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At The Money15 July 2026

At The Money:  When Should Do-It-Yourself Investors Fire Themselves?

4Frameworks
7Insights

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Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster

Frequent Portfolio Attention Is Not the Same as Investment Skill

Constantly entering and exiting positions may look engaged, but Grummit treats it as a warning sign for overconfidence and FOMO. A disciplined investor is more likely to set an allocation, leave it alone, and review it periodically.

  • Frequent trading can reflect overconfidence rather than expertise.
  • FOMO encourages reactive decisions.
  • Multiple individual positions do not guarantee diversification or skill.
  • Reviewing every six to twelve months is more consistent with a long-term plan.

“You're falling into the trap of FOMO, right? You're starting to fear missing out.”

Dr. Jordan Grummit

“if you're setting and forgetting it and maybe evaluating every six to 12 months, you're probably on the right track.”

Dr. Jordan Grummit
#overconfidence#fomo#trading#investor behavior

Hot Take· 1

Hot Take

Experienced DIY Investors May Be More Complacent Than Reckless

Where young investors often chase alpha, mature investors may become too certain that yesterday's successful strategy will work indefinitely. Grummit remains committed to index funds while arguing that investors should monitor structural change without reacting to every market fluctuation.

  • Experience can create complacency.
  • A sound strategy should not become unquestionable dogma.
  • Monitoring change does not require frequent portfolio changes.
  • Older investors should prioritize risk modification.

“Now, as you get older, believe it or not, I think the bigger problem in really mature DIY investors is you get complacent.”

Dr. Jordan Grummit

“That doesn't mean I'm changing things. That doesn't mean I'm reacting to little changes in the market.”

Dr. Jordan Grummit
#complacency#index funds#risk management#decumulation

Explainer· 2

Explainer

Why Young Investors Can Usually Manage Accumulation Themselves

Grummit argues that early accumulation is forgiving because investors have time and room to recover from errors. A basic understanding of markets, index investing, and a written investment plan may be enough, provided the investor can remain calm during declines.

  • Accumulation offers more room for error than decumulation.
  • Young investors should understand markets and index investing.
  • A written investor plan supports disciplined behavior.
  • Panic selling is an immediate sign that help may be needed.

“when you are young and you're in the accumulation phase, it's almost hard to mess up, right?”

Dr. Jordan Grummit

“anyone who's going to sell the minute the stock market drops on any given day probably needs financial advice right away.”

Dr. Jordan Grummit
#accumulation#index investing#diy investing#behavior
Explainer

Why Decumulation Changes the Investment Objective

During accumulation, investors can emphasize long-term returns and tolerate volatility. In decumulation, Grummit shifts the priority toward limiting severe losses, even when that means accepting a return below the overall market.

  • Decumulation increases sensitivity to losses.
  • Risk modification can matter more than maximizing returns.
  • Below-market returns may be acceptable when downside is reduced.
  • Investment objectives should change with life stage.

“We're really talking about risk modification. So I'm not as worried about returns as I used to be. I'm worried about losses.”

Dr. Jordan Grummit

“I want to modify my risk in such a way that I don't have those really deep losses anymore.”

Dr. Jordan Grummit
#decumulation#loss prevention#returns#retirement

Story· 1

Story

When “Low-Risk” Multifamily Syndications Go to Zero

Grummit uses multifamily syndications as an example of alternative investments whose risks were understated during favorable conditions. Some investors pursued apparent alpha on the belief that these deals offered high returns with little work or risk, only to suffer total losses.

  • Alternative assets can hide severe downside risk.
  • Recent success can reinforce overconfidence.
  • Claims of low work and low risk deserve skepticism.
  • Some concentrated investments can lose everything.

“Very little work, very little risk. And what are we seeing now? We're seeing some of these go to zero.”

Dr. Jordan Grummit

“Literally, people are losing everything.”

Dr. Jordan Grummit
#real estate#syndications#alternative assets#risk

Takeaway· 2

Takeaway

Concentrate Risk in Your Career, Not Your Stock Portfolio

Building wealth often requires concentrated effort in a career, business, or side hustle. Grummit warns that nonprofessionals should not compound that concentration by trying to generate stock-market alpha through narrow positions and frequent trading.

  • Career and business growth naturally concentrate personal risk.
  • Stock-market concentration is usually unnecessary for nonprofessionals.
  • Alpha seeking can signal overconfidence.
  • Broad market exposure captures beta without constant decisions.

“What you don't want to be doing unless you're a professional is concentrating risk in the stock market.”

Dr. Jordan Grummit

“So overconfident people seek alpha, right?”

Dr. Jordan Grummit
#risk#alpha#beta#portfolio concentration
Takeaway

DIY Investing Requires a Plan, Discipline, and Behavioral Control

Barry Ritholtz summarizes the core requirements for successful self-management: create a plan, follow it consistently, and prevent market stress from changing behavior. Grummit agrees that these controls make DIY investing reasonable during simpler phases of life.

  • Write down a plan before markets become stressful.
  • Discipline matters more than constant tactical activity.
  • Investors must manage their own reactions during downturns.
  • Behavioral weakness can outweigh technical knowledge.

“You have to have a plan, you have to be disciplined. And when things start to head south, you must manage your own behavior.”

Barry Ritholtz

“No, I think it's a and a beautiful assessment of how things should be.”

Dr. Jordan Grummit
#discipline#investment plan#market downturns#behavior