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How to Money

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

How to Money

iHeartPodcasts

Education, Business, Investing

4.6 • 3.2K Ratings

🗓️ 15 April 2026

⏱️ 57 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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!

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Transcript

Click on a timestamp to play from that location

0:00.0

This is an I-Heart podcast.

0:02.6

Guaranteed Human.

0:04.3

Welcome to How to Money.

0:05.7

I'm Joel.

0:06.1

And today I'm asking the question,

0:08.3

can millennials count on Social Security with Mike Piper?

0:37.1

Thank you. Social Security, more than music, clothing, or political views, it's potentially the biggest generational divide.

0:42.4

Boomers are stoked to finally be receiving their promise checks, while millennials and Gen Z,

0:49.1

Mary's sitting on the sidelines wondering if Social Security is even going to exist when the time comes for them to collect.

0:53.9

And while Social Security is highly unlikely to disappear entirely to evaporate overnight. It probably won't

0:55.6

look exactly the same as it does today either. My guest today is Mike Piper. He's a CFP. He's an author.

1:02.7

He's an OG blogger from 2008 over at his site, The Oblivious Investor. And I couldn't think of

1:08.8

anyone better to discuss this tumultuous topic with.

1:12.5

So, Mike, thank you so much for joining me today.

1:15.0

Very happy to be here. Quick, quick correction note there. I'm a CPA rather than a CFP.

1:20.0

That's what I should have said. CPA, not CFP. All right. So I love making mistakes early on in the podcast. That way, you know, I fall flat on my face. And hopefully it's all perfect from here on now. First question I ask everyone who comes on the show, Mike, is what do you like to splurge on? Craft Beer. One of my, you know, main things, I'm willing to spend a lot more than most people would. But it's okay because I'm saving and investing for the future at the same time. What is that for you? Sure. My number one hobby for the last 15 years or so has

1:51.1

been rock climbing. And so that involves travel to different places, especially because I live in

1:57.2

Missouri where there aren't a lot of mountains, so travel as you might imagine, but also various types of gear. If you ever see movies or people are putting gear into cracks

2:05.1

and things like that, all of that gear costs money. And you eventually build up a collection

2:12.2

of it over time. Were you glued to the screen when Alex Honnold was making his recent ascent in Taipei?

2:19.6

Yeah, myself and my wife and a bunch of friends, we were all watching it.

2:24.4

And we have a group chat on WhatsApp that we were kind of narrating it to each other and then chatting about it.

...

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