Nov 2013 19

Vulnerability Makes You Look Smart
Aug 2013 13

I recently met with a young entrepreneur who has had some recent successes. We talked through some of the wins and how they came about with his new company and the momentum he felt like he had. Intrigued by where he was hoping to take things, I asked what I could be doing to be helpful going forward. He responded, “There’s nothing that comes to mind, I think we’re good.”

Having seen my share of start-ups over the past few years, not needing help from someone  can only mean one of two things:

1) You don’t like the person and are doing your best to keep them as far away from you and your company as possible. You think they have the potential to be a hanger-on and have no value to provide.

OR

2) You’re in denial about how hard the road ahead is going to be and haven’t even begun to think about what it means to build a company from scratch.  Not knowing how someone can help is tipping you hand that you haven’t even scratched the surface of how hard the road ahead is going to be.

Some of the best entrepreneurs and professionals I know are the most skillful at involving anyone and everyone in their initiatives. Not in a “cry for help” kind of way, but by understanding who their audiences is and what value they can create together. When we play the tough guy and show no vulnerability, we are missing out on the chance for others to work their magic on our behalf. Not out of pity, but out of caring and the desire to see us succeed in our endeavors.

The next time someone asks how they can be helpful, think about who they are, what they’ve done in their career, and if nothing else, look to them for advice about a situation you know they’ve encountered that you may run into further down the road. The last thing we need is more tough guys that don’t need anyone else. Being an entrepreneur is tough enough as it is, why handicap yourself further by doing it alone?

All In
Jul 2013 16

Maybe it was the scotch, maybe it was that I had the chip lead, or maybe there’s just something in the air, but, last week during poker night, I realized something about the way I approach each hand that is dealt. And then next morning over coffee realized it is the same way I approach life.

I’m always looking to go All-In.

Now, I don’t mean on every hand, but I do mean, that my “tell” (sign that I’ve got something exciting) is that I bet. I have no problem sluffing cards that aren’t quite good enough. There is definitely an opportunity cost to not staying in hands longer, like knowing you’d have had the winning hand after all the cards are dealt, but there is something to be said for knowing how you play and what you’re willing to risk.

The same is true when evaluating options and making choices in life. I’m constantly finding that once I go “in” on a hand, I am quickly confident enough to go All-In. If something is worth doing, it’s worth doing All-In.

Or said another way:

 

Invest 90 Minutes
Jul 2013 07

I aspire to have Jerry Colonna to be my professional coach.  We swapped notes last year and he told me he is at full capacity and isn’t accepting any new clients. I’ve gotten to know a couple of entrepreneurs to have made it on his client list before he closed it and they’ve told me that I am in fact missing out. So, when Jason Calacanis had Jerry on This Week In Start-Up, I was intrigued.

After I pressed play, I took three full pages of notes and became even more determined to earn a spot on Jerry’s client roster int he future.

I considered posting my notes here, but then reconsidered as each of the pieces of wisdom that Jason and Jerry share is incredibly and refreshingly personal.

I know that 90% of you reading this will not invest the 90 minutes to watch this in its entirety, but for those of you that do, I know that you will see the adventure ahead differently.  When you’re finished up, shoot me a not or leave a comment below, would love to hear which piece of the discussion jumped out to you most.

UPDATE: Jerry mentions a talk he gives called The Crucible of Leadership. I found a great summary he wrote about that talk over on Fred Wilson’s blog HERE. Another great piece of thought provoking questions and deep thoughts worth pausing to explore.

Working Smarter
Jul 2013 07

I recently played the best round of golf of my life. It was the first round of golf I’d played in 14 months. Heck, the first time that I’d swung a golf club in 14 months. I was also playing the Ocean Course at Kiawah Resort in South Carolina, the course that Tiger Woods called, “one of the more challenging courses I’ve ever played.”  Did I also mention that I was playing with borrowed clubs?

With all of these factors in mind, you can imagine how frustration it was for the other golfer I was paired with who plays twice a week to watch me play as well as I did. It actually appeared to make him play worse, like I was getting in his head on a Sunday round at the Masters.  I started feeling bad about it, but not enough to stop me from crushing my 3-Wood 280 yards down the fairway on the 18th hole approaching the club house.

Enough with my not-at-all-humble brags, what is the point of the story? Where is the ego fueled rant headed?  There are two things that factored into how well I played that day: What clubs I played with and who I played with.

What I played with: I mentioned I played with a borrowed seat of clubs but I didn’t mention that they were brand new Titleists with the biggest sweet spots I’ve ever seen.  I grew up playing on a set of 1967 Wilson blades that I inherited from my 6-foot 5-inch Grandpa Anderson. They had longer shafts which was helpful for my height, but absolutely nothing but a bent piece of metal with grooves as the club face and therefore no forgiveness for my tendency to slice the ball. These Titleists were more forgiving than a soon to be retired priest.

Who I played with: I mentioned the avid golfer that I played with, but I didn’t mention that part of the tradition at the Ocean Course is that ever group goes out with a caddy. My caddy was Brandon Hartzell, a semi-pro golfer who just missed the qualifier for this year’s U.S. Open. I got to the course early and he accompanied me out to the driving range. At first, I was taken aback by how conversational he was while I was warming up, but what I later realized was that 15 swings into my warm up, he knew my swing better than I did.  He watched me go through my irons, then my fairway woods, and then my driver on the practice range and didn’t let me pick a club the rest of the day. He knew exactly how far I could hit each club and how I should play each shot. His understanding of my all but hibernated golf game infused me with confidence that I had no business having.

I recently wrote a blog post about only having one gear on my bike and some of the virtue that I have found that raw experience to give me. A good friend and all together more accomplished cyclist, Adam McManus, tweeted back to me that he understood where I was coming from, but also for me to not discount what can happen by working smarter and some day growing up to a bike with gears for all kinds of routes, hills, and distances.

The same could be said for the precision that I used to cling to with my 1967 golf clubs. While both my one speed and ancient clubs require me to be ultimately much more intentional about the way I operate. But, at a certain point, graduating up to the next rung isn’t just about raw skill but the honing of the foundation you’ve built and going deeper into the realms of possibilities by working smarter after having worked harder.

Working smarter and working harder are not mutually exclusive and the best of the best understand how to do both in harmony.

(If you want to read more about the great time that Annie and I had in Kiawah, check out her post on National Geographic HERE)