Can Millennials Count on Social Security? w/ Mike Piper #1127

Can Millennials Count on Social Security? w/ Mike Piper #1127

Author: iHeartPodcasts April 15, 2026 Duration: 56:26

Let's talk about Social Security. More than music, clothing, or even political views, Social Security might be the single biggest generational fault line in America right now. Boomers are thrilled to finally be collecting on a promise decades in the making while Millennials and Gen Z are quietly wondering if there'll be anything left by the time we get there. And honestly? That concern isn't crazy! Social Security almost certainly isn't going away entirely, but it's probably not going to look exactly the same as it does today either. Mike Piper, CPA and Social Security expert, joins the show today to explore the future of Social Security, optimal claiming strategies, and how to plan for retirement amid uncertain benefits. Specifically covered: 

  • What happens when the trust fund is gone?!
  • Downsides of overly conservative financial plans 
  • Claiming strategies when we’re living longer
  • Adjusting plans after a health diagnosis
  • The Open Social Security strategy calculator
  • Taking opportunity cost into account
  • Early retirement considerations
  • Common mistakes with DIY investors
  • … and plenty more!

Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:

 

And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!

 

Best friends out!

See omnystudio.com/listener for privacy information.


Joel and Matt, two best friends who happen to be your guides through the world of personal finance, host this practical and approachable How to Money podcast. They cut through the noise and intimidation that often surrounds money topics, focusing instead on actionable strategies for everyday life. You'll hear straightforward conversations about getting out of debt, building an investment portfolio on your own terms, and mastering those small financial habits that add up to significant change over time. The core idea is that managing your finances shouldn't require a special degree or a wall of confusing terminology. This show from iHeartPodcasts is built on the belief that clear, unbiased guidance is a powerful tool for anyone. Each episode serves as a resource, offering knowledge you can apply immediately, whether you're just starting to budget or looking to optimize your long-term plans. Tune in for a down-to-earth discussion that makes business, education, and investing feel not only accessible but genuinely relevant to your journey toward financial confidence.
Author: Language: en-us Episodes: 100

How to Money
Podcast Episodes
Bouncing Back from Bankruptcy & Business Failure w/ Phil Sanders #1109 [not-audio_url] [/not-audio_url]

Duration: 55:56
Joel met Phil halfway through a marathon a few months ago – literally in the middle of the race. It’s funny how life works and after running side by side and chatting for half an hour it was clear he’d only scratched the…
Die with Zero w/ Bill Perkins #1106 [not-audio_url] [/not-audio_url]

Duration: 49:16
Most money advice is a broken record: save more, invest early, and wait for freedom. But what if the real risk isn't running out of money but instead is running out of time? In this episode, we’re challenging the "accumu…
Friday Flight - 401k Mullets, Crappy Coffee, & Bitcoin Bashing #1104 [not-audio_url] [/not-audio_url]

Duration: 42:14
Time for a Friday Flight- our little sampling of the week’s best financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will…