Schedulefly Stories

Growing a software business one restaurant at a time

New podcast: Nick Tedeshi, head brewer at The Post in Boulder, CO

Nick is the head brewer at The Post Brewing Company. His passion for his craft and for his team is palpable, and you’ll enjoy hearing from a non-owner talk about what it’s like to work for a phenomenal owner and a team that is one big ole extended family at Big Red F. I was so fired up after talking to Nick!

You can listen here (, or search “Restaurant Owners Uncorked” on your Apple podcast player.


New podcast episode: “Listen to your 4:00am voice”

Joanne Draganowski owns several restaurants in Wisconsin with her brother and sister. The story started in 1951 when their parents opened their first place, and it continues today with four of the seven children still in the restaurant business. Joanne is very sharp, understands the business in and out, is a frequent mentor to aspiring restaurant owners, and has a clear love and for the restaurant industry. We had a very interesting, thoughtful conversation, and I could have talked to Joanne for hours.

You can listen here (, or search “Restaurant Owners Uncorked on your Apple podcast player.


One of Schedulefly’s role models is my daughter’s second grade teacher…

This is a repost of one of the best stories we’ve told over the years. It’s a great analogy to how we run our business. Wil wrote it more than 6 years ago and at the end of the post he mentioned that we had just welcomed our 2,000th customer. Since that post we’ve added 5,000 more customers and the story is still true…

My daughter just finished 2nd grade. She had an absolutely amazing teacher who has been teaching for 37 years. Mrs. Owen.

As you might imagine, it was a special year because Mrs. Owen is the best at what she does. After all those years, she knows exactly what second graders need. She knows how to teach them. How to manage them. How to love them. If you could create the perfect second grade teacher, it would be Mrs. Owen. Period.

It occurred to me that Schedulefly is similar to Mrs. Owen in several ways, and she is a great role model for us. Like her, we have a laser focus. She focuses on second graders, we focus on independent restaurants. She wants to be the best at teaching second grade, just as we want to be the best at serving indie restaurants.

Also, Mrs. Owen doesn’t try to grow with our students. She doesn’t try to learn to teach third grade, then fourth grade, and so on so that she can follow her students all the way through their growth. She knows she would never be the best at teaching those grades, and that’s not where her heart is. She’d always be trying to catch up, always trying to add to her teaching repertoire, and so on. Rather, she waves goodbye and wishes them well and waits for the next round of second graders to come through. When they do, she welcomes them with a smile. And knows she’s doing exactly what she was meant to do.

Likewise, we don’t try to grow with our customers. Every now and then we have a customer that has grown to the point of needing more complex systems versus a simple scheduling and communication app. They need some feature or integration that we don’t provide, and they grow into solutions from other companies. We don’t try to make our app more complex to try to keep up, and get into things we would have to learn, or that we aren’t the best at. That’s not where out heart is. Rather, we wave goodbye and wish them well and wait for the next new, independent restaurant to open its doors for the first time and sign up for a Schedulefly trial. When they do, we’ll welcome them with a smile. And know we’re doing exactly what we were meant to do.


P.s. Last week we hit a cool milestone of 2,000 customers. We’re so thankful to serve all of you, and can’t thank you enough for your business!

If it’s useful and fast, please don’t change it.

I’ve been using the same online bill paying service for 20 years. It’s bare-bones simple and always has been. In 20 years, it has not changed once. They’ve not added any features and they’ve not changed the user interface. I use it to pay my bills once every month, which is something that unfortunately i’ll have to do forever. The interface is so so simple. It has a list of all my payees – with a way to manage them (+/-) and a place to make a payment to one or more of them. It’s literally a few boxes and a couple of buttons. After I pull together all the bills I need to pay, I log in and enter the payments and then I go about my life. It’s lightening fast (likely due to its simplicity) and it works. Most of my bills are paid electronically right away – and a few receive a check within a few days. Not once in 20 years has a payee not been paid. Not once. So not once has this company let me down or have they changed what is already useful or have they contacted me to sell me something else. It’s reasonably priced and I’d honestly pay twice what they charge me. I love this company. I love everything about what they believe in.

Clearly we’ve always believed the same thing here at Schedulefly and we are occasionally reminded of the real impact this has on the people we serve. Recently I emailed the owner of a very successful restaurant group in Raleigh N.C that we’ve served for 7 years (to thank him for his business) – and he sent the nicest note back and said…“Awesome, thanks Wes. Schedulefly continues to be an amazing, headache-free tool for us, and we literally can’t say that about many other things we use regularly”. I really took that to heart. It’s fuel for the rest of my year, really.

So the moral of this story is: thank goodness there are technology companies around that understand that you don’t have to keep changing your product to stay relevant and useful. Let the competition be the ones that don’t understand that. You’ll end up being the one that they love.


5 guys with 7,000 subscribing customers

This weekend the 5 of us at Schedulefly welcomed our 7,000th paying customer. 5 people serving 7,000 customers with over 300,000 servers, bartenders, hosts, managers etc. is so darn cool and we are so proud of it. And since there are dozens of scheduling software options for restaurants, our pride swells with every new customer we bring on. You see, we don’t “sell” Schedulefly to an organization that mandates its use at all of its locations. We actually don’t sell it to anyone at all. Rather, we position ourselves to be found and to be chosen by the right customers. It’s a slower way to grow a software company- but it’s very manageable for the 5 of us and allows us to be with our kids and families and enjoy what we do. Borrowing someones money and hiring more people in an attempt to grow faster would ruin all of that.

So now we move towards 8,000 – and just like the last 7,000 – it will be done one restaurant at a time. The downside (if you can call it that) is that it will take a bit longer now than it used to – and might even take a few years – but the huge upside to that is…who. freaking. cares! And for that we are so thankful. We are so thankful no one here at Schedulefly expects us to grow faster. We are so thankful no one here worries about what other companies are doing. We are so thankful that no one here thinks we should be serving larger customers or customers in other industries. In our industry (software as a service with a big market to serve), this is rare. We are indeed lucky.

We are all so thankful and so happy to be doing what we do and thanks to all of our 7,000 customers for choosing us.


Independents CAN beat chains, and many of them do.

Scott Maitland is the owner of Top of the Hill Restaurant, Brewery and Distillery in Chapel Hill NC. Scott literally started his business (over 20 years) ago to prevent a chain restaurant from dominating such a cool small college town. He and his team succeeded and still do today. Their mission is to embody and enlarge Chapel Hill’s culture and heritage by providing an independent, unique and enjoyable dining, drinking and social experience. Thank goodness for people like Scott.

Top of the Hill has won dozens of “Best in the Triangle” awards. The Brewery has won scores of gold medals in international competitions and three of its beers – BlueRidge Blueberry Wheat, Rams Head IPA and Singleton Ale – have been recognized as the best example of their styles in the world by the World Beer Championships. Top of the Hill Distillery – makers of TOPO Organic Spirits- is the only all-local and organic grain to glass distillery in the South and we have been making award winning Vodka, Gin, Whiskey and Rum since 2012.

This is a video we made 7 years ago. It’s Scott talking about several topics including the advantage he believes independent restaurants have over chains. It’s so good and it’s so inspiring for any business owner that is setting out to compete against businesses with more money and resources. Enjoy…


Making assumptions. A tale of two restaurant groups.

This is a tale about two very different, yet very popular and successful restaurant groups. They are similar in ways – but what makes them different and unique is not just the food they serve or the atmosphere of their restaurants – but what the people who own and operate and run the restaurants believe in. If you peel back the layers on who these people really are and why they do what they do – you’ll see very different human beings on very different paths. Serving them both well and treating them the way they like to be treated and the way they treat their guests is impossible. This is why we try not to make assumptions at Schedulefly and you’ll never see marketing content that suggests we are going to make life easier or better for anyone and everyone running a restaurant. In fact – if I were a restaurant owner and I was shopping around for a solution for something and bumped across one that assumed my entire industry was going to be changed by what they offer – I’d move on. I’d keep shopping…

So a bit more on the topic of assumptions. Making them and believing they are true feels like gambling. It’s like flipping a coin. I try not to make them – but it can be difficult not to. It’s hard to plan and I guess it’s why we read so many stories about businesses and people that “pivot” and change direction. I think, in general, the more assumptions I make, the better chance I’ll have to pivot. But hey I guess that’s life and it’s why we are all on one big long journey (hopefully) of pivots figuring out what we really want to be…

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10 things we’ve not done in years at Schedulefly

This is a list of things we did not do that I posted at the end of 2015. I stumbled across this list recently and realized all 10 were also true at the end of 2016 and 2017. And all signs point to it being true at the end of 2018. I am re-posting it because we are all so proud of what we’ve done with just 5 people. And we’ve been 5 since 2012….so we have not hired anyone in almost 6 years. That is what I personally am most proud of. So the example we are setting is not on how to create a business that creates jobs, but rather how to create a business that can’t afford to ever become complicated – ultimately resulting in one that is a pleasure to own and to do business with. And it’s a business that will never become something we wish were different.

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Restaurant Owner podcast…

We recently hosted our 50th episode of the Restaurant Owners Uncorked podcast, and we’re going to keep cranking out episodes even more frequently. We’re so thrilled to have the opportunity to serve thousands of independent restaurant owners, and we want to tell as many of their stories as possible.

If you are interested in starting a restaurant, own a restaurant and want to learn from your peers, or simply enjoy hearing the stories of people who’ve poured their hearts, passion, time, money, energy and love into their dreams of building successful restaurants, you’ll enjoy this podcast.

You can subscribe in iTunes here

The Schedulefly Crew

Less technology, more service

When I reflect on Schedulefly and what has made us and our industry successful in the past and where I see it going in the future – one simple phrase comes to mind…

Less technology, more service.

Since we do not sell to chains that are slowly removing human service and adding more technology to stay consistent, I am 1000% confident that the restaurants we serve will always need reliable human beings to be successful. And I also think that they will see out companies that offer simple solutions to their problems backed by service from warm, approachable human beings. Unlike a self-checkout at the grocery store that we currently use or a futuristic drive-thru only McDonalds that’s run on 100% software and machines – great independent restaurants that sell more than just food – will always need nice, helpful humans to help with solve their problems.

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