I wrote a piece years ago on some blog that is no longer public titled A Decade Late and Millions Short. The title was meant to convey the idea that female founders have a much bigger problem than being chronically "a day late and a dollar short."
It was inspired by the article My startup failed, and this is what it feels like... (discussed on Hacker News). It was written by a young female founder, Nikki Durkin, who made it through the Y Combinator program and then, later, saw her start-up fail.
She repeatedly had to rebuild the product and also had major surprises sprung on her, for example:
We rebuilt the 99dresses product and launched it in the US.
signed a $1.2 million seed round with a group of investors ... and the next day my two “co-founders” decided to tell me they were leaving the company without even a hint of warning
We rebuilt 99dresses again and launched it in the US...
My feeling was that her gender was a factor in that guys who work together can go out for a beer together, establish trust and someone with more business acumen or coding experience can nudge the business in the right direction earlier. Also, I feel like probably her gender in some way contributed to her being blindsided by the departure of her two co-founders.
I originally thought I would just republish the original but I don't think that works. It very bluntly talks about an issue I feel is central to keeping women out of business without anyone necessarily trying to do so: The fact that most gatekeepers are male and this creates a situation where both she, he and everyone else need to sort out the question "Is this business? Or this a sexual relationship?"
And I'm disinclined to simply blame men for that which seems to be the default norm for a lot of women.
Businessmen need to be trusted and have a good reputation. If they don't know if you are looking to sleep with them or not, the safe way to bet is to protect themselves.
And most women don't get taught how to behave professionally. The reality is that some women will be happy to marry well and stop working, so, no, men cannot simply assume "She's a business woman or professional. This is not a personal or romantic relationship."
The least worst reaction I've gotten from men was to the effect of "I'm married. Go be all personable and friendly with SOMEONE ELSE." In other cases, I felt clear married men were up to shenanigans and happy to have a good excuse to talk to me and, no, it wasn't really going to further my career goals.
I think this need to establish trust without it leading to either an illicit affair or her marrying well and thereby de facto ending her career is the hill upon which most "serious careers" for women dies.
Women have "an easy way out." Men typically don't.
For men, you make a good income or you don't qualify for The Good Life with a wife and kids. For women, you can either have a serious career or marry well and support his career.
So some women -- and I'm sure there are no stats on this -- when faced with the fact that a man has power over her career and is romantically interested in her may decide to not heroically take a stand and just accept the deal.
For some women, this may be a deal with the devil, a gilded cage. We are unlikely to hear later that she regrets the decision. If it made her (nominally) "rich" (reality: it's still HIS money, not hers) and in the public eye, good luck getting sympathy for that.
I regret making clueless public remarks about the start of the relationship between Bill and Melinda Gates. She initially told him "no" and gave a polite excuse to one of the founders of the company for which she worked. He emailed her later that day.
Maybe the subtext there is she realized her career at Microsoft was over no matter what she said or did and she decided to take the gilded cage. They are now divorced, so maybe that wasn't as good a deal as she imagined it would be.
I began reading business books and articles in my teens. In my twenties, I had a blank book where I recorded snippets of wisdom about business. In my thirties, I had a business bank account and registered the fictitious business names of several tentative businesses.
No, I've never really had a successful business.
So I have a very longstanding interest in business and haven't figured out how to make it work. Thus, I have looked to the lives of other women for clues as to what might work.
The moving company Two Men and a Truck was founded by a woman when her two sons were home from college and wanted a summer job. Cool, I have two sons! And that seems to have done nothing for my business aspirations.
I took a keen interest in Elizabeth Holmes and Theranos because I have a serious medical condition and have gotten dramatically healthier. Theoretically, I have the potential to start some kind of medical company.
But she spent years in the public eye without really producing a product and it ultimately went down in flames as a fraud. Sadly, I did not find this shocking.
She was a pretty young woman who claimed to be celibate in her twenties due to her devotion to her company. We later learned she was secretly living with a much older man who nominally invested in her company.
I occasionally made a few very conservative remarks about it on Hacker News for which I tended to be dismissed or lambasted. Given her age and my experience with being constantly hit on by men and not taken seriously professionally, I always believed she likely was lying and sleeping with powerful men who were nominally backing her company only not really.
In reality that would be a situation where these men were de facto paying for sex. It would not be a good way to get the kind of critical feedback necessary to found a successful company.
I'm still waiting to hear that Sunny Balwani wasn't the only rich and powerful man screwing her while pretending to be interested in her company. I always believed "celibate" was a cover story for why she didn't "have a boyfriend" that claimed "Why, no! I'm not blowing all these men, some of whom are infamous lady's men! I'm just very very serious about MY COMPANY!"
Sex and business CAN sometimes successfully mix. Another female founder I kind of politely cyberstalked is Jessica Livingston.
She was a pretty young woman several years younger than Paul Graham and the only woman founder of four co-founders for Y Combinator. And she "dated" Paul Graham whom she later married.
Being the jaded "men just treat women like a piece of ass and don't take them seriously" type who saw the Theranos debacle coming from a mile away, I spent a LOT of years baffled and fascinated that Y Combinator was a successful company and not another source of scandalous headlines. In fact, it's a multibillion dollar company that has helped a lot of big name companies become big name companies.
The short version is that Jessica Livingston did not, in fact, found a company with three guys and "date" one of them. That's not a lie but it's not really how that happened.
What happened is she met Paul Graham at a party shortly after he and his co-founders sold ViaWeb and she and Paul began dating. She was job hunting and being strung along and not getting a job offer, so at some point he said "Let's start our own company."
Paul Graham was an experienced and successful entrepreneur. Jessica Livingston was in financial services. They founded a company that finances other companies.
Livingston once said that YC was "an accidental success." This suggests to me her being a successful female founder was "an accidental success."
She has talked about how much she and Graham batted about ideas while dating and while she was job hunting and talked about how good he is at that. Yet the success of YC apparently surprised her.
In other words, she didn't have business acumen at the time the company was founded and didn't understand what Graham was doing.
She was probably hoping to marry well. He had just sold his business and her biological clock was ticking and as an extremely pretty young woman, her head was smacking the glass ceiling hard. She probably would have been content to get married, quit and raise kids.
Graham has a PhD and she has a bachelor's degree. I'm guessing he probably got tired of listening to her complain about how she got treated at work and while job hunting and wanted to marry her without having to listen to this forevermore, so he gave her the opportunity other men wouldn't and founded a company with her.
One of them said it was initially just the two of them and within a day or two he contacted his two ViaWeb co-founders and asked them to come on part-time and help with a portion if it. Graham has said they initially hid their romantic relationship to try to appear more professional.
So really this was a company founded by a dating couple who later married and it was primarily Livingston and Graham who ran it. The other two co-founders weren't really that involved.
Which clears up for me personally why this didn't go down in flames: It absolutely was NOT the case that some pretty young woman cofounded a company with three random men, got asked for a date by one her co-founders and said "yes" and somehow did not end up being fought over by the three guys while the company went to hell in a hand basket.
But it took me years and years to piece that backstory together from little snippets here and there. It was so hard to put that picture together you will have to "trust me" because I can no longer cite my sources for those details.
The reality is that YC is essentially a woman's multibillion dollar company. Paul Graham worked there only a few years and then retired, hiring TWO people to take over part of his work (Sam Altman as president, Dan Gackle as moderator of HN) and continued to work part-time at Office Hours and probably continued to give Livingston feedback on critical decisions over dinner or whatever because he was the more experienced entrepreneur and they happened to be living together.
But Paul Graham designed the company around HER domain knowledge -- financing -- and YC was successful because:
1. It innovated financing contracts.
2. It chose candidates to finance based on the PEOPLE, not their proposed business idea.
Paul Graham has called Jessica Livingston "social radar" and has said that after he and his two ViaWeb co-founders interviewed people, they would turn to her and ask her opinion. The candidates were surprised. They likely thought she was a secretary, not a co-founder.
So betting on people, not business ideas, was playing to her strengths. Paul Graham stuck around long enough for his wife to pick up enough business acumen for the company to not die, then retired from being the public face of a woman's successful business.
While it's fascinating to me to figure that out, I have no idea how a woman could replicate her success. She wasn't trying to start a company. She was probably looking to marry well and her boyfriend had other plans for her.
So I remain clear that the question of sex is a major stumbling block for would-be business women, but no closer to having reliable suggestions for how to get around that in order to succeed as a business woman.