WOULD YOU
RATHER?

Glen's Take:

Compounding is the eighth wonder of the world. 20 years of Buffett-level returns builds generational wealth with far less stress. Soros made his money betting against entire currencies — exhilarating, but I like sleeping at night. Sometimes.

Glen's Take:

Look, I wrote EIGHT books about this thesis. Every. Single. Share. Of FNMAS. The upside is asymmetric. Berkshire is a beautiful business, but FNMAS is the trade of a generation. I'm biased and I don't care.

Glen's Take:

One dinner with Munger would teach you more about decision-making than a semester at Harvard. Icahn is fascinating, but Munger's mental models are a cheat code for life. Plus he'd probably tell you exactly what you're doing wrong. Painfully.

Glen's Take:

A -90% loss means you need a 900% gain just to break even. The math of loss avoidance is brutal and unforgiving. Catching a 10-bagger is amazing, but keeping your capital alive is how you survive long enough to find one. Rule #1: Don't lose money.

Glen's Take:

Bottoms are when fortunes are made. Tops just tell you when to sell — but buying at the exact bottom with maximum conviction? That's generational wealth. March 2009 buyers are still laughing.

Glen's Take:

Macro forecasting at the perfect level beats any single company bet. You'd know every rate cut, every recession, every boom before it happened. You'd be the greatest trader in history. Insider knowledge of one company caps your upside.

Glen's Take:

Simons generated 66% gross annual returns for decades at Renaissance. That's not investing — that's a money printer. Lynch was legendary, but Simons broke the simulation.

Glen's Take:

I literally put my entire net worth into Fannie Mae preferred shares. Conviction is a feature, not a bug. Diversification is protection against ignorance, per Munger. If you truly know something, concentration is how you get rich. (This is not financial advice.)

Glen's Take:

Numbers tell you what happened. People tell you what's coming. Body language, conviction, tone — you learn more in 30 minutes with a great CEO than in 300 pages of filings. Plus, free coffee.

Glen's Take:

A 100% win rate compounds without drawdowns. No losing streaks, no emotional spirals, no margin calls at 3 AM. 5% gains stacked infinitely with zero losses beats everything over time. The turtle wins this race.

Glen's Take:

Stock picking is a repeatable skill. Market timing is a coin flip dressed in a suit. Even if you're 'the best' at timing, markets are driven by randomness. The best stock picker finds hundred-baggers and just holds.

Glen's Take:

Twenty extra years of compounding turns $1,000 into a fortune. Starting at 15 gives you the most valuable asset in investing: time. A million dollars at 35 sounds impressive until you realize the 15-year-old version of you is already ahead.

Glen's Take:

Edge comes from understanding what others don't. If you can explain it to a child, so can everyone else — and it's priced in. The money is in the gap between complexity and understanding. That's where FNMAS lives.

Glen's Take:

Bridgewater's all-weather approach is intellectually elegant and you'd learn more about risk management than anywhere else. Cathie's approach is exciting, but the volatility would give me more gray hairs than I already have.

Glen's Take:

This one is almost too easy. Bitcoin at $1 is a no-brainer — you're buying something that will 100,000x. Shorting Tesla at its peak sounds good until you remember the market can stay irrational longer than you can stay solvent. Just ask all the Tesla shorts who went bankrupt on the way up.

Glen's Take:

Freedom is the ultimate return on investment. What's $200 billion worth if you're sleeping on a factory floor, getting sued by everyone, and tweeting at 2 AM? I'll take kiteboarding in Miami Beach and Rocket League at midnight, thanks.

Glen's Take:

The US market has outperformed global markets for decades. Rule of law, innovation culture, deepest capital markets on earth. American exceptionalism is real and investable. I'll take the S&P 500 over the rest of the world any day.

Glen's Take:

Bloomberg gives you data. The Fed Chair gives you the future. One phone call before each FOMC decision is worth more than every terminal in Manhattan. Also, Bloomberg terminals cost $24K/year, so the free part is nice, but it's not 'knowing what the Fed will do next' nice.

Glen's Take:

2008 was a longer, deeper opportunity. You'd buy bank stocks at 90% discounts, scoop up real estate for pennies, and load up on FNMAS knowing the government would eventually do the right thing. COVID was a V-shaped recovery — amazing, but 2008 gave you more time to accumulate.

Glen's Take:

Being right and early is my entire investing identity. I've been right about FNMAS for years. Early? Sure. But being right matters more than being timely. Being wrong and making money is luck. Being right and early is conviction that eventually gets rewarded. Eventually.

Glen's Take:

Drawing lines on charts is astrology for finance bros. Fundamentals tell you what a business is actually worth. I want to know the earnings, the balance sheet, the competitive moat — not whether the RSI crossed the MACD on a Tuesday during Mercury retrograde.

Glen's Take:

Burry-level conviction when you're right is how you make 489% in a single trade. Buffett's patience is legendary, but patience without conviction is just waiting. I want the ability to see what nobody else sees and bet the farm on it. Wait — that's what I already did.

Glen's Take:

A $1B IPO means you built something real. The founder shares, the control, the upside — it all dwarfs $100M in index funds. Plus, you built it. That matters. Money you earn hits different than money you inherit.

Glen's Take:

Leverage kills. One percent fees on leveraged trades is death by a thousand cuts. Zero-fee trading lets you compound without friction. Leverage makes you feel rich until the margin call makes you feel poor. I choose survival.

Glen's Take:

I already know my thesis is right. What keeps me up at night is the WHEN. Knowing the exact date FNMAS goes to par? That's the cheat code. I could size positions perfectly, manage cash flow, and sleep like a baby. Instead, I'm here writing Would You Rather questions at midnight. The thesis is right. The timing is the torture.