The Short Version: The difference of approach between a seasoned investor vs a novice Why we’re psychologically wired to focus on upside and ignore risk. It’s why so many investors get burned by deals that looked great on paper. The 2008 crash and the 2022 syndication blowups had the same root cause: people optimizing for returns without stress-testing the downside. Avoiding catastrophic losses matters more than chasing big wins. The math is unforgiving — a 50% loss requires a 100% gain just to break even. There’s a line from Keith Cunningham’s “The Road Less Stupid” that changed how I think about investing: “Novice investors ask how much can I make on a given deal. Seasoned investors ask how much could I lose.” It sounds simple and almost obvious. But the more I’ve invested, the more I’ve realized how rare it is for people to actually internalize this. Most investors lead with upside. They see a projected 18% return and start calculating how much they’ll make. They get excited by imagining the best case scenario. Seasoned investors do the opposite. They assume things will go wrong. How much of my capital is at risk? What’s the worst realistic outcome? Can I survive it? This single shift in thinking is the difference between building long-term wealth and blowing yourself up. Why We’re Wired to Ask the Wrong Question It’s not entirely your fault if you focus on returns first. Our brains are wired for it. Daniel Kahneman, the Nobel Prize-winning psychologist, spent decades studying how humans make decisions under uncertainty. One of his core findings: we consistently overweight potential gains and underweight potential losses. It’s called optimism bias, and it’s baked into our psychology. When someone shows you an investment with a 15% projected return, your brain lights up. You start imagining what that money could do for you. The risk section of the pitch deck? You skim it. You assume it won’t happen to you. This is why casinos stay in business. It’s why people buy lottery tickets. And it’s why so many investors get burned by deals that looked great on paper. The antidote is discipline. Training yourself to ask the hard question first, before the excitement takes over. What Happens When You Don’t Ask I learned this lesson the hard way. Back in the mid-2000s, I was buying rental properties like everyone else. The market was ripping. Prices kept going up. I was overleveraged and convinced I was a genius. I never seriously asked what would happen if the market turned. I didn’t stress-test my portfolio against a downturn. I assumed the good times would keep rolling. Then 2008 happened. I had negative cash flow, properties underwater, and no cushion. I wasn’t alone. Millions of investors got wiped out because they’d asked “how much can I make?” without ever asking “how much could I lose?” It took years to recover. And the tuition was expensive. But the lesson stuck. The