THE 8-POINT INVESTMENT CHECKLIST – The Curious Practitioner

You’ve got an investment opportunity in mind—a stock, a vintage bag, a startup, a cryptocurrency. It sounds exciting?

But is it solid?

Is it worth your money, your time, your trust?

Let’s find out—using my 8-point investment checklist.

It’s what I call my universal method for assessing any investment opportunity—quickly, across any market. I developed it over 18 years of investing to help me step back, stay sharp, and avoid blind spots. I’ve used it to challenge my own thinking—and now, you can too.

All you need to do is answer 8 questions, as honestly as you can.

This tool won’t give you a verdict. What it offers is something more valuable: clarity.

No jargon. No hype. Just a structured way to step back, test your thinking, and decide whether to move forward with confidence—or walk away with peace of mind.

⚠️ Disclaimer: This isn’t a crystal ball.
It won’t predict returns or eliminate risk. But it will help you ask better questions—because good decisions start with clear thinking. Whether you answer YES or NO to each question, the outcome is not a recommendation, solicitation, or investment advice. It’s a thinking tool for educational purpose only.

Take this 8-question test to pressure-test your thinking. Ready?

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8 questions total

1. Arbitrage Opportunity

Can you resell this asset immediately for a profit, with a buyer already lined up or guaranteed?

What is an arbitrage opportunity—and why is it important?

An arbitrage opportunity arises when you can buy an asset and immediately sell it for a higher price. Because the resale is secured in advance, you skip the uncertainty that typically exists between buying and selling. This virtually eliminates holding risk, making arbitrage one of the safest and most efficient forms of investing. These opportunities are rare—but when they do appear, they’re often worth acting on quickly. Learn more

Yes No

Arbitrage locked in—great!

You’ve found a nearly risk-free gain. Just make sure the deal is legal, and all parties are reliable. These opportunities are rare because they require speed, access, and trust. But when they appear, they’re gold.

No arbitrage—what now?

That’s fine—most investments don’t offer this. But now, your focus shifts to how long you’re willing to hold the asset and whether you can realistically resell it later. Ask yourself: who might buy it later? Don’t enter blind. Know your potential exit routes.

2. Compelling Story

Is there a clear, engaging story or narrative behind this asset that would appeal to others?

Why the story behind an investment matters more than you think.

Humans aren’t naturally wired to invest—but we are wired to respond to stories. Narratives shape our perceptions, stir emotions, and influence decisions. In the investment world, a compelling story can create buzz, build belief, and ultimately drive demand. Assets backed by strong narratives tend to attract attention—and with it, future buyers. It’s often the story, not the numbers, that first opens the door to value. Learn more

Yes No

A compelling story? That’s a strong starting point.

Good. Strong narratives increase your chance of finding buyers later. Good job identifying an emotional or cultural hook. Just ensure the story has substance—and isn’t just wishful thinking.

Weak story? Might be hard to resell later.

Without a story, even great assets can go unnoticed. If an opportunity doesn’t resonate—emotionally or intellectually—it may never gain traction in the market. That doesn’t make it a bad investment, but it does mean you’ll likely have to work harder to spark interest and find buyers. Ask yourself: Would this convince me if I were on the other side? If not, it may struggle to stand out when it matters most.

3. Measurable Flows of People and Money

Is there measurable traction—buzz, demand and transactions—around this asset right now?

What flows tell us about interest—and future value.

People and money naturally flow toward stories they believe in. Investor interest isn’t just a feeling—it can be tracked through signals like trading volume, fund flows, social media chatter, news coverage, and even search trends. These indicators help you gauge whether the asset has a pulse—whether there’s a healthy cycle of supply and demand already in motion. Learn more

Yes No

There’s visible traction—momentum is real.

Great—this means the market is alive and you’re not alone. Visible flows of people and money signal real interest, and that’s encouraging. When attention builds, value often follows. Just be sure the momentum is sustainable—not just a passing trend or speculative spike.

Silence or low activity—time to investigate

No visible flows? It might be that people just aren’t buying the story. If there’s little buzz or movement, it may mean the asset hasn’t clicked with the crowd—yet. That could be because the narrative lacks calls to action, or simply hasn’t reached the right audience. Either way, you’ll need to dig deeper. Without traction, even a good idea can stay on the shelf.

4. Store of interest

Is this an asset that will keep people interested over time?

Why lasting interest makes all the difference and how it can protect your investment.

Some assets have a kind of magnetic pull—they stand out, resonate widely, and linger in people’s minds. These “stores of interest” are often unique, iconic, or emotionally charged, and they tend to hold attention across trends, cycles, and even generations. Think of gold, luxury watches, or beloved brands—they create symbolic value that lasts. The more an asset spreads and sticks, the more resilient its demand becomes over time. Learn more

Yes No

It’s a store of interest? You’ve got staying power.

Assets that stand out, spread easily, and leave a lasting impression tend to be more resilient. They weather market cycles better and often attract long-term interest as they carry emotional or symbolic weight that endures.

Limited appeal—fragile attention span

Assets that don’t stand out or spread or stick may struggle to hold attention. If the asset doesn’t catch attention or lacks emotional stickiness, it may vanish from investors’ radar. Be cautious with niche or trend-dependent ideas. Ask: what makes this memorable or desirable a year from now? If unsure, proceed carefully.

5. Generator of Value

Can this asset generate ongoing income or cash flows over time?

Why assets that earn are more resilient.

If it pays, it stays. Assets that generate value—like rent, dividends, royalties, or staking rewards—give you income regardless of market moves. They offer visibility and resilience, especially if the income can grow or scale through network effect. Learn more

Yes No

It earns while you wait—that’s powerful

If the asset pays you regularly, you’re not entirely dependent on selling it later. Look for value that can scale and is defensible—network effects, scarcity, or a competitive moat.

No value generation—relying on price only

If your only return depends on future resale, that’s a riskier bet. It’s fine in some cases (e.g., collectibles), but be sure you’re not just hoping. Ask: can I unlock any income from this asset?

6. Conducive Environment

Is the external environment (regulatory, economic, societal) favorable to this investment?

What could go wrong—and how to think about external risks.

Even great assets can fail in bad environments. Use the SCOPE lens: – Societal trends, Commercial and economic conditions, Operational and regulatory environment, Pioneering technologies, and External shocks. Each can tip the scales. Learn more

Yes No

The backdrop looks favorable—green light

If current trends, policies, and economics support your investment, it has a tailwind. Still, stay alert. Good environments can shift—so monitor the SCOPE factors over time.

Headwinds ahead—check your assumptions

Even the best asset can lose ground in a hostile setting. If legislation is tightening, sentiment is turning, or disruption looms,tread carefully. Be realistic about how external forces could impact the value of your asset.

7. Acquisition and Ownership

Can you securely buy, access, and hold this asset—with clear costs and control?

Why ownership and access matter more than people realize.

Buying the asset is one thing—we often underestimate the true cost of acquisition (take real estate for example when you add taxes, notary fees, insurances, works, etc.). But actually owning and accessing it, especially in moments of crisis, is something else entirely. Do you really own what you’ve bought? Between intermediaries, fine print, and logistical risks, many investors learn too late that access isn’t guaranteed. Clarity on ownership and control is not optional—it’s essential. Learn more

Yes No

You’re in control—well done

Secure access, transparent fees, and simple logistics put you in a strong position. It’s often overlooked, but real ownership is essential for peace of mind and long-term value.

Unclear access or hidden costs—watch out

If the cost of acquisition eats too much into the asset’s value—or if you don’t fully understand how it’s held or maintained—you could run into trouble. Hidden fees, unclear custody, or complex structures can quietly erode your return. Do your homework. If ownership isn’t safe, simple, or transparent, it may be wise to consider alternatives.

8. Sensible Price

Is the current price grounded—neither inflated by hype nor dragged down by irreversible decline?

Why entry price still matters—even with great assets

Even the best asset can be a bad investment at the wrong price. Buying into bubbles—or falling knives—can hurt returns or delay recovery. A fair entry point improves your margin of safety. Learn more

Yes No

Price looks fair? And you’ve got margin for safety? Great!

Smart. A good asset at a fair price is a classic winning combo. If it’s slightly undervalued, even better. Just make sure demand will remain.

Overpriced or oversold for good reasons —stay sharp

If it’s been bid up by hype—or is crashing for fundamental reason—you’re in unstable territory. Don’t rely on miracles. Be patient or walk away.

Your Results

You answered “Yes” to 0 out of 8 questions.