AI Investor Assessment · 18 questions · about 5 minutes
What kind of AI investor are you?
Three short parts: how far along you are with AI investing, how you behave when markets move, and which part of the AI stack suits you. You’ll get one of 30 profiles, the blind spot that comes with it, the mental models from the book to focus on, and guardrails that fit how you behave.
Every score is shown at the end, so you can see how we got there. Want the lay of the land first? See all 30 profiles.
Part 1 of 3 · Maturity
How far along are you?
Seven questions place you on one of five levels of AI investing maturity. There are no wrong answers: the level only decides which tools and next steps make sense for you.
Level 1Curious. You know AI matters and may own an obvious name or two, but you're still learning the vocabulary.
Level 2Informed. You follow AI investing, own several names and know the stack has layers, but you mostly rely on other people's analysis.
Level 3Analytical. You judge companies on fundamentals and unit economics, use primary sources, and hold a thesis for each position.
Level 4Specialist. You've gone deep on particular layers or sectors, read transcripts every quarter, and follow a written, tracked process.
Level 5Insider. You work in AI or invest in it privately, and see technical and commercial shifts before they're public.
Educational only, not investment advice. Nothing here recommends buying or selling any security. Disclosure: this is Rob May’s site, and his book, newsletter, research and briefing services appear in the results. Other tools, including Chaikin Analytics products, are listed for what they do.
How the assessment works
Most investing quizzes ask one question: how much risk can you take? This one asks three, because AI investing goes wrong in three different ways. People take on more than their knowledge supports, they let fear or excitement drive decisions in a market that moves faster than most, and they pick a style that doesn’t fit their time or temperament. The assessment has 18 questions in three parts, one for each of those, and combines them into one of 30 profiles.
It is built on Rob May’s book, Investing in AI: Six Mental Models to Tell Moats from Traps, and on established research in behavioral finance. It is educational: it doesn’t ask about your finances, recommend securities or tell you how much to invest. What it gives you is a clearer picture of where you are, what tends to trip up people like you, and which ideas from the book to work on first.
Part 1: maturity, five levels
Seven questions about what you know and how you research place you on one of five levels: Curious, Informed, Analytical, Specialist, Insider. Curious: You know AI matters and may own an obvious name or two, but you're still learning the vocabulary. Informed: You follow AI investing, own several names and know the stack has layers, but you mostly rely on other people's analysis. Analytical: You judge companies on fundamentals and unit economics, use primary sources, and hold a thesis for each position. Specialist: You've gone deep on particular layers or sectors, read transcripts every quarter, and follow a written, tracked process. Insider: You work in AI or invest in it privately, and see technical and commercial shifts before they're public. The level decides which tools and next steps make sense; there is no wrong answer, and most investors never need to reach the top.
Part 2: behavior, four types
Six questions place you on two axes: whether you tend to act or wait, and whether your mistakes come more from feelings or from facts. The four combinations are behavioral investor types from Michael Pompian’s research. Preserver (passive + emotional): Puts safety first and feels losses sharply. Tends to hold losing positions, avoid change and stick with the familiar. Follower (passive + cognitive): Takes cues from advisers, friends and popular opinion more than from a plan of their own. Tends to chase what has recently worked. Independent (active + cognitive): Does their own research and trusts their own analysis. Tends toward confirmation bias: looking for evidence that agrees with them. Accumulator (active + emotional): Confident and comfortable with risk, often having built wealth by taking it. Tends to overconfidence, concentration and trading too much. Your type sets the guardrails in your result: the rules that protect you from your own most likely mistake.
Part 3: approach, six ways to invest in AI
Five questions match you to the way of investing in AI that suits your time, risk and conviction. Infrastructure Investor: Own the compute layer: the picks and shovels of the AI build-out. Core AI Investor: Established companies with real AI moats, not AI theater. Expansion AI Investor: AI-native companies creating entirely new categories. Thematic Rotator: Rotate between AI sub-sectors as capital and attention move. Tactical Trader: Catalyst-driven and dislocation-focused, often with options. Basket Investor: Diversified AI exposure through ETFs, indexes and rules. Each one connects to an idea in the book, and your result explains which.
What your result tells you
Your result names your profile, for example a particular behavioral type at a particular level within one of the six approaches, and explains what that combination is good at and where it is vulnerable. It lists the mental models from the book to focus on first, with links to each one, and a set of guardrails written for your behavioral type.
It also suggests a set of tools for your level and approach, starting with free ones. Prices are shown only where the vendor publishes them, and you don’t need any paid tool to invest well. Every score is shown at the end, so you can see exactly how the quiz reached its answer and disagree with it if you think it got you wrong.
The six mental models behind it
The six mental models from the book run through every profile: (1) AI is a collection of technologies: defensibility matters more than paradigm. (2) AI challenges SaaS assumptions: pricing and unit economics are being rewritten. (3) Expect major dislocations: one result can reprice a whole layer overnight. (4) AI changes markets and strategy: moats move to new choke points. (5) AI companies scale faster, but revenue quality beats revenue quantity. (6) Be careful evaluating AI COGS: margins can improve or deteriorate. Each profile emphasizes the two or three that matter most for its approach. Infrastructure investors, for example, are pointed to the ideas about defensibility and moving choke points, while tactical traders are pointed to the idea that a single result can reprice a whole layer of the market.
If you want to go further than the quiz, the AI stack map shows how the six approaches look in companies’ actual filings: which layers are earning money from the AI build-out, which are financing it, and where the risks sit.
The map
Three dimensions, thirty profiles
Every profile is a maturity level (the rows, from Curious at the bottom to the most advanced at the top) combined with an investment approach (the columns), which makes thirty. Pick any square to see who that profile describes, its edge, its blind spot, where to start and the mental models from the book that matter most for it.
You've heard Nvidia is "the AI stock" and bought some. You want the obvious winners but aren't sure how to think beyond that.
Edge: You're not chasing hype. Infrastructure is a real moat.
Blind spot: You may not know the difference between training chips, inference chips, memory and networking, so a cyclical downturn could catch you off guard.
Where to start: Read Rob's book and subscribe to the free newsletter. Learn the vocabulary before adding positions.
Level 1, Curious. You know AI matters and may own an obvious name or two, but you're still learning the vocabulary.
Infrastructure Investor. Own the compute layer: the picks and shovels of the AI build-out. Closest to what the book calls selling what AI consumes: you own the chips, power and cloud capacity every AI product needs.
Mental models to focus on
#1 AI is a collection of technologies: defensibility matters more than paradigm.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
You own Nvidia plus some mix of AMD, TSMC, the hyperscalers and maybe the utilities powering data centers.
Edge: You see that the stack has layers and spread your exposure across them.
Blind spot: You may be concentrated in training-era winners. Inference economics will matter more over time, and the winners could change.
Where to start: Rob's newsletter, plus a screening tool to check additions before you make them.
Level 2, Informed. You follow AI investing, own several names and know the stack has layers, but you mostly rely on other people's analysis.
Infrastructure Investor. Own the compute layer: the picks and shovels of the AI build-out. Closest to what the book calls selling what AI consumes: you own the chips, power and cloud capacity every AI product needs.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
You understand the full stack (chips, memory, networking, cooling, power, cloud, inference hardware) and hold 8–15 names across it.
Edge: You see the whole value chain and can anticipate where margin pressure lands next.
Blind spot: You may underweight the application layer and miss where value moves as the stack commoditizes.
Where to start: Rob's premium newsletter plus a fundamentals tool for stack-wide financials.
Level 3, Analytical. You judge companies on fundamentals and unit economics, use primary sources, and hold a thesis for each position.
Infrastructure Investor. Own the compute layer: the picks and shovels of the AI build-out. Closest to what the book calls selling what AI consumes: you own the chips, power and cloud capacity every AI product needs.
Mental models to focus on
#4 AI changes markets and strategy: moats move to new choke points.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
You've gone deep on one or two layers (inference chips, data center REITs, power) and read earnings transcripts every quarter.
Edge: Primary-source work puts you ahead of generalists.
Blind spot: Depth in one layer can blind you to dislocations next door.
Where to start: Transcript search, and the company pages on this site for the filings behind each layer.
Level 4, Specialist. You've gone deep on particular layers or sectors, read transcripts every quarter, and follow a written, tracked process.
Infrastructure Investor. Own the compute layer: the picks and shovels of the AI build-out. Closest to what the book calls selling what AI consumes: you own the chips, power and cloud capacity every AI product needs.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
#4 AI changes markets and strategy: moats move to new choke points.
You work in or near AI infrastructure and see what's really happening with capex, inference costs and chip roadmaps.
Edge: You see technical shifts 6–12 months before public commentary does.
Blind spot: Being close to the technology can make you underestimate how long markets take to reprice. Being right is easier than timing.
Where to start: The AI in NYC dinner series (by invitation) and a briefing with Rob and Vik to pressure-test your thesis.
Level 5, Insider. You work in AI or invest in it privately, and see technical and commercial shifts before they're public.
Infrastructure Investor. Own the compute layer: the picks and shovels of the AI build-out. Closest to what the book calls selling what AI consumes: you own the chips, power and cloud capacity every AI product needs.
Mental models to focus on
All six.
Profile 2.1 · Level 1 Curious · Core AI Investor
The "Which Big Companies?" Investor
You own some mega-caps and want to know which ones really benefit from AI and which just say "AI" on earnings calls.
Edge: You prefer established businesses, a sensible starting posture.
Blind spot: Mentioning AI isn't the same as having an AI moat. Many companies you own may be AI-exposed, not AI-advantaged.
Where to start: Rob's book, starting with how to evaluate traditional companies adopting AI.
Level 1, Curious. You know AI matters and may own an obvious name or two, but you're still learning the vocabulary.
Core AI Investor. Established companies with real AI moats, not AI theater. Built on the book's Core AI: AI that makes a company better at what it already does best. The trap to avoid is Commoditized AI, table stakes everyone deploys.
Mental models to focus on
#2 AI challenges SaaS assumptions: pricing and unit economics are being rewritten.
#4 AI changes markets and strategy: moats move to new choke points.
Profile 2.2 · Level 2 Informed · Core AI Investor
The AI-Powered Blue-Chip Buyer
You own established software and platform companies because they're building AI into their core products.
Edge: You're betting on execution and distribution, which are proven value drivers.
Blind spot: It's hard to tell which incumbents will extend their moat with AI and which will be disrupted. Early signals are easy to misread.
Where to start: Rob's premium newsletter plus a monthly conviction-pick service.
Level 2, Informed. You follow AI investing, own several names and know the stack has layers, but you mostly rely on other people's analysis.
Core AI Investor. Established companies with real AI moats, not AI theater. Built on the book's Core AI: AI that makes a company better at what it already does best. The trap to avoid is Commoditized AI, table stakes everyone deploys.
Mental models to focus on
#2 AI challenges SaaS assumptions: pricing and unit economics are being rewritten.
#5 AI companies scale faster, but revenue quality beats revenue quantity.
Profile 2.3 · Level 3 Analytical · Core AI Investor
The Moat Analyst
You check whether a company's AI features are genuine moats, table stakes or lottery tickets, and you track AI-driven revenue, retention and margins.
Edge: You use data to separate Core AI, which compounds, from Commoditized AI, which is a trap.
Blind spot: Analysis paralysis. The time to buy is often before the moat is fully proven.
Where to start: Rob's full framework plus fundamentals and transcript tools.
Level 3, Analytical. You judge companies on fundamentals and unit economics, use primary sources, and hold a thesis for each position.
Core AI Investor. Established companies with real AI moats, not AI theater. Built on the book's Core AI: AI that makes a company better at what it already does best. The trap to avoid is Commoditized AI, table stakes everyone deploys.
Mental models to focus on
#2 AI challenges SaaS assumptions: pricing and unit economics are being rewritten.
#4 AI changes markets and strategy: moats move to new choke points.
Profile 2.4 · Level 4 Specialist · Core AI Investor
The Sector-Depth Specialist
You've picked 2–3 sectors (enterprise software, cybersecurity, fintech) and track AI adoption inside them obsessively.
Edge: You can tell which incumbents are building real AI capability and which are buying startups for optics.
Blind spot: Conviction in a sector can slow you down when value moves elsewhere.
Where to start: The AI in NYC dinner series (by invitation) for ground truth from enterprise AI leaders.
Level 4, Specialist. You've gone deep on particular layers or sectors, read transcripts every quarter, and follow a written, tracked process.
Core AI Investor. Established companies with real AI moats, not AI theater. Built on the book's Core AI: AI that makes a company better at what it already does best. The trap to avoid is Commoditized AI, table stakes everyone deploys.
Mental models to focus on
#2 AI challenges SaaS assumptions: pricing and unit economics are being rewritten.
#4 AI changes markets and strategy: moats move to new choke points.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
Profile 2.5 · Level 5 Insider · Core AI Investor
The Enterprise AI Insider
You work in enterprise AI and know which vendors companies actually deploy, not just pilot.
Edge: You see production deployments, not demos, and know which "AI revenue" is real.
Blind spot: Survivorship bias. The enterprises most willing to talk may not be typical.
Where to start: The AI in NYC dinner series (by invitation) and a briefing with Rob and Vik.
Level 5, Insider. You work in AI or invest in it privately, and see technical and commercial shifts before they're public.
Core AI Investor. Established companies with real AI moats, not AI theater. Built on the book's Core AI: AI that makes a company better at what it already does best. The trap to avoid is Commoditized AI, table stakes everyone deploys.
Mental models to focus on
All six.
Profile 3.1 · Level 1 Curious · Expansion AI Investor
The AI Stock Enthusiast
You're excited about pure-play AI names and want to catch "the next Nvidia".
Edge: You're looking where the biggest upside could be.
Blind spot: That's also where the most traps are. Many pure-play AI stocks are stories, not businesses.
Where to start: Read Rob's book, especially the parts on traps and lottery tickets, before you buy anything else.
Level 1, Curious. You know AI matters and may own an obvious name or two, but you're still learning the vocabulary.
Expansion AI Investor. AI-native companies creating entirely new categories. Built on the book's Expansion AI: new business lines AI makes possible, which behave like lottery tickets the market often misprices.
Mental models to focus on
#1 AI is a collection of technologies: defensibility matters more than paradigm.
#5 AI companies scale faster, but revenue quality beats revenue quantity.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
Profile 3.2 · Level 2 Informed · Expansion AI Investor
The Pure-Play Portfolio Builder
You own 3–5 AI-native public companies and are looking for more.
Edge: You hunt for Expansion AI rather than just buying the obvious names.
Blind spot: Position sizing. Expansion AI should be sized for high volatility and a real chance of going to zero.
Where to start: Rob's premium newsletter, plus an AI assistant to read filings with you.
Level 2, Informed. You follow AI investing, own several names and know the stack has layers, but you mostly rely on other people's analysis.
Expansion AI Investor. AI-native companies creating entirely new categories. Built on the book's Expansion AI: new business lines AI makes possible, which behave like lottery tickets the market often misprices.
Mental models to focus on
#5 AI companies scale faster, but revenue quality beats revenue quantity.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
Profile 3.3 · Level 3 Analytical · Expansion AI Investor
The Early-Stage Public Hunter
You look for small and mid-cap AI pure-plays before they're widely covered, and can tell production revenue from pilot revenue.
Edge: You're playing where coverage is thin and mispricing is most likely.
Blind spot: Illiquidity and binary outcomes. One bad position can hurt out of proportion to its size.
Where to start: Rob's premium tier, cited research tools, and a liquidity check before every buy.
Level 3, Analytical. You judge companies on fundamentals and unit economics, use primary sources, and hold a thesis for each position.
Expansion AI Investor. AI-native companies creating entirely new categories. Built on the book's Expansion AI: new business lines AI makes possible, which behave like lottery tickets the market often misprices.
Mental models to focus on
#1 AI is a collection of technologies: defensibility matters more than paradigm.
#5 AI companies scale faster, but revenue quality beats revenue quantity.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
Profile 3.4 · Level 4 Specialist · Expansion AI Investor
The Private + Public Hybrid
You invest in public AI pure-plays and in private AI startups as an angel or LP.
Edge: Your private-market view informs your public-market calls, and the reverse.
Blind spot: Private valuations aren't public comps. Carrying private-market enthusiasm into public stocks can be expensive.
Where to start: The AI in NYC dinner series (by invitation) and a briefing with Rob and Vik.
Level 4, Specialist. You've gone deep on particular layers or sectors, read transcripts every quarter, and follow a written, tracked process.
Expansion AI Investor. AI-native companies creating entirely new categories. Built on the book's Expansion AI: new business lines AI makes possible, which behave like lottery tickets the market often misprices.
Mental models to focus on
All six.
Profile 3.5 · Level 5 Insider · Expansion AI Investor
The AI Operator-Investor
You're an AI founder, operator or active angel who can read a technical paper and see which companies it favors.
Edge: Technical fluency, a deal network and pattern recognition across many deals.
Blind spot: Confirmation bias. You've bet your career on AI, so every signal looks bullish. You need people who argue the other side.
Where to start: The AI in NYC dinner series (by invitation): peers who will argue the other side.
Level 5, Insider. You work in AI or invest in it privately, and see technical and commercial shifts before they're public.
Expansion AI Investor. AI-native companies creating entirely new categories. Built on the book's Expansion AI: new business lines AI makes possible, which behave like lottery tickets the market often misprices.
Mental models to focus on
All six.
Profile 4.1 · Level 1 Curious · Thematic Rotator
The AI News Follower
You trade on AI headlines and themes you read about.
Edge: You pay attention in a market that changes fast.
Blind spot: You're often buying the top. By the time a theme reaches the headlines, the easy money is gone.
Where to start: Rob's newsletter to get ahead of the news cycle, and a pause on trading the news.
Level 1, Curious. You know AI matters and may own an obvious name or two, but you're still learning the vocabulary.
Thematic Rotator. Rotate between AI sub-sectors as capital and attention move. Leans on mental model #4: as AI makes some work cheap, the choke points move, and you try to move with them.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
Profile 4.2 · Level 2 Informed · Thematic Rotator
The Sub-Sector Allocator
You move your AI exposure between infrastructure, applications, agents and verticals depending on where you see the next wave.
Edge: You recognize that AI has sub-themes with different cycles.
Blind spot: Rotation costs taxes and trading costs. Be wrong twice in a row and the drag is real.
Where to start: Rob's premium newsletter plus a research tool for watching sub-sector trends.
Level 2, Informed. You follow AI investing, own several names and know the stack has layers, but you mostly rely on other people's analysis.
Thematic Rotator. Rotate between AI sub-sectors as capital and attention move. Leans on mental model #4: as AI makes some work cheap, the choke points move, and you try to move with them.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
#4 AI changes markets and strategy: moats move to new choke points.
You combine macro signals (rates, capex cycles, chip pricing) with sub-sector analysis and rotate quarterly based on data.
Edge: Systematic rotation beats chasing.
Blind spot: Macro data lags. By the time it confirms a rotation, it's often late.
Where to start: Rob's framework plus charting and macro tools.
Level 3, Analytical. You judge companies on fundamentals and unit economics, use primary sources, and hold a thesis for each position.
Thematic Rotator. Rotate between AI sub-sectors as capital and attention move. Leans on mental model #4: as AI makes some work cheap, the choke points move, and you try to move with them.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
#4 AI changes markets and strategy: moats move to new choke points.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
You write a formal thesis for each rotation, track it, and know your hit rate.
Edge: Rigor turns rotation into a process rather than instinct.
Blind spot: Rotation struggles in trendless or whipsaw markets.
Where to start: The AI in NYC dinner series (by invitation), and a briefing with Rob and Vik as a sounding board.
Level 4, Specialist. You've gone deep on particular layers or sectors, read transcripts every quarter, and follow a written, tracked process.
Thematic Rotator. Rotate between AI sub-sectors as capital and attention move. Leans on mental model #4: as AI makes some work cheap, the choke points move, and you try to move with them.
Mental models to focus on
All six.
Profile 4.5 · Level 5 Insider · Thematic Rotator
The Market-Moving Rotator
You see inside several AI sub-sectors, and your rotation calls can influence smaller investors.
Edge: You see technical and capital shifts before the market does.
Blind spot: Your public positions affect the market you're trying to call. Watch for reflexivity.
Where to start: The AI in NYC dinner series (by invitation) and a briefing with Rob and Vik.
Level 5, Insider. You work in AI or invest in it privately, and see technical and commercial shifts before they're public.
Thematic Rotator. Rotate between AI sub-sectors as capital and attention move. Leans on mental model #4: as AI makes some work cheap, the choke points move, and you try to move with them.
Mental models to focus on
All six.
Profile 5.1 · Level 1 Curious · Tactical Trader
The AI Momentum Chaser
You buy AI stocks after they've moved on news, hoping the move continues.
Edge: You're willing to act in a volatile market.
Blind spot: Late entries and loose risk control are very likely costing you money.
Where to start: Pause tactical trading. Build a Core AI or Infrastructure base first.
Level 1, Curious. You know AI matters and may own an obvious name or two, but you're still learning the vocabulary.
Tactical Trader. Catalyst-driven and dislocation-focused, often with options. Leans on mental model #3: a single result can reprice a whole layer, and you try to trade those moments.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
Profile 5.2 · Level 2 Informed · Tactical Trader
The Catalyst Player
You trade around AI earnings, product launches and big announcements.
Edge: Catalyst trading can work when it's done with discipline.
Blind spot: Expected moves in AI names are huge, and option prices already reflect most of the upside.
Where to start: Strict position-sizing rules before any signal service.
Level 2, Informed. You follow AI investing, own several names and know the stack has layers, but you mostly rely on other people's analysis.
Tactical Trader. Catalyst-driven and dislocation-focused, often with options. Leans on mental model #3: a single result can reprice a whole layer, and you try to trade those moments.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
#5 AI companies scale faster, but revenue quality beats revenue quantity.
You look for genuine mispricings, like the events that reprice a whole layer overnight.
Edge: You can act when others freeze.
Blind spot: True dislocations are rare and most "opportunities" are noise. This takes patience, not activity.
Where to start: Rob's newsletter for framing dislocations, plus an execution tool.
Level 3, Analytical. You judge companies on fundamentals and unit economics, use primary sources, and hold a thesis for each position.
Tactical Trader. Catalyst-driven and dislocation-focused, often with options. Leans on mental model #3: a single result can reprice a whole layer, and you try to trade those moments.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
#4 AI changes markets and strategy: moats move to new choke points.
You use options around AI positions: covered calls, protective puts, defined-risk spreads around catalysts.
Edge: Well-sized options turn conviction into asymmetric payoffs.
Blind spot: Implied volatility on AI names stays high, so you pay up for leverage.
Where to start: Strategy modeling tools plus Rob's catalyst framing.
Level 4, Specialist. You've gone deep on particular layers or sectors, read transcripts every quarter, and follow a written, tracked process.
Tactical Trader. Catalyst-driven and dislocation-focused, often with options. Leans on mental model #3: a single result can reprice a whole layer, and you try to trade those moments.
Mental models to focus on
#3 Expect major dislocations: one result can reprice a whole layer overnight.
#5 AI companies scale faster, but revenue quality beats revenue quantity.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
Profile 5.5 · Level 5 Insider · Tactical Trader
The Professional Trader
You trade AI professionally or close to it, with serious tooling.
Edge: Infrastructure, domain expertise and capital together are a real edge.
Blind spot: You're competing with hedge funds in this game, and edges erode fast.
Where to start: Your existing stack, with Rob as a macro and sector sounding board.
Level 5, Insider. You work in AI or invest in it privately, and see technical and commercial shifts before they're public.
Tactical Trader. Catalyst-driven and dislocation-focused, often with options. Leans on mental model #3: a single result can reprice a whole layer, and you try to trade those moments.
Mental models to focus on
All six.
Profile 6.1 · Level 1 Curious · Basket Investor
The AI ETF Buyer
You bought an AI ETF because you want AI exposure without picking stocks.
Edge: You chose the lowest-risk route to AI exposure.
Blind spot: AI ETFs differ a lot in holdings, concentration and fees. Not all AI baskets are the same.
Where to start: Rob's newsletter, plus a look at what your ETF actually holds.
Level 1, Curious. You know AI matters and may own an obvious name or two, but you're still learning the vocabulary.
Basket Investor. Diversified AI exposure through ETFs, indexes and rules. Closest to the book's ways to invest around AI without picking individual winners.
Mental models to focus on
#1 AI is a collection of technologies: defensibility matters more than paradigm.
Profile 6.2 · Level 2 Informed · Basket Investor
The Thoughtful ETF Allocator
You blend 2–3 AI ETFs (semis, applications, robotics) to get the exposure you want.
Edge: You've thought about diversifying across the stack.
Blind spot: Overlap between ETFs often makes you more concentrated than you think.
Where to start: An overlap check, plus Rob's framework to test your mix.
Level 2, Informed. You follow AI investing, own several names and know the stack has layers, but you mostly rely on other people's analysis.
Basket Investor. Diversified AI exposure through ETFs, indexes and rules. Closest to the book's ways to invest around AI without picking individual winners.
Mental models to focus on
#1 AI is a collection of technologies: defensibility matters more than paradigm.
#4 AI changes markets and strategy: moats move to new choke points.
You built your own basket of 15–30 AI names, equal-weighted or rules-based, rebalanced periodically.
Edge: A custom basket avoids ETF concentration and fees.
Blind spot: Equal weighting ignores quality, and rules-based rebalancing can keep adding to deteriorating positions.
Where to start: Automation for rebalancing, plus Rob's framework for quality screens.
Level 3, Analytical. You judge companies on fundamentals and unit economics, use primary sources, and hold a thesis for each position.
Basket Investor. Diversified AI exposure through ETFs, indexes and rules. Closest to the book's ways to invest around AI without picking individual winners.
Mental models to focus on
#4 AI changes markets and strategy: moats move to new choke points.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
You run a factor-tilted AI portfolio (quality, growth and momentum within AI).
Edge: A systematic approach removes most emotional decisions.
Blind spot: AI factors behave differently from traditional ones, and backtests on short histories mislead.
Where to start: Factor scoring and automation tools, with Rob's thesis layer for context.
Level 4, Specialist. You've gone deep on particular layers or sectors, read transcripts every quarter, and follow a written, tracked process.
Basket Investor. Diversified AI exposure through ETFs, indexes and rules. Closest to the book's ways to invest around AI without picking individual winners.
Mental models to focus on
#2 AI challenges SaaS assumptions: pricing and unit economics are being rewritten.
#5 AI companies scale faster, but revenue quality beats revenue quantity.
#6 Be careful evaluating AI COGS: margins can improve or deteriorate.
Profile 6.5 · Level 5 Insider · Basket Investor
The AI Portfolio Architect
You build AI portfolios across public, private and alternative assets and think in portfolio construction, not picks.
Edge: Portfolio-level thinking plus domain expertise is a professional-grade edge.
Blind spot: Sophistication can hide concentration if the underlying bets are correlated.
Where to start: The AI in NYC dinner series (by invitation) and custom research from Rob and Vik.
Level 5, Insider. You work in AI or invest in it privately, and see technical and commercial shifts before they're public.
Basket Investor. Diversified AI exposure through ETFs, indexes and rules. Closest to the book's ways to invest around AI without picking individual winners.
Mental models to focus on
All six.
On top: your behavioral type
The third dimension doesn’t change your profile; it changes your guardrails. It uses Michael Pompian’s four behavioral investor types: do you tend to act or wait, and are your mistakes driven more by feelings or by reasoning? A Preserver tends to hold losing positions and an Accumulator to concentrate and trade too much, so the same profile needs different rules for each.
PassiveActiveEmotional
Preserver
Puts safety first and feels losses sharply. Tends to hold losing positions, avoid change and stick with the familiar.
Accumulator
Confident and comfortable with risk, often having built wealth by taking it. Tends to overconfidence, concentration and trading too much.
Cognitive
Follower
Takes cues from advisers, friends and popular opinion more than from a plan of their own. Tends to chase what has recently worked.
Independent
Does their own research and trusts their own analysis. Tends toward confirmation bias: looking for evidence that agrees with them.
Questions about the assessment
What is the AI Investor Assessment?
An 18-question quiz that places you on one of five levels of AI investing maturity, one of four behavioral investor types and one of six approaches to investing in AI, then combines them into one of 30 profiles with the mental models, guardrails and tools that fit you.
How long does it take?
About five minutes. There are 18 multiple-choice questions in three parts, and your result appears immediately on the page.
Do I need to give my email or any personal information?
No. The quiz runs entirely in your browser; your answers are not sent to us or stored, and there is no sign-up.
Is this investment advice?
No. It is educational. It doesn’t ask about your finances or goals, doesn’t recommend any security and doesn’t tell you how much to invest. Talk to a licensed adviser about decisions specific to you.
What are the four behavioral investor types?
Preserver, Follower, Independent and Accumulator, from Michael Pompian’s research on behavioral finance. They come from two questions: do you tend to act or to wait, and are your mistakes more often driven by emotion or by reasoning.
What are the six ways to invest in AI?
Infrastructure (the chips, power and cloud capacity AI needs), Core AI (established companies AI makes stronger), Expansion AI (new categories AI creates), Thematic rotation between AI sub-sectors, Tactical trading around catalysts, and Basket investing through ETFs or rules.
Why does the result recommend tools, and are they paid?
Different levels and approaches need different research tools. Every result starts with free ones, prices are shown only where the vendor publishes them, and paid tools are optional. Rob May’s book, newsletter and the free research on this site appear in results, which we disclose on the page.
How is this connected to Rob May’s book?
The profiles, the approaches and the mental models you are pointed to all come from Investing in AI: Six Mental Models to Tell Moats from Traps. The quiz is a way to find which parts of the book matter most for you.