But it’s true. The job of a small business owner to keep the business alive. To make smaller, more prudent bets that will optimize but not really make huge waves. Because your livelihood is dependent on it. If you mess up, chances are you’re not making rent. I know this because my parents had a successful small business for almost 40 years. I know exactly what the price of a wrong move is and the reward of a right one.

And as incredible and as successful my parents’ business was, it’s not what I’m doing. I’m not building a small business to create value on a smaller scale. I’m supposed to making big bets that stand to completely change the status quo.

So every day I’m pushing to keep my business alive instead of testing to see what will kill it, I am failing our purpose.

This is an incredibly hard thing to live. Because it might sound simple in theory but in the reality? I know these parents we’re serving. Their kids. I know the caregivers in our community - their lives, their realities.

So every change we make, every test we run has real, non-theoretical implications. It ripples through the whole system. And a system that deals with humans? And little humans at that? Well, any change is more complicated.

It doesn’t change my job though, because while I fret and worry about the thousand families or the hundred caregivers we have now, we jeopardize our opportunity to figure out the thing that will really serve the millions.

And maybe we end up being one of the 95% that never make it. But I’d rather know that after we’ve had the chance to throw everything we have at the problem and not wonder once we run out of money (and therefore time).

I can’t tell you how hard it is to not be my father’s daughter. To not wake up with the instinct to keep this business alive. To not do everything we can to carefully nurture it along.

It is a hard thing to realize that the job I signed up for is the one that the works to figure out the impossible.

And the impossible is only possible with big bold bets.

The kind that can kill a company.

But can change the world.

*From Aug 16, 2016, when I was building Poppy.

In that way that some families pass on a cottage or some heirloom china, mine bequeathed me this deep love of seeing new places. Of flying off to some new place landing and taking that first breathe of foreign air.

In many ways it's what I live for.

I found this from an old journal and I marvel at the uncertainty of a mama with two babies at home - only 5 and 2.5 at that point - little moments of doubt that still exist as the girls are 13 and almost 11 but I see how much more confidence I have in myself now. And them.

May 3, 2017

I am sitting here in the moments before takeoff when there is nothing to do but think. I cherish these minutes even as I'm quickly bored by them.

The plane makes the turn into our runway and starts to pick up speed. That welcome acceleration after a tepid march to the runway.

My thoughts drift. To my girls first. Always. They'll still be tucked in bed ( likely our bed by now) cheeks flushed with the slumber of babes, tiny hands clenched in some dream.

I'm often asked how I balance both halves of my life and while everyone knows I hate that question. I always respond that it's not the tactical day to day that's the worst. Because I'll be the first to tell your our incredible nanny does most of the heavy lifting there.

It's the philosophical. It's the self doubt of wondering if I'm doing right by them. Sure I'm a great role model but am I a great mama?

It's impossible (and impractical) to ignore the realities of my absence. I know my girls are growing up with a reality that doesn't have a mother home for significant parts of the week. And while there are positive role modeling effects I worry more that I'm not the one that my 5 year old runs to with stories about school. Or that my 2 year old associates words like "O-feece" and "mama way" (mama away) as much as anything else.

The plane climbs higher now. The break through the clouds. The sky is piercing blue and the clouds a comforting if deceptive blanket.

There are no answers. Just the questions.

The seatbelt light dings off.

The indulgence is over. Time to get back to work.

Something that's been increasingly on my mind: new ideas happen by making new connections on existing concepts. But that means you need to time to both explore many disparate idea spaces and the idle time to explore the connections.

Women don't have that time to tinker. Idle time to play, to waste, to ponder.

It starts as girls, socialized for care work that has few boundaries and can fill any open space, and it continues as they get married (or even just in relationships) and start to take on the care work of running a home and families.

(Meanwhile, boys and men have social constructs that preserve this play - sports, "man caves", video games...)

And it gets worse with kids - the data overwhelming shows that even when there is division of labor with a partner, women end up with the work that is more frequent and time sensitive (meals, registrations, pick-ups), while men take on the less frequent, done on their time (garbage, finances, maintenance). Worse, because women are the point person on all of the information and the logistics, they always have to be available, in case they're needed.

And what it means is that ultimately, women never are in control of their own time.... never have 4 hour stretches to just ponder or tinker or pursue something of no explicit worth.

If women don't have that, we don't have the conditions for innovation. For new ideas, for following red threads.

And thus, we're great for consumption, not for innovation. 

That, I believe is one of the biggest things we're not talking about and has massive implications on how the future plays out.

Earlier this week the universe conspired so that friend/classmate Abby Falik and I could sneak in an impromptu 20 minute walk when I found myself in Berkeley.

Shocking how many things we could cover in those 20 minutes, but it was her parting prompt that lingered in my mind for the hour drive back:

What do I know that I keep ignoring?

And I've realized that it's this:

My work was first selfishly for me. To save myself. To figure out how to be a woman in today’s world asked to hold it all and know it all and be it all. How to keep the career I loved while having a chance to be the mama I could feel myself yearning to be.

This quest has taken me from my girls starting elementary school through the wilds of Covid and then a move across countries to now starting middle school. 

It was never really about just building a company or conquering a market need. It was about seeing the impossibilities and somehow making this funny math work - take one person - give them two jobs, no tools and raise the stakes.... and see what happens.

What happens is that we burn out, and our relationships start fraying and the joy leaches out of something that, at its core - parenthood, is the ultimate joy and purpose.

Lost in the dunes of the startup desert, in the search for something that can miraculously do all the things for all of the people, I've lost sight of the simplest truth.

It started with the "mother load".... it started with not trying to outsource and distance myself from the work of being a parent but rather to have a chance to have the space to actually be connected to it and the people in my life.

When there's no path in front of you, it's easy to forget why you set out in the first place.

But this week was a good reminder, get back to my why.

And that's chasing these charts - the inequity in black and white.

We're fooling ourselves if we think we're getting to gender equity or the solving the plummeting birth rates if we don't solve for the invisible load of actually having a family today.

But in the end, this is and has always been, about making it make sense for me. Thanks Abby, for the push to remember that.

When I first set out to be an entrepreneur, my mental models were closer to that of building and running a small business, as my parents had done my whole life. Matters of profit margins and cost optimizations and pricing and aggressive but steady growth.

But as I've shifted to high growth start-ups I've learned the questions are different:

- what do you see or believe that no one else does?

- how can you put that insight to work to lasso and drag the future to now, faster?

- where do you believe the points of leverage are?

In hearing Sam talk about GPT5 and doubling down on coding tasks, I'm not surprised. A good number of people in the industry believe that if you can unlock AI agents that can code most effectively, you unleash the most impact - in scientific discovery, in productivity, in more... more.

I believe that todays tools leave a gap - between what the user wants and needs and how the tool works. This gap is the invisible load required by the user to bridge the gap to get utility from the help. 

And I believe the smaller we make that gap - the more we can see it and solve for it, the more relief and space and help it opens up.

My leverage comes from seeing small details and embedding that into scale tools.

But the questions I keep asking myself: what do I believe that no one else does? And how do I use that as leverage?

..if we're bringing back blogs, then I wanted to see what it would be like to share my thoughts via good ol' fashioned vlog....pardon the rambling but hey, maybe that's the point? Messy, not meant for the masses, and true.

If AI in general and ChatGPT specifically were the buzzwords of 2023, then surely the buzzword of 2025 is "agents". Everywhere I turn, efforts to define it, build tools and infrastructure for them, build first approximations of them.

There are so many ideas of how to get to this future of many acting on the behalf of the few. Some like Perplexity, Dia and Yuturi believe they will come from the de facto tool to getting things done: browsers. I can see it: get great at navigating browsers to get things done the way that humans do, on the path to soon doing it on their behalf.

Others believe the future is via AI assisted virtual assistants - taking on whole tasks and projects like booking dentist appointments or ordering groceries with a back and forth. I can see that too - take a task and understand the parameters to do it well and learn.

These are all logical, reasonable approaches. It's just that, if there's one thing I've learned over the past decade it's: humans are anything but rational, predictable creatures.

And while I think it'll be much easier/faster to get to agents on professional domains, especially in well defined areas like coding, legal, medical records etc, I think personal agents are going to come down to understanding the nooks and crannies of how individuals do things. 

There lies so many nuances - some people love the process, others need to start with a shortlist. Some want to feel challenged and others want it to just get done. And it differs task by task, category by category. What a user does with regards to meals might be different with booking travel. Or one partner in a household might want to do meals one way and the other partner another.

So how to even think about personal agents?

For me, it comes down to building something small but broad that can map a set of nooks and crannies... some fundamental space where we've not only built the effective "task path" for the agent to take, but the "trust path" that allows this interaction to ultimately end up in success.

Today, most of the focus is on the task path - what to-dos, what rational set of steps to execute. But without mapping the invisible counterpart, the trust path, there is going to continue to be a fundamental gap that prevents widespread adoption and ultimately, delight.

I've been interested in the concept of "social productivity" for a long time now.

It's the idea that we get things done on the recommendations or advice of trusted others. Think about a friend raving about new gadget or a colleague going on about a new work tool.

But since becoming a parent, this is the one idea I keep coming back to - not just because it feels satisfying, but because it's incredibly practical and necessary. So in the age of AI and "model intelligence", how can we tap into the "collective intelligence" of each other.

1. It's an effective shortcut. There's just too much surface area to cover as a parent to become an expert in all of the things - especially because as soon as you get the hang of a thing, kids grow in the next phase. One of the best hacks for parents is to be friends with a couple families with kids 1-2 years older than your own because they can give you a practical sneak peek on what's coming around the corner. But we know it to be effective for travel or restaurants or books - areas where the options are endless and you need someway to get to a reasonable shortlist.

2. It connect us. We are a social species and a big part of our connections lie in our consumption - of things and experiences. There's a special "zing" of joy attached to learning that someone else loves the things you do - whether it's a book or a journal or fav parenting IG person ... it makes you feel connected to that person and then more open to some of the other recommendations they might have. To this day, when I see a Vanity Fair magazine, I'm taken back to my days at Starbucks HQ when a friend raved about reading it religiously. 

3. We can model information and areas current models aren't great at. Today's foundation models are largely trained on the public internet. And that we know, is already poorly represented by women and the work of our homes (eg. beyond reddit or recipe blogs)... plus much of the wisdom in our families and communities isn't best represented in words but in actions or rituals or tacit knowledge. So I think it's vital we have ways to tap into those stores of wisdom in simple ways.

Which leads me to the thought that there is such an emphasis on advancing model intelligence but what of making it easier to tap into our collective intelligence?

It used to be that we'd gather each week at church or at the playground or at the one extracurricular activity everyone's kids did. Plus there were only so many options people were aware of, in the age before infinite info at your fingertips. That reality is well and gone but what's the modern version that doesn't just let our lived experiences languish?

In the age of infinite info, it's the filter that matters and especially for parents, it's critical to have a trusted filter to navigate the endless questions. 

So what does unlocking collective intelligence look like?

Still. The only way around is play.  

I don't know if I'll ever become a Runner. But I'm feeling joy that for now, I've found a way just to be a runner.

I have a terrible attention span. I'm like the dog, Dug, in Up - there are so many squirrels in this world. So many things capture my attention - science and languages and people and food and...

It worked well for my career while I had great managers who can see when I was getting bored and moved me into new and challenging roles. But soon I ended up at companies where I wasn't so fortunately and my reach was constantly constrained in corporate boxes.

So I left and found founder-dom. Only I realized through my first "start-up" that just having an idea and a product aren't enough to either succeed or keep my attention.

For that I needed obsession. And obsession would come in the most unlikely (to me anyway) of places - parenthood. 

Now I could focus on one piece of the puzzle endlessly. Jiggle it unless it gave. Move it around until it clicks satisfyingly into place.

And the key? Small things, done consistently.

Showing up everyday to tackle the most urgent thing in front of me. The one piece, that if figured out, would allow me to move on to the next challenge.

But without unlocking that piece? I would look up and see all the others in front of. I panic. I feel overwhelmed. I don't know what the point is.

And instead, I look back down to the piece I do have. 

Tomorrow I show up to do the same.

And whether it's a startup or working my way up to running 10K, it's the only way I know to tame my great love story with the vastness of this world.

Little by little.

The single most powerful idea I've learned as a founder over the past decade:

The future is not a forgone conclusion.

MLK Jr's powerful "The arc of the moral universe is long, but it bends toward justice" or Sam Altman's belief that his kids will grow up to be vastly more capable because of AI are both powerful beacons of possibility, but they are not inevitabilities. 

Better happens because people notice and care to make it happen. They dig in and make it their mission. Innovation and invention is an incredibly powerful force of change and good in the world. An addictive one. I think that's why the longer I'm a founder, the longer I find it hard to imagine I can be anything else.

But the reality is that broad ideas exist in the world as specific implementations. And the real magic happens when many people with vastly different circumstances build from their specific viewpoints of justice and ease and capability and delight. 

So I feel this urgency is building inside of me, along with the excitement.... there is so much of the world that is going to open up with this foundational technology - actually solving for uneven labor in the home, being incredible thought partners, making educational access and equity possible.....

But none of these are forgone conclusions. They're simply possibilities. 

And the thing about possibilities is that they need people to pull them out of the ether and start building them into reality here, on the ground. 

But who is going to do that? Today, most of the building and defining of AI is happening with a shockingly small number of people who share a very small set of backgrounds and defining views.

So we need to build builders. 

People who can move through the world confident, capable and equipped with what they need to to be the change they want to see in the world - regardless of where they come from, what they look like or who they know.

The future is not inevitable. But nor is it to be left to a few to design and build.

I think the greatest abundance will happen when each of us feel empowered to use these tools to build the futures each of us dream of.

Life feels so complicated now. Like with every day that passes somehow I manage to pull tighter some invisible thread that binds all of my days and decisions together. 

Reading my words from when I was 25 I realize it's all relative. I'm sure even then I thought my life was full and complicated. But miss the certainty, the naivety held in those sentences.  Like I could just write what was happening in my world and hit post and there was nothing else to it. 

It doesn't feel easy to do that anymore. Sure some of it's all of the demands on my time, but more, it's having the space to think to even know what or how I'm feeling before I can share it with anyone else.

I just did a TED talk. Me. I've wanted to do that for so long and then I've been working on it so hard and now? I'm back and hurled back into the everyday but I need time to reflect. That's really what the writing always did for me.

I find myself looking for space more and more. 

Space to breathe, space to think, space to be. 

But what comes out for that space to come in?

I am a lot. Like certifiably. I want too much. I demand too much. I need too much.

I’ve known this all my life. Its served me well as I’ve just set my eyes on new challenges and hurled myself at them with focus and tenacity. 

But it’s hard with my people. I think I can be a hard person to live with. To be with. So uncompromising and stingy with the grace.

So it’s been a revelation to find myself married for 15 years. To have found someone who’s not afraid of the messy. Of the too much. Who gives an anchor to my wings.

It’s in the hardest times that we realize what it is that we actually have and in the turmoil of the past year I’ve realized just what a gift I have in the sturdiness of him.

Someone who doesn’t shy away from the hard, uncomfortable work. Who can take my frustrations and come back with optimism and a plan. 

Who has never walked away from my too much. 

In the 18 years we’ve been together we’ve been through a lot. Some years more shouty than others. We are two very different people coming from two very different backgrounds. 

But if there’s one lesson marriage has taught me it’s this:

There is no inevitability. No forgone conclusions. There is only waking up every single morning and deciding to do the work. To fight. 

So yeah, I marvel on days when I make it really hard to want to fight for this. I am in awe of the strength and the sense of self it needs to keep showing up. To keep pushing at me, but also, keep pushing with me.

True partnership is really hard. It pushes us to the brink as often as it feels rewarding.

Running two companies, raising two kids, keeping a sense of our own selves while holding onto and nurturing our relationship - so many days the math of all that feels crushing. 

Our wedding rings are engraved with:

In dreams and in love…

… there are no impossibilities.

It’s in the hardest days I feel those words the most.

I first started a new fangled thing called "blogging" when I first moved to Cincinnati. I wanted a simple way to tell my friends and family about what was happening in my life, even if I didn't talk to them daily.

It was easy. Jot down what was only mind and hit publish. My friends would occasionally check in whenever they were curious.  

My own little weird corner of the internet where I could share unfiltered all the things I was experiencing and learning and thinking and my people could drop by and visit, when and however long they wanted to.

It felt both connecting and therapeutic. There were no sweeping assertions or conclusions. There was little insight and often no real "point".

It was just life in its most beautiful and honest form.

Eventually I moved to Typepad and Wordpress and then Substack. And what had started as a small personal thing found broader resonance as I shared about building a company while building a family. 

But as I shifted from a blogging platform to newsletter one, I found my writing changed. I wouldn't have thought it, because the newsletter offered better, easier distribution and yet. 

I felt this pressure to make my posts mean something if it was going to show up in your inbox. So then I would hoard my thoughts, start weighing and considering them. Seeing if they were "worthy" enough.  And too often? I felt they weren't. So I found myself writing less and filtering more. 

Recently I went back to my old blogs. As I read those confident, naive and raw posts I realized: I missed blogging. Just straight up, inconsequential, unfiltered little posts. That live on my little weird page. Where others are welcome but if they find it's not for them are welcome to never come back.

I shared this in a new little writing group and found resonance amongst other onetime bloggers.

So we're bringing back blogging. Even if it's just a handful of us with our weird little ideas and raw experiences. Digital places to express and be ourselves for no other purpose than just to be.