Today Wil and I were texting about some random funny stuff and one of the serious things was that it’s now September and we have 325+ restaurants in a free trial right now. We thought it was cool because normally by the 4th quarter of the year we start to slow down a tad when restaurants are thinking less about change around their restaurant and more about the rest of the year and the upcoming holiday season – or at least that’s my explanation. We’ve watched that trend for 7 or 8 years and understand it and don’t try force more business than we should naturally be getting – so it’s predictable and expected – but it’s cool to see each season stronger than the last.

Anyway – talking about this made me think about memories I have had over the years about small milestones along the way and it’s crazy to see think how far it has come – just one day at a time. For instance, I remember having more free trials than paying customers and was so excited for the day to some when the paying number would reach and surpass the trial number. Today we have 325 trials and 4,385 paying customers.

I remember me and Charles frantically working one night about 7 years ago (when we had just a few paying customers – 5 or 10 or so) when our “shared” server that we were currently leasing ran out of disk space. What. A simple problem and a terrible problem all at once. Like a plane running out of gas or something. It was time to move. P.S – Charles had another job and was not responsible – I was.

I remember being on vacation with my wife’s family and toasting our 100th paying customer that summer.

I remember the next day (after hitting 100 customers) telling Tyler how cool I thought that was and he said “Sure. But I’ve always thought when we hit 1,000, then we have something special”. I then remember 1,000 a few years later.

I remember Charles coming on board full time when we had about 1,600 customers. That day I started to sleep better and have slept great since.

I remember the day I realized I don’t like getting emails from companies I’ve never heard of telling me about their products. It’s not how I buy stuff for our business and I was (stubbornly) certain restaurant owners felt the same. I remember deciding we’d never send another email again.

I remember Wil deciding to join our company and Tyler sending me an email with the subject “Wil!!!!!!!!!!!”. Nothing in the body. That’s the most excited I’ve ever seen Tyler. In fact, when we hit 1,000 customers he didn’t say anything. I figured maybe he changed his number to 2,000.

I remember Hank joining our team and realizing that the 5 of us were back together again – we all used to work together years before. That was cool to see it happen all over again. What are the chances?

I remember a chain of 250 restaurants telling me Schedulefly looked too simple. Within minutes I went from panic to calm.

I remember, later, turning down a few chain restaurant opportunities that would have been good for revenue in the short run, but terrible for our business in the long run.

I remember people telling us they don’t like our software and the very same day other people telling us they love it. I remember the calm that came over me when I finally realized I (we) can’t please everyone. Don’t ever try.

I remember our 1st paying customer inviting me over to demo Schedulefly in person….a mutual friend had introduced us. It was a Mellow Mushroom in Raleigh run by a guy who is now a friend and now uses us at all 4 of his locations. He said after 5 minutes or so – “I like it, let’s do it”. Over the years we’ve added 72 more Mellow Mushrooms via word of mouth only.

I remember our 2nd paying customer – Café Luna in Raleigh – inviting me over to demo the software – in the stock room/office back near the kitchen. I remember them frantically searching for their Ethernet cable so I could plug in my laptop – back in July 2007 when wireless was not everywhere. I showed it to them and the owner said “How much?” I said, “Um, $30 a month?”. He said “Great, set us up”.

I remember after that meeting at Café Luna – our 2nd customer – I never demo’d Schedulefly (in person or on some webinar) to anyone ever again.

I feel fortunate to have a business with so many fun memories and am really proud of what 5 guys have built over the years.

Wes