The Power of Small Steps:
How a billionaire overcame his greatest setback – and what we can learn from it for our daily habits
— Just a Dude Who Invests (@DudeWhoInvests) January 7, 2026
There are moments in life that call everything into question. Moments when the ground gives way beneath your feet and the way back seems impossible. For Bill Ackman – one of the most successful and at the same time most controversial hedge fund managers of our time – that moment came in 2016. His fund Pershing Square had just lost 4 billion dollars on a single investment. His 25-year marriage fell apart. The man who had set out to be a millionaire by 30, worth a hundred million by 40, and a billionaire by 50 stood before the ruins of his ambitions.
What he discovered in this crisis was not some complicated investment strategy or a brilliant financial trick. It was a simple principle he ironically knew from his own world: compound interest. Only he didn't apply it to his portfolio – he applied it to his life.
Who Is Bill Ackman?
William Albert Ackman was born on May 11, 1966, in Chappaqua, New York. His father Lawrence was a real estate investor and laid the foundation for Bill's interest in the world of finance early on. The family has Ashkenazi Jewish roots – his grandfather, born in what is now Ukraine, emigrated on foot to Austria-Hungary in the 1890s, where he trained as a tailor.
At Harvard University, Ackman first studied history and graduated magna cum laude in 1988. One book would fundamentally change his path in life: Benjamin Graham's "The Intelligent Investor," the bible of value investing. After his MBA at Harvard Business School in 1992, he founded the investment firm Gotham Partners with a fellow student.
In 2004, Pershing Square Capital Management emerged from 54 million dollars in seed capital – today one of the best-known activist hedge funds in the world, with over 18 billion dollars in assets under management. Ackman's investment philosophy is clear: he invests only in companies with a strong moat, companies that will exist practically forever and whose competitors face high barriers to entry.
The Art of Failing
What sets Ackman apart from many other investors is his willingness to speak publicly about his defeats. And there were quite a few: the bet against Herbalife cost him a billion dollars. The investment in Valeant Pharmaceuticals wiped out 4 billion.
In a talk at the Citadel Finance Speaker Series, he said:
These words are not resignation. They are an invitation to resilience.
The Principle of Daily Compounding
In the midst of his deepest crisis – the fund was down 35%, investors were pulling their capital, his private life lay in pieces – Ackman discovered a method that changed his life. He began applying the principle of compound interest to his personal development.
The basic idea is strikingly simple: if you make just 0.1% progress every day, it sounds like nothing. But annualized? That's an enormous change. Ackman describes his approach like this:
For the first few weeks, he noticed no significant changes. But that is precisely the nature of compounding: the curve starts flat and then virtually explodes. After about 90 days, he began to see real changes.
Why the Concept Is So Powerful
Compound interest has not been called the "eighth wonder of the world" for nothing. In the financial world, its power is obvious: if you invest 10,000 dollars at a 10% annual return, you'll have over 600,000 dollars after 43 years. At a 15% return, it would be over 4 million.
But the principle applies far beyond the world of finance. Ackman often points to Warren Buffett: "When Warren Buffett was 50 years old, he had not yet earned 99.5% of his current wealth." The message is clear: compounding rewards patience, resilience, and the discipline to keep going.
The crucial point: it's not about making a giant leap every day. It's about getting a little better every day. Learning a little more. Building a small habit. Taking a step forward, even when the road seems long.
The Science Behind Small Steps
What Ackman discovered intuitively has long been confirmed by behavioral psychology. James Clear, author of the bestseller "Atomic Habits," does the math: if you get just 1% better every day, after one year you are 37 times better than at the start. Conversely, a daily decline of 1% means practically zero after a year.
Neuroscience supports this approach as well. Our brain forms neural pathways through repetition – the more often we do something, the stronger these connections become. That is biological compound interest: every repetition makes the next one easier. BJ Fogg of Stanford University calls this "automaticity" – the moment when an action is so deeply anchored that it happens without conscious effort.
Interestingly, research also shows that the size of the action matters less than its regularity. A daily 5-minute walk takes root faster than a weekly 60-minute workout. The reason: the brain responds to frequency, not intensity.
The challenge is that our brain is bad at understanding exponential growth. We think linearly. We expect progress to be immediately visible. And when it isn't, we give up.
This is exactly why so many New Year's resolutions fail. People expect dramatic changes within a few weeks – and when they don't materialize, they lose motivation. The secret lies in enduring the "valley phase" before the compounding curve turns steeply upward.
How Ackman Puts His Principle into Practice
Ackman's daily routines are remarkably down-to-earth for a billionaire:
Focus instead of diversification: Unlike many investors, Ackman relies on a few well-thought-out positions. Pershing Square typically holds only about nine stocks. This concentration allows deep understanding and full attention.
Long-term thinking: Ackman is not interested in what a stock will be worth tomorrow or in a month. He thinks in decades. "I look at what an investment will be worth in 10, 15, 20 years."
Unemotional decisions: "I'm a very unemotional person when it comes to investments. The best thing you can do when everyone is running in one direction is to go the other way."
Training resilience: Ackman has learned to accept setbacks as part of the process. His philosophy: the question is not whether you fall, but how you get back up.
Ackman's Greatest Successes: Compounding in Practice
To understand how powerfully compounding works in reality, it's worth looking at some of Ackman's most successful investments.
The COVID-19 hedge: In March 2020, Ackman recognized earlier than most that the pandemic would shake the markets. He bought credit protection worth 27 million dollars – and turned it into 2.6 billion dollars in less than a month. A spectacular gain, but one that was only possible because Ackman had sharpened his understanding of markets and risks over decades. Here too: compounding of knowledge and experience.
General Growth Properties: During the 2008 financial crisis, Ackman bought shares in this bankrupt real estate company for pennies. Through active engagement, he helped restructure the company. The investment multiplied many times over.
Chipotle Mexican Grill: Ackman recognized that the restaurant chain was undervalued after an E. coli scandal. He invested heavily and helped management restructure the company. The stock price recovered spectacularly.
What all these successes have in common: they were based on deep understanding built up over years. Ackman doesn't gamble – he bets on companies he knows inside out and holds on, even when the market disagrees in the short term.
What We Can Learn from Ackman's Defeats
Just as instructive as his successes are Ackman's failures. With Herbalife, he underestimated the emotionality of the market and the power of an opponent like Carl Icahn. With Valeant, he placed too much trust in a management that crossed ethical lines.
But this is where the core of the compounding idea shows itself: defeats only count if we learn nothing from them. Ackman analyzed every mistake meticulously and adjusted his strategies. After Valeant, he publicly swore off taking seats on company boards, since it clouded his judgment. That is compounding in its purest form: every mistake becomes a lesson that improves future decisions.
The Universal Application
The beauty of Ackman's approach is its universal applicability. Whether you're trying to get fitter, learn a new skill, build a company, or have better relationships – the principle remains the same. Ackman himself says:
His advice for such situations: don't look back at where you were. That only discourages you. Focus on the next step.
Daily Compounding and Yeap: The Perfect Match
The concept of daily compounding is built directly into Yeap's DNA. Yeap is not designed to push you toward radical changes. It's about building small, daily habits that add up to massive changes over time.
Every habit streak in Yeap is visible compounding. Day 1 feels small. Day 10 starts to feel meaningful. Day 100? That's real transformation.
Yeap's core principles mirror Ackman's philosophy:
Small, doable steps: Yeap doesn't push you toward 90-minute workouts when you're just starting out. It's about beginning with 5 minutes – and staying consistent.
Focus on consistency, not perfection: It's not about being perfect every day. It's about showing up every day.
Visual progress: Yeap makes your compounding visible. You see your streaks grow, your habits solidify, your life change – one day at a time.
Long-term thinking: Just as Ackman does with investments, Yeap encourages a long-term view of habits. It's not about changing everything in a week. It's about being a different person in a year.
Practical Implementation: How to Start Today
Based on Ackman's principles and the Yeap philosophy, here are concrete steps for your own daily compounding:
- Choose one habit: Not five. One. Concentrate your energy the way Ackman concentrates his portfolio.
- Make it ridiculously small: Want to read? Start with one page a day. Meditate? Two minutes. Exercise? Five push-ups. The point is to set the bar so low that you can't say no.
- Track every day: What gets measured gets improved. Use Yeap to make your daily compounding visible.
- Don't look back: If you miss a day, don't sink into guilt. As Ackman says: "Don't look at where you came from. That only discourages you."
- Trust the process: The first 30 days won't feel world-changing. That's normal. The magic happens in the months that follow.
The Bigger Picture
Bill Ackman is back on top today. His wealth has almost doubled. He is happily married to MIT professor Neri Oxman. Pershing Square is delivering strong returns again.
But more important than the financial figures is the lesson he took from his darkest time: compounding works. Not just with money. With everything.
As a signatory of the Giving Pledge, Ackman has committed to donating more than half of his wealth to charitable causes. His foundation has already given over 750 million dollars to more than 100 organizations. Here too: compounding in action. Small contributions, over time, become massive impact.
The One Step That Changes Everything
Ackman reminds us that the biggest mistake is not failing. The biggest mistake is giving up. Not continuing. Not taking the next small step.
"Make a little progress every day, and it works every time," he says.
Not sometimes. Not usually. Every time.
That is the power of daily compounding. And with Yeap, you have the perfect tool to put it into practice in your life.
The next step is waiting. Take it.
Sources: Forbes, Fortune, The Acquirer's Multiple, Citadel Finance Speaker Series, Lex Fridman Podcast
About Yeap: Yeap is your personal habit tracker, built on the principle of daily compounding. Start today with one small habit and experience how small steps add up to big changes.
Sounds like your pattern? In Yeap you can see what your days have in common.
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