Make the Most of Your Money Podcast

#32- AI and Financial Planning

Wed, 11 Mar 2026 05:00:00 -0400

We explore how AI actually helps with money—what it accelerates, where it fails, and how to use it without risking your life savings. We weigh job market risks, resilience moves like liquidity, and why human judgment and behavior still drive real results.

• using AI for frameworks, summaries, and first-pass projections
• limits of AI in taxes, edge cases, and incomplete context
• behavior and values as the bottleneck, not knowledge
• practical ways advisors use AI for notes, research, and communication
• job disruption risk, liquidity buffers, and insurance hygiene
• skills that compound with AI versus skills that compete
• parallels to robo-advisors and raising professional standards
• how to experiment safely and verify before acting

#31 - How to handle concentrated stock positions

Tue, 24 Feb 2026 05:00:00 -0500

We dig into the real risks of single-stock wealth, why diversification protects your future, and how to navigate taxes, FOMO, and strategy without losing what you’ve earned.

• defining concentration by impact on your life, not a fixed percentage
• where big positions come from, including employer equity
• why FOMO and upper bounds distort judgment
• winners vs diversification and the humility of market history
• thinking in after-tax terms and ditching pre-tax anchoring
• immediate sale vs staged sales and bracket-aware plans
• tax loss offsets as pressure relief, not a driver
• donating appreciated stock and donor-advised funds
• step-up in basis for late-life planning, with limits
• securities-based lending for short-term liquidity
• charitable remainder trusts and pooled vehicles
• double risk of employer stock when your job matches your shares
• survivorship bias in success stories and durable principles

#30 - Giving money to kids

Tue, 03 Feb 2026 05:00:00 -0500

There's a lot that goes into giving money to kids (or receiving money as a child.) There are tax ramifications, behavioral impacts, and of course "spiritual" elements to consider. We'll talk about how to plan for giving or receiving a gift, the supposed tax "limits" to giving, and what not to do.

We'll also talk about:
• balancing generosity with grit and intrinsic motivation
• the coming wealth transfer and planning implications
• when to plan for expected gifts or ignore them
• annual exclusion myths and lifetime exemption rules
• gifting cash vs appreciated stock and basis tradeoffs
• adult vs minor gifting, control and timing differences
• 529 benefits, aid considerations, and K–12 uses
• UTMA/UGMA pros and cons, parent brokerage earmarks
• when trusts make sense and when they do not
• “Trump accounts” benefits, limits, and open questions
• the value of experiences as gifts
• transparency, changing priorities, and legacy beyond heirs

#29 - What Got You Here Won't Get You There

Tue, 20 Jan 2026 05:00:00 -0500

We explore why retirement is a true pivot point: identity shifts, new risks, and the move from one paycheck to many income streams. We share practical ways to plan with uncertainty, from guardrails to healthcare decisions, and how to retire to something with purpose.

• identity, structure and purpose beyond your job
• switching from saving to spending with multiple income sources
• taxes moving from reactive to proactive planning
• underspending bias and how to set guardrails
• sequence of returns risk and withdrawal design
• healthcare and long-term care trade-offs
• cognitive decline, decision-makers and family roles
• using the house: downsizing, reverse mortgage options
• flexibility, year-to-year reviews and practical next steps

#28 - Rules of Thumb: Which to Trust and Which to Ignore

Tue, 06 Jan 2026 05:00:00 -0500

We test the most common money rules of thumb and show how to adapt them to real life. From saving rates to Social Security timing, we map the assumptions under each rule and explain when to trust them and when to change course.

• saving 15 to 20 percent as a flexible target
• emergency fund size by income stability and risk
• stock and bond mix guided by time horizon and inflation
• retirement spending built from actual expenses, not income
• the 4 percent rule as a floor with dynamic adjustments
• total-return withdrawals vs living only on income
• renting vs owning trade-offs across time horizons
• marginal tax brackets and why “next bracket” fears mislead
• Social Security timing across health, cash flow, and spouses

#27 - Love thy neighbor w/ Reverend Josh Bascom

Tue, 23 Dec 2025 05:00:00 -0500

We explore why money reveals our inner life more than our bank balance, and how purpose transforms financial decisions from optimization to meaning. Rev. Josh Bascom joins us to dig into self-help’s limits, AA’s wisdom, and the power of loving your neighbor.

• technical behavioral spiritual lens for money
• money anxiety identity and privacy around numbers
• rich versus wealthy and status signaling
• comparing our insides to others’ outsides
• self-help frameworks versus purpose
• suffering as catalyst for change
• 12 steps higher power confession and amends
• love of neighbor as guiding purpose
• money as tool not measuring stick
• practical planning once purpose is clear

Check out Josh’s writing on Substack: Cross Street.

#26 - Permanent Life Insurance

Tue, 25 Nov 2025 05:00:00 -0500

We step back from “term good, perm bad” and map the real trade‑offs of permanent life insurance. We explain whole life, UL, VUL, IUL, and GUL, where they fit, where they fail, and how to avoid sales traps by matching the product to the problem.

• term versus permanent: cost, certainty, purpose
• whole life guarantees and steady cash value
• universal life flexibility and moving parts
• variable UL market exposure and premium risk
• indexed UL caps, floors, and illustration pitfalls
• guaranteed UL for low‑cost permanent death benefit
• permanent needs: special‑needs care, legacy, liquidity
• tax angles: income‑tax‑free death benefit, tax‑deferred cash value
• sales tactics to question and fee awareness
• what to do with an existing policy: keep, reduce, exchange, gift, sell
• guardrails: right sizing, clear goals, realistic expectations

#25 - A new take on Variable Universal Life w/ Victor Yates

Tue, 11 Nov 2025 05:00:00 -0500

Variable Universal Life is a complicated life insurance product that may not have the best reputation, but we visit with Victor Yates of Nationwide to learn about how they are doing things differently.

We'll discuss the role of life insurance in general in a financial planning, when permanent life insurance is a fit, how Nationwide's VUL works, and who it is best for.

As a reminder, Colin and Taylor do not sell insurance. This is a detailed discussion on the inner workings of an important financial planning tool.

#24 - When to make changes to your portfolio

Tue, 28 Oct 2025 05:00:00 -0400

We unpack why most portfolios don’t need frequent changes and how a clear purpose, time horizon, and risk preference do the heavy lifting. We trade “performance reviews” for plan reviews, walk through rebalancing and tax tactics, and explain how to ignore scary headlines and shiny objects.

• setting allocation by purpose, time horizon, and risk
• why daily market moves rarely justify changes
• when not to act at all-time highs or during drops
• the trap of performance chasing and survivorship bias
• practical rebalancing cadence and thresholds
• rebalancing with contributions and withdrawals
• tax loss harvesting limits and wash sale rules
• direct indexing complexity and future tax overhang
• donating appreciated stock to boost tax efficiency
• plan reviews over portfolio performance check-ins

#23 - Open Enrollment

Tue, 14 Oct 2025 05:00:00 -0400

Clicking “same as last year” might be the most expensive choice you make all fall. We break down open enrollment with a practical, no-fluff framework: protect against the big risks, pay cash for the small ones, and route every eligible dollar through the most tax-efficient account. From health insurance trade-offs to the truth about dental and vision, you’ll get clear guidance you can act on today.

We discuss:

• what open enrollment includes across employer plans, Medicare and ACA
• how to compare health plans using usage, networks and drug coverage
• when HDHPs plus HSAs beat rich PPOs on total cost
• why out-of-pocket maximums change worst-case math
• dental and vision as prepaid maintenance, not true insurance
• group life as a baseline, private term for portability and price
• disability insurance trade-offs, taxation and own-occupation definitions
• which add-ons to skip and when FSAs are a clear win
• coordinating benefits and costs across two employers
• quick notes on Medicare Advantage and Part D review

#22 - How Kids Change Your Financial Plan

Tue, 30 Sep 2025 05:00:00 -0400

While it may seem obvious, having kids drastically changes your financial plan. This episode will cover some of the obvious and less obvious changes and give you practical ways to think about making the tradeoffs you will have to make. Topics covered include:

Budgeting for kids before having them
The Kindergarten myth
If childcare eats one salary, should someone step back?
Putting your own oxygen mask on first (balancing retirement vs education savings)
The most important estate planning decisions you need to make sooner rather than later
How the tax code typically helps parents out
And much more!

#21 - One Big Beautiful Bill

Tue, 16 Sep 2025 05:00:00 -0400

After a brief summer hiatus, we're diving into the newly passed One Big Beautiful Bill (OBBA) to unpack what these changes actually mean for your financial planning.

The good news? Many of the lower tax rates you've enjoyed since 2017 are now permanent (or at least until some future Congress changes them). But beyond that headline, there are several meaningful changes worth understanding – especially if you're over 65, live in a high-tax state, make charitable contributions, or have substantial wealth to transfer to the next generation.

We break down the new "Senior Bonus" exemption that provides $6,000 in tax relief for those 65 and older, explain how the SALT deduction cap increases from $10,000 to $40,000 for itemizers, and explore new rules for charitable giving that benefit both itemizers and non-itemizers alike. For higher-net-worth individuals, we clarify how the estate tax exemption increases to $15 million per person and what that means for your legacy planning.

While some provisions are genuinely helpful, others come with important limitations – income thresholds where benefits phase out, sunset dates when provisions expire, and trade-offs that might affect your healthcare costs. We cut through the confusion of this 870-page legislation to highlight what matters most for your personal situation.

Most importantly, we discuss practical implications: What actions should you consider taking now? How might these changes affect your tax planning for the next several years? And how should you think about the inevitable future changes to come? Join us for this essential conversation about protecting and optimizing your financial future in light of America's ever-evolving tax code.

Colin's article we discuss: https://www.oakleighwealth.com/articles/obbba?rq=beauty

#20 - Tax Landmines in Retirement

Tue, 17 Jun 2025 04:00:00 -0400

Retirement planning requires understanding three major tax landmines that can derail your financial strategy: Required Minimum Distributions (RMDs), the widow's penalty, and beneficiary taxes.

• RMDs are mandatory withdrawals from tax-deferred accounts starting at age 73 (increasing to 75 in the future)
• The percentage of your account that must be withdrawn increases with age, potentially pushing you into higher tax brackets
• The "widow's penalty" refers to the compressed tax brackets when filing as single rather than married filing jointly
• Beneficiaries typically have 10 years to empty inherited retirement accounts, which can create significant tax burden
• Roth conversions during lower-income years can significantly reduce future tax obligations
• Qualified Charitable Distributions (QCDs) allow donations directly from IRAs to satisfy RMD requirements without increasing taxable income
• When passing on wealth, Roth accounts are most tax-efficient, followed by taxable accounts with stepped-up basis, with pre-tax accounts being least efficient
• Opportunistic planning during market downturns can enhance tax-saving strategies
• Taking a year-by-year approach to tax planning while maintaining awareness of these landmines can save substantial money

Read Colin's article on retirement tax landmines here.

#19 - Financial Projections

Tue, 03 Jun 2025 05:00:00 -0400

Financial projections can be both helpful and misleading when planning your financial future. While they provide valuable insights into potential outcomes, they shouldn't be taken as literal predictions of what will happen.

• Your financial life consists of: money in, money out, growth over time, taxes, and inflation. All financial projections are just projecting these variables
• Monte Carlo simulations introduce randomness to account for market volatility and create a range of possible outcomes
• More variables in a projection create more opportunities for error, not necessarily more accuracy
• The real value comes from understanding sensitivities – which factors significantly impact your financial future
• "Probability of success" metrics can be misleading since they don't distinguish between barely succeeding and wildly succeeding
• Financial plans should include predetermined adjustment triggers or "guardrails" that specify when and how to adapt
• For retirees, projections help answer "how much can I spend?" while younger clients benefit more from simple savings calculations
• Regular updates are essential as your financial situation evolves and market conditions change
• Control what you can (savings, investment allocation, insurance) and be prepared to adjust as life unfolds
• Remember: "All models are wrong, but some models are useful"

#18 - Social Security

Tue, 20 May 2025 05:00:00 -0400

Navigating the complexities of Social Security can feel overwhelming, but understanding the fundamentals is crucial to maximizing your retirement security. In this detailed exploration, we break down how Social Security benefits are calculated, when to claim them, and strategies for optimizing your lifetime benefits.

At its core, Social Security functions like a government pension, providing income that lasts throughout your retirement. Your benefit amount depends on two primary factors: how much you've earned and paid into the system throughout your career (specifically your 35 highest-earning years), and when you choose to begin receiving benefits. While you can start as early as 62, delaying until your full retirement age (currently 67 for most people) or even up to age 70 results in substantially higher monthly payments.

We tackle the million-dollar question: when should you claim? The answer hinges largely on life expectancy, with the break-even age hovering around 81-82 years. Live longer than that, and delaying generally pays off significantly. For married couples, the calculus becomes even more nuanced with spousal and survivor benefits entering the equation. The higher earner should consider their claiming strategy based not on their own life expectancy, but on the expected lifespan of the last surviving spouse.

Many listeners worry about Social Security's future, with the Trust Fund projected to be depleted around 2033-2035. We explain why this doesn't mean benefits will vanish – even without changes, the system would still pay about 80% of promised benefits from current payroll taxes. Historically, reforms have always protected those at or near retirement age, making "claim it while you can" strategies unnecessary for those approaching retirement.

Whether you're decades from retirement or making claiming decisions now, this episode provides the framework to understand how Social Security fits into your broader financial picture. Remember: your Social Security statement assumes you'll continue earning at your current level until full retirement age, so early retirement plans should account for potentially lower benefits than projected.

Ready to make smarter decisions about this valuable retirement resource? Listen now to gain clarity on one of retirement planning's most consequential choices, and discover why timing is everything when it comes to maximizing your Social Security benefits.

#17 - Medicare w/ Margo Steinlage

Tue, 06 May 2025 05:00:00 -0400

Understanding Medicare requires navigating complex options, deadlines, and potential pitfalls that can impact healthcare coverage for decades. Insurance broker Margo Steinlage shares expert insights to help individuals approaching retirement make informed Medicare decisions that account for both current and future healthcare needs.

• Medicare enrollment decisions should begin 12-18 months before turning 65
• Medicare is required at 65 unless covered by an active large employer plan (20+ employees)
• Original Medicare covers approximately 80% of costs with no cap on the remaining 20%
• Two main pathways: Medicare with Supplement (maximum flexibility) or Medicare Advantage (network restrictions)
• Initial Medicare decisions have long-term implications due to medical underwriting requirements
• Supplements offer nationwide coverage but higher premiums than Advantage plans
• Advantage plans often have zero premiums but restrict provider networks and require pre-authorizations
• Moving from an Advantage plan to a Supplement becomes difficult after initial enrollment period
• Plan features and costs can change significantly year-to-year, especially with Advantage plans
• Working with an independent Medicare broker provides comprehensive support at no additional cost

Contact Margo at margo@steinlageinsurance.com for personalized Medicare guidance for your specific situation.

#16 - Long-Term Care w/ Roger Cantu

Tue, 22 Apr 2025 05:00:00 -0400

Roger Cantu, of OneAmerica, brings his 36 years of long-term care (LTC) industry experience to the show. We discuss:- What long-term care actually is- How likely you are to need it and for how long- How you can plan for LTC- What medicare covers (and what it doesn't)- The different types of LTC insurance policies- How the LTC insurance landscape has changed- Where and how to begin evaluating LTC insurance

#15 - Healthy Love & Money w/ Ed Coambs

Tue, 08 Apr 2025 05:00:00 -0400

Ed Coambs CFP®, LMFT, CFT-I™ joins the show to talk about relationships and money. As both a therapist and financial planner, Ed brings a unique perspective to the conversation. He discusses identity crisis, attachment theory, how to talk about money in a relationship, and much more.

#14 - Charitable Giving w/ Mike Staman

Tue, 25 Mar 2025 05:00:00 -0400

Mike Staman joins Colin and Taylor to talk about Charitable Giving. They discuss:- Tax-efficient giving- Donor advised funds- How to talk about giving with your family- Giving while you're alive versus dead- and more

#13: Buying Insurance w/ Broc Buckles

Tue, 11 Mar 2025 05:00:00 -0400

Broc Buckles of BC Brokerage joins Colin and Taylor to break down the ins and outs of buying insurance. They discuss what kind of agent to work with, key red flags to watch for, and how to know if you’re getting a good deal.

#12 - Debt

Tue, 25 Feb 2025 05:00:00 -0500

Colin and Taylor break down all things debt—what’s good, what’s bad, how much to take on, and the best way to pay it off. Most importantly, they explore debt from a technical, behavioral, and even spiritual perspective.

#11 - Financial Education Resources

Tue, 11 Feb 2025 05:00:00 -0500

Colin and Taylor discuss where to find financial information—and, more importantly, how to evaluate it—to better educate yourself on personal finance.

#10 - Savings Waterfall

Tue, 28 Jan 2025 05:00:00 -0500

Should you pay off debt or save for retirement? Which accounts should come first? Colin and Taylor break down the ‘savings waterfall’—a step-by-step approach to prioritizing your savings. They walk through Colin’s savings order, discuss key exceptions like HSAs, 529s, and big purchases, and help you make the right choice for your situation.An example of Colin's waterfall:1. Employer Match2. Pay off high interest credit card debt3. Create an emergency fund4. Max out Roth or Backdoor Roth contributions5. Max out employer retirement plan6. Taxable brokerage accountThey also discuss exceptions such as HSAs, 529s, and saving for a big purchase like a house.Check out Colin's article on the topic here: https://www.oakleighwealth.com/articles/retirement-waterfall?rq=waterfall

#9 - Budgeting

Tue, 14 Jan 2025 05:00:00 -0500

Colin and Taylor break down budgeting—what works, what doesn’t, and how to find the best strategy for you.Below are links to the articles discussed in the episode:https://www.oakleighwealth.com/articles/flow-based-budgetinghttps://www.oakleighwealth.com/articles/budgeting-is-optional-tracking-is-necessary

#8 - Saving

Tue, 31 Dec 2024 05:00:00 -0500

Colin and Taylor explore why saving matters, share simple tricks to save more, and unpack the critical tradeoff between spending and saving.

#7 - Taxes

Tue, 17 Dec 2024 05:00:00 -0500

Colin and Taylor break down the mechanics of how taxes work and teach you how to think about taxes so you can make sure you don’t pay more than you need to.

#6 - Estate Planning

Tue, 19 Nov 2024 05:00:00 -0500

Colin and Taylor help you make sure that what you want to happen will happen when the things you don't want to happen happen -- also known as estate planning.

#5 - Insurance

Tue, 05 Nov 2024 05:00:00 -0500

Colin and Taylor explain what insurance is, how to think about its role in your financial plan, and what kinds and amounts of coverage to have.

#4 - Investing Behavior

Tue, 22 Oct 2024 05:00:00 -0400

Colin and Taylor dive deeper into the key factor for investment success: behavior. Learn simple, actionable tips to improve your investment habits—and, hopefully, your results.

#3 - Investment Allocation

Tue, 08 Oct 2024 05:00:00 -0400

Colin and Taylor walk through how to think about what to invest in by laying out their simple three step process.

#2 - Liquidity

Tue, 24 Sep 2024 05:00:00 -0400

Colin and Taylor begin discussing the six variables of financial planning that you can actually control, starting with Liquidity. They'll discuss what liquidity really means, how to measure it, why it is important, and how to think about where to put your cash.

#1 - What making the most of your money means

Tue, 10 Sep 2024 05:00:00 -0400

Colin and Taylor talk in depth about what making the most of your money actually means and how to start doing so in your own life.

Get to Know Colin and Taylor

Tue, 27 Aug 2024 05:00:00 -0400

Get to know Colin Page, CFP® and Taylor Stewart, CFP® as they talk about what led them to the profession of financial advice and give an overview of what they'll be discussing on the Make the Most of Your Money Podcast.

Trailer: Make the Most of Your Money Podcast

Mon, 12 Aug 2024 10:36:20 -0400

Do you ever wonder if you could–or should–be doing something better with your money? If so, you're not alone, and you're in the right place. Listen as Taylor Stewart and Colin Page introduce the “Make the Most of Your Money” podcast and explain just how they will help you begin making the most of your money so you never have to wonder again.