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
Gen Z vs. The Old Money Rules w/ Lillian Zhang #1070 [not-audio_url] [/not-audio_url]

Duration: 53:49
Let’s talk about money and “the youths” today! While a lot of personal finance advice is evergreen and helpful to folks of all ages, it’s also important to reach people where they are and in the way they like to consume…
Friday Flight: Leftover Turkey Edition! #1068 [not-audio_url] [/not-audio_url]

Duration: 50:33
We’re taking a moment to slow down and reflect on what HTM listeners are truly grateful for during this busy holiday season. And yes… doing this on Black Friday is intentional. Instead of swapping stories about the hotte…
The World Is Getting Better w/ Marian Tupy #1067 [not-audio_url] [/not-audio_url]

Duration: 53:24
Though it seems like the world is in shambles, humanity has progressed quite impressively when you look at virtually any length of history. Our modern society has produced a slew of nice things that would have been hard…
Don’t Let Taxes Terrify You w/ Hannah Cole #1064 [not-audio_url] [/not-audio_url]

Duration: 56:49
“Taxes for creatives” could have also been the title of this episode, giving the more entrepreneurially minded the boost they need to officially launch a little business they’ve been considering. But for most folks the t…