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.
It seems like you went full speed ahead at being a businesswoman with children.
And then that stopped working well for you, and you started talking about how nobody should do that.
And then you went full speed ahead at moving to the country and marrying a farmer.
And then…
What else that you’re doing right now is something nobody should ever do?
I don’t know. Do you?
Also, though, I did a lot right. That other people should do. But I don’t write about that. Because I figure that if I knew to do it then so did everyone else.
I think I’d probably find a post about what you did right, but you believe everybody else already knows, very interesting.
Sometimes it seems to me like I, and others in my family, have lived our entire lives doing things you think are a terrible idea. And it’s all working out great for us.
Maybe we – and some quieter readers – are also doing some things you think are great ideas.
If you’ve lived your entire life doing things I say not to do, and it’s working out great for you, then that’s so nice for you. I’m not sure what else to say. Do you want to write a guest post about that? I don’t take a lot of guest posts, but you’ve been leaving great comments for a long time. So I bet you’d write a good post.
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.
My wife and I have a son who is 24. We supported him through the long journey of primary and secondary schooling, paying attention to his interests and what we thought would be good, which largely didn’t end up involving academics.
We started by putting him in Waldorf/Steiner-inspired schools in preschool, kindergarten, and elementary school, where the parents and the school shared the view that young kids should be using their imaginations and not constantly be exposed to images in media. Also, he had a nature day there, where one entire day of the week was devoted to being in nature.
Support for respect for individual paths ended around 5th grade when his school decided that it was hazardous to their future to not keep their students up with the public school students because students transferring to public schools were behind public school students in progress and that seemed to make the school look bad, which wasn’t our concern. As a result, my wife home-schooled him for 6th and 7th grades, which he enjoyed. He attended an outdoors program one day a week, took a ceramics class, played music, traveled to out-of-state museums focused on the natural world, and also did some academic work, including a fair amount of math. That ended when he decided he wanted to play baseball in high school, and wanted to attend public school for 8th grade to get to know more kids.
High school was both inspiring and disappointing. His favorite class was auto shop. He swapped a couple of engines and transmissions, including an engine on his own truck, which he drove home on the last day of school in 12th grade. This class ended up being the only thing keeping him in school.
He was not able to take wood shop because the facility was taken over by an academic program in which he was not interested and to which all students who worked in the wood shop must belong. My wife volunteered at the school attempting to resurrect the cooking program, in a classroom with 10 ranges, which ended up being turned into a computer lab. There was also a sewing program, with multiple sewing machines, that got canceled as well with the sewing machines stuffed into a closet. The school was favoring high-tech over basic life skills.
On the academic side, he learned how to write and enjoyed that he could write reasonably well, maybe even more because his 5th grade teacher had ridiculed him about how little he wrote. He liked learning U.S. history and politics, but didn’t care for teachers with what he saw as obvious biases toward a particular political side.
More of his focus and interest was outside of school. He stopped participating in baseball. He worked for a summer as a carpenter’s assistant building a garage. He got a job in the equipment rental department of a local hardware store and learned how to fix small engine-powered devices. He bought a series of diesel pickup trucks, fixed them up, and sold them. He did the same with multiple small powerboats.
Community college was canceled during the pandemic, so he was not able to study welding beyond the first year. He got jobs working construction for a sewer line company and a remodeler. After a couple of years, a neighborhood friend suggested he work at the local water district where he worked, so he applied for a job there and got hired, first reading meters and then fixing water main breaks. A lot of that water main repair work was at night paying overtime and getting a paid day off the next day when he worked long enough at night. He gets promotions and is valued for his work. He made over $100K last year and expects to do the same this year.
It was a continuous set of experiments to figure out what worked and what didn’t. We had to keep trying stuff and evaluating how the stuff turned out for him. As well, we had to keep focused on what was working for him even if it didn’t work out so well for the schools.
This is a great example of how much time and resources it takes to homeschool. It’s so much easier to start homeschool, and then blame external circumstances for homeschool not working. But the thing about homeschool is it’s the parents job to overcome the external circumstances. And that’s a really heavy life.
I have met very few families where homeschool was a better alternative to public school. I say this with a heavy heart. But the more families get off the beaten path, the more responsibility families have for making it work. And there is no support for families once you’re off the beten path, so going back doesn’t work.
Your story is an excellent illlstration of this issue. I cannot stress enough that you can’t do alternative schooling until high school and then put your kid in high school and think it’ll work. High school is the culmination of mainstream schooling. It’s not fair to the kid.
> This is a great example of how much time and resources it takes to homeschool
It took a lot of my wife’s time. She registered a home school with the state; I forget what we got out of that registration. He liked it for a couple of years and then, because he is so social and wanted to be around more kids. A lot of the kids in the homeschool community seemed like that’s the only schooling type in which they would fit, and my son couldn’t relate to them. He started doing 4-H during that time and that helped a lot for social connections as well as developing additional real skills. Boy Scouts didn’t work because the kids in his troop were heavily involved in video games. He never wanted a gaming console, and played video games only occasionally at friends.
> start homeschool, and then blame external circumstances for homeschool not working
I think it worked well for the length of time it existed. Then, my son indicated he wanted to move on. Even today, there’s a lot he appreciates about that time. Another experiment.
> there is no support for families once you’re off the beaten path, so going back doesn’t work
That’s what made it challenging for those who did leave the Steiner/Waldorf schools, and why, I imagine, those schools migrated closer to public school curricula. The school my son had been attending had mostly studious girls as students, so that shift probably was accepted by a lot of the families. Years later, there ended up being only one other boy, which was a problem. A number of times we chose what looked like the least worst option.
> you can’t do alternative schooling until high school and then put your kid in high school and think it’ll work
Yet another experiment. Although, we didn’t so much put him in high school as much as he asked to go to high school, and he had the sense of wanting to make the transition to public school at 8th grade.
From 8th grade through high school graduation, he connected really well with a few teachers, including a private baseball coach of his, to the point where he could go back and visit any of them (he travels every year a couple of days to the rural area where his baseball coach now lives). He did the best in the classes where he had the best relationships with the teachers.
Meta-comment: I usually avoid supporting hijacking threads in forums like this but there’s no place for anyone but Penelope to start threads. Maybe this would have been better served as a thread in the mailbag. These comments get buried in a page that is not devoted to this topic, so it makes it harder for people to find these comments if they are not interested in the main thread and are just looking at thread titles. That’s the main problem with hijacking threads.
Posted to mailbag here:
https://mailbag.penelopetrunk.com/2025/08/25/what-happens-to-homeschoolers-in-high-school/
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.
You provided a private coaching session with my son Griffin three years ago, when he was 17, to help him explore his next steps – college or entrepreneurship – and we still talk about it to this day. Just last night, I was sharing the main idea from this article with him, and he laughed and said, “She told me I should marry rich too!” I had totally forgotten that part but it’s still solid advice, lol!
LOL I love that he remembers that. Thanks for telling me.
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)
Well done and said Peneope. I wish that this much insight could be displayed by others. I have always appreciated your insights when it come to an unsanitized view. Thanks.
Just lean in!!!!
But not if you’re on a treadmill…