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

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

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

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.

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

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.

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

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