The Biggest Retirement Mistakes People Make (Avoid These!) Jesse Cramer

The Biggest Retirement Mistakes People Make (Avoid These!) Jesse Cramer

Author: Andrew Giancola March 28, 2026 Duration: 1:04:56
Join the community built to help you master your money, stay accountable, and reach financial freedom.  👉 Try Master Money Academy free for 7 days today! In this episode of The Personal Finance Podcast, Andrew sits down with Jesse to explore critical retirement planning decisions—why Social Security isn't just a math problem and the biggest mistakes people make when claiming, when delaying benefits makes sense versus when claiming earlier is smarter, how married couples should think differently than singles, why Roth conversions are both overused and underused, the danger of overly optimistic return assumptions like 12% or 10%, the number one thing retirees get wrong about their own spending, and the most important actions to take 5-10 years before retirement. Listen to The Business Show here. Join The Master Money Newsletter where you will become smarter with your money in 5 minutes or less per week Here! Partner Deals Join the loyalty program for renters at joinbilt.com/PFP  Indeed: Start hiring NOW with a SEVENTY-FIVE DOLLAR SPONSORED JOB CREDIT to upgrade your job post at http://Indeed.com/personalfinance Go to http://policygenius.com to get your free life insurance quote. Thanks to Fundrise for Sponsoring the show! Invest in real estate going to http://fundrise.com/pfp   Go to Acorns.com/pfp and start automating your investments and get a $5 bonus today! Get 50% Off Monarch, the all-in-one financial tool at http://www.monarch.com/PFP  DeleteMe: Go to https://joindeleteme.com/PFP20/ and Use Promo Code PFP for 20% off! Connect with Jesse Cramer: Personal Finance For Long-Term Investors Podcast The Best Interest Website X Instagram Linkedin Connect With Andrew on Social Media: Instagram TikTok Twitter Master Money Website Master Money Youtube Channel Learn more about your ad choices. Visit megaphone.fm/adchoices

Hosted by Andrew Giancola, The Personal Finance Podcast is a straightforward conversation about building a practical and prosperous life. Andrew, who also runs Master Money, doesn't hold back on the specifics-you'll hear his actual strategies for managing money, investing in stocks and real estate, and developing business ideas. The focus is on actionable steps, from negotiating a higher salary at your current job to constructing reliable streams of passive income. The goal isn't just accumulation for its own sake, but creating the financial foundation that grants you more choices and autonomy. Each episode of this podcast is designed to demystify wealth-building, moving beyond theory to the tactics that can free up your time for the things you value most, whether that's traveling the world or simply reclaiming your day from financial stress. It's a direct resource for anyone ready to move from thinking about money to actively building a more secure and expansive future.
Author: Language: en-us Episodes: 100

The Personal Finance Podcast
Podcast Episodes
This is THE BIGGEST RISK to Your Retirement Portfolio [not-audio_url] [/not-audio_url]

Duration: 1:00:07
Two retirees. Same portfolio. Same returns. One ran out of money at 87. The only difference was when the bad years hit. Here is how to make sure you are not the unlucky one. 👉 Join Andrew's FREE Masterclass The Portfolio…
The Insurance Crisis Nobody Is Talking About (With Bob Litterman) [not-audio_url] [/not-audio_url]

Duration: 51:44
Your home insurance bill is not going up because of inflation. It is going up because of a risk that was mispriced for decades and is now coming due. Episode Sponsor Coalition for an Insurable Future Website: https://coa…
How to Become a Stealth Wealth Millionaire (With JC Rodriguez) [not-audio_url] [/not-audio_url]

Duration: 1:04:11
Real millionaires do not look rich. They look boring on purpose, and that is exactly how they got there. 👉 Join Andrew's FREE Masterclass The Portfolio Pyramid: https://event.webinarjam.com/q05p7/register/q05p7b65?webina…
How to Shave Off 7+ Working Years and Retire Early! [not-audio_url] [/not-audio_url]

Duration: 57:02
Most people try to retire early by saving more and spending less. The people who actually pull it off use these six strategies instead. 👉 Join Andrew's FREE Masterclass The Portfolio Pyramid: https://event.webinarjam.com…
Is the American Dream Dead? (With Freddie Smith) [not-audio_url] [/not-audio_url]

Duration: 1:00:53
Millennials and Gen Z are not broke because of laziness but a broken system. Here is what is actually going on and what you can do about it. 👉 Join Andrew's FREE Masterclass The Portfolio Pyramid: https://event.webinarja…
How Companies Are Quietly Robbing You! With Lindsay Owens [not-audio_url] [/not-audio_url]

Duration: 57:03
The store already knows how much you are willing to pay. They are just waiting for the right moment to charge you that exact amount. 👉 Join Andrew's FREE Masterclass The Portfolio Pyramid: https://event.webinarjam.com/q0…
12 Financial Rules of Thumb That Let You Spend More on What You Love [not-audio_url] [/not-audio_url]

Duration: 16:18
What if the secret to spending more on what you love is not making more money but having better rules for how you spend it? 👉 Join Andrew's FREE Masterclass The Portfolio Pyramid: https://event.webinarjam.com/q05p7/regis…
How to RETIRE BY 30! (With Cody Berman) [not-audio_url] [/not-audio_url]

Duration: 1:03:42
Nobody teaches you that financial independence is a spectrum. Here is the mindset shift that changed everything. 👉 Join Andrew's FREE Masterclass The Portfolio Pyramid: https://event.webinarjam.com/q05p7/register/o37wxuz…