Becoming a Better Investor with Andy Rachleff

#19: Legendary investor Andy Rachleff joins Chris to chat about how you should be investing your money to build your wealth. They discuss the investing mistakes so many make, when it makes sense to pick stocks and why you might not want to max out your 401k. Andy Rachleff (@arachleff) is the co-founder and CEO of Wealthfront. He also serves as a the chairman of the endowment investment committee for University of Pennsylvania and as a member of the faculty at Stanford Graduate School of Business. Previously, Andy co-founded Benchmark Capital, one of the most successful venture capital firms of all time. Full show notes available at: https://allthehacks.com/investing-andy-rachleff   Partner Deals For all the deals, discounts and promo codes from our partners, go to: allthehacks.com/deals Resources Mentioned Get $5k Managed for free at Wealthfront Connect with Andy: Twitter | LinkedIn Wealthfront: Website | Blog | Guide to Financial Health Why Angel Investors Don’t Make Money: TechCrunch Article Why Rental Properties Are Not Good Investments: Wealthfront Article Burt Malkiel's Book: A Random Walk Down Wall Street   Full Show Notes (00:32) Who Is Andy Rachleff? (Episode Overview) (01:58) Andy's First Investment (05:54) Andy's Path from Investment Banking to Venture Capital (08:39) How Great Companies Are Started (10:50) Why Did Andy Feel the Need to Start Wealthfront? (14:36) Can You Be Successful Picking Stocks? (19:48) Is an Angel Investment in a Startup a Good Investment? (21:42) How Can You Make Passive Investing More Exciting? (23:17) What About Investing in Alternatives Like Art? (24:09) Is Real Estate or a Rental Property a Good Investment? (27:19) Investing Hacks to Save Money on Taxes (33:39) How to Make Changes to Your Investment Portfolio (34:56) Does It Make Sense to Invest When Markets Are at All-Time Highs? (39:02) When Should You Speculate with Your Investments? (40:46) Don't Always Evaluate Your Investment Decisions by How Much You Made or Lost (41:38) How Should You Change Your Investing Strategy When You Have More Money? (42:40) Are Wealth Managers Worth Their Fee? (45:01) Why a Good Tax Advisor Is Better Than a Wealth Manager (46:10) Andy's Winning Tactics for Negotiating (48:35) Why You Should Always Be Pareto Optimal (50:06) The Value of Liquidity and Why You Might Not Want to Max Out Your 401(k) (55:24) How to Connect with Andy Rachleff   Connect with All the Hacks All the Hacks: Newsletter | Website | Membership | Email Chris Hutchins: Twitter | Instagram | Website | LinkedIn Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.