Stay Wealthy San Diego

A recent study reported that 76% of retirees regret not saving more money. But after working with hundreds of successful retirees and analyzing thousands of survey responses, I've discovered something interesting:  Their deepest regrets actually have little to do with financial shortfalls. Instead, they revolve around critical aspects of financial planning that significantly impact purpose, independence, and fulfillment in your golden years. In this episode, I'm revealing three (3) retirement regrets that many people don't consider until it's too late. I'm also sharing how to avoid the same mistakes so YOUR retirement is fulfilling instead of filled with regret. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes.

Wondering how the new 'One Big Beautiful Bill Act' affects you and your retirement plan? Don't want to read 870 pages of Congressional jargon? I've got you covered! In this episode, I'm breaking it all down and sharing the 5 biggest things retirement savers need to know. I'm also addressing several broader provisions in the bill and clarifying some common misconceptions. This giant (and confusing!) economic package touches nearly every aspect of your financial life. So, pour yourself some coffee—or something stronger if you need it—and hit play. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families in 40 states across the country navigate retirement, optimize investments, and reduce taxes.

Think you need millions of dollars to retire comfortably? Think again. Most people believe they're "behind" on retirement savings because they're measuring against arbitrary benchmarks that don't reflect their unique situation. But what if retiring at 62 is actually more achievable than you've been led to believe? In this episode, I'm sharing: ► Why you should ignore popular savings benchmarks ► Why delaying Social Security isn't always the right move (and how taking it early might preserve MORE wealth) ► A simple 4-step process to build your personalized early retirement plan If you're tired of feeling behind and want to discover how early retirement might be within reach right now, this episode is for you. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Need retirement & tax planning guidance?  We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes.

"I planned for 30 years of expenses—but zero years of purpose." This was a recent client's confession, and she's not alone. In fact, nearly 40% of retirees say they wish they had waited longer to retire (and it's not about money).  In this episode, I'm revealing why even the most financially prepared retirees fall into identity crises and regret. I'm also sharing my 5-step "Bridge Strategy" to help you retire with clarity and purpose, not just a seven-figure portfolio.  If you're planning FOR retirement but haven't considered what you're retiring TO, this episode is for you. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Need professional retirement & tax planning help?  We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes.

"Cash is king" has guided investors since the 1987 market crash. But what if this so-called "king" is actually putting your retirement plan at risk? Millions of retirees are lured by today's enticing cash yields, confusing safety nets for sound investment strategies. In this episode, I'm revealing why cash (even at 4-5%) is a deceptive long-term investment. I'm also sharing details about a critical investment performance metric to help you make more informed portfolio decisions. If you're wondering how to balance safety and growth in today's uncertain market, this episode is for you.  *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly.

You’ve finally made it to retirement! But what if some of the choices you’re making right now are quietly pulling you back to work? Every year, countless retirees are forced back into the workplace. Not because they were reckless, but because they followed advice that sounded smart and safe. In this episode, I'm sharing 7 of the most common retirement pitfalls that can derail even the best-laid plans. I'm also sharing our Total Retirement System™—a comprehensive framework to ensure you retire once and never look back.  If you're approaching retirement (or already there) and want to avoid mistakes that force people back to work, this episode is for you. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly.

"I'll just work a few more years." It's the retirement safety net millions of Americans often count on. In large part because the financial industry has convinced everyone that retiring later is the most sensible backup plan if your savings fall short. But what if this common advice is actually setting you up for one of the most costly mistakes of your life? In this episode, I'm sharing why the real danger may not be running out of money in retirement, but rather working too long. I’m also sharing why choosing the right withdrawal strategy may help you retire sooner AND give you more confidence to spend in retirement.  *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly.

Today I'm diving into the tariff-induced market mania that has been dominating every news headline. Specifically, I'm joined by Cullen Roche, monetary economics expert and founder of Discipline Funds, to discuss three important things: ► How tariffs actually work and why economists across the political spectrum overwhelmingly agree they are bad ► What the recent tariff proposal means for the economy (and American consumers) ► What yesterday’s "90-day pause" means for the markets going forward We also discuss how retirement investors should approach their portfolios during this period of economic uncertainty + what changes are prudent to make. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly.

ESG investing is exploding in popularity—but it's also a giant, confusing mess. Over $35 trillion in global assets now follow ESG guidelines.

Morningstar recently published its annual "State of Retirement Income" research report. This year’s report finds the highest 30-year safe withdrawal rate for retirees is... 3.7%

Today I'm discussing the biggest retirement investment risk. As Morgan Housel put it, "It's the hardest risk for people to understand...  ...and it's the only one that really matters." In this episode, you'll learn: ► What the three sides of risk are ► Why tail risk is all that matters ► How to mitigate this risk in your retirement plan You'll also learn why most investors should (probably) stay away from investment products promising you lots of upside with limited downside.  *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly.

Worried about Medicare IRMAA eating into your retirement savings?  Whether you're 10+ years away from Medicare or already enrolled, this episode will help you navigate this pesky surcharge and protect your retirement savings. Key topics covered: ► Updated 2025 IRMAA brackets  ► Answers to common planning questions  ► 3 strategies to minimize (or avoid) IRMAA You'll also learn how to project future IRMAA brackets for better planning. If you want a clear roadmap for making informed decisions about your future healthcare costs, you'll enjoy today's episode. *** RETIREMENT & TAX PLANNING: 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!

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!