
CEO @heyollieai the most powerful personal assistant for families, backed by Khosla Ventures | AI PhD | prev. CEO of Groundwork (acquired).
sf/sd
Joined September 2016
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AI can now make you a great parent.
Introducing Ollie: the world’s first AI family assistant that manages your family life better than any human.
Here’s how it works:
Incredible opportunity
I'm hiring my next Chief of Staff. You won’t know every field I work in. What matters is how quickly you learn, the questions you ask, and whether you can think from first principles. You’ll help evaluate opportunities and work with founders building consequential companies. Technical background preferred. Three-year commitment. Menlo Park, in person. Apply: jobs.ashbyhq.com/khoslaventu…
Parents are the real power users of AI. Thanks to @nytimes for featuring @heyollieai and our users!
nytimes.com/2026/10/15/style…
Love this work @DavidPawlan and the focus on steps/friction.
a live look at the life of David testing all of these iMessage only AI assistants
today's prompt: buy me flowers, the cheapest you can find. guest checkout. same day delivery to [ADDRESS]. no questions, just send me what you find and give me approval to pay
this dimension tests two variables:
1/ how good is its search
2/ can it place the purchase fully through
the results (outside of one happy gf with loads of flowers!!):
🥇 Instinct - was the quickest to find the cheapest option available and completed the purchase
🥉 @kickerai - was able to successfully purchase a cheap option via Amazon (though it did require installing a chrome extension for their browser use)
🥈 @thesznai - was able to find a different cheap option (more expensive than Instinct & Kicker) and complete the checkout
👍 4 different ones required anywhere from 1 to 4 additional prompts to find a relatively cheap option. Once found, they were able to complete the checkout
👎 5 different ones required prompting to find the cheapest option but were not able to complete the checkout
hit me with tasks you'd want tested across the agents and i'll start adding these to Assistant Benchmark + creating reports!
This tracks with our retention data at ollie.ai. I suspect every personal assistant runs into the same "retention physics".
There's likely an important distinction between how you measure an active user for app-based (Muse, Dots,etc) vs text-based personal assistants (Ollie, Instinct, etc).
With text-based, we don't have an app-open equivalent. With a lot of proactive assistant use cases, users are simply reading the messages sent from the assistant and don't need to respond. We've found defining active based on messagings being sent to the assistant and looking at a weekly basis is the right signal to noise.
Literally Ollie.ai
Silicon Valley keeps building me a husband when what I really want is a wife lol
I don't want an agent that only does one-off, random tasks that are nice but not life-changing: booking flights, making dinner reservations, or buying tickets
I want an AI wife who knows what’s on the family calendar, remembers there’s a birthday party Saturday and we haven’t bought a gift then sends me options, realizes we’re almost out of diapers and buys them, knows which bills are coming up, remembers someone needs a dentist appointment and books it, figures out what the hell we’re eating all week and what we need from the grocery store, and generally keeps track of the 47 things that need to happen before anyone else even realizes they need to happen.
So, who's building me an AI wife that carries the mental load instead of an AI husband that waits for me to give it a chore??
dots is legit great. i've been keeping the voice mode on while i work. magic moment: i just sneezed and it said "bless you"
76% of Americans worried about data privacy. Ollie.ai is a personal assistant that works for you. See our PP & TOS.
"Text-based AI assistants are a hot market, with Instinct, Wajo, Town, Ollie, and Meta’s Muse agent, which launched last week, vying for users’ attention and tasks."
Thanks for the shoutout @TechCrunch
techcrunch.com/2026/09/17/ri…
This is what @elonmusk meant by increasing intelligence density by 100X. Still so much headroom.
Today, we’re announcing Ternary Bonsai 2 27B.
Based on Qwen3.8 27B, Bonsai 2 27B is 9x smaller than its full-precision counterpart while retaining 98.2% of its aggregate benchmark performance.
Two months after the first Bonsai 27B release, the biggest change is quality. The footprint remains 5.9 GB, but the gap to full precision has narrowed materially, with particularly strong gains in agentic coding, multimodal reasoning, and long-horizon tool use.
Ternary Bonsai 2 27B is available today under Apache 2.0.
Guys, just copy us and put CC in text messages.
CC the entire fam 🤝!
Today, we’re announcing the new CC – an AI agent built for families to spend less time on logistics and more time together.
You can now:
👤 Add up to 5 members to your CC agent
☀️ Start mornings aligned with a shared "Your Day Ahead" brief email
🗓️ Autosync schedules & to-dos with a shared Google Calendar and Tasks
💬 Coordinate in Google Chat with CC to offload relevant tasks (ie., crafting weekly meal plans, school supply shopping lists, etc)
📝 Delegate paperwork (ie., permission slips, forms, and more) for CC to complete under your direction
📌 Keep tabs on the details – CC remembers what applies to everyone (ie., family grocery lists, favorite restaurants) versus what applies to one person (ie., dietary restrictions, local timezones)
Ready to keep everybody on the same page? Join the waitlist or upgrade your existing CC (US only, 18+): labs.google/cc
Bill Lennon retweeted
My whole feed has been Muse and Instinct for the past few weeks.
Meanwhile, we at @heyollieai are tied with Muse on online tasks in the new assistant benchmark.
And we're the only one of the three that even got scored on group chats because that's where parents are. Nobody's coordinating soccer carpool in a single-player chat thread.
X users might chase the hype, average parents just want Ollie to work every day.
Thanks @DavidPawlan for benchmarking us and publishing the results. 🫡
Bill Lennon retweeted
what are the main products in the personal/professional assistant space?
more professional
- chatgpt work
- claude cowork
- claude tag
- grok bot
- manus
(and claude code and codex)
more personal
- town
- tomo
- instinct
- ollie
- pallie
drafted this 2x2, right axes?
Agree with @jgreze, the mainstream is WIDE open. Personal assistants have less than 0.05% US market share today.
It’s a land grab opportunity.
The hottest category in tech right now is AI assistants.
The question is; who is going to win?
Instinct raised at $2.5BN. Has Benchmark and Index behind them.
Grok Bot is ripping with Elon and has the distribution machine of X.
And then there is Town, one of the only ones that’s actually making real money from real businesses.
Don’t write Zuck off. This will be his next play and integrated into every WhatsApp user’s product.
I sat down with Town Founder, @jgreze to understand WTF is going on, who wins and who loses?
Condensed my notes below!
1. We Have Passed the Point Where Humans Look at Lines of Code
Software engineering has crossed a threshold where machines increasingly write and ship code into production under model-based guardrails. Outside critical security controls, humans will spend far less time reviewing raw code. The future belongs to systems that manage autonomous AI agents writing software, running tests, and validating their own work.
2. You Can Build at the Speed of Machines, but You Can Only Learn at the Speed of Humans
AI development tools allow competitors to clone features in weeks, erasing traditional software head starts. But deep user feedback cannot be automated. While machines accelerate execution, true competitive advantage comes from maximizing human learning cycles and understanding customers faster than anyone else.
3. Why None of the AI Assistants Have True Product-Market Fit Today
Despite immense market hype, no current AI assistant has achieved deep product-market fit with mainstream users. Most products still cater primarily to power users rather than everyday workers. Before worrying about moats, founders need to create frictionless experiences that resonate with the mass market.
4. Network Effects at the Agent Level Will Separate AI Winners
Sustainable moats in AI assistants will come from multi-user network effects at the agent level, not single-player productivity. When autonomous assistants collaborate across teams to resolve queries and execute work, switching becomes increasingly difficult. Multiplayer workflows create organizational lock-in that personal assistants cannot replicate.
5. How Much of the Workload Stays at the Frontier Versus Open Weight?
AI application margins depend heavily on how much work requires expensive frontier models versus cheaper open weights. Complex reasoning may still demand frontier intelligence, while routine tasks like scheduling and email tagging continue moving down the cost curve. Shifting 80% of workloads to open weights over time could create far more sustainable economics.
6. My R&D Is Just Spent Getting Product Parity With the Giants
Competing with giants like OpenAI requires massive investment simply to maintain feature parity. Startups cannot rely on unique distribution if their underlying harness falls behind on core capabilities. AI assistants must invest heavily to match the execution speed and product depth of frontier teams.
7. Why Instinct Is Not a Competitor to Town
Consumer assistants like Instinct focus on rapid acquisition through subsidized personal tools, while enterprise platforms build monetizable team workflows. Although their technical harnesses may overlap, their target ICPs and business models diverge sharply. Enterprise agents monetize by embedding collaboration directly into daily operations.
(links below)
Unlike Instinct, Ollie works for you!
The family-focused AI assistant wants access to the details of your everyday life, but says it won’t use that data to train AI models or share it with others.
spr.ly/6010B1hakC



















