Betting on the Ponies: non-Unicorn Investing

Twenty fucking five to one My gambling days are done I bet on a horse called the Bottle of Smoke And my horse won – The Pogues I have decided to angel invest. Any advice? I spent some time decades ago in the horse-racing world, as a guest of someone who was actually in the […]

The Signal and the Noise (Angel Investing 6)

[Note: Post Number 5, on modelling your portfolio, was supposed to be next. Then I asked my friend Chris Wiggins a naive question about power law distributions. In return he sent me this paper. And this software. And this syllabus. And this paper. And this video. And also this talk he gave, which was above […]

AIPP Data Modeling (Angel Investing, Sidebar 2)

More from the Angel Investor Performance Project data. Much of the financial activity at early stage companies happens around investment rounds. Acquisitions, failures, and fire-sales tend to happen when it’s time for the company to raise more money. So it doesn’t make sense to look at rates of failure or exits divorced from the fund-raising […]

AIPP Data Summary (Angel Investing, Sidebar 1)

The Kauffman Foundation has some data on angel investor investment and returns at their Angel Investor Performance Project. The data has some serious limitations, mainly that it is relatively concentrated in time (44% of the investments with data are ’99 or ’00), that there’s not enough investments to draw fine-grained conclusions, and that valuations at […]

Transcending Hobbyism (Angel Investing 4)

A company I really liked was out raising money. They went to a very well known early stage VC and had a great first meeting. A couple of days later the partner got back to them with a no. He said “We really like you and your company, but we have a portfolio construction problem.” […]

How to be Different When What you Sell is a Commodity (Angel Investing 3)

When I started a company my co-founders and I thought and discussed and argued about how we were different from our competitors, how there was a hole in the market, how we were going to win by going where no one had gone before. We got potential customers, suppliers, employees excited by talking about how […]

The Work-Work Balance (Angel Investing, 2)

The first question every prospective angel (and all my relatives) ask me is “What do you do all day?” It’s sort of a funny question. For any job more varied than working on an assembly line, the answer is either going to be pretty long or pretty vague. Usually I go with vague. Today I’m […]

Why I’m Not an Angel

If you bootstrap your business it’s your prerogative to make any stupid decisions you want–so long as you don’t run out of money. But if you decide you want your bootstrapped business to be as successful as possible, you probably make pretty much the same decisions a businessperson backed by outside capital does. The process […]