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- If asking twice is bad manners, the greats are unforgivably rude
If asking twice is bad manners, the greats are unforgivably rude
In 1860, The Gentlemen's Book of Etiquette ruled that a refusal, once given, was final.
If you yielded to a request after initially refusing, you too were in breach of etiquette.
For the well-mannered Victorian, "no" meant "no."
Today, gentle reader, we’re lighting that old book on fire.
P.s. More action awaits you in our archives, including what a 60-year study of winners reveals about reaching the top, the personality trait shared by 1381 millionaires, and why when you're launching something new, you need social dandelions.
“No.”
That wasn't the answer Issy Sharp was expecting to hear.
He had just floated what he believed to be a brilliant idea by his friend Cecil Forsyth, an insurance executive at Great-West Life.
Issy had built two apartment buildings in Toronto, and Forsyth had been a major backer for both. Forsyth, a former athlete like Issy, had a soft spot for the young builder who had always delivered what he promised.
So when Issy pitched his friend on funding a new motel, right in the middle of downtown Toronto, he was expecting to see some enthusiasm.
And yet, a firm “no.”
Undeterred, Issy tried his best friend, who'd inherited a fortune. But his money sat in a trust, and the trustee flatly refused to gamble it on a hotel scheme he was sure would fail.
Next he went to Max Tanenbaum, the financier behind half the construction deals in the city, and the one man in Issy's orbit who actually had experience with hotels.
“You're crazy,” Tanenbaum told him. “You know nothing about the hotel business. I do, and I wouldn't touch it with a ten-foot pole.”
Issy couldn't understand it.
A few years earlier, a friend had hired him to build a small roadside motel out by the highway. Issy suggested making the building double the length so the roof could carry an enormous sign that drivers couldn't miss. The place was a hit almost immediately.
If a bare-bones motel could do that well beside a highway, imagine what a good one could do in the heart of a booming city.
Why couldn't anyone else see it?
Every few months, he went back to Forsyth and pitched the project again.
A new site.
“No.”
A new angle.
“No.”
A new reason it might work.
“No.”
This ritual went on for three whole years!
Until finally, Forsyth snapped:
“Stop bothering me. Don't come back until you've arranged to get all the financing you'll need. I'll give you fifty percent if you can get the other fifty.”
It was more of an attempt to get rid of him than an offer to help. Forsyth was confident he'd never hear about the idea from Issy again.
“Can I rely on that?” Issy pressed.
“If you get the other fifty, yes.”
It had taken three years to turn a “no” into a “maybe.”
That was enough.
Issy needed to come up with roughly $750,000.
The first person he went to was Murray Koffler, a pharmacist building a chain of drugstores. Issy had built the rental apartments above one of Koffler's stores, and the two had been trading motel ideas for years. Murray put in $90,000.
The second was Eddie Creed, whose family owned Creeds, one of the most popular clothing stores in Toronto, and who happened to be married to Issy's sister. Eddie had been in on the motel conversations from the start too. Another $90,000.
The third was Issy's father, $90,000 more.
With this momentum, Issy pitched the Bank of Nova Scotia. The Creeds were among the bank's prized accounts, and on the strength of their name, it loaned him $125,000.
He was still short, so his next move was to shrink the bill itself. He went to the tradesmen who would build the motel—men who'd worked his sites for a decade and always been paid on time—and asked them to do the work up front and collect part of their pay only after the doors opened. They agreed. He struck a similar deal on the furniture, spreading the cost over seven years.
Ultimately, every handshake traded on trust Issy had built long before he needed it, and all of it was set in motion by a promise Forsyth never expected to have to keep.
Now that Issy had 50%, he walked back into Forsyth's office and laid it all out.
Forsyth was horrified. He'd expected Issy to raise $750,000 of equity, but every dollar in the stack was borrowed.
Issy didn't flinch. Borrowed or not, fifty percent was fifty percent.
Forsyth went silent for a few seconds.
“All right,” he said. “We'll see if you can do it.”
In 1961, the Four Seasons Motor Hotel opened its doors on a seedy stretch of Jarvis Street that polite Toronto associated with flophouses. Within months it was one of the hottest spots in the city, and it made money beyond anything the partners had projected.
That scrappy motel became the birth of the Four Seasons hotel empire. Today it spans over a hundred hotels across the world, and it's one of the most prestigious names in luxury hospitality. None of it would exist if Issy hadn't continued pushing through that three-year wall of rejection.
And he’s not alone:
Walt Disney spent roughly twenty years asking Pamela Lyndon Travers for the Mary Poppins rights.
The Susan B. Anthony Amendment was introduced in essentially every Congress from 1878 until it passed in 1919.
Churchill cabled Roosevelt for nearly two years asking for destroyers before a fleet finally set sail.
When you need other people to help you get a project off the ground—whether that's an investor, a key hire, or a strategic partner—“no” very often means “not yet.” Not because people are being coy, but because they're evaluating much more than your idea. Forsyth never changed his mind about Issy’s idea. He remained skeptical even as he signed his check.
So what are they all looking for? It depends on the person. Sometimes it's conviction. Do you believe in this enough to keep showing up for years? Sometimes it's force of will. Are you strong enough to smash through the hundred obstacles that stand between an idea and a grand opening? Sometimes it's your ability to listen and learn. Are you coming back sharper each time, or just louder?
Whatever the reason, the uncomfortable part is what this asks of you. Nobody wants to be the person who can't take no for an answer. It feels desperate and it violates every social instinct we have. But when you're asking people to bet on something unproven, being that person is your only option, because sometimes the thing they're really deciding isn't whether your idea is good.
It's whether you are.
Final Calls To Action
Want to understand the implications of recent advances in tech, culture, and product design? If so, Scott Belsky's monthly analysis is essential reading. In his latest June edition, Scott explores why even the smartest companies keep underestimating exponential growth, the rise of “efficient AI”, why “talent density” is overtaking headcount as the metric that matters, and more!
Curious to dive deeper on the story in today's edition? We recommend reading Four Seasons: The Story of a Business Philosophy by Isadore Sharp.
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This edition was written by: Lewis Kallow || (follow) ![]() | With input and inspiration from: Scott Belsky || (follow) ![]() |

