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  • Curriculum
    • Class Catalog
    • (01) Investing in Fitness
    • (02) Legal Documents
    • (03) Social Security
    • (04) TIPS Ladder
    • (05) Investment Portfolio
    • (06) Taxes in Retirement
    • (07) Spending Capacity
    • (08) Medicare Enrollment
    • (W1) Roth Conversions
  • Recommended Resources
  • Intro Videos
  • Focus Areas
  • More
    • Home
    • About
    • Fees
    • Schedule Intro Meeting
    • Strategic Directions
    • Curriculum
      • Class Catalog
      • (01) Investing in Fitness
      • (02) Legal Documents
      • (03) Social Security
      • (04) TIPS Ladder
      • (05) Investment Portfolio
      • (06) Taxes in Retirement
      • (07) Spending Capacity
      • (08) Medicare Enrollment
      • (W1) Roth Conversions
    • Recommended Resources
    • Intro Videos
    • Focus Areas

  • Home
  • About
  • Fees
  • Schedule Intro Meeting
  • Strategic Directions
  • Curriculum
    • Class Catalog
    • (01) Investing in Fitness
    • (02) Legal Documents
    • (03) Social Security
    • (04) TIPS Ladder
    • (05) Investment Portfolio
    • (06) Taxes in Retirement
    • (07) Spending Capacity
    • (08) Medicare Enrollment
    • (W1) Roth Conversions
  • Recommended Resources
  • Intro Videos
  • Focus Areas

Class Catalog

Start Here

These classes are the foundation of Ty's Retirement Roadmap — a collection of educational videos designed to walk you through the key decisions and concepts that shape a secure retirement. 


A few things worth knowing before you dive in

The content is substantive and built to genuinely inform — these aren't surface-level overviews. That said, production quality is a work in progress. The ideas are solid, the delivery is being refined, and classes will be re-recorded over time as the material improves.


Most of the classes are designed to be audio-friendly — you don't need to be watching the screen to follow along. That makes them well-suited for listening at your own pace, especially while walking.


One practical note: launch the videos from this website, not directly from YouTube. The experience here is cleaner and more organized than searching for them on YouTube individually.

Education Classes

Investing in Fitness

Legal Documents (Estate Planning

Legal Documents (Estate Planning

Jump to Class

Legal Documents (Estate Planning

Legal Documents (Estate Planning

Legal Documents (Estate Planning

Jump to Class

Social Security

Legal Documents (Estate Planning

Social Security

Jump to Class

TIPS Ladder

Investment Portfolio

Social Security

Jump to Class

Investment Portfolio

Investment Portfolio

Investment Portfolio

Jump to Class

Taxes in Retirement

Investment Portfolio

Investment Portfolio

Jump to Class

Spending Capacity

Roth Conversions Workshop

Roth Conversions Workshop

Jump to Class

Roth Conversions Workshop

Roth Conversions Workshop

Roth Conversions Workshop

Jump to Class

Asset Location

Asset Location Video (17:41)

Top 3 for retirement savings

Top 3 for retirement savings

Top 3 for retirement savings

  • Taxable (brokerage)
  • Tax deferred (401k, Traditional IRA, other tax advantaged retirement accounts
  • Tax free (Roth 401k, Roth IRA)

Out of scope

Top 3 for retirement savings

Top 3 for retirement savings

  • Cash under the mattress
  • Gold bars in the household safe
  • Life Insurance
  • Real Estate

Who this applies to

Top 3 for retirement savings

Why Roth can be a favorite

  • Near or in retirement
  • Households with significant retirement savings already accumulated
  • Still working, but income isn't expected to change significantly
  • Doesn't cover people who are early in their savings years — the applied math is different there

Why Roth can be a favorite

Why Roth can be a favorite

Why Roth can be a favorite

  • Aside from the 5-year rule, Roth dollars are free and clear — no future tax bill attached
  • For more on getting money into Roth, see the Roth Conversion workshop series

Tax-deferred vs. Roth

Why Roth can be a favorite

Tax view for Brokerage

  • Growth in a 401(k)/Traditional IRA is tax-deferred — but if your tax rate is the same now and in the future, the after-tax result can be mathematically identical to a Roth
  • Example: $1,000 pre-tax, 20% effective tax rate, same investment (Total US Stock Market ETF) that doubles 
  • Roth path: pay tax first → $800 invested → doubles to $1,600, all tax-free
  • Tax-deferred path: $1,000 invested → doubles to $2,000 → pay 20% tax on withdrawal → $1,600
  • Same result, when the tax rate doesn't change

Tax view for Brokerage

Why Roth can be a favorite

Tax view for Brokerage

  • Same $1,000, but this time $800 after-tax goes into a taxable brokerage account
  • Will ignore dividend yield ~1% 
  • When it doubles to $1,600, that's an $800 capital gain
  • At a 15% long-term capital gains rate: $120 tax → $1,480 net
  • No tax on capital gain if beneficiaries inherit

Copyright © 2026  Ty Rollins - All Rights Reserved.

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