Schedulefly’s ribbon-cutting ceremony

Sometime in the spring of 2007 my boss walked into my office and took a seat. He, being a real straight to the point guy, asked me “What is your plan with Schedulefly?”. I responded with “Man, I don’t know. I don’t have one”. He then asked what it would take to get it ready and was I interested in doing something with it with his help. I thought about it for several seconds (while absorbing the fact that this sharp business leader that graduated from Harvard and UCLA was interested in making Schedulefly a real business) and then said “sure!”. It was the shortest and most productive meeting I had had in years.

Back then we were both working for a business called First Research that had recently been acquired. Tyler was my boss there and had decided to move on once our business was sold. I didn’t blame him. The writing was on the wall. I was just thrilled that what he wanted to do next was take the software I had written – which was running on a Dell PC at my house and being used by 2 or 3 restaurants – and make it a business. I had written the software a few years prior to this and I had shown him the software some months earlier and explained why I created it and how a few places were enjoying using it. At that time I had no idea he would take a seat in my office soon after and do what he did. Sometimes I look back at how things lined up for us and for our business then and in the next several years – and I get the chills. Timing was literally everything.

Later, Wil would join us. Wil was also an incredibly sharp guy from First Research. I recall that day Wil joined us and the email I got from Tyler that simple said in the subject line “WIL!!!!!!!!!!!!!!!!!!!”. Nothing in the body of the email. If you knew Tyler – you’d smile at that. Tyler doesn’t get excited much – at least publicly. It was a big day and it was clear that Tyler felt his joining us was extremely important. He was right. Then a few years later we brought on Charles and then Hank – both of whom were also at First Research and are badass technicians and they hit the ground running. Again – I really believe the timing of this all lining up like it did is a once in a lifetime event. It was meant to be and never once felt forced or that we were settling for something that was not just perfect.

So Tyler and I continued to talk in my office that day about what was currently going on with the software and what kinds of things we needed to do in order to get going. Real basic, yet important, things like where would we host it? How would we get restaurants to hear about it? How would we setup new free trials? What would we charge for it if they liked it? How would we accept payment? What lawyer should help us get started? Real basic stuff that mattered right then. We quickly found a place to host it – a small hosting company in Raleigh – and it cost us $400 per month. Since the pricing he and I had settled on for joining Schedulefly averaged about $40 per month – we agreed our first objective was for he and I to go find 10 restaurants to pay us $40 per month. That would pay for the hosting. That was the goal even though he and I are not salesman and truly can’t stand selling – we knew we had to do this. As bad as we were at it – we muscled through it and made it happen…mainly with email marketing and a few dreaded in person visits to restaurants. Since then – we’ve never had sales goals or quotas of any kind other than being excited when we reached 1,000 and 5,000. Can we get 10,000? Who the heck knows – I honestly didn’t know if we could get 10 back then. But we did.

I know I’ve blogged about all of this in the past – and it’s because I think about it often. I think about the past and how it lined up and how lucky the 5 of us are and how rewarding this has been. A friend of ours and the guy who started the company where the 5 of us met has written a book on startup entrepreneurs and the challenges they face. It’s got some great success stories in it and it also tells the detailed story about Tyler and things he did (or didn’t do) early on at Schedulefly. It’s a great story. The book is called The Hockey Stick Principles. Check it out!

Here we all are – about 3-4 years ago. The first and last time we have all been in the same room since starting our company.