Investing, Student of the Market
Ryan Weiser
Student of the Market - May 2025
Student of the Market - May 2025

Financial Planning

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Should You Purchase a Second Home with Friends?

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Should You Purchase a Second Home with Friends?

Owning a home away from home can add some significant value to your portfolio and your ROL. A second home can be an escape, a change of scenery, a place to immerse yourself in specific interests, sports, or hobbies, or the focal point of meaningful get-togethers for generations to come.

But if you can't make owning a second home work on your own, should you consider sharing the costs, responsibilities, and space with another family?

While the logic might seem compelling, sharing real estate will add a complex business arrangement to your friendship. Make sure you and your prospective co-owners talk through these three important issues.

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What Does Financial Independence Mean to You?

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What Does Financial Independence Mean to You?

According to a recent poll of 2,000 U.S. adults, "financial independence" equates to earning $94,000 per year, or about $20,000 more than the median income in 2023.

Some folks might feel like they're just a promotion or two away from achieving that kind of independence. Others might not feel like $94,000 is enough to feel truly free. And still others might wonder how they'd ever spend that much money in the first place.

That's because true financial independence isn't a number. It's feeling confident enough in your money to do things that will improve your Return on Life, such as:

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The Importance of Balancing Saving and Spending for Doctors and Dentists

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The Importance of Balancing Saving and Spending for Doctors and Dentists

Doctors and dentists often find themselves on very different $Lifeline trajectories than friends and family members who don't work in health care. While many folks in their early 20s might be earning real money at their first jobs or getting married, you might still be in school. Your friends might be buying houses while you're still working through a low-paying residency. And once you're an M.D. or D.D.S., it can be very tempting to treat that high salary you've worked so hard for like it's a jackpot.

Use these three tips to balance responsible spending and saving so that you can earn more Return on Life throughout your career…

What March Madness Can Teach Us About Your Financial Plan

What March Madness Can Teach Us About Your Financial Plan

Who's the "Cinderella" team that you predict with bust brackets in this year's March Madness?

Everyone loves a good underdog story, but the history of the Big Dance tells us that the clock strikes midnight more often than not. There are more than 350 schools in Division 1 men's basketball. But 62 of the 84 National Championship games played since 1939 have been won by only 15 teams, headed by perennial powerhouses UCLA (11 titles), Kentucky (8), North Carolina (6), Connecticut (6), Duke (5), and Indiana (5). A hot streak might propel a surprise school through an extra round or two of the tournament. But much like a solid financial plan, schools that have consistently built their programs for the long run tend to get the best results.

Here are three more traits of successful teams that can make your financial program a consistent winner.

The Real Answer to Your Financial Questions: It Depends

The Real Answer to Your Financial Questions: It Depends

When it comes to personal finance, one of the most common—and frustrating—answers you’ll hear is, “It depends.” Whether you’re asking about the best way to invest, how much you should save for retirement, or how to minimize your tax burden, the response is often the same. And while “It depends” might seem like a cop-out, it’s actually the most honest and accurate answer anyone can give. Here’s why - your financial situation is unique and personal to you…

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Should I Pay Off My Mortgage?

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Should I Pay Off My Mortgage?

Being unsure whether to pay off your mortgage or not is a good problem to have. It means you have significant savings and have afforded yourself some choices. While the idea of being debt-free is appealing to many, there are also compelling reasons to keep your mortgage. Let’s explore both sides of the debate to help you make an informed decision.

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Having the “Money Talk” with Aging Parents

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Having the “Money Talk” with Aging Parents

Discussing finances with aging parents is never easy. As a result, many families simply delay these conversations or avoid them altogether. This can lead to unexpected financial surprises, misunderstandings, and even conflicts down the road.

By talking openly about money, you ensure both their future and yours are secure, prevent potential disputes, and help in planning for long-term care. Your goal in having this conversation is not just about understanding their financial situation but also about ensuring financial stability and facilitating smooth estate planning.

Parents who have accumulated wealth over the years may be resistant to the idea that they need help managing their money. It’s important to be mindful of your language and positioning. It’s not, “I need to know how much money you have.” Nor is it, “You shouldn’t do this by yourself.” There are more delicate ways to broach the subject, and we’ve outlined a few possible scenarios below:

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Should You Buy or Build Your Dream Home?

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Should You Buy or Build Your Dream Home?

The choice between buying and building a house hasn't become much easier in 2024. While the housing market has cooled off a bit this year, high building costs and interest rates are helping to support high home sale prices. According to Forbes, the average cost to build a new house is around $329,000 - not including the cost of land.

We can help you run some numbers on the money part. There’s a lot more that goes into a true "dream home" other than money, especially if you're thinking about living there through retirement. Discussing these three questions with your family can clarify what a home really means to you, and how the journey to your next home could impact your Return on Life (ROL).

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Managing a Family Retreat Across Generations

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Managing a Family Retreat Across Generations

A family might spend decades working and saving towards the goal of owning a vacation home. The memories made are priceless, but the personal, emotional, and financial costs of keeping that house in your family for generations can be very high and very painful without thorough planning.

Prepare a family retreat into your legacy plan and make sure you discuss these three points with your heirs, your attorney, your CPA, and your financial advisor.

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5 Ways to Incorporate Unexpected Cash in Your Financial Plan

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5 Ways to Incorporate Unexpected Cash in Your Financial Plan

Receiving an unexpected sum of money can be a welcome surprise, but deciding what to do with it can be a challenge. Should you save the money or pay down debt? Invest the funds or donate to charity?

While rushing to book a vacation with proceeds from a windfall may be tempting, it might be more rewarding to use the funds to shore up your finances for the long run. Here are five strategies to consider: