I signed up to be notified of the BankSimple beta. In return I received a pleasant confirmation email soliciting my banking story.

I'm pretty ashamed of this story, actually. I struggle internally with an idealized vision of how an organized "normal" person manages their finances — the person I should be — and the equally unrealistic desire of what I want to do — which is none of it. I tend towards the ignore and procrastinate mode of coping, so my personal finances are currently in bad shape and it depresses me. So when (future online banking company) BankSimple asks me directly what I want from a bank, my "loves, hates, quibbles, desires, hopes, and dreams regarding your financial life", well, the dam broke and I gave them damn near everything.

I could be replying to a clever bot, or mechanical turk, or an uninterested outsourcer [Update: Rachel is bonafide human. Read her response]. At a minimum it helps to me to share something I'm so ashamed of I avoid even allowing myself to think about, because paradoxically the sharing dispels some of the shame.

There's also the possibility BankSimple will actually read it and at least get a chuckle.

From: Rachel <rachel@banksimple.com>
To: Tim Taylor <tim@tool-man.org>
Date: Wed, 02 Mar 2011 05:22:08 +1100
Subject: Thank You from BankSimple

Hi Tim!

I'm Rachel, a Customer Relations Representative at BankSimple.
Thanks so much for requesting an invitation to try out our
service! We're still planning and testing, but we'll begin
opening up BankSimple soon.

In the meantime, though, I'd love to hear your story. I want to
hear from you, personally, about what you want from a bank:
your loves, hates, quibbles, desires, hopes, and dreams
regarding your financial life. Really: what's on your mind, and
what are you hoping for from BankSimple? We're committed to
building the best service we possibly can, and the only way to
do that is to know what you're looking for. So, what's up?

We can't wait to show you what we've been working on-- and get
your insight into how we can make it better.

Thanks again. Hope to hear from you soon!

Keep up with us on Twitter at @BankSimple
or our blog at http://www.banksimple.com/blog/

Unsubscribe - {an unsubscribe link}

From: Tim Taylor <tim@tool-man.org>
To: Rachel <rachel@banksimple.com>
Date: Wed, 01 Mar 2011 11:45:17 -0500
Subject: Re: Thank You from BankSimple

Hi Rachel,

Thanks for expressing interest in my story. I have a lot of ideas. I apologize for the verbosity that follows.



"Your Honor, it goes to his state of mind"

One time I hired a financial advisor thinking this would help me get a handle on my finances and financial obligations. It was a disaster. Instead of simplifying my life, she just created more opportunities for me to make money, but the net result was more things for me to think about and deal with. I managed in the beginning, but the system eventually broke down completely. This was largely my fault for not (yet) realizing that simplicity was more important to me than maximizing my income or investments. I probably just needed an accountant, not an advisor.

The moral of the story: if it feels like a chore I'll eventually stop doing it. If my financial well being depends on it getting done, then things will go south and I'll be a sad panda just like I am with Chase (checking, Amazon.com Visa) and BoA (mortgage, bleh). If it can't be made simple, then I need to be able to a) automate it or b) outsource it.

Example of Chase and BoA Simplicity Failsauce

Chase and BoA, both of which I've used their online banking, try but fail to make it simple to keep track of where I spend my money. They make an admirable attempt at grouping my expenses into proper categories, but they fail at this enough (categorizing incorrectly or not at all) to make it untrustworthy. I don't want to spend time manually correcting the categorizations if they're not going to learn from my corrections, gradually improving over time. If they could learn, like my Mail.app junk mail filter, then it would be worth my time up front helping it categorize.

(See ginourmous paragraph under Automation for another Chase failwhale)

Shared access

Mah Famileh

My partner Chuck and I have our own accounts. We'd like to keep it this way. But I'd also like the ability for Chuck to access my account without me sharing my username and password. And because BankSimple will be so rockin' awesome and Chuck will have his own account, he'd like to be able to grant access to me to his.

Outsource your life

To help manage my life, I've been considering hiring a virtual private assistant and/or part-time accountant. Once I determine they are trustworthy, I want them to access and use my account on my behalf also without having to divulge my username and password and to be able to disable and revoke (or just revoke) their access when I am done with their services.


I'm notoriously bad at keeping up with my finances. It's like a chore for which I do everything in my power to avoid and procrastinate on. Part of this a character flaw; I'm working on it with my therapist. But partly I recognize that I'll never be that super organized guy WRT banking and personal finance because I just don't want to be that guy. In my eyes, that guy is boring and no fun. So I have to find ways to work around who I'm really going to be; one of those workarounds is automation.

Automatic Payments Saved Me From Myself...

...or at least partially. Things were much worse before I finally ditched the irrational shame of not being able to "hack it" at paying bills on time manually and first took advantage of banking automation.

I learned that getting my bills paid on time meant automatic bill payment. First, I use my credit card for every recurring payment I can. Those which only accept checks, if it's a fixed monthly payment, I use Chase' automatic bill pay. I have no good system for recurring bills with varying amounts which don't allow me to pay via Visa. Such as my electric bill.

I used to authorize my electric company to deduct from my checking directly.  But I got leery of them having such access with having no control or limits, even to the point of having to trust them to stop deducting from my account when I requested it. Solution: Chuck pays the electric bill manually.

I would go back to automatic deductions if:

  • I could generate a new account # just for that payee
  • That account is automatically funded
  • I can set limits on debits
  • I can disable/revoke the account at my leisure

For purchases I use PayPal whenever possible. Failing that, I use my Amazon.com Visa.

So a large portion of bill payment goes on my Visa. Making sure that's always paid off every month is a less than perfect process.

Chase's Automatic Banking Failwhale

And so I also have automatic transfers from Checking to my Visa (xfers since their both Chase accounts). But it's fixed at $400 every 2 weeks, which I once estimated — ala The Price Right — is the closest amount without going over of charges I incur in that time period.

Problem is, I then go and make an impulse buy of the entire Beatles collection on iTunes, and register for some conferences, and buy my husbear some roses. And then I've maxed out my (intentionally low credit limit) because I didn't remember to sign in to online banking and do a 1-time extra transfer of funds (you know, from that 1 account Chase knows about to that other account Chase knows about) and because I refuse to buy their overdraft protection because it's a royal screw job from people who learned the rules of banking last millennia. And then my cell phone bill's automatic payment fails, which triggers AT&T to immediately disable automatic payment in perpetuity, so then I'm also racking up late fees on my mobile bill because my automation house of cards came down from one tiny gust that only existed because my bank thinks I have 2 accounts, whereas I think of it as "my big ball of money with 2 ways to give it to other people depending on which method they accept".

Extra Credit: Public API

I'm a coder. Give me a RESTful API and I'll happily code up some of my own automation without your development team having to suss out exactly what specialized long-tail needs I have. And I'll share it on Github so you can use it, too, in case I'm not the unique and special snowflake I think I am.


I love my Amazon.com Visa. Chase just about ruined it a couple years ago. Here's how it used to work:

  1. Tim earns points by spending with his Amazon.com Visa
  2. Tim's points balance reaches X
  3. Chase or Amazon mails Tim $25 gift certificate
  4. Tim opens mail, signs in to amazon.com, and redeems using unique code printed on dead trees

Then Chase turned it into a generic rewards card. Now I'm earning generic Chase rewards points for Chase's generic rewards catalog which at least still contains the $25 Amazon.com gift cert, but now my rewards process works like this:

  1. Tim earns points by spending with his Amazon.com Visa
  2. Tim has to periodically check if his points balance has reached X, usually he just checks infrequently and then his balance is some uneven multiple of X
  3. Tim logs in to Chase's online banking, clicks around until he remembers how to find the rewards catalog
  4. Tim searches for Amazon.com gift certs amongst all the other rewards he doesn't care about
  5. Tim adds N number of $25 gift certs (because they only come in $25)
  6. Tim check's out
  7. Chase or Amazon mails Tim $25 gift certificate
  8. Tim opens mail, signs in to amazon.com, and redeems using unique code printed on dead trees

Don't offer me a rewards program that's such a pain to use that you are obviously hoping I won't bother redeeming. I'd be happy for a return to the simpler "original" way, but here's how it should work:

  1. Tim links his Visa account to his Amazon.com account
  2. Tim earns points by spending with his Amazon.com Visa
  3. Tim's points balance reaches X
  4. Bank debits X loyalty points, bank tells Amazon.com to credit $25 to Tim's linked account
  5. Amazon.com emails Tim: "Hey, you've earned a $25 reward..."


Why can get my account balances and recent transaction history as an SMS reply (after linking my phone number), but I have to fully sign in to the Chase or BoA iPhone app just to see the same information? The first time using the app, I should be able to authorize/link it to my account. After that, I should be able to see my balances and account history. There's no more exposure there than with the SMS linkage. Maybe I could even deposit a dead-tree check received occasionally. Only when I tried to do transfers, payments, or add/edit stuff should I need to provide my password.

Evernote — or — @BankSimple, You Don't Have to Do Everything Yourselves

I've adopted Evernote as my trusted digital file cabinet. Every month, I'm notified via email that my checking account statement is available. Then I log in to online banking and find the statement — because the email didn't include a direct link, or better yet, the PDF itself. When I click the statement it loads up a clever popup window with the PDF in an iFrame. Then I open the frame in a new tab (finally, this is the PDF!) and I clip this PDF to Evernote. Then, I switch to Evernote and change the "Created" date to match the closing date of the statement and change the title to something meaningful like "Chase Checking Statement" and assign it some tags. Oh, and then I repeat this some other day of the month when I receive my credit card statement.

It would be a dream if I could link my Evernote account and my statements automatically got posted to the notebook of my choosing, created with a reasonably informative title and consistent creation date.

100% Digital (Pipe Dream Mix)

Why do I even need to carry a wallet around? Why should I have cash or plastic when I carry a device (iPhone) which has direct access to my funds. Wave my iPhone across one of those "Blink" transaction pads, pick credit or debit as usual, confirmations, signatures, etc., done. RFID or QR code the pop/snack machine, make my selection in the iPhone app or on the machines website, $$ as bits change hands and clank my Coke or bag of Cheetos is vended to me.

Loaning money to a friend, paying my lawn care guy, donating to the Cub Scout outside Kroger? We should be able to do that by both opening up our app on our PDA/smart phone/portable-digital-device/forever-online-body-implant and I pick an amount, confirm that I'm linked to person across from me (not Joe Blackhat with a Yagi antenna 300m away), and flick the $$ over to them like I'm playing Tiddlywinks.

Never gonna make you cry (Star Trek NG Mix feat. @toolbear74)

Invent the Matter Replicator, a variation on the Transporter technology, thus abolishing the scarcity of physical goods and the basis of wealth. A societal revolution ensues and we boldly go where no person has gone before.


I'm looking forward to any number of these, but especially the Matter Replicator followed by banking that is so easy breezy simple even a slacker like me can appear financially responsible.

Hugs and Kisses,

Read part two of the conversation