The Angel and the Devil

The first $1M of startup fundraising, in angel investment or seed capital, has a job. The job of the funding depends on when you raise it.

"When the time arrives, stop thinking and take action", said Napoleon Bonaparte

The angel investor of fertility, brimming with confidence and charisma, went on top of the inspiration hill that Spring and announced: “we need to make investments in water ways; for water is life for this village, and thirst is coming!”

There was a murmur in the crowd of one hundred people, contemplating with fascination this visionary's foreshadowing of this curious “thirst”, as he called it. Men drank generously from their water bottles. And expecting mothers, pointing out each others' baby bumps, adjourned the meeting with hope and laughter. There were just two determined men that day, nodding at each other[1]. They had quit their employments in anticipation of this moment; and they knew exactly what this meant. They had much less than nine months left.

That’s how Leap O'Faith and Scrappy Uncertain, two old time friends, went into the startup water business.

Leap O’Faith believed in accelerating the work. “Look, Scrappy! Dire thirst is coming. Have you looked at those pregnant bellies?!” he said with wide eyes of excitement, “You won’t dig the pipeline from the lake in half a year working alone. We need seed investment. I’ll take as much as I can get. The opportunity is now or never!”

That same week he put together a business plan outlining the channel through which the village’s pipeline was to be laid out from the lake. He climbed to the top of the hill and met the angel investor. “My name is Leap,” he said, “and I have secured the word of the elders of the village behind me, supporting the man who will water this village.” The angel looked at the vein of ambition and passion popping out in Leap’s neck as he was describing his devotion to his people. He looked at the plan and the letters of intent from the elders. “You have courage and faith!” proclaimed the angel, and sat on the chair, writing a seed investment check for five startup employees’ salaries against his knee, handing it to Leap O'Faith.

That same week Leap hired himself as a CEO, landed one skilled geologist as a CTO, and recruited three professional diggers as employees. They set out to dig a stream from the lake exactly wide enough to fully water the village in six months, when those pregnant couples were sure to come begging.

Scrappy Uncertain didn’t have Leap’s level of certainty, so they never partnered. He came from a long life of startup failures and missteps, so he couldn’t bring himself to make promises to the well-intentioned angel investor. “On what basis am I to secure someone else’s confidence, when I’m not sure what I’m doing myself?” he wondered. Everyday of that week, he went to the base of the angel’s hill, then turned around. He wasn’t certain enough.

The next morning Scrappy sold all his personal belongings and bought the fanciest little shovel he could afford. He started digging from the same lake that Leap and his team were digging from. But instead of doing the digging wide and properly, he dabbled with an inch-wide stream. In the evening, old Leap came over, and pitied him with laughter. “You should come join my startup team man,” said he, giggling at the tiny ambitions of his small-minded friend.

Whatever faith Scrappy had in himself now washed away, like the water trickling down his narrow stream.

The best laid plans of mice and men

Three months later, Leap had completed half of the channel. His arms-wide water way had made the distance half-way to the village, with proper scaffolding, architecture and design. Scrappy on the other hand had only an inch-wide stream zigzagging haphazardly through the landscape — but he had hacked that tiny narrow pass all the way to the front yard of the elders. He knocked on their doors. “I’ve brought water, a penny a glass, who’s thirsty?” he asked.

The elders came out and took a look. “Son, that’s not clear drinking water you’ve got there, that’s mud water!” His heart sank again. “How do I fix this?” "Go to the local shop and buy a filter", they replied, “it’s expensive, but it will refine it.” So he did. The next day he knocked, “I’ve brought clear water, a dollar a glass, who’s thirsty?” he asked.

“That’s too expensive! We already have enough water coming from the well for cheaper,” they replied, “Is it plain old water?" So Scrappy left, did some thinking and showed up the next day, with some color and sugar added to the water: “I’ve got this delicious magic drink that makes you happier and quenches thirst. Two dollars a bottle. Who’s thirsty?”

The sales started trickling in. One or two a day the first week, two or three the next. People were getting a taste for this strangely refined sugar drink. Growth was meager, but compounded weekly.

Scrappy started reinvesting the dollars and the story behind them. He recruited a friend’s time and effort to double the width of the inch-wide stream by giving him some cash and a decent share of the business to get him excited. Whenever the friend became too keen to widen a bottleneck to a foot, Scrappy would become strangely alert, “No! I’m uncertain about needing a foot-wide channel. Two-inches wide is plenty. Don’t work harder than you have to, You Ain’t Gonna Need It !"

A few weeks later, Scrappy went to the hill to meet the angel investor. He was nervous, awkward and sweaty. “Hello Sir!” he said, "I know you probably get these requests all the time, but I have a thirsty village to satisfy and a dedicated friend to employ. We spent everything I had on that shovel, and I’m too exhausted to smile at the customers. I wish you would help us carry this burden.”

“I’m so sorry Mr. Uncertain, I’ve already made an investment in the water business,” said the Angel Investor of fertility, “and besides, O’Faith's much wider channel is almost at your front step. The elders better love you, if you want to last.”

In the ninth month, Leap O'Faith, who had suffered several accidents with the collapsing walls of his much wider channel, finally completed the project. The water was flowing thick and strong in his channel, all the way to the elders’ door. So they stood there, babies in hand: “Son, what you have here is mud water! The other poor fella already invented a drink that muddy at two dollars a pop, but we had to convince him to sell us clear water again, because these babies were born, you see.”

“Huh?!” Leap scratched his head. “The other guy Scrappy,” one elder said, “he has a foot-wide channel now. He sells sugar drinks, and gives clear water away for free! If you want to compete, you’ve got to refine this water to crystal clear, and pay us to drink it.”

Leap walked up to Scrappy’s shack, where he was collapsed under exhaustion and the hope of distant dreams, and rocked the door violently. “You thief!” growled he, with a shriek of indignation, "You STOLE my idea! I asked you to joined me! But you went behind my back and copied everything!” Scrappy was baffled when he opened the door, but he didn’t have a response. He wasn’t good at confrontation; so he let Leap vent for a while. He offered a peace deal, “we’re friends - what if we worked together now?” But Leap slammed the door and stepped outside, “this means war!"

The startup Angel of Death

The filters were expensive, and Leap didn’t have enough funding left from the angel investment to buy enough of them to clear up the mud. Even if he wanted to scale down the operations and fire the entire team, he couldn’t compete with free. Without any returns on the angel’s investment, his attitude and reputation were no longer assets. So he went on top of the hill again: “I’m here to ask for help and advice.”

“I’m sorry son,” said the angel, “the seed I’ve sown in you is late in its blooming. If I had the chance again, I’d invest in your friend, that Scrappy fella who showed up here the other day. At least his water business has some ROI. At this point, the undertaking of filtering that much water is too expensive and out of my hands. You need to go see the devil on top of the mountain.” “Introduce me then,” said O’Faith.

He spent another three months climbing a tall mountain to meet with the devil: “I need a big sum of money to keep my team, bring clean water to my entire village at scale; and possibly export to many villages around it.” The devil smiled, “You have a team?” “I do”, Leap replied. “You have a product, and a market?” “I do”, he replied again. “Will you sell your soul in exchange for this Venture Capital?”

Leap sighed, “I have no other choice.” “Let it be done,” said the devil, and in one signature, took ownership over Leap, his channel, his team and his future. "The money is yours, and your future, mine.”

The angel got a call from the devil that night, “I have purchased Leap’s soul, and in doing so I am relieving you of any obligations towards him. I’m sending your seed investment back, with notable interest. Goodbye.” “I’m sorry to have to wash my hands of him”, thought the angel, as he picked up the phone to call Scrappy. “Hello Scrappy, I’m interested in purchasing a very small part of your business for a lot of money. Let’s see if we can quench the thirst of all these villages.”

Two years later, Scrappy’s water business became so pivotal to the vitality of the growing village that the elders and the rest decided it should be publicly owned. They all put their money together and threw an Initial Public Offering (IPO) party. Every villager became a stock-holder of Scrappy’s foot wide channel, with all its side products. Scrappy remained the Founder CEO.

The devil, seeing the celebrated foot-wide channel from the top of his mountain, came down to the village that year. “Kind elders, oh highly admired board members of there-channel,” he said charmingly, “I have noticed your growing needs for water supplies; and it is with great excitement that I present to you the opportunity to merge and acquire this other arms-wide channel under my influence and control.”

The elders merrily accepted the deal, and paid the devil a premium price for quadrupling their mud water input. Leap O’Faith received a meager bonus, for the price of his soul was already spent in the building of the channel. And he prepared himself to go into the employment of his former friend and new boss, Scrappy Uncertain.

A few years later, Scrappy retired wealthy, and joined the angel as an apprentice seed investment partner. Brimming with confidence and charisma, he went on top of the inspiration hill that Spring and announced: “we need to make investments in entrepreneurship; for validation of premises is the way of prosperity for this village, and a curious generation is coming of age.”

But Mousie, thou art no thy lane,
In proving foresight may be vain:
The best-laid schemes o' mice an' men
Gang aft agley,
An' lea'e us nought but grief an' pain,
For promis'd joy!

Still thou are blest, compared wi' me!
The present only toucheth thee:
But och! I backward cast my e'e,
On prospects drear!
An' forward, tho' I canna see,
I guess an' fear!

Scottish poem by Robert Burns in 1785,
Origin of the idiom “The best laid plans of mice and men often go wrong"


  1. The choice of male characters does not intend sexism. It's parallelism with the Scottish poem at the end of the play.

Amin A.

Written by

Amin Ariana

A software entrepreneur from San Francisco