Today it was announced that Guy Kawasaki sold Truemors to NowRepublic. For those of you who do not remember, Truemors was Guy’s little experiment last year to prove that you could launch a Web 2.0 startup on the cheap. I believe all told, he was about 10k in (give or take a few, but who is counting, right). There have not been any numbers released on the actual sale price, but given that NowRepublic has raised two rounds of funding and the last one being a little over ten million, chances are Guy did not make a mint on this sale.

However, it begs the question, what constitutes a successful exit? Does it come down to shear percentages, or is it a hard dollar figure? I would have to assume that a successful exit is more of a percentages game than anything else, but I could be wrong. I mean, if you can get a 100x return on your investment, does that make for a successful exit? If so, if Guy sold Truemors for a million, is that a successful exit? I would have to go out on a limb and say yes, although in the grand scheme of things, one millions dollars is not a whole hell of a lot (to me it is, but to those that deal in this sort of business daily, it is not a ton of dough).

So what about a company that raises ten million and sells for sixty million? At first glance, that seems like a pretty substantial sale price and one might consider that a successful exit, but is it? The investors are only getting a 6x return on their investment, whereas the example above they are getting a 10x, so which one is more successful? I would also venture to guess that in this example, the investors would probably not bite on a sale for that price and want to hold out for more, but is that the right thing to do? What if the company will never be worth more than the sixty million, should they not get out while they can? I know there are a ton of factors that go into the decision, and I am grossly over simplifying my examples, but the question still remains, what makes a successful exit?

In Guy’s case, I would argue he made out pretty well, after all he is now the new chairman of NowRepublic and I am sure that comes with a pretty decent salary .

A defining moment could be described as a time in life in which we let our lives be defined in an instant, in other words what is happening at that moment sums up our life. Pretty heavy shit if I do say so myself. I have had the pleasure of experiencing several of these in my personal life, from meeting my wife, to getting married, to watching the birth of all my children. To be able to bottle up the emotions that coursed through my veins at that moment would go a long way in defining who I am and what my purpose in life is. Of course, these defining moments have been positive for me, but I have had some “negative” defining moments as well. From loosing my best friend as a teenager to my parents divorcing when I was seven, they were defining moments in my life that could molded me into something completely different had I let them remain negative. Instead of letting those moments define me in a negative light, I chose to treat them as an opportunity to better myself, and as a result of those “negative” defining moments, I am a better person.

Much like individuals, companies / organizations / teams, also have defining moments. Sometimes those defining moments test the boundaries of what you (the company / organization / team) believe to be what you are really about. Defining moments are not always positive, but I believe they all present opportunities. In other words, there may be a point in time where you company is in a downward spiral. You have taken ungodly amounts of money from investors, your product had been delayed, you were not received as well as you thought and you have not idea what to do next. This is a defining moment, your backs are up against the ropes and you either a) throw in the towel or b) come off the ropes with guns a blazing and take control of the situation and redefine yourself as a winner.

Not everyday to you have a defining moment, but when you do, take hold of it and remember why it is defining you and strive to make the best of it, no matter how it originally defined you.

It is funny, being a parent and raising four kids teaches you a lot of life lessons (imagine that) that can be applied to various situations, both personally and professionally. One of the things I have been working on lately with my children is the notion of continuing to try harder and you will eventually succeed.

I am reminded of a time when I was in kindergarten and the year end play was “The Little Engine that Could”. Back then, it just seemed like a fun story about a little engine that was trying to make it over the mountain top, but could not get any help from any of the passerby trains. So, to his (or maybe her, I am not sure what the “actual sexual orientation of the engine was and I am not even sure that it mattered) delight, he / she continued trying and finally made it over the mountain, hurray! What I now know is that fun and innocent little story has great meaning when applying it to life and especially in raising children.

In “The Pursuit of Happiness” there is a point where Will Smith tells his son never to let someone tell him that he cannot do something or accomplish something (my paraphrasing there, sorry if I did not get the quote exactly right). Little tidbits of advice and guidance like this go a long way in shaping the confidence of your children, it also teaches them that in order to achieve / obtain certain things that you have to work really hard at them. I know that it seems trivial and common sense, but it is amazing at how powerful these little lessons can be.

So the next time that you are feeling like you are ready to throw in the towel, remember back to your childhood and the story of The Little Train that Could and keep chugging away, you will eventually cross that mountaintop.