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Last week I had a drink with an experienced exec that has worked in big companies all of his life and never worked for a startup. That’s fine, not everyone is made for a startup life.

But at one point, in the conversation he told me that he’s been tempted by startups a number of times but reminded himself of that old saying “the devil you know is better than the devil you don’t”.

I paused when I heard that comment. I believe that saying is counter productive.

To me, it says that the person is unwilling or unable to take chance or make a decision where the outcome is unknown. I told him that the outcome is rarely ever known.

I thought about that conversation last night while watching the Super Bowl. The Saints started the second half with an onside kick. I was blown away. What a gutsy call. I’m not sure how many teams recover an onside kick but that didn’t stop the Saints from giving it a try. They just went for it. And it paid off big time.

Gutsy calls knock on your door when you least expect it. Every startup I’ve been part of had uncertainly baked in. The first gutsy call I made was at 22. I quit my first job, took my life savings of <$3k, packed my life possessions in the back of my hatch back and drove from Boston to San Francisco in 4 days. I had no idea what life was going to bring.

Most people I’ve met in SF actually came from somewhere else. They left it all behind and didn’t think about the devil they know vs the devil they don’t. They just went for it. Maybe that is one reason why SF is a special place to me. It’s a gathering of folks that are taking personal risks.

Now, don’t get me wrong, people take risks everywhere but my direct & personal experience with SF transplants is an interesting datapoint (for me at least)

Most people that I’ve met who have remarkable life stories always looked back on their gutsy calls and were happy that they took that chance. Even if it didn’t work out in that specific instance they were better for leaving behind that safe cozy place.

“Up and to the right”

It’s a common expression - especially in the world of startups. Startups tell themselves and their prospective investors that they predict big time growth (user adoption, revenue adoption etc). The chart ramps slowly and then pow, magic happens. All smooth, nice and neat.

And sometimes it does happen.

But usually it doesn’t.

Making progress is requires crazy hard work and focus. Some companies are engineering focused and that works for them. Others are more product focused and that works too. It depends on the culture. Just look at apple and google. two different approaches and two different cultures. Both are widely successful (keep in mind both companies have plenty of products that never worked out).

One thing that i’ve seen time and time again is it’s almost always a series of things that make “up and to the right” happen over time. It’s not one thing. It’s hiring the best people on the planet, making the product better, thinking about things in a new way while maintaining the vision, focus & determination. It’s dealing with setbacks productively and with intellectual honesty and self awareness.

The bumpy road to “up and to the right” also happens with our careers and life experiences. Often, we share one side of our lives on blogs or on our resume. The whole story is of course much more jagged (and by the way, much more interesting).

I caught up with someone I admire yesterday in San Francisco. This is someone that has accomplished so much and he also gives back to the community in extraordinary ways. He told me his life story. There were many dark dark moments in his life where he had debt coming out of his nose, he had been fired, he couldn’t get a job and was alone in a strange new community.

But he had his health, his will, talent and good fortune as well (met great people along the way). His life wasn’t  hardly a smooth “up and to the right”.

Mine hasn’t been that way either.

I recently received a question from someone that follows me on Twitter and this blog. She asked me how i can keep such a balanced family life, work life and relationship with my wife. I guess from my various tweets she sees me working hard, going out with lauren and hanging with my kids. But it’s never that simple. At any given moment I think I’m doing better at one of those things vs the other and it’s a constant balancing act. Sometimes I do pretty well and other times I do a complete faceplant.

But I get back up again when no ones looking :)

This post is starting to ramble. I took the red eye flight last night so you have to forgive me.

I’ll end this post by encouraging you to not get caught up with up and to right with everything and with each moment in your life. Because it’s rarely if ever a smooth up and to the right.

Enjoy the ride. And take time to figure it out.

The iPhone is good at many things but battery life isn’t one of them.

To make matters worse, you can’t swap out the battery.

I carry the power cord around me everywhere when I’m traveling and I’m always plugging in. But that isn’t easy to do. Many coffee shops (also known as my traveling office) don’t have exposed outlets. And sometimes, I get so caught up meeting a founder that I just forget to plug in.

Then my iPhone goes from phone to brick. We’ve all been there and it sucks.

So i recently picked up the Just Mobile Gum Pro battery pack. A fully charged battery pack can charge my iPhone 2-3x times via usb.

I brought it with me on this trip to San Francisco. It’s been a life saver.