Trusty · 2024–2026 · 2 min read
Finding Product-Market Fit, Again
Repositioned Trusty from insurance to estate planning, and landed its first enterprise customer.
The challenge
Most people can't say what they own. When something is lost or stolen, that turns an insurance claim into guesswork and paperwork, and people claim less than they're owed. Trusty gave them one place to record their valuables and sentimental items, with the proof of ownership and paperwork behind each one.
The problem was real, but solving it meant hours of work to prepare for an event people hoped would never happen, so few did it. I joined as employee number one, as I had at Capital Preferences, but this time there was already a product. My job was to find a version of it people would actually use.
The approach
Testing in people's homes
I spoke with potential enterprise clients, and I went into users' homes to help them add their belongings to Trusty, asking about it as we went. The testing pointed to a bigger opportunity than insurance: estate planning.
A reason to do the work
We repositioned Trusty around preparing for your family. Alongside the inventory, people could add estate documents like a will or power of attorney, assign items to next of kin and record video messages. It stopped being a chore for a day you hope never comes and became something people did for the people they love, with insurance as a side benefit.
A plan you can hold
I designed a printed booklet of the whole plan, sold as a paid add-on, and led the engineers who built it on a print-on-demand API. QR codes on its pages open the documents behind them and the videos people recorded, in their own voice. An app is easy to forget, but a beautiful booklet gives a family something real to keep.
AI to do the typing
To cut the effort further, people could photograph an item, and AI cleaned up the photo, pulled out its details and added it to their inventory. Uploaded documents worked the same way. As I left, we were extending it to transcribe the videos people recorded and suggest what else belonged in their plan.
Insight for advisers
The same record shows a financial adviser what a client owns, what they want for their family and the documents behind it, so the advice can be more personal. That made Trusty worth selling to firms, not just families, and advisers now use it with their clients.
The impact
- Supported the founder in raising a $1.5M seed round, with Graphite and Relay in the round.
- Helped land strategic investors, including Purpose Investments.
- One strategic investor became Trusty's first enterprise customer, in Canada.
- Repeated what I did at Capital Preferences: product-market fit, then an enterprise customer, in a new market.