Why do you angel invest / what got you into it?
I’ve been in the startup community since 1996 and I’ve been very lucky to have had a great experience as an entrepreneur, both in business – and consumer-facing startups. I love nothing more than helping entrepreneurs get companies going. I first looked at angel investing as a way to give back in a way that scaled beyond just my personal time. Actually, I initially resisted angel investing because I didn’t think I could do a good job of it but then I realized that it was something I had to try.
What was your first angel investment?
Shelby. They aggregate video discovery across multiple social streams.
How did it turn out?
So far so good. One follow on round.
What investment do you most want to brag about?
Shelby, because it really fits the way I like to invest. I got to know the team when they were on a completely different business called Homefield. I wasn’t completely sold on that business – which was fine because I wasn’t angel investing at the time anyway. When I later decided to dedicate some funds to angel investing, I met Reece (Pacheco, the founder) again at TechStars, he explained to me where they were shifting the business and I said to myself, “I love that idea, I love that team, I love how hard they work. That’s something I want to commit to.”
Any notable or amusing train wrecks?
Guyhaus. They started as a subscription men’s basic business. You would get shampoo, toothpaste, deodorant, etc. shipped to your door – automatic replenishment for guys who hate to go to the grocery store or shop. There were a number of unanticipated problems. Number one was the pacing of those items varied a lot by product so figuring out the shipment timing was hard. The entrepreneur pivoted to a digital publishing business, a complete 180 from what Guyhaus was. It was frustrating to me because I thought there was a real business in the first concept. I am not sure he could have figured it out but, as I’ve told him, I would have liked him to have stuck it out a bit longer.
Most humbling experience (relating to angel investing)?
I very much wanted to make an investment in a company in the fashion space. I met with the entrepreneur and I was very helpful, solved a major problem for them, only to be turned down by the founder because I wasn’t a big name investor. The same thing happened with Sidetour, a marketplace for personalized experiences. I got to know the entrepreneur, helped out a bit. I thought it was a great idea…but so did everybody else so I wasn’t able to do the investment.
What’s the smartest thing someone pitching you ever said or did?
This is a very personal thing but one entrepreneur said “I am going to continue to use you, even if you decide not to invest. I want help from you.” He read the way I approach these things very well.
Editor’s Note: Charles invested
What’s the dumbest thing?
One guy said, “I started a company because I wanted to be an entrepreneur so a friend and I put seven ideas on a whiteboard and figured out which was the best one.” The idea he picked was actually interesting but I am much more comfortable with people whose desire is not to be an entrepreneur but to change the world. They might not be able to change the whole world but at least change their world. I want someone with tremendous domain expertise who sees a major hole in the market that he’s going for come hell or high water.
What makes you better than the average angel?
I don’t yet have a track record of exits to point to (yet) but I come from the perspective of someone that has been operating startups for a long time. I am willing to do anything the entrepreneur asks me to do that is within my power. I’ll run a sales meeting, I will help with pitch decks, whatever. Not everyone takes me up on this – and that’s fine – but I like to be active, to be put to work.
Pretend that it’s 2018 and complete this sentence, “[Technology X] is less than 5 years old and now I can’t imagine life without it.”
Wearable personal health monitors.
What’s the best way for entrepreneurs to reach out to you?
See my blog post about my investment criteria: My Thoughts on Angel Investing
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