Overview of At The Money: When Should Do-It-Yourself Investors Fire Themselves?
In this Bloomberg At The Money episode, Barry Ritholtz speaks with Dr. Jordan Grumet (“Doc G”) about when self-directed investors should stop managing everything alone and bring in professional help. The conversation focuses on the difference between simple investing during the wealth-building years and the more complicated decisions that arise later in life, especially around retirement, spending, taxes, inheritance, and emotional life events. The core message: DIY investing can work well, but only if you have a plan, discipline, and the self-awareness to know when your situation has outgrown your own expertise.
Main Takeaways
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DIY investing is often fine during accumulation
For younger investors building wealth, simple habits like buying index funds regularly and staying the course are usually enough. -
The biggest risk for DIY investors is behavior, not knowledge
Panic-selling, chasing returns, and reacting to short-term market moves can do more damage than a lack of technical skill. -
Overconfidence is a major red flag
Investors who constantly trade, chase “alpha,” or jump in and out of positions may be taking unnecessary risks. -
The shift from accumulation to decumulation is a major inflection point
Turning savings into retirement income is more complex and is one of the strongest reasons to seek professional advice. -
Financial advice should be holistic, not just mathematical
Good advisors should ask about life goals, family, travel, work, health, and trade-offs—not just net worth targets.
When DIY Investing Works Best
Young investors in the accumulation phase
Grumet argues that for many people early in their financial journey, it’s hard to “mess up” if they:
- keep saving consistently,
- invest in broadly diversified index funds,
- avoid emotional decisions,
- and stick to a long-term plan.
This stage is often manageable without professional help, as long as the investor can tolerate volatility and not panic when markets fall.
Simple, disciplined behavior
A DIY approach works best when the investor can:
- set a clear plan,
- review portfolios infrequently rather than obsessively,
- ignore daily market noise,
- and avoid trying to outguess the market.
Red Flags That It’s Time to Bring in Help
1. Emotional decision-making
If market drops, retirement, divorce, death, or an inheritance trigger intense emotional reactions, professional guidance can help prevent costly mistakes.
2. Chasing alpha
Signs of overconfidence include:
- frequent trading,
- buying and selling based on headlines,
- concentrating too much in individual stocks,
- and believing you can consistently beat the market.
3. Complexity increases
Advice becomes more valuable when decisions affect:
- tax brackets,
- Roth conversions,
- health care subsidies,
- planning for a disabled child,
- estate and inheritance planning,
- or other situations where the room for error is small.
4. The world or your life has changed
A DIY strategy that worked for years may no longer fit if:
- you’re retiring,
- selling a business,
- receiving a large inheritance,
- or moving from saving to spending.
Why Decumulation Is So Hard
One of the episode’s most interesting ideas is that many wealthy people struggle to spend money even when they can easily afford it.
“Escape velocity”
Grumet suggests that the real purpose of wealth may not be to maximize spending, but to create enough freedom to leave a life you don’t want and build one you do want.
Why people underspend
He points to a few reasons:
- Security feels good — a large cash cushion creates comfort and identity.
- Money is often tied to fear — people fear running out more than they value extra enjoyment.
- Spending is psychological, not just financial — even very affluent people may hesitate to buy a car, take a trip, or spend on themselves.
A practical workaround
He describes approaches like:
- setting up a “paycheck” from bonds, annuities, Social Security, or withdrawals,
- creating a separate “fun bucket,”
- or simply deciding in advance how much can be spent guilt-free.
The point is to make spending feel structured and safe.
What Good Financial Advice Should Look Like
Grumet compares financial advice to medical diagnosis: good advice should look at the whole person, not just the symptom.
Better advisor questions
Instead of asking only about net worth goals, advisors should ask:
- What are your goals?
- What do you want your life to look like?
- Who matters most to you?
- What are your must-haves?
- What trade-offs are you willing to make?
- Do you want to retire earlier, or work longer and enjoy more now?
The advisor’s role
A good advisor may:
- review your work,
- offer hourly advice,
- help with a specific transition,
- or fully manage a complex portfolio.
It does not have to be all-or-nothing.
Notable Insight
“This is not a math problem. It’s a brain problem.”
That line captures the episode’s main theme: many financial challenges are behavioral and emotional, not purely analytical.
Bottom Line
DIY investing is often effective when you’re young, disciplined, and focused on simple long-term accumulation. But as life gets more complex—or when emotions, taxes, or retirement income planning enter the picture—professional help can be worth it. The key is not whether you can do it yourself, but whether doing it yourself still makes sense for where you are now.