What Is Investment Coaching?

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The most expensive lesson plan in Claremont history

Before I tell you what investment coaching is, you should know who's writing this.

I have a PhD in finance. I taught finance at the Claremont Colleges and at Ivey Business School. I worked as chief economist at a hedge fund and did due-diligence consulting for UHNW clients. And I sold Nvidia too early because I felt nervous.

As a PhD student preparing to teach my first behavioral finance course, I figured my students would want war stories. So I took out student loans and invested the entire sum in individual stocks. The plan was to make a few small, instructive mistakes I could turn into compelling lecture material.

The plan worked, but the mistakes weren't small.

One of my early buys was a chipmaker called Nvidia. It ran up fast and I sold most of my shares for a quick profit. I remember thinking, "This is so easy." Nothing had changed about the company. I just wanted to lock in the gain.

Those shares would be worth roughly $3 million today.

The part that still stings is that I was teaching this exact mistake that semester. Selling winners too early from risk aversion is one of the best-known findings in behavioral finance. I could have lectured on it from memory, but knowing about it didn't help one bit in practice.

Years later NBC wrote the story up. So did Yahoo! Finance. Search "amos nadler finance nvidia" and enjoy yourself.

I've made my peace with it, mostly, by talking about it with a finance colleague on a makeshift podcast and posting it on LinkedIn.

Fast-forward to today. I’m now offering behavioral economics-informed investment coaching to help people avoid the big avoidable errors leveraging technology developed at Prof of Wall Street with a supportive, high-touch coaching program.

Investment coaching is human support for big decisions. A coach looks at what you did, measures where your process and decisions help or hurt your performance, and works with you to improve and take charge of your portfolio.

My approach leverages decision neuroscience and quantitative finance to give you a human connection with clear, quantitative feedback.

Athletes figured this out long ago. Michael Jordan once said the thing he was best at was being coachable. Serena Williams hired Patrick Mouratoglou after an early exit at the French Open. He worked on her tactics, footwork, and handling pressure, and she went on to win ten more Grand Slam singles titles.

When I lived in the Caribbean, I hired a surf coach. He surfed with me, filmed me, and debriefed with me. We worked on paddling, reading waves, pop-up speed, where to look down the line, and foot position in real time to correct long-standing bad habits. Just two hours later I was catching more waves with less frustration.

Serena and I have very little in common, but we both needed someone objective, watching closely, telling us what to fix and supporting us over time.

I didn’t invent investing coaching, but I am offering a materially better offering than anything I’ve seen that delivers quantifiable improvements to investors that were not possible a few years ago.

Why investors fly blind

Most investors and portfolio managers grade themselves on their returns. That number blends every decision ever made, good and bad, into a single figure but says nothing about how they got there.

Were you up because your thesis was strong, or because the whole market rose? Down because of bad luck, or because you keep selling winners and sitting on losers? The standard metrics can't tell you.

It gets worse once you sell. The stock vanishes from your account, so you never see what it did next.

An athlete who misses a shot watches the tape. An investor who makes a bad trade checks the balance, sighs, and moves on.

I used to think that it was “ego” that kept investors from seeking coaching, but what I’m learning is that people don’t know what investment coaching is in practice, that it actually works, and they can confidentially improve their performance and protect their wealth, funds, wealth practices, and their professional careers.

What an investing coach works on

Some firms offer direct psychological support to their traders, such as BlackRock’s London-based behavioral finance team, which analyzes trade blotters and decision logs to curb cognitive biases like the disposition effect and overconfidence.

Similar models exist across the industry: hedge funds like Point72 deploy dedicated performance coaches to manage stress and drawdown recovery, while platforms like Citadel and Millennium rely on data-driven audits to diagnose unforced execution errors. Smaller funds increasingly need this type of oversight to identify and neutralize the subtle behavioral patterns that reduce performance and create decision insecurity.

I have my own approach.

After looking at billions of dollars of real trading data, I've stopped thinking of "good investor" as a personality type. It comes down to executing specific skills and how repeatable is your decision workflow.

Here are a few critical skills:

Stock picking. Choosing what to own. It gets all the glory, and it's often the least broken part of the game. Terry Odean studied thousands of real brokerage accounts and found that, on average, the stocks people bought went on to underperform the stocks they sold.
Weighting your positions. Deciding how much to put in each position. Most people size by feel, which usually means by excitement. A humbling test: does your weighting beat a plain equal-weight portfolio? Most people have never checked.
Selling. Knowing when to get out. See above. Or search my name.
Buying the dip. Adding to a position after it falls. Sometimes that's smart. Sometimes it's loss chasing, where you buy more mainly to make a paper loss hurt less.
Managing winners and losers. We sell winners too early and hold losers too long. It shows up in retail accounts and among professional portfolio managers.

Each of these is a behavior you repeat, which means it can be measured. Once it's measured, it can be practiced and improved and skills can positively compound.

What investment coaching is not

A good investing coach doesn't tell you which stocks to buy any more than a coach steps onto the court to shoot the ball for you. No hot tips, no price targets, no model portfolio. They don’t try to take over your account or charge you management fees. That's investment advice, which is a different job with its own regulations, and it belongs with a licensed advisor.

Coaching sits underneath whatever you already do. You keep your accounts, your broker, and your strategy. The coach works on the decision process: how you build a thesis, size a position, decide to sell, and handle the urge to "lock it in." (I'm very familiar with that urge.)

What working with me looks like

It starts with an open conversation about your investing approach, portfolio size, goals, and coachability assessment. If there’s a good fit, your data serves as the “source of truth” about your investing decisions.

The Prof of Wall Street system breaks your performance down skill by skill and puts a dollar figure on what each one added or cost you to provide a baseline to work from.

Then we go through it together. Almost everyone has at least one area where they're excellent and have no idea. Almost everyone also has a blind spot that can improve their performance, which is the most meaty, exciting part of the analysis.

From there the work is practical. We pick the skills costing you the most and build a process around them: writing down your reasons before a trade, sizing rules, and sell criteria you set while calm instead of mid-panic.

One of the biggest insights of decision neuroscience is that breaking down a complex problem leads to better decision outcomes than contending with a complex set of questions simultaneously. The best way to get the most out of our brains is to work with the actual brains we have instead and building processes around how we execute best.

Over the following months we check your new decisions against the old pattern, so you can see whether it's changing.

All information is confidential and I work directly with individuals and firms.

If you manage other people's money

Professionals sometimes read this and other behavioral finance research and file it under "retail problems." Nope. I had extensive graduate training and derived the utility function underlying the disposition effect when I sold Nvidia. Credentials don't make anyone immune to biases and systematic mistakes–processes do.

The research agrees. A study of institutional portfolio managers, aptly titled "Selling Fast and Buying Slow," found that managers deploy significant effort into what they buy. Then they apply far less rigor to what they sell, and it costs them meaningfully.

Portfolio managers already get more measurement than most investors: performance reports, attribution, risk dashboards. Those describe what happened to the portfolio. They rarely show which of your own decision habits produced it. And very few firms invest in coaching their managers to get better at the core job.

Tiger Woods rebuilt his golf swing several times while he was already the best player in the world. The best performers keep getting coached after they reach the top.

For portfolio managers and investment teams, the work goes deeper. We run your trade history through the same skill analysis: picking, weighting, dip buying, selling, and the disposition effect. Then we audit the decision process itself and help you write it down clearly: how ideas get selected, how positions get sized, what triggers a sale, and how exceptions get handled. Wealth management firms can also use the analysis to evaluate a manager's skill before hiring.

Who is investment coaching for?

Coaching makes sense if you make your own investment decisions with real money and want to know whether you're any good at it. It's also for people who suspect they keep repeating a mistake but can't quite name it. And it's for professional portfolio managers who want to assess specific skills and see which parts of their process add value and which ones drag.

If you're certain you're already a flawless investor, feel free to skip it. I had that confidence once. It cost me roughly $3 million.

There are two ways to start. If you want to see your own numbers first, get the free Portfolio Snapshot, a quick look at where your returns actually came from. If you'd rather talk with a human about your process, head to Investing Coaching for Humans and get in touch with me.

If you manage money professionally or run an investment team, reach out to me directly and we'll build the work around your team's process and data.

Either way, you'll be learning from your own real data, market data, the entire canon of finance research, and if it helps, mine.

Selected citations

Shefrin, H., & Statman, M. (1985). The disposition to sell winners too early and ride losers too long: Theory and evidence. The Journal of Finance, 40(3), 777-790.

Odean, Terrance. "Are investors reluctant to realize their losses?." The Journal of finance 53.5 (1998): 1775-1798.

Akepanidtaworn, Klakow, et al. "Selling fast and buying slow: Heuristics and trading performance of institutional investors." The Journal of Finance 78.6 (2023): 3055-3098.

Hoffmann, Arvid OI, and Thomas Post. "Self-attribution bias in consumer financial decision-making: How investment returns affect individuals’ belief in skill." Journal of Behavioral and Experimental Economics 52 (2014): 23-28.

Kahneman, D., & Tversky, A. (1979). Prospect Theory: An Analysis of Decision under Risk. Econometrica, 47(2), 263-291.

Barber, B. M., & Odean, T. (2000). Trading Is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors. The Journal of Finance, 55(2), 773-806.

Thaler, R. H. (1985). Mental Accounting and Consumer Choice. Marketing Science, 4(3), 199-214.

Loewenstein, G. F., Weber, E. U., Hsee, C. K., & Welch, N. (2001). Risk as Feelings. Psychological Bulletin, 127(2), 267-286.

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