Jill on Money Radio Show: Can I Quit My Job?

With things around the country starting to resemble something normal, many employers are calling workers back into the office, and after many months of working from home, many aren't so eager to go back, including our first caller.

For our second call we do some short and long-term planning with a couple in their 30s who are about to welcome their second child.

Our guest in hour two, Dorothy A. Brown, became a tax lawyer to get away from race. As a young black girl growing up in the South Bronx, she’d seen how racism limited the lives of her family and neighbors. 

Her law school classes offered a refreshing contrast: Tax law was about numbers, and the only color that mattered was green. But when Brown sat down to prepare tax returns for her parents, she found something strange: James and Dottie Brown, a plumber and a nurse, seemed to be paying an unusually high percentage of their income in taxes. When Brown became a law professor, she set out to understand why.

In her recently released book, The Whiteness of Wealth, Brown draws on decades of cross-disciplinary research to show that tax law isn’t as color-blind as she’d once believed. 

She takes us into her adopted city of Atlanta, introducing us to families across the economic spectrum whose stories demonstrate how American tax law rewards the preferences and practices of white people while pushing black people further behind.

From attending college to getting married to buying a home, black Americans find themselves at a financial disadvantage compared to their white peers.

The results are an ever-increasing wealth gap and more black families shut out of the American dream.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Where to Park Excess Cash?

With an extra $1500 or so each month, where should that money be going? Sounds like a simple question, right? As you’ll hear in my conversation with our caller, things always get a bit more interesting when you actually join me on the show.

More of the usual in hour one as we mix in a handful of emails around the caller.

In the second hour we're joined by Ellen Bennett, author of Dream First, Details Later: How to Quit Overthinking & Make It Happen!

As a 24-year-old line cook, Ellen Marie Bennett couldn't stand the kitchen staff’s poorly designed, cheaply made aprons. So when her head chef announced he was ordering a new batch, she blurted out, “Chef, I have an apron company” even though she had no company, no business plan, just a glimmer of a design idea and a business license. 

Through hustle and a willingness to leap into the unknown, time and time again, she built that first order into a multi-million-dollar company called Hedley & Bennett, making aprons and kitchen gear worn by many of the world’s best chefs and home cooks everywhere.

Dream First, Details Later shares Ellen's journey and her forged-in-the-fire personal playbook for starting before you stop yourself. If you've ever imagined doing something and immediately thought, "that's impossible," or "I wouldn't even know where to start," or "I'm not qualified to do that," in these pages, you'll learn how to shove aside your inner worrier and launch into action. 

This honest and bold illustrated book will be like having Ellen, your personal hype woman, there with you, all the while yelling, "Don't stop! You got this!"

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Can I Retire at 58?

Let’s kick off the first weekend of June with a very common question. Can I retire early? In this case, it’s a 43 year old who is currently socking away a ton of money in hopes of retiring at 58, or at least being able to slow down and have more options. Is it doable?

I am often asked about the best retirement plan options for entrepreneurs and sole proprietors.

There's a lot of choices out there, and it's not always so easy to determine which plan makes the most sense, that's why in hour two we're glad to welcome back Michael Goodman for a little small business bootcamp!

As the president of Wealthstream Advisors in New York City, Michael knows firsthand what it's like to run a small business.

We'll touch on a variety of topics, including which retirement plan is the best choice for your situation.

Among the options discussed:

  • Individual Retirement Account (IRA): You can choose a traditional IRA, where you pay taxes in the future or a Roth, where you pay taxes today.

  • Simplified Employee Pension (SEP-IRA): This is a good option for those who have up to 25 employees and want to offer a retirement benefit that is easy to operate.

  • Savings Incentive Match Plan for Employees (SIMPLE IRA Plan): SIMPLE plans were aimed at slightly larger small business owners (usually up to 100 employees), who wanted to provide employees a way to save for retirement.

  • Solo 401(k) plan: Alternatively referred to as an “individual 401(k)” or “uni-401(k),” this plan is geared to small business owners who have no employees (other than a spouse) and have the capacity to sock away a lot of dough.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: What to Do With Monthly Savings?

Happy Memorial Day weekend! Can you believe it? Five months already in the books! Who knows what the next seven will bring, but one thing I do know, we’ll still be here answering your questions.

Here’s what I like to call a good problem to have. A few thousand extra dollars each month and you’re not quite sure what you should be doing with the surplus cash. That’s the conversation with our caller in the first hour.

Happy 529 Day, a day when states try to boost interest and participation in 529 education savings programs with various incentives.

To mark the occasion we’re once again joined in hour two by Brent Weiss, co-founder and Head of Planning at Facet Wealth, the Jill on Money sponsor for 2021.

With Brent in the co-pilot chair, we touched on several topics, including:

What is a 529? A tax-advantaged savings plan designed to encourage saving for future education costs. 529 plans are sponsored by states, state agencies, or educational institutions and are authorized by Section 529 of the Internal Revenue Code.

What’s the tax benefit of a 529 plan? Withdrawals for qualified higher education expenses and earnings in the account are not subject to federal income tax and, in most cases, state income tax. Additionally, some states offer residents of the state specific incentives, like the ability to deduct contributions from state income tax or a matching grant.

What does a 529 plan cost? Fees and expenses vary widely from plan to plan and can include start-up fees, maintenance fees, or sales charges. In general, advisor-sold plans cost more than direct-sold plans.

What happens if my kid doesn’t go to college? Most states allow you to tap the accounts for other children in the family or even for the parents. Those withdrawals that are not used for qualified higher education expenses will be subject to state and federal income taxes and an additional 10 percent federal tax penalty on earnings.

Are 529 plans only for college? Americans can now withdraw funds tax-free from 529 plans to pay for K-12 tuition and other eligible expenses at private and religious schools, up to $10,000 per year. But there’s a caveat: Not all states will conform to the new federal rules. That means before you pull money, be sure to double check with your state.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Strategies in Retirement

One week away from Memorial Day weekend. Hard to believe, right?

Speaking of time passing by, getting to retirement can often seem like it’ll take forever. But once you’re there, many questions can often pop up, such as whether or not it makes sense to start doing Roth conversions or which retirement accounts to tap first. That’s the gist of our call in hour one.

In hour two it’s time for a deep dive on the spring housing market.

Joining us this weekend is Maria Fregosi, the Chief Investment Officer at Homepoint Financial.

Where is the housing market going next? Despite the fact that we are coming to the end of the pandemic with accelerated vaccinations, many companies have announced that employees working from home may continue to do so permanently. 

That may allow some to seek out more affordable areas like Austin, Charlotte, Miami, and Nashville. 

Some smaller cities have launched cash initiatives, home buying allowances, tax credits and money toward local goods and services to induce pandemic movers to relocate there. 

If you are in the market to buy, you will need to run the basic numbers, including mortgage principal and interest, homeowners' insurance, and taxes. Add a line item for upkeep and maintenance, depending on the age of the house and its condition, factor in 1-3 percent of the purchase price annually. 

And for the transaction itself, don’t forget about closing costs, which averaged more than $6,000 last year. It’s easy to gloss over things like mortgage loan application and appraisal fees, the title search and insurance, as well as legal and recording fees, because they seem to be built into the legal process, but you should ask for discounts along the way to see if you can push them down.

Finally, even if the numbers appear to work, consider whether buying could preclude you from addressing other important financial issues in your life, like paying down student loans or saving for retirement. Just because a lender will fork over the dough, doesn't mean you should take it.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: A Financial Start Over

Whew, a pretty rough week on Wall Street, eh? Hopefully everybody stayed calm and carried on :)

Hour one this week is the usual mix of calls and emails.

Nothing like a fresh divorce to cause you to re-evaluate your financial situation. Hey, at least our caller cut her losses while she’s still young, so it’s really more of a celebration.

In hour two, we're calling all recent college graduates!

You've landed a job. Now what?

To help answer that question, we're joined this weekend by Gorick Ng, author of The Unspoken Rules: Secrets to Starting Your Career Off Right.

No one tells you how to navigate your first day in a new role. No one tells you how to take ownership, manage expectations, or handle workplace politics. No one tells you how to get promoted.

The answers to these professional unknowns lie in the unspoken rules, the certain ways of doing things that managers expect but don't explain and that top performers do but don't realize.

The problem is, these rules aren't taught in school. Instead, they get passed down over dinner or from mentor to mentee, making for an unlevel playing field, with the insiders getting ahead and the outsiders stumbling along through trial and error.

Until now.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Crypto Jackpot

Happy Mother’s Day weekend!

What better way to celebrate than with a story about hitting the crypto jackpot?!

The good news is that our first caller hit the crypto jackpot at the ripe young age of 40! The bad news is that his portfolio is now completely out of whack. What to do, what to do??

No guest this week in hour two. Instead we mixed in another call and then answered a handful of emails.

We’ve given up on trying to clear out the inbox. We’re just going to do the best we can. What I like to call a good problem to have.

Have a money question? Email me here.

Please leave us a rating or review in Apple Podcasts.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Roth or Pre-Tax?

Surprise, surprise, both our callers in hour one have Roth related questions.

Honest to goodness, anything related to Roth money is by far the most popular question we receive.

Should you be using your traditional 401(k) at work or should you be using the Roth 401(k)?

Should you be doing backdoor Roth conversions?

You get the point. We’ll also mix in the usual handful of other retirement related questions.

Risk: success requires risk, risk that stands firmly on the platform of integrity.

Reward: integrity inspires reward, generosity toward those who helped you succeed.

Repeat: generosity fuels repetition, helping others to forge their own way forward.

These are the lifelong tenets of Eric Gleacher, the Marine Corps officer and investment banker who, along with a handful of others, dominated the Mergers & Acquisitions industry in the latter half of the twentieth century and transformed the face of American business.

He also happens to be our guest this week in hour two to discuss his recently released book, Risk. Reward. Repeat.: How I Succeeded and How You Can Too.

Risk. Reward. Repeat. chronicles his compelling journey: from a profoundly isolated childhood to the hardcore leadership lessons of the Marine Corps, to Lehman Brothers and Morgan Stanley, to his own firm, going toe-to-toe with the giants of Wall Street.

Gleacher's book puts today's culture of hype, tricks, and life-hacks to shame with its simple, timeless formula: be yourself, tell the truth, lead by example, do your best, own your mistakes, work hard, take risks, earn your success, and pay it forward.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: How to Invest Extra Cashflow

Happy last weekend of April!

Talk about a lucky duck, our first caller this week has around $5,000 each month in extra cashflow. What should she be looking to do with the surplus cash?

Next up we spent some time trying to fix an IRA mess. IRAs and Roth IRAs have all sorts of rules, and if you screw something up, it could be a real mess. But like most messes, they can usually be cleaned up :)

In hour two we’re once again joined by Brent Weiss, co-founder and Head of Planning at Facet Wealth, the Jill on Money sponsor for 2021.

April can only mean one thing in the personal finance world, it’s Financial Literacy Month, so that’s the gist of our conversation.

The global economy has become so complex that the gap between what people know about economics and personal finance, and what they need to know, is widening every day.

Americans are increasingly responsible for their financial future; yet an alarming number lack even basic economic awareness.

Compounding the problem, many parents are ill-equipped to instruct their children in economics and personal finance, and teachers, too, are often unprepared to impart this essential knowledge.

That’s why more than ever we need to be passionate about educating young people about an economy they will work in, benefit from, and ultimately, inherit.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Should I Ditch My Whole Life Policy?

Happy middle of April! Before you know it we’ll be celebrating Memorial Day :)

This week we have a couple calls in hour one as well as a handful of emails.

The first call is a conversation about company stock and just how much is too much to be keeping in your portfolio.

The second call is about a whole life policy and whether or not the caller, a single guy in his 30s, should keep or ditch it.

In hour two, no time like the present to start thinking about that side hustle you've always dreamed about. If a global pandemic doesn't get you motivated, I'm not sure what will.

Do you have to be an “entrepreneur,” replete with a big, fat business plan in hand, to make a little extra cash on the side?

What if I told you that in 27 days you can come up with an idea, implement it, and potentially start making some extra income on the side?

That is what you call a side hustle, which also happens to be the title of a book from Chris Guillebeau, who's nice enough to join us this weekend.

While the thought of quitting your day job to pursue a business of your own may be intoxicating and even escapist, it may also be a bit unrealistic. Most of us can’t just up and quit a job that delivers a regular paycheck and benefits, to boot.

But what if you could quickly and easily create an additional stream of income without giving up the security of a full-time job? Enter Chris and the side hustle.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Am I Okay in Early Retirement?

No guest this week, just a bunch of emails and a couple callers.

Before the month is out, we’ll be joined again by Brent Weiss from Facet Wealth as we talk some FinLit, an always appropriate topic, but even more so in April as it’s National Financial Literacy Month.

For our first call, there’s nothing like planning for retirement as a young couple with half a million dollars in outstanding student loan debt. You know what's even crazier? I'm kind of okay with it!

For our second call in hour two, we hear why the magic of compound interest is a beautiful thing to watch. Start early, stay consistent, and voila, you end up with a boatload of money come retirement.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: What's the Priority?

Happy April!!! The light at the end of the tunnel seems to only be getting brighter and brighter as we kick of the second quarter of 2021.

The real estate market is busy, busy, busy, so it’s only appropriate that our first call this week is related to investment property.

After that we help out a young couple trying to figure out what the financial priority should be. Overall they’re in pretty good shape, just need to clean a few things up.

In hour two I'm so excited to welcome back Cal Newport to the show, who joins us to talk about his latest book, A World Without Email: Reimagining Work in an Age of Communication Overload.

Modern knowledge workers communicate constantly. Their days are defined by a relentless barrage of incoming messages and back-and-forth digital conversations, a state of constant, anxious chatter in which nobody can disconnect, and so nobody has the cognitive bandwidth to perform substantive work.

There was a time when tools like email felt cutting edge, but a thorough review of current evidence reveals that the "hyperactive hive mind" workflow they helped create has become a productivity disaster, reducing profitability and perhaps even slowing overall economic growth.

Equally worrisome, it makes us miserable. Humans are simply not wired for constant digital communication.

We have become so used to an inbox-driven workday that it's hard to imagine alternatives.

But they do exist.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Roth Conversion Strategy

What’s the best strategy when considering to convert a traditional IRA to a Roth IRA? That’s the gist of our chat with Matt midway through hour one. And you’ll also hear why he’s incredibly grateful just to be able to ask the question.

Mixed in around the call we have more of the usual emails.

Today we think statistics are the enemy, numbers used to mislead and confuse us. 

Our guest in hour two, Tim Harford, says that's a mistake. 

In his latest book, The Data Detective, Harford says we shouldn’t be suspicious of statistics, we need to understand what they mean and how they can improve our lives: they are, at heart, human behavior seen through the prism of numbers and are often “the only way of grasping much of what is going on around us.” 

If we can toss aside our fears and learn to approach them clearly, understanding how our own preconceptions lead us astray, statistics can point to ways we can live better and work smarter.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Am I Still on Track?

Spring is officially here!

And with it comes a beaming light at the end of a long, dark tunnel. Thank goodness!

That said, let’s not forget about all those who’ve been impacted by the pandemic, even though some are certainly doing better than others, as you’ll hear with our caller and emails.

In hour two we’re once again joined by Brent Weiss, co-founder and Head of Planning at Facet Wealth, the Jill on Money sponsor for 2021.

Spring can only mean one thing, peak season for the real estate market.

Brent joined us to talk about all the things that go into making a home purchase, as well as credit scores, which play a huge factor in determining what kind of interest rate you get.

As a reminder, if you’re interested, Facet Wealth is a financial service firm that believes in achieving your financial goals with a dedicated CFP® at an affordable price.

Whether it’s retirement planning, education planning, asset management, insurance or estate planning, Facet wants to show you what is possible with the next generation of financial life management.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Non-Traditional Retirement Planning

I know the whole goal of this program is to take the mystery out of your finances, but sometimes it’s easier said than done, especially when you’re dealing with a non-traditional situation, and that’s the case with our caller this week.

But don’t worry, we address plenty of traditional situations by answering a bunch of your emails!

Stimulus payments have been a critical lifeline for many Americans during the coronavirus crisis. But what if you didn’t receive the full amount due to life changes such as a new baby or lower income? Thankfully there’s a way to solve this, in the form of a recovery rebate credit.

The recovery rebate and your stimulus payments are actually one in the same. It’s just that the recovery rebate credit is paid as part of filing your return.

Joining us this week to help make sense of it all is Kathy Pickering, the chief tax officer at H&R Block.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Did We Make a Financial Blunder?

Happy March!

We get a lot of hate mail when we have people on the air who have money. As if we’re not supposed to talk to such individuals? It’s a completely absurd thought process.

Whether you have a lot of money or a little, nobody is immune to financial missteps along the way. Hence our caller in hour one.

In hour two we're joined by Ilir Sela, founder and CEO of Slice.

Since 2010, Slice, the easiest way to order pizza online, has been all about connecting hungry customers with the great pizza restaurants around them.

Today, more people than ever are experiencing the benefits of the free and easy Slice ordering applications with access to thousands of independent pizza menus.

For hungry customers it provides a quick and easy way to place orders with the best local pizza restaurants. For pizza restaurants it provides an effortless and complete online ordering solution, fully interactive menu and marketing services to attract new customers.

Enjoy!

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Financial Checkup and Bitcoin

Adding a baby to the mix sure seems like a good enough reason to call Aunt Jill and get a status check on your current financial situation. All I’m going to say is that with a new baby, the estate planning better be taken care of!

As is the norm, we’ll also be answering a handful of emails in hour one, this the last show of February! And so begins the beginning of the end of Q1. Got it?

In hour two we’re doing a deep dive on bitcoin. This ran recently on the podcast but we figured we better run it right away on the radio show before bitcoin either tanks or hits 100k.

So we're joined once again by Dan Roberts, senior writer at Yahoo Finance and a total crypto geek who has been covering the wild ride from the beginning.  

Bitcoin (BTC) started 2020 at $7,200. It ended the year at nearly $30,000, up 296%.

The surge continued full-steam into 2021. It took bitcoin 10 years in existence to reach $20,000 on most exchanges, on Dec. 15. 

Then it took just 17 days to reach $30,000.Bitcoin broke through $30,000 for the first time on Jan. 2, then climbed to $32,000 just hours later. On Jan. 5, it broke $35,000, and on Jan. 7, it hit $40,000. Now it seems to be hitting $50,000 or higher on a regular basis.

Crazy, right? Before you decide to dip your toes in the bitcoin waters, please do yourself a favor and first listen to this episode with Dan.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Mortgage or No Mortgage?

Semi-retired and looking to buy a new house. The big question is whether or not to take out a mortgage or pay cash? That’s the gist of our call this week as we chat with Ryan from Seattle.

The rest of hour one was trying to clean out the inbox. Haha, yeah right. We’ve got thousands of emails, and all I can say folks is that we’re doing the best we can.

What could be more basic than preparing your taxes? After a tumultuous 2020, tax season is officially open, a few weeks later than years in the past. The deadline to file and pay any tax owed reverts to April 15th, after last year’s COVID-19 related extension.

By now, you should have received most of your tax preparation documents (W-2s, 1099s, as well as bank, investment, mutual fund and mortgage company documents).

If you didn’t learn the lesson of electronic filing last year, this is the year to dump the paper. After all, those who had electronic files with the IRS got those stimulus checks faster than those who had to wait weeks and sometimes months for their money.

Additionally, be sure to choose direct deposit, which is “the safest, most accurate and fastest way to get a refund,” according to the IRS.

Because of all the various changes that went into effect last year as the pandemic unfolded, this tax season could be a tricky one.

To help us break it down, we're joined by the one and only Ed Slott, the ultimate tax guru and founder of IRA Help.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Financial Help for Recent Widow

Welp, so much for my Super Bowl prediction! I suppose I should stay in my lane and focus on what I do best, helping you guys navigate your financial lives.

We start this week by answering a handful of emails and then taking a call from Margaret, a recent widow.

Dealing with a loss is hard enough, then mix in trying to navigate the finances, and things can quickly become too much to handle.

In hour two we’re once again joined by Brent Weiss, co-founder and Head of Planning at Facet Wealth, the Jill on Money sponsor for 2021.

Since it’s Valentine’s Day weekend, we figured it was a good time to bring Brent back on and chat about all things love and money :)

As a reminder, if you’re interested, Facet Wealth is a financial service firm that believes in achieving your financial goals with a dedicated CFP® at an affordable price.

Whether it’s retirement planning, education planning, asset management, insurance or estate planning, Facet wants to show you what is possible with the next generation of financial life management.

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.

Jill on Money Radio Show: Is My Advisor Charging Too Much?

Happy Super Bowl weekend! Let’s go Chiefs, in with the young, out with the old :)

We start the show with Vicky from New England who’s wondering if she’s being charged too much by her financial advisor. And did she get suckered into purchasing a needless insurance policy?

We finish up the hour by answering a few emails.

GameStop has been all the rage lately, but I really think it’s a story that goes beyond finance and into tech.

And when the worlds of finance and tech collide, my man, Jeff Bakalar, is my go to source! (And I'm his go to source, which is why he had me on his CNET show to help explain the concept of short selling. You can check it out here.)

You've heard Jeff on the pod before, but in case you've forgotten, Jeff is the editor-at-large at CNET, and a total tech geek who's with us this weekend to help explain what in the world happened this week with GameStop and Reddit.

GameStop, the brick-and-mortar video game seller that many presumed was destined to the dustbin of retailers, started to attract enormous interest from individual investors on Reddit, a message board where community members create content, submit links, and comment on specific topics (subreddits).

The GameStop believers touted the upside as early as mid-2019, after Michael Burry (the guy featured in “The Big Short,” who bet against the housing market in the mid-2000’s) had amassed a big position in the company. The chatter continued into 2020, when GameStop was trading at about $4/share.

GameStop saw the culmination of the mother of all short squeezes on January 27th, when the stock soared by more than 130 percent to nearly $350/share, almost ten times the value from the prior week and putting its year-to-date return at 900 percent.

And remember folks, those who are investing in volatile stocks like GameStop should be prepared for a wild ride, and should only risk what they can afford to lose. 

Have a money question? Email me here.

"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.