Taking the Leap to Full-Time Entrepreneur: Matt Rose of ClubUp

Designli clients have built some pretty amazing apps and are running some awesome startups. The clients that get our highest respect, however, are those who make the transition from app as a side hustle to app as their full-time gig. Matthew Rose, CEO of ClubUp, is one of them.

Matt recently left his position with the Schaeffler Group, a manufacturer of products and technologies for the automotive and aerospace industries in South Carolina, only three months after ClubUp hit the App Store in June. ClubUp is an app that allows members at select country clubs around Charlotte, NC, to hire and pay for caddies, giving golfers and bag-hauling kids more flexibility and reliability when it comes to enjoying the game.

As no two startups are ever the same, we wanted to know what went into Matt’s decision to live the #startuplife full time, without a net. For Matt, this bold leap wouldn’t have been possible without the support of his wife, father, brother, mentor, and the entire ClubUp team. Below, we interview our client Matthew Rose on his journey to full-time entrepreneur. 

How was the idea for ClubUp born? Was this something that came up among friends after a round of golf?

Actually, the idea for ClubUp came during a class at my Wake Forest MBA program. I am part of the Saturday program (graduating in December) and the classes are roughly four hours long, so it is often challenging to stay focused on the material 100 percent of the time. Initially, I had thought of an on-demand caddie service for public golf courses but after a couple conversations and some thought, I realized that model would make it difficult to really be able to have ClubUp achieve what I thought it could. We are focused on youth development and also increasing youth participation in the game, working with private golf courses allows ClubUp to do that in a very safe and controlled environment.

How long did you mull over this idea before you took action? We hear all the time from clients that an idea can almost keep them awake at night until they find a way to act on it.

Any real movement on the idea did not really start until the first quarter of 2016. The initial idea for ClubUp came about in the summer of 2015 so there was absolutely a period of my sitting on it. What really pushed it forward was my joining the Wake Venture Capital Team in the fall of 2015. A few key events during that experience helped jumpstart it all.

Are you a big golfer?  Tell us a little about what the sport means to you. 

I love the game of golf and have played casually since middle school. I did play a sport at The University of Louisville, but it was soccer, not golf. Golf is a great sport for a number of reasons but the fact that it allows me to relax and be outside while also providing an opportunity to be competitive is great. I really started to appreciate the game while caddying at a club in the suburbs of Detroit. The job was great for learning golf and also developing skills used off the course that I still need today.

Tell us about The First Tee. What is the relationship between First Tee and ClubUp?

The First Tee is a fantastic national organization that focuses on youth development through the game of golf. ClubUp started with a partnership with the chapter in Charlotte, but we recently have become national partners, which is obviously great for our company. The affiliation adds quite a bit to ClubUp due to the name recognition, but it also is very key for us in terms of the service we provide.

The First Tee has done such a great job developing their kids that many of the more difficult tasks involved with being a caddie are already addressed. It is easy to teach a young person how to give a yardage to a golfer or where to stand on a tee box, but being sure they understand something like taking their hat off in a clubhouse can be far more difficult.

Ike Grainger, who’s now part of the ClubUp team, had been the executive director of The First Tee in Charlotte. The hard work he put in helped make the Charlotte chapter one of the best in the country and they have continued to be great after his departure. We have had a chance to meet many of the people at The First Tee of Greater Charlotte and they are all very impressive, as are the kids involved.

What are some of your goals for ClubUp (besides being a profitable company)?

There are so many things that we want to do with ClubUp as the company matures. I would say that we want to help young people find employment and also develop necessary skills for their successful future. We would like to see more people walking on the golf course and experience how enjoyable the game is with a caddie. From a broader perspective, I feel that technology can help create jobs and even resurrect some forms of employment that over time have become almost obsolete (such as caddying). There are plenty of companies focused on finding a way for technology to eliminate jobs – we want to focus on how technology can help create them.

Did you envision running ClubUp full-time? Was this always your plan?

When first envisioning ClubUp, I never really thought about it becoming a full-time job. As investors started to commit and the golf clubs we approached welcomed our services as a way to improve the golfing experience for their members, it started to enter my mind that we may have something pretty good. ClubUp still has a long way to go before it is profitable company but we have had a nice start and the future looks bright.

The reality is that ClubUp would be nowhere close to where we are right now without the people involved, including Ike Grainger. I did not even know Ike prior to starting ClubUp and his involvement came as a result of my getting support from leadership at Wake Forest. Seeing how a company evolves and all the different things required to make it work has been very educational for me. I am sure there are people out there smart enough to do it without guidance from a mentor or friend but for me it has been essential. I feel confident in saying that you will not find a founder of a company that has been more reliant on support from others than me.

What made you take the leap now?

The decision for me to leave my full-time job and run ClubUp was not made alone. The chairman of the board at ClubUp had a huge part in helping me understand when the time was right. I also have a great friend I have known since I was 6 years old who lives in Charlotte and he has started his own successful company. We communicate almost daily and I use his advice quite a bit. In addition, I discussed it with my father and brother who are both role models for me. When doing something like leaving a comfortable job with a large company to start your own business, you will get all sorts of opinions. I just tried my best to make sure I listened to the people I trust the most and take bits of advice from them all.

In the end, if my wife was not comfortable with my making the move I would have never done it because she and my twin daughters are the most important thing in my life and there is not a close second. Without having a woman like her at home, none of what we have done would be possible. She has supported my working overseas while she stayed in the U.S., our moving five times in nine years and then my starting grad school at Wake Forest while working full time and having infant twins at home. She is amazing and knowing that she was handling things at home made the decision much easier because I knew what mattered most was in good hands. If she did not provide the stability that she does, I would have waited and likely missed this great opportunity.

Had you set any metrics or milestones for when you’d leave your job to run ClubUp full-time? Did you decide you’d make the change once you had a certain number of clubs on board, or a threshold of members using the app? 

Most of the decisions and all of the success at ClubUp are the result of the team we have involved. It is very rare that anything is done without input from everyone on the team. This is important because my lack of startup experience could result in decisions that may negatively impact ClubUp. In addition to the support from those close to me, I left my job to run ClubUp because leaders I trust who have successful backgrounds in startups or company leadership felt the time was right. I do not think it was a certain number of clubs or members using the app but the fact that we knew people were using the service and we knew ClubUp would reach the target of our first capital raise lead to the decision.

What is the reaction you get when you call it ‘Uber for caddies’? Does the phrase ‘Uber for X’ make investors sit up and pay attention? 

The phrase “Uber for caddies” comes up in almost every discussion we have when the company is explained but it is not something we push or market. A recent article on ClubUp called it “Uber for Caddies” in the headline so it became even more associated with ClubUp but it is actually very rare for anyone from ClubUp to say it. We do follow a similar model that Uber does, mainly due to using an app with location services to alert independent contractors of an available work opportunity. However, we are already providing additional services to both the golfers and our partner clubs that go well beyond traditional caddie services.

There is obviously a big focus on the “sharing economy” in business today and many startups are trying to capitalize on it so when people hear “Uber for …” then they listen. The investors we have at ClubUp have all been very successful in business and appreciate the idea of ClubUp for many reasons, including the way we connect caddies to members.

What are the plans for ClubUp’s growth? Where do you see the company next spring, or a year from now?

We are going to be adding another club in the Charlotte area in October, bringing the total to five. ClubUp will be expanding to Winston Salem and Greensboro this fall and we have a few other clubs in additional cities that we are starting to talk to. We do not have any goals set in terms of numbers of cities or clubs because we are still learning so much and changes happen weekly. We will grow as it makes sense to grow but we are focused on providing our existing partner clubs with great service and the caddies with great opportunities.

What have members told you about ClubUp?

We have received great feedback from the members, mainly about the caddies themselves. All of our caddies are trained on the golf course and we have met each of them in person. The members are finding out the same thing that we did when we started ClubUp – The First Tee and the game of golf itself do a remarkable job of helping kids develop.

We have a rating system within the app and it shows us that the people who use a ClubUp caddie truly do enjoy the experience. We have some areas of focus in our training, but this is expected.

What do the caddies say?

The caddies have all been very happy with ClubUp. The flexibility of the job, the money they earn, and the opportunity to play some great private clubs all have the caddies excited. In addition, they are carrying bags for local business leaders who can provide some mentorship and opportunities for the future.

Have you received feedback you were surprised by?

Absolutely. I think if you ask anyone involved with ClubUp that question they would all say that we were very surprised to hear that many of the players have commented on how well the caddies read the greens. We do have some high school and college golfers carrying bags that are very good players but I am referring to feedback on some of the younger caddies at ClubUp. It has been really cool to find out that even our youngest caddies are not only improving the experience for golfers but also helping their game a bit, too.

What would you tell anyone who’s considering building an app?

I would say that no matter how basic your app will be, as soon as you think that you have thought of everything that can go wrong or come up, you have likely thought of about 10 percent of what could go wrong or come up when the app goes live. And I mean that relative to user experience and functionality of the app, not the performance. The app needs constant attention and updates to keep up with the business.

What do you wish you knew before you started this process?

I had this thought in my head that once I left to run ClubUp on a full-time basis, things would slow down and I would have more time to focus on my last couple classes at Wake Forest while at the same time staying on top of everything at home and at my company. That has not really been the case. Things are just so different now and instead of a company telling me what to do and where and when to do it, I need to manage all that on my own, and it’s very difficult to do.

I was overconfident on what it would take to perform at a level that will help ClubUp become great and I could have been more prepared for it all if I would have done a few things different. I’ve said it before, but without the team involved at ClubUp or my amazing wife at home, I would be more of a mess than I already am. I am just very lucky to have the support and guidance from a fantastic mentor and also a father, brother and good friend who makes themselves available to help and listen.