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Vice clauses prohibit many institutional investors from supporting companies in industries like gambling, alcohol, and cannabis. So, founders in these verticals often look to angel investors when they’re raising. Let's face it: vice companies can bring in a ton of revenue. After all, people can’t live without [insert vice of your vice of choice], right? So I wanted to know: what’s it like for the founders who are building these businesses? And what signals should early-stage investors look for when deciding whether or not to invest in a vice company? To answer this question, I interviewed David Hua, co-founder of Meadow.

Lifetime value measures the total revenue you make from each customer over the lifetime of the relationship.

As an early-stage investor, the lead investor's term sheet will impact you and your shares. This article covers the three most important things you should know about how a lead investor can affect you and what you can do about it.

SPVs are formed to bring multiple investors together to form a company. How does it work, and why invest through an SPV instead of directly?

Imagine getting pitched by a company that, on paper, is doing great. Solid growth, proven founder, and the company has found product/market fit. But you had to invest on an uncapped note. We break down what this is and why every early-stage investor should know about this.

Annual recurring revenue is a metric used for SaaS companies to normalize revenue on an annual basis. It's a key growth metric as an angel investor if you ask a few key questions to understand how a company is making money (and creating their forecast).

Cost of goods sold is how much it costs to make a product or service.

A founder pitches you an interesting idea but gets rejected at first impression. But what if you wanted to dig deeper to see if this would actually work? Here are the questions we recommend asking to determine if this is worth pursuing.

When you invest in early-stage companies, the cycle from investment to exit will take years. So how do you know what your weaknesses are, and if you're improving as an investor? Here are two ways to get valuable feedback.

How do you evaluate an early-stage company when you don't have a personal relationship with the founder? When all you have is a deck and a deal memo? Two words: Market pull.

Imagine you are approached by an early stage startup founder who wants to raise money. She has no revenue or metrics. How do you evaluate the company without any KPIs? Start with these two questions.

Josh Buckley's billion-dollar portfolio proves gaming founders make exceptional enterprise investors. The former Mino Games CEO turned his mobile gaming experience into one of the most impressive angel track records, with early investments in Figma, Rippling, Retool, and Clearbit (acquired by HubSpot for $150M).Buckley's secret? Gaming companies figured out user engagement, viral mechanics, and freemium models years before enterprise software embraced "product-led growth." His investments consistently target B2B companies that apply gaming principles: instant value delivery, social features, and engagement loops that make work feel less like work.With 4 unicorns from concentrated $300K bets and board seats at key companies, Buckley's approach beats typical spray-and-pray investing. His "cockroach entrepreneur" theory targets founders who understand unit economics and iterative optimization - skills gaming teaches better than any MBA.The tactical lesson? Invest in enterprise software that feels consumer-grade, where users actually want to engage beyond their job requirements.

Whitney Wolfe Herd built Bumble from zero to a $13B IPO. Now she's investing in the next generation of consumer companies. Her portfolio reveals a clear thesis: back mission-driven founders in underserved markets who can change behavior at scale. Here's what early-stage investors can learn from her approach.