<img height="1" width="1" style="display:none" src="https://www.facebook.com/tr?id=798947193590244&ev=PageView&noscript=1" /> Founders' Series: Jake & Becca Berg, Dubsado | Davey & Krista




This episode is part of the Brands that Book ‘Founders’ Series.’ This series will feature the founders and CEOs of companies that have created products and services for the creative industry.

Today’s guest are Jake and Becca Berg, the co-founders of Dubsado, the client management system for entrepreneurs. Dubsado makes any contracts, invoices, questionnaires, bookkeeping and other business workflows easy. I can confidently say that, because we’re now Dubsado users, but we weren’t before this episode.

Listen on iTunes | Spotify

I signed us up for a trial to prepare for the interview with no intention of continuing to use it. After a test run, I was hooked. One of the reasons that I wanted to interview Jake and Becca was because Dubsado seemed to come out of nowhere. As with most entrepreneurial journeys, Dubsado wasn’t an overnight success. It started small with very little functionality. Through many iterations, carefully listening to their user base and their own intuition, they’ve created an incredibly impactful tool for businesses.

Dubsado | Instagram | Try Dubsado (use this link to save 20% off your first month)

Resources Mentioned in this Episode:

  • Dubsado

Previous Episode: Todd Watson, Showit – Choosing Impact

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Founders' Series - Jake & Becca Berg, Dubsado | Brands that Book Podcast | Davey & Krista

The Transcript…

[0:00:06.5] BB: What people were just wanting that didn’t exist, which was the whole branding side that was when we launched it, we just said, “Hey, create your forms and make them look beautiful,” when other systems didn’t have that.”


[0:00:20.2] 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 part of the founder 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 are Jake and Becca Berg, the co-founders of Dubsado, the client management system for entrepreneurs. Dubsado makes any contracts, invoices, questionnaires, bookkeeping and other business workflows easy. I can confidently say that, because we’re now Dubsado users, but we weren’t before this episode.

I signed us up for a trial to prepare for the interview with no intention of continuing to use it. After a test run, I was hooked. One of the reasons that I wanted to interview Jake and Becca was because Dubsado seemed to come out of nowhere. As with most entrepreneurial journeys, Dubsado wasn’t an overnight success. It started small with very little functionality. Through many iterations, carefully listening to their user base and their own intuition, they’ve created an incredible impactful tool for businesses.

In this episode, we discuss their journey in building Dubsado, why they decided not to take outside funding like many of their competitors and how they created such a loyal and active user base. Be sure to check out the show notes at daveyandkrista.com for the resources we mentioned during the episode, and I’d like to hear from you about what kind of content you 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.

If you decide to try out Dubsado after listening to this episode, go over to the show notes for a code that you can use to get 20% off your first month. Now, on to the episode.


[0:02:15.8] DJ: All right. I’m excited to be here with Jake and Becca Berg of Dubsado. Dubsado is a content management system, I guess. Not content management system. A CRM for creative entrepreneurs, and I wouldn’t even say just photographers, or just designers. Although, I know that you guys have a ton of photographers and designers using your system, but it seems like just having been part of the Dubsado Facebook community for a few days now, that all sorts of companies use your system. Could you tell us just a second what is Dubsado all about?

[0:02:45.9] BB: Yeah. Like you said, Dubsado is a client management system and it just keeps track of sending invoices and questionnaires and all your bookings and just keeping the hub of your business in one place, so that you don’t have to be scattered around in a whole bunch of different systems. You can just keep it all in one place.

Yeah, and like you said, we have everything from doulas, to lawyers, to photographers, to coaches. It’s crazy and it blows me away how many different types of businesses use Dubsado.  I love, love when they chat us or call us. I’m like, “Ah, that’s so awesome. We have this type of person using the system,” so it’s exciting.

[0:03:22.6] DJ: Yeah. That’s awesome. I do want to go back and I want to hear all about how you all started Dubsado, how this idea came to be. Becca, I know that you previously were a photographer and not that you’re not a photographer anymore, but that used to be the business you focus on and I was laughing with Jake before this interview. I was on a phone call with him and I was talking about how I went to your website and noticed that you had plans on being away until mid-2017 working on another project. I just assumed that this other project is Dubsado. It was funny to me, because now we’re into 2018, almost mid-2018 and this project still has your attention. Something must be going well.

[0:04:01.4] BB: Yes, it is.

[0:04:03.0] DJ: How did this idea come about? Jake, were you also a photographer before Dubsado?

[0:04:09.0] JB: Before Dubsado, I was managing a retreat center just north of Santa Barbara where I just handled the day-to-day operations and I did a lot of the business side of things, coordinating the events that came through and signing contracts and sending invoices. I was doing a lot of the things that we do in the system now, except I didn’t have a system for it back then.

[0:04:29.5] DJ: That’s interesting to me, because you are – I mean, you created Dubsado from the technical aspect of everything, right? You built the initial product and I think now you have help doing that. How did you learn – you weren’t doing engineering for this retreat center were you?

[0:04:45.1] JB: No. I wasn’t. I was working there full-time during the day and then when I got off work, I’d be I’d be studying basically. Then Becca would visit me on the weekends and I was just there coding pretty much for my days off and I think it was pretty annoying for her at all.

[0:05:00.9] BB: I didn’t understand it.

[0:05:01.9] JB: I remember her asking like, “Why are you doing this? You’re coding for no reason,” because I was just doing test projects and I dabbled in starting a couple different websites to manage different aspects of our business at the retreat center, and I also built a couple websites for Rebecca to manage, I think it was a gallery that ultimately wasn’t very usable and it sucked. I did learn a lot just trying to get hands-on experience building a variety different things.

[0:05:33.5] DJ: You’re doing this and meanwhile, Becca you’re shooting. What kind of photography were you doing?

[0:05:39.5] BB: I was doing mostly headshots, because I also worked at my parents agency. They owned a modeling agency. I did a lot of headshots there. I worked with my parents, so I was doing two different things and trying to start up my own thing, which what I thought at the time were my headshots and dabbling into weddings while working at my parents agency. I didn’t understand what Jake was doing, or why he was learning that stuff and I’m glad he did.

[0:06:03.9] DJ: How did the idea for the Dubsado come about? Were you struggling with the organization, or management side of things?

[0:06:11.9] BB: It depends on who you ask. Who start –

[0:06:14.3] DJ: You know what, let’s start with you. I think, I’ve listened to some other interviews that you guys have done, so I think I have an idea of where this is going. At what point did you realize you needed a system?

[0:06:24.9] BB: When I started dabbling into weddings, just because I saw how multifaceted they were, how picky sometimes brides can get and I wanted to make sure that I had a contract down. I’d shot my first wedding without a contract and I was like, “Nah, I’m not going to do that anymore.” A few bad clients with headshots I’m like, “Okay, I need to get my contracts in place.” After I had my first contract wedding done, Charlie our youngest, well our youngest at the time, who’s our oldest now, sorry, confusing. He colored all over my contract and I was like, “Gosh. Darn it. I need to have this in a system. I’m just a disorganized person in that case, so I need this somewhere.”

I was like, “Jake, can you make something for me? I think it would be really great if I could have my contracts done online.” I looked at a few other systems that were out at the time, but nothing felt like my business and myself and I was really getting portrayed correctly through their platforms. I couldn’t put my brand in front of it all. I was like, “I want Jake to build it for me and it will just be mine. It’ll be my system.” He asked me and looked at me and was like “Come on Becca. I asked you to do this if we could do this two years ago you said no, this is stupid.”

[0:07:37.3] JB: Yeah, that’s the story.

[0:07:39.2] DJ: Two years prior, you had gone to Becca and said – I mean, you’re doing all this coding anyways. You had said, “Hey, I want to build a system for you to stay organized.” Basically she was like, “No. I don’t need this.”

[0:07:48.9] JB: Yeah. “Why would I need that? I have paper and I have contracts. She didn’t understand.” She’s like client management system that sounds so boring.

[0:07:58.1] DJ: As far as personalities go, I mean, I’ve talked to so many different husband-and-wife teams, I mean, Krista and I are husband and wife team. One thing I always love to get a feel for is who’s what role in that team. For Krista and I, I’m definitely the dreamer, I’m definitely the forward thinker, I’d be the one that says, “Hey, we should we should go out and build this.” Krista is the one that looks at me and is like, “Number one, we have a thousand other things going on. Number two, no. We’re just not going to do it. It’s not going to work or this or that.” Eventually, she comes around. How does that dynamic play out between you two?

[0:08:30.5] BB: Pretty much exactly like that. It really is. Jake is the one that is always pushing us, pushing me and pushing himself to do things, scary and into the unknown. I’m more the type person that likes to think about it a lot first. I don’t necessarily like to do something out of the norm. When he did come up with, “Hey, let’s start a new business and let’s do this,” it’s like, “No. That’s scary.”

Until I was like, “Ah, I actually need this,” and then I added a little niche to it, which made a little bit more sense, like the creative industry. Rather than, I think Jake just wanted to do a client management system for anybody. That didn’t make sense to me. I had to put it in my own hand. That’s how our dynamic plays out. He says something, months later I’m like, “Well, that sounds like a great idea Jake. Let’s do this.”

[0:09:19.5] DJ: That’s a really interesting dynamic to me, especially with Jake being the engineer, only because of the developers that we’ve worked with in the past. They’re generally more like Krista, in that they’re very much here focused, not necessarily the dreamer. They don’t necessarily have that dreamer personality. Krista is the one between us that has more of the development background. It’s really interesting to me Jake, that you are forward-thinking, always the one pushing people forward, or pushing your company forward and your relationship forward, because I just find that most developers are very much rooted in the here and now, and what’s practical, and what’s not.

[0:09:55.5] JB: Yeah. Even if when I’m in a moment where I’m trying to look forward and think everything out to a tee, there comes an extent too that where we plan it as far as we can imagine it and as far as we can conceive, but then we also do stay pretty tied into reality right now and we are very focused on the product that we have. I do expect my programmers to just be very focused on what we’re doing right now, and then they can leave the dreaming up to me.

[0:10:25.5] DJ: Sure. That makes sense. I definitely want to talk about how you guys even go about adding features and coming up with the MVP I think for a software product is so different than for maybe a service-based business. I don’t want to get ahead of myself here. Becca finally comes back around to you and says, “Hey, we need to do this.” What steps do you take to make this dream a reality?

[0:10:49.7] BB: When Jake and I heads come together, we laugh on how we just we make things happen. When he has the same idea, I have the same idea, we just get right down to it. Immediately, when we both looked each other, we’re like, “Yes, we both have this idea,” we start an Instagram account. We started building the website, we started getting those things in place literally that same day. We had the homepage done by the end of the day, so it moved rather fast there at the beginning and then development started. The ideas in the wheels started turning at the very, very beginning and then it just started the development phase of it.

[0:11:27.8] DJ: Did you guys just basically say okay – or Jake, did you just say, “I’m going to build something for Becca,” or did you all reach out to anybody else, or was it really like, “Hey, I’m I just want to look at your business and build something specifically for you. I think if I do that, it’s going to be helpful for other people.” How’d you go about planning who is this going to be for? I know Becca, you had mentioned Jake wanted to build just CRM for anybody, but you guys narrowed it into photography, or did you know right then? Because I know what ton of designers, especially that just rave about Dubsado. I know it works for other people, then photographers, and was that an attention from the get-go?

[0:12:04.6] JB: Yeah. I guess the balance is something that’s been where success is. Becca says one thing and I say another thing and then we just find the middle road. In my mind, I wanted to build something that was really universal and technically, that’s really challenging, because it’s harder to develop something that can fit and work in different ways. Whereas, if you just make something that it works this way and it’s going to work really well for the wedding industry, then you’re trapped in the wedding industry and development-wise, to go back and then add that flexibility, now your product is going to change significantly and you don’t know for sure if it’s going to work.

In the very beginning, we were debating between focusing on a specific community, or making it pretty universal. We just found compromises all on the way for what we thought would provide the most value to the most generic audience. Then I think, the creatives, the niche side of things was more towards the marketing of it. Because we knew that everyone is going to need to send an invoice, to sign a contract and send questionnaires to gather information around projects that they’re working on. We spent a lot of time preparing before we even code it very much. It was really, really hard. We were confused. It was like walking around in pitch-dark. We had no idea what we were starting, even the first day that I started coding in. We had vague idea and we’re just making steps toward that idea.

[0:13:31.3] BB: It wasn’t just for me though when he started it. We knew we wanted to create a system for people, but he had me in mind as the ideal client. He was building it for me, but we did have the intention to launch it to other people when it was done.

[0:13:46.9] DJ: Did you all gather any feedback in this phase, or was it really just among you two figuring out and planning what to build? What went into that decision like, “Hey, we’re just going to keep it to ourselves right now and build it and then put it out there.”

[0:14:02.7] BB: I am a pretty shy person actually. I didn’t even know, or even think to ask other people. I just was active and will ask a lot of Facebook group forums, and I was in a lot of those things. I was seeing what was not working for other people. I was doing my own research and taking in what I was seeing wasn’t working on other platforms that people wanted, what people were just wanting that didn’t exist, which was the whole branding side. That was when we launched it, we just said, “Hey, create your forms and make them look beautiful,” when other systems didn’t have that. We just focused on the things that we could do different and that was our market research was those awesome Facebook groups.

[0:14:44.6] DJ: I think there’s something to be said for that too though.

[0:14:46.2] JB: Yeah. I think we really focus on the marketing side of things.

[0:14:49.6] DJ: As far as feedback goes, I think something that entrepreneurs hear a lot is asking people what they think and getting feedback and the importance of feedback, but there’s a double-edged sword there I think as well, because people are going to give you all sorts of feedback and then it’s up to you to figure out what’s relevant and what’s not. I think the interesting thing and I alluded to this a little bit earlier about building software and correct me if I’m wrong, but when you build a feature, it’s not just that, “Oh, I can just build this feature.” You might have to lay groundwork for that feature.

If you build a feature, maybe it affects the future features that you add to the product. It’s not just as easy as saying, “Oh, you want that? Yeah, let me go build that.” It’s going to take some significant time and it’s going to have ramifications beyond just having that feature. How did you guys go about deciding, “Okay, this is what we need to have the launch and this would be maybe a nice to have.”

[0:15:45.5] JB: It was basically a big piece of paper that said this is everything that we could probably do by launch date. Then we just started taking a red pen and crossing things out, the closer to the launch date that we got.

[0:15:57.3] BB: When we did launch it, we looked back and we giggle at it, because it was basically just a system to store context. We didn’t have a way for our clients to pay their invoices yet. We had invoices, but not an online processor. We first did beta when we did our first launch. Then we got that that feedback. Okay, so they want to do credit card and ACH. Okay, let’s do that.

When we did our beta, which was about a hundred people in that first beta phase and just making sure that after we launched it, we took our next steps to actually full launch and they were in the right direction. That beta phase was huge and key, but it didn’t have a lot of features at all.

[0:16:40.9] DJ: How many people did you beta launch to?

[0:16:43.3] JB: We had about 300 on our list and we were only marketing on Instagram. That was the only form of just promoting ourselves and getting ourselves out there. It’s just creating a likeable brand and showing who Jake and I are on the Instagram page. We did that and we got him to sign up to our newsletter. Then we had about 300 people on that and then about a hundred actually sign up for the beta and use it, give us feedback, and that was so key. Those people, I still know who they are. They’re still with us. Still love them greatly.

[0:17:17.6] DJ: I think there’s such a value. I mean, for listeners out there, I think so many people get to launch and they’re super worried about it and they think everything has to be perfect. If I heard you correctly, when you first launched, it was basically a contact. It was basically a place to tell your contacts you couldn’t get paid online. I assume, were contracts a part of that? Could you send your contract for electronic signature?

[0:17:40.0] JB: Yes. Yes, that was –

[0:17:41.1] DJ: Okay. You could do that. I imagine that if we looked a bit back in time to that application. it would look very different than it does today, but you launched, you got feedback and then you iterated on that. From that point on, was it just a matter – you knew right off the bat like, “Okay, we need to focus on online payments,” let’s say. Or how did exactly which features to focus on from there?

[0:18:08.0] JB: Mostly just by how many people were asking for what feature. It was online payments customizing the e-mail address that it comes from. Instead of just a big Dubsado e-mail from sending from their own e-mail address. We had a few key core things that we know that we wanted to do, but we gauged what our users were asking for. Ultimately, we chose going with getting paid, because we want our people to make money through our system.

We went that route first and that was one of our biggest. The launch was a very, very hard time for us and me because I am a perfectionist and I want to please people and make them happy. I was afraid, since we kept using that red pen and crossing out all these things that we couldn’t accomplish because it was just Jake doing these things, I was getting really, really nervous that people aren’t going to like this. What are they going to think?

We’ve been hyping this up so much that it was going to be a great platform and it’s only going to have a few things. To my surprise when we launched, we still had people that liked it, that people – the things that we focused on that we wanted to do a little bit different than other people are what really attracted them to it. I just made up for our lack of features on the customer experience side of things and making sure that all of our customers if they did do a feature request, they were heard.

I whispered to Jake like, “Hey, this person wants this. How about we launch that in the next few days?” We put a little nugget out there and then that person would be so excited, then they go tell their people. I really just embraced every single one of our people to distract myself from we don’t have a lot and just make our people feel heard and loved.

[0:19:47.0] DJ: I should probably clarify, you guys weren’t doing this full-time at this point yet. I mean, this was in addition to the headshots and your photography business and then Jake, you were still working at the retreat center?

[0:19:56.6] BB: Yeah.

[0:19:57.7] DJ: At what point did you step down from the retreat center? At what point did you say, “Okay, I just have too much to do here and this is showing enough promise where I think I can step down.”

[0:20:08.2] JB: I remember the timeframe, but I remember the exact moment where I decided to do it, and I was in spin class. The hardest thing for me was my relationship to the retreat center, it’s very heartfelt and I love the place so much. My in-laws, Becca’s parents are highly involved there and I was helping them out a lot by taking on that responsibility. I knew that quitting was going to put a lot of stuff on their plate, but I also knew that it was really important that I had the time in my life to focus on our product that I was the only developer for at the time and it was hard at that point to balance new features and bugs and all this stuff when I was still working with clients and all these different things with the retreat center.

Luckily, we had compensated ourselves through Dubsado to allow me to leave the position. There I was spinning, sweating and I just decided to text my boss and said I was leaving. It’s been in class while spinning and I think –

[0:21:11.2] DJ: This happened literally in the class. It wasn’t like, “Yeah, I’m going to get off this bike. I’ll go home and chat with Becca about this.”

[0:21:17.6] JB: No. I was spinning. He texted back. He was like “Okay, why?” I was like, “I’m just working on other things in my life.” Then spin was over and I felt amazing. I just felt free and I think it’s always important to really take your time with decisions like that and not be selfish with it. I didn’t do it for myself necessarily. It was best for everybody and I just said a prayer before I did it that everything would work out with the retreat center and obviously, praying that Dubsado was going to be able to sustain us, because I just left my full-time job. I did it and I owe it all to spin class.

[0:21:57.3] DJ: Do you still go to that spin class?

[0:21:59.5] BB: I do.

[0:22:01.2] DJ: Yeah. I was going to say – I mean, if it was – maybe that’s just where all these great ideas are, you know something about that spin class. From the time you guys had this idea to the beta launch, about how many months, or years, or days was that?

[0:22:16.0] BB: It was five months. From the point of idea to beta launch was five months. In that five months too, we also had our second child. Busy with work and other things. Most of those five months were dedicated towards planning. I was wondering why Jake wasn’t working on it and programming, because I don’t understand the programming world. I’m a little bit more keen on it now and understand it a little bit, but it was a lot of planning and a lot of planning dates. It wasn’t until about, what was it? Three days before?

[0:22:50.3] JB: Yeah. 80% of the first product was built in 72 hours.

[0:22:55.5] DJ: 72 straight hours?

[0:22:57.2] JB: Yes.

[0:22:57.5] BB: Straight.

[0:22:58.4] DJ: Were you working against a deadline? Did you did you announce the launch date and that’s why you had to get it done in those 72 hours?

[0:23:06.0] JB: Yeah. We had announced it two weeks prior to actually launching. then three days before, we looked at it and we’re like, “This isn’t really doing anything yet.” There were some guts there, but that you couldn’t sign a contract, you couldn’t build a format on, you couldn’t send an invoice.

[0:23:23.5] DJ: It sounds like pretty much the entire application.

[0:23:26.0] BB: The whole thing, right?

[0:23:28.6] JB: Yeah. Becca would text me every now and then. She tried not to bother me too much, but 24 hours day and I was like, “Becca, we’re not going to do – we’re not going to receive payments. We can’t connect the stripe. I can’t do it in time.” In those 72 hours, I think 48 hours in I started getting a little bit crazy.

[0:23:47.9] BB: I’m really glad those 72 hours were one of the most important parts of Dubsado’s history. We learned so much from that 72 hours. One, never do this ever again. Deadlines are something that we need to set better. We learned a lot during that period of we need to be better on ourselves and not treat ourselves this way. It was a growth period, we still had a lot more. A lot more to learn and we still do, but we learned a lot from that 72 hours.

[0:24:18.8] JB: It’s important to set a date too at the same time, because we were just lollygagging and planning and going forward, but without a set date, maybe it would have taken another month, another two months. We just needed to go for it and do it, instead of just sitting around thinking about it.

[0:24:36.8] DJ: Yeah. I definitely think there’s a tension there in not holding yourself to a standard that’s unfair, and at the same time, having deadlines. I think so many people – I think, you’re such a great example for so many entrepreneurs about chasing after an idea, but then not being scared to put it out in the world, even if it’s not perfect now. Because if it serves at least a couple people well, which it sounds like it did and it probably was better than a lot of people’s paper and pen system, where their kids are coloring all over their contract. From there, that’s not the end. That’s just the beginning and you guys have certainly iterated from that moment on.

From your beta launch, how long did it take for you to leave your job and make this your full-time priority about? When that spin class happened, was beta launch over and you guys had launched it to the world by then?

[0:25:31.1] BB: It wasn’t when we launched it to the world. We launched it to everybody in February of 2016. It wasn’t until August of 2016 that Jake actually quit his job. We had full launch and we were still both working heavily. I didn’t actually stop working with my parents and doing headshots until, I want to say it’s just been a year, like we just hit our year mark with it. I waited a very long time, because I was still making money and I wanted to be sure when I left, we were literally all on our own.

We held out and made sure that we were stable in Dubsado that we can support ourselves, support our team that we were going to hire, because we always had intentions of hiring a team, and we could support ourselves, we can support our kids, all of that.

[0:26:20.7] DJ: As you started growing, I mean, customer support with software especially, it’s not like you just launch – I think that’s too the myth around building software. It’s like, “I built this thing. Now I just get subscribers and I kick back, just at the beach or something like that,” when in reality you guys are dealing with bugs. You’re making sure things are working correctly. Things happen that are outside of your control probably, because you rely on other vendors for your application to work. I remember when Amazon had that big outage, half the internet was down, because Amazon is down, but people were probably coming to you being like, “Hey, what’s going on?” I’m just impressed that you guys were able to manage that and working and not to mention, having a second kid all during that time period.

In addition to that, especially when it comes to developers, although you were doing most of the building, or Jake you’re doing most of the building at the time, building applications can be expensive. It’s not like you have no competitors, right? Of your competitors, most of them it seems have taken outside funding to the tune of millions of dollars. You’ve had VCs come in, venture capitalists come in and inject millions of dollars. At any point during that, was that intimidating? Were you guys even looking at what else was going on, or what else was out there, maybe what situation their company was in and was that intimidating to you guys as you were building Dubsado.

[0:27:45.4] BB: We knew that our competitors did have funding. We saw what it was doing to them. Basically, what I saw in the Facebook groups on how some users were unsatisfied with how things were happening, or features weren’t being launched. I was like, “Jake, I don’t want to be that stuck. I want to be able to if someone needs something, let’s get it done. I don’t want to report to anybody. I don’t want to have to be advised if our company should go in this direction.” Our main goal with not being funded is just being able to pivot, being agile in our own business, so that we can release the features that we want to our users when they want them.

[0:28:26.1] DJ: Yeah. I guess that makes sense, because the first people that those companies are responsible to are their VCs, their investors, right? Not necessarily their customers. Whereas, you all your first priority is what your customers want. Did you ever even consider outside funding for Dubsado?

[0:28:45.0] BB: No. That’s something I’m always like, “No. Never.”

[0:28:49.8] JB: It was a big victory when we got our first e-mail from a VC saying, “Hey, I’ve heard of you guys. I’d like to talk and see if we can work something out.” It was validation for sure.

[0:29:02.4] DJ: What do you think your main differentiators are between you and some of these competitors? Outside of, I mean, A, they have to be responsible to VCs and you guys can just be responsible and hear your customers.

[0:29:16.2] BB: Yeah. I think, our agility is number one. Being able to – one thing that we’ve always held at the front and I’ve mentioned this a few times, it’s just the branding and how and especially with just a few features that we’ve launched is your company’s branding is on everything. You can run Dubsado and not have Dubsado’s name in any little link, in any form, nothing.

We noticed as we were building Dubsado that this was a huge thing that people didn’t like. They didn’t want to see their clients see what company they’re using to send their contracts and invoices. They wanted it to feel like their business. We noticed our competitors aren’t doing that too much. If one of them is, it’s hard to get it configured and set up at everything.

[0:30:01.1] JB: Yeah. When we when we first came on the scene, that was one of the biggest changes that we saw in the market, because a lot of them competition-wise were heavily like, “This is our brand. It’s not yours. Here’s our logo on the invoice.” I think they may have been using it as a form of marketing for their own service and then we came in and it would – even though there were still room for improvement where we could remove ourselves from we were doing a really good job at just making it our customers and their brand alone. That was one of the first changes that we saw in the market when we showed up on the scene.

We were just talking earlier about how that was one of our big moments where we knew that things were working out for us, was when we saw our features being mimicked by other companies that are really well-funded, and to see that such small statured company could have an impact where someone in a big successful environment like that said, “Hey, look at what these guys are doing. We need to do it better.”

That’s when we knew that we were doing well, because we’re pushing the market forward. I think, it got a little stale and I think it got a little bit set in their ways and then we got the chance to come in and shake things up a little bit, and I think that ultimately works out for the best for everyone. It pushed us to do our best when we saw another company copying our style and/or coming out with a feature that we had and we said, “Okay, well we see you and we’ll raise you one and we’ll come out with something that you won’t be able to put out for another six months,” because we are so agile and because I know every line of code and I know that I can do 10 features in a week, because I know how all the pieces fit together.

I can see a few moves ahead and knowing that these things aren’t going to mess us up in the future. We don’t just act and we have a plan and we know that these pieces are going to matter in a few weeks. Because we don’t have this environment where we’re reporting to people, or because our designers are dissociated with our engineers, everyone is very fluid and we’re all on the same page in how we communicate. We mimic our early days in Dubsado with what we do today. We’re like street fighters almost. We always come on fighting and we’re always –

[0:32:30.4] DJ: Is that a new marketing tagline?

[0:32:32.1] BB: Yes. We like it.

[0:32:34.0] JB: Yeah, we’re always fighting.

[0:32:36.2] DJ: What’s incredible about what you’re saying is I think again, a misconception that people have is the more money you have, the more resources you have, the easier things are. In many ways, more resources just means a greater ability to become more distracted. Whereas, when you have fewer resources to start, you have to be very careful I think about dedicating time and resources to any one thing. It causes you maybe to think a little bit more about the decisions that you want to make.

The other thing that’s interesting is while some of these companies are big, or in that result in more people, that’s not necessarily better, because you guys can turn around and like you were saying, you can decide in a day, “Hey, this feature is our priority now.” You don’t have to go justify it to any executives. You don’t have to justify it to different members on your team to get it done. You can just go and make it happen.

I think that there is real value to I mean, just to how you guys started, just how you started your business and how you lean into those strengths and how you are really responsible to your customers.

One thing that I want to mention to you guys, and I should say right now is that I receive no incentive for doing this interview. I reached out to you guys. I actually tried to track you guys down for a while and I’ve told this to Jake, because one of the most fascinating things about you guys is more and more, it almost seemed like overnight to me, although I’m sure it didn’t seem like overnight to you guys, is when people posted online in different industry Facebook groups, “Hey, what CRM do you guys use, or what do you use for contracts and invoices?”

It used to be, you’d see the normal players a lot of these companies that we’re talking about that are bigger and receive funding in a snap, but the more and more I saw Dubsado show up, and then all of a sudden it seemed like, that’s all I saw. Dubsado. I love Dubsado. People are going on, “I don’t even know how I ran my business without Dubsado.” One thing I also noticed was that people would talk about, “Oh, I switch from this platform to that platform,” and people would land on Dubsado. I’ve tried five other platforms and then I got to Dubsado and this is the one.

I haven’t to this day – I kid you not, I have not seen anybody say, “Oh, I tried Dubsado. It wasn’t for me and I went to the 17 hats or something else and that was better.” It seems like people really love Dubsado. What do you credit just this – I guess these intense fans to? Is it the features, is it the customers, or it’s a combination of things?

[0:35:09.7] BB: It’s definitely a combination. I have always said to Jake, it has to be customer support. People just want to feel heard. People want to feel like they belong to something. Especially too at the very beginning, I knew since we didn’t have a lot, I sent out thank you, welcome gifts to our users as well.

You want to make people know that they are appreciated and you get them falling in love with your brand, the people behind the brand and everything about it and they start to feel involved in it. They’re part of the system. All our users who are here, they’re part of Dubsado. They helped create Dubsado with any feature requests that they have made. It’s just about making people feel that they are a part of something, and it’s helping their business too.

[0:35:59.8] DJ: How did you guys go about – I’ll say, one of my favorite piece of software is Slack. You guys know Slack?

[0:36:04.7] BB: Mm-hmm. Yeah.

[0:36:06.3] DJ: Krista and I, we have a three-person team. It’s not big. Krista and I use Slack to communicate with one another. What I love about Slack is that big companies use it, right, and find a lot of value in it. Even a two-person team like Krista and I find a ton of value in using Slack. I feel like I’m getting a lot out of it. It doesn’t feel feature-heavy, like Evernote. I don’t know if you guys ever use Evernote. If you currently use Evernote, I’m sorry for saying this, but to me, I used to use Evernote, but I always felt I was only using 5% of it. Because I only felt I was using 5% of it, I eventually got rid of it just because I felt I wasn’t taking advantage of all it had to offer, so I went out and found another solution.

We’ve recently tried out Dubsado, not necessarily with any intention of switching, but it looks like we are. We’re going to start using Dubsado. That’s one thing that struck me right off the bat was I just wanted to get in there and try it out in advance of this interview, just so I could be more educated with the platform. One thing that stuck out to me right away was even if I were just to use it for contracts and invoices, it was super easy to get it set up.

One situation where I just had to send a contract real quick, there was no invoice associated, it was paid via our accounting software already, and I could do that. I didn’t have to fumble around with setting an invoice to zero just to be able to send a contract. How do you guys manage that with all the feature requests you get? I know you get a lot and you have this great community on Facebook, which on one hand, I’m sure it’s great to have that community. On the other hand, I’m sure sometimes you’re like, we really can’t. Of all the reasons I mentioned earlier, we can’t focus on it right now. How did you guys manage that, focusing on making it useful for a lot of people, but then also being feature rich, but not to the point where it felt like just this monster of a product?

[0:37:53.0] BB: I think a big thing was we have our master list of things that we know that we want to accomplish, to make sure that we’re at a steady place in the market, make sure that we’re doing well there. Two, if those features that people ask either build up to one of our goals that we have, or a building blocks to it, we’re going to go ahead and get it done, because it leads to the next thing. We just take into account with what people say to what do we have and how could we maybe tweak it in there.

There are some people whose future requests are so, so, so specific and might not necessarily work with our goal with Dubsado. The way you can use Dubsado is so flexible that if you want to do something that Dubsado entirely isn’t meant for, you can have a workaround for it. There are many, many ways that you can do just one thing at Dubsado. You can send a contract with a proposal, you can send a contract by itself, you can add a contract to a client portal. There are just so many ways to do one little thing, that it can pretty much work with any type of way you’re trying to do it.

If we can’t do something for someone, we sure try our best to make sure that they can do what they want to do in another way that we can do something. We just have our master list of what we can do and try to use people’s features and build that to master list up.

[0:39:15.8] JB: I think a big part of building our core product, we made some design decisions early on that everything was going to be one click away. There used to be one of our big rallying points when we’re talking with someone, or selling the software is like, you can find any piece of information in 1, 2 or less clicks. Click onto the job, you can see the contract, you can see the invoice, everything’s going to be there.

Eliminating the extra thought process of how do I get to something, how do I add something. Focusing on being simple, that there’s only one place where you can add a contract to a job and there’s only one place where you can send an invoice is an example of eliminating a possible confusion point. When we build things, we might end up in a situation where we developed something that might be a little confusing. Then, we really self-analyze and decide, “Okay, that isn’t really working, so let’s pull it apart again and let’s go back and let’s refine things a little bit.”

When we do add things, we’re keeping simplicity in mind. Then we also have the retrospective to look back and say, “Okay, this isn’t working. Let’s fix it. Let’s improve it and let’s go the other direction and simplify what we already have.” We’re simplifying both directions, where when we make new features, we’re simplifying something for our user. We’re not just putting something in there like a Band-Aid, or just sticking it somewhere it doesn’t belong where everything is very intentional.

[0:40:48.4] DJ: Yeah. I felt even as I was setting up Dubsado, I really didn’t have to use any of the help articles. I’m also the person that’s just going to go in there. I mean, and there’s tons of them available if you need them. I think that speaks to how intuitive it was to set up. The other thing I did which I generally don’t recommend to people is I just sent our first contract and an invoice using it without even looking – without sending a test, without looking at how it would look on the other side. I was so –

[0:41:13.8] JB: Awesome.

[0:41:15.0] DJ: At the end of it, it looked a e-mail that I would send from my business Gmail. It looked like it came from – it didn’t have – I know you guys, you were big on this and you had mentioned this earlier in the interview, didn’t have Dubsado at the very bottom. The links weren’t your brand. If I put in a button, I know that’s an option, but I didn’t, but it would be the brand colors that I set in the settings. That’s awesome. We found it super easy to use.

[0:41:43.7] JB: I’m so glad you had that experience with it.

[0:41:46.2] DJ: Yeah. It’s been great. Like I said, and just to reiterate to our listeners, didn’t know you guys prior to this this interview you’re just a company that I admire from afar, and I just find myself I think attracted to this company. Husband-and-wife team, you guys do it in yourself, you’re in the foxhole with your clients. You really understand their struggles in building a business and then also, you have that added advantage of Becca, having been a photographer and trying to build this photography business, being in this freelance world, understand I think and empathize with people also going through that. I love companies like that.

Showit I think is another one that I can’t say enough good things about. You guys, so transition you real quick and this how we’ll wrap-up. You guys have had the opportunity – you have thousands of users now, which is incredible, so it just seems like you guys continually are growing at this just as fast pace, and again, just posting those Facebook groups, it definitely seems that way. I got to imagine that you get to see some interesting things, just in how people use the program. Among your high performers who use Dubsado, those people that just seem to be really crushing it in their businesses, how do those users use your platform to grow their businesses? What are the things that have should have stood out to you it’s like, “Oh, wow. They’re doing that and that’s had this result.”

[0:43:10.8] BB: The people, the high performers and the people that just really dive in and use Dubsado, that’s exactly what they do. They dive right in, they get their stuff in and if they have a question it’s like, “Hey, I’m trying to do this. What can I do to make this happen?” It’s more of that attitude, let’s make this happen and you’re here to help me, so let’s do it. I’ve learned a lot from those people in how they use the system.

I was doing a webinar and she posted in the chat, she’s like, “I made an extra $12,000 this month that I didn’t expect to make just because Dubsado’s proposals made it so easy to have my clients just choose little add-ons and then it just added up the price.” I was like, “That is awesome.” Now, since that power user gave me that little snippet of information, I’m now passing that along to everyone else in my webinars and everything. I learn things from them and what the hell they’re using it, but they’re definitely go-getters and come up with amazing ideas on how to use Dubsado on their own too.

[0:44:12.6] DJ: Yeah. I mean, that’s incredible, just in – Again, it speaks to – you if you make things simple for people and they’re not overwhelmed with decisions, good things generally happen. We have an album sales template. We try to – we use kits for our albums and we used to send them a PDF. It was mostly text on their options and there’s a billion options. As soon as we simplified that, made it more visual, added it to our website and just said, “Hey, go down that.” It’s just simple choices. All of a sudden, we found that more people were ordering albums. It wasn’t that they’re more interested in it now, now the decision is easy so they’re not choosing from a thousand different colors. We’ve narrowed it down like, “Hey, here are the ones that people are most happy with.” That’s great. Anything else?

[0:44:52.4] JB: Just in general and when people are not negative, they’re positive and they’re focused on how can we do it, instead of saying, “Oh, it’s not possible. Why can’t I do this?” It’s being more creative, it’s being – it’s having a general sense of positivity about the way you carry yourself.

I mean, I’ve seen a lot of people make a lot of money, but it’s the people that are positive that are satisfied with their life and they’re having fun with what they do and I think that’s the true point is just being able to enjoy what you’re doing.

[0:45:26.2] DJ: Yeah, yeah. Well, thank you for joining me today. We’ve had a great experience with Dubsado. I hope that a lot of people check you out. Where can people follow along if they’re listening to this and like, “Hey, this sounds like I need this in my business because I’m disorganized, or my current platforms not doing it for me,” where should people go?

[0:45:44.1] BB: Sure. They can go to our website dubsado.com. D-U-B-S-A-D-O.com. Or our Instagram is MyDubsado, which we just have a lot of fun on.

[0:45:55.1] JB: Our place is going to be the YouTube though. I’d send everybody YouTube. Our channel is just Dubsado and you can follow along with the office shenanigans and see the trouble that we get into on the office. On the vlog this week is going to be really good. I’m really excited for it.

[0:46:10.2] DJ: Okay. Awesome. You guys have a podcast as well.

[0:46:13.0] BB: Yes.

[0:46:13.4] DJ: Right?

[0:46:13.9] JB: Yeah, The Creative Leap. You can find the link to that on our website. It’s thecreativeleap.dubsado.com.

[0:46:19.7] DJ: I listened to my first episode a couple days ago. I think it was the one with Gavin Wade from Fuzzbot and I thought it was great. I thought whoever host that does a great job, ask great questions. Really well done.

[0:46:29.7] BB: Yes. You love Alex.

[0:46:31.2] DJ: Yeah. Head on over there and check him out. Thank you all for joining me.

[0:46:35.1] BB: Thank you so much for having us.

[0:46:36.6] JB: Thank you.


[0:46:40.4] 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.


Founders’ Series: Jake & Becca Berg, Dubsado An Interview with the Cofounders


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