Matt LeBel Security & personal finance for startup employees

Preparing for the worst 💀

Over the past several years, I’ve picked up some high-risk activities: private aviation, late-night Getaround rentals, startups (😉), etc. I’m also climbing Mt. Kilimanjaro in September. It seems safe to say that my absolute risk % of death relative to my age is above average.

Though a bit morbid, it’s my personal preference to think through this worst case scenario and prepare items of personal importance, financial accounts, and digital data for distribution.

I’ve been iterating on the core strategy and backups since the beginning of the year. Here’s what I’ve landed upon so far:


Creation of a legal will and living will (health care directive)

Having put this off for several months, I was excited to see a completely free service from a company in the latest batch of YC swoop in to solve this problem.

It’s early days for the startup, but they’ve made the process dead simple, with each step providing helpful context + tooltip text around the available decisions.

Screenshot of the Willing app dashboard

There’s one point of up-sell inquiring of interest to prepay for funeral expenses (I declined), but it’s friendly, unobtrusive, and easy to dismiss.

Finalizing the will and health care directive documents is as simple as grabbing a couple of co-workers (they must be unnamed as beneficiaries in the docs) to serve as witnesses and collecting their signatures and addresses.

Have some stock options floating around? Make sure to include assignment of any applicable stock options in your will (assuming you’d like them to be gifted to a specific person). Most startup stock option agreements allow for an extension beyond the standard three months / 90-day termination exercise window in case of termination via death or disability (usually 12 months).

Beneficiaries named for financial accounts

A quick process, but one that requires tracking down SSNs for your those who you’d like to name as beneficiaries.

Financial account summary printouts

In an effort to make accessing assets in various financial accounts easier for my named beneficiaries, I’ve printed out and collated account details from all financial institutions where I hold accounts and placed them in a safe deposit box controlled by the executor of my legal will.

Digital account backup & access

Some companies, including Facebook, do a great job of allowing you to name a “legacy contact,” or someone to manage your account after you pass away.

Several companies from this generation have the potential to store lifelong data (Evernote, Dropbox, etc.) on a large number of people, and I suspect that many introduce similar “legacy contact” implementations in the coming years.

A screenshot of Facebook's trusted contact form

Details and credentials for the rest of my digital accounts are stored in my 1Password vault.

In order to help my family and friends access accounts on my behalf, I keep an encrypted backup of my 1Password vault (updated roughly once per quarter) on two, identical USB drives along with a PDF document with instructions for decoding the master password in a safety deposit box controlled by the executor of my legal will.

In the future, I plan to geographically distribute an additional copy of my encrypted vault and password decoding doc elsewhere in the US and give control of that safety deposit box to the backup executor of my legal will.

Here’s a template to create a decoding doc of your own if you’d like to follow a similar strategy:

Digital accounts - master password

Decoding should only occur upon my death or long-term incapacitation.

Entering this decoded password into my 1Password vault will allow for access to all other digital accounts. If an account has two-factor authorization enabled, the one-time override passwords are stored as secure notes in the vault.

Devices with access to my 1Password vault include:

* Device 1
* Device 2
* Device 3

Should you need help with the decryption or gaining access to these accounts, please contact:

Tech savvy contact #1: [phone number]
Tech savvy contact #2: [phone number]

Password details:

* Full password is [n] characters in length
* [additional details]

Phrase one:
* [security phrase answer]

Number string one:
* [security number string answer]

Phrase two:
* [security phrase answer]

Number string two:
* [security number string answer]

Number string three:
* [security number string answer]

Digital writing backup and distribution plan

If I’m no longer around, I’d love for my recorded thoughts to be shared with those that I felt closest to. For the past five years, I’ve written candidly and extensively in Evernote.

Every couple of months, I download a dump of all the raw HTML and .enex (their proprietary data format) versions of notes I’ve created and update the data across eight USB drives that I keep in a safety deposit box under my control (the executor of my legal will is named as the beneficiary for contents of this box). Though each of these drives is intended for a specific person, the content on each is identical.


And that’s it!

Maintenance of this strategy takes about two hours per quarter and allows me to rest easy knowing that my personal, digital, and financial assets have a good shot of finding their way into the right hands should I become a statistic or decide to suddenly go off the grid and move to Switzerland.

-Widerluege!