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

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

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.