you realized you’d hit your goal?

I felt both excitement and relief knowing that all of the hard work had been worth it.

What role did social media play in your campaign?

I used Facebook, LinkedIn, and especially Twitter consistently throughout the campaign.  I’m not sure that I can directly correlate funds to the use of social media, but what it did do was get me exposure and a following that I wouldn’t necessarily have gotten so quickly.  Between my friends’ social sharing and my own, a much larger audience became aware of Little Peanut on the Go.

Were you glad to have raised 30% before going live? Did it help?

Raising 30% before going live gave early momentum to donations.  It also indicated confidence in the concept and in me.

What’s next?

I have started marketing efforts for Little Peanut on the Go and am deciding whether to move ahead with a similar smartphone app for pets.

Thank you everyone for your support, I am extremely grateful!