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By Erin @ Team Afford Anything

#240: 10 Questions to Master Successful Investing, with David Stein

Do you know what it takes to be a successful investor?

Can you name the three drivers of asset class performance?

Are you aware of the upsides and downsides of each investment that you hold?

Not having the answers to these questions could leave your portfolio exposed to major risk.

That’s why David Stein, today’s guest, wrote an appropriately titled book: Money For the Rest of Us. His book outlines 10 thought-provoking questions to ask before making any investment decision.

David, a two-time guest on the show, was the Chief Investment Strategist and Chief Portfolio Strategist at Fund Evaluation Group, a $70 billion investment firm. While there, he co-founded the firm’s $2.2 billion asset management division and developed its investment philosophy and process as the lead portfolio manager.

In this interview, David discusses the 10 questions outlined in his book:

What is it?
Is it investing, speculating, or gambling?
What’s the upside?
What’s the downside?
Who’s on the other side of the trade?
What’s the investment vehicle?
What does it take to be successful?
Who’s getting a cut?
How does this investment impact your portfolio?
Should you invest?

Whether you’re new to investing or consider yourself an advanced investor, David has an asset allocation approach that can save you from the expensive mistakes investors often make.

Here’s how to think through each of these 10 questions and improve your investment decision-making process.

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By Paula Pant

#239: Ask Paula – Should I Put My Student Loans in Forbearance? Should I Buy a Vacation Rental in the Mountains? and More

Lo is in a good spot with her career, but she’s struggling with a ton of student loan debt, and consequently, credit card debt. What should she do to manage it?

Anonymous wants to know how to set up a backdoor Roth IRA.

Eric and his wife own a property in Savannah, GA that brings in more money as an Airbnb than a traditional rental. They want to invest in more properties and are wondering if this model is the best path to take.

James wants to own a vacation rental in the Vermont mountains that he can use when it’s vacant. What features or qualities would make a profitable vacation rental? What red flags should be on his radar?

Ayesha is looking at buying a rental property that has a partial HUD claim on it. What kind of complications should she anticipate? Or should she let this property go completely?

Shelbi and her husband own a rental property that they purchased for $178,000 that’s now valued at $300,000. They’re looking at a multitude of options – sell it, move into it, or keep it. What’s best given their FIRE goal?

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By Erin @ Team Afford Anything

#238: How to Stop Making So Many Money Mistakes, with Jeff Kreisler

Have any of these thoughts ever crossed your mind?

If I had more willpower, I’d achieve my financial goals.

I’m doomed to fail with money.

Budgets suck. They only show me what I did wrong and make me feel horrible.

If so, you’re not alone.

It’s not that you lack willpower.

It’s not that you’re doomed to fail with money.

It’s not that you’re a horrible person for blowing your budget.

It’s that you’re human.

And humans make emotional decisions all the time. Decisions that often defy logic.

But making emotional decisions doesn’t have to be a financial death sentence. Money management is a skill, which means we can improve.

When we understand the “why” behind our decisions, coupled with the marketing tactics that retailers use, we can guard ourselves against cognitive biases and sales strategies.

That’s what today’s guest is here to discuss.

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By Paula Pant

#237: Ask Paula and Joe – Should I BUY a Business, Instead of Starting One?

Katie wants to know how to purchase a business that’s already cash-flow positive. What indicators can she look for?

Rob will retire from the military with an inflation-adjusted pension. Does he need a bond allocation in his investment portfolio?

Brian conquered a large sum of credit card debt, but still has student loan debt and a mortgage. Should he pay off his student loans, refinance them, or refinance his mortgage?

Jeff is curious about the pros and cons of investment apps. When should you use them?

Another Kati (without an e!) wants to live a healthy and wealthy life before she’s 70. Where should she allocate her savings so she can retire early?

We answer these five questions in today’s episode.

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By Erin @ Team Afford Anything

#236: How We Saved $1 Million and Retired at 31 and 32, with Kristy Shen and Bryce Leung

Can you imagine living on 44 cents a day?

Kristy Shen doesn’t need to imagine it. She lived it.

Kristy grew up in rural China, where 85 percent of the population lived in abject poverty.

When she was eight, her family emigrated to Canada. In Kristy’s eyes, her family’s newfound ability to buy a can of Coca-Cola meant that they had “made it.” Kristy loved her Coke can so much that she turned it into a toothbrush holder.

Years later, Kristy met Bryce Leung at university, where they were classroom lab partners. They married, settled in Toronto and started saving for a downpayment on a house.

When their down payment savings hit $500,000, they started to question the wisdom of dumping their money into an expensive personal residence.

Fueled by curiosity, they stumbled down the financial independence rabbit hole. After countless hours of research and number-crunching, they ditched their plan to buy a house and invested their $500,000 into the stock and bond market. Around seven years later, their net worth reached $1 million.

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By Paula Pant

#235: Ask Paula – Sooo … I Quit My Job. What Type of Business Should I Start?

Anna has made the leap to self-employment … but what’s next? She lives in the Bay Area and she’s trying to choose between five business ideas; she needs to make enough money to stay in her high-cost area.

Doug recently won $9,000 from an online poker side gig and is wondering how best to use the funds: pay off high-interest student loan debt, or keep it to increase his poker earning potential?

Alex and his partner want to househack a single-family property with a mother-in-law suit. What should they consider as far as zoning goes?

Darrell is on track to retire in two years at age 55 and wants to know what he should do with his primary residence. Should he rent it out? Or should he sell it and use the profit to invest in rental properties? Or use the profit to buy his retirement home?

Mara is curious about 1031 exchanges. She has equity in a rental property that she’d like to harvest, but she wants more information before making the move.

Michael and his wife are struggling with competing goals. They want to invest in real estate, but they also want to move into an apartment closer to work to reduce their long commutes. Should they sell their home and invest the equity into a rental property, or should they take a HELOC on their home instead?

I answer these six questions in today’s episode. Enjoy!

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By Paula Pant

#234: 26 Easy Moves to Improve Your Finances in 2020

Last year, I issued the One Tweak a Week challenge to this community.

The Afford Anything team and I released a free book outlining 26 easy actions that improve your finances and life. We choose simple actions that you could complete in one hour or less (some are as quick as five minutes), which added together amount to major change.

We challenged this community to take one action per week for the first 26 weeks (six months) of the year, and we sent a weekly reminder email, each Sunday, to anyone who downloaded the free book.

We heard incredible feedback. Several people told us that One Tweak a Week helped them make huge improvements to their financial life.

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By Paula Pant

#233: Ask Paula – How Can I Retire in 12 Years?

Deepak is considering downsizing his family’s home, but wants to know if the savings are worth the transaction costs he’ll have to pay.

Anonymous and her husband hold $900,000 worth of privately-owned company stock. How should they plan for handling this money?

Shelby is 25 years old and works for a company that awarded her restricted stock units. What should she do with these? Additionally, she traded in a 2013 Prius for a 2018 Subaru, for which she now owes $19,000. Should she sell it for a used vehicle or stick it out?

Katelyn is interested in learning more about annuities. What should she know in order to make an informed decision?

Max FI and his wife want to retire in 12 years. How should they invest to achieve this?

Anonymous’s former employer offered a Roth and Traditional 401k, and his new employer only offers a Traditional option. How should he rollover his former Roth 401k?

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By Paula Pant

#232: How to Get a Debt-Free Degree, with Anthony ONeal

Anthony ONeal dug himself into $35,000 of debt by the time he turned 19.

His debt was unnecessary. He didn’t need this money to cover tuition or books; his father’s military GI Bill covered his college expenses.

Anthony took out discretionary loans — mostly in the form of credit card debt — to buy luxuries like furniture. Yes, furniture.

When he couldn’t keep up with the payment, lenders repossessed his couch.

He repaid his debt, vowed never to spend beyond his means, and became a crusader for a debt-free lifestyle. Today he’s the bestselling author of Debt-Free Degree, a book that teaches parents how to help their children graduate from college debt-free. He’s also the author of Graduate Survival Guide, along with Rachel Cruze.

Anthony joins us on the show to discuss how parents and students can defray or eliminate the cost of a college education.

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By Paula Pant

#231: Ask Paula – How Can I Get My Spouse Interested in Frugality?

Avie is looking for help in deciding between two good options: paying off a rental property, or funding a retirement account. Which option should she go with?

Sofia’s parents have been living with her for the past few years, but her job is taking her out-of-state. How should she transition her home to a rental property for her parents?

Lisa has a question about HSAs: when do you actually fund your HSA account?

Jim grew up frugally and has no qualms with this lifestyle, but his wife doesn’t share his views. He’s curious about how he can bring her to the frugal side, and how he can approach opening her eyes to starting a business so that she can stay at home with their kids.

Candice asks: what are your thoughts on online real estate investment crowdfunding platforms?

Kristen has a mortgage on her primary residence and a rental property. They’re both at similar interest rates. Which one should she focus on paying off first?

I answer these questions in today’s episode of the show. Let’s dive in!

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