Stay Wealthy San Diego

Markets tend to operate in cycles—yesterday's winners often become tomorrow's losers (and vice versa).  The most unloved asset classes can quietly become the best performers, while the most popular ones frequently disappoint. Yet, many investors fall into the trap of assuming recent trends will continue indefinitely. But markets don’t work that way. No asset class outperforms or underperforms forever. To help you avoid falling into this trap (and make more informed portfolio decisions), I’m sharing key takeaways from Vanguard's 2025 Market & Economic Report in this episode.  I’m also sharing 5 actions retirement savers can take right now to prepare for success over the next decade and beyond. *** Looking to hire a financial planner with retirement & tax planning expertise? My team and I only have a few more openings for Discovery Meetings with new clients.  If you're seeking professional help, we would love to have a conversation!

Looking to hire a financial planner with retirement & tax planning expertise? My team and I have availability for 25 Discovery Meetings over the next 8 weeks. If you're seeking professional retirement planning help, we would love to have a conversation!

Grab your Tax Planning Cheatsheet (updated for 2025!) by clicking here. The 2-page PDF guide includes every important number you'll need for your retirement & tax planning next year. Updated federal income tax brackets, AMT annual limits, standard deductions, Social Security taxation summary, estate and gift tax annual limits…and more.

How do we fix the housing affordability problem in the U.S.? Will lower interest rates really improve the real estate market? How have Zillow and Airbnb contributed to the current housing challenges?   What are tariffs (+ benefits and drawbacks)? What's next for the U.S. economy?  These are just a few of the questions I'm exploring in this episode with author and economic expert, Kyla Scanlon.  *** BOOK GIVEAWAY I'm giving away 10 copies of Kyla's beautifully written and designed book, "In This Economy? How Money & Markets Actually Work." To put your name in the hat and receive a free copy, be sure you're subscribed to the Stay Wealthy Retirement Newsletter by visiting https://www.youstaywealthy.com/email. Next week, my team will randomly select 10 lucky readers to give our copies away to. 

Today, I’m discussing the challenges of spending money in retirement.  To help, Brian Portnoy, one of the world’s leading experts on the psychology of money, joins us to discuss three big things: ➤ Why it’s so difficult for retirement savers to transition from saving to spending ➤ What you can do to prepare for the (well-documented!) challenges of retirement spending  ➤ How to use Brian’s “Four C’s” to achieve true wealth in retirement We also delve into the meaning behind Brian’s famous quote, “Diversification always means having to say your sorry,” and how it can help you make better investing decisions. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter!

Emerging Markets are the world’s primary drivers of global growth (and wealth accumulation). Just over 50% of the world's economic output comes from these countries.

Why are most people planning for the wrong things in retirement? What should they be planning for that they’re not? To help answer these important questions, Psychologist & Behavioral Finance Expert Dr. Daniel Crosby stops by to discuss: ➤ What our happiness is determined by ➤ Why (contrary to popular research) more money can ACTUALLY make us happier ➤ What is the “PERMA model” and how can we use it to improve retirement success We also discuss why retirees are more depressed than everyone else and what they can do to mitigate this risk. *** THE SOUL OF WEALTH:  Grab a copy of Daniel's new book, The Soul of Wealth.  The book explores what wealth really is and provides practical suggestions for how to change your thinking and your actions in small, powerful ways, for a wealthier life. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirem

Today, I'm talking about navigating the risks of concentrated investments. Specifically, Peter Lazaroff, CIO of Plancorp, joins me to answer three BIG questions: ➤ How do you know if you have a "concentrated investment?" ➤ What are some little-known risks investors aren't considering? ➤How do you (tax-efficiently) diversify concentrated investments? I also share a specific exercise investors can follow to decide if they should sell some or all of their concentrated holding(s). *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter!

Today, I'm sharing how retirement investors can take action in this final episode of our Small Cap Value series.  Specifically, I’m discussing three things:  ➤ Why paying MORE for an investment can pay off ➤ How to easily and properly evaluate different funds  ➤ What small-cap value funds to consider  I’m also sharing two important reminders before taking action and investing in this popular asset class. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter!

Today, I’m diving into part two of our Small Cap Value investing series. Specifically, I’m addressing three big questions: ➤ How do small-cap value stocks reduce risk + improve returns  ➤ What criteria does an investment need to meet to be included in a portfolio ➤ Why value investing is still alive and well While there is no shortage of research in favor of this dominant asset class... ...I’m also sharing why investors don’t necessarily need small-cap value stocks to reach their retirement goals. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter!

Today I’m kicking off a two-part series on Small Cap Value investing. Specifically, I’m addressing three big questions: ➤ What exactly are small-cap value stocks? ➤ Why have small-cap value stocks, historically, outperformed most major asset classes? ➤ Does the recent 20-year underperformance suggest that the strategy is dead and won’t work in the future?  I’m also sharing critical differences between small-cap value funds + how to take action if you want to include this asset class in your portfolio. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter!

Today, I'm sharing key takeaways from three of the BEST retirement articles I read this month. 1️⃣ The first article is about the future of taxes in this country and specifically makes a strong case for why they will be higher. 2️⃣ The second reveals why investors missed out on 15% of investment returns over the last decade.

Today, I’m sharing FIVE surprising statistics about the economy, markets, and retirement. For example, one stat highlights a "stock market indicator" that has a 100% success rate

Are you ready to get answers to some BIG retirement questions? Questions such as: ➤ What role does the equity in my home play in my retirement plan? ➤ Why should I do Roth conversions to help mitigate taxes on my kids' inheritance? ➤ Are closed-end funds a good investment? ➤ How do I properly evaluate pension vs. lump-sum decisions? Today on the show, I’m answering these questions (and more!) with my good friend, Roger Whitney. I'm also providing an update on the Retirement Podcast Network after taking a hint from 1,000+ retirement savers.   *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :) 

Required Minimum Distributions (RMDs) begin at age 73 for most retirement savers. These forced withdrawals can be a burden for those who don't need (or want) the taxable income. Since they are “required,” many assume that they don't have any control over their RMDs. But that’s not necessarily the case. In fact, one of the 5 strategies I'm sharing with you today allows you to delay unwanted (mandatory) distributions well past age 73

In the final episode of this series, I'm answering the BEST listener questions I've received about dividend investing. Questions such as: ➤ If dividend investing is NOT a great way to create retirement income, what is?  ➤ What dividend-focused funds should investors consider if they insist on investing for yield?  ➤ What is the counterargument for stock buybacks? Why are some people against them? Tune in to hear my answers to these great questions! FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter. 

In today's episode, I'm sharing everything you need to know about stock buybacks. Specifically, I'm sharing: ➤ Why stock buybacks are referred to as a "flexible" dividend ➤ What a stock buyback is (and how it works) ➤ How stock buybacks are more tax-friendly than traditional dividends If you want to learn more about this increasingly popular "flexible dividend" strategy, you'll enjoy this episode. FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter. 

Today I'm continuing our multi-part series on Dividend Investing. Specifically, in part two, I’m sharing: ➤ What the long-term performance has been for dividend-focused funds ➤ Why popular dividend investing charts can be incomplete (or misleading) ➤ The 3 primary reasons dividend strategies typically underperform If you want to learn more about dividend investing and why it may not be the magical solution it's often marketed as, you'll enjoy this episode.  *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter. 

Today I'm kicking off a multi-part series on Dividend Investing. While dividends are a normal occurrence in the global markets, their role in a retirement portfolio is often misunderstood. ➤ What is a dividend, and why do some companies pay them?  ➤ How do they affect an investor's return? ➤ Where do dividends fit in the portfolio construction process?  ➤ What are the little-known problems with this investment strategy? ➤ And what does my upcoming birthday have to do with dividends?

Today I'm sharing a story about a couple who lost $2 million to an investment scam. I'm also sharing (new!) resources to help protect your personal data in 2024. Financial scams are getting more sophisticated and losses are skyrocketing. In fact, last year, Americans lost $10 billion to financial scams. That’s $1 billion more than 2022, and is the highest-ever reported annual loss in FTC history. Everyone is at risk. And everyone needs to regularly take proactive steps to stay safe. Tune in to learn more. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :)