Ask Olive
Ask Olive was an agent for the worst day in a house: a flooded basement, a tree through the fence, a storm on the way. You call or text Olive and it tells you what to do first, what to buy, who to call, and what your insurance covers.
2024 · At tCR · With Jenny Cox · 2 years agoAsk Olive came from the same idea as Self Settle: when people are at their most stressed, they need one clear next step, not a website. Floods were the place to start. Flooding does $58.4 billion of property damage in the US every year, every state has had flash flooding in the last five years, and 40% of flood insurance claims between 2015 and 2019 came from outside high-risk areas. An inch of water can do $25,000 of damage, and most homeowners policies do not cover it.
Olive helps people prepare for and recover from climate disasters. It does three things: preparedness advice built on climate trends and live weather; safety-first guidance in the moment, with the right products and local pros; and plain help with insurance, meaning what is covered, how to file, and what to do when it is not.
Just text Olive
Nobody downloads an app while their basement fills with water. So Olive lived where people already are: a phone number. You call or text, say what is happening in your own words, and Olive works out how bad it is and what comes first.
Every conversation builds a running guide for that incident: what to do right now, a shopping list sized to the water you actually have, local pros if you want help or a second opinion, and what to fix before next time. Ask it which wet vac to buy and it answers with three from the hardware store down the road.
The claim starts in the same thread. Send photos and video of the damage and Olive starts the incident report for your insurer.
A calm brand for a bad day
Olive green, cream and one drop of water. The type sits in speech bubbles, because the product is a conversation. The launch work went where people already go when the water comes in: their feeds, searching for help.
Before the wave
We prototyped the agent on Vertex in early 2024, before the tools were ready for it. We pitched it around and had real interest. It was just the two of us, Jenny and me, and we chose not to go forward: the investment terms on offer in that market were not ones we wanted. An agent you just talk to, that does the legwork for you, is everywhere now.
Product and strategy by Jenny Cox ↗









Ask Olive
Ask Olive was an agent for the worst day in a house: a flooded basement, a tree through the fence, a storm on the way. You call or text Olive and it tells you what to do first, what to buy, who to call, and what your insurance covers.
2024 · At tCR · With Jenny Cox · 2 years ago
Ask Olive came from the same idea as Self Settle: when people are at their most stressed, they need one clear next step, not a website. Floods were the place to start. Flooding does $58.4 billion of property damage in the US every year, every state has had flash flooding in the last five years, and 40% of flood insurance claims between 2015 and 2019 came from outside high-risk areas. An inch of water can do $25,000 of damage, and most homeowners policies do not cover it.
Olive helps people prepare for and recover from climate disasters. It does three things: preparedness advice built on climate trends and live weather; safety-first guidance in the moment, with the right products and local pros; and plain help with insurance, meaning what is covered, how to file, and what to do when it is not.

Just text Olive
Nobody downloads an app while their basement fills with water. So Olive lived where people already are: a phone number. You call or text, say what is happening in your own words, and Olive works out how bad it is and what comes first.

Every conversation builds a running guide for that incident: what to do right now, a shopping list sized to the water you actually have, local pros if you want help or a second opinion, and what to fix before next time. Ask it which wet vac to buy and it answers with three from the hardware store down the road.
The claim starts in the same thread. Send photos and video of the damage and Olive starts the incident report for your insurer.

A calm brand for a bad day
Olive green, cream and one drop of water. The type sits in speech bubbles, because the product is a conversation. The launch work went where people already go when the water comes in: their feeds, searching for help.

Before the wave
We prototyped the agent on Vertex in early 2024, before the tools were ready for it. We pitched it around and had real interest. It was just the two of us, Jenny and me, and we chose not to go forward: the investment terms on offer in that market were not ones we wanted. An agent you just talk to, that does the legwork for you, is everywhere now.




Product and strategy by Jenny Cox ↗