#168: Former portfolio manager Chris Doyle joins to discuss strategic ways to build and manage your investment portfolio. They do a deep dive on diversification, tax-award allocation, capacity and tolerance for risk, tax-loss harvesting, rebalancing and more.

Chris Doyle is a Research Scientist at the Stanford Autonomous Agents Lab. He co-founded the technology startup Grove to make financial services accessible and affordable for everyone. Before that, he was an investor at a macro hedge fund and had a trading career at Barclays Capital.

Link to Full Show Notes: https://allthehacks.com/investment-portfolios-chris-doyle

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Resources Mentioned

Chris Doyle: LinkedIn | Website

Wealthfront (Get $5k managed free and get a 0.5% APY boost)

Triumph of the Optimists: 101 Years of Global Investment Returns

Articles

• Mutual Funds That Consistently Beat the Market? Not One of 2,132. (Published 2022)
• Lump-sum investing versus cost averaging: Which is better?

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• #19: Becoming a Better Investor with Andy Rachleff
• #59: Save Money, Build Wealth and Just Keep Buying with Nick Maggiulli

Full Show Notes

(00:00) Introduction

(02:14) Important Factors to Consider Before Building a Financial Portfolio

(05:54) One of the Major Mistakes Made by Retail Investors

(07:50) How to Think About Financial Risk

(08:33) Importance of Asset Class Diversification

(13:47) How to Determine Which Asset Classes to Include

(20:19) Why People Add Emerging Markets to Their Portfolio

(21:15) The Argument for International Stocks

(22:18) The Case For or Against Real Estate

(23:41) Trading Commodity Futures

(28:18) Investing in Crypto

(30:52) Non-Traditional Investments

(37:04) Bonds and Fixed Income Allocation

(43:30) Cash Interest Rate vs. Long-Term Bond Interest Rate

(46:11) How to Think About Investing

(50:34) Ways to Migrate from One Portfolio to Another

(54:06) The Role of Tax Rates

(1:01:31) Rebalancing Portfolios

(1:03:04) Tax Loss Harvesting

(1:09:39) Direct Indexing

(1:12:37) How Often Should You Change Your Portfolio?

(1:14:50) Uninvested Cash

(1:17:22) How to Pick the Right Perfect Portfolio

(1:20:22) Financial Advisors: Humans vs. Software

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