The Investor's Playbook: How to Evaluate Startups

Evaluate a startup the way the person writing the check actually does.

By: Roman Jonas

About the course

A practical, no-nonsense framework for evaluating early-stage startups before writing a check. Built from real investment patterns, not theory, covering how to think about returns and deal flow, assess founders and teams, read market signals and traction honestly, understand valuation and deal terms, and build a disciplined portfolio. For angels, syndicate members, and operators who want to invest with the rigor of professionals who actually do this for a living.

Course content

5 sections · 18 lessons · 1 free

1.How Investors Actually Think About Returns4 lessons

1.1 The Power Law and Why Most Deals Don't Matter

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1.2 What Stage You're Investing At and Why It Changes Everything

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1.3 Building a Return Thesis Before You Look at Deals

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1.4 The Deal Funnel: How Many Pitches Become Investments

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2.Evaluating the Team3 lessons

2.1 Founder-Market Fit: The Question Behind the Question

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2.2 Cofounder Dynamics, Team Completeness, and Whether They Can Build a Real Team

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2.3 Reference Calls: What to Ask and What to Listen For

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3.Market, Product, and Traction4 lessons

3.1 Market Size: Reading the Opportunity Without Getting Fooled by TAM

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3.2 Product Evaluation: What to Assess When You're Not Technical

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3.3 Traction Signals: The Metrics That Actually Tell You Something

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3.4 Competitive Analysis: Seeing the Market the Way the Founder Should

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4.Reading the Deal: Valuation, Terms, and Cap Table3 lessons

4.1 Valuation at Seed: What's Reasonable and What's Overpriced

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4.2 SAFEs, Convertible Notes, and Priced Rounds: What You're Actually Signing

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4.3 Cap Table Red Flags and Dilution Math

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5.Risk, Due Diligence, and Deciding Yes or No4 lessons

5.1 Structuring Your Due Diligence: What to Check and How Deep to Go

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5.2 Risk Categories: What Can Kill a Startup and How to Weight Each One

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5.3 Portfolio Construction: Sizing Checks and Building Toward the Power Law

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5.4 The Decision: How to Write a Clean Yes or No and Why Most Investors Get This Wrong

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Free preview lessons

1.How Investors Actually Think About Returns1 lesson

The Power Law and Why Most Deals Don't Matter

Most investors learn this the hard way: a diversified portfolio of mediocre bets doesn't save you. One fund-returner does. That's the power law, and it shapes every single decision a serious early-stage investor makes.

In a typical 20-company angel portfolio, roughly 15 companies will return nothing or pennies. Three will return 1x to 3x. One or two will drive 80% or more of your total returns. This isn't pessimism. It's the observed distribution across decades of venture data from Cambridge Associates, Kauffman Foundation, and individual fund track records alike.

What this means practically: your job isn't to avoid bad investments. You can't. Your job is to make sure you're actually in the deals with a realistic path to 20x or 50x, and that you're not so conservative on entry that you price yourself out of the upside.

The math you need to hold in your head

Write ten $10,000 checks ($100k deployed). Nine go to zero. You need the tenth to return at least $100k just to break even. To make angel investing worthwhile as an asset class, that tenth probably needs to return $300k to $500k minimum, which means you need companies that can genuinely reach $50M to $200M or more in exit value.

That filter alone kills most pitches before you open a deck. If a founder can't articulate a credible path to a $100M-plus outcome, the math doesn't work for you as an investor, regardless of how good the team is. Hold this framework throughout the course. Every evaluation question connects back here.

Reviews

★★★★★5.0 · 1 reviews

Lucie Černá★★★★★6/2/2026

Tohle mi otevřelo oči. Přesně tohle chybělo – mentální posun od "dělám všechno sám" k "buduju systém". Nejlepší kurz, co jsem za poslední rok absolvovala.