Software Sales Tips by Matt Wolach

Scale Your SaaS

How to Get Your Startup Early Traction – with Graham Curry


Launching a software startup is like embarking on a journey into the unknown, with twists and turns that can often be as exhilarating as they are daunting. Graham Curry, founder of Handicaddie, shares his insights from the rollercoaster ride of startup life, offering valuable lessons for fellow founders and aspiring entrepreneurs with host and B2B SaaS Sales Coach Matt Wolach in this week’s Scale Your SaaS episode.


Podcast: Scale Your SaaS with Matt Wolach

Episode: Episode No. 314, “How to Get Your Startup Early Traction – with Graham Curry”

Guest: Graham Curry, Founder of Handicaddie

Host: Matt Wolach, a B2B SaaS Sales Coach, Entrepreneur, and Investor

Sponsored by: Leadfeeder


Weathering the Seasonal Storms

Navigating the golf industry’s seasonal nature presented its own set of challenges. With the bulk of golfing activity concentrated in the warmer months, generating consistent revenue year-round seemed daunting. However, Graham and his team devised innovative solutions, such as offering upfront payment discounts, to offset seasonal fluctuations and ensure steady cash flow.

The Power of Persistence

Through it all, one lesson stands out: persistence is key. Graham emphasizes that success in the SaaS startup world is more than just explosive growth or immediate profitability. Instead, it’s about staying the course, learning from setbacks, and continuously refining your approach. Every challenge is an opportunity for growth, and every step forward, no matter how small, is a victory.

Embracing the Journey

As Graham reflects on his startup journey, he offers a refreshing perspective on success. It’s not just about achieving lofty milestones or hitting financial targets; it’s about embracing the process and deriving fulfillment from pursuing a passion. Whether the venture flourishes or faces setbacks, the lessons learned along the way are invaluable, shaping the business and the individual behind it.


The Journey Begins: Identifying the Problem

For Graham, the journey began with a simple realization: startups often stem from personal pain points. In his case, it was the intersection of his passion for golf and the inefficiencies he observed in the caddying industry. This realization sparked the idea for Handicaddie, a platform to streamline caddie scheduling for golf clubs.

From Idea to Execution: The Early Hurdles

Turning an idea into reality is no small feat. Graham faced the initial challenge of building the product with limited technical expertise. However, he persisted, leveraging wireframing tools and seeking the right partners. His tenacity paid off when he found a co-founder, Jimmy, whose complementary skills propelled the project forward.

Conclusion: The Path Forward

Graham’s story is a beacon of inspiration for fellow software leaders embarking on their own startup journey. From humble beginnings to navigating the peaks and valleys of growth, his journey underscores the importance of resilience, resourcefulness, and unwavering commitment. As the Handicaddie team continues to chart their course, they do so with a steadfast belief in the power of perseverance and the limitless potential of their vision.


Graham Curry

[07:11] “Success isn’t just about achieving lofty milestones or hitting financial targets; it’s about embracing the process and deriving fulfillment from the pursuit of a passion.”

[10:52] “Every challenge is an opportunity for growth, and every step forward, no matter how small, is a victory in itself.”

[22:52] “Persistence is so important. If you don’t give up, you either die trying or you find the solution.”

Matt Wolach

[20:02] “Pricing can make or break a company; it’s essential to approach it with a strategic mindset and a deep understanding of customer needs.”


To learn more about Handicaddie, visit: 

You can also find Graham Curry on LinkedIn:

For more about how Matt Wolach helps software companies achieve maximum growth, visit

Head over to and sign up for a 14-day (no strings attached) free trial: 


Check out the whole transcript of the episode here:

Matt Wolach  00:05

And welcome to Scale Your SaaS. Thank you very much for being here. I am delighted to have you join us because what we’re here to do is help you grow your software company, whether it’s generate a lot of new leads, know how to close those leads, and scale your team so that you can have other people doing it for you. We’re gonna help scale your SaaS and each week I bring in an awesome guest who’s either a SaaS founder or somebody helping SaaS founders, so they can share their experience and their knowledge with you so that you can grow. If you want those things, hit subscribe right now that way you’re subscribed to the show, you’ll get all the updates and notifications when we bring in awesome guests, and amazing people and put them in front of you. And one of those amazing people happens to be also one of my clients, the amazing Graham Curry. Graham, welcome.

Graham Curry  00:52

Hi, everyone. Great to be here. Matt pleasure to come on your show, I guess following being on your coaching program. So yeah, looking forward to dive in and hopefully share some of the learnings that you have kindly shared to me during the program

Matt Wolach  01:07

fantastic. And I’ve really have had a good time working with you. And just seeing how quickly you can take things and implement them and grow. It’s been a lot of fun. But I want to make sure everybody knows who you are Graham. So let me introduce you a little bit. So Graham, he is the founder of Handicaddie. This is a software that dramatically reduces the administrative burden for caddy scheduling at Top Golf clubs around the world. As a big time golfer as soon as I met Graham and I knew this was his product. I was like so entrenched in the idea of working with him because it’s such a cool idea. He did this he learned this from being a caddy and a caddy master himself for the last 10 years in Irish and Scottish golf courses, including kingsbarns Golf Links, and Castle Rock golf club, gram has identified an exciting opportunity to provide a digital solution to help staff streamline how their caddy program is run. So it’s really cool what he’s been able to do. And by the way, I’ve seen some of his conversations in his demos and such these people love this thing. He’s done a great job of taking this idea, creating the product, and getting people around the world to start using this thing. He’s also the host of the Future of Golf podcast. So definitely check that out The Future of Golf podcast, a lot of cool stuff. But Graham, thanks for being on the show.

Graham Curry  02:24

Yeah, I think you’ve sold me a lot better than I would sell myself, Matt. So you’ve definitely teed up the intro, and obviously, yeah, being a fellow golfer as well. I think that was one of the things that definitely appealed to me and working with you that you’re you’re in the golf industry. And we could kind of riff on those things as well. I know you’re talking about playing a few courses that we’re hopefully going to work with next year as well. So hopefully, I can actually directly help you out as well, which would be cool.

Matt Wolach  02:51

Yeah, it’d be amazing for my name to pop up in your program under your caddy scheduling and all that. That’d be, that’d be a lot of fun. But tell me what’s been what’s been going on with you lately? And what do you have coming up?

Graham Curry  03:02

Yeah, well, this is our busy time of the year, right now, Matt. Because the golf season, as you well know, is a finite period in many parts of the world. So typically, you’re talking from April to October is the real hot season for golf, especially for fairweather golfers, like myself, who typically go and that shirts like this, and shorts. So right now, because we’ve had a good period of winter where our sales has really progressed, thanks for your help. And really formalizing the sales process. We’re now actually facing the opposite problem of we’ve got a ton of onboarding to do. And now our focus is actually fulfilling those customer requests, dealing with things of people actually coming on, and like little teething onboarding problems. But I think we’re actually so grateful to have those problems, because it was very much the opposite last year, and that it was just purely outreach focused, obviously, a lot less demand than what we have now. But I actually put a post on LinkedIn about this the other day, I feel like we’re transitioning out of the period where it’s just outreach, and it’s almost using brute force to get your first 10 customers, I feel like we’ve passed that now. And now I’m really in the period of, you know, identifying our ideal customer profile and just being like, super focused for that specific group, and really focusing on you know, what features we need to build out to just give them the best experience on our product. So yeah, from a very high level all is always moving right now and going in the right direction.

Matt Wolach  04:35

So fun, such an energizing and fun time when you’re building a software program that you’ve gotten past that kind of initial hurdle of We just put a lot of work in is Is anybody actually going to give us money for this thing? You’re past that you’ve got some good clients, you’ve been able to generate some great interest. So, you know, like you said, it’s a fortunate problem to have they say once you’ve reached a new level, you have a new devil. There’s another problem that we need to overcome. And you’re right, initially, it’s holy cow, we need leads, we need somebody actually come see this thing. And then it’s like, okay, we’ve got business, how do we onboard all these people? How do we make it happen? And it’s kind of crazy how your mind has to shift a little bit, right?

Graham Curry  05:13

Yeah. And it’s also the different emotional test that that puts you through. So, initially, my challenge was obviously, just the actual output that you have to do. So it’s just, can you sit on a chair and write out 50 emails or do 50 cold calls? And now it’s like, it still is that to a degree, of course, like volume of output, there has to be a certain discipline to that, but it’s also, you know, it’s more strategic now, in terms of, okay, we’ve got a club that says they want to use it. But is this actually a club we want to take on based on the constraints that we’ve identified in our ICP? And obviously me being in sales, I’m like, hell yeah, it’s another five or 10k annual recurring revenue. And I mean, it takes a lot of discipline for me to say, perhaps it might not be. I’m like, I’m not perfect at that. I’m still getting better at that for sure. But my software team keeps me disciplined in that as well, whenever their product requests keep going up and up and up. So yeah, trying to get better that every day.

Matt Wolach  06:17

Yeah, I mean, knowing your ICP and making sure you stick to your ICP is really critical for anybody out there wondering what we’re talking about ICP, that’s ideal customer profile, your perfect customer, somebody who fits exactly who’s going to get a lot of value out of using your product and somebody you want to work with and sell to. So that’s what we’re talking about. And it’s critical. It’s like one of the first things we need to do. But you’re right Graham, sticking to it, and actually making sure that you only sell to those people can be a challenge. But I actually want to take us way back. Now I know you’re in this growth mindset. You’re doing great with it. But how did Handicaddie get started? Where did this whole thing come from?

Graham Curry  06:53

Yeah, Wow. So I mean, I started playing golf when I was 13. And it was actually it was strange, because no one in my family actually plays golf. And it was actually one of my friends. I remember the day so vividly. We’re all playing football or soccer as it would be called in America. And so we were just going about our business and one of our friends had played golf for the last six months and said, Do you want to try it? And we were actually quite reluctant to start off we were like, nah, that’s for like old people. And and then we said, Fine, we’ll go along. So think we went to the driving range was like a few rusty three irons, like one of the bladed like butter knife three irons that you get back in the 70s from like a garage sale or something. And obviously, like hit terrible shot, terrible shot. And I think I had one that was like reasonable that went 100 yards, and that like sensation that goes through your hands of just pure pleasure. I was like, Oh, damn, I think I actually want to do this for a little bit. So then that started my journey of becoming a member at a golf club. So I played at a course called Castle Rock, which is one of the probably one of the premier venues in Ireland and situated beside an Open Championship venue called Royal Portrush, which is where Shane Lowrey won his open for any golfers out there. And then because I played at a golf club, when you’re a young member of a golf club, there typically is opportunities to caddy and to work for visitors. So in Ireland, it was actually taken care of a lot of Americans that are on their holidays, and they’re they’re on a tour. Maybe they’re doing like a whiskey tour of Ireland, and they’ve fitted in a bit of golf or perhaps vice versa. And then that gave me the experience of the Caddying industry. So that was a phenomenal job because it combined my passion, you know, I was on a golf course, I was really happy. And also give me great insight into your people skills, like you actually have to entertain. As a 14 year old, you have to entertain what might be this really wealthy businessman for five hours on a golf course. How does your conversational skills stack up to that? And you know, you’re like, as a 14 year old, your small talk skills are next to zero. So I had to learn very fast and become genuinely interested in the person. And usually, you know, walking down the first fairway, you can gauge what kind of person that is like, Is it someone that, you know, is a bit introverted and just wants to speak to his grip? Or is it someone that’s here to drink 10 beers and have a laugh, and then you kind of go along with that. So that was obviously a learning phase. And I learned how the caddying industry operated through that next five years.

Matt Wolach  09:31

Can I pause you right there? Because that’s really interesting what you just said. So that process when you’re 14 of learning how to small talk, learning how to identify people and understand what type of person they were really quickly, are those skills that you still use today in your sales?

Graham Curry  09:48

I would hope so. Yeah. I think one thing that I learned from that definitely that I can apply was just empathy, like understanding what a customer wants out of a service and like, I guess it kind of goes back to the discovery side of it. Like, I guess that was like a micro version of discovery. I remember asking them down the fairway, like, “What are you hoping to get out of this round?”, perhaps in a less formal way than not, but they would either say, I’m just here for like, bit of fun and like, you know, like, just have fun with my buddies, or I’m here to try and break the course record on I need every specific line. So then based on their needs, then you tailor your service to that. So that’s a great point. Actually, I’ve never considered it that way.

Matt Wolach  10:33

Yeah I mean, it sounds like it. I know. You’re very good at that now. So obviously, you had to cut your teeth and learn all that somewhere. That’s really cool  that that’s where it happened. Okay, so I stopped you in your journey. Go ahead and continue.

Graham Curry  10:46

So obviously, at 19 years old, I was I was still caddying. I was at University that time. So I again, I had no idea what I wanted to do at University. So I just picked business management, I thought, it’s not going to rule me out of any career path. So I think it’s a general degree, I’ll go with that. And it was a actually like a train journey coming down from Belfast to my home place in the north of Ireland. And I was going to like entrepreneurial events, and I didn’t have an idea for a business at the time. And I think I knew at that point that I was interested in startups, but I just didn’t have that moment of inspiration. And I remember I listened to a talk and I can’t remember who it was. But they they mentioned that typically, startup ideas come from problems that you experienced in your day to day life. So I remember in that train journey, I kind of took a bit of an audit of my life and identified where the problems were occurring. And then where my passion was. And there was just this massively obvious gap in golf where I was like, this is something I’m really frustrated about in terms of, I don’t have any guarantee on jobs I’m getting, I know that the process is painful for golf clubs, because they have a list of 100 Guys, and they’re making four hours of phone calls every day. And then I actually did a placement whenever I was in school, when I was like 17, I worked in a pro shop for a while in a golf club. And I really enjoyed that process. And I thought, if I can combine golf on business, at some point in my life, I thought that would be great. So to have that idea, early on, I think was a real blessing, as obviously it allowed me to pursue that for the next couple of years.

Matt Wolach  12:28

I love it. That’s so so cool. It’s just such a fun story. And I can tell that it’s just such a big part of you and who you are. And when you can create a company and a platform coming out of something that you’ve experienced, it just means that much more. It’s just so cool. So well done on that I want to understand. So you got it launched. How were those early days, like, Okay, we built this thing now what, like, what happened? How’d you get through that?

Graham Curry  12:54

Yeah, well, the building phase was a really interesting one and getting our first few customers. So I actually, I’m not the technical side of this, I’m very much the sales side of it. So you know, I had an idea for a product, I’d wireframe that out. So for anyone that doesn’t know what that is, there’s wireframing tools like figma or Adobe XD, that’s taking it from like a paper sketch to what looks like an app, but actually isn’t an app. And we showed a golf club in Ireland, and they really liked it. And they said, great, our season starts in 10 weeks. If you can build that out for us, then we’ll use it. And I gathered some funding from from different sources. And I just sat there going like, how am I going to build this thing in 10 weeks, and just out of complete luck. I don’t know how this happened. But about two days later, a guy direct messaged me on LinkedIn After I reached and said, I’m looking for a software engineer for this project. So this guy was working with this club currently, and he ran their Shopify store for their members. So obviously, this was during the pandemic. So they were selling all their merchandise online. So he ran the Shopify store for them and had a great relationship with that club already. And fact, such a great relationship that the guy working in the pro shop was the best man at his wedding. Friends originally, it turns out, so this guy, Jimmy, who’s my co founder if he’s bothering to watch this, his mother, and my mother were very friendly. Growing up. He actually went to my school, and he played at my home golf club, and I’d never met him in my life. So it was just this crazy scenario. And then we said, we got to book a round of golf and actually figure this out. So we played our home course Castle Rock and in the end of the ride, we said, okay, let’s let’s do this. Let’s actually give this a go. So 10 weeks of getting our head down and building a very sketchy, minimum viable product, and then get into the hands of the users. And then once our Glasgow club who was our first customer. After them, we got four pretty quickly just from their referrals from their experience. And obviously, our product was super simple at that stage. So we thought, you know, we know what this could potentially be. And this is a super scrappy version of it. So then I think that gives us the motivation to say, you know, let’s, let’s really pursue this as a career and try and get the next next 10 customers on, you know,

Matt Wolach  15:23

so cool. I love the story to it, having a strong partner is a big deal, isn’t it?

Graham Curry  15:29

Right, like, you know, I worked in this for probably about a year and a half on my own. And honestly, I was 19. So I didn’t really know what I was doing. And it was more of research gathering. I did a bit of a road trip around Ireland, where I actually drove up to the clubs and like, cold approached them and just asked them about the problem. It was nice just to play golf everywhere, to be honest. But yeah, like having someone especially with a software and a really logical head on their shoulders to come back to with issues. And also it’s, you know, yourself, it’s like the emotional supportive of going through this as well like someone to be there for you, you know, 90% of it is going to be those tough times when you’re really figuring it out. But then it also makes it sweeter when you do get a big deal that you have someone to go back and say, Hey, today’s went really well, you know, so it’s an extra journey. Double fun.

Matt Wolach  16:24

Yeah, no doubt. And it’s so cool, because I know you’re just telling your story. But there are so many lessons we can get out of this story. First of all, you have to meet your customers, you have to learn from your customers, what are they hearing? What is their feeling? What are they going through? What keeps them up at night? What are their goals, and you went out and did that you went out and drove to them. Of course, you had the excuse to play golf, but you went and met your customers and started having these conversations with your perfect ideal fit customers. You also have to have great partners, you had a great partner on board, you have to be able to share with others what you do, you were posting on LinkedIn, and you just found your partner that way. And others I’m sure have also come to you that way. But there’s so many things that I teach that you did naturally, which is fantastic. But I’m glad you’re sharing it because a lot of people out there listening might not have done this naturally. But sometimes we fall into great ideas. I’m not saying that you didn’t know anything you were doing. But sometimes you just do things and it happens to work great. And looking back, you can see how big of an effect that that was. And it’s so cool about some of these awesome decisions that you made that helped you get to where you are now. And I don’t know if you can see that the way I see it.

Graham Curry  17:39

Yeah. Right. And I mean, I look back and I look at the first year and a half, and it was very much doing things instinctually based on what I felt was right. Like I wasn’t engrossed in the entrepreneurship space, my knowledge was very limited. So it was just instinctively reacting to like human behavior in terms of like supply demand, like like, why would this person want to use this product? And then kind of fundamentally reverse engineering that to what I need to do then. But I mean, if I knew it, I mean, obviously, you can say this, in hindsight, but I wish do I wish I could go back, maybe not. But there’s obviously things I could have done that would have sped up the process significantly. And obviously, there was a pandemic in between that where Golf was completely shut. So there was no real possibility of getting users. But I’m actually I’m grateful for that time as well, because it allowed me to mature and understand what the product actually needed to be. I don’t think I was ready to launch an app at that point. And then that actually coincided with me leaving college at the time. So then I had more time to invest in it. So you can say it’s all worked out. But obviously I’m still right in the middle of the process as well. So it’s worked out to date so far. 

Matt Wolach  18:58

Yeah, I mean, you’re doing great. You’re on your way up. And it’s really cool to see one thing I want to ask you about, you talked about how of course golf in many areas of the world. It’s seasonal. And so that creates a big challenge for you selling to these golf courses. In fact, lots of people have an app have a software platform that they’re selling to an industry that’s very seasonal, how have you handled it to this point, and what are some of your focuses around, Maybe, do you do go with it? Do you try to  make it more flat throughout the year? What do you do?

Graham Curry  19:29

Yeah, it’s a good question. And especially for us starting out, because our focus was very narrow on the UK and Ireland market where it is, as a very seasonal business. April to October will be what the golf season is. So honestly, we didn’t find it starting off. We just said our pricing was actually usage based at that time. So you pretty much paid for each job you put in the system. So our revenue actually was seasonal at that time. There was no there was no winter revenue for the first 12 months, which was kind of tough because you get through the season and you’re like, here we go for the next six months.

Graham Curry  20:11

It was like, yeah, it was like a squirrel gathering their nuts for the whole season. We actually, it was actually a few months ago. So we got clients in America recently enough, and they’re not seasonal, which is great. So it’s obviously a year round revenue. We’ve actually got a customer I mentioned for the podcast and Thailand. And obviously, the weather there, they almost nearly don’t have seasons, it’s just mid 20 degrees or whatever, 75 degrees Fahrenheit in US. And they’re just, they’re constant. And they’re actually really busy caddy programs as well. So that’d be one of our highest MRR customers for revenue, we actually had another idea in terms of our pricing strategy. And I was actually through with the fast action discount that you mentioned. So we, we still offer usage based pricing if clubs want to do it that way. But we also offer a discount on their rates if they want to pay upfront. So let’s say for example, a golf club does 10,000 caddy runs per year. So we’ll say at x price provide. But if you want to pay up front, we’ll give you 25% discount on that rate and just talking to my team there, we got four upfront payments from that in the winter months. So ironically, we’ve actually generated more this winter than we did the entire last summer, because we’ve got incentive there for people to pay up front. And, you know, we’re not worried about churn whenever they come on our retention rates pretty high. So we don’t worry about them leaving, but it’s just, it’s obviously great to have that upfront cash flow, especially at this stage with cash flow is so important. So that’s why we’ve tackled it at the minute.

Matt Wolach  21:56

Yeah, what a smart way to overcome that seasonality. Did you ever believe that your winter revenue would beat the summer?

Graham Curry  22:03

I had no idea. I can’t take credit for this idea. Again, this was Jimmy, my co founder, perhaps we should put him in sales because that was a blinder of an idea.

Matt Wolach  22:12

So hey, great ideas can come from anywhere. It’s awesome. 

Graham Curry  22:16

Thats it. And I think, going to your point as well, I think you mentioned that everyone in your organization is in sales in some degree, especially in our organization, whereas it is a lot of in person contact and conferences and things like that. So for him to kind of take on that role as well and not just be a software head was was very helpful for that idea.

Matt Wolach  22:40

I love it. I love it. So cool. Okay, so as we wrap up, I want to understand what advice would you have for other software founders who are in those early days trying to gain traction? What would you share with them? 

Graham Curry  22:52

Yeah, I’ve thought about this a lot over the last few months. And I believe genuinely that persistence is just so important. I think that is the underlying bed of everything you do. Because fundamentally, if you don’t give up, you either, genuinely you die trying, or you will find a solution. So actually, I wrote a post about this on LinkedIn, but it was just my thoughts and what it is like to run a startup in the early days. And I think like, it’s almost reframing your success to say that surviving and running the business is success, actually keeping the thing alive and still doing it as your career, you’re already successful. Because that’s what you’ve wanted to do for your job, you’re not stuck in this corporate job that you don’t want to do, you’re actually following your passion. So the two outcomes of that will either be the business works, or you will learn the lessons as a person that you can then apply to your next venture. So provided you just stay the course there actually really is no bad outcome to a degree. And I think that’s given me a little bit of assurance that regardless of how this turns out, obviously, it’s looking good right now, but you never know in the startup world that you there’s just so many lessons personally, from the perseverance side of it to the empathy side of it, you mentioned about learning about customers and learning how humans interact and learn how to sell. I mean, sales is the most universal skill, we apply it in every element of our life. So being able to learn that fundamentally will improve the quality of my life further on regardless. So I think, you know, I’m guilty of this at times as well. You lump this pressure on yourself and say, it’s either this startup has to work or and then you spiral down and say I’m gonna have to get a real job and things like that. But it’s always saying like, simply by following the process and commit to yourself, you’ve already succeeded, and the results will show so I would I it’s almost more emotional support I would give to people I’ve just say Just follow the process and you’ll either learn or when one of the two will occur. I sound very wise there.

Matt Wolach  25:06

you do that’s amazing. Like we need to put that on a plaque or something’s brilliant. Well, cool, Graham, this is so awesome. I really appreciate you coming in and sharing all this with us. How can the audience learn more about you and Handicaddie?

Graham Curry  25:20

Yes. So very simply, I’m quite active on LinkedIn. So if you want to connect with me, it’s just Graham Curry. It’s, it’ll say, find your Handicaddie. So connect with me there. And if you want to check out the site, it’s just for anyone in the golf industry will be happy to show you.

Matt Wolach  25:37

Okay, perfect. We’ll put all that into the show notes. So if you’re listening or watching, you’ll be able to grab all that there. But Graham, thanks so much for coming in and sharing all this.

Graham Curry  25:45

Yeah, I appreciate your time, Matt, thanks for having me on. It was a blast.

Matt Wolach  25:48

Absolutely. Likewise, and everybody out there thank you for being here. I appreciate you watching and listening. Again, make sure that you’re subscribed because we have a lot of amazing guests coming up in the next few weeks for you and you do not want to miss like what Graham just shared was incredible his journey you can definitely use a lot of what he’s learned so that you can apply it to your own business. Others like him are coming up. Make sure you subscribe so you don’t miss out. And we will see you next time. Take care. Bye bye