Don't Let Your Startup Be Like The Red Sox

On Monday I wrote about a problem I’ve seen in a few startups recently. Your people must be the most important part of your startup — above everything else.

As I turned on my “I’m about to fall asleep” edition of Sportscenter, I heard a wonderful example of this problem from the sport of baseball. I say wonderful because I’m a Yankees fan, and this segment was all about the disastrous season of the Boston Redsox.

As it turns out, Bobby Valentine, who was brought in to right the ship and replace Terry Francona after last year’s historic collapse, is one misstep away from being fired. There are several reasons for this, but at the end of the day it all comes down to the team’s performance. Bobby V is not a great leader and his team doesn’t believe in him. Let’s take a look:

  • In spring training, he publicly called out his own players — Kevin Youkilis being the main target. Publicly. Not behind closed doors. Not directly to the players in question. But Publicly. Needless to say, this immediately raised eyebrows.
  • Then the team got off to a rough start. 4 wins and 10 losses to be exact. And there were calls for Bobby to lose his job right then and there because the players weren’t responding to him as a coach. This quote from Dustin Pedroia at the time says it all:
"I really don’t know what Bobby is trying to do. That’s not the way we go about our stuff around here. He’ll figure that out. The whole team is behind Youk. We have each other’s backs here."
  • Youkilis, who was (un)surprisingly off to an unusually slow start, had to miss 3 weeks due to an injury and Will Middlebrooks — a talented rookie hungry to make his mark — started hitting really well. This was an opening to make a move and get rid of Youkilis. Yes, get rid of the guy who helped lead the Red Sox to 2 World Series Championships and finally break the 86 year old curse of the Great Bambino. And just like that, Youkilis — the Greek God of Walks — was traded to the Chicago Whitesox, so that Middlebrooks could play every day and Valetine could have his way.

So let’s fast forward to today. David Ortiz and Wes Middlebrooks are both on the Disabled List with return dates unknown, leaving the Red Sox struggling to find both a third baseman and a DH. And by struggling I mean Boston is currently 12.5 games behind the Yankees in the Division, 6.5 games out of the Wildcard with 5 teams ahead of them, and losers of 9 of their last 13 games.

Oh yeah, by the way, Youkilis is now playing for the first place Chicago White Sox. In 2 fewer games with the White Sox this season as the Red Sox, Youk has almost doubled his Home Runs, Walks, and RBI’s compared to his numbers with the Red Sox. Not bad.

The point is the same as the post on Monday. TAKE CARE OF YOUR PEOPLE. They need to know that you have their back no matter what, know that you are fully committed to them, and know that they can trust you.

As a Yankees fan, I’m glad to see the Red Sox struggle. I thought it was foolish to bring in Valetine when they announced it, and I think it’s foolish they still have him there now. They need someone who is going to fit in with the Red Sox culture and be able to have the Red Sox players overachieving, not underachieving like they are currently.

Don’t follow in the footsteps of the Red Sox. Make sure your startup puts your team first above all else. That’s the only way you are going to get the most out of your team and that’s the only way you are going to be able to build greatness.

"What a Long Strange Trip It’s Been"

(Note: I’ve linked to the video although you may need to be tripping on acid to enjoy some of the special effects. Amazing opening to a show though - playing Truckin’ into Smokestack Lightning. I grew up listening to the Grateful Dead and heard some ridiculous stories of the shows they used to put on)

I attended the Yankees game this past Saturday, and on any give day at the Stadium you might witness history. It just so happened, Derek Sanderson Jeter went 5-5 recording his 3000th hit (and 3001, 3002, and 3003 as well). This was my view. By far, the most memorable and historic sporting event I have ever been to.

An amazing accomplishment by a truly deserving individual.

When I first entered the working world, I aspired to be just like Jeter, but that has all changed.

I envisioned my career path and went as far as telling colleagues about it — I wanted to be just like Jeter. Come up through the minors and spend my whole career with one team. I think that is such a classy / under-appreciated move, which is why I love this. I started as an intern and wanted to ascend to a very senior global head of blah blah blah for the international bank I was working for.

I learned a lot, got promoted constantly, made decent money, busted my ass, and was brought on to lead teams and fix very high profile and challenging projects (read: projects that were failing miserably and I had to figure out to how turn them around).


The work environment was absolutely terrible. There were a few standout people who made it bearable, but they were the exception. Maybe it is just the large, international, non-US based corporation that I despised, but I think it was a lot more than that.

I eventually made the decision to leave and become a financial advisor and then start my own wealth management firm and now cofound a tech startup. I thank myself everyday for taking that leap of faith into the unknown. I realize now that a career path at a company that makes you miserable and treats its employees like dog shit on the bottom of their shoe does not translate to spending your entire career winning championships with the New York Yankees.

Four things I’ve learned..

1 - Corporate culture should never be underestimated

2 - How the hell was I supposed to know what to do with my next 40 years on this planet when I was a 22 year old punk whose biggest concern was recovering from a hangover

3 - I get why people hesitate to leave a shitty job especially in this economy but don’t ever feel like you have to stay because you owe something to the company. That’s bullshit. If it’s an awful environment and you just expect it to get magically better one day, you are the definition of insanity

4 - What a long strange trip it’s been

(Special Bonus: The next time you see me in person ask me why this line perfectly describes my experience at Mardi Gras 2005 “Busted, down on Bourbon Street / Set up, like a bowling pin / Knocked down” I promise you’ve never heard a story like this and you won’t be disappointed)