Hi, I'm Zach. Follow me on twitter.

When Private Beta Isn’t

2 Apr 2013

What happens when your private beta get’s a little less…private? We’ll see, but so far - your users send praise, the gatekeepers send questions, and you find all the weird bugs that would have taken you weeks to see otherwise. Not so bad so far…


Note: If you come across Connect4Square, it’s in PRIVATE BETA. If you happen to be rebellious and sign up anyway, do send us any comments/thoughts on the app.

Dancing with Dinosaurs

2 Apr 2013
This is a draft post I’m writing for a startup blog. I’d love feedback…

We live in a technology world dominated by ‘lean startups’, ‘fast failures’, and ‘minimum viable products’. It’s a consumer-driven landscape that puts a premium on launching quickly and iterating on user feedback. A valid approach, to be sure, but not all businesses have these luxuries. Especially in the B2B world, startups are often working in stodgy old industries that have significant barriers to entry.

So what happens when the business you decide to build runs into gatekeepers and incumbents? When we launched Plaid a year ago, we set out to revolutionize the finance industry. One of the biggest barriers to creating innovative finance applications is that the transaction data and data processing infrastructure is 30 years old. We’re building a set of infrastructure tools to fix this - and that means dealing with a lot of gatekeepers. For us, it’s banks and credit card issuers - the epitome of a tech dinosaur.

Startups aren’t in the business of waiting, but often times that’s what dealing with incumbents requires. That said, there are definite ways to add value and speed up the decision-making process. In our case - we made it very simple for banks and card issuers to say yes. First, we built an innovative and robust technology platform that required banks to do absolutely no work. Then we sold it - we got applications to integrate our tools and built a userbase that was begging for access to their banking data. All the banks had to do was give the go-ahead - and they did just that.

Building revolutionary companies often means you’re working in industries that have had very little historical innovation - and that often means gatekeepers, incumbents, and regulations. With these barriers though, comes the opportunity to have a huge impact and build game-changing technologies where they are needed most. With the right mix of determination and innovation, it’s these industries dominated by dinosaurs that can be the most rewarding.

Free Radicals

28 Feb 2013

Every now and again, someone I know goes through a startup job search process. When this person is particularly impressive (and a particularly good friend), they can be of incredible value. They have a constant reason to be meeting with people, learning about their businesses - and if they are very often effective in making new friends & connections. On two such occasions in the past six months, friends who were job searching have helped me with new clients and/or high-value connections. Now when friends ask for advice on finding their next gig, it’s exciting - and these are meetings I always want to take.

The Anatomy of a Card Transaction

18 Dec 2012

The term ‘processor’ is often used loosely when referring to card-linked transactions, and can reference most players in the value chain. Here I’ve attempted to explain a bit

The Players

(0) Customer and Merchant (not discussed)
(1) Merchant Point of Sale (POS)
(2) Payment Gateway
(3) Payment Processor
(4) Network/Association/Interchange
(5) Card Issuer (Customer Bank/Acquirer)
(6) Merchant Bank (Merchant Acquirer)

The card payment landscape is difficult to explain - especially so as the large players have moved full-stack over the past 10 years. First Data and WorldPay are traditional processors, but now have strong gateways. Chase is a traditional card issuer, but their Paymentech division is also a gateway & processor. Wells Fargo is also now a processor (and has nabbed Stripe as a client). Visa and MasterCard have also become consumer card issuers. POS and Gateways are often integrated. First Data even makes cards - including the AmEx Centurion.

The Basic Steps for a Transaction

(1) A customer completes a transaction at the merchant POS. POS system then passes the transaction, card, and merchant bank info to the Gateway
(2) The Payment Gateway collects transaction, card, and merchant data from the Gateway and passes it securely to the linked Payment Processor
(3) The Payment Processor collects the Gateway data and identifies the correct Network/Association based on the card type. Processor then routes all the transaction data to the Network.
(4) The Network collects the transaction information and verifies the available balance with the Card Issuer*. In addition to the balance check, the network performs a security check to ensure the card is within normal spending patterns. If the transaction is approved by Card Issuer and passes the security check, the Network passes an affirmative response upstream to the POS and downstream to Card Issuer**. During Settlement***, network collects transaction amount from Card Issuer account and passes it to the Merchant Account.
(5) The Card Issuer is responsible for checking the available balance and passing the verified amount to the Network during settlement
(6) The Merchant Bank receives the value of the transactions less the fees deducted by the Gateway, Processor, and Network.

Player Details

(1) The Merchant POS is the in-store scanner or shopping cart. Often they will help to do the initial collection of payment data. Online examples include Shopify, Magento, Drupal, and Big Platform. The Brick and Mortar POS landscape is dominated by NCR, IBM, HP, and Verifone - and Square is quickly emerging. For the most part, merchants hold an ‘Approved Merchant Account (Token)’ however many e-commerce platforms are now providing this as a service. Fees are usually based on a monthly fixed cost, a per-transaction fee, and an overall percent of transaction fee. Generally the POS (or sometimes Gateway) charges the merchant a single fee that covers all the downstream costs.
(2) The payment gateway is a secure connection between a POS and Processor. Historically, processor connections required such high security that it was not economical for a POS or merchant to implement themselves. Of late, these costs have come down and we now see the integration of POS, Gateways, and Processors. Examples of e-commerce gateways include Authorize.net, Paypal, Stripe, and Braintree. Verisign, CICS (IBM), and Authorize.net are the dominant in-store players. 
(3) Payment Processors are responsible for collecting and routing data from the gateway to the Network. The correct Network for each transaction is identified based on the first and last card numbers (did you know 10 of the 16 card numbers are non-unique and not considered personally identifiable information?). The biggest players in processing are First Data and TSYS, followed by WorldPay, Chase Paymentech, and Wells Fargo.
(4) The Networks (or Associations or Interchanges) do the real work. They interface with the Processors to collect transaction, customer, and merchant info; the Card Issuers to authorize purchases and collect payments; and Merchant Banks to pass settled payments. As such, they have the highest fees. Visa, MasterCard, American Express, and Discover are the largest Networks.
(5) The Card Issuers are the consumer-facing element of the equation - they issue consumer cards, collect monthly payments, and handle customer service. While they rarely charge a transaction fee, they make money from consumer lending, annual fees, and late fees. The largest US issuers are American Express*, Discover*, Chase, Citi, Bank of America, Wells Fargo, and Capital One.
(6) The Merchant Bank simply accepts transactions and deals with disputes (but that is a different post).


*The Network and Card Issuer are a single entity in the case of American Express and Discover. This is called a ‘Closed-Loop’ transaction. Transactions that use the Visa or MC Networks are considered ‘Open Loop’.
**In (4), once the transaction is approved, an affirmative message is passed via the Network, Processor, and Gateway to the Merchant POS. If a transaction is declined, a similar message is passed and the POS after which the entire process is severed and no settlement occurs.
***Settlement (as referenced here) is actually a three-step process. First is Authorization, where a customer is approved for a purchase. Second is Capture, which occurs when the merchant passes a batch of authorized transactions to the Network (often each night). Third is Settlement, when the captured transactions are actually pulled from customer accounts and moved to merchant accounts. Those $0.07 charges that appear in your ‘pending transactions’ are the authorization charges - they are subsequently cancelled and replaced once the final transaction amount has been captured.

Gmail App: Designed by Committee

17 Dec 2012

Somehow, nobody has made a functional iPhone email application yet. iOS Mail was hopeless, Sparrow was close (now dying a slow death), Gmail 1.0 was worthless.

I was excited about Gmail 2.0 - push notifications, email alias support, a pretty new interface, and support for some powerful features (undo send, etc.). After using it for an hour, it replaced sparrow on my home screen. 

Unfortunately, I jumped the gun. With more use, it feels like a bunch of pretty pieces stitched together with no overall thought to UX. The archive button half-overlaps the star so removing emails from the inbox becomes an exercise in precise tapping. There’s no way to switch recipients easily - moving from to/cc/bcc requires manually typing in a full email address. The address book sync is slow - so much so that it often freezes when typing a name. And then the small annoyances - it doesn’t port your signature, doesn’t auto-load messages to the app (even though it sends notifications), settings are tough to manage.

But it was fast, and it worked so I was ready to over look all these…

Then it happened. Double-send. On an email that went to all my investors.

Then again the next day on an email to my co-founder. And I started getting double-sends from friends and advisors who also used the app. Somehow there have been few public complaints about this bug (though you wouldn’t notice you’re double-sending unless you cc’ed yourself).

Ah well, here’s to waiting for mailbox

Update: Apparently this is a known issue.

Large Patriarch

6 Nov 2012

A medeval version of Notorious BIG’s ‘Big Poppa’:

To all the wenches in the tavern with aesthetics and elegance,
Please allowest me to intertwine these dactylic cleaning mechanisms in your netherregions.
Who harmony creates and speaks innuendically with all the trollops?
The rear of the tavern imbibing upon port is where you may encounter my presence.
The rear of the tavern, wooing wenches with a plethora of apprentices flanking.
Many inquires I make, fine herbs I imbue, lute songs I enjoy,
But oh Zeus, I cannot retire.
For one of the trollops I must enchant.
Fornicate with, yet tallest nobody, whyfore?
Why cause questions of my morality for such a lighthearted ruckus.
I haveth much greater execution than Craig, and in the hay-filled sack,
Trust, wench. I haveth the power to create bread and fish for the beggars.
One needeth not hoard, for I have a plethora of acquaintances with chariots.
Pence and shillings, true men of wealth.
Climbeth aboard my steed with me, inviteth your friends to board their chariots
For I haveth herbs a-plenty.

I enjoyest when thou callest me Large Patriarch.
Elevate your hands if thouest enjoyeth victorious game-playing.


To all the ladies in the place with style and grace
Allow me to lace these lyrical douches in your bushes
Who rock grooves and make moves with all the mommies?
The back of the club sipping Moet is where you’ll find me
The back of the club, macking hoes, my crew’s behind me
Mad question asking, blunt passing, music blasting
But I just can’t quit
Cause one of these honies Biggie gots to creep with
Sleep with, keep the ep a secret, why not?
Why blow up my spot cause we both got hot?
Now check it: I got more mack than Craig and in the bed
Believe me sweetie, I got enough to feed the needy
No need to be greedy, I got mad friends with Benzes
C-notes by the layers, true fucking players
Jump in the Rover and come over, tell your friends jump in the GS3
I got the chronic by the tree

I love it when you call me big pop-pa
Throw your hands in the air, if you’s a true player

Louis CK prior to SNL on 11/3

3 Nov 2012

Hello. Its louis here. I’m clacking this to you on my phone in my dressing room here at studio 8H, right in 30 rockefeller center, in Manhattan, new york city, new york, america, world, current snapshot of all existence everywhere.

Tonight I’m hosting Saturday Night Live, something I zero ever in my life saw happening to me. And yet here it is completely most probably happening (I mean, ANYTHING could NOT happen. So we’ll see).

I’ve been working here all week with the cast, crew, producers and writers of SNL, and with Lorne Michaels. Such a great and talented group of people.

And here we are in the middle of New York City, which was just slammed by a hurricane, leaving behind so much trouble, so much difficulty and trauma, which everyone here is still dealing with every day.

Last night we shot some pre-tape segments in greenwich Village, which was pitch black dark for blocks and blocks, as it has been for a week now.

Its pretty impossible to describe walking through these city streets in total darkness. It can’t even be called a trip through time, because as long as new york has lived, its been lit. By electricity, gas lamps, candlelight, kerosene. But this was pitch black, street after street, corner round corner. And for me, the village being the very place that made me into a comedian and a man, to walk through the heart of it and feel like, in a way, it was dead. I can’t tell you how that felt. And you also had a palpable sense that inside each dark window was a family or a student or an artist or an old woman living alone, just being int he dark and waiting for the day to come back. Like we were all having one big sleep over, but not so much fun as that.

This is how a lot of the city is still. I know people in queens, brooklyn, Staten Island, new jersey, all over, are not normal yet. And not normal is hard.

And here at 30 rock, these folks are working so hard this week. There are kids in the studio every day, because members of the crew and staff had to bring them to work. Many people are sharing lodging. Everyone is tired. But there’s this feeling here that we’ve got to put on a great show. I’m sure it feels like that here every week. But wow. I feel really lucky to be sharing this time with these particular good folks here at SNL.

In about 5 hours we’ll be going on the air. I’ll do a monologue. And we’ll show you some sketches that we wrote and try to make you laugh. I’m gonna look really dumb in some of this stuff. But I don’t care. Its awfully worth it. And I’m really excited.

Anyway. I just wanted to let you know. If you watch the show tonight, when Don Pardo says my name and you see me walking out, all the shit in this email is what ill be thinking. I’m a pretty lucky guy. I hope you enjoy the show.


Louis C.K.

Live. From new york. Its saturday night

One short a hundred conundrums

3 Nov 2012

A medieval translation of Jay-Z’s 99 Problems.

If thou’st presented with female conundrums, I doth not envieth thou child.
For I have one less a hundred conundrums, though a wench be not one.
I haveth the sherrif’s men searching for my quivers bows,
Foes who desireth my final rest occurs in a sealed tomb.
The bard critiques enumerate me as ‘Galleons, Pence, Trollops’.
Yet I’m from the Shire (lunatic). From whence do those assertions stem?
If thou was’t reared with perforations in thou’st turnshoes,
Thou rejoyeces’t near the moment thou procures’t many sovereign.
Dismiss the naysayers, for thou can’st kiss the entirety of my netherregions.
If thou not enjoyes’t my bardly musings, thou may increseth the speed by which time passes until the fin.
They at the music box haves’t pause with me if I neglect their engagements,
Yet they nary include my cansons, and thus I cares’t not.
The recanters ascribe to utilize my tanned hindquarters,
Such that shopkeeps may purchase more advertisements. Fornicators!
I knowes’t not how they percevies’t my persona,
Nor comprehend the intellectual prow ice that I haveth.
For I hath grown from burlap to satin, fellows. I am not a serf!
I haveth one less a hundred conundrums, though a wench be not one. Attack me!


If you’re having girl problems I feel bad for you, son
I’ve got 99 problems, but a bitch ain’t one

I’ve got the Rap Patrol on the gat patrol
Foes that wanna make sure my casket’s closed
Rap critics that say he’s “Money, Cash, Hoes”
I’m from the hood stupid, what type of facts are those?
If you grew up with holes in your zapatos
You’d celebrate the minute you was having dough
I’m like fuck critics, you can kiss my whole asshole
If you don’t like my lyrics, you can press fast forward
Got beef with radio if I don’t play they show
They don’t play my hits, well I don’t give a shit, so
Rap mags try and use my black ass
So advertisers can give em more cash for ads, fuckers!
I don’t know what you take me as
Or understand the intelligence that Jay-Z has
I’m from rags to riches, niggas I ain’t dumb
I got 99 problems, but a bitch ain’t one, hit me!

Don’t Punk Out and Quit

19 Sep 2012

From Ben Horowitz:

As CEO, there will be many times when you feel like quitting. I have seen CEOs try to cope with the stress by drinking heavily, checking out, and even quitting. In each case, the CEO has a marvelous rationalization why it was OK for him to punk out or quit, but none them will ever be great CEOs. Great CEOs face the pain. They deal with the sleepless nights, the cold sweat, and what my friend the great Alfred Chuang (legendary founder and CEO of BEA Systems) calls “the torture.” Whenever I meet a successful CEO, I ask them how they did it. Mediocre CEOs point to their brilliant strategic moves or their intuitive business sense or a variety of other self-congratulatory explanations. The great CEOs tend to be remarkably consistent in their answers. They all say: “I didn’t quit.”

A longer version is here.

Passwords and Simplicity

11 Sep 2012

"You do not need a password if you do not log out. Only ask for things you need."
-Diego Zambrano, Bondsy

The complexity of signing up for many mobile apps astounds me - I noticed again today trying out Kuapay. It required my ‘Name as it Appears on Card’, email, password (with a capital and number), email click through authentication, pin creation, and pin input before I got to the application. All that, and I still had to enter my credit card information before I could use it. 

In this case, Kulpay is a mobile payments app - so I appreciate the security - but the overall signup process is incredibly difficult. This seems to be the case for more apps I’ve seen of late - trading perceived security (because it is only that) for signup flow. I wonder what will win long-term: I suspect simplicity.