James Clendenin

James Clendenin, a seasoned entrepreneur and financial guide, brings decades of real-world experience to HappyWallet.co, where he writes alongside his son, Riley Clendenin. As a senior who has navigated the ups and downs of building businesses and managing finances, James understands the importance of cultivating a strong Financial IQ at every stage of life. His journey began with a passion for entrepreneurship, but over the years, he realized that true success lies not just in earning money but in managing and multiplying it wisely. Through thoughtful articles and practical insights, James shares his hard-earned wisdom with Millennials and Gen Z, offering guidance on everything from smart investing to building financial resilience.

It’s Not About Love, It’s About the Economy: 9 Real Reasons ‘Sugar Dating’ Exists

July 25, 2025 by James Clendenin

The arrangement is a direct response to a massive wealth gap.

The world of “sugar dating,” where a wealthier, often older person provides financial support to a younger partner in exchange for companionship, is frequently misunderstood. It’s easy to dismiss it with simple labels, but the rise of these arrangements is a direct symptom of the powerful economic forces and social shifts that have defined a generation. It is a pragmatic, if controversial, solution to a set of very modern problems.

This is less a story about romance and more a story about the widening gap between the haves and the have-nots.

7 Future Problems With the Buy-The-Dip Mindset Driving the Stock Market

July 24, 2025 by James Clendenin

A strategy that works perfectly until the day it disastrously doesn’t.

For years, the stock market has followed a simple and incredibly profitable script: every time the market drops, it’s a golden opportunity to “buy the dip.” This mindset, which rewards investors for buying into downturns, has become a deeply ingrained reflex for a whole generation of traders. It’s a strategy that has been consistently validated by a market that has always seemed to bounce back stronger.

But what happens when the music stops? There are several growing problems with this seemingly foolproof strategy that could spell trouble ahead.

11 Wedding Expenses That Gen Z Couples Are Having to Finance

July 24, 2025 by James Clendenin

Saying ‘i do’ to debt is the new reality for many young couples.

The tradition of a parent’s generation footing the entire bill for a wedding is rapidly fading into the past. In 2025, Gen Z couples are taking on the financial responsibility for their own big day, and they are doing so in an era of high costs and high expectations. To achieve the wedding they’ve envisioned, many are turning to financing.

From personal loans to “buy now, pay later” services, debt is becoming a common, if unglamorous, part of the modern wedding budget.

Highest in 100 Years: Why These Trump Tariff Deals Feel LIke a Relief

July 24, 2025 by James Clendenin

After a brutal trade war, a return to normalcy feels like a win.

The first half of 2025 was a nerve-wracking time for the American economy, marked by the imposition of the highest tariffs seen in a century. This aggressive trade policy sent shockwaves through global markets, raising prices at home and straining relationships abroad. Now, with a series of new international agreements being reached, a collective sigh of relief can be heard from consumers and businesses alike.

This isn’t just a win for politicians; it’s a tangible relief for the wallets and worries of everyday Americans.

10 Reasons Young Adults Are Calling Their Parents “Absent Baby Boomers”

July 23, 2025 by James Clendenin

It’s not about physical distance, but a growing emotional and practical gap.

A new and painful term has entered the lexicon of generational discourse: the “Absent Baby Boomer.” It’s a phrase used by Millennials and Gen Z to describe a perceived emotional and practical distance from their parents, even when they live in the same city. This isn’t about the classic generation gap; it’s a deeper feeling of being left to navigate the immense challenges of modern adulthood alone.

This sense of abandonment stems from a complex mix of economic realities, shifting family roles, and a profound cultural disconnect that leaves young adults feeling unsupported.

Beyond the Dollars: Why Millennials Are Choosing Pets Over Kids

July 23, 2025 by James Clendenin

It’s not just about the cost, it’s about the emotional and lifestyle math.

The sight of a Millennial pushing a dog in a stroller or referring to themselves as a “pet parent” has become a familiar cultural touchstone. While older generations are quick to point to the high cost of raising a child as the sole reason, the decision is often far more complex than a simple financial calculation. The choice to welcome a pet into the home instead of a baby is rooted in a deep recalibration of life’s priorities.

It reflects a generational shift in the definition of family, fulfillment, and what it means to live a good life in 2025.

Does Jerome Powell Deserve Credit? His Federal Reserve Reduced Inflation From 9.1% to 2.1%

July 22, 2025 by James Clendenin

The numbers look good, but the story of how we got here is complicated.

By the numbers, the tenure of Federal Reserve Chair Jerome Powell looks like a resounding success. He inherited an economy spiraling into the highest inflation in 40 years and, through a series of aggressive policy moves, steered it back toward the Fed’s 2% target. The drop from a peak of 9.1% inflation to today’s more stable 2.1% is a remarkable achievement that has impacted every American’s wallet.

But was it all Powell’s doing, or was he a beneficiary of circumstance? The debate over his legacy is complex, with strong arguments on both sides.

11 Cities Where a Six-Figure Income Is Required to Feel “Middle Class”

July 22, 2025 by James Clendenin

The six-figure salary is the new middle-class benchmark in these cities.

The term “middle class” once conjured a clear image of financial stability, but that picture has become increasingly blurred in America’s most dynamic cities. The traditional goalposts for a comfortable life—owning a modest home, saving for the future, and having a little left over for fun—have shifted dramatically. In a growing number of urban centers, a six-figure income no longer feels like a path to wealth; it feels like the bare minimum for survival.

Here in California, we know this reality all too well. These are the cities across the U.S. where making $100,000 a year can still feel like you’re just getting by.