The rockin’ entrepreneur women the venture world is missing out on

One of the most unexpected benefits of starting my own company has been the chance to meet and form virtual friendships with some incredible, smart, inspiring, and gutsy women entrepreneurs. When I started my career in venture capital I thought that I would find many women entrepreneurs to back. Then the dark reality hit and I found out that there were not that many women entrepreneurs knocking on our firm’s door to look for funding. For the record, we did have 5 companies in our portfolio with women CEOs, but 4 out of 5 were brought in later and were not founders.

But since leaving venture and striking out on my own I’ve met some pretty awesome women entrepreneurs who are serious about their businesses but also serious about their lives and having more in them than just their business. Many are also moms and they are building their companies in ways that would make any venture capitalist cringe — they are working from their home offices, they (like I) take off in the middle of the day to pick up their kids from daycare or school or play with them outside, and their workday is as far removed from the traditional 8-6pm schedule as possible. Meeting these women has been an amazing experience and for the first time in my career I am developing a professional network that includes women I actually like and respect and want to interact with. They are supportive, they are not catty or bitchy or whatever the stereotype suggests — which is true too often — about women interacting with each other.

These women are running and starting different types of companies but they share a few things in common:

• Many have left successful corporate or more traditional careers to become entrepreneurs
• They see entrepreneurship as a way to gain more flexibility and a better ‘balance’ between work and family
• They are choosing to finance their businesses without taking venture funding, at least in the early stages, and they are incredibly ingenious about finding ways to fund their operations (bartering services/marketing with other women-owned firms has come up more than once)

I’m gaining new perspective about why there might not be as many women entrepreneurs seeking venture funding out there. I still maintain that those who do want it should have more access to it and one of the reasons they don’t is because there are so few women in venture capital. (To deny that it’s easier and more natural for women to network with women and for men to network with men would be silly.) But as I meet more and more women who are serious about building successful businesses but don’t want to do it with venture funding, at a venture-backed company pace, I am starting to think that one of the reasons more women don’t get venture capital is because they don’t want to.

So that you get to meet them as well, here are some of these rockin’ women entrepreneurs I’ve been lucky to meet recently (most virtually) — go give them a shout out!

Penelope Trunk

Aruni Gunasegaram

Naomi Dunford 

Wendy Piersall 

Aliza Freud 

Being an entrepreneur means learning how to know when you’re wrong and doing it quickly

When people ask me why we didn’t take venture capital to fund Work It, Mom! I give two reasons, both very different:

1. Part of my motivation to leave a career in venture capital was to see my daughter for more than 20 minutes a day and have some semblance of a life. I’ve invested in venture-backed companies and I think I have a sense of what it’s like to run one. At this point in my life, it’s not what I want to be doing.

2. I launched Work It, Mom! because I believe that the 30 million working moms in the US need an online community and resource dedicated just to them. But I don’t know if this means that we can actually turn this into a business. Do working moms have enough time to spend online and be involved in a community? Can our niche audience be big enough to attract solid advertising revenue? We don’t have answers to these questions and we can’t have answers until we run with this for a while and figure out if the business plan works. I don’t want to spend venture money chasing the wrong plan–a million dollars spent on marketing the wrong product is a waste of money.

I’ve gotten a lot of compliments for reason #2. People tell me that it’s “very sober and responsible thinking” and that they are impressed that someone with venture capital connections chooses to bootstrap the company and face the many difficulties that come with that choice (not nearly enough resources, no marketing budget, huge personal financial pressure, you know what they are.) But to me it’s the most obvious one.

And I was glad to read this post by Fred Wilson talking about failures and successes in his portfolio. What he has observed is that 2/3 of the companies in his various portfolios have partially or completely transformed their business plans in their course of their life and most of the successful ones did. Being a successful entrepreneur does not mean having the greatest idea ever that gains traction as soon as you launch it (which would be nice, by the way.) It means trying different directions and figuring out quickly which one is the winning one, without spending tons of capital in the process.

I find this perspective helpful, and the fact that it’s based on data reassuring. I don’t know if Work It, Mom! can be a huge business success–it’s so young and it’s so early to make predictions–but I gain some comfort in knowing that by bootstrapping it while we figure out IF our business plan can be successful we’re doing what has helped some other successful companies become such.

Having your own business means being scared every single day

Since we just moved I’ve been meeting new people all the time. Inevitably the “What do you do?” question comes up to which I answer that I started my own company recently. The responses usually take the form of “Wow, that’s exciting!” and I nod and smile politely in agreement.

But let me be honest here. What I’ve learned from my six-month stint as a full-time, no security blanket entrepreneur is that mostly, it’s freakin’ scary. Yes, I said scary. It IS exciting, and wonderful, and amazing, and gutsy, and interesting, and fulfilling, and many other adjectives, but every single day, it’s scary. And it’s the kind of scary that I’ve not experienced before–a deeply ingrained, constant state of scary vs. something that just comes and goes. To be perfectly clear–or too honest, as a friend who has been reading this blog recently said to me–here are some things I am scared of:

• I am scared of failure. I am really really scared of failure. Work It, Mom! is something I’ve created and I’ve gone out into the world saying “Hey, world! We need a community for working moms called Work It, Mom! and I am going to create it and make it into a real business.” The odds of success are tiny, the fear of failure is huge.

• I am scared of what my friends, family, and professional colleagues/contacts will think of me if I can’t pull this off. I wish more people talked about this openly. No, I am not doing this for anyone else, but to say that I don’t care what anyone else thinks is dishonest. We all care, opinions matter. I don’t want to let anyone down.

• I am scared of how working 15 hours a day will affect my family, my relationship with my husband, my daughter’s view of her mom. I’ve tried my best to make sure that I make time for them, but it’s a constant challenge.

• I am scared of the financial impact that potential failure can have on my family. I am the main breadwinner (currently on sabbatical in that capacity:), and it’s my responsibility.

And here’s one more, which you are hearing here first:

• I am scared of finding out that I’m not cut out for this. During the past 10 years of my professional life I always thought that what I really wanted to do was start my own company. I did things on the side–like this one–but Work It, Mom! is my first full-time entrepreneurial venture. It’s been tougher and crazier and riskier and more challenging than I imagined or ever experienced before. And I am scared of ever finding out that maybe running my own company isn’t something I can do. This one is the scariest of all.

Why am I sharing this with you? Because every day I get emails asking me about how I got started with Work It, Mom!, how the site came together, how we’re building the business. I try to reply with helpful and specific points. But I want to make sure that I am perfectly clear with every single entrepreneur, freelancer, small business owner or potential small business owner out there:

CAUTION: This is scary stuff.

My to-do list is always a mile long, but I realized recently that what I do every single day, without fail, is fight my fears. It’s the toughest thing I do as an entrepreneur. And there are days when I feel like I am not sure I can keep doing it and days when I know with 100% certainty that I can. The emotional roller-coaster analogy we often hear about running your own business is extremely accurate–I am living it.

I love doing this. If something happened and Work It, Mom! never went further than it has to this point, I’d be tremendously proud of it, of our community, of everything we’ve achieved, of what I have been able to do. I have BIG plans for where this goes and some great people working with me to help make it happen. The moments when I feel like we CAN do this are amazing–I feel like a superhero! They are as amazing as getting an email from a member saying thanks for creating this community or reading a post where community members are being incredibly honest or helpful with a fellow member who needs it. That stuff is magical (so please keep it coming!)

But it’s still scary.

Do you have your own business? How do you face your fears? How do you work and push through them?