11/11/2014 03:54 pm ET Updated Jan 11, 2015

Being Honest With Myself: I Never Played Third Base

Getty Images

Last night I was cleaning out an old shoebox of random stuff in my house, and I came across my Little League baseball card from 1988. After staring at the front of the card for a few minutes as if I'd just found a Honus Wagner card and a true gem of baseball history, I yelled to my wife to come inspect this piece of Smithsonian history like a proud father.

I then flipped it over to see my "stats." Yikes.

My stats were nothing short of underwhelming: I was 10 years old, 4'4 tall, and weighed 60 pounds. Clearly, a powerhouse body of a ballplayer. I had three hits for the entire season and a ton of walks, probably because I was too short for a pitcher to target my limited strike zone.

On top of that, my listed "favorite player" was Mark McGwire -- and all I knew about juicing in those days was drinking bug juice between innings. Plus, I listed the Mets as my favorite team, which as an adult and Yankee fan shall forever haunt me.

In addition to seeing all of this, seeing the card took me back to my playing days: as a ballplayer, nothing says badass like the good old turtleneck that my mom generally required me to wear under my uniform. Said turtleneck was a staple of my wardrobe for my first fourteen years.
Getting past ALL of that, here was what popped out at me as the problem from my card:


It's been over 20 years, so like many ball players before me, it's time to come clean. This has nothing to do with the Mitchell Report, Clemens, or Canseco. This has to do with being honest with myself. No more hiding behind revisionist history and my baseball card.

Here it is: I didn't play third base. Ever.

I generally found myself assigned to "deep left-center-something or other." I was terrible. Sure, Coach Milo let me play third in a few practices, but the chances of me tossing out a runner from third to first were about as good as my getting a text message from President Obama to spend the weekend at Camp David for a "catch-up session."

The relevance of the above? It got me thinking about many meetings I've been having and the resulting diligence.

Honesty in business is vital, and one's name is all they have. As it relates to the above, I've learned over time that sometimes the hardest person to be honest with is yourself, and it's the same as it relates to a startup. Of course I wanted my coveted baseball card to say that I was a third baseman, and of course startups and businesses in general want certain goals and KPIs to have been met within certain timeframes.

In many cases, it's simply a matter of patience and hard work. Results and positive cash-flow rarely happen overnight, but that's okay, and fine to be upfront about when meeting with investors or even within internal company discussions.

However, I find that it has become somewhat commonplace for companies to couch certain desires as if they are definitive realities. Simple diligence often clears up these over-statements, but I always find the best relationships and best negotiations are ones when all parties are coming from positions of genuine honesty from day one.

Is it the most hard-nosed tactic? Nope. Does it lead to great relationships and better business dealings? Absolutely. Example: in reviewing financials, I'd rather see an off-month up-front and hear a likely plausible explanation as to its cause, rather than have to back out the numbers to see that a recent month wasn't as successful as it's being couched.

Fortunately for this writer, '88 was pretty much the end of my ball playing career; I was traded to a few teams, but third base and the Hall of Fame just didn't happen for me.

Moral of my brief story: as an investor, as a mentor, and as someone who loves working operationally with companies, I would rather hear about the good, the bad, and the ugly up front. For startups, that means being honest with oneself about where you are, where you want to be, and I am always happy to work with you to get there together.