Good morning! It might be smoggy outside, but hopefully you're feeling clarity in your financial plans. Today's email includes: *A listener who asked, "My retirement portfolio is 100% S&P 500 - and it's done great! Why do you say it's wrong?!" *A $500K Roth conversion mistake, and a reminder about the clients I prefer to work with. *Other content about "solo agers," big goals, and Social Security calculators. Ask Me (Literally) Anything We're getting ready to record Episode 150. Many of you...
11 days ago • 2 min read
Good morning! Today's email includes: *A different type of "ask me anything" episode, coming soon. *A podcast episode devoted entirely to your Roth conversion questions *A sequence-of-returns model that you can use and play with. *And other people's content about ignoring the news, knowledge vs. understanding, and being a unique human. Ask Me (Literally) Anything We're getting ready to record Episode 150. Many of you know that my normal AMA episodes focus entirely on retirement and financial...
18 days ago • 2 min read
Good morning. It's hot. 🌶️ Today's email includes: *A new podcast episode about "risk parity" portfolios, and the three H's of retirement, and the five ways to use your money for good. *An old article about "benefits hacking" - an immoral practice, or a genius way of playing within the rules? *Some great content from others, including a great chat Are You Hoarding, Hustling, or Harvesting? In this new podcast episode, I was joined by Frank Vazquez -- retired attorney, creator of Risk Parity...
24 days ago • 2 min read
Good morning from beautiful Keuka Lake, where we're spending a few days at my wife's family reunion. Today's email includes: *A new podcast episode about identity, relationships, and structure - three vital components of retirement that money cannot solve for. *What Warren Buffett called "financial mass destruction" and how to avoid it It *Won't* Automatically Happen Retirement readiness is not only financial. Your life needs structure that many people aren't ready for. It doesn't happen...
about 1 month ago • 1 min read
Good morning! Today's email includes... The latest "Ask Me Anything" episode - how to "portfolio-tize" your various accounts. We all know stocks beat bonds...but only over the long run. What kind of timelines are we actually talking about? How to "Portfolio-tize" Your Various Different Accounts? You've got a 401(k), an old IRA, a Joint Taxable account with your spouse...oh, and all their retirement accounts too. How do you create one cohesive portfolio? How do you "portfolio-tize" these...
about 1 month ago • 1 min read
Good morning! Today's email includes... The latest "Ask Me Anything" episode - featuring opportunity costs, TIPS, and asset location. Why a small 10% difference can lead to infinite differences - in both health and wealth. Stop Eating!! It's Costing You BILLIONS! Well...that headline isn't quite true. Though some people like to frame "opportunity cost" as the monster sapping your very life-force. In this "Ask Me Anything" episode, I tackle (3) great retirement finance questions... First -...
about 2 months ago • 2 min read
Good morning! Today's email includes... The 14 biggest risks in retirement - and how to beat them. [Part 2 of a two-part series] A funny connection between investing and the weather - and our strange perceptions of both. The 14 Retirement Risks - and How to Beat Them In these two episodes, Jesse applies Charlie Munger's principle of inversion to retirement planning, arguing that instead of defining success alone, investors should first identify how retirement plans fail and then design...
about 2 months ago • 1 min read
Good morning! Today's email includes... The 14 biggest risks in retirement - and how to beat them. [Part 1 of a two-part series] A funny connection between investing and the weather - and our strange perceptions of both. The 14 Retirement Risks - and How to Beat Them In this episode, Jesse applies Charlie Munger's principle of inversion to retirement planning, arguing that instead of defining success alone, investors should first identify how retirement plans fail and then design strategies...
about 2 months ago • 1 min read
Good morning! Today's email includes... A description of a "life file" -- and an argument for why you need one. A conversation tackling a few hotly debated ideas in retirement planning. Why Everyone Needs a Life File: Friend-of-the-blog Mary and I had a wonderful conversation this week about an important – but depressing – topic: Everyone should get their sh** together in case they get hit by a bus. Seriously. It might not be a bus. But you never know when death will come knocking. The last...
2 months ago • 1 min read