Buying your first stock can seem like a scary, risky endeavor. My first purchase came on Feb. 27, 2009: six shares of Aflac for a grand total of $105. "Anything more than that would probably be throwing money away," I told myself.

And then, something funny happened. The market bottomed out 10 days later, and has been going up ever since. After three months, my investment doubled! After a year, it tripled. I was hooked. 

Hand arranging wood blocks stacked as step stair. Arrows pointing up are on the front of the blocks.

Image source: Getty Images.

The decade since has been kind to my family. The stock market -- adjusting for the different times I've been able to invest -- has returned a total of 37%. Over that same time frame, my portfolio has more than tripled that amount, returning 116%.

If that sounds confusing, here's an easier way to put it. The S&P 500 has returned about 10% per year based on when I've invested. My portfolio has returned 23% per year over the same time frame. That might not sound like a lot, but it's provided life-altering flexibility.

Here's the thing: there aren't complicated algorithms or secret scuttlebutt that have helped. Instead, three simple characteristics have dictated the companies I choose:

  • Financial fortitude
  • A high level of skin in the game from employees
  • Practicing the barbell technique

Those might sound complicated, but they are exceedingly easy to understand. Combined, they form what I refer to as the Antifragile (more on that word below) Framework for picking stocks.

Luck is an enormous factor

I'll get to those three characteristics in a minute. But it would be wildly irresponsible of me to not acknowledge what could be the biggest factor in my success: luck.

Back in 2009, my wife and I were preparing to quit our jobs as teachers and move to Costa Rica. That meant rolling over our retirement plans. It drove me to start learning about stocks.

The fact that it coincided with the bottom of the Great Recession -- and start of the longest bull run anyone could have imagined -- is the most fortuitous stroke of good luck anyone could ask for. Ten years later, it's clear how lucky anyone is who started investing at the arrow below.

Chart showing S&P 500's return over time with arrow pointing to market bottom in 2009

Data source: YCharts. Arrow added by author.

I did nothing to deserve this -- it simply is what it is.

A framework for picking stocks

In early 2013, I read a book that changed how I think about...well...everything: Antifragile, by Nassim Taleb. In it, Taleb talks about how the world can be divided into three broad categories:

  • Things that are fragile -- or break easily when stress is applied. A porcelain cup would be a good example. 
  • Things that are robust -- or are pretty much unchanged by stress. A simple piece of iron would be robust.
  • Things that are antifragile -- or that actually get stronger when stress is applied. Our muscles -- which get micro-tears when we lift weights and then grow back stronger -- are an example most people can understand.

Unconsciously, I had been aware of the first two. The third was a revelation. I took the broad ideas from the book and started applying them to how I picked companies to invest in.

Before this, I tried to predict which companies would be the most successful by creating a narrative about their future. That didn't turn out so well. The stock market doesn't care about the stories in my head.

After reading the book, I wanted to look for factors that were clearly measurable. And I wanted those factors to be the type of things that would tip the scales in favor of companies not only surviving tough times, but getting stronger because of them.

With that as a backdrop, here are the three factors -- in reverse order of importance.

Skin in the game

In the time of the Babylonian king Hammurabi, people wanted to build bridges. But they weren't willing to fork over money to a bridge builder who may not have been on the up-and-up.

To mitigate this risk, the bridge builder was forced to sleep underneath the bridge. What better way to guarantee the best construction: no paperwork, legislation, or background checks necessary. The bridge may fall, but if it did, the bridge builder would go with it.

In essence, this is the principle of skin in the game: the best way to get a fair deal is to make sure all parties have incentives that are aligned. In investing, this means I look for three things:

  • Founder-led companies: Because founders often view their company as a natural extension of themselves, they are intrinsically motivated to create something of lasting value.
  • High levels of stock ownership: If those intrinsic motivations aren't enough, I want to know management will only prosper if I -- as a shareholder -- prosper as well.
  • Outstanding Glassdoor employee reviews: While it's not a perfect system, you can get an idea for how satisfied employees are working at a company. Anonymous reviews are submitted, tabulated, and posted for all to read at

You can check the first two by using the SEC's Edgar database, typing in a ticker symbol, and looking for the most recent proxy, or DEF 14A filing. The third you can check by visiting, clicking on "Company reviews," and filling in the name of an organization.

If we look at the five most successful investments I've made over the past decade, they all share some of these characteristics.

Company Founder Role Insider Ownership Glassdoor Rating (5 Stars Maximum) (NASDAQ:AMZN) Jeff Bezos CEO & Chairman 16.1% 3.8 stars
Shopify (NYSE:SHOP) Tobi Lutke CEO & board member 8%* 4.0 stars
Mercadolibre (NASDAQ:MELI) Marcos Galerpin CEO & chairman 8.1% 4.0 stars
Paycom Software (NYSE:PAYC) Chad Richison CEO & chairman 16.1% 4.4 stars
Veeva Systems (NYSE:VEEV) Peter Gassner CEO & board member 14.4% 3.4 stars

Data source: Company proxy filings, Ownership data accurate as of last DEF 14A filing. Glassdoor ratings accurate as of Aug. 9, 2019. *Includes only ownership by Lutke. 

Combined, these five stocks have returned 520% for my family -- sextupling their original investment. Unfortunately, however, skin in the game alone is not enough to tip the scales in my favor. Case in point: My investments in GoPro and Fitbit incurred huge losses even though both companies were founder-led, had high levels of insider ownership, and enjoyed moderate-to-strong Glassdoor reviews.

That's why there's more to this technique than skin in the game alone.

Financial fortitude

The next thing I want to check is a company's financial fortitude. Specifically, there's one simple litmus test I want to consider:

If there were to be a crisis -- on par with the Great Recession -- tomorrow, how would it affect the company?

While the stocks I'm invested in would probably go down, I am more concerned with the business and its long-term health. That's because companies with lots of cash, little debt, and strong cash flows can actually get stronger because of a recession. How? They could

  • acquire start-ups at a discounted cost.
  • buy back its own shares at lower prices.
  • undercut competition on price -- losing money in the short term, but gaining market share in the long term as the competition goes under.

There are three very simple metrics I consult when evaluating financial fortitude: cash (including investments), long-term debt, and free cash flow. Using those same five companies as examples, here's where they stand.

Company Cash  Debt Free Cash Flow
Amazon $43.0 billion $23.3 billion $22.0 billion
Shopify $2.0 billion $0 $16.3 million
Veeva Systems $1.3 billion $0 $388 million
Paycom Software $95 million $32 million $144 million
Mercadolibre $2.8 billion $0.6 billion $168 million

Data source: Yahoo! Finance.

Admittedly, these comparisons are a little weird: Amazon is orders of magnitude bigger than Paycom, for instance. But there is a clear general trend: All of these companies have more cash than debt, and they all have positive cash flows.

Again, however, this alone isn't enough to make a stock a buy. Back in 2015, GoPro generated $107 million in free cash flow, and it ended the year with $474 million in cash and zero long-term debt. 

Since then, the stock has lost 75%! The final section will help explain why.

The barbell approach

When most people think of a barbell, they think of a long bar with equal weights on either side. This isn't a perfect analogy, because the barbell approach calls for:

  • Dedicating at least 80% of your resources to a safe and reliable investment.
  • Dedicating the other 20% to high-risk, high-reward ventures. Most of these ventures will fail, but when one "hits," it can be a huge success.

At the companies I invest in, I look for this type of dynamic. In general, it looks like this:

  • Safe end of the barbell: reliable and repeat business that's protected by an easily identifiable moat.
  • Risky end of the barbell: evidence of tinkering with new products, including previous "big hits."

Let's deal with the first of those two bullet points. When evaluating moats, it's important to understand all the forms they come in. I like to think of moats as existing in four different buckets.

  1. Network effects: Present when each additional user of a product or service makes it more valuable to all other existing users. Facebook is the most obvious example of this moat. The site wouldn't be worth anything if your friends weren't on it.
  2. High switching costs: This happens when changing from one company to another incurs high financial, emotional, or logistical costs. The most obvious example from most people's lives would be switching banks. With all of the connections you have -- paying credit cards, direct deposits, etc. -- leaving your bank can be a headache.
  3. Low-cost production: If one company can produce something at a consistently lower price than others, while having the same baseline quality, it will always win business. Alphabet -- parent company to Google -- is able to produce data for advertisers at a lower cost than just about anyone thanks to its search dominance.
  4. Intangible assets: These include valuable brands, (think Apple), patents (think pharmaceuticals), and government-regulated protections (think utility companies).

Without diving too far into the weeds, here is a summary of the most important moats for each of the five companies mentioned above.

Company "Safe" Business Key Moat
Amazon E-commerce and fulfillment

Low-cost production: The fulfillment center network guarantees one- or two-day delivery at low internal costs.

Shopify E-commerce platform

High switching costs: Once a store is up and running, merchants don't want to deal with switching providers.

Veeva  Veeva Vault

High switching costs: All of a company's high-value data is on one network. Switching incurs possibility of losing mission-critical data.

Paycom HR-related services

High switching costs: Once employees at a company are familiar with the interface, the costs to switch -- in terms of retraining and migration -- are huge.

Mercadolibre Online marketplace

Network effects: More buyers on the site means more merchants, which draws in more buyers.

To be sure, this isn't an exhaustive list. One of the reasons these companies have fared so well is that they are protected by multiple moats. Hopefully, though, you get the idea: A company needs to be dominant in its main line of business to secure the "safe" side of the barbell.

Incidentally, it is here that Fitbit and GoPro failed: They were both protected by weak moats -- brand value. Anyone can make a fitness watch or camera. It's easy to switch these products, there are no network effects, and neither company had a low-cost advantage.

But now, let's focus on the second half of the barbell: high-risk, high-reward ventures. It might seem like a waste to spend 20%-ish of your resources on projects that will probably fail. But if even one of those projects does well, it can change the entire trajectory of the company.

Mercadolibre is a case in point. Ten years ago, the company's payment system -- MercadoPago -- was an afterthought. Its marketplace was the real focus. But in just the past three years, MercadoPago has taken off. It's the key catalyst behind the stock's doubling in 2019 alone.

Mercadolibre, however, isn't the only one testing such ideas. Here's a look at some of the other high-risk, high-reward ventures at the other four companies.

Company High-Risk, High-Reward Venture
Amazon This is how AWS -- the main profit engine -- started. Current projects include moves into shipping, pharmaceutical delivery, and groceries.
Shopify Merchant services -- which now pull in over 50% of Shopify's revenue -- were once on this side of the barbell. Its current high-risk project is building out an independent fulfillment network.
Veeva Vault is now being tested in industries outside pharmaceuticals.
Paycom What started as a payroll tool has expanded since founding to include several HR-related areas, including healthcare benefits.

The bottom line: These companies aren't resting on their laurels. They are actively looking for new ways to make their customers' lives even better.

A final word on stock picking

This is by no means the only way to pick a market-beating portfolio. It may, in fact, not even represent a method of investing that will produce great results going forward.

Of course, you can borrow freely from this framework for your own investing. But the larger point I'd like to drive home is this: create your own framework. Start with small sums of money and review what's working and what isn't. As you gain more confidence, add more money. Over time, you might be surprised by how well you do.

And that success can provide your family with life-altering financial flexibility as well.

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.