Finding Product-Market Fit with Matt Holder

Marketplaces rarely launch with a hole-in-one. For Matthew Holder, founder of Loop Golf, start-up marketplaces should expect to whiff. It’s part of the process. 

While working on marketplace product teams, including AutoList, Zillow, Houzz, and Trulia, Matt saw time and time again how marketplaces could revolutionize industries. He also developed an eye for marketplace opportunities. His idea for Loop Golf began with trying to solve his own problem: booking tee times, which he found frustrating, time-consuming, and highly inconvenient. 

Today, Loop Golf streamlines the booking experience by connecting golfers with the best tee times at busy golf courses. The marketplace acts as a concierge that helps golfers play where and when they want to play, and golf courses benefit from filling inventory that would otherwise go unused. 

Like many successful marketplaces, the current iteration of Loop Golf was not the first iteration of Loop Golf. 

What To Do When Your Product Market Fit — Doesn’t

Loop Golf began as a simple web app that tracked GPS data relevant to golf, like shot tracking. “It sucked. It was so bad,” laughs Matt. “It didn't work, but I learned a lot from it. Like, here's how I would do it if I were going to do it differently.”

Despite the lackluster reception of his initial prototype, Matt did venture down the path of iterating the app. His big learning? The product would face a never-ending uphill battle against a crowded market.

“Product market fit is a moving target. It’s never fixed,” he says. You have to hit it once, ride that out, and keep working on it.”

Empowered by the learnings of his prototype’s failure, he completely changed course.

How to Determine Product Market Fit

Crawl, walk, run—it’s an adage all marketplace operators should live by. Crawl, walk, run is a three-step approach to a marketplace launch that focuses on a quick, lean go-to-market and the goal of evolving based on real-world feedback. 

When Matt walked and subsequently stumbled with Loop Golf’s V1, he teased out the market's needs and created a product that solved them. 

Here are three things he solved with Loop Golf’s second iteration as a distribution channel:

1. Constraint-fuelled demand: 

In most cases, a marketplace will be supply-constrained, meaning there’s plenty of demand but no supply. Therein lies the key to a marketplace’s success: build supply, and buyers will come. 

Loop Golf is a prime example of this. No developer is going to build a golf course in a major metropolis. Even if the space were available, it would be cost-prohibitive. Supply constraints led to surplus demand for tee times in cities that the golf industry hadn’t addressed—but Loop Golf did.

“We have a system that if someone cancels a tee time at the last minute, we can come in, book it for one of our customers, and relieve the effort and time [the player would spend] trying to constantly monitor a course to find that for themselves.” 

2. Competitive differentiation: 

Matt wasn’t the only entrepreneur building tech to solve the tee-time problem, but he did make Loop Golf stand out by offering extra value to his suppliers. Unlike competitors, Loop Golf doesn’t offer tee times at a discount to buyers. Golf courses make full revenue on every spot that is filled.

“We're helping generate a full-rate golfer, as opposed to a discounted fair that would take money from their bottom line. Traditionally, there've been a lot of sites that do discounting to help fill that gap. We’re able to recapture a bunch of revenue so they can hopefully reinvest in their course and improve the conditions and playability and enable more golfers to enjoy their facility.”

3. Pricing: 

Loop Golf makes money by charging golfers a small fee for booking. To make the charge worth it for its buyers, Loop Golf had to make sure the wheat was worth the chafe. For golfers, it’s worth a 10% fee to get the exact booking time they want in a nearby location. 

“You've got a five-hour window in which you can play golf on a Saturday before you have to go hang out with friends or do something with the kids. And either you get a tee time or if you don't, you're not playing for maybe another two weeks. So, it's very worth it for our customers to use us to get that tee time.” 

Launch (And Fail) Faster With Off-the-Shelf Tools

As you can imagine, killing the marketplace vision you’ve invested time, money, and emotion into is no easy decision. “It’s hard to hear a bunch of people call your baby ugly,” says Matt. “You have to have an iron stomach to get through that.” 

It also helps if your marketplace uses marketplace software  so you can validate your marketplace model and make adjustments without reworking the wheel. Matt gives three reasons why off-the-shelf solutions help marketplaces become successful. 

Marketplace software helps you get started 

Changing the vision isn’t a failure. Not starting is the failure. “Like once you get started, it's a lot easier to keep going despite the negative feedback or things not working out, but you’ve got things once you get things flowing.”

Launching a marketplace can feel like eating an elephant. Off-the-shelf solutions help you launch one bite at a time.  

Marketplace software helps you learn

Matt believes you don’t need to have the right plan. You just need to know a problem exists because you can start learning.

“Learn as fast as you can. [..] Validate that the problem exists for other people. Validation is huge. Validate that, you know, people would be willing to pay to solve that problem.”

By building your marketplace using out-of-the-box software, you can quickly create a minimum viable product that helps you launch as quickly as possible — so you can start learning.

🔵 What is a minimum viable product? 🔵

Marketplace software helps you build quickly and cheaply 

An oft-overlooked benefit of pre-built marketplace software: the healthy emotional distance it gives you from your investment. Sunk costs syndrome is human nature. The more resources and time you’ve invested in a project, the more likely you will keep investing in it despite evidence that it’s not working. Pre-built software also allows you to launch fast and fail fast eons faster than custom development — without the trap of sunk costs. 

Matt explains why this is so important:

“Build something quickly, build it as cheaply as you can use out-of-the-box tools. Launch it, put it in people's hands, and have them tell you it sucks. Great. Why does it suck? The best position for me as a product manager and as an entrepreneur has always been either this sucks and it's horrible, or this is really great.” 

Lessons for other marketplace operators: Use a build-launch-learn framework

Matt is a proponent of build, launch, learn— a process he equates to the scientific method of building a marketplace.

“To me, [build, launch, learn] is the scientific method that has really helped me find failure or success as quickly as possible. And out of both, you learn a lot of valuable things that you can take from there to build the next thing.”

He encourages marketplace entrepreneurs to embrace their fear of failure because the sooner you fail, the sooner you learn. “The quicker you can [launch,] the more quickly you can prove out the business or kill it. Those are both valuable places to end up.”

Transcript

Niklas: Welcome to Operation Marketplace. I'm your host, Niklas Hallusser, CEO of Nautical Commerce. Today, I'm here with Matt Holder, who. Both is building a marketplace right now and has also been [00:01:00] at, I think from what I can figure out four, five different marketplaces in his career, um, building them, working, um, in product for them.

Some have been acquired, some are household names. Uh, and, uh, and so he's, he's seen a huge amount of experience across. Not just multiple marketplaces. So can tell the story around the differences of those, but also multiple types of marketplaces. And we'll dig into that a little bit as we, as we go on with the podcast.

So without further ado, we'd love to hear, um, first of all, a little bit more of your, your story, Matt, and what you're up to right now.

Matthew: Yeah. Thank you again for, for having me on excited to. Share insights that might be helpful to, to everybody out there, I guess, kind of starting with where I'm at now is, um, for the past year, you know, one to two years I've been working on.

Building a marketplace in golf called loop golf, um, that helps golfers get the best tee times at busy, busy golf courses and our products, you know, as with many startups and [00:02:00] marketplaces that are early stage where we are now, where we're still working on product market fit. Um, we've been doing a lot of experimentation around the product, but, um, where we're finding success today is providing a way for a concierge system, basically for golfers that allows them to tell us where they want to play, when they want to play.

And then we take on the heavy lifting of constantly checking the golf websites to find the tee time that they want, um, at the golf course and then automatically booking it for them. So such that they, at, you know, 3 AM or 3 PM. They get golf in their inbox and they get, they didn't take any effort to do it.

And they get to show up and go play golf, which a lot of golfers that are our customers right now are just like, Oh my God, this is amazing. This is awesome. Um, as opposed to, you know, a couple of years ago when I was, you know, before loop golf existed and I was a frustrated golfer trying to book tee times.

A lot of golfers have to stay up [00:03:00] until midnight trying to refresh, uh, you know, search multiple different websites constantly, you know, hitting the refresh button, trying to find something that's available and they may get something and they may not get something like restaurants in New York. Exactly.

It's, and it's just such a hassle. You know, at some point I'm just like, you know, there's a tech, there's a technology solution here. That if anybody's going to do it, I can do it and at least solve my own problem. And I'm sure other golfers have that problem too. And so we really set out, how do we make the booking experience for golf 10 X, a hundred X better than it is today, which is just a complete hassle.

So, you know, that's what I'm doing now. And kind of the evolution. Of that has come from a series of marketplaces that I've worked at that on the surface seem completely different. But when you peel back the layers, there are a lot of similarities until and how those marketplaces operate and the problems that all sides of the marketplace have that need to be solved.

And so, you know, prior to loop golf, I was at a company called AutoList and they got acquired by CarGurus, which is the largest [00:04:00] automotive search site in the U. S. Um, before that I was a company called house that was in the interior design and remodel space running their industry product there. And then before that I was at, uh, Zillow and Trulia, um, and very early on at Trulia and prior to that, I started, uh, one or two companies in the real estate tech space that, uh, Eventually landed me into Trulia to begin with.

So that's kind of how I got into marketplaces to begin with. And it's usually solved with, you know, it started with trying to solve my own problem. Uh, and then kind of just through, you know, luck plus, you know, you know, work and being in the right space at the right time, just kind of evolved into working in some of the, some of these really great Uh, big consumer tech marketplaces.

Niklas: Yeah. And a lot of people would say that if you're not spitting hairs, that, you know, brokers kind of our marketplaces are managed service marketplaces. They kind of are the product proto marketplace. So I think we can throw those into the, into the same, uh, same, uh, broad bucket.

But I mean, you were, you said you're building Loop golf, but I [00:05:00] try to catch you out and get on your website and look at every single state. And I really figured I could find, you know, a niche state where you don't have. Well, you don't have golf courses and I failed my long shot was district of Columbia, but you've got 25 in Washington. How many golf courses do you have now? 

Matthew: That's a really great question. We're, you know, we're in the, in the high hundreds, um, but about to be, you know, a lot more, you know, it's with, with a lot of marketplaces, the biggest challenge and why marketplaces are so hard is you got to solve. You know, seemingly solve for both sides of the market simultaneously, which is like any marketplace founder who's been there understands as just, that can be incredibly frustrating and hard to figure out.

And so you're like trying to figure out how to break that cold start problem with getting the marketplace kicked off. And from the marketplaces that I've been a part of, and, um, the entrepreneurs that I've been able to interact with and learn from, like. [00:06:00] Pete Flint at Trulia and Corey Lidstone at Autoless, uh, Rich Barton, um, you know, Spencer Raskoff and, and the like.

Um, you know, a lot of them will, will very quickly say the hardest, like you have to solve for the hardest side and wherever the marketplace is. And typically in the marketplaces, like, like, uh, with golf and automotive and real estate, the supply side is The hard side to, to build and scale.

And unless you have supply, you're never going to generate demand. So while generating demand isn't easy and getting in front of, you know, millions of consumers and building up that brand isn't easy, um, you'll never get there unless you have the supply side. And so we've been, you know, focusing after doing a lot of product testing, just to validate that people even want to buy the thing and work with us and find our products valuable to use.

Then it's like, okay, let's scale up the supply side so that we can start, you know, generating [00:07:00] demand outside of a few key markets where we did our initial testing. 

Niklas: Got it. And where does, where are you guys? In terms of your, your, your journey in that case. So you've gotten, you have a hundred golf courses or so you've unlocked something on the supply side or build something there.

Are you in the process of scaling the, the, the demand side? Have you started scaling it? What inflection point do you feel like you're at? 

Matthew: Yeah. So I feel like we're just shy of that inflection point where I think. We can say we've had our first, uh, kind of solid sense of product market fit over time, product market fits a moving target.

So it's, it's never fixed, but you know, you gotta hit, you gotta hit it once and then ride that out and eventually you have to keep working on it. But I feel like we're just shy of that. So we've done a lot of testing of Um, the, the user experience, the product pricing, um, how we do fulfillment, our pro our internal processes to get tee times for [00:08:00] golfers.

We feel like we've vetted each of those individual pieces enough where. And, uh, you know, in a primary market LA, um, it's starting to work really well. And now we know that we're ready to start expanding to other markets. So first is getting the course coverage and making sure things work. 

And then from a marketing standpoint, We're going to go, um, you know, market by market within the U S and start focusing on building out market. Number two, market number three, market number four. And if naturally that bleeds over to people booking and other markets, we're not actively marketing in yet. Yeah. Great. We're happy to have that too.

But you know, we're trying to remain as focused as possible on matching demand with supply that we have. 

Niklas: Yeah. I'm going to take us a little off track. Do you expect that this is something more likely a fit for like urban areas where you just got a huge amount of competition for like, let's call it a limited real estate for golf courses?

Or have you seen this [00:09:00] also, you know, have a big impact on rural areas?

Matthew: I think you're right in that, you know, initially it's, it's targeted at, uh, urban areas and especially high density urban areas. You know, the unique thing about golf courses is that over the past, I don't know, two, three, four decades, the amount of new golf course growth has never outpaced the number of courses that have closed.

So, you know, you have a lot of courses that have been built on the periphery of. know, urban areas that come up, they come and they go and they come down. Um, and then you have these courses that have, have remained in, in these dense urban areas. Like LA is a great example. You've got like Rancho park and Encino golf course and uh, Griffith park.

Um, And they're surrounded by this massive megalopolis and they're not going to be dropping any new golf courses, any anywhere in the middle of LA anymore, because it would be prohibitively expensive at this point to do, um, you know, to buy up a [00:10:00] hundred acres and build a course that would cost billions of dollars probably.

Um, and so you have now this huge supply shortage. These dense areas and a ton of demand, especially over the past couple of years, the golf has really taken off. And so, um, you know, the golf industry has really struggled with how do you balance that increase in demand with the booking experience? And. And, you know, what golfers are able to do, especially golfers, uh, nowadays that are, that are skewing a lot younger than they used to in previous generations.

Niklas: So when you have that dynamic, I mean, golf, I don't want to be judgmental of golf, but it's a relatively traditional conservative minded, not politically from a, from an attitudes perspective. sport and, and to your point, there's a, you know, there's a sort of a demand that outstrips supply. What's the story in that case for you finding [00:11:00] more demand for these golf courses?

Why are they choosing to work with, with loop golf?

Matthew: Yeah. So, um, I think like the story is really focused on, on the golfer themselves and, uh, you know, golfers these days are, Becoming a lot less traditional and the sport is, is kind of, is opening up a little bit in terms of attitudes towards attire on the course and behavior on the course, you know, three decades ago, there would never be, uh, you know, you'd never have a, uh, uh, you know, a boom box or, um, uh, speaker on, you know, in your golf cart or on your bag as you're playing around playing your favorite music. Um, and dressed in shorts and a t shirt. 

Niklas: Yeah. That's heresy in golf. What are you, what are you, what are you talking about? You got kicked off a golf course for that.

Matthew: Yeah. You, you, you know, decades ago you could, but these days it looked at public courses, you know, the attitudes towards [00:12:00] that are changing a lot and the golfer has become a lot younger, um, largely due to, you know, fueled by the pandemic and, and people looking for things to do.

Um, but also because of the change in, in the landscape of youth sports and a lot of. A lot of parents of kids trying to get their kids away from high contact, um, high injury sports into sports like tennis and golf. Um, that has really causes like huge, huge, uh, surge in participation among, uh, you know, among people under 45, especially under, under 25 and golf.

Um, and I think that that's where, um, that kind of like the pain experience of, Trying to find a very scarce resource, which is like an 8 a. m. tea time on a Saturday, um, is solved by a product like ours, where, you know, we have a system that should someone cancel a tee time last minute or four days ahead, we can come in, book that for one [00:13:00] of our customers and relieve the effort and time spent trying to constantly monitor a course to try and find that for themselves.

Niklas: Okay. And so as a result, if I, if I kind of. Play that with a different angle. They also don't have to spend the time building tools, outreach, marketing, you name it. To make sure that they have, I guess how they make money, which is maximum occupancy, right?

Matthew: And so our product is on the, on the core side is we're helping, you know, generate for them a, uh, ready and willing golfer that is taking up inventory that might otherwise go unused at a, you know, as a last minute cancellation and put money back in their pocket.

And especially in, in the core side of things, the unique approach that we have is not only is it doesn't, it doesn't cost them any money to get that benefit. We're helping generate a full rate golfer, as opposed to a discounted fair that, you know, would take money from their bottom [00:14:00] line. And I think traditionally there've been a lot of sites that do a lot of, you know, discounting to help fill that gap.

And we're not doing that at all. So it's really like two, two really great ways that courses are. Able to recapture a bunch of revenue and hopefully reinvest in their course and make, improve the conditions and playability and enable, you know, more golfers to enjoy their facility. 

Niklas: As much as I appreciate the public service of getting people out there doing sports and not spending their life on, on fortnight and tick tock.

I assume, or I would hope that, that you've got a good commercial model around all of this. And that's how these things are successful. What, how, how do you guys make. Make money in connecting the two, right?

Matthew: So, um, what we've done so far is we take roughly about a 10 percent fee for helping book a tee time for a golfer as a golfer.

You can request a booking. Absolutely free. No money up [00:15:00] front. You only pay when we successfully book a tee time for you. Um, which I think is a, is a great fair trade, um, you know, for the golfer. 

And, uh, when the, and when we do convert for them, um, you know, the feedback that we get is, you know, they're just like, Oh, I would do this a million times over because it's just.

You know, it's really inconvenient to try and do this ourselves. So we take a small portion, which on a, on a, you know, average tee time or green fee as they call it, um, of like 50 bucks, it turns out to be another 5 per player or something like that, which to them is a drop in the bucket when. You've got, uh, you know, a five hour window in which you can play golf on a Saturday before you have to go.

Hang out with friends or do something with the kids. And either you get a tee time during that, you know, to play, or if you don't, you're not playing for maybe another two weeks. So, uh, it's, it's very worth it for our customers to, to have, to use us, to, to get that to time. [00:16:00]

Niklas: That makes sense. And I actually want to dig a little bit more into what you said earlier about interesting fact that you've had more, if I understood that correctly, you have more golf courses closing than opening.

For the last three or four decades, I'm a big believer in general marketplaces, by the way, and we can chat about that later, that having a really good understanding of the incentives or the problems that both your supply and your demand side really face. Right. So, and that's, we understand that core businesses, which makes a difference when you make a successful Marketplace because you really have to, you know, it would only wins and generating value for both sides. You know, the, the thing that's actually playing in my head right now, right? There's a, there's a lot of demand for practically limited supply of gold courses. They're hard to build, right? You need to find real estate.

Enough space, you name it. Um, so you have a little bit of a, let's call it a local monopoly on your, on your local customer base. So why are golf courses closing as a result? 

Matthew: I think that the, you know, when you dig [00:17:00] a layer deeper into that, the, the golf courses that are closing are not the ones that are in the dense urban centers.

You've got a lot of, uh, a lot of golf courses that are being built as like a resort course, or it's a facility that's completely private or semi private as a part of a development that's 30 minutes outside a downtown area or the core kind of. Uh, you know, urban center. It's very hard to fill demand at those T at those courses if there isn't a robust set of, uh, you know, population around it.

And so we ended up having is that those are the only places where you can build new courses. Cause it's prohibitively expensive to build it in the middle of downtown LA. Um, but at the same time, it's really hard to generate demand for him because someone in downtown LA is not going to drive an hour outside of LA to play a 9 AM tee time on a [00:18:00] Thursday.

Those are the ones that find it very difficult to be successful. Whilst you have these other courses that have been there for, you know, over a hundred years in the middle of these urban centers that are just, you know, overpopulated with demand, uh, to, to play them. And that's where people are having a really hard time finding a tee time. Those are kind of like the, the things that play here.

Niklas: Yeah, it makes sense. And of course, I mean, to your point, to, to what you guys do, if you can increase, I mean, I don't know by how much they're going, they're, they're going bust, but if you can increase the, the occupancy rate or T, I don't know what the right term is T efficiency rate by 10, 20%, you probably drive a lot of those golf courses back into the, into the black with a single platform. And I'm sure most of those local golf courses aren't exactly the ones that have the tech to go and build a wonderful booking experience and a follow up experience and, and everything else.

Switching tracks a little bit, you've seen your variety of marketplaces now. What's different or special, or is there anything different or [00:19:00] special about loop golf or maybe, you know, sort of time slot booking, maybe in a more abstract marketplaces to some of the other ones that you've, that you've worked on?

Matthew: Yeah, I think that, um, the key difference between what loop golf's marketplace and the other ones that I've been a part of is that. Um, we're, we're very, very close to and participating in the actual transaction itself, whereas the marketplaces that I've been a part of are more of like a marketing, uh, marketing engine and leads marketplace that helps connect, uh, you know, home buyers with a real estate agent as its primary mode of, uh, you know, connecting both sides of the business, but not actually participating in the end result, which is, you know, You know, someone selling or buying a home.

And you've seen over time that like companies like Zillow, um, have started to march down the [00:20:00] path of trying to directly participate in the transaction itself, uh, for better, for worse. Um, you know, Zillow did try that and it didn't quite work out the first time. Doesn't mean they won't do it again, but I'm sure they have plenty of learnings to try and, you know, to glean from their experience there.

But ultimately a lot of these marketplaces want to. Get closer to where the value and money is actually exchanged. Cause that's where the most amount of value can be extracted out of, um, you know, out of the business. If Zillow was able to have a 10 percent take rate on every home that, that changed hands.

Every year, uh, their revenue would probably be significantly higher than it is today. Um, doesn't mean it's easy to do that because obviously it's not, but, um, I think that's a mentality that a lot of these marketplaces have and where they eventually want to be.

Niklas: When a marketplace can be part of the transaction and when they can't and how [00:21:00] early you need to pick a path for choosing one or the other.

Matthew: That's the million dollar question, isn't it? I'm not going to be so confident to say I have like a very specific answer to that because I think it really depends on the industry that you're in, how people expect to consume whatever it is you're helping facilitate. Okay. Um, and then a lot of it comes down to timing.

So, you know, Zillow and Trulia are a great example compared to OpenDoor. OpenDoor was started by Eric Wu and there are a lot of ex Trulia people, including Eric. That were part of that founding team and that early team that helped scale up that business. That business was directly, um, you know, directly, uh, involved in the transaction from the get go.

And it was purposely designed that way. Um, could have been done 10 years prior, probably not. Um, I think it needed people to migrate their searching of homes and shopping for, for homes. away [00:22:00] from primarily using real estate agents to using a service like Trulian Zillow as a stepping stone to being able to say like, yeah, I'm comfortable with transacting completely, uh, online with this, you know, tech company to sell my home.

So I think that, uh, a lot of it comes down to timing and then the opportunity of when you create that marketplace. Um, and, you know, Zillow has obviously tried to get involved in that, in the transaction too. And, you know, Open door and offer pad have had some troubles over the past couple of years in scaling up their business outside of these, um, kind of core markets where the homes are very homeogenous genius in terms of their construction and size and things like that.

So, um, they have plenty of challenges ahead, not to take away from the fact that they've built a multi billion dollar business. So, uh, they're still doing pretty well. It's just, you know, Product market fit is again, a moving target and they're, they're trying to find it again. It's just kind of the way it works.

Niklas: Yeah. And look, I mean, once you [00:23:00] have the flow, right. I mean, it's one of the interesting things that you have in marketplaces. Once you have the flow, people doing the transaction, there's always an opportunity to find how to add more value, how to capture a little bit more, how to, you know, be. effectively expand the fact that people are doing business on your, it's called a real estate.

And, and so is there anything else? I mean, if you sort of look at all the ones that you've, that you've been on, maybe there's a little bit of a, of a broad question, what else stands out to you from your previous experiences for, for how You know, in broad strokes, some of these marketplaces have varied from each other or have been different from each other.

You know, what, how do you, how do you categorize types of marketplaces that you've worked for? 

Matthew: That's a tough question for me. Cause I've, I've spent so much time focused on how similar they are as a product person. 

Niklas: What's similar about them? Like what's the same for all of these marketplaces? That's actually a, a good place to start.

Matthew: That's what most people don't recognize. And what. You know, in interview [00:24:00] conversations that I've had with, with people outside the business and even with founders of new companies I've joined, I've, you know, highlighting the similarities helps, helps kind of clear a clear kind of like a path of like, well, what's the roadmap and what could this look like?

Um, man, like when you look at real estate, home improvement, automotive and golf, there are several key players and key roles within the business that exist in all of those different, all of those different industries and, and, and verticals 

In real estate. You have a broker or brokerage like Coldwell Banker or Century 21 or remax, um, that employs a bunch of agents that work for them and help actually do the transactions. And this business runs, this brokerage runs all of these people and dictates how they get paid and when they get paid and things like that with, uh, you know, home buyers and sellers. Um, that are [00:25:00] very rarely engage in peer to peer transactions, but do, you know, use those brokerage services to facilitate those transactions.

In home improvement, you know, you've got independent contractors and you've got large contracting businesses and large brands that, that operate a bunch of people that, that do the work. And then you've got, you know, homeowners that are looking to remodel and, 

and with an automotive, which is very similar to real estate, you've got these huge, uh, automotive companies like AutoNation that. Uh, run franchises of, uh, you know, of car dealerships and dealers that work with them and regional managers. And CarMax is another big one. And then you've got, you know, car sellers and car buyers. And there's a model where majority of the car selling goes, doesn't go peer to peer, but goes through dealers and dealers control a lot of that transaction flow.

Um, and there are a lot of problems that each side of those, like every side of those markets and those, uh, kind of, you know, multi multi sided marketplaces have that, [00:26:00] um, causes a lot of tension and a lot of problems in terms of. Transparency and what's happening and how things work that prevent people from, you know, working efficiently.

And I think when you talk to like someone like Rich Barton, who's helped start a lot of these marketplaces, he's, you know, Expedia founder, Zillow founder, Glassdoor founder, his, you know, his. Uh, rallying cries, you know, shining light on the dark hidden places of, of these markets where there's a lot of inefficiency and confusion and giving clarity to everyone so that they can just do the trend, you know, do the transactions and be happy with how things work.

Um, so to me, like when I see those setups and I look at golf, golf is again, very similar, you've got these big management companies and some independent golf courses. Management companies that, that manage a lot of courses that are operating things and ideally want all of their customers only to go to their, their [00:27:00] courses.

Uh, and then you've got, you know, the, the golfers on the other side that want to consume these two times and go play these courses. And there's a lot of inefficiency and lack of transparency between how things are priced and what's available and how you can actually find, you know, places to golf that make it really frustrating for someone like me trying to book a tee time.

For the five hour window that I've got on this Saturday for the next two months, um, to, you know, go out and play with my buddies. So, uh, to me, the, all those similarities blend together. And I think when you look at the product development and the development of the marketplace and some of these other marketplaces, you can see a lot of the things that, um, will likely be work in some capacity with this new vertical within golf, Obviously, you can't carbon copy everything, but it can inform a lot of your product development, or at least what you're going to test to figure out, well, how can I take some of these same levers and some of these same problems to solve it uniquely within [00:28:00] this, this vertical, and just be informed of how I might do that.

Niklas: The framework, the playbook of shining light on the industry. Was something that goal for golf tee booking is ready for. How did you build that confidence? What research did you do? How did you get there? 

Matthew: That's a great question. Uh, you know, I think first off, just to like help other founders out, because it's something that I think every founder struggles with is just kind of a bit of imposter syndrome.

Um, I, you know, honestly, like. I go from being very comfortable with it to not comfortable at all, all the time. And it's just kind of, it's just part of being a founder. And it's just the rollercoaster of emotion that's involved with like, someday you feel, you feel like, wow, I've actually got things figured out.

And other days like, wow, like what is going on? Like, will this ever work? You know, I struggle with that all the time, but in, you know, trying to look at the highlight reel of things that we've done over time, Um, you know, it kind of, I guess just started with a, a na naive expression realization that [00:29:00] this is broken and it should be fixed.

Uh, second is just like, am I the person to fix it? Sure, why not? Let's give it a shot. And so I started doing, you know, doing some prototyping, moonlighting with, you know, at, you know, my previous job. Just trying to get a sense for like, is there a, there, there. Can I get any sort of signal that this might be something and, you know, doing some prototyping and doing some, uh, you know, some research and, and some very lightweight kind of like surveying of golfers and trying to get a sense for, um, you know, price sensitivity and, and demand and problem sizing.

I eventually got to the point where like this, there's a problem here. It needs to be solved. I don't necessarily know how to solve it, what the size and shape of that solution is going to be yet. Yeah. But something can be done and there's a sizable opportunity. Um, and we've had a big journey from, uh, you know, trying to figure out what our product was and our product today, it looks so much different than it did.[00:30:00]

You know, a year and a half ago to two years ago. Um, and that's just a result of just looking at realizing there's a problem to solve and then being okay with saying like, whatever the previous solution was, it didn't work, just kill it, learn and take your, take the positives and the learnings from what you, what you got out of that previous effort, and then tweak it into something new that, that helps solve those, but builds on top of it in a way that, that solves more of the problem.

So we've just been doing an iterative process of that over time to try and figure it out and. You know, we're not going to stop, but, you know, we feel like we're, you're, we're building momentum in the right way, that in a profitable way, from a, from a unit economics standpoint, that there's a business here and we can, we can continue to go.

Niklas: And what did you have to, you talked about the development of the product. What did you have to build? Did you, did you get your tech off the shelf? Did you? You know, have you, have you, have you built it all? You know, what's been the, what's been the, the [00:31:00] effort to get you to something where you, you're comfortable that you can handle that transaction.

Matthew: So, uh, I mean, getting, getting really, really detailed than that. The first iteration of our product was actually had nothing to do with directly selling tee times. Um, we started with, uh, what's, what's become very popular in the golf community is GPS app that helps golfers get yardage to a sand trap or yardage to the green so they can figure out what club to choose.

And we built that and we started that cause we're like, Hey, this is going to be. Maybe a great, um, high engagement, high retention distribution method for eventually helping golfers get tee times.

Niklas: Oh, interesting. So it was a really a plan. You already had the marketplace hat on, but we're coming in from sort of like a vertical market, vertical software, kind of an approach or.

Yeah. You know, vertical hardware, whatever the right time is.

Matthew: So the first thing that we built, the first thing I ever did was I, I, I hired a contractor [00:32:00] to build a, um, to build a, a very simple web app to just do some like GPS stuff and in doing like shot tracking. And, um, the first prototype, I took it out on the course.

I'm like, Hey, I'm going to use it. And it sucked. It was so bad. It was so bad. And, but I'm like there, but there's, there's a better way to build this, but you know, you learn a lot from it. It didn't work, but I learned a lot from it. Like, here's how I would do it if I was going to do it differently. And here as a golfer, here are the reasons why this would never work for me.

Um, and so. We went down the path of iterating that and then eventually we built, you know, our own app to put in the app store and, uh, you know, over time, as we built up that app, we, um, realized just how crowded that market was for GPS apps and as a distribution. As a distribution channel for helping golfers, you know, engage in the game and then [00:33:00] eventually helping them book two times for this app, we realized this is going to be a huge uphill battle.

So we started focusing completely on, you know, web development at that point. And while we still have a bunch of people who use the app, who love the features that are in there, we're like, it's going to be a lot easier for us to build, um, build up our audience on web and get transactions flowing on web, which then we can later use the app as.

As you know, a way to drive higher engagement, high retention and, and higher transaction flow at some point in the future. So, um, from then on, we've just been focused on, on the web development stuff, but along the way, we've done pricing analyses and, uh, you know, I think we did a, one of the key questions that we had early on are like, are golfers willing to pay some amount extra for tee times, you know, the Because we're going to, we have to charge them a fee.

So are they willing to do that? And we knew some other marketplaces charged a bit of a fee, but they're also discount marketplaces. Um, so, you know, would golfers pay a little bit [00:34:00] extra for a premium tee time? And so we did some of that analysis and found, or, you know, very quickly that it was a resounding yes.

And so once we had some of those pieces in place, we're like, okay, interesting. Like we know it's everybody says they hate booking two times. It really sucks. They'd also be very willing to pay a premium for T for like premium T times. Um, so, you know, there's a huge disconnect here in terms of what willingness to pay is and the problem that they're trying to solve.

So somewhere in between there, there's a software solution that will make this a lot easier in a business to be had. And that's, that's kind of when we started putting the pieces together of like, Hey, like this is. The opportunity we need to go for and try to figure it out. 

Niklas:Yeah. Not to sound like a know it all. but from my experience, it's something that I often tell people is especially when they're starting businesses is that the we'll do X so that we can do Y later is typically a hard way to make a business successful. And I tell them, [00:35:00] try to attack Y and see if that works first, right? Skip X because you're going to learn so much about Y.

That X will become useless anyway. 

Matthew: I think that's really great advice. And obviously as someone who's been around a bunch of marketplaces and. Done a bunch of stuff like it's hard to get away from. And, you know, I think one of the things that's really tough as an entrepreneur, as someone who, even as a product manager working in a large company, um, you tend to get fixated on an idea or what you think the answer is, or you're just so in the weeds and you're the papers right in front of you that you can't see, you can't see the green field on the other side of it and what all the, what all the possibilities are.

And. Um, you know, that can eventually make or break you if, if you don't pop your head up and, and get a fair assessment, a 10, 000 foot view of what's really going on. And so it was hard for us. Like we, we put money into [00:36:00] that and, um, you know, it didn't pan out the way that we wanted to, but we also learned a ton in that process and we've applied a bunch of that to, to what we're doing.

Niklas: Both the, the curse and the pleasure of being a product person is the curse. You have to go into those weeds. And you spend your life in them. But the ultimate pleasure is if you come out of it, come out of the, you know, macheteing through the jungle and you, and it clicks. When you find the solution, it's the best feeling in the world, right?

Because the constant game of, you know, diving, you know, surfacing, diving, surfacing, diving, surfacing, that makes, um, at the end, it makes great products. Right. And, and being able to kind of hold both of that or let both of them inform each other, because he's kind of sitting in between the, the high level business strategic and the, and the, and the nitty gritty of executing.

Um, but across, I mean, across all of these. And, you know, a lot of folks often, often obviously specifically to us, but in [00:37:00] general, I think one of the responses has been to, for example, this show, um, is, uh, is for folks to, to kind of understand, okay, how to get going. Right. And so one aspect of getting going is obviously having the right business idea and knowing or finding out, you know, how to, how to discover the right business idea, which I think we've covered a little bit, and typically I lean towards.

You know, if you, if you deeply understand the incentive, as long as there is a business to be built, you probably, you know, often on a really good start, but also often ask about then, you know, what's the practical aspect right of it. And it's, it's a little bit why I asked this question around, you know, you know, what, what do you have to build?

Where do you have to invest? You've seen a bunch of marketplaces, particularly in services and digital, which, you know, for my view are, are, are underserved from things that you can get out of the box. Um, from, you know, both Luke, Luke golf, but [00:38:00] also, you know, Zillow house auto list, this goes on truly, uh, um, uh, you know, what have you, what have you seen in terms of availability of, You know, tech tools, things off the shelf that get you started, or, you know, has your experience been that it's all been, all been custom?

Matthew: I think, you know, early on, especially for like, we're off the shelf, uh, tools are, are, are really, really helpful have been in just getting off the ground. And committing something to paper. I think what often happens is there's a, there's a failure to start somewhere. And I get it, it's high risk. Like it's really hard to build something and you're initially like, hopefully you're not investing a ton of money to get going, but you're are investing a lot of time and emotion into it.

And it's very hard for someone to hear, hear a bunch of people call you a baby ugly. [00:39:00] Um, and you just have to have like the iron stomach to get through that. And it's not hard. I mean, it's not easy. It's very, very hard, um, at every stage, but you kind of have to be willing to, to throw yourself into that.

And I think where, you know, where, what didn't exist in these previous marketplaces when they started were tools that you could employ out of the box to accomplish. Some of the initial things that just make it easier to get started. Like once you get started, it's a lot easier to keep going despite the negative feedback or things not working out or whatever, but you got things once you get things flowing.

Then you can start learning. And the whole point is like, learn as fast as you can. Don't you don't even need to have the right plan. You just have to know there's a problem. Then validate the problem is exists for other people. Validate is huge. Validate that, you know, people would be willing to pay to solve that problem.

Because if you're not [00:40:00] solving acute pain point for someone, then you've got nothing. So find that, find the problem first, and then start thinking about, well, how would I solve it? Build something, you know, using tools that are available out of the box to try to prototype something that helps you learn as fast as possible.

I think this might be the solution. Build something quick, build it as cheaply as you can use out of the box tools, launch it, put it in people's hands, have them tell you it sucks. Great. Why does it suck? That's like, honestly, as hard as it is, the best positions for me as a product manager and as an entrepreneur has always been either this sucks and it's horrible, or this is really great.

If you get something in between, you know, you're like, that's the zone of death. If someone's like, yeah, it's all right. You haven't made it controversial enough for people to say this is great or this really sucks. So go back and make something that's just really out, out of the box. Um, in terms of [00:41:00] your approach to like a potential solution.

But I think like, had those existed a long time ago, um, you know, I think that the, the length of time to getting to something that's. Achieved product market fit that timeline would have been collapsed quite a bit quite considerably. Um, then Uh, it was 10 or you know, 20 years ago when a lot of these companies started so I think there's a great opportunity for people to use out out of the out of the box tools like that to To get themselves to the point of trying to validate something and then realize like okay I can look either they stick with those tools or they go build it themselves, but Get to that point as quickly as possible.

Niklas: And so what does the future hold for loop golf? You sort of at the inflection point of growing now, you know, what's the, what's the end game for you guys, or, or are you not at a place to give that away yet?

Matthew: I think the end game is, is similar to where we are now. It's like the mission is like make the, make [00:42:00] the overall experience of, of booking and playing golf excellent. 

And there's a lot to be had in terms of, and a lot of problems to solve in terms of making the end to end golfing experience from booking a tee time to being on the course as, as good as it can possibly be. There's a lot of inefficiency. Um, and not that we're going to solve it. Any, any of these other things anytime soon, because Booking a tee time is, is hard enough and it's big enough where, you know, that's where our focus is today. But, you know, as a golfer, uh, showing up and not being, and like having to go into a building to present myself to check in and pay, and then, you know, walk somewhere to practice and then talk to someone before I go out on the course.

It's just like a lot of anxiety and wasted time. And, and a lot of that could be made better. Um, you know. Being able to book, you know, [00:43:00] find food while you're out on the course when you, when you get hungry and you know, you're spending six hours doing something and there's no food available. That's a problem too.

So, um, there's, there's a lot of convenience yet to be had and yet to be introduced into the game of golf and the experience of golfing that, um, could be, could be a part of our future at some point. But, you know, That's, that's five to 10 years down the road from where we are now. I mean, like you look at Zill and Trillia, they went public in what, 2011 and 2012.

So that was about seven to eight years after they'd been founding after their founding, um, And they didn't start introducing other, other revenue generating parts of their business until after they were public. So for a long time, they were very focused on their, their core first kind of, uh, you know, user experience and where they had product market fit.

Niklas: So what advice do you have, you know, beyond [00:44:00] actually a lot of the valuable advice that you've already shared or what advice would you, would you, would you want to pass on to customers? Really anybody starting on a business or maybe specifically a marketplace business, um, from all the things that you've learned.

Matthew: Man, I would say that the thing that that's, uh, the framework that's always helped me and, and something that I try to always be focused, focused on, and, you know, even though, you know, it's, it's hard to stick to, but admittedly, but, um, the thing that I find the most value valuable is. Uh, kind of this, this cyclical approach to building, whether it's product, whether it's feature, whether it's a business, um, which is build, launch and learn, and your goal is to make that cycle happen as quickly as possible.

And the quicker that you, that you can accomplish that, the more quickly you will get to the eventuality of. Either your goal [00:45:00] and proving out that you can build a business or you're going to, like, this is not going to work out and you kill it. Those are both valuable places to end up. Um, and I think everybody obviously has a fear of failure. Um, and that's what makes it really hard to adhere to that. Um, as an entrepreneur, like sometimes you're hesitant to do something because of that fear of failure and that's natural. Everybody has it. From the most seasoned entrepreneur to someone who's never, who's starting their very first thing. Um, you never lose it.

And so I think just being self aware of that and then thinking about, okay, well, how can I build this as quickly and as cost effectively as possible to launch it and then learn something very specific and do that as fast as I can and employ those learnings back into the next thing I build. Whether it's something completely different or you're just building on top of the original idea and then do that quickly again [00:46:00] and break it down in those small steps.

To me, that's the kind of the scientific method, if you will, or the framework that has really helped me find, find failure as quickly as possible or find success as quickly as possible. And out of both you learn. You learn a lot of valuable things that you can take from there to build the next thing.

Niklas: I can't support that enough, that statement. That's, I think, the key to win, particularly when you have nothing in it, you know, when you have no money, no customers. No information, no, anything as a startup, I think the only power you have is go faster, iterate faster, learn faster. Um, and it's the only way to solve that problem and, and, and to be absolutely ruthless about what not to do.

So, I mean, hugely enjoyed this conversation, Matt. Um, first of all, thank you for being on the, on, on the show. Um, [00:47:00] and, uh, and appreciate you sharing, you know, your wisdom and everything you've done before with marketplaces. Um, if somebody wanted to find you. And, uh, and reach out and, and learn from you, get mentorship, you name it.

Uh, where would they find you?

Matthew: Yeah, so, um, you know, you can obviously find Loop Golf at Loop L-O-O-P-G-O-L-F, loop golf.co. Um, that's our main website. You can find a, find a course to go book at. Um, and you know, there's ways that you can contact, contact us through there if you, if you wanna reach out. Find me on LinkedIn, Matt Holder.

I'm, I'm out there somewhere. Um, so, you know, feel free to reach out and I'm in, in a couple other communities for, uh, you know, investors and entrepreneurs that you're a part of. And you see me out there, feel free to reach out and happy. I'm always happy to share knowledge. And I come from kind of the school of.

Uh, sharing knowledge so other people can build great things. And I know as an entrepreneur, it's hard to find [00:48:00] learnings and bent performance benchmarks and all the things to try and figure out how to do something great. And. You know, I'd love to help out other entrepreneurs that way and just make sure that they have the knowledge they can to make the world better.

So that's what I'm all

Niklas: about. Appreciate having you on the show and best of luck with Luke. Thank you. Thanks for tuning in to operation marketplace. This show is brought to you by nautical commerce, the end to end marketplace platform. If you have any questions about optimizing or starting a marketplace, hit the link in the description.

We hope you enjoyed the show. See you next time.

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