America’s game: apple pie, baseball… and angel investing

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MattDunbar

On Father’s Day weekend, I indulged a bit in watching the last round of the U.S. Open golf tournament and the last game of the NBA Finals. My lovely wife, who doesn’t exactly share my interest in sports (other than college football), opined that she found the sports to be boring — except right at the end when you find out who’s going to win.

She went on to remind me that the most egregious offender in the sports world for her is baseball, recalling the games I recently watched during the NCAA Tournament. For her, it seems to be a very long game with perhaps a few brief moments of excitement, until finally, there’s a winner. As we discussed it further, she insightfully compared baseball to my work in angel investing. Not that it’s boring — but it is a long game punctuated with intense episodes before determining the end result.

Since we are entering the most American of holiday weekends, and since America’s game — baseball — is the last remaining active major sport in the U.S. for the summer (at least until the Olympics), I thought it was a fitting time to extend her analogy. While you’re celebrating our freedoms and enjoying your apple pie and baseball this Fourth of July weekend, you might consider how America’s pastime on the field is much like that other important American institution of angel investing.

Swinging for the fences

 

Perhaps the most obvious comparison starts with at-bats. Much like batters, angel investors are taking swings with each new startup investment, hoping to hit a “home run” that generates a return of several times their investment. Given the risky nature of startups, a strikeout (complete loss of investment) or out (partial loss) is the most likely outcome, but with enough at-bats and discipline at the plate, angels can accumulate enough extra base hits and home runs to generate very attractive returns — and a batting average that bests the .350 mark of the best hitters in the Major Leagues.

Anticipate curveballs and errors

 

Continuing the at-bat analogy with a slightly different twist, investors (and entrepreneurs) have to anticipate curveballs. When it comes to launching and growing a young company, the market rarely throws fastballs right down the middle. Instead, startups and their investors have to keep their figurative eye on the ball, clearly focused on discerning when and where to use their limited resources (swings) and not chasing wild pitches (seemingly shiny new opportunities that can quickly drop out of the strike zone). In the field, when things don’t go as planned and inevitable errors are committed, they must quickly regroup from the mistakes and focus on closing the next sale (getting the next out).

Play the long game

 

The nine innings of a baseball game — and the 162 games in a season — require a long-term strategy for success. If a team burns up a pitcher’s arm in the early innings or early in a season, the short-term benefit can be disastrous for long-term wins.

Similarly, investors must approach their angel portfolio with the long view in mind, as most investments take several years to reach the ninth inning. If the investor deploys available capital too quickly on too few pitches, the chances of long-term success are drastically diminished.

With the right discipline, process and mindset, winners in both baseball and angel investing can amass big wins and give us legendary tales of victory. Similarly, losers can be quickly forgotten — but they can also learn valuable lessons from the losses that translate to better outcomes for the next game. I will refrain from further belaboring the analogy here, but suffice it to say there are countless other ways we could compare baseball and angel investing.

And of course, every analogy eventually breaks down if carried too far. Sometimes a startup doesn’t get to play the full nine (or extra) innings, as failures or early exits could occur in any inning along the way. The maximum value of a home run can’t exceed four runs, but there’s no theoretical limit to the size of the returns on an investor’s at-bat. When the startup is the pitcher trying to land an investment, straight fastballs are the order of the day instead of the curveballs to be anticipated from the market. This list goes on.

Despite the obvious limitations, the comparison of baseball and angel investing is an instructive one for investors to consider — and despite my wife’s view of the game, a fun one to think about during the dog days of summer. As you enjoy your apple pie and other Americana this weekend, perhaps you’ll think of additional parallels and be inspired to play ball yourself.

If you’d like to join up with our angel investor team, we’d be happy to provide you with coaching and plenty of at-bats. Check out our lineup at upstateangels.com.

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