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Founders’ Series: Todd Watson, Showit

Brands that Book Show

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Choosing Impact

Today we’re launching a new series within the Brands that Book podcast: The Founders’ Series. This series will feature the founders and CEOs of companies that have created products and services for the creative industry.

And to kick things off, I’m chatting with Todd Watson, the founder of Showit, a website platform created specifically for photographers and creative professionals.

This episode is a little different than previous episodes. Instead of focusing on tips, strategies or tools that you can use in your business, we focus mostly on Todd and the Showit story. I don’t know about you all, but I’m fascinated by stories of how businesses got started, especially businesses I admire, because I found regardless of the type or size of business, that there’s so many shared challenges that entrepreneurs face when getting started.

I’ve had the pleasure of getting to know Todd and the Showit story over the last few years, and I can tell you, it’s a good one. We discuss how Showit got started, how at one point there was uncertainty over its future and why Todd and his team rebuilt the platform from scratch into what it is today. We chat about why Todd opted not to take VC funding and the business that he wants to run.

Todd’s Biography:
When a photographer friend needed help building a website in 2005, Todd immediately jumped to action. Always wanting to help, and excited to crack his knuckles writing some code, he never imagined it would turn into a business. Anyone around him might have guessed otherwise. Before Todd had even set his 18 year old foot in a Computer Science class at ASU, he had already sharpened his entrepreneurial skills by creating two successful businesses. With his pioneering spirit, not to mention a supportive and trusting wife, Todd co-founded Showit with the intention of helping photographers bridge the gap between tech and creativity. Over a decade later, and 4 stunning sons, 24 employees, and countless Showiteers later, that gap is closing more and more.
Showit | Instagram (Showit) | Instagram (Todd)

Resources Mentioned in this Episode:

Previous Episode: Kaitlin Holland – Choosing Educational Experiences
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Founders' Series: Todd Watson - Choosing Impact | Brands that Book, episode FS1 | Davey & Krista
The Transcript:

[0:00:06.2] TW: If you’re not a photographer, like we may not be building the future for you. We’re really focused on what is it that a photographer needs to run their business. That helps us shape, it helps us to be able to say no a little bit easier. It helps us to be able to say yes in the right places and all those kinds of things.”

[INTRODUCTION]

[0:00:26.5] DJ: Welcome to the Brands that Book Show, where we help creative service-based businesses build their brands and find more clients. I’m your host, Davey Jones.

Today’s episode is part of the founders series, where we chat with founders and CEOs of companies that have created products and services that help creatives run their businesses. Today’s guest is Todd Watson, the Founder and CEO of Showit, a website platform created specifically for photographers and creative professionals.

Today’s episode is a little different than previous episodes. Instead of focusing on tips, strategies or tools that you can use in your business, we focus mostly on Todd and the Showit story. I don’t know about you all, but I’m fascinated by stories of how businesses got started, especially businesses I admire, because I found regardless of the type or size of business, that there’s so many shared challenges that entrepreneurs face when getting started.

I’m in the pleasure of getting to know Todd in a Showit story over the last few years and I can tell you, it’s a good one. We discussed how Showit got started, how at one point there was uncertainty over its future and why Todd and his team rebuilt the platform from scratch into what it is today. We chat about why Todd opted not to take VC funding and the business that he wants to run.

Be sure to check out the show notes at daveyandkrista.com for the resources we’ve mentioned during this episode. I’d like to hear from you about what content you’d like to see on the Brands that Book Podcast as we move forward. I’d also like to know what episodes you’ve enjoyed so far and why. To leave your feedback, head on over to the Davey and Krista Facebook page and send us a message.

Oh, and as a listener of the show, you can even get 10% off an annual Showit subscription by using the code BTB Show when signing up for Showit. That’s not an affiliate code. We’re just big fans of the Showit platform and want to share that with you.

Now on to the episode.

[INTERVIEW]

[0:02:22.6] DJ: All right, guys. We are here with Todd Watson, the co-founder and CEO of the Showit website platform. I’m really excited about this, because if you listen to this podcast, or if you’re familiar with Krista and I, you know that we love Showit, that now most of the websites that we designed for our clients are on the Showit platform. I’m really excited to dig in with Todd about how the Showit company got started, some of the challenges that they face, and I’m fairly familiar with the story, so I’m really excited for you listeners to hear about it. First, welcome Todd.

[0:02:53.2] TW: Hey, Davey. Thanks for having me on here. It’s good to be here.

[0:02:55.8] DJ: Yeah, I’m excited to dig in. First, for those people who don’t know what Showit is, can you just tell us what it is?

[0:03:01.9] TW: Yeah. We felt like when we look around the market, we see a lot of photographers that they just felt stuck in their website, whether it be stuck in a template, or just within WordPress, or something like that, they just felt stuck. We felt as a creative, we wanted to provide creative freedom for them to build the website that would be uniquely theirs and provide them the opportunity to connect with their ideal client.

We looked around, we realize that when you’re thinking about creating a website, you really want to be able to do exactly what you want to do and have that creative freedom. We made it very drag-and-drop, very visual, a lot more like a Photoshop as opposed to a lot of just menus that decide things. Everything is right there, the way that you would design an illustrator, or Photoshop, or something like that, so that you can actually create what you want to create when you’re doing your website.

[0:03:49.6] DJ: Yeah, and I think what separates Showit from a lot of the other drag-and-drop, or and I shouldn’t even call them drag-and-drop builders, a lot of the other builders out there you have to design within modules, within squares. With Showit though, you have a lot more flexibility over the design, and if you are a photographer, the back in the Showit I think feels like home to a certain extent, because it has the same feel as the Adobe suite.

I can use it, which means it’s not as complicated as the Adobe suite, right? It does have a similar feel to the Adobe suite. What’s interesting is that we’ve designed custom WordPress websites for a long time. On WordPress, you can pretty much truly do anything you want, but having that flexibility is often, it’s a problem for people. It’s actually a challenge; one, because there’s generally more maintenance work that goes into your website. Things break maybe a little bit more. Having something like Showit, we found that our clients love show it because they can go in and they can make updates on their own. Once again we get them set up with a with a beautiful-looking website, but after that they can make updates on their own.

[0:05:01.2] TW: Yeah. Really, that was one of the big things that when we looked around and decided on WordPress was we realized that there’s the WordPress way and this is when you dive into this idea, WordPress has a way to do things, and so you have plugins and themes and everything that work inside of WordPress.

The unfortunate thing is that really constrains you on the way that you can build a builder for WordPress, or how you can customize it. You end up getting stuck in the menus and then CSS and custom code and all that stuff where it’s really difficult to actually customize. People who have purchased themes, or done other things like that for WordPress they say, “Yeah, it looked great when I started, but I don’t know how to do more with it. I don’t know how to make this thing grow to what I want to be.”

What’s unique about Showit is that we’re not actually inside of WordPress. We’re actually a standalone platform. You don’t actually have to have WordPress to use Showit. You could just build a site entirely independent of WordPress. Then you can also design a WordPress theme in Showit and then publish that into WordPress, which isn’t really the WordPress way, but it works and it allows you to have this really great design experience without having the frustrations of being inside of the WordPress builder, that kind of thing.

[0:06:15.0] DJ: Yeah, I know. I think it perfectly combines the freedom of WordPress, but it eliminates a lot of the complexity because as you said, you’re working in a standalone builder and we take full advantage of that and that’s something that we love about Showit is that it has that integration, so to speak with WordPress. You can easily add, so not only can you create a beautiful website, which is the number one concern for a lot of people out there. If you want to easily add different functionality to it, the fact that it does have a connection to WordPress, you can add that functionality usually relatively easily with a plugin, which is really nice, which is really convenient.

First, Showit is a very different platform than it was – how many years has Showit 5, which is a platform that people are now familiar with, how many years has that been in existence? Two?

[0:07:01.6] TW: Yeah, we only launched in 2016, but we’ve been around as a company since 2006. We launched our Showit website builder back in 2008, so really it’s been 10 years since our original website builder that we designed. Back when we built that, it was on the flash platform. We were building flash websites, which at the time were spectacular. I mean, they were really engaging multimedia experiences. They were just something that you just couldn’t really do in HTML at the time.

It was a great platform. We had this full drag-and-drop thing that lets you build a site and you need to get stuck in templates and it was like, that was what we were about and that’s we’re going to do. Then along came mobile phones and as that started to take off, you’re like, “Okay, so how does this work with it?” We made some changes and adjustments to that. Then really when Steve Jobs came along and said flash will never be an iPhone, that was really when things started souring a bit. As the iPhone really took off, it really started to shape Adobe who had acquired flash and owned it was like, “Oh, man. If we can never be on the iPhone and they’re never going to push back on this, we’re probably going to move away from this.” Unfortunately, that platform was moved on essentially and they said, “We’re going to stop supporting it,” all those kinds of things.

[0:08:24.7] DJ: Yeah, here we are.

[0:08:26.3] TW: Yeah, here we are.

[0:08:27.2] DJ: Ultimately, I think, I mean, the platform now is out. We love it. It’s outstanding. I guess, the silver lining – I mean, from your – and I want to get into this in a second with you. I’m sure going through that change probably not – it wasn’t easy, right? What we have now as far as a platform, it’s amazing. Can you walk us through the beginning of Show it, what motivated you guys to actually, where were you? Were you always computer developer type?

[0:08:59.2] TW: Yeah. I had a computer background, but I was working at camp doing their video production stuff. My friend David J was this friend since elementary school and he was a photographer and was visiting one time and said, “Hey, could you build my website?” I was like, “Yeah, I can do that.” We built his first website.

Part of that was some slideshows for his photos for different weddings that he’d shot. He was like, “Man, other photographers really love this. The clients love these slideshows. Could we build something that would let photographers be able to build slideshows?” I thought, “Yeah, but we could put something together that would do that.” There wasn’t a lot on the market that was doing slideshows, there was Animoto, there wasn’t other things like that at the time.

We build our first version of what we call it Showit web. Because DJ was doing on-site slideshows and he wanted a way to put it on the web, so we built the slideshow product. I was working at a camp making pretty minimal amount of money, so I was like, “Now if we sell 50 of these, it’s going to be just crazy great.” That was my expectation at the time that we built it. I was like, “50, that would be good.”

[0:10:08.4] DJ: 50 is a good goal.

[0:10:09.7] TW: 50 is a good goal. We beat that goal. Over the next I think four or five years, I think we sold 15,000 or something like that. It was just insane. That was really the start of it, but I was working a full-time job and then just doing that on the side. We’re building that out and trying to figure out what we do with that, well only being a part-time gig and just doing it on the side here and there. It was like, “Is this just going to dry up overnight?”

It’s hard to know, especially in a business where you’re selling a slideshow product. It could just – it might sell one month, then the next month nothing. Who knows? There wasn’t any recurring revenue, any of those things. It was pretty risky at the time, but we finally said, “You know what? Let’s go ahead and go all-in on this and make a company out of it and actually build something.”

We started that in 2005, but really didn’t until late 2006 really decided, “Okay, let’s make this a company and go after this.” Then in 2007 is when I quit my full-time job and actually building and making sure a real company and that’s when we started – we decided, “Let’s build a product that photographers needed, which was websites to slideshows,” and say, “Let’s do that.”

[0:11:19.2] DJ: I guess, slideshows at the time like you said, I mean, they’re in demand and the whole same-day slideshow thing, right, was a thing. I mean, it still is a thing today, but you have no way of knowing is this going to be a trend for the long term. Isn’t that really what motivated you all to transition from being primarily a slideshow app, to a website platform for photographers?

[0:11:39.7] TW: Yeah, for sure. There was a lot of factors as we looked at it, because it would be crazy how great someone’s slideshow would be in and they put it on a website that was not great. When you’re looking around and going, “Oh, my goodness. The websites that are out there were just cookie-cutter templates that you could drop in a few photos and that was it.” We actually heard stories of people saying, “Oh, hey. Are you in collaboration with that photographer? Because you guys have the same website. Are you guys like a team of photographers? We were like, “No.”

You hear those stories and you’re like, “Oh, man. Just the state of websites was not great at that time.” We said, I think this is a way that we could really provide a valuable service to the industry, especially when it comes to being unique providing a website like that. We took our experience in building some software and said, “Okay, let’s build a team around this.” That’s when we actually formed a company and started hiring a few people.

[0:12:34.6] DJ: Can you talk a little bit about why you decided just to focus on photographers? I mean, working in the wedding industry, I feel like the wedding industry is one of those industries where the photographers are very aware of the planners that are out there and the florists and so on and so forth. At any point did you decide like, “Oh, well if we’re going to build the websites that photographers can use, why don’t we market two planners and florists and bakers and all the other pieces of that specific industry?”

[0:13:02.6] TW: Yeah, it’s a tough one. I mean, it’s one that we wrestle with even now. Those questions still come at us all the time. I think ultimately, what we’ve found is that once we start it – we’ve tried occasionally to do a few things like that and you learn very quickly that if you say, “Oh, hey. We also do church websites.” Then like, “Oh, can I have something to do with podcasting and can I do something to syndicate sermons and do other stuff?”

Then it’s like, “Oh, we do realtors too.” Okay, well can I have integration with listing sites and integration with this? All a sudden, your scope of the service that you can provide has become so wide and you realize like, “I don’t know if we can actually provide really great service to all these people at the size of team, at what we wanted to be.” We realized, we have domain expertise, we were around photographers – my former partner was a photographer. We’re in it for photographers and we had a good sense for this is what the features are that are needed, this is how we can do it, and we just – you have the opportunity to stand out as a focused niche.

We realized, you know what? We want to be the best we can be at serving photographers. Other people can come along and we have lots of other types of businesses using Showit, but ultimately, when they come to our site they’re going to know we’re about photographers. If you’re not a photographer, we may not be building the features for you. Hopefully, there’s a lot a lot of good things for you, but we’re really focused on what is it that a photographer needs to run their business. That helps us shape, it helps us be able to say no a little bit easier and it helps us to be able to say yes in the right places and all those kinds of things.

We’ve just decided that’s the direction that we’re going. The thing that I’ve told people in the past is like, until we have no opportunity to grow, then we can talk about other markets. As it stands, there’s so many photographers that we have opportunity to serve that there’s no reason for us to take our eye off that ball.

[0:15:00.9] DJ: Yeah, yeah. One, it’s not like the photography market is small, right? It’s still a big enough market where you can run a profitable company. I really wanted to ask you that question, because I think it’s an issue that so many people struggle with, especially when they’re first getting started in whatever industry it is, they have an opportunity to serve most likely all sorts of different clients. It’s so hard to niche down, it’s so hard to say, especially if somebody’s ready to put your services and maybe they’re not quite the client you serve, it’s so easy to say, “Yeah, I’m going to take that client.” By taking that client, can you serve them really, really well?

I think one of the reasons that so many other kinds of creatives have found the show at platform to be such a good platform for whatever the domain is because you guys have been really, really focused on building something for photographers and serving them as well as you possibly can. Maybe you would agree that if you tried to build something for everybody, you probably end up building something for nobody and nobody would quite find enough value in it.

[0:16:03.8] TW: Yeah, for sure. I think that is definitely the piece that’s – it’s hard, because there’s so many times where it just feels like, “Oh, if we just did a little bit more of. We just did this, it won’t be a big deal.” Every time you give that inch, there’s just this sense that you lose credibility, you lose the sense that who you’re about and those things. When we can be very firm about that, you’re going to find that people are going to connect. They’ll understand our vision, our mission when it’s not like, “Oh, well we’re also for dog groomers and they’re great too.”

When we start weakening our message, then – and I think it’s the difference that you’re going to see when you go to a Wix or Squarespace, also you’re going to go and choose between which template to start with and it’s like, “Well, I’m not a restaurant, but maybe I’ll customize this menu to be my photography menu.” It doesn’t always relate very well and then you’re like, “Oh, man. It would be really nice if I was just working from something that was really designed for me,” and I think that’s where our value is we’re going to say, “Hey, we’re going to be starting from what’s valuable to you and as a photographer and booking clients and taking care of them and providing different services.” That’s what we’re going to be about. That’s where we’re going to help you.

[0:17:15.0] DJ: Absolutely. There’s stuff that happen in the meantime though, from old Showit, so you decided to pivot and you’re building a website platform, the old flash-based platform for photographers. Somewhere in the middle there, you were actually part of, or that same company had launched another product, right? You guys launched pass.

[0:17:36.5] TW: Yeah, so what happened was that we were building our website product and we realized, “Man, it would be really great to be able to provide a way for our customers to have better galleries for their clients.” We’re like, “Well, let’s build a gallery tool instead of Showit.” Then as we looked at the market, we realized that there was a lot of shoot and burn photographers delivering on CDs, it’s just real frustrating.

We said, “You know what? Actually this is beyond just websites. This is photo delivery.” We said, “You know what? There’s a bigger opportunity here for us to do photo delivery,” and that’s where we started pass, and sure enough, that was one that took off even faster than Showit did, because it was such a need in the market to be able to deliver photos.

It was so much more efficient, so much better than handing over CD and then people never put it in a computer. A lot of them didn’t even have a computer that had a CD in and you’re like, “Oh, what do we do with this?” It was a great product and that thing started taking off. Then we found ourselves in this weird spot, where you have two products; one that’s doing really well, the other that you’re seeing the end, the end is near, but you have all these loyal customers who’ve been around, enjoy the platform, still like it. It’s just the technology underneath it that was the frustration of it, the changes of mobile, the changes with the way websites would work.

We got to this point and I realized, I’d love to see us continue Showit and reboot it. DJ at the time just felt it was okay to just let it go and put all our energy into pass. We talked through it and I said, “You know what? I think I’d enjoy taking on that project.” At that time, we split the company into two and he took over pass and I took over Showit.

Then even after that, it was another two and a half years before we actually had a product that we could launch. It’s easy to write a story and be like, “Oh, yeah. Then and then this happened and that happened. Now it all works.” If you look at the actual in the moments when I took over, I was taking over a sinking ship. I mean, every month was lower than the previous month, everything was going away, unsubscribes were up. It was hard to get people to stay on a platform that I wasn’t proud of that at that point.

I was like, “Well yeah. I mean, it works and we’ve made it the best we can with what we can. We made things still work, even if you didn’t have flash, we were still generating stuff that people could see and use and all those things. It still worked, it just wasn’t great.” I think that was the frustration for us of like, “Okay, how do we do this in the two years that we’re transitioning the company and getting a new product?”

Then even starting over from scratch and rebuilding and launching a product, you have all these features that you’ve built over the course of six to eight years and you’re like, “Okay, all those things need to be in the new product.” It’s like, “No, we actually have to start with a almost product, things that we’ve learned.” I think there’s even still things right now inside of Showit that I’m like, “Oh, man. We had that built out in the previous version.” We’re still working on building things out that make it better and better and better to design and use. That whole process of starting over is tough, but –

[0:20:42.8] DJ: I want to pause there for a second, because I think – I mean, to me it would be both tough and terrifying. I mean, you’re taking over a product that as you just mentioned, the revenue from it is lower and lower each month. It’s something that you’re not particularly proud of as it is, as it stood then. Certainly over the building process you were proud of it and just in general, you should be proud of it, because you’ve built something that thousands of people use, which is awesome.

Steve Jobs comes out, now it’s basically the death of a flash, right? You know that the platform’s going to have to change. It’s not the same as if I wanted to rebrand my photography business let’s say, and I can change my name and I can pick up with the same services, maybe communicate it a little bit differently and that’s that. That’s just not how developing tech works, right? You couldn’t just take what you had and build off of that. You were building a completely different platform. This is your full-time job, you have a family and just a plug for Elisa here, Elisa was on the podcast as well, her episode was at around episode 10, she talks about personality. Super interesting, so you should go listen to that episode.

Back to this, I mean, what made you want to take on this project, and just to paint the picture a little bit more, and I’m not sure exactly what the competitive landscape looked at that time, but I imagine that from 2006 when this company started to 2000 and we’re talking 14 now, around 2014, you probably didn’t have, or it looked probably very different; the Wix, the Squarespace, the thousand other builders that are out there. 2014, it’s going to be a much more crowded marketplace. Did you ever look around and just say, “I don’t even know if the market needs us anymore.”

[0:22:32.2] TW: Oh, yeah. For sure. I mean, that was the conversation that we had when we decided to split the company. It was like, look, there’s plenty of other options. The market doesn’t need you anymore. That’s definitely something that you’re fighting against and looking at it. I think what we came back to over and over again was that there was new platforms that were out there and there was new options and new availability.

This was the big bet. Can’t we compete with Squarespace and WordPress and Wix and other big players in the market? What can we do that’s going to make us unique? I really felt like just, and this gets into the tech side that people don’t always understand, but every builder that I looked at wasn’t really, what you see is what you get. It wasn’t really that where you placed something, it stayed.

It was responsive. Things text-wrap, things changed, this moved here, that did this, so you would design something, hit publish and then you’d open it up on someone else’s computer and be like, “Oh, what is that?” There’s always something different about what it looked like. That was great for the sense of responsive, but I was like, “Man, I think some of the things that we learned about building the first version of Showit never happened in the next wave of builders that were out there.” That was some of the ideas that we took with scaling. Instead of wrapping and rescaling like that, we actually took things and made it size up more similar to like if you took a jpeg and scaled it. It stays the same, no matter what size you’re looking at. It just might be scaled a little bit differently.

Understanding that there is a mobile design view and a desktop design view, but really being able to say people who care about the design are going to want the design to look like the design and those things. That was really the approach that we took that I feel like has separate us from the people around in the landscape. If you want to site up really quick, yeah, Squarespace is great and it’s going to prevent you from messing up.

Put it at the moment that you want to change what they’ve decided is how you should have a website, you’re going to feel stuck. That’s ultimately what it comes down to, unless you want to learn different coding things, or different – it’s just a lot more work to figure out how to change what they have. Whereas, we took the opposite approach. We said, “We’re going to provide hundreds of design templates now that are in our store, that you guys build design templates.”

We have great starting places, because design is huge. It’s important to start from some good structures and good looks and that. Then, you’re never going to feel it’s stuck. You have to get stuck in this box, or here, or there. That was really what we want to do after, and that’s where we’ve been going since then.

[0:25:19.3] DJ: Along the way, was there ever a feeling like this isn’t going to work? Did you ever have doubts like, “I don’t know. The ship is sinking.” In addition to that, a lot of what you just mentioned, right? I love that. I mean, I love that you love the tech behind it, right? When you’re explaining that to somebody, I don’t think that’s what is going to be like, “Oh, yeah. That’s why I need to be on Showit,” it’s because instead of the rap or doing the scale, there are so many reasons to be on Showit. How did you communicate that to your user base, or people that would become your user base? What was your strategy there?

Numbers are declining, how did you get people excited about this platform, or willing to give it a shot, especially after the old platform, it would just – I mean, it still exists obviously and it will for the next couple years, but eventually it won’t. It’s not as easy as publishing your old website to this new platform, because they’re two completely different platforms. What was your strategy in saying, “Hey, this is going to be way better than what it was. Stick with us. I know you can go to Squarespace, I know you can go to Wix, I know you can go back to WordPress and builders there, stay here.”

[0:26:34.9] TW: Yeah. Well, I think it’s a great question to explore and I think one of the things that I would encourage people come back to is that business is about relationships. I think that is definitely where we had to come back to and say, you know what, we need to – in the season of rebuild, we actually need to rebuild relationships, because there’s a lot of people that we had that felt burned by the fact that we hadn’t changed, or things like that, that we were stuck in this this way.

A lot of our focus during that time of building was actually building relationships as well. Going to leaders in the industry and just saying, “Hey, we’re sorry. We’re working on it. Here’s where it’s going. Will you be around? Can you give us feedback? How can we make this work?” There was a lot of that that was us just investing and being a part of the community again, really developing Showit to your community and saying like, “Hey, we understand that you felt neglected. We’re turning the tide on this. We really want to change what it looks like for us to have relationship.”

A lot of that had to change on the relational side, because until those things change, I think there’s a sense that some people have if you build it, they will come. I think those are few and far between that it really works out that way. I think a lot of times, really the relationships that are happening behind the scenes are things that – will be the things that matter. We doubled down, and as part of that split, we took over united conference and we really doubled down on doing a conference for photographers, and really investing in the community.

Even though we knew that most of the people that were coming to United at that time, or even using Showit, we just said, “You know, we’re going to do a conference for photographers that’s going to be awesome, regardless of whether they’re involved in Showit at all,” and build a community and hopefully when we have a product that we can really be behind that. Hopefully, they’ll come around as well, but regardless, we’re going to be invested in helping photographers succeed. That’s where really where we came back and started on that.

I mean, for sure, as we’re doing that, I mean, that was an investment period word. It was like, okay we’re spending money on salaries, we’re spending money on a conference, we’re spending money on all the things to make a company work, but I have no idea whether this is going to work out. We still haven’t launched the bridge that happens when you’re actually asking for people for money and they have to decide between X and Y and all those kinds of things.

That’s when you find out if your business is going to succeed. That’s where you can find out will they trust us with what we’re doing? That took a long time to find out that and our whole team will tell you about our first goal at the beginning of the year 2014 was a company goal of 50 first sites. I mean, that’s a crazy thing to think about now, but our only goal is that we have to get 50 sites online that are using the new platform.

We’re just begging everyone that we knew, like will you be one of the ones that’s a part of our 51st sites and say, will you be a part of this? We’re trying to get this launched by the end of February. We want to have 50 sites that are currently using the platform before we go to WPPI, so we have something to show and talk about and say, here’s success on the platform.

When you’re trying to get those first sites online, you find out all the things that go wrong, all the things that don’t work, all the things that you’re missing, and that’s when you’re iterating as fast as you can, because you’re like, we have to solve the things that prevent us from going to launch. Yeah, that was our big goal and I think we barely did anything. We’ve got 51 sites, something like that. It was like, everyone on the team, you got to be two or three people that you’re talking to and we’re going to do this and we’re hand-holding across the board. Everything was about that. It was like, “Can we get these first 50 launch?” Because that’s the make it or break it. If you can’t get past that just initial hurdle, you’ll never get to hundreds and thousands and whatever else that’s going to happen after that. That was definitely part of that journey of like, okay this is where it feels the ship either floats, or it sinks. Here we go.

[0:30:41.7] DJ: That’s fascinating. There’s a couple things that I want to dive in there, and I’m going to mention just so I don’t forget. The first one is features. In figuring out what features to build, because I think the comparable thing for people who are running a service-based business is people coming home and saying, “Hey, can you do this for me? Can you do this for me?” You’re thinking, “Well, I don’t really do that, but I could do it.”

Again, if you decide to go that route, the nice thing about standardizing things and serving the niche is that things are repeatable and that way you can serve those people really, really, really well. As Showit has done with the photography niche, right? People struggle with that, because again, it’s like people willing to give you money to do this service and you’re like, “Well, I need to pay my bills and this and that.” I want to get that in a second.

The first thing I want to ask about is investors. I mean, Squarespace for instance, right, has probably raised, I don’t know the exact amount, but I wouldn’t be surprised it was over a 100 million dollars, right? Do you feel like not having outside venture capital like that has allowed you to be more relational, has given you the opportunity to really focus on those first 50 people, right?

Something like Squarespace, I would imagine they have to, if they’re taking money from outside investors, they have to go out and grow and scale as quickly as possible. Whereas for you, I mean, you have a very clear goal and we’re going to go out and get 50 people on the platform and we’re going to serve them as best as possible and we’re going to ask them for feedback and we’re going to iterate from there. Do you think there’s any connection there?

[0:32:15.0] TW: Yeah. I mean, there’s a lot I could talk about when it comes to investment and taking money and all those kinds of things. It does change the conversation when you take on investment, when you have investors that you’re dealing with and you have to decide what you’re going to do with that. I actually have a book –

[0:32:32.2] DJ: Small. I think you’ve told me this.

[0:32:33.7] TW: Yeah, Small Giants.

[0:32:34.4] DJ: Small Giants, yeah.

[0:32:35.4] TW: Yeah, yeah. Sorry, I was just looking for Small Giants, and the premise of the book is when companies choose to be great, instead of big. That’s the whole premise of it. I think ultimately, as we’re growing Showit from the first days, I think the story I relate to people is that when your business is about survival, everyone’s on the same page. We’re just trying not to close the doors. When you get to a certain point though and you have any amount of success in your business, that’s when you can start to see when priorities of owners are different. What do you want to do with success? What’s the end goal?

I would say that too about investors. If an investor comes in and invest in your business, their goal is that you survive, so you start to make a return for them, but ultimately their goal with what they want the business to be about is going to be sometimes different than what an owner would want that company to be about. Reading that book, Small Giants was just such a great one for me to realize that there are companies out there that have said no to investing, that have said, no we actually don’t want to take that because we understand what that does to a business.

Now that’s given me freedom as a business owner to make the choices that I want to do, where I can say like, “Yeah, we’re going to stay focused on photographers. We’re going to stay in this niche. We’re going to run a conference that maybe doesn’t look exactly right on the books, but has the impact that I want it to have.”

[0:34:02.8] DJ: I’m feeling exactly right on the books means that it might not be profitable, is that completely for might not be profitable?

[0:34:11.0] TW: Well, you know any business that’s not profitable will ultimately die.

[0:34:15.2] DJ: Sure. The conference itself is what I’m saying. You said that – Yeah.

[0:34:19.3] TW: Yeah, for sure.

[0:34:21.1] DJ: It’s not like you generated a ton of revenue from this conference.

[0:34:23.7] TW: No, no, no. That’s not the point of it. That’s okay with us. Because we have priorities of what we want to do with certain things. Yeah, so I think when I was able to say, “You know what, I understand what I want my business to be about and I want it to be about the way that I can impact my team, the way I can impact my family, the way that I can impact the community and the industry, then I can have those priorities about what I want that to look like, without having to worry about is every one of these decisions going to be the most profitable.”

For sure, the baseline is we have to be a profitable company, or we don’t survive. We’re always working towards that, but to a certain degree, we have a lot more flexibility with what we want our impact to be, what we want the direction of our business to be, what we want it to feel to work at our company, what we want it to feel to be a customer of our company.

If for instance we take an investment, there’s no way we would have in-house support. It’s just so much more expensive than outsourcing that to another country. You’ll have an experience that’s very different, than the experience you’re going to have with our team, that is a part of culture that actually cares about the clients, actually cares that your website looks good and it’s going to go above beyond to try to take care of that. I would much rather be a part of a company that’s doing that, as opposed to squeeze that every dollar and leaving customers feel, “Oh, my God. Well, I guess they took care of my problem, I guess.”

[0:35:54.4] DJ: No. I think and to speak to the support team, because we certainly reach out to them quite a bit as we’re launching client websites. It’s not just a matter of like, “Oh, making sure something works.” They’ll go out of their way to make sure it works the way you want it to work, the way your vision. Like you’re saying, just making sure things are good enough, right? That’s something I really appreciate about them.

I do want to say just as a disclaimer here, the VC question, I’m not saying that all VC money is bad, or that all investor money is bad or anything like that, but I did based on previous conversations we had, I did have a feeling that you’re going to answer that way and I love that. I do love that distinction between what’s the goal, is it to have – or what impact do you want to have? Do you want to just get big, or do you want to have impact? I love that distinction and I love that about Showit for sure.

[0:36:45.4] TW: I am around a lot of friends that take VC money, around that environment. I understand it. I just know that there’s just different decisions that you’re making. I love that book Small Giants just for that purpose, is it helps you clarify these are those decisions that you’re making and it’s fine. You can go either way. I have friends that love the VC game and love being a part of just going as big as fast as possible. I just think the style of business owner that I’d like to be and the type of business I’d like to grow, I always want to grow our business, but not at the expense of losing those pieces.

[0:37:22.2] DJ: Sure. Going back to the feature question, I asked that, there’s a few pieces of that. I’ve interviewed Jake and Becca Berg of Dubsado and I sked them the same question, because again, it’s another company that I feel they definitely listen to the community and they definitely have a community around their product, just as Showit does. I’m just so interested in how you guys navigate adding features and figuring out what to build next, because I got to imagine that if you ask a hundred people for what feature they want next, 90 of them are going to say something different.

As the business owner, you have the burden of figuring out okay, people think they need X, but really they need whatever that is and I was wondering if you could just be too kind to that process of figuring out okay, how do you balance listening to the community, but at the same time not just chasing around features all day.

[0:38:14.3] TW: Yeah, it’s a tough question, because we’ve been through a lot of different seasons. We had feature boards that you could vote on and things like that. There’s all kinds of ways to generate input on what features matter to customers and things like that. Ultimately, I think what it comes back to is that you have to listen, you have to listen a lot and hear a lot of things. Then I think more than anything, you have to be a user.

I build a new site once a month just for the sake of feeling the pain points. I love helping a friend launch their site, figures that I get to feel all the pain points of getting a site launched and things like that. For sure, I think one of the big things for our whole team is making sure that we still stay in it, that we still are a part of it, and then we feel their pain. Our customer support team hears over and over on a daily basis the things that are pain points.

Then we have meetings with our team and say, “Hey, where do you guys hear it? What are the things that really surface from when you’re talking to customers and when you’re dealing with them?” I think a lot of it is our whole team has a voice on what is important, and then we’re also looking at where do we want to go. There’s features that it seems like, “Oh, that’d be cool,” but is that what we want to be, is that the direction that we want to go? There’s this other piece of being easy as an easier platform, trying to make things simplified that the more options that you give someone, the more complicated you become immediately.

Every time you feel like, “Oh, we’ll just add one more button here. We’ll just add one more thing here, you’re actually making it more and more complicated for everyone else.” We’re always trying to measure against those things like, “Okay, this might be a little bit nice, but is actually just going to make it harder for everybody else.” There’s a lot of that that we’re weighing when we say, “Okay. Yeah, let’s add that feature.”

What we found is that we try to provide some power features into the platform along with trying to stay fairly simple on other things. Even by just allowing a basic embed code thing, there’s so many things that you can grab from other places and drop in and extend. If there’s something you really need, you can find it that way. Also our choice don’t really try to stay integrated with WordPress, means that most plugins that you could get for WordPress will still work with Showit, so that provides all kinds of things.

Now, instead of saying, “Hey, we need to be owning that feature,” we say, “Hey, we’ll just work with someone who owns that feature.” When it comes to shopping carts, or download store, something like that, there’s all kinds of options that you can use inside of WordPress, that provide those features that we don’t have to be the expert on those particular things. We’re going to stay in our lane of like, we want to really provide this great design experience.

[0:41:00.4] DJ: Yeah. I think if people actually – I mean, those, like a shopping cart for instance, that is a product in and of itself and the layers deep that you can go with that. I think it makes sense, but at the same time I feel like I would really struggle being in that role, deciding what to do next and staying disciplined and saying, “Hey, this is our lane.” We’re really going to make this, stay in it and then make it as easy to use and flexible as possible. Because that’s the appeal of Showit, right? Is that we can tell our clients, “Hey, when we build you a website using Showit, you can update things on your own,”

[0:41:37.9] TW: Yeah.

[0:41:39.0] DJ: If you go ahead and start adding all these different features, then all of a sudden it becomes harder for people to realize, “Okay, this is what does that and this is actually how I –” Eventually, you got to a point where the amount of users on the new platform surpassed the amount of users on the old platform. Is that where you felt that you guys – at what point, I guess did you feel like “Hey, we’re on the right track. We’ve got something here.” Where you’re both proud of what you have now and feel like, “Hey, we’re heading the right direction.” You don’t feel like the ship is sinking. Was there a turning point, or did it just happen?

[0:42:25.1] TW: Yeah. That’s a good question. I think there’s a lot of moments along the way on that journey, because beginning of 2017, we actually we’re at this moment where we were starting to get to that point where we were losing money. That every month, we were losing money. It was like, that’s coming out of my pocket. I got to pull from savings, I got to stop paying myself, I got a whatever it is just to keep things going, because we’re growing. We’d launched in into 2016. We’re growing the new platform it felt like things were moving in the right direction, but at the same time, we were losing to a certain degree.

[0:43:00.6] DJ: How did you decide – I mean, so I guess the question before that question is in that moment, again, I just think like, okay, if I were going through this, you have a family. This isn’t just like, you have to put food on the table. How did you decide like, “I’m going to I’m going to keep going with this?” How did things were heading in the right direction, even though you’re losing money? Did you know that was just a season and things like, were other metrics telling you like, “Hey, we’re heading the right direction”?

[0:43:27.8] TW: Well. I mean, we were seeing good growth, good new subscriptions and new sites being launched, all those kinds of things felt good. It was a hard time, because you’re celebrating the fact that things look good now, things are picking up. The reason that we were able to stay in business is because an old product, but that old product is starting to sharply decline. You have a product declining and a product raising at the same time.

It’s a transitional period. Even if you may be growing, you’re actually staying the same revenue-wise and sometimes even shrinking. You’re finding out that you have to have people in place to handle the support, to handle all the stuff that we did with WordPress, that it became a little bit more difficult from a support end.

Then we brought on someone for marketing that we thought, “Okay, we need we need to invest in this, because we’re in a place where we have opportunity to grow. We really need to invest in the marketing side of this.” It was at that moment that we hired someone and we felt like, “Okay, we’re going to do this.” Then three months into that that we realized, “You know what? I’m paying out of pocket right now. I’m just losing money.”

We have the opportunity to be a profitable, stay profitable, stay fiscally responsible. At that time, I considered taking on investment. That was when I was really weighing, is this the season to take on investment. Then we said, “You know what? Let’s just be diligent about just being fiscally responsible,” so we ended up letting that person go and then just really tighten the belt and said, “Hey, we’re going to just be what we can be while we can be this and figure out how to make that work.”

That 2017 was a rough year. It was a rough year, because it was a good year, but it was a transition for sure and that made it tough to figure out how to how to balance all this celebration of a new product getting going, but also understanding that we’re not out of the red completely. I think once we got towards the end of that, then we realized, “Okay, now we can start to make some more decisions that are forward-thinking,” and that’s when we decided to move into an office space out here.

Because at the time that you’re losing money, you’re like, “I’m not signing a lease,” things like that. You’re like, “I don’t know if this is going to work out.” Yeah, so there’s a little bit of that where we’re patient about a few of our decisions and said, “Hey, we just got to let this go.” Even now, I think we’re finally hitting the point now where the old product revenue doesn’t account for the cost to run the current. We’re hitting that now. If you said like, “When did you feel like you’re out of the woods?” It’s like, “Yesterday.” It’s a journey.

[0:46:12.0] DJ: Yeah, I have two questions because we’re getting close to time here, but one, is during that hard season and I just want to preface this and I occasionally say this wasn’t in the outline that I sent Todd. I’ve been putting over the spot here for the last 10 minutes, but during that hard season where you had to make some of these hard decisions, whether it be letting somebody go, or deciding what direction the company was – whether you’re going to take outside investment, was there anything that you found yourself like, I got to imagine that there were people giving you advice. I would assume a lot of unwanted advice, and then how did you navigate that season? Do you have trusted people that you go to? What tips can you give people maybe going through a similar season and maybe obviously not the exact same thing, but how did you navigate that?

[0:46:58.7] TW: I think it’s really important to have people around you that are smarter than you. I mean, I know that’s a trite thing to say, but it’s really important. Honestly, part of this was I will always – I mean, since the beginning of our business, we’ve paid for consultants. We’ve always invested in people on the outside, being a part of our business and just not being in it, but on it and saying like, “Hey, are you running this appropriately? Are you doing this?”

I had advisors that were strongly encouraging me to take investment. They’re like, “Hey, you have this opportunity to do this. It’s going to work. Get investment and go.” I was listening to them and weighing it between different things. I don’t regret that. I think it was really good for me to be paying advisers, and not taking their advice, I felt like I learned what the ramifications were from both sides of what a decision like that would look like.

I think the other piece of that too is that leaders are readers and I think reading books over and over again, that’s another one that’s hard to come back to, but it’s like man, my book list is very long on which ones I’ve gone through and said, okay man, this has really shaped the way that I am able to do business and lead a company and do those things, because I invest time in reading. I listen to a lot of books, because I love audible. I’m a  lot more of an auditory learner, but I mean, I think yeah, I think I just go through books after books, because that and then the wisdom of others around you. Yeah, I have a team of advisers, leadership team here in our company and then my wife Lisa is one of the wisest people I know. Being able to –

[0:48:44.0] DJ: It’s true.

[0:48:44.5] TW: – bounce things off of her and she really helped me through that season too.

[0:48:48.7] DJ: Awesome. Well, the final question here and you were training for an Ironman, so completely not related to Showit here, but kinda. Why are you training for an Ironman? A 140 miles, right? That’s the total distance to the race. We were talking about this a little bit before. I was for whatever reason under the impression that is a little shorter than it ended up being.

[0:49:10.7] TW: Yeah. We talked about this at United last year. We had a card that we said do hard things. That might be as simple saying, do hard things, I think there’s something really valuable in that and I think even we talked about the story of what our transition look like and standing on the edge of a precipice and saying, “You know what? I’m just going to go for it.”

It’s hard. It’s easy to laugh about it later and say, “Oh, yeah. We just did it.” It was hard. I think there is a certain amount of that that I enjoy in life of saying like, “Okay, I’m going to put some challenges in my life that really pressed me.” When I was building the business, I just stopped doing a lot of working out and things like that, where I know that probably was a better time to be getting some exercise and things like that.

I really wanted to reset a bit there. I think in training for a marathon and other events in the past, I found that the moments when you feel like I have to give up, my body has to give up. Then your mind just makes the choice and says, “Nope. I’m going to keep going. Nope, I’m going to keep going.” Every time you make that decision over and over, it’s like when you’re lifting weights and you’re curling some weights and it’s like, “Okay, that’s as much as my arm can do, and then you do it one more time.” That’s going to strengthen your arm to push it past its capacity. It also strengthens your brain and I think that’s – the thing about I love the Ironman is when I go out on training and do a 90-mile bike ride, it’s like, you hit mile 80 and you’re like, “Well, that’s enough. I’m done.” You’re like, “No, I’m going to keep going. No, I’m going to keep going.”

I think that piece of training your brain to be able to say, “No, I’m going to keep going,” it creates this resilience. It creates the ability to face obstacles in life in other areas. I just feel this capacity to handle things more, just because of that training. That’s what I love about the endurance world is just how it changes the chemical makeup of your brain to be able to say, “No, I can handle enduring this.” I think there’s so much of life that comes actually from different directions and being able to just say I’m going to endure and I’m going to push through, that’s a big part of what life is about. Giving some free time to train to do something like that, I think is huge.

[0:51:26.7] DJ: Awesome. Well your first Ironman is coming up, right? This November, October. Yeah, so November. We will absolutely be journeying along when you get to that. I just want to thank you for your time and sharing your story. Even the challenging and the tough parts, which I know for me have been inspiring to watch and again, I think at the end of the day, we’re big fans of Showit largely because of you and the team behind Showit.

Don’t get me wrong. I mean, we wouldn’t recommend a platform to our clients that we didn’t think was outstanding. I also think the platform’s outstanding, but again, I think this is such a valuable piece of things for people to hear, because of just those things you mentioned throughout the interview, like having an impact instead of just getting big. Thank you for sharing all that and where can people find more about Showit?

[0:52:20.2] TW: Our website is showit.co. You can find us in Instagram @ShowIt.co. Yeah, you can sign up there. We have a 14-day free trial. You can check out the platform and see if it’s a good fit for you. I’m looking forward to seeing you, and hopefully in a few weeks we’re going to be taking an RV around the country and that’ll be part of this fun. We’re just showing up at your door one of these days.

[0:52:41.4] DJ: I think what Showit needs is a RV tracker. The kind of the Santa Claus thing around Christmas. You need a page on the website where we can go and find where you are in the app. Anyways, thank you so much for joining us and until next time.

[0:52:56.7] TW: I appreciate that, Davey. Yeah, thank you.

[END OF INTERVIEW]

[0:53:02.0] DJ: Thanks for tuning into the Brands That Book Show. If you enjoyed this episode, please consider subscribing and leaving a review in iTunes. For show notes and other resources, head on over to daveyandkrista.com.

[END]

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