Schedulefly Stories

Growing a software business one restaurant at a time

Month: August 2016

Staying the course

Occasionally I look back at old blog posts of ours and just nod my head. It feels good to have stayed the course and resisted the urge to add more and do more and hire more for fear that we would not keep growing. I honestly believe that most company founders and owners would have loved for their business to stay small and fun and manageable with just a handful of people. The problem (I’d guess) is they lost sight of why they started their business due to investors and partners and more people and overhead forcing them out of their sweet spot and into an entirely different kind of business. Hopefully they still enjoy it, but I’d bet the reason they started the business is lost in a sea of new products and services.

Below is a post from a few years about the original reasons why I wrote Schedulefly. Thought I’d share it again. It’s still true.

While in college, I was a waiter at a nice full-service independent restaurant in Wrightsville Beach NC. There were 2 owners – one of which was there every night. During the summer they were both there on the busy nights. At that time, it was one of the best independently owned restaurants in the area and it was run very well. Eventually I became one of the more senior staff (thanks to my extended stay while taking my sweet time getting an undergraduate degree) and made the schedule for the wait staff. Before I was senior enough to call the shots on when I wanted to work and also make the schedule for the others – I (and every other waiter – about 40 of us) would do one of the following every week to find out when we worked:

a) Call the restaurant and bother whomever answered the phone and ask them to run back in the kitchen (where the paper schedule was posted) and check it to see when we worked. This was officially banned by the owners – but sometimes it was still the only option – short of option c below – which was miserable.

b) Call the person who made the schedule once we knew it was done. Of course in the mid 90’s no one had cell phones so calling meant calling them at home. College kids are never at home.

c) Get in our cars and drive to the restaurant to go personally check our schedule. This was most common. Seriously.

And that was just Sunday – the day it was posted. The rest of the week got worse once it started changing.

It was a simple problem our restaurant had back then and when I sat down to write the first lines of code for Schedulefly about 10 years ago – it was those 3 things that I thought about. I thought about what those two owners (and the staff they employed) would need to help with that. That’s it. I did not picture this software being used one day by other businesses with these same challenges and integrating with other products and other companies and becoming giant. I did not think that I would spin off a Schedulefly for retail and Schedulefly for healthcare and Schedulefly for [insert you favorite industry here]. Today, I still don’t.

Because today and in the future, thousands and thousands of great independent restaurants (just like the one where I worked) still have that same simple problem as we had back then. It’s a simple problem that needs a simple solution – and the problem will never go away. Sure, with technology, we could add tons of other stuff in an attempt to solves tons of other problems in hopes of growing bigger and faster and serving more customers – but we would miss the entire point. In fact, the point of it would be lost in a sea of options and features and complication. I know for sure that those two owners who I worked for wouldn’t like it and I wouldn’t blame them.


Rayme Rossello, member of the Schedulefly community, and the story of Comida

Here’s part of our interview with Rayme. You can listen to the whole interview on our Restaurant Owners Uncorked podcast series on iTunes.

How did you get started in the restaurant business?
I started Proto’s Pizza with my partner at the time, Pam Proto. We opened five Proto’s Pizzerias together. We started with one in Longmont, CO in 1999 and opened four along the Front Range and one up in Boise, Idaho, just to try our hand out-of-state. We did that in seven years. And then I sold my half to her in 2007. After I left she opened one more and they’re still going strong.

Opening five locations in seven years sounds like it was a pretty busy time.
It was pretty busy for sure. We were just scared to death for the first little bit. I think each time we opened a new location, I would just wonder how in the heck we were going to get it all done and where was the money going to come from and how to make it all happen.

But Pam is very tenacious and I learned so much from her over the years about putting your right foot forward and showing up and working hard. We hired really great people because obviously you can’t run five restaurants alone, especially with one in an out-of-state area. It was a great opportunity. We worked really well together for that whole time.

What made you decide to branch out?
I love pizza and I love Proto’s and I still eat it about once a week, but I just was sort of antsy to do my own thing.

I put myself through pastry school just before she bought me out, just to learn a part of the restaurant world that I was completely unfamiliar with and also very uncomfortable with. I didn’t want to go through sixty thousand dollars’ worth of chef’s school, but I wanted to learn a little of the back-of-the-house side of things. So I did the pastry thing and that was a great eye-opener for me just in terms of knowing that I never wanted to be a pastry chef. But, I still love making pastries. I just made fresh peach ice cream this morning here at home before I went to work. I love the pastry side of things from a home perspective, but not from a real world restaurant perspective.

After that I actually bought into a small restaurant in Boulder and co-owned that for a year with someone. That restaurant is still there, but it just wasn’t the right fit for me. It was an incredible learning experience on many levels, but it wasn’t my lifelong “oh-this-is-going-to-be-a-great-business-partnership.” It wasn’t exactly what I wanted to do. After a year I worked on sort of dissolving that partnership and relationship from a business perspective.

That lead to your food truck, right?
Yes. I was ready to really do something at that point just one hundred percent on my own. I didn’t have a ton of money left in terms of some extra cash in the bank to start a whole new business. I thought about what I could do on a smaller budget with a little bit less commitment perhaps than a restaurant. The food truck thing had just really started coming around. This was 2009. And in 2010 I eventually started it.

Well, it turned out food trucks weren’t legal in Boulder at the time. I didn’t know that. I didn’t know only because there were none. It seemed like such a great idea to me. It didn’t even cross my mind that they wouldn’t be legal. I knew of somebody else that had tried to start one but it ended up not happening and I didn’t know why it had failed.

I put down sixty grand on a truck in East Brunswick, NJ, was having it built out, having it shipped out on a flatbed to get to me here in Boulder. I was going through that process in trying to get city licenses and that’s when I learned they were not legal, after having spent all of that money. I don’t always do things in the right order (laughs). It was going to be really difficult to make it happen. Five-and-a-half years later and it’s more than happening, which took a lot of hard work, especially in that first year-and-a-half.

We were trying to figure out how to not get arrested, and where can we go make money without being tracked down. Where can we go without somebody calling the cops, because I was making them mad for parking somewhere on the street, even if it was a long distance away from the front door of their restaurants? So I didn’t do that very much. I figured out another way to make money and pay the bills and when the opportunity presented itself to open a restaurant – that’s when I thought this may really work. After just a year-and-a-half of running the food truck, I realized that was a hard way to make a living. The hardest, actually.

I read an article where you said that every time you’ve ever second-guessed yourself it’s been done out of fear, but when you jump in with both feet and do something anyway the doors kind of opened for you. How have you learned to embrace fear?
Fear is a natural part of life. It’s easy to look on any number of different blogs where they talk about restaurant openings and closings within the last month, and you see how many, with very good intentions and sometimes great ideas, start and within a year they’re closed. With Proto’s, when we opened our doors at that first location, we had, I think, two thousand dollars in the bank account on the day that we opened. There was no room for error. There was no room at all. We had signed a lease for a long period of time, and then there we were, two of us about to make a living from one pizzeria and two thousand dollars in the bank. I think we were very lucky. Often people have the best intentions and the worst ideas.

I was actually thinking about our concept last night. People open small little sort of street side cafes but they have six tables and a small menu and they think, “I can do this. I can make this work.” That’s a lot like opening a food truck. You’re thinking to yourself that it’s a small commitment. But the bottom line is unless you show up every single day and make it work and make the food delicious and serve it in a way that makes people want to come back, they’re not going to. If you only have six tables, or you just have a food truck, and a two-hour window of time during the day to feed people, if you screw that up, what do you do? With the food truck there were times when we would spend three hours prepping in the morning. We’d go out and it would be a bomb — we’d sell seventy dollars. With me and two other people on the truck, seventy dollars doesn’t even pay for gas, let alone all of the other things.

The fear is real. And you have to manage it and also manage all of the moving parts that make up service in the service industry in regards to restaurants. It’s a lot. And a lot of people don’t know what they’re doing. A lot of times it’s naiveté. They think it looks really fun. But the bottom line is, in the middle of the night when you wake up at two-thirty in the morning, you bolt up out of bed because you think to yourself, Holy crap, it’s payroll taxes, it’s Wednesday tomorrow. And there’s not enough money in the bank account.

Have you changed your management style over the years?
Absolutely. I’ve had experiences with people that are total hotheads and that’s clear to me that that’s no way to manage or lead. Nobody likes it when people blow up at them. Leading by instilling fear in people is a great way to make people not want to stick around. And then the opposite side of that is just being completely dispassionate and not available for people, not listening. Not watching from the extreme end of market trends to just the minutiae of what’s actually happening in the dish pit today. It’s a broad spectrum of stuff to pay attention to and there’s only twenty-four hours in a day and some of those you have to sleep and also have a life.

This has been one of the key things for me. I’m not an hour-counter. I don’t talk to people about how much I work. I don’t calculate that stuff in my head unless it’s been too long since I’ve had a day off. But in general, I feel like a good manager-owner. I have to have time for myself. It’s how I regroup and show up ready to be in charge again, be the boss. Nobody wants a boss that’s just downtrodden and tired and like a martyr. That’s just a bummer to me. I wouldn’t want a boss like that and I don’t want anybody on my management team to be that way.

One of the questions that I ask people when I hire them, especially when they’re going to be in leadership positions, is what do you like to do when you’re not at work? What’s important to you? Do they hike? Do they just go out to the bars all night long? Are they the kind of people that love to go out and eat and enjoy the dining experience? What do they do? Do they like to read? Do they read cookbooks? Are they informed? What makes them tick? Interesting people make for interesting managers. And boring people get bored, I guess (laughs).

You got the truck in 2010, opened one location in 2012 and a second in 2013. That’s intense!
It was a lot. The second restaurant, that whole opening was a crazy month’s period of time. I had sold my house in order to get money to go towards the opening of the new restaurant and just timing all of that and getting a loan and the SBA, the bank and all of that stuff. Thank God I have an amazing bookkeeper who works for me pretty much full time and she has really neat handwriting and is a great bean-counter. Those are the little things and sometimes my time is better spent doing other things.

Two weeks after opening the first Comida location I moved into a new house. The day I moved in was the day the 100 year flood came to Boulder. It was INSANE! I grew up wanting to be an actress and wanting to be in the theater and there was always that thing – the show must go on – and that’s the same thing that happens in my industry now. You still open your doors. You still show up and make food and serve it.

Are you going to keep expanding?
Yeah! Just yesterday I brought home a Sprinter cargo van. I’m growing the indoor catering piece to my business, which is really exciting. And I’m also about a week away, maybe not even that much, from signing a lease on a new location in Aurora in a building called The Stanley Marketplace. That’s another incredible opportunity. It’ll be the third Comida Cantina. I’m proud of the brand, I’m proud of the food. It’s all made from scratch. It’s not brain surgery. It just takes showing up and doing. And so I’m excited to do it again. I think it’ll be great.

Just showing up and doing…
I think a lot of people might look at it as sort of plodding. “Ugh! I’ve got to get up again and do the same thing over again.” But I am one hundred percent a morning person. I don’t know how people do it without being a morning person, although my restaurants don’t stay open until midnight or one o’clock, so maybe that’s part of it.

I’m excited every day that I wake up and there are new challenges. And sometimes they hit you in the face like a ton of bricks. Three weeks ago one of my very dearest, sweetest employees – she was just everything, longest tenure at Comida — very unexpectedly let me know that she needed to move on. She needed to take a job that was closer to where she lives, closer to her husband and family. It was a really hard decision for her, and it completely blindsided me. There are moments like that where you think, Holy you-know-what — how do I do this without her? What do I do? What’s the next day going to be like? Who will fill her position? But I know myself well enough to know that freaking out helps nothing. So, if I’m going to freak out I do it by myself in my car – which I did.

Then, after a good night’s sleep and a bunch of just writing stuff down, different ideas, I woke up in the morning with a clear head and some ideas and had a good conversation with her, and I was okay. Within hours this amazing person who I’ve worked in a different sense – she’s done all my graphics stuff for the last fifteen years (even since Proto’s) — stepped up and said, “I’m really interested in talking to you about that position.” I couldn’t be luckier to have her.

If it were easy then everybody would do it. That’s one of my favorite things to say because it’s true. It’s just not easy. But there was the solution. I think so many people sit and spin in the problem and they show up and they talk about the problem. I had a really great boss at one point (my favorite boss, ever, really the only boss I ever had*) who said, “Rayme, if you show up to work consistently and you’re thinking to yourself, I can’t stand that person, why are they doing that? The only person you have to blame is yourself. You’re Rayme Rossello: In charge. This is your world, your reality.”

Parting thoughts?
You can either make it great or it can just suck and you can plod through it every day and that’s not how I want to live or run restaurants.

* Rayme’s boss was Dave Query of Big Red F Restaurant Group in Boulder, CO. Dave is featured in the first Restaurant Owners Uncorked book.

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.


Jess Killeen, a member of the Schedulefly community, shares the story of Grassburger

Jess Killeen and her husband Ed own Grassburger, with locations in Durango, CO, and Albuquerque, NM. What started as a transition to grass fed beef for their family of five led to an idea for restaurant. When the couple sat down to write their business plan, neither of them had restaurant experience. Four years later, they now have two successful locations. This is an inspiring story about a family that didn’t let lack of experience stop them from creating something special in the two communities they serve.

All of our Restaurant Owners Uncorked podcast episodes are available here on iTunes.

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