Why do you angel invest / what got you into it?
I come from an entrepreneurial background. I’ve started several companies. I also joined small innovative companies. The last one when I left had gotten to be 300 people. As the companies get bigger, you start to lose some of the interesting ideas and that’s what gets me up in the morning. When I hear ideas and I wonder “How did they think of this?”- that makes my day. When I was getting started, people threw money at me and said, “here’s some money to enable you to get started.” Now I am in a good place in that some of my previous investments generated some return that I can reinvest now. So I think of angel investing both as making a good investment and as returning to the community as well.
What are some of the more recent investment you have made?
The first is Appy Couple, a wedding app for planning, logistics, guest communication, and a repository of images, notes, memories, etc. It was a great combination of an “A+ founders” and “A+ idea”. Great, passionate team with a great idea. And it’s not just what the app is today but what it can grow into.
The other is TripleLift. Their starting point was Pinterest, a very popular platform where people share their ideas, likes, and possibly purchase intents. However, a lot of this information was not being collected or used in a way that would enable companies and brands to act on it, so the amount of value brands get out of these platforms is not at the same magnitude as the interest these platforms get. Now TripleLift is evolving into an ad feedback tool connecting online advertising with users interests and intentions. TripleLift is a “Hail Mary pass” at solving this problem for me, but it could be a touchdown.
Was there a startup that you backed that you feel should have hit but didn’t?
I didn’t put money directly in this company but I was invested in it through Entrepreneurs Roundtable Accelerator and I was really surprised that they didn’t go farther. The company was called Glossy and their idea was to collect all your social network presence – your tweets, your Facebook updates, et. al. – into one site: your own repository, with a really beautiful interface. The analytics value of this would have been huge and they would have had my money. But before I could invest they folded, “pivoted” I should say, and are now in a completely different space.
What was the most surprising lesson you have learned since you started angel investing?
I have a finance education from UPenn and a PhD in Engineering from UMass Amherst. I ran an investment fund for a few years. So I think that I know technology and I understand finance. I ought to be able to pick winning companies consistently and, when you think about it, it is pretty humbling that I can’t. It’s difficult to admit, but you are never smart enough to guess what a company will or won’t do. Nobody anticipated how fast a company like Facebook could grow, nor how fast other companies would fold. I had to learn the ropes like anyone else.
So you can’t just invest in one or two companies and think that you are going to get a predictable return. You have to invest in a portfolio. Now while I do invest in individual companies, I am also involved in the ERA. I’ve invested in all their classes. In fact, I was ERA’s very first investor, before they were even formed or had any investment. I really do believe that you need to spread your risk over a lot of companies and if you are a relatively small angel investor, investing in accelerators is a great way to do that.
Any specific advice for entrepreneurs?
Something that good entrepreneurs do consistently that is smart, is that they continue to update you on their progress, even if you passed. There are companies that I did not invest in, but I get updates on them and now I think that I may invest. They don’t look at an investor as a transaction. The more an entrepreneur gives you the sense that they view this as a relationship, the more likely that I would be to invest in them in the future.
Also – and it amazes that some many people cannot do this – every entrepreneur should have a 30 second pitch, a 2 minute pitch, and a 10 minute pitch just nailed down that they can recite in their sleep. It’s inexcusable if someone cannot get your attention and explain their idea in 30 seconds.
Finally, on the execution side, entrepreneurs should know the difference between perseverance and chasing a bad idea. You should check your assumptions constantly and should not hang on to an idea and waste your time if it is not happening.
Anything entrepreneurs should not do?
I’ll tell you two or three things that, every time I hear them, I just shut my mind. When people say, “We don’t have competition” and “It’s never been done before.” That’s just crazy.
Another thing I hear which is actually pretty intellectually insulting is when people say, “This is a $10B market and if I get half a percent, this is a $50M business.” The fact that it is a huge market doesn’t mean you will be able to squeeze 0.5% out of it. Size does not guarantee success. It’s just not true.
What makes you stand out as an angel?
My edge is in two things. One is that I have equally strong backgrounds in tech and finance, so when I look at opportunities, it’s not just a gut feeling. I come across a lot of successful entrepreneurs and they invest willy-nilly in companies just because they like the people or it is an idea they never thought of. That’s great but it’s not going to generate returns.
Also, it helps that I am an entrepreneur. Currently, I am working on three companies. One is a partnership but the other two I am basically bootstrapping myself. So being an investor plus a current entrepreneur in the trenches is a real difference.
Pretend that it’s 2019 and complete this sentence, “[Technology X] is less than 5 years old and now I can’t imagine life without it.”
Let’s take phones. Haptic technology – tactile feedback – is just getting started. We think gorilla glass is great but imagine this: by electrical stimulation, you can make glass hard or soft. You can make the glass click. If you are dialing numbers, you can make that touchpad appear to your fingertips almost as raised buttons on your screen. You can even make the glass smooth or rough by electrical stimulation so you can find buttons easier. People are working on these types of materials technology right now. Or imagine this – and this is not that far-fetched: imagine your screen itself acting as your phone’s microphone by capturing the vibrations of the glass and that by making the glass vibrate, it can also be the speakers as well!
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