Jesse Cramer

Rochester

Freelance Contributor and Podcaster at Freelance

Founder of The Best Interest • Nominated 2022 Personal Finance Blog of the Year

Articles

Pedal to the Metal?

2 days ago | goodmenproject.com | Jesse Cramer

Comedian George Carlin joked,What’s your driving style? The Bullet floors it in the left lane, weaving through traffic like Richard Petty, convinced speed limits are merely suggestions. The Oblivious Cruiser plants themselves in the middle lane at precisely 47 mph, blissfully unaware of the mile-long parade of frustrated drivers behind them. The Wildcard alternates between tailgating, sudden braking, and last-second exits, as if being chased by an invisible swarm of bees. Or are you the Zen Master?
The 15 Tariff Questions I’ve Heard Most

1 week ago | goodmenproject.com | Jesse Cramer

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Editor’s note: Here are my other recent tariff articles:15 Questions for Scared Investors Right NowLet Them Trade StocksMy blog inbox and my professional inbox exploded last week with tariff questions. At first, I thought, “Everyone’s already talking about it…do I really need to add my voice to the fray?”But the questions kept coming.
"Asset-Liability Matching" Aligns Your Money to Your Future

1 week ago | bestinterest.blog | Jesse Cramer

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:I see some people thinking about their portfolios incorrectly, and a concept called “asset-liability matching” can help. Let’s imagine a portfolio…50% stocks, half US and half international. Plus 50% bonds, half short duration (~2 years) and half longer duration (~8 years).
Stocks, Rock, and Two Blasting Speakers

2 weeks ago | bestinterest.blog | Jesse Cramer

This is a true story. Growing up, our neighbor was erratic. He was an unwell man, and it manifested in many ways. To me, as a child, he was scary. When I was a teen, a weirdo. Now, as an adult, I see the pragmatism of avoiding him mixed with sympathy for his unlucky lot in life. Long-time dedicated readers might ask, “That neighbor?!” Yep. Same one. Welcome to rural NY! Today’s main character was their middle-aged son.
The ‘Asset Location’ Dilemma: Tax Strategy or Tax Trap?

2 weeks ago | goodmenproject.com | Jesse Cramer

The world of financial planning comprises many strategies and tactics, some big and some small. Dollar-cost averaging, sequence of returns, tax-loss harvesting, and the list goes on. Depending on who you ask, the process known as “asset location” could be one of the more impactful arrows in your financial planning quiver…or it could be a total waste of time. So which is it? Does asset location matter in the long run? And if so, can we quantify it?
You Win or You Die...or You Just Have a Normal Retirement

3 weeks ago | bestinterest.blog | Jesse Cramer

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:George R.R. Martin’s epic fantasy saga, A Song of Ice and Fire, started in 1996, with Martin publishing the first three books over five years. The books built a cult following thanks to their gritty realism, deep characters, and (let’s be honest) a willingness – or even a penchant – to kill off anyone at any time. Then HBO came calling.
35 Lessons From 35 Years

3 weeks ago | goodmenproject.com | Jesse Cramer

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:I originally wrote this in 2021 (31 lessons in 31 years). But here in 2025, I’ve had a crazy busy week and not enough time to write a brand-new article. Perfect timing though! My birthday is Saturday, so let’s just update this post for 35 years!Last year, I wrote about the amazing growth that can occur in a single decade. Here’s that article: A Lot Can Change in Ten Years.
Should I ‘Reset’ Retirement Withdrawals in Bad Markets?

1 month ago | goodmenproject.com | Jesse Cramer

First things first, great name/city combination, Red. This is a really interesting question, and the place to start is by adding some…color. Let’s apply a real scenario to Red’s question. We’ll look at a family who retired in July 2021. We’ll make some very simplified assumptions:They retired with $3M. They followed the 4% Rule precisely. Their initial withdrawal rate was $10,000 monthly, and they adjusted for inflation yearly.
Are Dividends and Income Part of My Retirement Withdrawal Rate?

1 month ago | bestinterest.blog | Jesse Cramer

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Barry wrote in and asked: Jesse – I’ll need about $100,000 per year from my portfolio in retirement. I have $3M in my retirement portfolio. It’s producing about $60,000 in income and dividends for me, meaning I only need to sell $40,000 (net of taxes) of the principal value to fund the rest of my need. By my math – $40,000 divided by $3M is about 1.3%.
15 Questions for Scared Investors Right Now

1 month ago | bestinterest.blog | Jesse Cramer

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:I want to float these punchy, Socratic questions out there and let them sit. I want you to pause and think. I don’t want to tell you any of my answers or any “best practice” answers. Those answers don’t matter. Your answers matter. It’s a bit like therapy. It’s not about me. It’s about you, and it’s important that you come to your own conclusions.