Introducing the Better Off Podcast: Unconventional and
entertaining insights on your money and life.

Host Jill Schlesinger, CFP, tackles sometimes uncomfortable and even
controversial money and investing issues, without the financial jargon.

Jill interviews informative and entertaining guests each week to uncover
surprising insights and give you actionable information to make the most
of your money.

Latest Episodes | Listen Now


Ep. 008 - Silicon Valley Disrupters with Brad Stone

I’m going to assume that a good portion of you subscribed to the Better Off podcast have used either Uber or Airbnb. I use Uber all the time and it seems like everyone I know has used Airbnb. My producer Mark just used Airbnb for a week in Tokyo and loved it. James Altucher, our guest from the second episode, basically lives full-time in various Airbnb locations.

It’s no exaggeration to say that these companies have almost single-handedly disrupted stodgy industries (taxi/limousine and hotel), become stars of the Silicon Valley venture capital world and made their impact felt across the globe. That’s why we were delighted to have a great conversation with Brad Stone, Bloomberg journalist and author of “The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley are Changing the World.”

Brad defines an upstart as either “a newly successful person” or “someone who does not show proper respect to the established way of doing things” — you’ll need to decide whether or not Travis Kalanick of Uber and Brian Chesky fall into one or both of those categories. They certainly were brash survivors who didn’t create the ideas that made each company successful, but somehow they were able to execute better (more ruthlessly?) than their competitors.

Unlike in his previous book about Amazon, “The Everything Store”, where CEO Jeff Bezos would not talk to him, this time Brad had access to all the key players and he writes a compelling page-turner. He opens the story with the 2008 Obama Inauguration, which founders of both companies were attending.

What lessons have these wildly successful upstarts learned over the past nine years? How have they matured and become better leaders? After reading this book, you’ll have a whole new perspective the next time you ride in an Uber or make an Airbnb reservation.

Better Off” is sponsored by Betterment. For more Silicon Valley updates from Brad, you can connect with him on Twitter and Facebook.

Please leave us a rating or review in iTunes.

Better Off” theme music is by Joel Goodman,

Ep. 007 - Fiduciary Rule with Jon Stein

A couple weeks ago, we devoted the entire interview portion of the podcast to the hotly debated Department of Labor fiduciary rule, which was set to begin implementation on April 10. We taped that interview just days before President Trump signed a Memorandum that instructs the DOL to examine the rule “to determine whether it may adversely affect the ability of Americans to gain access to retirement information and financial advice.”

In other words, the fiduciary rule could be toast. Well, not on this show–it’s going to be a running theme on Better Off because as a CERTIFIED FINANCIAL PLANNER™, fiduciary is an issue about which I’m deeply passionate. So is our guest this week, Betterment CEO Jon Stein.

By now it’s no secret that Betterment is the sponsor of Better Off. But that’s not the reason why we’re having Jon on today. Jon has been an industry leader on the issue of fiduciary, publishing an open letter to President Trump, and voicing his company’s support for the rule.

Jon’s take is simple and one that should resonate: U.S. investors should be able to trust that the financial advice they’re getting is in their best interest. As he stated in the letter, “Investing can be made intentionally complicated, and salesmen are clever. Left to its own devices, the investment industry for decades sold bad products to Americans.”

The good news is that Jon and I are not alone. There’s support out there from plenty of high-profile people, including U.S. Sen. Elizabeth Warren, D-Mass., who penned a letter to the DOL highlighting support for the fiduciary rule from several financial institutions, including Betterment, adding that a delay “would be a slap in the face to the companies that have invested, in good faith, for a deadline that has stood for the past year — and to the everyday worker deserving of the assurance that their retirement adviser is working in their best interest.”

Safe to say Jon and I have plenty to discuss!

Better Off” is sponsored by Betterment. For updates on the fiduciary rule process, connect with Betterment on Twitter and Facebook.

Please leave us a rating or review in iTunes.

Better Off” theme music is by Joel Goodman.

Ep. 006 - Kids and Financial Literacy with Beth Kobliner

You will often hear me say that before you worry about the financial future of your kids, you need to make sure you’re taking care of yourself first. But that doesn’t take you off the hook for discussing money with your kids.

Think of it as another one of the talks…so now in addition to the sex talk, the drug and alcohol talk, we can add the money talk. All of these conversations must occur at every stage of your child’s development, with age-appropriate messaging that the kids can absorb.

To help with your effort, this week we’re talking to Beth Kobliner, author of Make Your Kid A Money Genius (Even If You’re Not): A Parents’ Guide for Kids 3 to 23. Okay, okay, full disclosure, she’s also a friend of mine.

But that’s not why Beth is on “Better Off.” She’s on because it’s an important topic. I know there are a lot of you out there subscribed to this podcast, with kids or thinking about starting a family, wondering how to have such conversations:

  • How much debt should we take on for college?
  • Should I give my teen a debit or credit card?
  • Should I give my child an allowance?
  • My kid wants to move back home…should I charge rent?

Those are just some examples and there’s plenty more in the book. Whether you’re a rookie in the parenting game or a veteran, this book will help. As Beth says, “Think of it as a guide for parents that offers the financial facts of life for kids 3 to 23.”

And FYI, Beth is the real deal. In 2010, she was selected by President Obama to be a member of the President’s Advisory Council on Financial Capability, where she created The site attracted more than 1.4 million visitors and was adopted by the Consumer Financial Protection Bureau in 2016.

So whether you have kids, are planning on it or know someone with kids, I encourage you to check it out. It’s never too soon to start the money talk with your children.

For more financial literacy tips with Beth, you can connect with her on Twitter and Facebook.

Please leave us a rating or review in iTunes.

Better Off” is sponsored by Betterment.

Better Off” theme music is by Joel Goodman.

Ep. 005 - Fiduciary Standard Under Fire with Megan Leonhardt and Jack Otter

Fiduciary Definition, according to Merriam-Webster:

  1. a : held or founded in trust or confidence <a fiduciary relationship> <a bank’s fiduciary obligations>
  2. b : holding in trust
  3. c : depending on public confidence for value or currency <fiduciary fiat money>

Fiduciary is a weird legal word that has become a lightning rod from Wall Street to Washington DC. In a nutshell, fiduciary is the standard of care which requires financial professionals to put the interests of their clients’ first. Seems like a pretty obvious and basic principle, that should be the standard when someone is talking about your money, right?

Well, you may be surprised as to learn that the majority of the financial services industry has long been held to a lower standard, which was called “suitability.” Suitability meant that any financial product that was sold had to be appropriate for you, though not necessarily in your best interest. The problem is that most investors have been unaware of the different standards that have applied for all of these years.

Enter the the Department of Labor (DOL), which in the aftermath of the financial crisis — and in conjunction with the Obama Administration, began working on a way to incorporate elements of the fiduciary standard to those who provide retirement services to American investors.

After a lengthy comment period and lots of negotiation with the financial services industry, new DOL fiduciary rules are scheduled to begin implementation on April 10th. These rules are intended to help protect investors by requiring all who provide retirement investment advice to plans, plan fiduciaries and IRAs to abide by a “fiduciary” standard, putting their clients’ interest first. (There are exceptions to the new rules, which require advisers and financial institutions to follow certain procedures to avoid being in violation of the new rules.)

Financial service companies large and small had made big plans to comply with the new rules, but that was before the election of President Donald Trump. It is now widely expected that Mr. Trump, along with Congressional Republicans, may delay and perhaps kill portions of the proposed DOL rule.

As you can see it’s a complicated issue. It shouldn’t be, but it is. That’s why we brought in Megan Leonhardt from MONEY Magazine and Jack Otter from Barrons to try and help us make sense of it all. With implementation day rapidly approaching, if the government takes the position that the fiduciary standard is not important, you may want to ask yourself this question: If a broker or salesperson doesn’t want to put you first, why should you work with him?

I would love to hear your feedback on this thorny issue. You can always reach us via email at

Better Off” is sponsored by Betterment.

Ratings/reviews matter in the podcasting world, so if you have a free minute, please leave us one in iTunes.

Better Off” theme music is by Joel Goodman.

Ep. 004 - Build Your Dream Network with Kelly Hoey

I promised you that on the “Better Off” podcast, we would tackle uncomfortable, and even controversial, money and investing issues. And high up on the list of anxieties is trying to land a new job or move up the food chain in your existing workplace. Of course, it’s all about who you know and having connections.

As someone who has been called a “natural networker,” I wholeheartedly cling to that concept. In fact, according to the Bureau of Labor Statistics, 70% of all jobs are found through networking. And because it’s a new year, a time when people often make changes, especially career changes, we thought it was a good idea to talk to networking expert Kelly Hoey. Kelly’s new book, Build Your Dream Network: Forging Powerful Relationships in a Hyper-Connected World, has just been released and is perfect for anyone looking for networking and career advice.

We have all heard that networking can be an effective and important tool, but Kelly emphasizes creating meaningful connections, defining your goal and honing on those who can help you form a strategy for connecting. Some of her tips include:

  • Determine the most effective ways to connect with others so you don’t clutter your calendar with dead-end coffee dates and informational interviews
  • Synchronize networking efforts with your digital outreach
  • Turn “closed door” conversations into strong personal relationships and business opportunities
  • Eliminate FOMO by keeping your networking efforts focused

We also talk about how the rules have been rewritten now that we live in a digital world where our lives are dominated by Facebook, Twitter and apps.

The book also includes a series of Q&As with some of the best networking experts in the business who share some invaluable advice based on their successes and failures.

Better Off” is sponsored by Betterment. For more networking tips, connect with Kelly on Twitter, Facebook and her website.

As always, ratings and reviews matter in the podcasting world, so if you have a free minute, please leave us a rating in iTunes. Thank you!

Better Off” theme music is by Joel Goodman.

Ep. 003 - Misleading Numbers in Elections and Investing with Harry Enten

Young. Check.

Ivy League educated. Check.

Obsessed with statistics. Check.

Obsessed with politics. Check.

A rising star in the media world. Check.

Yep, that pretty much describes this week’s “Better Off” podcast guest.

As promised, we tackle uncomfortable, and even controversial, money and investing issues, but on this episode, we are wading into the choppy waters of politics, with Harry Enten, senior political writer and analyst for FiveThirtyEight. If you’re not familiar with the site, it’s the brainchild of statistician guru Nate Silver who gained recognition in 2008 after correctly predicting the outcomes in 49 of the 50 states in the presidential election.

With the presidential inauguration upon us, we thought it made sense to talk to someone about the recent race, more specifically the numbers behind it, and how so many people got it wrong.

What were the warning signs that so many missed? What did Hillary do wrong? Was it all about the economy or were there other factors? Did the third party candidates have an impact?

Harry breaks down the election/forecasting/statistical terminology we’ve been bombarded with over the past year or so. What is probability and what does it mean? How about margin of error? What about sample errors? Are polls perfect or are they just a tool?

As you’ll hear, politics was the main theme, but we also talked about Harry’s background and his love of sports and weather. That’s right, weather. This guy loves a good snowstorm. So much so that it played a role in picking a college.

I think you’ll really enjoy the interview. It was very fun and informative, definitely one of my personal favorites. Harry Enten is a name you will be hearing more and more of in 2017. We just hope he remembers us little people.

Better Off” is sponsored by Betterment and if you like what you hear, follow and connect with Harry on social media. You can find him on Twitter and Facebook.

And one more thing…ratings and reviews matter a lot in the podcasting world. So if you have a free minute it’d mean a lot if you can rate me in iTunes. Thank you!

Better Off” theme music is by Joel Goodman.

Ep. 002 - Fail More, Reinvent Yourself with James Altucher

So here you are, listening to, or about to listen to the second episode of the “Better Off” podcast. Like you, I love podcasts. I subscribe to many, probably too many. But that’s how I found our guest this week, the one and only James Altucher.

Last spring, I was walking on an isolated Long Island beach, picking up trash on Earth Day, listening to his podcast, The James Altucher Show, and was so blown away that I said out loud, “I need to interview this guy!” And that’s exactly what I did. After getting in touch via Twitter, James was a guest on my radio show and we’ve been pals ever since, hence his appearance on the podcast today.

Aside from hosting his own successful podcast, James is also a serial entrepreneur and investor. How smart is this guy? As you’ll hear right off the bat, he’s smart enough to know that when it comes to investing, he’s not smarter than the market, which is why these days, he prefers the robo-advisor model, which essentially prevents him (and the rest of us) from making stupid decisions. Makes sense since he’s a lover of technology. One day we’ll get his thoughts on virtual reality and artificial intelligence.

James is also an accomplished author with more than a dozen books under his belt. You can now add another one to the list with the recently released Reinvent Yourself. More than anything else, that’s exactly what initially drew me to James: his ability to continually reinvent himself, as well as his authenticity and his willingness to talk about it. He really is an open book. And he’s not just talking about his successes, of which he’s had many, but also his failures, of which he’s probably had more. This guy has made millions and lost it all, more than once! More than twice! Yet he somehow continues to reinvent himself and come out on top.

As you hear this interview I suspect you may think, “How can I be more like this guy?” If so, you should definitely check out his book, Choose Yourself and his newest release, Reinvent Yourself.

Better Off” is sponsored by Betterment and if you are as drawn to James as I am, you can follow and connect with him on Twitter and Facebook.

And one more thing…ratings and reviews matter a lot in the podcasting world. So if you have a free minute it’d mean a lot if you can rate me in iTunes. Thank you!

Better Off” theme music is by Joel Goodman.

Ep. 001 - New Year's Resolution: Become a Millionaire with David Bach

How does it feel to have nine consecutive books make the New York Times bestsellers list? Or to be on the Oprah Winfrey Show six times? Well, I have no idea, but our “Better Off” guest, David Bach, does!

Let me back up…this is the first-ever episode of “Better Off” where I tackle sometimes uncomfortable — and even controversial — money and investing issues. For the show premiere, I talked with David Bach, who has written eleven national bestsellers, with over seven million books in print. He’s best known for “The Automatic Millionaire.” It was so popular the first time around that he just released an expanded and updated version.

Of course, there’s no secret recipe to becoming an automatic millionaire. There’s no magic formula. It’s something that takes time, work and discipline. If it were that easy we’d all be millionaires…and Mark probably wouldn’t be my producer. You’ll get to know Mark in subsequent episodes. He’s the guy that makes the show appear in your feed every week.

As you’ll hear, I don’t agree with David that skipping a latte a day will help you become rich, but we also discuss many topics in the book upon which we both agree—perhaps none more important than becoming an “automatic investor.” Research shows that we have more positive outcomes when we take emotions and self-discipline out of the equation and put our financial lives on autopilot. That may be the biggest takeaway from the book. Whether it’s a retirement plan at work, an IRA, or a service such as Betterment, set it, forget it and let the magic of compounding interest go to work.

It’s the beginning of a new year, a time when we reassess our financial situations and maybe even make some resolutions. Listen to this podcast, read the book and I have no doubt you’ll pick up some useful tips that will help you achieve your goals in 2017.

Better Off” is sponsored by Betterment. If you like what David Bach has to say, you can follow and connect with him on social media. He can be found on Twitter and Facebook, as well as his website.

Better Off” theme music is by Joel Goodman.

Welcome to the Better Off Podcast