Sound Investing

In Session 3 of the 2026 Bainbridge Community Foundation Spring Financial Education Series, Paul sits down with Mike Piper — CPA, Personal Financial Specialist, and the voice behind the Oblivious Investor blog and the free Open Social Security calculator — for one of the warmest, most practical conversations of the series. Mike has a rare gift: taking the topics that intimidate most investors and making them feel obvious. Over the course of the hour, he and Paul work through the handful of decisions that genuinely shape a retirement.
Mike opens with a quietly radical idea: if you've prepared well, "more than enough" isn't the exception — it's the most likely outcome. Because we have to plan for long lifespans, poor markets, and high medical costs that usually don't all come to pass, most disciplined savers end up with leftovers. From there, he explains which dollars to spend first each year, how age and capital gains should steer whether you draw from taxable or retirement accounts, and why the step-up in basis matters more than most people realize.
The conversation turns to the human side of money, too — how to talk a couple through it when one spouse is aggressive and the other can't stand the thought of the stock market, why both positions are almost always driven by fear, and how framing the trade-offs around the people you love often brings them closer together. Mike and Paul also tackle the spendthrift-child dilemma, the case for matching a young person's Roth IRA, and why small gifts early can dwarf an inheritance received at 70.
On Social Security, Mike makes the point that most people get the risk exactly backwards: delaying benefits isn't a gamble — it's insurance against the scary scenario of living a very long time. He walks through what really happens if Congress does nothing before the trust fund shortfall around 2033 (hint: the program doesn't disappear), and the range of fixes on the table. Throughout, both men return to the same theme — simple, low-cost, broadly diversified portfolios keep beating the clever alternatives, and the Bessembinder research helps explain why.
Stick around for the closing exchange on using AI to learn from the "Truth Tellers" — and Mike's cautionary tale about a chatbot that invented an entire tax-code provision, word for word and completely convincingly, that simply does not exist.
LINKS:
Mike Piper's blog — obliviousinvestor.com
Open Social Security — opensocialsecurity.com
Mike's books on Amazon — https://bit.ly/49BQugd
Oblivious Investor — https://bit.ly/4oeIacs
We're Talking Millions! (free PDF and audio) — https://www.paulmerriman.com/free-books
If You Can by Bill Bernstein (free PDF) — https://www.paulmerriman.com/free-books
PlanVision — Mark Zoril — planvisionmn.com
The Bessembinder study — "Do Stocks Outperform Treasury Bills?" https://www.morningstar.com/personal-finance/hendrik-bessembinder-do-stocks-outperform-treasury-bills

Watch the Video- https://www.youtube.com/watch?v=bB2ccYRLSOI&feature=youtu.be

In the final episode of the 2026 Boot Camp series, Paul Merriman sits down with Chris Pedersen and Daryl Bahls to tackle the last fork in the road every investor faces: how to and how much automation to use. After all the boot camp decisions — stocks versus bonds, which equity asset classes, how much fixed income, how to handle contributions and withdrawals — the final question is how much of the day-to-day management you should hand off to a tool, and which tool is right for you.
Chris walks through how M1 Finance “pies” let buy-and-hold investors put their portfolios on autopilot: automated contributions, on-the-fly rebalancing as new money comes in, fractional shares, and one-button rebalancing. He explains the pre-configured Merriman portfolios — the Ultimate Buy and Hold, Worldwide and US Four-Fund, All Value, All Small Cap Value, and the Aggressive Target Date glide path in five-year increments — and an important limitation: once you grab a pie, there’s no live link back to the source, so website updates won’t change your account.
Paul then makes the case for Fidelity’s Basket Portfolios as an alternative, especially for anyone uneasy about moving large sums to a younger company. He covers the flat $4.99-per-month fee regardless of account size, eligible account types, the TFLO short-term Treasury workaround for holding cash, and why Fidelity may fit investors already in the Fidelity ecosystem. The team compares trading windows, account minimums and how each firm counts the $10,000 threshold, and Daryl shares that M1 has grown from about $1 billion in 2020 to roughly $12.5 billion in assets under management.
The conversation closes with practical guidance on mixing and matching Sound Investing portfolios, the question everyone’s asking — “how long do I have to wait for small cap value?” — a reminder not to flail or chase recent performance, why the 10-fund Ultimate Buy and Hold strategy still stands, and a clear explanation of the move from AVUS to AVLC and where AVSC fits.
CHAPTERS
00:00 - Intro
03:10 - M1 Finance
13:45 - Fidelity Baskets
24:27 - Portfolio Combos
29:55 - When to Change Allocations
42:44 - AVLC vs. AVUS
45:15 - Outro
LINKS:
Sound Investing Portfolio Pies
M1 Finance Pie Tutorial (Mobile App)
M1 Finance Pie Tutorial (Web Interface)

In this interview from the 2026 Bainbridge Community Foundation Annual Financial Education Series, Paul sits down with Bill Bernstein — neurologist, financial historian, and author of The Four Pillars of Investing and If You Can — for a wide-ranging conversation drawn from 50-plus years of investing experience.
Bill explains why you're only rewarded for taking risk in well-regulated markets (and why crypto doesn't qualify), how today's market echoes the late 1990s, why the "reverse glide path" makes sense the older you get, and what the Bessembinder research really tells us about the cost of trying to pick winners. Paul and Bill also debate withdrawal strategies, the case against long bonds, and whether tilted small-value investing still works once "the bozos know about it."
A masterclass in evidence-based investing from one of the most respected voices in the field.
CHAPTERS
00:00 Intro from Matt Longmire, Bainbridge Community Foundation
02:50 Welcoming Bill Bernstein
03:50 Why The Four Pillars of Investing belongs on every DIY investor's shelf
05:50 Risk vs. reward — and why Bitcoin doesn't qualify
08:30 How many asset classes do you really need?
11:50 Where today's market resembles the late 1990s
13:40 Are REITs still worth holding?
15:50 The case for automating everything
19:45 Why retirees need to fear sequence-of-returns risk
21:30 Paul's 5% rule vs. the 4% rule
25:30 The two-bucket theory and the reverse glide path
27:30 Prediction markets, gambling, and "being the house"
32:00 The sociological signs of a bubble
35:00 Speculation vs. gambling — gold's real return
40:00 The Bessembinder study: why 4% of stocks make most of the returns
46:00 Why rich people plan three generations ahead
49:00 Audience Q&A
58:30 Tilted index funds (DFA, Avantis) — worth it?
01:03:50 The future of Social Security
01:07:00 Closing thoughts and book recommendations
LINKS:
The Four Pillars of Investing — Bill Bernstein (2nd ed., 2023)
If You Can — Free PDF from Bill Bernstein
The Bessembinder Study — "Do Stocks Outperform Treasury Bills?"
Bainbridge Community Foundation
Ben Carlson's New Book on Risk and Reward

Chris and Paul explain what target-date funds are and do, and how to augment them with some small-cap value to get the broad diversification benefits of the other Sound Investing portfolios.
They describe several approaches and tools investors can use to determine what might be best for them.

CHAPTERS
00:00 Intro
03:03 Target-Date Funds
07:00 Glide Paths
15:17 TDF Backtesting
19:55 TDF Weaknesses
26:20 "Easy" 2FFL
34:46 "Moderate" 2FFL
37:48 "Aggressive" 2FFL
41:00 Customizer
52:15 Calculator
61:07 Books
66:00 Outro
LINKS:
Wharton: Target Date Funds & Portfolio Choice in 401(k) Plans
Morningstar: “2026 Target-Date Fund Landscape”
Chris' Tables of 2 Funds for Life and Target Date Funds (PDF)

Paul sits down with Chris Pedersen and Daryl Bahls for the first Q&A session in months — and this one is built around the questions readers and listeners ask most often. Chris and Daryl share what they're working on next (Best-in-Class ETF updates, Target Date Fund work, telltale charts, risk-adjusted return analysis), Paul talks about a smarter way to use AI for the questions outside our wheelhouse, and the team works through six reader questions about portfolio design — from combining model portfolios to choosing between fund families.
If you've ever wondered whether your portfolio is "right," this conversation will help you think about it the way Chris and Daryl do.
8:30 — Should I combine the Worldwide Four Fund, U.S. Four Fund, and Worldwide All Value with a small cap value tilt?
16:00 — How do I read the Sound Investing tables to compare portfolios?
30:30 — Worldwide All Small Cap Value vs. the U.S. Two Fund — which is better?
38:15 — My Vanguard Four Fund uses VOO, VTV, VB, and VBR — am I using the right ETFs?
41:30 — How do Vanguard, Fidelity, Schwab, DFA, and Avantis compare on size and value exposure?
46:30 — How do I get help with Merriman portfolios when I need it?
Table B2 Table H2 Fine Tuning Tables Portfolio Configurator
You'll get the full answers, the data behind them, and Chris and Daryl's reasoning by watching or listening.
Watch the video here- https://youtu.be/BdTNOkALpuQ