Shooting the Moon…From Startup Investing to Growth Investing

I learned the game of hearts the summer I travelled through Europe and Israel during the summer of ’89.

My friends Abe and Dan taught Rob and I the game and we were addicted. I was fascintaed by the ability to ‘shoot the moon‘, the ability to leave everyone else holding the bag. If I was off by just one point though, it was me holding the bag.

In my work and investing life, ‘shooting the moon’ is not my style. I am the opposite. I like to lay low, let everyone mix it up for the most part and if I am in a very strong position, take a few shots at ‘the moon’.

The strategy has served me well in both angel investing and growth investing.

I have run the same fund for 13 plus years and had the ability to gain my stride as an investor. Most of my limited partners have been with me since 1998 and would hopefully attest. I started Social Leverage in 2008 to invest in startups and am thinking hard about hybrid ways to bring both styles together in the years ahead.

Today, Fred Wilson has a post up about hitting your stride as an investor. I have followed Fred into some investments since he backed Wallstrip back in late 2006. The investments are Disqus, Get Glue and Covestor. Andrew Parker who worked for Fred at Union Square offered up Foursquare to me as a Company and team they had a lot of conviction in but was too early for them. I, lacking conviction about location (something I did not care about), passed. I was also offered up a Twitter investment at the same price as Fred back in 2007 or 2008 and I could not get my head around the price. Zynga rolled along to me as well, but again, my price rule kept me on the sidelines. I have learned more from passing on Foursquare, Twitter and Zynga than any winner I have had. These passes have helped further shape how I think about investing in early stage companies.

It took me at least 15 years to hit my stride as a stock investor and over 10 as an angel investor. I have no doubt, both can be cut in half in this amazing social and publishing era of the web.

Maybe because I have worked so much harder at stock investing that I feel it is an easier skill to learn as a trade than angel investing, but I am working on the data the last few months to truly back it up and will share it of course as I get it.

I do love the feeling of having enough hours/work in on both angel investing and stock investing to have conviction across the scope of a company life. My heart lies at the early stage (least liquid) and the latest of stages (high liquidity).


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  2. JimiH says:

    OK congrats on your history of success. You deserve praise. Now after taking in just a couple of the HL ‘get to know me’ posts I am compelled to ask one question/ comment; Sweet mother of pearl can you possibly talk about yourself any more than you already do? [Not likely]. Reading the mostly self indulgent ramblings – all for the good of the investing public – is tiresome.

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