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Learning AI

Many of us are not sure how to use AI. This series of posts is intended to show you the different ways AI can augment your intellectual capabilities. Whether it’s a simple question (like this week’s post) or a more complex challenge, we will test AI and see how it can work to give you a problem-solving advantage.

A diverse set of topics will be covered, but most importantly, we will publish the actual AI dialogue so you can see how it all works.

Each week, we will select two of the AI engines and pose a question or a problem, summarize the findings in our own words, and include the interactions with the AI for your review.

Please email me concepts you would like to see tested.

Does crime pay?

We posed the question, “Does crime pay?” to Google Gemini and ChatGPT.

Both AIs agreed that in the short run, a successful criminal may see economic and social benefits. In the long run, the answer from both was a resounding “No.”

Interesting factors like lost career time due to incarceration and the stigma of a criminal record were cited as career and earnings killers.

Other non-economic factors like family strain and psychological damage were mentioned.

It was also noted that only a select few at the top of a criminal enterprise benefit over time – as long as they are not caught!

Highlights from my discussions with the AI:

1. The Pay Cut: Statistics show that individuals who have been incarcerated earn roughly 52% less over their lifetime compared to socioeconomically similar peers who haven't.

2. Missing Years: Time spent in jail is time spent not gaining skills, seniority, or networking in the legitimate economy. A 5-year sentence at age 25 can cost someone roughly $500,000 to $1,000,000 in lost lifetime earnings.

3. White-collar crime. While it yields big payoffs, chances of success are low.

4. Bosses win. There is too much competition at the lower levels of crime organizations, but the bosses consistently make bank.

Fascinating Findings

• Most lower-tier drug dealers still lived with their moms.

• ChatGPT concluded its session by asking for the motivation behind my question and if it could help solve deeper issues of unhappiness that I might be experiencing.

• Survivorship bias hides the overwhelming majority who lost everything.

Flip through the full text of the dialogues below and participate in the one-question poll at the end.

Response from Google Gemini

Does crime pay?

Statistically and economically, the short answer is no. While movies often focus on the "big score," the reality of a criminal career is usually one of persistent financial instability and long-term poverty.¹

For most people, crime functions like a high-risk, low-reward job with no retirement plan or insurance.

📉 The "Criminal Wage" Reality

Research into the economics of crime shows that for the average person involved in illegal activity, the "pay" is surprisingly low:

• Below Minimum Wage: A landmark study by economist Steven Levitt (author of Freakonomics) found that most low-to-mid-level drug dealers actually lived with their mothers because they earned less than minimum wage.

• The "Scab" Effect: Because there are no barriers to entry for many street-level crimes, the "market" is often oversaturated, which keeps profits thin for everyone except the very top of an organization.

• High "Business Expenses": Criminals often have to pay for protection, "taxes" to gangs, or overpriced goods because they cannot access legal markets.

💸 The Lifetime Earnings "Scar"

The real financial cost of crime isn't just the risk of prison—it's what happens to your ability to make money after you get caught.

1. The 50% Pay Cut: Statistics show that individuals who have been incarcerated earn roughly 52% less over their lifetime compared to socioeconomically similar peers who haven't.

2. Missing Years: Time spent in jail is time spent not gaining skills, seniority, or networking in the legal economy. A 5-year sentence at age 25 can cost someone roughly $500,000 to $1,000,000 in lost lifetime earnings.

3. The "Record" Barrier: In 2026, background checks are more automated and thorough than ever. A criminal record often disqualifies you from high-paying fields like finance, healthcare, and law, forcing you into "secondary" labor markets with lower pay and no benefits.²

⚖️ The Risk vs. Reward Problem

Economists view crime through the lens of Expected Utility. To be "worth it," the reward must outweigh the probability of getting caught multiplied by the severity of the punishment.

The Math of Crime:

If a robbery nets you $5,000 but has a 20% chance of a 5-year prison sentence, you are essentially "selling" 5 years of your life for $25,000 ($5,000 ÷ 0.20). That is a "salary" of $5,000 per year of freedom.3

🏦 Is White-Collar Crime Different?

While high-level fraud or embezzlement can yield millions, the "success" rate is still low:

• Complexity: These crimes require high levels of education and access—skills that would typically earn someone a high salary in the legal world anyway.

• Clawbacks: In 2026, asset seizure laws are extremely aggressive. Even if you aren't jailed, the government can seize your home, cars, and bank accounts, often leaving you "bankrupt and barred" from ever working in a high-level position again.

🏁 Summary

The "glamorous criminal" is a statistical outlier. For 99% of people, the most reliable way to build wealth in 2026 remains compounding interest and specialized skills in the legal economy.

Are you interested in seeing which legal career paths currently offer the best balance of low risk and high financial reward?

Response from ChatGPT

Does crime pay?

Short answer: crime can pay in the short term — but it almost never pays in the long term.

Here’s the clear, unsentimental reality.

💰 How crime can “pay” (briefly)

• Immediate gains: Theft, fraud, drug sales, and financial crimes can produce fast money

• Low-skill access: No credentials or long lead time required

• Uneven enforcement: Some people get away with it for a while

This is why crime exists — the short-term incentives can be real.

📉 Why crime almost never pays over time

1. Expected value is negative

Even when crimes succeed:

• Confiscation, fines, and restitution erase gains

• Legal costs are massive

• Time lost to incarceration has real economic value

Over time, probability catches up.

2. Permanent downside risk

• Criminal records reduce lifetime earnings

• Loss of professional licenses

• Travel, housing, and credit restrictions

One mistake can permanently cap future income.

3. Compounding consequences

• Escalation to higher-risk crimes

• Exposure to violence

• Blackmail and betrayal risk

• Stress and paranoia

Legal income compounds; criminal income decays.

4. Social and personal costs

• Family strain

• Reputation damage

• Limited mobility

• Psychological toll (constant threat, lack of trust)

These don’t show up on a balance sheet — but they matter.

📊 The rare exceptions people point to

People often cite:

• Organized crime leaders

• Large-scale financial criminals

• Those who “got away with it”

These are statistical outliers, not models. Survivorship bias hides the overwhelming majority who lost everything.

🧠 The deeper truth

Crime tends to attract people who:

• Are desperate

• Discount the future heavily

• Overestimate their skill and luck

That combination guarantees poor long-term outcomes.

Bottom line

Crime can produce short-term cash, but it destroys long-term wealth, freedom, and optionality.

If the question behind this is really about:

• Economic pressure

• Lack of opportunity

• Frustration with “the system”

There are legal ways to improve outcomes without risking everything.

If you want, we can talk through:

• High-upside legal paths with low barriers

• How people transition out of risky situations

• Building income when options feel limited

Just tell me what’s driving the question.