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I remember going to a meeting with one of our limited partners where I explained our reasoning for staying clear of investments in biotechnology and novel compounds.  I equated it to the early rounds of the NCAA tournament – terming it “March Madness Investing.”  It turned out that my LP completely understood my analogy, shooting back, without missing a beat, that he felt the same way about selecting venture funds…

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My wife and I just submitted our NCAA brackets.  At tip-off it looks like there are 16 entries in my group, for a total pot of $320.  My wife’s got one bracket in, creating “pot odds” of 16:1.  This year I am playing two brackets, bringing my “pot odds” down to 8:1.  Of course, I have a system.

My first bracket is 100% gut-shot, a blast through the match-ups based mostly on personal feel.  I took this approach last year.  I picked a few upsets and entered the final four with a strong bracket.  My wife went to UConn, so I am a UConn fan, and I picked them to win it all last year despite my gut feeling for North Carolina.  This year UConn is out of the tournament, so my gut is pure.  I should have submitted two brackets last year.  I will not make that same mistake again.

My gut-shot spoiler is K-State.  I have them beating Syracuse and Kansas to get to the finals where they will lose to Kentucky.  It feels like Kentucky’s year to me, they have a great new coach who needs to win before he gets caught in another NCAA violation (like he did at Memphis and UMass).  Interestingly, out of the 32 first round games my gut produced 8 first round upsets (25%).  I bet that’s how many there will be, but I doubt they will be all or many of the ones I picked.  I think I am in big trouble on the gut-shot (for those interested my first round upsets are listed below).

As I was filling out my first bracket I found all sorts of interesting information on ESPN (dot.com, of course), where a horde of college hoops fans submit brackets every year.  With no real love interest in the tournament (UConn and USF are playing in the NIT), I decided to submit my second bracket based solely on ESPN’s “National Bracket,” which shows the preferences of the majority of the horde.  It turns out that the “National Bracket” is not much different than the NCAA tournament seeds.  Of the 63 potential games, the majority of the horde chose the favorite 59 times, with the only upsets coming in the first and second round (N Iowa (9) over UNLV (8), Louisville (9) over Cal (8), Texas A&M (5) over Purdue (4) and Michigan St. (5) over Maryland (4)) (Note a 9 over an 8 seed or a 5 over a 4 seed is hardly and upset, just perhaps an indication that the majority of the horde disagreed with the seeding ever so slightly).  But I know this is not the way things are going to turn out.  There has to be more upsets than that.  Perhaps I should submit a third bracket, the average of the first two.  That takes my “pot-odds” down to 4:1, I would lose alpha, returns would go down the tubes.

For the record, I claim no expertise in college basketball.  I read the box scores sometimes, and watch a game or two a week during the season, but, unlike, say the Oscars (ha!), my opinion is as much a guess, built off of the seeding, versus an expert point of view on how each team matches up against the others.

I wonder how Bobby Knight and Digger Phelps do on their bracket picks (both, which I am sure you know, b/t/w, are former college coaches and current ESPN analysts)?  The experts should beat me nearly every time.  The odds are that one of the number 1s will win the tournament.  The horde (and my second bracket) has Kansas as the winner.  The experts say they are the best by a meaningful margin.

But it’s a fairly well established notion that in order to succeed in an NCAA bracket you have to pick some upsets.  How do you do it?  Best guess?  Educated guess?  Study and know your stuff.  Understand the match-ups.  Pick the unknown underdog. Dartboard?  Or is the notion of needing upsets to create a winning bracket false?  Where’s the data?  Is it reliable?  Maybe the seeding is off? Is NCAA seeding reliable?

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If you’re curious, here are my 8 first round upsets on my gut-shot:

1.    Houston (10) over Maryland (4)

2.    No. Iowa (9) over UNLV (8) (9 beats 8 – not a major upset)

3.    GaTech (10) over Oklahoma St. (7)

4.    UTEP (12) over Butler (5)

5.    Florida (10) over BYU (7) (some people like BYU to go to the final four to play in Salt Lake City – I say no way)

6.    Wake Forest (9) over Texas (8) (Texas was ranked #1 in the country earlier this year only to fall hard)

7.    Missouri (10) over Clemson (7) (I never have any luck picking Clemson)

8.   Louisville (9) over Cal (8) (again 9 beats 8, no biggie)

Of course my big upset is K-State going to the final four.  Good pick?