Back in 2007 Tyler and I had a short meeting (in my old office – at another company where we worked together) that lasted about 15 minutes. He was leaving and we decided to make Schedulefly a real business and we talked about how to get started. Schedulefly was something I had written back in 2005-ish and had no idea how to make it a business. It was about as simple of a meeting as I had ever had in my life. Other than incorporating it, there were 2 main goals…or baby steps I guess.

Step 1 was to get the server (actually just a PC where Schedulefly was currently running) out of a closet at my house and move it to a real web hosting company. I had 2 restaurants using Schedulefly- both were owned by friends who would treat me to a round of golf or a pizza in trade for using it. Our new server at a real host was going to be $400 a month. Since we currently had zero revenue – I remember telling Tyler that surely he and I could go get 10, full service independent, restaurants to pay us $40 a month. 10 customers. Ten. If we can’t do that – then we should just unplug the Schedulefly server forever. Tyler would tell me a few years later that in his mind (during that first meeting) 1,000 restaurants meant we had something special. So I thought 10 and he thought 1000. I am glad he is a patient guy.

Step 2 was to pitch it to some restaurants. Neither of us were sales guys so we emailed mostly. We got people to check it out and a few signed up – and many told us how terrible it was and that we had no idea how a restaurant schedules staff. Since I had actually written a schedule for 40 (20-something) waiters – and would have cut off my arm for what we were offering – I felt differently. But still, I knew we were about 50% where we needed to be in features to appeal to a lot of restaurants – so we started added stuff like betting alerting, better labor cost reporting, time off requests etc. Actually, now that I think about it – it was a ton of stuff….but it was necessary core stuff – not bells and whistles. The system stayed simple. Tyler somehow got us that 10.

Well for the rest of 2007 (about 6 months) Tyler muscled his way through it (I was still working for another business) and brought on about 60 customers or so. That fall Wil joined us and we were on our way to 100. By the following summer (with the help of a lucky timing front page article in NRN) – we had brought on 100+ customers. I remember that day because I was on vacation with my wife’s family and my brother-in-law and I toasted the milestone. So in a year we brought on 100 customers – that felt pretty cool.

So I’ll skip the next 5 years because there were never any significant moments where we brought on a giant number of customers – and for many reasons – we are thankful for that. We have literally added customers one a time and tweaked the software as needed – taking baby steps the whole way. I do remember hitting 500 and 1,000 was huge too. 1,000 customers meant Tyler thought we had something valuable. That was sweet! I remember 2,000 too….about a year ago.

Today I changed our website to “Over 3,000 restaurants use Schedulefly”. Unreal. I remember 10 being my goal. Ten! Now there are 5 of us working on this business – 5 people who spend quality time every day with their families. 5 people who don’t work together in an office and who rarely travel (actually Wil is the only one who travels when filming customers) and don’t work with partners and are not pressured by a commission based sales team to add more features in order to meet quarterly goals. I am so proud of that and I am writing about it because 99% of what I read in the media about how companies get started and acquire customers is very different. It’s usually done by spending lots of other people’s money and hiring etc. If you created a business plan based on how we’ve done it so far – you’d probably fail business school – which is funny because if it were not for the UNCW business school having a computer focused area of study – I would have. Now, looking back 6 years, I really can’t imagine getting to this point any other way.

Wes

If you liked this post, you might like Blaze Your Own Path – which I wrote back in 2010.