Rising From The Ashes
Each month at The Fountain, we’re going to introduce themes.
This month it’s Getting Out Alive.
Not thriving. Not scaling. Not winning. Just surviving the stretch long enough to learn from it, adjust, and keep moving.
This theme came directly out of recent conversations around failure, forced pivots, stalled momentum, and the quiet realization that many of the most important seasons in life and business are not the ones you tell stories about later.
They are the ones you endure. This week is our favourite stories of entrepreneurs you know, about when they didn’t think they were going to get out alive, and as a bonus a great conversation with David Macdonald, a senior economist who is in favour of a wealth tax.
We continue to grow each week, and we are grateful because this community has always been about honesty over highlight reels. If you feel that someone in your circle would benefit from these conversations, here is a share button (one of our subscribers just earned a 1-1 with Ria and I for referring 20 people!).
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Most successes are close to dying than you think.
Almost Dying
The stories we tend to repeat about success usually begin once the outcome feels secure. By that point, the danger has already passed, and the uncertainty has been replaced by clarity.
What is rarely examined are the moments just before that, when things could still fall apart and often nearly do.
The stories from entrepreneurs you likely know and some of them we look up to are a reminder of how narrow that margin can be.
Almost dying has a way of stripping away excess interpretation and leaving behind only what matters.
That sense of proximity is important, because many of the successfull people we now think of as inevitable were once operating within the same thin margin, where survival was not assumed and outcomes were still fragile.
Failure Is Not the End of the Story
Jensen Huang once took a five million dollar contract from Sega to build a gaming console and failed to deliver what was promised. Under most circumstances, that would have closed the door. Instead, he returned to Sega and asked them to convert the contract into an investment, knowing that without it, the company would not continue.
At that moment, Nvidia was not on the verge of becoming a defining company in the world. It was on the verge of disappearing.
Howard Schultz faced a quieter version of the same pressure. Starbucks was struggling, and people close to him questioned whether continuing made sense. His father-in-law urged him to find stable work, while his wife, pregnant at the time, carried a salaried role to support the household as the company tried to survive.
He talks about importance of support, something we’ll dive into next week.
Pivoting and just keep trying
SpaceX reached a point where there was enough capital for a single remaining launch. If it failed, the company would close. There was no buffer and no extended runway to correct course afterward. Everything depended on one final execution.
Airbnb’s path was different, but equally precarious. The company adjusted repeatedly, changing assumptions and direction as it tried to find a version of the idea that could survive. Each pivot was a response to pressure rather than a declaration of strategy.
What these situations share is not creativity for its own sake, but responsiveness. Pivoting happens when the original structure no longer holds and continuing forward requires abandoning certainty. It is less about reinvention and more about staying aligned with reality as it shifts.
It’s never “Too Late”
The founder of Home Depot had already been fired from another retail business before starting what would become one of the most successful companies in the category. He was by conventional standards old to start a business.
Colonel Sanders was in his sixties (Yes 60s) when he started KFC.
These stories matter because they disrupt the assumption that timing follows a predictable arc. Experience accumulates even when results do not immediately show it, and proximity to failure often sharpens judgment rather than diminishing it.
Arriving later does not mean arriving unprepared. In many cases, it means arriving with a clearer sense of what does not work and why. Some of the most durable outcomes are built by people who have already tested their limits and lived through the consequences.
Closing Thought
When viewed from a distance, success stories appear inevitable.
Many of the most successful entrepreneurs were operating inches from nothing at critical moments, making decisions under pressure with limited options and no guarantees. Their stories were not decided by avoiding failure, but by surviving it long enough to adapt.
This month at The Fountain is about paying attention to those moments. The ones where survival precedes success, and where the outcome remains undecided longer than we like to admit.
If you are at the end of the runway, you’re not dead yet.
TAKEAWAYS AND TACTICS
1. Buy time before you chase clarity
Jensen Huang didn’t fix Nvidia’s product before fixing its survival. He converted a failed Sega contract into an investment because time was the real constraint. When survival is at risk, extend the runway first. Time creates options, and options create second chances.
2. Ask for help that changes the structure
Emotional support matters, but it doesn’t keep companies alive. Structural support does. Income coverage, renegotiated terms, deferred obligations, reframed deals. Identify who can materially change the shape of your situation and have the uncomfortable conversation early.
3. Pivot in response to reality, not ego
Airbnb didn’t pivot to be creative. It pivoted to stay alive. Each adjustment was a response to pressure as assumptions broke down. Pivoting is not reinvention, it is alignment with what reality is actually allowing.
4. Strip the operation down to what buys survival
Near-failure has a clarifying effect if you let it. Excess interpretation becomes dangerous. Cut anything that doesn’t extend runway, generate learning, or move you closer to revenue. Most companies don’t die from bad ideas, they die from carrying too much weight when the margin disappears.
5. Respect time, it cannot be rushed
Home Depot and KFC were not early stories. Their founders arrived later, sharper, and more prepared. You can’t make a baby in under nine months. Some outcomes only arrive if you survive long enough for experience to compound.
A conversation with David Macdonald - Senior Economist For Alternative Policy
As many of you know we’ve been writing a series called “Eat The Rich”. A three part series on Wealth Taxes. Check out part one, two or three if you haven’t already.
The Debate on Wealth, Taxes, and Incentives
In a wide-ranging conversation, The Fountain sat down with David Macdonald, Senior Economist at the Canadian Centre for Policy Alternatives, to unpack one of the most charged economic questions in Canada today: fairness, taxation, and whether wealth taxes actually work.
At the core of the discussion was a philosophical divide, and it was filled with hilarious facial expressions on both sides.
David argued that equality doesn’t mean treating everyone the same. People start from different positions, with different opportunities and setbacks, and public systems like healthcare, education, and infrastructure require funding.
Canada’s progressive tax system reflects this idea by asking those with higher incomes to contribute a higher share, while the bottom third of income earners pay no federal income tax due to credits.
From there, the conversation moved into wealth taxes. David outlined two proposals from his recent research: a new top “millionaires” income tax bracket and a modest annual wealth tax applied only to very high net worth individuals.
His view is that Canada doesn’t have a spending problem so much as a revenue problem, and that wealth inequality has grown far faster than income inequality, largely driven by executive compensation and asset growth. (Which we disagree with agree with)
The counterpoint focused on incentives, competitiveness, and capital flight. The concern was less about whether inequality exists and more about whether wealth taxes actually solve structural deficits, or whether they risk driving entrepreneurs, investment, and talent elsewhere.
Examples from Europe, California, and U.S. states with no income tax were raised to question whether higher taxes ultimately shrink the tax base rather than grow it.
David pushed back on the idea that higher taxes automatically reduce investment. He pointed to the 1990s in Canada, when higher capital gains taxes coincided with strong investment and economic growth, arguing that companies invest when opportunities are good, not simply when taxes are lower.
The conversation closed on CEO pay, the original spark for the discussion. David highlighted that the explosion in CEO compensation is driven less by salaries and more by bonuses, which often remain insulated from poor performance. Even during downturns like the pandemic, many companies retroactively adjusted bonus formulas or relied on government support to keep executive pay whole, widening the gap between CEOs and workers.
What emerged wasn’t consensus, but something more valuable: a real debate about incentives, fairness, and the long-term health of Canada’s economy. A reminder that these questions don’t have simple answers, and that how we design systems matters just as much as what we fund.
Thanks again David for the conversation.
What do you think about his main points? Reply and let us know as we get to the bottom of wealth taxes. When you watch the video, ignore the filibuster watch past the first 5 mins.
Does Canada have a spending problem?
Is wealth taxes targeted at property a form of seizure?
Are CEOs overpaid?
Is a wealth tax actually going to work when it hasn’t historically worked anywhere else?
Thanks everyone for staying with us as we experiment with new content. Talk soon, Trent and Ria.
