Another April 1st beginning for NYSE Captain Tim

On April 1, 2013, we were on the middle of doing an IPO roadshow to take Rally Software (RALY) public.

In many ways this was the pinnacle of my career and also marked the beginning of the end of my career as a software CEO. I took great risks in the past, as you just read. I sailed across the Atlantic in a spring storm in the North Atlantic and I founded and sold a successful startup called Avitek but to take a company public seemed like a BHAG (Big Harry Audacious Goal) that was just too large to contemplate.

At Avitek, I was constantly confronted with the possibility that the company would fail and that my family would be broke. We were perpetually about 3 weeks from missing payroll and while there was a time early on that I could write a check if we had a shortfall in cash, that time has long passed by the time that company was sold in the fall of 1999.

At Rally, after 10 years at the helm with my business partner Ryan Martens we took Rally public. I had one hell of a time absorbing all the accolades of such an endeavor and I admit that the adrenaline rush of taking a company public rushed through my veins for several months afterwards. It was definitely the hardest single milestones that I had professionally achieved and yet the anxiety of a failed IPO loomed ominously over my head non stop. We agreed to be sold to CA right around April 1, 2015 for $19.5 a share.

Sitting hear at the navigation station of our high performance catamaran aptly named Agility, my mind races with anticipation of the coming adventures in the South Pacific and all over the world. Yet in the back of my mind, I’m cognizant that this could be the adventure of a lifetime or the end of my career as a Captain of the sea.

Cold front moving fast by our position S 28 30.503 W 94 37.549. AWS 20 25Kts max 30Kts, sailing at 7 Knots +/- under double reefs heading 250 degrees on route to Easter Island. Expect landfall in 6 days.

Now, I’m going to sit on the back deck of Agility and watch the stars and the sea for a while.

P.S. just saw an amazing shooting star blast across the Milky Way while looking at Mars.