In his story The Mystery of Marie Rogêt, Edgar Allan Poe wrote

“Experience has shown, and a true philosophy will always show, that a vast, perhaps the larger, portion of truth arises from the seemingly irrelevant.”

And it is in that spirit that I lend another perspective, voice, and beating heart in the hope of unearthing some more truth around payment technology.

While it may seem like we in the tech world don’t share much with a 19th century poet, I’d like to tell you a story.

In 1843, Edgar Allan Poe’s story The Gold Bug was published, which ended being the most popular and lucrative work he released during his lifetime.

Most of you have likely never heard of it. You’re probably familiar with The Raven or The Tell Tale Heart, but probably not The Gold Bug.

However, it was this story that won him a whopping $100 at the time ($100 being the equivalent of a little over $3000 today), which was the total winnings from a short story contest held by The Dollar Paper, a Philadelphia-based publication of the day.

Edgar Allan Poe was actually was one of the first American authors to actually attempt to make a living purely through writing and as the headline of this blogpost indicates, he wasn’t very good at it.

Unfortunately, Poe was the son of two actors. His father abandoned the family not long after Poe was born and his mother tragically died when he was just about a year old. An orphan, he was taken in by a wealthy merchant one John Allan who had young Edgar Poe baptized Edgar Allan Poe.

While a student at the University of Virginia, Poe repeatedly gambled away money meant for tuition and school supplies and eventually dropped out. This lead to him becoming estranged from his foster father Mr. Allan. Additional quarrels with Allan — who was rich and extremely adulterous— lead Poe to be disowned by Allan and excluded from the will.

So no trust fund. No parents or foster parents to fall back on. Poe had just a pen, a vivid imagination, and dogged persistence.

So The Tell Tale Heart was published before The Gold Bug in January of 1943 and Poe was reportedly paid $10 for it.

His poem The Raven published in 1845 came on the heels of The Gold Bug’s success. However Poe was paid only $9 for it.
It was The Gold-Bug that drew standing room-only crowds to Poe’s lectures and  gained him fans across the globe in places as France, Russia, and Japan.

In fact , he was actually paid twice for the story. First $52 by Graham’s Magazine a periodical for which he served as an editor but then he heard about the Dollar Paper’s contest and withdrew the piece from Graham’s — notably never returning that initial $52 to Mr. Graham, mind you.

I don’t begrudge you if you’ve never heard of The Gold Bug. To be honest, I’d never heard of it either before I sat down to write this talk. Having read it,  I can’t necessarily recommend as it is to— put it bluntly–kinda racist. Without excusing racism, I do think the kernel of this story and Poe’s story more generally is useful in illustrating a central point I’d like to make.

THE STORY

In The Gold-Bug, an unnamed narrator travels to meet with an old friend, one William Legrand, who lives on an island near Charleston, South Carolina. Legrand is sort of an eccentric prodigal son type who is full of endless fanciful sort of get rich quick schemes.

So when our narrator arrives, LeGrand and his companion, a freed yet still in servitude black man called Jupiter explain, that while wandering through the woods they came across a live beetle that they believe was somehow made of solid gold.

Our narrator listens politely to the story and then slowly heads back home to Charleston never actually laying eyes on this gold bug since Legrand had curiously lent it out to a friend.

A month later Jupiter comes to the door of our narrator and beckons him to return to the island. LeGrand who is now sweatier and wild eyed than ever informs him that as it turns out on this excursion where they’d come across the bug they also come across a scrap of paper connected to Spanish treasure hidden by one long dead pirate Captain Kidd. With that paper, LeGrand had been able to decipher the location back out in the woods where they’d be able to get their hands on the loot.

A month later Jupiter comes to the door of our narrator and beckons him to return to the island. LeGrand who is now sweatier and wild eyed than ever informs him that as it turns out on this excursion where they’d come across the bug they also come across a scrap of paper connected to Spanish treasure hidden by one long dead pirate called Captain Kidd.

With that paper, LeGrand had been able to decipher the location back out in the woods where they’d be able to get their hands on the loot.

LeGrand says to our narrator

“This bug is to make my fortune to reinstate me in my family possessions. Is it any wonder, then, that I prize it? Since Fortune has thought fit to bestow it upon me, I have only to use it properly and I shall arrive at the gold of which it is the index. ”

After some cajoling LeGrand convinces Jupiter and our narrator to head back out into the woods to a particular tree. From there the instructions are very specific, they have to tie the gold bug to a string, climb up the tree, dangle the gold bug on a string through first the right eye lobe then the left lobe of a skull nailed to a branch at the top of the tree. Then Jupiter — who is doing all the work here — is to drop the bug and X marks the spot where they have to dig.

The narrator at this point relates a certain amount of doubt to us saying something we in the startup field likely all can relate to:

So after quite a bit of digging and shouting and napping and more digging they actually finally obtain the coveted treasure. When they’ve dragged it back to the shack, LeGrand explains to Jupiter and our dear narrator that he hadn’t been crazy after all that month. Instead it turns out he’d been wound up in an elaborate cypher which required quite a bit of code cracking and Sherlock Holmes style detective work.

In the end, Jupiter and our narrator are fascinated, and from what I could tell highly relieved that their friend had finally gotten he was looking for and would hopefully stop dragging them into the woods at night.

Now LeGrand with his righteous indignation about being due his fortune in life is surely just a thinly veiled version of Poe. And in some ways, Poe is himself not so different from us in the startup field.

Much like Poe, founders have a vision and some positive indicators from the market and people seem enthusiastic about what they are doing. But how do they get the fortune they believe is their due?

In Poe’s day he wrote on spec and the hope that he might win a contest or a small contract that he could go collect on.These days, tech founders throw together a pitch deck and a website and then try to set up a simple system for people to add their credit card and pay them.

So I shared this story with you because I think Poe’s life and work offers a few key lessons for the modern startup.

ITERATION

The first lesson is around iteration….

Edgar Allan Poe is known as the father of modern horror and also the father of science fiction and also the father of cosmology and cryptography.

Nearly 600 words or phrases were coined by Poe. Some words we still use today, like bugaboo and finicky and multicolor.

This wasn’t simply because he was a creative and divinely inspired human being. He was scrambling for relevance and money. He was iterating and aiming to please.

In 1839, four years before the publication of The Gold-Bug, Poe published an article in Alexander’s Weekly Messenger where he challenged the readers to send him coded messages to decipher. He received hundreds of messages so he knew the interest and audience was there for this kind of thing and that’s what lead him to write The Gold Bug.

Poe wanted what we all want which is to deliver to customers and be paid for it. He was an artist to be sure but he was intensely concerned about being an entertainer and reaching what today we might call Product Market Fit.

So as Vice President of Customer Success at Clubhouse Software, I help customers find their way around and begin to master our product and I also oversee our customer support team. Support is responsible for being responsive to those customers, and support is also the frontline for fielding any payments problems.

I don’t know how many of you are old enough to remember this but in the 80s there was a commercial for a brand of hair products called Vidal Sassoon. Their tagline is “if you don’t look good, we don’t look good”.

The idea there is that your appearance and success in using their products was a direct reflection on them, and this is true in all manner of customer facing work. regardless of how chaotic or seemingly in flux the company is, the role of success and support is to make the company and product look pulled together and sleek.

We want our customers not only to choose us but to feel encouraged by their choice, both in the product they receive and also in the ways they interact with our company. As such, no matter how the product may we change we need the user experience to feel consistent from initial marketing touch straight through to payment.

In a recent whiteboarding exercise, my colleague in customer success worked with one of our engineers to devise what would be the “ideal invoice”, working backwards from a list of customer complaints about our confusing existing invoice. This is frustrating.
The invoice should just work, so we can work on providing a great experience to the customer.

When we can’t decipher mysterious bank codes but the customer insists their form of payment is valid, we don’t look so good.When we struggle to make refunds or rerun invoices or when we have to read through convoluted logs to understand the how and why of a user’s billing history, we can start to lose customer confidence.

Our payment system needs to look good or else our product and our company start to look downright bad in the eyes of the customer.

INNOVATION

The second area after iteration where I think Poe can shed some light is in the area of innovation.

Poe’s Gold Bug arrived on the scene at a challenging but exciting time in this country.

The American economy had just rebounded from the Panic of 1837 a five-year depression that many believe was caused by Andrew Jackson’s policies against the banks. At times during that depression, things got so bad that people were giving out this thing called a “Hard Times token” in lieu of pennies.

Sojourner Truth’s “Aint I A Woman” speech commemorated