So, what’s it like to sell your first company?

Short answer: It is insane, it sucks, its awesome, its out of this world experience.

For details – read on…

In December of 2002 I was the CEO of my first company, Information Laboratory. The company developed a product called Small Worlds, which helped find architectural flaws in software systems. A software tools power house, called Rational Software, decided that it needed to buy my tiny startup.

Rational found my company in an exhibit hall, at a Software Development conference in suburbs of Chicago. At the time, I thought that Martin Fowler, the father of refactoring, was god-like (I still do). Also, I met Robert C. Martin in person, and was drinking Agile Software cool aid (I still do).

In any case, a biz dev person from Rational Software spent several hours in front of our station. He liked what he saw. A few weeks later I was presenting our software at Boston HQ to a group of mildly amused execs. My champion was a fellow named Sam, who I hold in the highest regard to this day. Sam was awesome. He totally got what we were doing. He was the one who pulled the trigger.

A few weeks later, I got a call from a fellow named AP. He worked in Corporate Development and was super friendly. He was very discreet and explained that our tiny co was of interest to the big co. Needless to say, we agreed. I mean who wouldn’t. This was post 9/11 world ,and we literally had no clue.

I called up my head of biz dev and was bragging about how lucky we were. He was a very seasoned guy, and said – dude, don’t celebrate yet, until the check is in the bank. I laughed it off – what could possibly go wrong??

Well, mid December, we read on CNN that Rational Software entered into definitive agreement to be acquired by IBM.

Days of excruciating radio silence followed. Then I got a call from Sam. He said that it was all good, and our deal will still happen, once IBM/Rational deal closes.

That deal closed on Feb 20, 2003. Days and weeks of radio silence followed. Finally sometime in March we got a call. More meetings, and negotiations followed.

I thought that there was nothing to negotiate. Still IBM/Rational combo felt like there was. The offer kept getting smaller, and our warranties about IP kept getting bigger.

Then Sam called me and said – hey, its all good, but his last day at IBM was in a few weeks. Turns out Sam got another job, and a new fellow, named Vincent, will now take his place and be our new champion. The transition triggered a whole new visit to HQ. We had to re-pitch, convince Vincent all over again and all that jazz. At the time it seemed like business as usual, but of course now, in 2013, it just seems totally crazy.

Once Vincent and co were convinced, a corp dev fellow named AP re-appeared.

But he was not so nice any more. To be honest, I was dreading every single phone call with him. I was so young and naive, and easy to mess with. Things kept changing. Every single time some new constraint, or whatever was added. At some point my wife was so fed up that she said she is going to buy a plane ticket, fly over to California and kill AP. Good thing I stopped that from happening.

Its all good. The ending was warm and fuzzy. IBM/Rational acquired my first company in June of 2003. At the time, it was life-changing money. Looking back, of course, it wasn’t.

Still it was meaningful. It afforded us the most amazing house we could wish for. More than that, it was an important event for me personally. It gave me a first taste of success. And that, in turn, breeds confidence and courage. To do it again, to start something new.

So you will say, okay, whatever. The experience of selling the company in 2003 is not relevant in 2013. And yes, you are right, it is not. The experience is totally not relevant. What is relevant are human emotions.

The way you feel when you sell your company in 2003 is the same as when you sell it in 2013.

Its over, its done, its crazy, its awesome. You love the world, you hate the world. You will never ever, for as long as you walk the planet do it again. But of course you will. You have to.

Personal Startups