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Lessons from 6 Weeks of Angel Investing

Posted on Oct 11, 2014 by in Startup Funding | 1 comment

Lessons from 6 weeks of Angel Investing.  Interesting question from Mr. Cummings.  I was up the other night straight hating on my own blog and this question popped through.  It is a good question, but I’m still trying to rethink my blog and would appreciate any thoughts on that.  It’s not just the writing – I enjoy that, it is getting bored with it, which interesting enough relates directly to today’s question.  What have I learned in the last six weeks of angel investing?

Angel Investing

Six weeks ago covers all of September, so I reviewed my calendar, Evernote, and checkbook:

Lesson One: Being more Technical Makes me Better

I just finished the Ruby classes on Code Academy and I can tell you without question it has made me a better investor.  My thought processes are now more product centric – balancing my natural sales and marketing instincts.  I had a tendency to think I can sell anything which is actually useless for investing.  At least three times in the last six weeks I’ve thrown bullshit flags at entrepreneurs related to their solutions (meaning it straight up didn’t work) but I’ve also helped (I think) several make their products better.

Lesson Two:  Opportunity Lies in Dark Scary Corners

On a regular basis Paul Judge and Adam Ghetti scare the living Sh*t out of me.  There are days I truly think “ignorance is bliss”.  Being around Ionic Security and Pindrop Security has been a tremendous learning experience.  Atlanta is clearly an InfoSec hub, and now I know (just) enough to understand the opportunity.  The Internet is not safe, far from it – and there are tons of opportunities in making scary places safer.  (side note: I have openly admitted passing on Social Fortress, well another opportunity presented itself and I jumped at it – I’ve always believed in Adam, I just didn’t understand it, now I actually do understand it and Adam would have been proud watching me explain it last night).

Lesson Three:  Unicorns need Trillions

TechSquare Labs has it’s first home grown deal ready (I can hear Urvaksh calling Paul).  The process of watching that idea come together has shown me that if you have any chance of creating a Unicorn (baseball speak for Big Ass Company) you need to being looking at problems that currently have billions if not trillions spent on them.  I will blog about this new business once it is fully ready to present, but the lesson is that the idea surrounds a space that already has nearly a trillion dollars worth of transactions in its current state.

Lesson Four: Technical Founders Rule the World

This was one of the hypothesizes I had over a year ago, that technology wasn’t getting commoditized like everyone thinks.  Meaning just because I can code a little now and spin up something on AWS (Amazon Web Services) or say MVP 10 times that doesn’t mean things are less technical or easier.  I truly believe that the world is getting more technical and the big problems need engineering minds to solve them.

Quick summary, the last six weeks has taught me a lot, and included three stock certificates: one in mobile applications, one in information security, and one in banking.  The group includes a Ph.D student, a current undergraduate student, and one no college.  All lead by technical founders.

1 Comment

  1. I’ve been thinking about your last point and I agree wholeheartedly. If you really want to solve BIG problems and go after big markets, you have to be a tech founder and know how to code pretty well. The advantage of being agile and knowing your product inside out is enormous.

    I used to think you could outsource but you can’t, at least not at the outset.

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