That’s the central lesson of The Art of Execution, a brilliant and surprisingly entertaining book by Lee Freeman-Shor, which a colleague in the industry recommended to me. At first, I thought it would be another dry investing book – but it turned out to be one of the most practical and eye-opening reads I’ve come across.
Art of Execution investing is all about recognising that what you buy matters far less than how you behave after you’ve bought it. Freeman-Shor’s research – based on the real-life trades of 45 professional fund managers – shows why even the smartest investors often fail, and how ordinary South African investors can use the same lessons to avoid behavioural mistakes, hold on to multibaggers, and execute with discipline.
As you’ll see, the ideas themselves weren’t the problem. The difference came down to execution … what they did once they were in the position.
We like to think successful investing is about intelligence or research prowess.
But Freeman-Shor found that behaviour trumped brilliance. The winning managers weren’t necessarily better at picking stocks. They were better at managing themselves – cutting losers, riding winners, and avoiding panic.
And here’s the kicker: even elite professionals fall prey to the same psychological traps as retail investors. The real edge isn’t information. It’s execution.
Before diving into the results, Freeman-Shor did something clever. He categorised his investors not by style (value vs growth, tech vs financials), but by how they behaved once the trade was on.
Because, as he discovered, behaviour mattered far more than investment style.
Out of 45 professional managers, clear patterns emerged. Some froze, some cut ruthlessly, some added with conviction, and some let winners run. To make sense of it all, Freeman-Shor gave them memorable labels – animal archetypes that captured their instincts in the wild.
And like in nature, some traits helped them thrive … while others led to extinction.
Rabbits couldn’t cut their losses. They held on as a stock dropped 30%, then 50%, then 70%, hoping it would bounce back.
📉 SA Example: EOH—once the JSE’s tech darling, fell over 95% due to governance failures. Many investors averaged down, only to ride it all the way down.
📉 Global Example: Peloton and Teladoc—pandemic darlings that crashed as reality reasserted itself.
Lesson: Don’t freeze. If the facts change or the thesis breaks, exit. Quickly.
Squirrels sold winners too soon – taking quick 10% or 20% gains and missing out on long-term compounding.
📉 SA Example: Selling Capitec in 2010 after a double. It went on to return over 10,000% from its early days.
📉 Global Example: Early sellers of Amazon or Apple missed out on multi-decade compounding.
Lesson: The biggest winners take time. If the thesis is intact, let them run.
Assassins acted decisively. When an investment went wrong, they sold. No emotion. No ego.
✅ SA Example: Investors who cut Sasol in early 2020 during the Lake Charles debacle avoided a 90% drop.
✅ Global Example: Selling Blackberry once it was clear iPhone and Android had won the smartphone war.
Lesson: Capital preservation is step one. Don’t wait for hope to save you.
Hunters averaged down—but only when it made sense. They added to losers if their conviction increased, not out of denial.
✅ SA Example: Buying more Naspers during Tencent’s 2018 correction, if you still believed in the long-term thesis.
✅ Global Example: Buying Amazon in 2001 after a 90% drop, knowing e-commerce was just getting started.
Lesson: Averaging down only works if your investment case is still intact—and you’re not just throwing good money after bad.
Further Reading: Our interview with David Hansford of Long Beach Capital and what makes him one of South Africa’s best portfolio managers
Execution isn’t just about cutting losers or trimming profits. It’s also about recognising and holding onto the rare stocks that can transform your portfolio.
In 100 Baggers: Stocks That Return 100-to-1, Mayer studied the DNA of companies that returned 100x or more. The key lesson?
“To make 100x your money, be prepared to look wrong for a long time.” – Christopher Mayer
These stocks don’t look like obvious winners early on. In fact, many suffer brutal drawdowns along the way.
Further Reading: Some of our best investing stock ideas for 2025
One or two multibaggers can make your whole portfolio … even if you get a lot of other calls wrong.
And here’s the real kicker: companies that multiply and compound wealth in extraordinary ways rarely fit neatly into a discounted cash flow model or tidy spreadsheet. Spotting them requires vision, patience, and an understanding of where the world is headed – and how vast a potential market could become. They often look expensive, risky, or unconventional at first glance… until they redefine entire industries.
The irony is that many of the smartest, most intellectual investors miss these opportunities. Anchored by labels like “deep value,” “contrarian,” or “quality at a reasonable price,” they dismiss game-changing companies precisely because they don’t fit traditional moulds. But clinging too tightly to outdated frameworks can blind you to how the world is evolving – and to the rare businesses that can turn out to be 10x, 50x, or even 100x investments.
Further Reading: Some of the Best Global Equity Funds Compounding Wealth in South Africa today
Here’s the paradox: professional investors are paid to find opportunities like this, but are often the least able to hold them.
1. Short-term performance pressure: Clients demand quarterly results.
2. Benchmark fear: Deviating too much from peers can get them fired.
3. Too much volatility = too much career risk. Holding a wild winner can make them look reckless.
So they trim early – not because it’s the best decision for the portfolio, but to protect their jobs.
This is your edge as a private investor: you don’t have a boss breathing down your neck. You can think in decades.
Further Reading: Some of the Best SA Equity Funds Compounding Wealth in South Africa Currently
So how do you behave like a pro – but with the freedom of a private investor?
Freeman-Shor found that managers who were right only 49% of the time still made large profits … if they executed well.
That’s the real message:
You don’t need to be a genius stock picker. You just need to avoid the traps of fear, ego, and impatience – and give your winners a chance to do what they were meant to.
At Henceforward, we’ve seen first-hand how execution, discipline, and clear-eyed thinking matter more than the latest “hot” idea. The reality is that there are far more funds and asset managers competing for your life savings than there are truly great investment opportunities in the world. Discerning who to trust your retirement capital or life saving with is easier said than done – and it’s often not the big brand names you recognise.
In fact, boutique managers who can act nimbly are often better equipped to capture opportunities, while broad exposure through index and passive funds can make just as much sense in building long-term wealth. The key isn’t choosing between active or passive, or between “growth” and “value.” The key is having a strategy – and executing it with discipline.
Carl-Peter is a Certified Financial Planner® and Director of Henceforward, a boutique wealth and family office firm based in South Africa. With over 20 years of global experience in financial planning and offshore investing, he specialises in helping high-net-worth individuals navigate markets with discipline and clarity. At Henceforward, Carl-Peter and his team focus on flat-fee, conflict-free advice—empowering clients to cut through the noise, avoid common behavioural pitfalls, and build long-term wealth with confidence.
