“A pregnant founder / CEO is going to fail her company”

As an angel investor, a free-wheeling free- agent in the world of entrepreneurship, I’ll normally say anything that comes into my head. But now, as the cofounder of BetterWorks I thought “maybe I should let this idea slide away – no need to piss off the world of female execs out there”. But the reality is that women in the workplace is an incredibly important topic. We’re missing out on a ton of talent out there and we need to take this seriously.

The Situation: I was contemplating an investment in this awesome crowd-sourced funding company in LA called Profounder. I love the vision: helping local brick & mortar businesses get funding from their community. The founding team, Jessica Jackley & Dana Mauriello, are incredible ladies with exactly the spirit and attitude I’m looking for in founders. We’ve talked extensively, had lunch together and I saw first hand the amazing talent & drive these two bring to the table. And then, a week later I find out Jessica is pregnant…and this dirty little thought pops in my head. I’m thinking how in the hell is this founder going to lead a team, build a company and change the world for these businesses carrying a kid around for the next few months and then caring for the kids after. I can’t say I personally know anything about it but birthing & raising kids seems like the toughest job around. And now I have a founder who has to be a CEO and a mother.

The Decision: Ultimately I decided to invest, namely because I gave a commitment to invest and decided that pregnancy shouldn’t impact my decision. But what concerns me more is that I’m normally very equal-opportunity. In fact I really like working with female entrepreneurs and wish we had more of them. I have quite a few female entrepreneurs in my portfolio companies but the reality here is that I almost didn’t invest and I’m sure a ton of us decide not to invest, support, promote or work with women because of this whole “marriage / pregnancy” hurdle that most women will face in their career. I normally tell people I don’t care about your sex, race, religion, sexual preference – these things just don’t mean a bag of dogshit to me.

Yet, I almost didn’t invest so it must mean something and I’m definitely not as equal opportunity as I thought. And even though I ultimately decided to support Jessica and Dana, there are a ton of Jessica’s out there that won’t get the same treatment. And this brings me to my big question: Should I go out of my way to support female entrepreneurs? Should I give female executives, founders and others women an advantage in funding, hiring & promoting?

I talked to Jessica this weekend at Summit at Sea and told her my thoughts. I was a bit ashamed – walking up and telling an entrepreneur you’re backing that you have doubts, particularly something like this, is never an easy chat. But it is something we should do; I really love being direct and we do owe it to each other. Surprisingly Jessica wasn’t upset and I asked her if it was cool for me to write about this.

She gave me a warm yes and so here are two key points rolling around in my head right now:

• I have doubts once I think of you getting married, having kids and being distracted from work. Right or wrong this is something I’m thinking
• We need more women in the workplace. Look around at founders, boards and execs and you’ll all realize women are grossly under represented in the workplace

Recognizing this doubt I’m now asking myself if I should give preference to women. What do you think?

And before you answer, take the time to watch Sheryl Sandberg’s TED talk. I watched this last night as I was thinking about this topic and she brings up some great points. But the issue I have here is that Sheryl’s talk is directed at women – telling women what they should do. What I want to know is how should we as men deal with this?

• AUG 2010: Paige daydreams “Happiness in the Cloud” + “Google Perks at Costco Prices”
• SEP 2010: Recruit cofounders // Market Research
• OCT 2010: George, Paige & Zao – Concept to Design
• NOV 2010: Recruit Early Team // More Design // Refine Business Model
• DEC 2010: Seed Round // Hire Engineers (KW, Ian, Jonathan) // Hire Sales Team (Robyn, William, Scotty) // Win Early Customers
• JAN 2010: Prototype Complete // Hire More Sales (Mike, TJ, Tracy) + Product Mgr (Ron Yang)
• FEB 2010: Alpha Release // Hire Marketing Director (Chris Spore)

Quick bit of advice to founders: Time is your scarcest resource. Move quickly. ‘nuf said.

And from an anonymous quote I remember walking by my first two years at West Point: “In the absence of further orders…ATTACK”

But I want to talk about WHY we as investors care about Boot Strapping. Or at least WHY I care. Bootstrapping is an indicator that you’re the type of self-sufficient, bold, confident, passionate entrepreneur that we want to invest in. It’s painful – it takes months & years of sacrifice and it will drain your energy. You’ll give up girlfriends (or boyfriends); you’ll give up evenings that could be spent with friends – you’ll toil away in your miserable little efficiency condo cranking out code or convincing people to use your early product. You’ll beg & borrow your way to success and MOST of you will eventually give up. Nothing wrong with that at all – if you can’t handle the sacrifice we don’t want to invest in you because you have to invest in yourself first. We want people who can make short term sacrifices for long term gains – we want leaders who are willing to sacrifice their personal comfort to bring a dream to life.

Simply put, boot strapping is just a really good indicator that you’ll be a good founder.

Lot’s more to say but I’m out of time and I’ll leave you with this video of our last discussion on bootstrapping

And, my apologies if the chat sounds rambling. I hate preparing for discussions and interviews and always “make it up” on the spot. As a result you’ll hear me move from such topics as Intelligence Collection, the war in Iraq, Gay Marriage, Wikileaks, blippy, twitter and online dating… but believe me there is a common thread that connects these topics together.

Enjoy, and welcome to 2011!

As an example, I give you one of my most recent messages from linkedin:

“I am privileged to contact you of my intent to invest a huge fund in your country, with interest in the following sectors: Banking, Real Estate, Stock Speculation, Mining, Transportation, Oil & Gas and Tobacco. If you think you have a solid background and idea of making good profit in any of the mentioned business sectors in your country and you are interested, l will need your email address for the detail of the investment or you can contact me through this email sim0000031@yahoo.com, . I look forward to hearing from you.
Regards,
Michael Simone”

Sorry Michael, my schedule is full for the next ohhh decade or two…