Hello
In the world of investing, you’ll often hear that to get great returns, you have to take great risks. While there's truth to that, we believe there’s a crucial distinction to be made. The most successful investors don't take reckless chances; they take smart, calculated risks. Understanding this difference is key to building wealth without betting the farm.
We're excited to explore how you can learn to evaluate opportunities, manage potential downsides, and take the kind of calculated risks that lead to incredible growth.
The Difference Between a Gamble and a Calculated Risk
A reckless risk is a gamble. It's making a decision based on hope or hype, without doing your homework. A calculated risk, on the other hand, is a decision made after careful research, analysis, and planning. It’s a move where you understand the potential upside and the potential downside, and you have a plan to manage it. We think of it as being a pilot, not a passenger.
Here’s why we believe this mindset is so essential:
But what can you actually DO about the proclaimed ‘AI bubble’? Billionaires know an alternative…
Sure, if you held your stocks since the dotcom bubble, you would’ve been up—eventually. But three years after the dot-com bust the S&P 500 was still far down from its peak. So, how else can you invest when almost every market is tied to stocks?
Lo and behold, billionaires have an alternative way to diversify: allocate to a physical asset class that outpaced the S&P by 15% from 1995 to 2025, with almost no correlation to equities. It’s part of a massive global market, long leveraged by the ultra-wealthy (Bezos, Gates, Rockefellers etc).
Contemporary and post-war art.
Masterworks lets you invest in multimillion-dollar artworks featuring legends like Banksy, Basquiat, and Picasso—without needing millions. Over 70,000 members have together invested more than $1.2 billion across over 500 artworks. So far, 25 sales have delivered net annualized returns like 14.6%, 17.6%, and 17.8%.*
Want access?
Investing involves risk. Past performance not indicative of future returns. Reg A disclosures at masterworks.com/cd
It Puts You in Control: When you take a calculated risk, you are making an informed choice. You’re not just hoping for the best; you're operating from a position of knowledge and strategy.
It Maximizes Your Learning: Even if a calculated risk doesn’t pan out exactly as planned, the process of research and analysis makes you a smarter investor. You’ll gain valuable insights that you can apply to your next move.
It Builds Long-Term Confidence: Knowing you have a solid process for evaluating risk gives you the confidence to seize opportunities that others might be too afraid to touch. We see this as a massive competitive advantage.
How to Take Smarter Risks
We’re optimistic that you can develop the skills to become a savvy risk-taker. It’s all about creating a framework for your decisions so you can act with intention, not emotion.
Here is some actionable advice to help you get started:
Become An AI Expert In Just 5 Minutes
If you’re a decision maker at your company, you need to be on the bleeding edge of, well, everything. But before you go signing up for seminars, conferences, lunch ‘n learns, and all that jazz, just know there’s a far better (and simpler) way: Subscribing to The Deep View.
This daily newsletter condenses everything you need to know about the latest and greatest AI developments into a 5-minute read. Squeeze it into your morning coffee break and before you know it, you’ll be an expert too.
Subscribe right here. It’s totally free, wildly informative, and trusted by 600,000+ readers at Google, Meta, Microsoft, and beyond.
Do Your Due Diligence: This is non-negotiable. Before you invest in anything, you must do your homework. For a rental property, this means researching the market, analyzing the numbers, and getting a professional inspection. We encourage you to become an expert on any investment you consider.
Understand the Worst-Case Scenario: Ask yourself, "What is the worst thing that could happen with this investment, and can I handle it?" Having a clear understanding of the potential downside and creating a contingency plan (like having cash reserves) will help you make a more rational decision.
Start Small: You don’t have to hit a home run on your first try. We believe it’s smart to start with smaller, lower-risk investments to build your skills and confidence. As you gain experience, you can gradually take on bigger opportunities.
Taking risks is a necessary part of building wealth. The key is to make sure they are the right kind of risks—the ones that are well-researched, planned, and aligned with your goals.
We encourage you to look at your own risk tolerance. Are you ready to start taking smart, calculated risks to move closer to your financial goals?
Quick Poll (Your Turn!)
Before you go, I’d love to hear from you!
Want to work with us?
If you would like to start a newsletter like this, Sign up with Beehiiv.
Click to learn more and subscribe to the newsletter.