Poor. Hungry. Driven.

In hiring and investing, we are all biased. My bias? I bias toward and pattern match on PHDs: Poor. Hungry. Driven.  I look for people who’ve taken it on the chin in life and come back determined to win. I look for hustlers who’ve risen beyond their...

Anatomy of a (Good) Investor Update

Now that I’m an investor, I am on the receiving end of a lot of investor update emails from startups. Some are clear, consistent and excellent. Some are confusing, some are sporadic, many are bad. As an investor, the quality of a startup’s communications...

The Challenge of Rolling Solo

Being a solo founder is hard. It’s almost trite to say, but I’m in it and it’s real. I’m not sure if it’s just the fact that I’m a solo founder or the solo person employee. Even though I’ve started 3 companies before and had...

Thanksgiving Letter to My Portfolio CEOs

From: Matt Mireles Date: Fri, Nov 23rd, 2018 at 9:56 AM Subject: Thankful To: Founders   Hi Folks, On this Thanksgiving holiday, I am thankful for… you. You are my tribe. A lot of you are the people I talk to most and have become some of my closest friends....

Moral Courage: Not Taught at Harvard

An irony of facebook’s situation. Sheryl got her MBA at Harvard. One of the most famous cases (Extra Strength Tylenol) in one of the most famous classes (Business History) she took: in 1982, someone put cyanide in Extra Strength Tylenol capsules and killed 7...

How to Size a Market in 5 Minutes or Less

My basic approach to market sizing is this: # of potential customers x average selling price = Total Addressable Market Don’t know average selling price (aka ASP)? No problem. Then use economic value creation instead as an upper threshold for price. Economic value...

Rape & Justice in America

In college, I was in a serious, loving relationship with a woman who had been drugged, bound and violently raped by a man with the help of his two roommates. The date rape operation they devised was so evil and so calculated that I knew this could not have been the...

14 Lessons Learned from Year #1 as a Startup Investor

Lessons I’ve learned investing so far: 1) FOMO is real. You have to make a conscious effort to not let it affect your thinking and maintain your own intellectual independence. 2) Investing downstream of YC at Demo day is both awesome and terrible. Awesome because the...

Looking Back: Startup Investing Year #1

I wrote my first check to a startup on April 11, 2017. Since then, I’ve invested in 16 startups via my personal money and a small fund I manage backed by Social Capital. I’m having blast! TLDR: I bet on outsiders using capitalism to solve society’s...