I have written about the parallels between surfing and investing in start-ups before (see Surf’s Up!… ironically, written just about a year ago to the day), but have found myself thinking about the similarities yet again recently and thought I’d share my thoughts on the matter with all of you once again.

Whether you are a VC or surfer in SoCal, see if this feels familiar to you:

You get up at the crack of dawn;

travel to where you are thinking (praying) the waves will be;

the water is so cold you can’t feel your feet or face;

you almost drown paddling out;

your arms/chest/back/shoulders ache from the effort;

you finally get to the lineup only to find the waters more and more crowded; and

you have periodic thoughts about getting eaten by a shark or catching a staph infection in our polluted waters…

and then you catch your first wave and all of the above just goes out your mental door and you’re in the moment enjoying the ride.  Life is short.  Enjoy the ride.

Well, it’s official.  The people have voted and they do, in fact, want their MDC…  The “MDC Crew” does it yet again and scores big time in this year’s Webby Awards (see below).  Congratulations to Rob, Warren, Paul, Matt, Troy, David, Harry and the rest of the new media rebel army.  You can read more about them here.  I am very proud to have invested in them and continue to expect GREAT things from them (stay tuned)…

Webby Award Winner: Best Comedy Series - Wainy Days

People’s Voice Winner: Best Comedy Series - You Suck at Photoshop

Webby Award Winner: Best How-To & DIY - You Suck at Photoshop

People’s Voice Winner: Best How-To & DIY - You Suck at Photoshop

3 Honorees:

Official Honoree / Humor: My Damn Channel

Official Honoree / Comedy: individual short or episode: Wainy Days - Season 1 - Episode #10 - The Future (guest starring: Rob Corddry, Zandy Hartig, A.D. Miles)

Official Honoree / Viral:
Harry Shearer’s “Found Objects” - Katie Couric #1

Harry Shearer’s “Waterboardin’, USA” was nominated for Best Music Video and we congratulate Freestyle 101 from G4TV.com on their win - as well as Minilogue from Blink Productions as the People’s Voice Winner for Music Video.

Keep up the good work guys!

They say ignorance is bliss and I’m beginning to appreciate the sentiment in new ways. The more I learn about a company and/or industry the more I realize just how little I know and how much more I want/need to learn. In case you didn’t know, I’m a VERY big fan of knowledge and one of my philosophies is that one can never know enough. Having said that, you might find it somewhat paradoxical that I’m a VC given what it is we VCs do for a living. Well, I have two thoughts I’d like to share with you. First, as much as I enjoy the quest for knowledge and the intellectual exercise of analyzing risk, I fundamentally believe that it is simply a means to an end and that one can suffer from “paralysis by analysis” if he or she loses sight of the overall objective of simply determining whether to make an investment (i.e., whether the potential reward justifies and outweighs the risk). Second, being a seed and early-stage investor is ALL about taking risk given the nascent natures of the companies we invest in. There is always a “leap of faith” on our part. We simply have to qualify and quantify such leaps and mitigate any risks (both those identified and those yet to have been identified) accordingly. As daunting as that sounds, it is absolutely invigorating and I LOVE my “job” such that I don’t consider it work at all.

Venture Capital was historically known as “Risk Capital” for the simple reason that its practitioners risked money on new ventures with the hopes of making many times over their money back for having taken such risk. Some have been arguing of late that the rewards just aren’t correlative to the risk they are taking with today’s start-ups.  Ask most seasoned VCs whether they would have invested in their biggest hits to date if they knew then what they know now and almost all of them respond with a resounding “no, too risky”. As fund sizes have grown larger, firm’s investment strategies have gravitated towards later-stage companies…seemingly leaving somewhat of a void at the earliest stages of investing and to those willing to take such risks. I, for one, am willing and up for the challenge.