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Sleep Well Investments Framework
Finding time-tested businesses trading at a reasonable price - helping investors sleep well.
"Ultimately, nothing should be more important to investors than the ability to sleep soundly at night," Seth Klarman.
Unfortunately, I haven’t!
I have fallen into the trap of buying companies growing at all costs and broken businesses at cheap valuations! While that looked great when the market was optimistic, it was a disaster in uncertain times. With the benefit of hindsight, these baskets of stocks dropped the hardest.
This numbing experience led me to change my investment process radically.
From this day on -
I will only look into time-tested businesses that have proven they can defend their moats and generate high returns on invested capital over time.
I will only buy these businesses when they perform on my Thesis Tracker and when the price is right.
They must score above 13/20 points on the Sleep Well Investment checklist to earn a position in my Sleep Well Portfolio. Below is my scoring system.
You might not have heard of some of these names, but they are surprisingly impressive in their niche markets, with some having total market command.
The universe of these time-tested businesses is surprisingly large, but rarely are they offered at a reasonable price. So, the trick is to find a relatively unknown and under-appreciated (mostly boring).
Here are the links to some of them:
The VAT Group - Vacuum valve monopoly +32% CAGR since IPO
Shimano - Bike component monopoly +12% CAGR
Floor and Decor - Future monopoly in hard-surface flooring +30% CAGR
MIPS - Helmet safety monopoly +45% CAGR
Thor Industries - RV monopoly +14% CAGR
Medical Device Monopoly +17% CAGR
Sleep Well Investment Checklist explained
At the core, the checklist is adapted from
Anti-fragility concept borrowed from Nassim Taleb,
Irreplaceability from Anthony Deden,
Mundane businesses from Matthew McLennan,
And various studies from other reputable investors. They provided me with abundant questions but focused on the right aspects when judging if a business can endure the test of time.
At a high level, I have grouped the criteria into three categories in order of importance:
Survival - Business quality [13 points]
Endurance - Competitive position and risks [4 points]
Fair price - Valuation [3 points]
The first group investigates how a business has survived the test of time and the likelihood it will still be around for decades. The second category assesses whether the business can endure the test of competition and external shocks by measuring its moat direction. Finally, I use multiple valuation methods to estimate the business's intrinsic value and establish a price range to acquire a piece of the business that provides a high level of margin of safety.
Notice that business quality (17/20 total points) is more important than valuation (3/20 total points). The margin of safety for me comes mostly from the resiliency of the business than the cheapness of it. This is not a knock-on to value investing. The method still allows me to penalize overvaluations, but I am more comfortable choosing business quality over a bargain price.
Sleep Well Investments aims to analyze only top-quality businesses (monopolies, oligopolies, market leaders) and avoid bad ones. Henceforth, points are deducted for unconvincing missions, commoditized/fad products, high competition, low barriers to entry, business risks, and overvaluation.
The following table breaks down what I analyze under the three categories:
A business is rated resilient and investable if it achieves 13 points. For one reason or another, it lacks future visibility but is made up for convincing valuation even in the worst-case scenario. Next, with a score above 15, I rate a business anti-fragile. Here, I believe the business will thrive under external stress and deserve a higher portfolio allocation, but the trade-off is that valuation won’t be cheap. Finally, a business reaches the highest level- sleep well. They are anti-fragile businesses, and their valuation is also compelling. In this case, I would happily allocate 5% of my capital to acquire a piece of this business.
13 = resilient business - 1-3% of the portfolio at cost-basis
15 = antifragile business - 3%
16+ = sleep well business - 5%
Investment Thesis tracker
Sleep Well Investments stay ‘sleep well’ if they continue overcoming the competition and unknowns over time.
That’s why I also track their market share movements vs. key rivals.

As shown in the table above, green means gaining market share, red means losing, and yellow means stable. Gaining or losing market share speaks volumes about the quality of the moats and barriers to entry.
Consider this:
A business expanding its market share relative to key rivals is likely a result of widened competitive moats and stronger pricing power. In theory, that should allow the business to sell products at a higher price, buy supplies at a lower price, and enter new markets and products more effectively. Operationally, that likely leads to better cash conversion and higher free cash flow growth. From an investment perspective, the return on invested capital (ROIC) is likely healthier than its peers.
Market share movements encapsulate all the underlying aspects above. Simple and elegantly effective (as my fellow investor -Ryan Reeves, author of Business Breakdownssummed it up succinctly). Thank you, Ryan 🙏.
Tracking market share also encourages investors to think long-term and provides a good opportunity to update the sleep well scorecard, which measures the quality of deep-dived businesses. You can see the current score at the top of this page.
So, join my quest to find and track sleep-well investments!