Rip Van Winkle Approach: Automate Investing

In this special episode of Excess Returns, we share the most important investing lessons from more than 50 of our top guests. After asking more than 200 investors, strategists, academics, and market thinkers the same closing question about the one lesson they would teach the average investor, we compiled the most powerful, timeless, and repeatable insights into a single episode. This collection highlights common themes around patience, discipline, humility, diversification, risk management, and long-term thinking, while revealing how great investors navigate markets, behavior, and uncertainty.

Main topics covered:

• Why investing is about preserving and growing wealth, not getting rich

• Why neither get in nor get out is an investing strategy

• The role of base rates in decision-making

• The dangers of performance chasing

• Why you should look at your portfolio less often

• The importance of independent thinking and avoiding envy

• Treating stocks as businesses, not trading sardines

• Diversification across assets, strategies, and economic regimes

• The behavioral traps that destroy wealth

• Liquidity, supply and demand, and how markets really function

• The value of patience, long-term thinking, and sticking to your plan

• How to build a resilient portfolio that survives different market environments

• Why simplicity often beats complexity

• The role of humility, self-awareness, and keeping emotions out of investing

Timestamps:
00:00 Investing is about preserving and growing wealth
00:45 Why neither get in nor get out is a strategy
01:16 How we arrived at the one-lesson question
02:00 Finding a portfolio you can live with
03:00 Avoiding envy and chasing 10-baggers
04:00 Why watching markets too closely hurts results
05:00 The Matt Levine rule of unbelievable returns
06:00 The power of base rates
08:00 Look at your portfolio as little as possible
10:00 Treat your holdings like real businesses
12:00 Be invested early and think independently
14:00 Be kind to yourself and keep taking action
15:58 Do not chase performance
17:00 Treat every position like you put it on today
18:31 Your portfolio is secondary to your life
19:44 Buy when others are fearful
20:00 Be Rip Van Winkle, not Nostradamus
22:00 Navigate the noise and avoid the siren song
23:38 The value of simplicity and studying history
24:59 Patience and tuning out the noise
26:00 True diversification and preparing for unknown regimes
27:50 Stick to a strategy that fits your personality
29:00 Diversify and be humble about what you know
30:00 Most results come from the market, not manager skill
32:38 Keep investing simple
34:00 Focus on what is knowable
35:00 Believe in long-term economic and market resilience
37:00 Get out of your own way
38:22 Build a philosophy you can stick to
39:00 Misjudging probabilities and confidence
40:46 Book your gains and contain your losses
41:00 Diversification is protection against bad luck
42:00 Supply, demand, and liquidity always matter
45:00 Markets as a political utility
46:00 Find something real if you want true alpha
47:00 Write down your decisions
48:32 Why 100 percent indexing is unrealistic for most
50:00 Alpha through portfolio structure, not just stock picking
52:00 Dividends and long-run investing
53:56 Valuation, time horizons, and patience
55:00 Embracing uncertainty and avoiding pigeonholing
56:33 Rules-based processes
57:35 Buy good businesses, not just cheap ones
59:00 Think long term and save early
01:01:00 Focus on the basics first
01:02:00 Avoid catastrophic losses
01:03:22 Evidence-based investing and avoiding resulting
01:04:09 Know what you own and keep fees low
01:05:00 Simple strategies often work best
01:06:00 Compounding and emotional control
01:07:00 Treat savings as savings, not lottery tickets
01:07:50 Balance enjoying today with protecting tomorrow
01:08:00 Stay invested and think long term
01:08:41 Be humble, patient, and systematic
01:09:00 Do your own work and build conviction