Dollars & Sense

Creative Collaboration: Women-Led Start-Ups Standing Stronger Together

THE JILLS OF ALL TRADES™ is a powerhouse talent collective of Freelancers, Consultants & Entrepreneurs. Our platform AGGREGATES solo professionals, who are often fragmented and hard to find, to gain bolder & bigger marketing exposure. We CENTRALIZE relevant resources, tips, & tools to make it easier & faster for solos to run their businesses. By creating a community of gig economy peers, we SOCIALIZE an all too isolating work style

What Women-Led Start Ups Do That Every Business Could Learn From is Creative Collaboration.

What we hear about women-led start up ventures, far too often, are the dismal funding statistics - female founders got roughly 2% of venture capital in 2017.

What we don’t hear enough about is this - Despite these staggering funding gaps, or perhaps in spite of them, women led ventures continue to outperform their male counterparts in just about every metric.

Female owned firms generate higher revenues than their male counterparts and they create more jobs. Women executives significantly improve start-up company performance. Women are known to be more effective in senior leadership roles. Women have a higher appetite for growth.

Living in a such a dismal funding landscape women entrepreneurs have had to become fiercely savvy in creating and building businesses. Women have long understood that access to cash is a struggle, so those embarking on start-up journeys know from the get go that they have to build a healthy and sustainable foundation for their businesses if they are to survive. They have to be hungrier, smarter, streamlined, efficient, and practical.

After endless years of institutional bias, it’s generationally ingrained in women to do so.

Now this is not to suggest that the institution bias against women in entrepreneurship, or in any other financial or social realm, has in any way benefitted women. Let’s be clear.  It has not. But it does seem, at a minimum, it’s about time we acknowledge, take note, and learn from these female founders.

And what they are doing with deft and acuity is collaborating.

You don’t need to look too far to see how women entrepreneurs are building, shaping and creating spaces and frameworks for community and collaboration. Women supporting women is the strength of women’s entrepreneurship and crux of keeping their operations lean and successful.

THE JILLS OF ALL TRADES™ is a powerhouse talent collective of Freelancers, Consultants & Entrepreneurs. Our platform AGGREGATES solo professionals, who are often fragmented and hard to find, to gain bolder & bigger marketing exposure. We CENTRALIZE relevant resources, tips, & tools to make it easier & faster for solos to run their businesses. By creating a community of gig economy peers, we SOCIALIZE an all too isolating work style

Take for example, the explosion of women’s co-working. Seattle-based The Riveter offers coworking ‘built for women’ and now has multiple locations in Seattle and in LA with plans to open in 6 other cities across the nation including Austin, Atlanta, Portland, Dallas, Denver, and Minneapolis. Similarly expanding, New York based The Wing provides a social club for women, including coworking, and states its mission as the advancement of women through community.  

Online communities like THE JILLS OF ALL TRADES™  are focusing on the growing freelance economy and aggregating a too often fragmented group of women freelancers and consultants, into an online collective of independent professionals. THE JILLS, as their members are dubbed, provide diverse services to businesses of every scale from solos and start-ups to small businesses and corporate giants.  They aim to create a ‘sisterhood for solos’ and tout the merits for women to work as independents and reinforce that this should not equate to working alone.

The newly founded, Madison based, DirectorHERy seeks to connect women-owned businesses with consumers who want to see them prosper through their online directory. And SheEO is tackling the female funding gap, by mobilizing women to build communities to support and fund women entrepreneurs through their model of ‘radical generosity’.

Women want to see women succeed. They know there are droves of amazingly talented women, like themselves, who are eager to work and create, having found very little of what they need or want in traditional workplace settings. They’re their friends, and neighbors, they meet at the gym, at playgroups and book clubs and more recently they’re finding each other through women based co-working spaces and digital community-based platforms.

They are building each other up and encouraging and designing a future of work that works for women. They know the critical importance of developing collaborative, reciprocal relationships within their communities to build their knowledge, their skills, and their teams. They are using collaboration to build businesses and build wealth. They are modeling and leading a new economy - the future of work.

For women led ventures, collaboration is winning over competition and building a strong ecosystem for women entrepreneurs to continue to grow and thrive.

If any of us is to find our path in the new economy, it’s about time we start to look at the women who are leading the way for us, and figure out how we might catch up.

TECH + THE Pay Gap Paradigm Shift

Something big is going down.  You can see the cracks and feel the reverberations. Change is in the air, as women use, make, create, and build technologies to power a pay gap paradigm shift.

Yep you heard it correctly. Women are harnessing technology to power their paychecks. 

Technology fashions shift sin Wage gap. -THE JILLS

Now, the stats are still lousy when it comes to pay equity.  According to the AAUW report, The Simple Truth About the Gender Pay Gap, "in 2015, women working full time in the United States typically were paid just 80 percent of what men were paid." The reports also suggest that progress toward pay parity is slow and that it has stalled in recent years suggesting equity may not be achieved until the year 2159!  The report also identifies larger gaps in pay for women of color and notes that as a women ages the pay gap grows. 


However, in her article for the Harvard Business Review, How Technology Can Help Close the Gender GapSallie Krawcheck, CEO and Co-Founder of Ellevest, offers hope. Krawcheck deftly draws conclusions about how access to information (specifically information on companies' gender practices) , online social networks and communities, and value-driven decision-making are bridging the pay gap and leveling the playing field for professional women. She suggests there is a lot happening that is moving women in the right direction for pay equity. 

Good news for us all.  The timing, it seems is at a critical pace for women to know about, explore, and utilize the infrastructure and the ecosystems that are currently creating a much needed equalization of power in the workplace and beyond. 

Throughout the article, Krawcheck details numerous technology resources that women can access to help close the gender pay gap (which you should totally check out) and she identifies the growing number of options for women in the workforce as making significant impact on the gender pay gaps. She highlights the increasingly viable option of entrepreneurship for women and notes the importance of being able to hire on a project by project basis as a contributor to the success of startups and young companies. Krawcheck also predicts a very near future "in which professional women work for, buy from, and invest in companies that align with their values."  Vicki Saunders' organization SheEO is one that is already creating this future with their approach to investing - Radical Generosity - where up to 1000 women contribute $1,100 to create a million dollar fund to invest in women-led ventures. Nicole Yeary, also exemplifies these ideals with her Chicago-based company, Ms. Tech, whose member platform 'helps business women do tech, and tech women do business'. 

Women empowering women, does indeed seem to be a theme for bridging the pay gap.  

And this is, indeed, why we founded THE JILLS OF ALL TRADES™. Because forming an ecosystem and shaping an infrastructure where women entrepreneurs can help women entrepreneurs lift and link each other, complete projects together, find community and get stuff done... well that has the potential to change everything.

JOIN THE JILLS. FIND A JILL. REFER A JILL. And start to power a cycle that spurs a workforce revolution and help us all work toward bridging the gender pay gap. 


Xero Out

Okay, first things first, if you're using the same bank account for your personal account and your business account - STOP. Get a business account and stop mixing your money. 

Whew. Now that's cleared up, let's talk about a robust and affordable online tool for keeping track of the money in your business account. 


professional Accounting software systems

For less than $10 a month, you can have this amazing online accounting software that will keep you on track with invoicing, and payments, and reconciling your accounts. You can code expenses and track mileage. It'll print reports galore.

And if you're not versed in bookkeeping or accounting, fear not.  The interface is intuitive, and even when you're not even sure what you're supposed to be doing, there are enough tutorials, and online help and chats to get you into the swing of it. 

So give it a whirl. You might find those weekly 'money dates' have a brand new zip to them. 

Ladies, Let's Stop Being So Polite About Money

Financial savvy for women in business

Let's stop being so polite about money. Seriously.

Let's start asking each other where we make money and where we don't; how we save money or why we don't. Let's start telling each other what we don't understand about money and start helping each other take control over our thoughts, emotions, and actions around money. Let's get confident in asking for money and knowing our value. Let's be clear about what we charge for projects, how we manage cash flow gaps, and who's lending to whom. Let's talk about how we access health care, and how we pay for college, or professional development, or awesome software, client coffees, dinner dates, and that dang trip to Cancun. Let's be clear about what we expense, and how we keep track of it. 

Let's make this the year to let go of fears and anxiety around money and exchange it for awareness, transparency, collaboration, and information. 

Because by shying away from the cash chit chat, we're adhering to a code that disempowers us.  

And in order for us to lead a workforce revolution.  We need to be empowered. 

So let's start some money chatter right now.

Here are a few actionable first steps for entrepreneurs of every sort, from side gigs to solos, to startups and small businesses: 

1. Get a separate bank account for your business. This is the first step to getting your business financials in order. Whether you take on a project or two a year or have a full-time operation with employees and contractors, it is never the right decision to mix your personal account with your business account. Keep them separate and pay yourself from your business account into your personal account. Even just one side gig project demands a separate account. 

2. Same goes for credit cards. Don't mix personal and professional. If you cannot yet get a business credit card, then simply dedicate a personal card exclusively to your business. 

3. Understand money in, money out. You need to know exactly what money is coming in and what money is going out. It seems basic, but it is so often unexamined. This cannot be guess work or estimates. Look at it. Understand it. Reconcile it. When you really start to look at your transactions you can begin to truly understand the cost of a project and what you're actually earning. You will be able to make informed decisions about how to best operate your business and allocate your time. The best ways to understand 'money in, money out' is to track it. There are several online accounting software programs (at THE JILLS OF ALL TRADES™ we love Xero) that can help you do this, but so can a self-created spreadsheet, or a big 'ole paper ledger. Whatever your approach start tracking now. 

4. Schedule a money date with yourself every single week. Avoidance around money is all too common. For some of us, the task is arduous. For others, the fear of what we might learn can paralyzes us. At times, it's frustrations about what we have to pay in student loans, or health insurance, or rent that keep us from simply facing our cash. And too often, we are just busy, so we put it off. But the truth is, when you start to look at your money routinely, it indeed becomes routine. It gets easier, less time consuming, and you, as a result, become more informed and more confident. So make a money date every week. Put in on your calendar, and block 15 minutes to check in with bank statements, reconcile your accounts, follow up with invoices, and make payments. Practice will help you feel better as you make financially informed decisions for yourself and your business. 

5. Pay yourself first. If you did the work, then you need to pay yourself for it. How much you choose to pay yourself will depend on what you learned about the true cost of your projects and what you charge for them. And remember there is a cost to running your business and taking care of yourself. Know what you truly earned and pay yourself. 

Spend Money to Make Money

Our JILLS have great things to say and we're so happy to share it! 

Belinda Wasser is the founder of Rocket Girl Solutions and a guest contributor to THE JILLS NEWS. With over 25 years of experience in business workflow and logistics, Belinda offers up practical advice on running your business so it isn't running you. We're proud to have Belinda as one of our JILLS OF ALL TRADES and welcome her expertise in working with solo professionals and small business owners as their part-time business managers. Belinda loves taking care of the daily details and minutiae so business owners can get back to the work they love doing!  Our JILLS have great things to say and we're so happy to share it in THE JILLS NEWS. 

Our JILLS offer up some of our best tips and in this post, Belinda reminds us that we need to rely on the skills and talents of others to truly build our businesses. 

Belinda Wasser, founder of Rocket Girl Solutions

Belinda Wasser, founder of Rocket Girl Solutions

Authored by Belinda Wasser

I was in Rosie’s on Elm Street last Thursday, enjoying a few quiet minutes at the end of the day with my friend Jennifer. We were talking about the usual things – business, kids, weather and more business.

And then she said, “It seems like you have no problem spending money to make money.”

I don’t, but I was definitely surprised to hear her say that. To me, this isn’t just a good approach; it’s the only approach that really works if you want to grow your business.

Here are some of the things I had mentioned during our conversation which prompted her to say what she said:

Debbie Faye is working with me on improving my speaking presentation.”

“I hired a business coach, Jane Pollak, to help me reach my goals for the year.”

“I’m working with Scarlett DeBease to update my wardrobe.”

“I’m interviewing new accountants to help me organize my business.”

Later, as I was driving home, I realized how happy I am about what has now become my standard approach: Paying wonderful, capable people to help me work better, faster and smarter.

In other words, instead of doing everything myself (the way I did for years), I surround myself with experts. That’s real leverage.

Unfortunately, lots of solo professionals don’t see the world this way. To them, spending money (especially if things are feeling financially tight) feels like an extravagance. What I’ve found, though, is that you have to spend it to make it!

When is it time to get help?

In almost all cases, the answer is: Sooner than you think! In my experience, people wait way too long to bring in support, often putting it off until things have gotten really bad with missed deadlines and worse.

So, here are two questions to get you started:

  1. Are you doing work you’re not really qualified for?

    Tinkering with your website, doing your own taxes, setting up an email newsletter are all business essentials best handled by experts. Maybe you’re good at some of these things, but many people aren’t, resulting in poor quality work that takes a lot of time to complete.

  2. Are you doing work that’s below your pay grade?

    There’s nothing shameful about putting together your own client gifts or running down to Kinkos to make a bunch of copies for tonight’s presentation. But much of this work can be done less expensively by somebody else. If you’re spending time on this, you’re not spending time doing higher value tasks.

Simply put, you can’t build much of a business if you’re not willing to rely on other people. Find others to support the high quality – high paying! – work you do best and pretty soon you’ll also be spending money to make money.


Ahem.  I'll admit it upfront. 

Reading a book about investors, finance, venture capitalists, or funding has never been very high on my list.  I'd rather curl up with Jane Austen, or laugh my guts out with David Sedaris, or get lost in some historical fiction about France or Spain or London. 

So the decision to read, Get Backed, was rather brave on my part - A sort of 'stretch' project that felt safe because the book had a cool shape, lots of graphics, and what looked, at the onset, like more words than numbers, and more stories than graphs.  So I took the leap.

And you should too!

Whether you're a business of one with no plan to expand, a new startup ready to scale, someone with a nugget of an idea or someone who wants to learn how to connect to an audience, this little gem of a book is for you. 

What it tells you about your customers makes it worth the read.

What it tells you about developing relationships makes it worth the read. 

What it tells you about pitching and presenting makes it worth the read. 

How it makes you think about your business and your opportunities makes it worth the read.

What it tells you about presentations and design and storytelling makes it worth the read. 

So go grab yourself a copy of Get Backed, by Evan Baehr and Evan Loomis.

The layout, the examples, the practicalities, and the information provided will give you a laser focus on how you can better connect with your people, communicate your vision, create the best slides ever, and ultimately fund and finances your ideas - all of your ideas. 

How is the Gig Economy Going to Work? And Be Sustainable.

Although the statistics are hard to pin down precisely, the Freelancers Union tells us approximately 34% of the current US workforce is ‘freelance’ - equating to 54 million people in the United States. With estimates from the likes of Robin Chase and Fast Company suggesting that in the next 20 years those independent workers will rise to 70-80% of us. Liz Ryan reports in a recent Forbes article that we need to  “Wake Up and Smell the Coffee. Employment is Over”.  And in a LinkedIn post, Reid Hoffman, agrees that ‘lifetime employment might be over”, and offers that “lifetime relationship remains ideal” suggesting that our work will come from our alliances.


It likely means that you and your partner and your friend and your brother and your sisters will be working on a contract by contract, project by project basis consulting, creating, and collaborating with each other, with previous colleagues, with new startups, with anchor businesses.  It means you’ll be marketing yourself, operating your own business, working from spaces you chose, and hunting up your own work.  You will be empowered to carve your career how you will like. It means you will be responsible for your own success.


With this ‘new’ economy on the brink of exploding, one has to wonder, how exactly is this going to work?  And be sustainable.


Companies like Uber,  Fivver and TaskRabbit, are evidence of a ‘gig’ economy and are built on leveraging excess capacity showing us how the sharing economy can and does make our lives more efficient and possibly more profitable. But we cannot ignore that  Uber is routinely under scrutiny for under or de-valuing the independent workers, and Mattermark suggest that the company itself is not profitable. Fivver operates on the premise that you can get work ‘done’ for just five bucks, and TaskRabbit focuses on easing the daily tasks in your life like cleaning your house, fixing your repairs, and completing your grocery, laundry and mail deliveries - none of which seems to fit a professional model for being ‘employed’. Add in campaigns like that of the Freelancers Union, which is blogging and tweeting that #FreelanceIsntFree as they create the world’s longest invoice of unpaid bills, and it can make stepping into the world of independents seem rather daunting.


Yet there are others recognizing where this economy could go and all that it has to offer. In her June article How the Gig Economy Could Save Capitalism, Rana Foroohar begins to explore new directions for the gig economy and offers up the potential benefits of a shift from big employee/employer systems to smaller more entrepreneurial system. Her article considers the future of what she describes as community based capitalism and suggests the need for new thinking on labor laws, regulatory systems, and crowd-based capitalism. Faisal Hoque reminds us of the “value of small” in his Fast Company article while painting the global picture of the gig economy and describing the future of work as one where we can work how we actually want to work. He sees the future of a robust freelance economy where both independents and companies gain mutually and beneficially.


The world of work is clearly changing and there is a growing need to establish the necessary infrastructure to support this new workforce . As we move through this transition, where almost half of us will work as solo professionals in the next 10 years, let us be thoughtful and intentional in how, as independents, we can lead this new economy in ways that are positive and profitable and most importantly sustainable for us all.

It's a MAD, MAD World

When you're starting a new venture, or a new adventure, finding a community of support is critical.   Because when you're stepping out in a new territory, you're going to need to find experts, and mentors, and people who have walked a similar road before. You'll need advocates and evangelists, accountability partners and coaches. You'll need to nudge your way to the center of a web of networks. you'll need a group of peers to share the highs, the lows, the missteps, and the wins. You'll need to create structures for collaboration.

You'll need to make sure you don't take all of this on alone. 

Madworks program director, Louis Condon with JILLS cofounders, Megan & Corinne

Madworks program director, Louis Condon with JILLS cofounders, Megan & Corinne


We are forever thankful that we found a great community of support as we began to move THE JILLS OF ALL TRADES™ from an idea brewing in our minds as we collaborated in our basements, to an organized, thoughtful venture. The Madworks Seed Accelerator provided us 10 focused weeks to get our legal ducks in a row, secure some funding, set goals, get feedback, access new networks, and connect with a cohort of peers who made us laugh, extended us needed criticism, welcomed our ideas, championed us when we lost our footing, and made us feel like we were not alone on this crazy ride. 

It really is a mad, mad world out there, folks. Find your people. Know your tribe. Build your community.