Learning from Failures and Engineering Finance

In this episode we answer emails from Midwest Nice, Ron and Stefan.  We discuss helping a cautious parent with a high-fee advisor, what services are actually worth paying for in their case, how to invest home-sale proceeds for a 5–10 year horizon, where to learn beyond basic indexing without losing the plot, the McKenna Man portfolio, and best approaches to try to beat the market (beyond don't try). 

Links:

Father McKenna Center Donation Page:  Donate - Father McKenna Center

Excess Returns Channel: Excess Returns - YouTube

Tacoma Narrows Bridge Collapse Video:  Tacoma Bridge Collapse: The Wobbliest Bridge in the World? (1940) | British Pathé

Stefan's Sparkline Capital Article:  Buffett's Intangible Moats

Ben Felix Video On Leverage:  Investing With Leverage (Borrowing to Invest, Leveraged ETFs) (youtube.com)

Book List:

Ashvin Chhabra:  "The Aspirational Investor"

J. David Stein:  "Money For The Rest of Us"

Michael Mauboussin:  "More Than You Know" and "Think Twice"

Antti Ilmanen:  "Expected Returns" and "Investing Amid Low Expected Returns"

Andrew Lo:  "In Pursuit of the Perfect Portfolio"

Ed Thorpe:  "A Man For All Markets"

Larry Swedroe:  "Your Complete Guide to Factor Investing"

Breathless Unedited AI-Bot Summary:

Ever tried to help a parent who’s financially fine but glued to a “nice” advisor and a vague plan? We dig into the real-world tactics that preserve relationships while improving outcomes—think gentle on-ramps like scam protection, account alerts, and sharing your own planning choices. The goal isn’t to win a debate; it’s to earn access, reduce avoidable taxes, and align risk with comfort, especially when pensions and Social Security already cover spending.

From there, we get specific about value. If an advisor stays, the highest-return work for many retirees is tax strategy, asset location, and simplification—not performance theater. We talk practical setups like Wellington or Wellesley for low-cost balance, when a deferred QLAC can be a comfort hedge, and why generating more income than you need can backfire at tax time. For listeners sitting on house-sale proceeds with a 5–10 year window, we unpack why hoarding cash invites erosion and why a golden ratio–style mix can cap drawdowns to a few years while keeping growth and inflation resilience alive.

Curious investors also get a roadmap for learning beyond slogans. We highlight factor tilts with quality screens, institutional-grade thinkers like Ilmanen, Lo, and Mauboussin, and the simple truth that outperformance usually comes from concentration or leverage—so position sizing and behavior matter more than hot takes. We challenge the myth that a cap-weight index buys the “whole economy,” and we favor building like engineers: learn from failures, control volatility, and design for the stress you’ll actually feel.

If this helped you rethink fees, timelines, or tilts, follow the show, share it with a friend, and leave a quick review so more DIY investors can find these tools.

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