8. As a CEO, what is an example of a good day and of a bad one? I’ll give a few from the early days. This is pretty fun: A Good Day: I’m running out of cash in the earlyish days-- and somehow convince a key customer to pay us an $300k additional pre-paid... even though contract doesn’t require it and isn’t up for renewal for 10 months. Gets us six months more runway. Company survives to live another day and raise our Series B. I had a terrific, quiet party of one. A Bad Day: The Day It’s Clearly Hopeless. For me, this was about 9 months in. No matter what, we’d never be able to get to $1m in revenue fast enough, let alone profitability. The spreadsheet just didn’t pencil out. We weren’t going to be able to raise any more capital and there was just no way the math could work. Before that day, it may be grim -- but it’s different once you hit that certain day when you know it’s mathematically hopeless. A Good Day: Cash Flow Positive. Boom! We hit this around $4m in ARR. No more VCs getting to call the shots. Now no one could kill us but ourselves. Time to plan the first company retreat! A Bad Day: Crappy M&A Offer Pulled in First Year. Yes, it was a totally crappy offer albeit from a good company but from “the day it’s clearly hopeless” point on (see point #2), I was pretty deeply bummed to have this option pulled out from under me. A Good Day: Hiring My Real VP of Sales. It was pretty brutal for a while there. Trust me, until you’ve hired someone great, you don’t know. And then you do -- and it’s magic. All of a sudden, I could focus on what really mattered. Bringing someone super talented into the company brings a positive attitude and a whole team with them -- just epic. A Bad Day: When I Had No Salary And Didn’t Get My Requested $10k Bonus Even Though I Brought In an Extra $250k All-Cash Upfront Deal. Argh. A Good Day: Dec 31, 2009; Dec 31, 2010; Dec 31, 2011; Dec 31, 2012. When we killed it every year on the last day of the year. Exceeded the plan and our own expectations. New Years was spent in the office. It was just too fun to see the SAASTR.COM 8