Certified Public Accountant
Accredited Investment Fiduciary
BIOGRAPHY
Alan Clopine is the Executive Chairman of Pure Financial Advisors, LLC (Pure). He has been an executive leader of the Company for over a decade, including CFO, CEO, and Chairman. Alan joined the firm in 2008, about one year after it was established. In his tenure at Pure, the firm has grown from approximately $50 million in assets under management to over $11.05 billion (as of February 12th, 2026).
Prior to joining Pure, Alan was the founding and senior partner at Clopine & Associates, LLP, a CPA firm established in 1987 and located in San Diego. In addition to providing traditional tax and accounting services for successful individuals and businesses, the firm specialized in real estate, technology, and small business tax planning. The firm was consistently ranked in the top 50 CPA firms in the San Diego Business Journal, “Book of Lists.”
Alan has provided tax planning services for individuals, corporations, and trusts for over 35 years. From 2008 to 2024, Alan was the co-host of Your Money, Your Wealth®, a financial talk radio show heard weekly in San Diego on KFMB. He has co-hosted the Your Money, Your Wealth® podcast since 2016. In addition, Your Money, Your Wealth® is a weekly television show that is aired in multiple markets and is available on YouTube.
Alan received a bachelor’s degree from the University of California, San Diego in 1979 and received his CPA certification in 1984. He was the former board president of Vida Joven, a non-profit organization that supports an orphanage in Tijuana. He is actively volunteering with St. Peters Episcopal Church. When his kids were young, he volunteered for over ten years, coaching youth sports in baseball and soccer. Alan enjoys time with family and friends, traveling, staying fit, hiking, golfing, and playing his ukulele. Alan is married to Anne and has two adult sons named Robbie & Ryan.
Alan's Latest Contributions
B and S in Maryland are in their mid-40s with $425,000 and a couple of rental properties. Can they retire early at 62? Vee in Oregon came to the US as a refugee with nothing and built a three and three-quarter million dollar portfolio from the ground up. Is his Roth conversion plan solid? And finally, Chandler and Monica in Texas are sitting on $1.4 million and hope they can walk away from work in 3 years. Will Roth conversions keep the tax man from taking a giant bite on their way out?
What is IRMAA, and why does it matter for Roth conversions?
IRMAA, the Income-Related Monthly Adjustment Amount, is a surcharge added to Medicare Part B and Part D premiums when income rises above certain thresholds. Because Roth conversions raise taxable income in the year they happen, a large conversion can push you past an IRMAA threshold and increase your Medicare premiums about two years later, so timing conversions around those limits matters.
Frequently Asked Questions
Q: What does it mean to “cover the gap” in retirement?
A: The gap is the difference between what you want to spend each year and your guaranteed income from sources like Social Security, a pension, and rental income. Whatever those sources don’t cover has to come from your investment portfolio, and that shortfall drives how much you need saved. In the case of early retirement, “covering the gap” can also refer to how you fund the time between when you stop working and when you start drawing Social Security benefits and/or a pension.
Q: Should you make Roth or pre-tax 401(k) contributions?
A: Pre-tax contributions lower your taxable income now and are taxed when you withdraw them. Roth contributions use after-tax dollars and can come out tax-free later. Roth often makes sense when your current tax bracket is similar to or lower than the bracket you expect to be in during retirement.
Q: How can Roth conversions help reduce future required minimum distributions?
A: A Roth conversion moves money from a pre-tax IRA or 401(k) into a Roth account. Because original Roth owners have no RMDs, converting before RMD age can shrink the pre-tax balance that would otherwise be forced out and taxed as ordinary income later in retirement.
Q: Why does a surviving spouse’s tax situation matter when planning conversions?
A: When one spouse passes away, the survivor usually files taxes as single, where the same income falls into higher brackets than it did filing jointly. Converting to Roth while both spouses are alive can move money out at today’s joint-filing rates before that shift happens.
Joe and Big Al spitball for people with a small fortune sitting in pre-tax accounts, turning into a tax bomb. We’ll find out how Roth conversions and careful tax liability management can optimize their retirement income strategy. Eric in California is 72 with nearly $4M in pre-tax accounts. How much should he transfer in Roth conversions? Is borrowing against his own house to pay the tax bill brilliant or bonkers? Rick and Kiani are hoping they can quit sooner than they think. Mike just hit full retirement age. Should he claim Social Security benefits now or wait until age 70? And finally, Jeff wants to walk away at 59 with a roadmap for aggressive Roth conversions, assuming the tax cliff doesn’t get him first.
How do Roth conversions help reduce the taxes on a large pre-tax retirement account?
A Roth conversion moves money from a pre-tax IRA or 401(k) into a Roth account, where it grows tax-free and has no required minimum distributions for the original owner. Converting during lower-income years, before RMDs begin at age 73 or 75, can reduce the pre-tax balance that will later be taxed as ordinary income.
Frequently Asked Questions
Q: What is a “retirement tax bomb”?
A: A retirement tax bomb is the oversized tax bill that can come due when most of your savings sit in tax-deferred accounts like traditional IRAs and 401(k)s. Withdrawals are taxed as ordinary income, and required minimum distributions are mandatory, so a large pre-tax balance can push a retiree into higher tax brackets later in life.
Q: Can you use a home equity line of credit to pay the tax on a Roth conversion?
A: Some retirees consider borrowing against home equity to cover the tax owed on a conversion instead of pulling those dollars from the account being converted, which keeps more money invested in the Roth. It also adds debt and interest costs, so whether it works depends on your interest rate, cash flow, and overall plan.
Q: Should you claim Social Security at full retirement age or wait until 70?
A: Claiming at full retirement age, which is 67 for most people today, gives you your full benefit. Waiting increases it by roughly 8% for each year you delay, up to 124% of the full amount at age 70, and it can raise the survivor benefit for a spouse. The right timing depends on your health, other income, and how long you expect to need the money.
Q: What is the rule of 55?
A: The rule of 55 is an IRS provision that lets you take money from your current employer’s 401(k) without the 10% early-withdrawal penalty if you leave that job in the year you turn 55 or later. It applies to 401(k)s rather than IRAs, and individual plan rules can differ, so confirm the details with your plan administrator.
Q: Is it better to make Roth or pre-tax 401(k) contributions?
A: Pre-tax contributions lower your taxable income now and are taxed when you withdraw them in retirement. Roth contributions are made with after-tax dollars and can come out tax-free later. Roth often makes sense when you expect to be in a similar or higher tax bracket in retirement, which is common for diligent savers who build up large pre-tax balances.
Half of Americans admit they have zero retirement preparedness. Most don’t even have real income plans. Joe Anderson, CFP® and Big Al Clopine, CPA walk through actual cash flow projections, market loss recovery strategies that don’t blow up your timeline, and the Medicare enrollment and Social Security calls that can make or break your plan. Retirement […]
