The last 6 of 37 angel investments the last 3 years.

If you’ve been following, I’ve been making some angel investments and a chat with a friend yesterday got me thinking about the bundle.

The investments

There are 37 over 3 years, all relatively small dollar amounts.

These are the six in 2015:

Porchlight – stealth, I think.
Penrose Hill – stealth, possibly.
Verifly – Verisign for drones
Concord – Faster algos through stream processing
BringMeThat – Restaurant food delivery for smaller cities and regions
HireNurture – Builds talent communities for employers to hire better, faster, cheaper. lists them all

What they are like

These are all awesome companies with either a) high-profile founders who clearly know what they are doing + A-list investor group or b) strong traction/engineering under-the-radar deals. 50-50. Not that one is to the exclusion of the other but that’s where the two types are centered.

Looking back over the longer list it is very heterogeneous.


I calculated the cash-on-cash using “mark to market” on the 37 deals listed here at and found something surprising. On paper the group is worth 2x the amount invested. Some of these are 2.5 years old — so that’s a good rate of return if I could get the cash out. Some of these are less than 1 year old.

I had the chance to sell a few bits here and there, and that has returned some cash which is quite spectacular. So I have received back about 50% of the cash laid out which is cool, but then I re-invested that already, so I have 100% of the cash “at work”.

The funny calculation in all this is simply that these are almost all A round financings. And as a startup founder and builder myself that has been through tons of this, I know an A round ain’t shit. But the A rounds are typically 3-4x markups of the seed investment – so the companies that have gotten past my investment to the A round are typically marked way up.

They probably 2-3x again in a B round but the companies where I got involved in 2013 are only just now getting to that stage.

So in short I haven’t returned any cash back out of the angel vehicle.

Also, only 1 deadpool.

Vanity metrics

I’m pretty amazed to see the VC names these companies have attracted funding from *after* me — Founders Fund, Google, Andreessen, Lux Capital, Formation8, Battery, Kleiner, Lakestar, Khosla. I guess no USV, Bessemer, Accel or Sequoia yet so still something to look forward to on that.