Penelope’s haters: Where are they now?
Detail of Watermelon & Knife by Wayne Thiebaud (1989)
The setting: I’m buried—raising kids while running a startup. It’s 2010 and I’m one of the only female founders getting funded. I feel obligated to speak up, so I write blog posts telling women: startups are BS, just say no.
The Real Housewives of Venture Capitalists
Alexa Tsotsi said I was terrible for women. Jessica Wilson said I was tone-deaf to feminism.
So where are they now? Both married venture capitalists. Both talk about their amazing businesses—built with their husbands’ money and networks. If they get bored, they stop. They use their husbands’ money for schools and childcare, then write about their accomplishments as if they’re on a level playing field.
Women who don’t take risks shouldn’t advise women to take risks
Raising money for a startup is high-risk hell, which is why women don’t do it. The research is clear: risk tolerance isn’t a culture problem we can fix by telling me to shut up. Risk tolerance is based biology, shaped by in-utero testosterone.
Magic equation: Privilege Laundering + Feminist BS
Sarah Lacy was a tech writer who married a venture capitalist. A former coworker wrote this profile of her:
In late 2011, Lacy left TechCrunch—which had been purchased by AOL the prior year—while on maternity leave with her first child. “I took my baby fundraising with me,” she says, recalling another thing few working parents would dare do—especially given that less than 3 percent of venture funding goes to women-led startups, according to Harvard Business Review, never mind startups led by moms with a newborn.
Here’s my rewrite:
In late 2010, Michael Arrington sold his company, TechCrunch, to AOL, which left Sarah Lacy unemployed. So she got pregnant. “I took my baby fundraising with me,” she says, describing the process of asking her husband’s friends for money. This was all just a little distraction from bonding with her new baby.
You know how the list of the richest people now has a caveat for wealth that was self-made versus inherited? I think there needs to be a caveat for women’s achievement: did their family actually depend on the work they did or was it an expensive hobby? Because taking a risk when you need the money is completely different.
It’s easy to use someone else’s money to buy yourself a job that looks great on paper. So when you look at women who say they worked while raising kids, ask if you’re holding yourself to standards that only someone with a rich husband could meet.
Don’t pose as a breadwinner if you plan to marry rich
The more we promote life as a meritocracy, the more we enable this privilege laundering. Each woman with spousal support who brags about her success makes it harder for women without that support to admit they can’t compete on equal terms.
The more we promote that life is a meritocracy, the more we leave the door open for people to launder their privilege. That’s what Jessica, Alexa, and Sarah are doing. None of them earned enough money to support a family where they lived. So they used their skills to marry someone rich, and now they use that marriage cache to make it look like they’ve done something remarkable.
The problem isn’t that they married rich. That was a great idea. The problem is the way they encourage women to take risks they never took themselves. So how about if we tell girls the truth about #goals: All of your goals are a lot easier if you start by marrying someone who can support you. That’s ambition.
Telling the truth requires honesty and integrity.
Thanks, Dana. Also, thank you for commenting seconds after I post. I never know how a post will do until I see a comment. You give me a sigh of relief.
Ha, I could read your re-writes all day. Makes me wonder how much woman behind a “woman-owned business” there really is.
That makes me happy to hear because it was so fun to do the rewrite!
“The research is clear: risk tolerance isn’t a culture problem we can fix by telling me to shut up.” I laughed out loud–not LOL laughing–the real kind.
This reminds me of the NYT article, which my take away was it’s so hard to work and be a mom.
https://www.nytimes.com/2025/08/09/business/manager-performance-work-advice.html?smid=url-share
Were you trying to prove that you could be both a good mother and a successful businesswoman, or that you couldn’t?
My point, when I was writing about women and startups, was that women don’t do startups because they are insanely high risk and most women don’t want to engage in that sort of risk taking. So we shouldn’t be telling women to do more startups when they are already making good choices for themselves — by not doing startups. We should reinforce that women make good choices for themselves.
I think you’re also asking if I think women can work and care for kids – – not really part of this post, but as I’ve said before, anyone competing at the top of their field needs a stay at home spouse. The jobs are set up assuming there’s a stay at home spouse.
Penelope
And yet, there you were, doing the thing you were telling other people not to do?
I wasn’t really asking what you think, or thought, other people should do. You talk about that a lot. I was asking why you were doing what you did.
Do you mean telling women not to do startups because they ruin your life? The year I wrote those articles I gave up my position as CEO of my startup and moved to the farm.
Bang on. The ‘buying yourself a job via hubs money’ is so true and annoying. Just accept you live off of him – intentionally – and be glad about it. (is my message to said recipients, suspect they aren’t listening!)
Came here to say you are completely right. Women cannot have both things a successful career at a high level and children that are raised well unless they have a stay at home spouse. That has been my life experience. I applaud your effort to provide this message. I hope more young women see it.
Thanks, Isabel. I appreciate the encouragement!
Isn’t it interesting how young women don’t get such messages these days? It seems they would have to be in a conservative religious context to have a chance of hearing them. I was well into raising a kid before it really dawned on me that you can’t have both a big career and a well-raised kid at the same time. And there were so many other messages I didn’t get as well – like women at age 35 are considered “advanced maternal age.” I nearly died when the drs gave me that label when I first became pregnant – I thought I was in my prime child-bearing years! lol!
I had that experience too — I was like, wait, I’m not old. And they thought I was nuts that I didn’t know 35 was old.
My wife and I lived for a long time in Indiana’s wealthiest suburb. We make top 10% money and we lived in the lowest-class neighborhood in the suburb, if that tells you anything.
The town has an utterly charming brick main street lined with boutique businesses. 90% of them are woman owned — their husbands made beaucoups de bucks doing whatever they did, and their wives used some of that money to open their shops. I have to assume it doesn’t matter too much how profitable any of these shops are.
Growing up blue collar as I did, I have a lot of resentment over all of this.
When I lived in rural Wisconsin there was a town — Mineral Point — that was all odd stores that were never open. It was Chicago people pouncing on economic development incentives and then using the stores as a tax deduction. That really opened my mind to the range of BS that’s possible in brick and mortar.
I have young boys. What should we encourage boys to do?
Thank you for asking! I am gearing up to start writing about education again, and I have strong beliefs about what a waste of time school is for boys.
The reason there is no correlation between school success and workplace success is because the workplace rewards stuff boys tend to do well: ranking everyone, kinesthetic learning and games. But school surrounds boys with teachers who don’t do any of this well — because women who do this well don’t become teachers.
Boys should stay out of school as long as possible, find stuff they love doing, and become very good at that. Because boys are also better than girls at hyper-focus. Colleges reward hyper-focus and hyper-competitiveness.
I have been writing about this for a decade on my education blog: education.penelopetrunk.com.
You know I’ve been a long-time fan, but today I’m subscribing because you deserve to be paid for dropping truth bombs like this.
Really? That’s so nice. Thanks for letting me know. You make me more brave.
Thank you for putting into words what everyone does but nobody really talks about.
Everyone in my circles seems to be doing this but nobody really admits it. And it’s always the women working part time as an OT (during school hours) artist, boutique chocolates, realtor, etc. Never the man.
As for raising boys, as I read, “stay out of school as long as possible” it occurred to me that one thing a boy could do during this time, to feel better upon entering public school, and for boys already in school, is to become good at something. (don’t ask me what “good” is) An early 1950’s student self help book at my secondary school advised a student to become good as something, anything, “even the game of tiddly winks.”
As an adult, how I interpret that advice is that it gives a boy some everyday self confidence… and confidence that future accomplishment is possible. As an adult, without teachers or deadlines, I taught myself a new keyboard (Dvorak, versus the traditional querty that we learn in typing class) because I had faith that I could do it (without flaking out) because I had already learned things well. (including a beginner typing class at night school)