Ep. 004 | How to Create Human-First Technology with Dubsado Co-Founders

Apr 25, 2022

Where you won’t find trendy business tactics, but you will find truthful insights and timeless stories from leaders to look up to.


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Ep. 004 | Curate Conversations With Pia Beck

“There is a lot of power in just listening to your user. Your company wouldn’t be anything without the people that use it.” — Becca Berg 

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In this episode, Pia interviews Becca and Jake Berg, husband and wife co-founders of Dubsado — our favorite CRM at CWco., and probably yours too. 

Dubsado’s motto is: More business, less busywork.

Dubsado helps your business stay in motion: Build relationships, schedule appointments, and create workflows to streamline your projects from start to finish.

We use Dubsado every single day, so it was cool to get to chat with Becca and Jake about how they’ve built the company over the last 6 years. 

In this episode, we talk about their main measure of success as a human-first tech company, how they almost exclusively focus on what their users want and need to drive their evolution (they even have a public roadmap you can see on their website of which features are coming next), what they did to create more with less and grow their business, why customization sets their software apart, and the pattens of life as an entrepreneur. 

Hope you enjoy!


Links mentioned in this episode:

Special thanks to our sponsors, Parker Clay (code CURATE15) and SeaVees (code CURATE20). Music created by Queentide.



 [00:00:00] [00:01:00] In this episode, I get to interview Becca and Jake Berg, husband and wife co-founders of Dubsado, our favorite CRM at Curate Well Co and probably yours too. Dubsado’s motto is more business, less busy work. Dubsado helps your business stay in motion, build relationships, schedule appointments, and create workflows to streamline your projects from start to finish.

I used Dubsado every single day our team does too. And so it was so cool to get to chat with Becca and Jake about how they built the company over the last six years. In this episode, we talk about their main measure of success as a human first tech company. How they almost exclusively focus on what their users want and need and use this to drive their evolution.

They even have a public roadmap that you can see on their website of which features are coming next. What they did to use what they did have to create more with less and grow their business. Why customization sets their software apart [00:02:00] and the patterns of life as an entrepreneur. Hope you enjoy.

This podcast wouldn’t be possible without our sponsors. Let’s hear from SeaVees.

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Whenever I buy products, I’m looking for those that make me feel more like myself and make my life better in some way. [00:03:00] SeaVees are 100% that for me. Use our code CURATE20 for 20% off. When you shop at SeaVees.com.

 Becca, Jake, thank you so much for being here with us today. I am so excited for our conversation. 

Ah, thank you so much for having us. We’re very excited to be here. 

So the first question that I always like to ask is in your own measure of success, tell us about your growth at Dubsado. This could be number of users.

It could be feature development, team growth. I know you just moved into a new office. It could be an ethos that you’ve grown your team off of whatever you want. 

Yeah, I think, I mean, so we’ve, we’ve grown a lot since the very, very beginning of Dubsado. It was just Jake and I working on the team. And we’ve definitely had growth in terms of, team size, growth, office size growth, and those are all really great things.

Really great to look back, to see where we were before and where we are now. Uh, but one thing that helps us measure our own success and something that we really look at is making sure that we are better than we were the day [00:04:00] before. We don’t for a software company and for, for being in this industry, you know, whole bunch of data gets thrown around and whole bunch of numbers and KPIs and things like that.

And whereas that is great in its own area and great to use. Our metric that we like to use, like I said, is just being better than the day before. And if we can continually be better than we were the day prior, then we can know that over a month, that adds up over a year. That adds up. And for us being six years old, it has added up over time and we’ve just progressively gotten better. 

Love that. And you just celebrated your sixth birthday, right? Congratulations. That’s awesome. 

Thank you. 

Yes, it’s definitely come a long ways from Jake who is rocking a baby on the Starbucks floor while he was programming Dubsado in Starbucks, right? Jake? 

Yeah, I think it’s easy to compare raising children to raising a business.

 Like our [00:05:00] businesses, potty trained. We’ve had many sleepless nights cause the baby would sleep. Yeah. 

I love that analogy. Tell us more about that. What is like, what does that look like to potty train your business? 

I knew I regretted that example as soon as I saw it on my head was just, I had to get it out.

I guess it’s just. It’s about figuring out sort of what problems we’re hoping to, to work on as, as a team and really look forward to see what’s coming and make sure we’re all on the same page as, as much as we can. Um, and then when those things do come up, we’re like, Hey guys, this is what we’re working towards.

Everything’s good. Let’s you know, work on it and whatever it is, in contrast with maybe when we’re, uh, you know, infant, it was. One or two people responsible for like very, a lot of different things. So it was like, okay, well I’m one person. I have 10,000 things I have to accomplish. And I had, like actual babies at home.

And you’re just like tackling one problem then here and another one pops up over here. [00:06:00] So I think, yeah, I think when it comes to the toddler, it’s a little bit more, a little bit more stabilized and just more balanced. 

Yeah, absolutely. We’re kind of in that transition right now at Curate Well Co where we’re going from a very small team where there were three people responsible for everything and, and more generalized responsibilities to starting to really create swim lanes and having people be responsible for fewer things and going through potty training process. Which I understand why you were granted that example, but I think it’s perfect. I think it makes so much sense. So I love that you brought it up. So there’s a snippet on your website that I would love to leave, read out loud for our listeners and then have you all unpack a little bit for us.

So on your website, it says, when you provide feedback about how a new feature or update could improve your life, you’re reaching decision-makers. There is no red tape nor any bureaucratic steps between hearing your suggestion and implementing it. Our goal is to communicate with, and listen to you just as intentionally and openly as we do our own team.

Why is this important to you?

 [00:07:00] I think this, this goes along with us being self-funded as a software company, that’s definitely something that is rare. Cause it’s much easier to accept money and a lot of it and go for it and run full steam ahead. But something at the very, very beginning of Dubsado that we wanted to do a little bit differently is really focused on what our users needed.

And if we grew upon that and what our users needed and our user base. Then we would ultimately be that tool that everyone goes to for their business. We become their business hub. So that was kind of our deciding factor on whether we should accept funding or not, because. Without funding and being bootstrapped, we are able to see something pop up in our Facebook community and talk about it as a team and within the next few weeks implement it. Or change a course or a roadmap because things have been popping up and not have to report to a board of directors, not have to.

 Run it [00:08:00] past other people it’s does this work for the Dubsado future and the team and its users? If yes, then what’s full steam ahead and maybe pivoting and changing some gears. And that was the key to our growth, especially at the very, very beginning. People were noticing that they were saying things it would happen.

They would do a feature request. It would happen now. I mean, definitely it’s slowed down because now a bigger company. We’ve definitely have our paths that we’re on and such, but still if a user comes in and has, has a problem, that problem gets right to a developer. And it starts getting worked on. So yes, still things are and users are being listened to, and feedback is taken into account.

In fact, every single feature request that comes into Dubsado is literally looked at with two real set of eyes and by a human, like it’s still, we still have that same. You even though we’re a little bit bigger now. 

Yeah. And so how have you maintained that as your business has grown? Right. You’ve you have a team of over 55 people now [00:09:00] that you’ve grown over the last six years, how have you maintained that intimacy and open line of communication with your users as the company has gotten bigger and, and maybe, you know, you or Jake, have you gotten a little bit farther or from like interacting directly in that Facebook group?

 Yeah, it’s we, we have some great leads who are able to spearhead in different areas. So we have our education department who is Cameron, and he talks a lot one-on-one with our users, whether it’s in one-on-one calls or doing webinars and speaking to them. So they’re actually getting a live Dubsado person, who reports to me. And we’re able to make decisions from, from things that come up in his calls. Then we have our product department and the person who runs our product department is the one who heads up our feature request board. So people can go in and, and email us a feature request or out a vote to our, we have our [00:10:00] roadmap listed publicly.

So where Dubsado is going in the next, however many years, you can view that. So that, you know, if Dubsado doesn’t necessarily have all the features for you right now, will it in the next few years? And you can double check that. So we have one person heading up that and literally reading all the feedback, everything that happens and prioritize in that with our roadmap, then we have our customer success area. This is probably our biggest area where we listen to our customers and that is one of our larger teams. We have about 15 people on that team and day in and day out. That is something that they do is just listening to customers, taking feedback. And we’re all here in office. So we’re able to yell across the office.

Hey, is this happening? This user’s having this trouble. So there’s a lot of real time communication and, and things that get brought up in there. If they’re important to our users, they’re really important to us. Our team definitely realizes that our teams, our user success is our success as well. 

Yeah. I’ve [00:11:00] interacted with your customer support team quite a few times.

And I have to say. From the very beginning and ongoingly, I’m super impressed by just the, the humanness that happens in that channel. Like I can tell right away that it is a real person who like, is shouting across the room asking, has anyone else like seen this issue? And I really appreciate that. And that comes across in the communication where, um, this is something that I didn’t realize that y’all did that I think our community would love to look at is that roadmap.

Well, you said like does Dubsado is Dubsado going to have the features that I want, you know, a year from now five years from now? Where can we find that?

Yeah. So if you go to our help center, help at Dubsado.com and just type in new features, it will take you to an article that lists all that out.

And it’s really cool. We, it integrates with a system called product board that we use for our roadmap and our users can actually go in and vote on the items that we have. And add their feedback. So, whereas it’s great to see that 200 people have requested this, but have added their little nuances on how it might work best for their business.

It’s [00:12:00] just further getting more information that we need to create the perfect feature for our users. 

Yeah, absolutely. That’s really, really valuable data. I love that. And the fact that you are creating that that space for interactivity is, is huge. So you all use the term boss moments to describe both the good and the bad that come with owning a business and.

I love that because I think that when people hear a term like boss moments, it’s like, oh, like, yeah, the boss moments, right? The moment where you feel like a boss. And I think that, we don’t often talk about the moments where like, you feel like a boss also. And, you, you very accurately said that slow and steady really isn’t clamoring.

Um, on your blog. And so tell us about the last six years, what are the overall trajectory of the business look like? And what were some of your boss moments? 

Yeah. Jake, I’m gonna let you take this one. You dealt with the software and that’s really hard.[00:13:00] 

 I’m trying to pick just one story about what slow and steady really means because. It’s such a complicated equation to be writing software in the first place. Uh, like if you wanted, you could basically get up and running with, with like a basic application, you know? You know, and, and have relative feature parody with a product like ourselves.

It’s the question is, is really a scale and scale comes in so many different ways, like so many different passions, like you said earlier, like swim, swim lanes. And that resonates with me because I’m really, really important swimming. And I was, I was researching it yesterday. All right. Well, if you could just keep your momentum up, you look at yourself more like a boat or whatever.

You can basically swim forever. And I still, I can’t, I can’t make it across the pool and back, but it’s like, once you do finally figure it out. You can sort of swim forever, at least, maybe not in [00:14:00] water, but in, in like your work position, this is the direction we’re heading and you can, you have enough tasks to fill your week and just kind of feel productive each day.

Then you’re able to start like saying, okay, well I need to get this person swimming as well and teach them how to, to get lanes as well. And, and in the software world, this is again, really complicated because. There are so many nuances as to let a single line of code could do or how it can look.

And so it’s really hard across 25 different brains to say this is, and under these circumstances exactly the way it should have looked. so we, we do actually literally just go slow and steady through those problems and we sort of discuss as a team. Like, what is, what is close enough look like?

 How do we all feel in these circumstances? And so, yeah, a lot of, a lot of the slow and steady is, is for us being really honest with what we’re capable of as [00:15:00] individuals and doing our best to work towards each other and prove to each other that we can trust each other on the team. But I guess. Boss moments for myself on the dev side of things is I don’t actually, I don’t know. 

It’s just, it’s more like the people side, it’s the same thing. Like, handling the overall company. Like there are moments. Every, like, you’ll get to getting everyone in their swim lanes and then there’ll be something else that, that falls apart and something else that needs happening.

So it’s like w whereas it just started off with just two people doing everything now, it’s we have 55 people doing all of their things. It introduces a new set of issues and problems and things that need to be solved and exciting things that happen. And you just become a different boss ass that evolves.

And Jake and I were literally just talking the other day. It’s like, it’s crazy. You just, you get to this step and it, the problems become different and you conquer that step and the [00:16:00] problems become different. So it’s crazy. Yeah. So it’s literally. That’s the most exciting thing about being a boss is knowing that you are always learning.

And I know some people don’t like that. Some people just want the easy road, but definitely being your own boss, you have to be open. And, except all those learning things. Cause you are you are literally never done. It’s always changing. 

 I think that’s one of those things that people don’t realize.

Right. Where, and, and I don’t think that’s unique to the fact that y’all didn’t accept funding. Right. I think there’s like, oh, if I get funded or if I have a team of 55, or if I have this many users or we hit this milestone, whatever, then it’s going to be. Then it’s going to be steady, then I’m going to be able to take a vacation.

Then I’m going to be able to, you know, do all of these things. And I think that, to your point, it’s not for everyone, but it is this acceptance of it. Like the problems never go away, they just change in, in format. and I would imagine. Jake that, it is very different, right. You know, it’s, [00:17:00] it’s one problem to be, writing a code base by yourself.

And now you have 25 people writing code, and you’re trying to get everyone to follow the same guidelines. Right. And, and come up with, yeah. This is how this line of code should look then that that’s a different, that’s a different conversation then what do we want it to do in the first place?

And do I have enough time to, to write it? What were each of your. Pinch me moments when you realize like, oh, we’re actually doing this thing. 

 Yeah. That’s uh, I think one of them was when we got our first email of an investor wanting to invest in Dubsado. I mean, now we get them diamond dozen every single week, but that was one of it’s like, oh, someone really has interest in, in Dubsado.

and it was, I guess another one that is more realistic. It’s true. Seeing day over day, more signups come through. And those people telling their friends about Dubsado and it was just really seeing that word of mouth really happening. [00:18:00] And it’s like, people really love us. And I know we always laugh because at one time in a meeting, we were just talking about the future of Dubsado.

It was like in a C-suite meeting, like couple of years back and talking about growth and this and that. And it was, it was kind of like a heavy meeting. There was a lot happening and I just look around at all. You know what guys were so cool and then laughed at me just like that was, again, one of those pinch me moments like here we are talking about this next stage of growth.

How neat is that? That we’re now here picking apart these things when three years ago, or six years ago, we would’ve never been in this position. So I’ve definitely had those. Me personally. I know Jake has had had some as well, but, definitely many times over the years and over even this year. 

Yeah, totally. It’s it’s such a cool feeling to realize like, oh, I’m, I’m having this conversation because I have to, I’m in a position where I have to have this conversation. How cool is that? Yeah, that’s awesome. Jake. What about you? 

Yeah, I think for, for me, [00:19:00] it would be more of an inside joke and it’s that people are always coming up from behind me and they, they pretend to be taking off some VR headset and then they come in front of me.

They’re like Jake, this was all a Dre. So I’m actually like always looking for people to pinch me, uh, just to make sure that I’m actually present. yeah. I, I think for me it was the first time we hired developers. It was really, really, really, really, really, really difficult, uh, leading up to it. We actually had a lot of trouble with finding talent to begin with.

Uh, we went to local colleges and we said, Hey look like, are you teaching people that we can hire? And they’re like, no, not really. We’re teaching people to go get jobs that I don’t know, XYZ engineering company. Um, but they’re not really teaching about modern web standards, how to build a product and have to scale a server.

So there’s definitely a discrepancy, at least at that point, bootcamps were not really the norm quite yet. They were kind of coming to be. And, even [00:20:00] then it was very much like, uh, There, there were very scrappy and very quick paced programs that weren’t necessarily living up to the quality, which their homepage sort of, described for the talent.

so yeah, we, we did eventually find the, bootcamp that, worked really well for us. And we did a bunch of hiring and interviewing and we sort of became immersed in that culture and. I think like our first round of hires ended up being three developers to, in one fell swoop. So I think that was, that was really big and exciting thing.

And a moment where it was like, there’s really no turning back at this point.

Yeah, Yeah. Once you’re responsible for people’s livelihood, you’re like, oh yeah. Okay. It’s real now. What, um, what are, what are some of the philosophies that drive the way you and your team, right. And review your code. 

I would say there’s a lot of different terms that they use in the software development field of like philosophy or the management [00:21:00] style.

And there’s like a terms for everything like scrum and whistle something or master something over there. for us. At least, at least at that point, when we’re bringing on three to five new devs in the first sort of period, we didn’t really have a style because we saw exactly what needed to be built and we were just working on it.

 we were, one team, so it was more like a singular focus level. And I’m gonna, uh, ask the question again. I think I lost, I want to make sure I come back to the. 

Yeah, the question is, um, what are some of the philosophies I used one of your buzzwords that drives the way you and your team write and review code? Like what’s important to you in creating the code base for this product that you’re building? 

Yeah. Yeah. That is definitely a buzz buzzword for me. and funny things like that. Can I both really try to avoid like anything sort of cliche or buzzy, but that one is very exciting to me because, It almost like the very beginning of Dubsado, we took a very [00:22:00] philosophical approach behind it because we didn’t know exactly what it needed to do or what it even needed to look like.

 So we basically just put our intentions out there first and I was like, we want to. Just make people be able to get paid faster. Just sort of like basic instinctual things behind what we’re trying to produce. Yeah. And so I was hopeful that Dubsado like, would exude like the philosophy of free. Like, we, we give you as much time as you want.

Like, we want you to be in charge of your brand, so you’re free to express yourself. And so yeah, hoping everything product-wise extends to that. Um, but on the developer side, it’s, like I said before, It’s very easy to get into the weeds. And it’s very important to get work out those details. But if we’re not fundamentally sort of stemming off of just like a core seed of philosophy, that is like, Hey, just do it a little bit, a little bit better than we did yesterday.

 Then we forget sort of what to come back to. So I [00:23:00] definitely think philosophy is very important and it’s sort of just infused with, with our whole culture. 

Yeah. Yeah. I love that. I think that you said, the basic instinctual things and focusing on making those things, Easier right. With, with less friction, you know, we use Dubsado for all of our client onboarding and offboarding, and that is always the thing that we’re focused on for that process specifically, not even just for us as a team, more so for like our clients, right.

To be able to get them through that process in a way that has less friction and less hoops to jump through. And it’s very instinctual and intuitive for them to. so that, that really resonates. So where, where did the name Dubsado come from? 

Well, as you know, we’re a family run own company. And when we were developing the name Dubsado, Charlie, who was our two year old son at the.

Now he’s eight was, uh, running around the house, singing a song, dubs the bead dubs out, out. That’s what he does it out. And he just [00:24:00] making up words. Like he didn’t really know how to talk very well at the time either. And so as Jake was developing out the software, we still didn’t have a name. They hadn’t, we just were like, well, let’s have it be something that Charlie names.

So we put the words together and named it Dubsado. 

I love that. What a good story. And I love, uh, I love that he’s featured on your website. That is his official title. His claim to fame is that he came up with the name, Dubsado. I’m sure he’ll appreciate that. When he’s a little bit older, if he doesn’t yet. 

Uh, he will. And sometimes when he’s off to school, every single signup that we get in Dubsado, we send a little welcome little packet with the little stickers. And Charlie will often pack those and he’ll, he’ll get couple dollars per hour, but he says he’s saving it for his first car. So, he has a little part in Dubsado.

 I love that very clear priorities. So, um, y’all work together and your life partners, and you have kids. What are some of the rhythms and practices that you’re committed to, to keep your relationship [00:25:00] healthy across those different areas of life? 

Patterns. It’s definitely something that we have a religious occurrence to our entire days is essentially just like.

coordinated dance of like, all right, it’s going to take 12 steps to get to the kitchen and that’s going to cost me. I want to have to go get the kids. So I better like take three less sips of water. and then, so after work, it’s kind of just like very routine oriented. It helps our kids, we hit, we hit the schedule, they know what to expect.

So they’re hopefully brushing their teeth without us asking. Of course we are always asking. Uh, two or three times to do it.

Routines or routines are our thing. Totally. And like Jake said, it’s, it’s, it’s a dance, but when we have established our routines and what each person, when I know what Jake’s going to do, I know every single day. His job is to get the kids and start dinner. [00:26:00] And my job is to make sure that they’re all showered brushed in bed.

So it’s like, we both trust what each other is doing so that there no low, why didn’t you do this? Well, why didn’t you do that? And that’s something we learned very early on is just being able to trust each other. And know that each of us got our things handled and, yeah, it’s a dance. We have literally our day planned out to a T when we get home, like you could look at, into our house at like four thirty and we’ll be doing the same thing every single day.

 Yeah. I love that I’m the same way. And I totally relate to, like the patterns throughout the day, my brain kind of works similarly of like, okay, if I have to do this at this time, do I have, do I have time to shower? Do I tend to eat? Do I have to pick which one I’m going to do? Which one is more important today?

So that, that makes a lot of sense. So there’s a couple of philosophies that, that y’all have, and, and I love the, the phrases that you’ve put behind your advice and, and your experiences and the way that you, um, [00:27:00] That you’ve kind of labeled the things that, that are important to you and got your company to where it is today.

And so one of those things was in the hiring realm and, you know, I, I originally wanted to interview you because I like landed on your website for some reason. Already a user, but I was like looking for something and I saw that your whole team was on your website, which is pretty rare for software companies.

And so, you know, that combined with other interactions that I’d had with, with your platform and with the tech and with the brand, um, just told me that you really have like a really important humanness right. To your company. And then, you know, in this conversation, obviously learning a little bit more about that.

And so, as it relates to hiring one of the pieces of advice that was on your blog, that I was just talking to someone about earlier is don’t try to hire superstar And you want humility over someone who thinks that they’re the goat. And I was, I literally had just said [00:28:00] that to someone the other day, I was like, I think what makes people successful at Curate Well Co is like a certain degree of humility.

Right? You just have to be willing to like, kind of. Do anything and not have that, like say anything about you and not think that you’re above that and everything that comes with that. What are some of the other hiring philosophies that have helped you build a really humanized technology company?

 Jake, you want to take this one? You’re the, you’re the hiring master. You’re good at this.

 if I do qualify to be a master at it, it’s because I have made more mistakes than I care to admit.

In my opinion, it’s the hardest thing about growing a business is hiring people and managing people. At least that’s been my experience. 

Yeah. I mean, you really get to learn about sort of your gut feelings and intuitions.

I think. A lot of it stems from just how good did you feel at the end of the call and then the qualifications, if they’re there, then they will, they will prop up [00:29:00] that feeling. Um, and, and yeah, I mean, I’ve lost the question already. I wanna make sure I come back to it. 

Well, and, and Jake was really good with, with gut.

We, we do make a lot of decisions on our, on our gut. And, uh, one thing that we do look at, like you said, uh, as what you do with your company as well is do they just, do they exude like a willingness to do. Anything? Uh, yes, we put out a job listing for customer success, or we put out a job listing for, uh, being a software engineer, but does do these people embody the Dubsado culture of us just being there to help anyone and do anything. Here at Dubsado once you’re, once you’re part of the team, we have kitchen duty where we clean up the kitchen together.

We have certain duties that we all. As a team collectively take care of the space that we’re in, take care of each other, and it becomes like we call each other. We, we are a Dubsado family. It’s the same thing that a family does. So is that [00:30:00] person just coming here for a job and to clock in clock out?

Probably not going to be the best person for this. This is something that Dubsado is a culture. That’s auto is something that you get in there and it becomes part of your life. and not that you have to take work home with you. We definitely do not do that, but it’s just, you, you make friends here and it, it becomes something a little bit bigger than just yourself.

Absolutely. What have you found to be, uh, impactful in creating that like genuine buy-in right. Like to have people want to show up in that capacity? Um, part of it is, you know, just they’re who they are, right. And their, their attitude and their personality and how they approach life. And I also think that there’s a set of like leadership activities that create the environment where people are excited about that, right. They really like, they want to be a part of the family and they want to clean the kitchen because they believe in something. How have you, like what’s gone into you creating that environment. 

[00:31:00] I think it all starts with leadership and like, I just, no job is too small for anybody. You will see me or Jake down on the floor, scrubbing it.

If there is something or just on Friday, uh, me and our chief people officer, we’re installing gym. Like it comes from above. And if the people in leadership and every single person who, who leave, who has grown into this leadership role can do that. Then there’s a natural, just willingness to pitch in.

And of course what we showcase on social media, or we write in blogs, it’s fun when we all get to do it together because we’re all enjoying the fruits of our labor. We worked really hard for this and yes, hard work is hard, but also when you’re doing it with the people who all have the same mentality and this person’s over here cleaning this and this person’s over here answering tickets while they build up and this person’s gone.

It, you get a respect for everybody, [00:32:00] and that is fun sitting around, not doing anything. Cool. It sounds fun. But. participating in giving your heart to something becomes fun 

Yeah. I love that. I think it’s that, that lighthearted respect is, is really what creates that work culture, at least in part. There were a couple of other sentiments that you all have shared that I’d love to have you unpack a little bit.

And one of those is you can do more with less. You can do more with less t han you ever thought you needed. So how have you, like, is this something you have always believed or did you come to believe this through a set of learning experiences? How did you land here?

 I have so many directions I can take this.

I’m going to start with the retreat center that I used to work. it was basically myself and two other people working on-site and we had 20 cabins to maintain and manage and we had, so that was 20, 25 beds to make every single Thursday for a group to come in on a, on a Friday. And we sort of, [00:33:00] you know, develop the, the, the routine of like, okay, well, this is, this is how much work we have to get done.

 And, and so we, we put our heads down and then we, we did it and sort of when we, when we found ourselves enjoying, enjoying the process a little bit time, went by a little bit more quickly. But I think like when you’re on number five, out of, out of 20, you sort of looked down the lane and you get this vertigo effect, where it’s, it’s a long road ahead of you.

I know you’re going with this. Well, yeah. when Jake worked at the retreat center, it was, this was before Dubsado and it was literally just him and there was a lot to do. And so he would literally say, okay, this is how much time I have in the day. This is the people that I have. How do we maximize this?

And we as Jake and I were like, we’ve always been put in a situation where. We didn’t have, uh, either we didn’t have enough to do what we wanted to do either. We didn’t have enough money to write this check that we needed to write pre Dubsado add to pay for insurance. We didn’t have time to start a business because we had two kids.

We didn’t have [00:34:00] all of these things, but if you look at it that way, of course, you’ll never start. Of course, you’ll never do these things, but if something is really important to you, You will go and you will do it. So what did we have? We had didn’t have any money when we started Dubsado. But Jake had a programming brain.

I had a knack for talking on social media and we put those two things together and we made more than what we had. So it was just about using what we had and taking that and going with it. And we still have those same values today. Every single dollar that Dubsado makes gets put back into the company.

So we’re not spending a lot of money on just going out and doing these big things that software companies do, because we want to figure out how we can maximize the dollars that we have here to grow Dubsado, even bigger. And it’s, it’s worked great. It’s worked great now, just by. You know, if we can’t, dump a whole [00:35:00] money into, let’s say a whole bunch of hiring things.

Okay. So what can we do for our people here so that they feel cared for and loved? Okay. So introduce mental health days. That’s something that doesn’t necessarily require a ton of money for us to do. So how do we do more with less? We do mental health days. We do, we just do certain things that we can work with, what we have, And that’s kind of been our motto for everything.

Like what can we do? You know, it’s not the, you don’t have to be industry standard. You don’t have to be doing what Facebook is doing. Google is doing. Like, we couldn’t compete with that, but what we had, definitely not a PM to me. And that’s the beauty of coming to work at Dubsado it’s definitely still something six years in that we still live by. Just what can we do with what we have right now and make that bigger.

I love that are your mental health day similar to PTO where your team can request them and take them when they want, or is it like a company-wide day where you’re like, surprise everyone has this Friday, [00:36:00] they can take it whenever they want. I feel like there have been some hard times that have popped up for people and you can’t, you can’t plan that.

And if you don’t feel like showing up to work and you just, you need a day to go get a massage or sit at home and veg out on Netflix, 

do it. 

 I love that. That’s amazing.

 We’re going to take a quick break to tell you about our membership. We’ll be right back to the episode soon.


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Our members hire each other for support in their businesses, offer vetted recommendations and referrals for other providers, tech solutions, and more. Celebrate each other’s wins, generously and genuinely. [00:37:00] Ask for and receive advice from a wide variety of perspectives and share vulnerably about the experiences most entrepreneurs aren’t willing to talk about. We offer trainings for me, Pia, we bring in qualified guests experts to teach on relevant topics. We host social events and facilitate member panels. We also offer a member’s only quarterly spreadsheet drop. And if you’re a member, you’ll get access to the exclusive podcast episodes, which we call the debrief, where we share pieces of episodes that don’t make it into the final cut.

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 What lies in the future of Dubsado? What do you want the business to be in five years? 10 years?

Yeah. This is something that we really honed in on a couple of years back. So we have Salesforce who is great for enterprise, really large corporations and running their business on HubSpot is really great for the midsize business owner, but we want to own the market for the small business entrepreneurs. So anything from a solo entrepreneur, to someone who has a team size of 10, that’s what we found is our sweet spot of Dubsado. So over the next 10 years, we want to be. oh, we want to own that space and push forward with it.

And we’ve made some really great strides in the last six years. When we launched Dubsado, we were already launched into a saturated market. There’s CRMs are a dime a dozen. There are a ton of them. [00:39:00] And even in our direct competition, the b usinesses that are here are heavily funded and we’re still at the same level.

Well, I’d like to think a little bit better as them in pushing forward. So, um, it’s definitely looking bright and we have our roadmap, um, that we, we share externally, but we have our internal one as well of like really those, those goal points that we want to hit. And in terms of growing that to reach that, small size entrepreneurs, home brand name or what does that, the household name?

Yeah, absolutely. Um, and, and I would say your. Well on your way, if not already, arrived in that and you’re a really well-known name in the circles that we operate in. On that note. I know that I’m building community for your users and in the small business space is something that, that y’all have done.

You have a certification program, and you’re very active and involved in your community. And I think you being here today is, is a testament to that too. How has that played a role in [00:40:00] becoming that household name for entrepreneurial businesses.

Probably the biggest, the biggest role. It is the main thing.

One thing that really shaped us to who we are today is that word of mouth and creating community. I soon realized very, very early on when Jake was developing out the software. And I felt like I was just twiddling my thumbs. Like I’m just waiting for this, this feature to be launched or, and waiting on this and waiting on that.

Yeah. I needed something to do with my time. I needed to talk to the people I needed to be busy. And I realized that. In giving back to the community in hosting webinars, really diving into education, really supporting them in their journey. It intern made Dubsado better than it was. So we learned very early on in getting affiliate codes launched as a feature, so that people can share about Dubsado And once we did that, our next phase very early on with seeing that there was an ecosystem of businesses [00:41:00] starting to set up Dubsado. So Dubsado users helping other Dubsado that are users set up their Dubsado account. So we’re seeing this happen. So that’s why we started our certification program where people can get certified.

So, you know, that this person is backed by Dubsado. They took a rigorous exam. They’re, you know, part of this, this community where you are held to a higher standard. And that’s something yeah. That we, that we realized very early on was very important. Being with like people sharing their experiences and, and their journey was something very, very powerful that, you know, you can’t, you can’t just pop out of thin air.

It, it grows as the company grows.

I totally, so I have my own opinions on this. and I would love to hear it from your perspective, what are the pieces of the technology and the functionality that you think set you apart from other CRMs, knowing that they’re all. Quite a few. 

That was a very conscious decision that we made early on is what do they not do?

How do we fix that? And [00:42:00] the, the biggest one was customization. And we realized, and that was one of the main reasons for us starting Dubsado is I tried out other systems and it didn’t feel like me when I put my, my forms in there. And it’s just forced into this box of how that CRM looked. So that was one of the biggest things.

When we created actually the first feature that Jake created was our, our forms and, creating our, our template area. And we just knew we wanted it to be very customizable. We wanted to feel like an extension of someone’s brand. Now it shouldn’t be a very severed thing of going from your website to now inside of your onboarding and your off-boarding.

It should feels very continual. Like it’s we didn’t change systems. That and our, our automations, it’s one of the bigger ones that has more, our workflows have more triggers and actions than most other of our direct competitors. and that’s something that’s very exciting to me because, [00:43:00] you know, workflows are powerful.

 What was yours?

Um, so, you know, for me, it’s, it’s the customization too. I’m a sucker for like, build your own anything. And so, the, the fact that you can write your own emails and that you can have some trigger automatically and some trigger manually. Um, and also this is a super, super small thing, but I love that you can put a button in an email.

Yeah. That just blows my mind. I’m like, in all of the emails that I send in all of the places like y’all could like trademark that and just do that. And I would like travel around the country and be like buttons in your emails. I’m sure it was because nobody else has done it. I haven’t seen it anywhere else.

So I’m sure that it took a lot of effort to figure that, to figure that out. 

And their outlook particularly ever, because every email client wanted to show. 

Yeah. You know, I think, I think it’s the customization for us. We like to have a [00:44:00] very hands-on onboarding and offboarding process. And so, the fact that we can create these workflows and create these templates and make it a little bit more efficient for our team and have a standard that is an extension of our brand and be able to edit those emails before we send them and links a unique document into a button before we send it.

I think it has our clients, really just feel like super, super supportive or did excuse me. And it, it allows us to be really, really hands-on as we continue to grow. And I haven’t been able to find that with a lot of the other tech that we’ve used in the past or, or currently use for different purposes.

It makes me happy to hear.

 Good. Your hard work is, is certainly paying off. If you were to give one piece of advice to business owners who want to scale a software company or an otherwise technical company that really has humanness at the core of everything that the company is doing, what would your advice be? 

 I think it’s, it’s [00:45:00] twofold.

Um, one of them that I’ve talked about a lot in this is what Dubsado is created on. It’s just being better than you are the, the day before. Walking into a room and leaving it better than you found it is. It’s one of our biggest things. And then the other part to it would be growing a business, especially software or any type of business that is going to expand to be something beyond yourself, it’s going to take a lot, a lot of work. And oftentimes the first couple of years is, is one of the hardest times. And in growing a business because you’re doing more than you should, you’re coordinating, trying to get hires and all of this and that. And you’re still learning a lot yourself. And it’s just acknowledging that there will be the first couple of years will be hard and we’ll be super.

There will be very, very trying. Um, but something that Jake and I learned very early on is we looked at each other and we’re like, we’re not going to be doing this [00:46:00] forever. We’re not going to be in this state forever. And we are going to work towards creating that life that we want to create. Um, it was something that we knew we couldn’t get in year one, two or three of Dubsado.

And we were very real with ourselves. And I know a lot of times people just think they start a business and they can sit back and go to the beach and they can take those breaks. And it’s, it’s, it’s not that beautiful, especially at first. So it’s just acknowledging that it’s going to be tough at the very beginning, but ultimately you’re going to be working towards creating that life that you want to live, and it will reflect in how you build your business.

So be patient with those moments and you’ll get to it. You will. 

Jake what about you? If you were going to give one piece of advice to business owners who want to scale a software company with humanness at its center, what would that advice be?

 Okay. I think that lands on another topic. That’s really exciting to me is because this whole time we’ve been doing Dubsado it’s also been very motivating for me to know that there’s so much more [00:47:00] opportunity in the market of software in particular. I think there’s not only room for growth, but just.

 It’s almost like ever expanding, like will forever have smaller and smaller problems to solve. And so we kind of looked at Dubsado as something that would off shoot or, turn into maybe a smaller projects or, uh, another projects would, would come under our wing and we can share what we’ve learned over the past half decade.

and. And so with that, I don’t have any one piece of advice other than I do agree with Becca. Like the hard work side of it is good. I mean, obviously I think people can expect to have to work hard, but I think that a better way to phrase it is persistence and commitment. Because it’s a little bit harder to tangify doing something for two years when after the first year, every single day, that goes by you’re, you’re sitting there staring at yourself, asking why you’re doing this to yourself. It [00:48:00] became like how you perceive a year becomes much different. it’s time to change. 

Yeah, absolutely. I agree with you.

I think that persistence and commitment, and building something that you are really committed to, right. Is where it starts. It’s really hard to be committed to something that you, like in your, in your core, like don’t actually want to be that committed to. And so I think it starts from solving a real problem, right.

Doing it for people who, you know, actually, and, being, that intimate with. The solution that you’re providing. 


What else I’m handing both of you, the Mike, and I want you to say whatever you think needs to be said. 

I feel like you’re starting a business and growing there is a lot of power and just listening to user on your and your customer.

It can still align with the goals that you want to have and the future that you see, your customer, that you see your company going into, but your company wouldn’t be anything without the people that use it. And [00:49:00] there is great power in just being a listener. And it’s hard to do when you’re growing your baby, like your business baby, and you have your own actual babies, but it’s it’s cause you have your ideas and how you want to do things.

But, if your users feel like they are connected to the company and to you, you will ultimately create. Th that community that we were talking about before. You’ll create that sense of belonging and that brand that you exude, it becomes a lot more contagious than just a software company that then can easily click cancel or whatnot.

You know, they know when people sign up for Dubsado. You know that you, it’s a, it’s a family run company that we work really, really hard here. We deliver on things that we say we’re going to deliver. And so you are participating in that. You are becoming part of that when you sign up for Dubsado. So when you create that community, it is contagious [00:50:00] even to your users and.

It all starts with just having conversations with people and listening. It doesn’t have to be in person. Doesn’t have to be one-on-one. It can be in a Facebook group. It can be on social media. You need to be able to see the people that are using it and converse with them. 

I agree with everything you said.

I couldn’t have said it better myself. That was awesome. Thank you for so eloquently tying that all up for us. 

It was great being here. 

Jake, what about you? Anything that we didn’t touch on that you want to make sure to say.

 Yeah, thanks for the opportunity. I think I just wanted to selfishly, considering Becca and I are one person.

So I, I would like to brag about her for a second. like the level of c ommitment to really understanding situations and circumstances is really difficult. And I think she was much more capable of it than myself initially. And so being able to look at feedback and in its raw form is a very difficult thing and it’s very difficult to, basically continue to do consistently for [00:51:00] six years straight.

and, and so I know that plays into persistence, but I, I. To take it even a step further than that. And I think there’s a level of obsession that’s required. That can obviously get out of hand, but it, it is a kind of a precursor to, to where we’ve arrived. Because if I don’t see Becca on her phone checking customer feedback, at least once before we go to sleep, then I know something isn’t right in life.

I don’t know how to say it, but like, Always in there. Just getting, just getting like in programming terms, we have this thing called tail, which spits out last little section of information out of a file. And so she’s basically just tailing, like, okay. Is anything out of the unusual here? Because she knows that it’s not that no one else will be doing it, but to have that single point of understanding and consistency, has saved us on a number of occasions, probably more than a dozen times where it’s like, okay, There is something wrong, but only I would have been able to identify this because of the different areas which I’m tapped into.

And I know whoever’s in the inbox right now. [00:52:00] Didn’t see it. That’s my first point is, is Becca’s obsessiveness is, is admirable and her ability to take a look at the truth for what it is. And, and even once you’ve run, like you’ve really ringed out the, the feedback then it’s like, okay, It’s almost more like esoteric, like, okay, what what’s life trying to tell me at this point with this information, because we can’t address every single thing.

but we, we do have to expose ourselves to it. but I think that sort of people have a tendency to get into like power struggles, unnecessary. uh, oh, well, you know, this person is my boss, so I’ll just do whatever they say. Like everyone is constantly trying to sort of label themselves into a position, which I think is good, but I think it can go too far as to say, well, I’m not going to do this because it’s outside of my lane.

And so we’re in that sense, we try to keep our structure as very flat as possible, where. Essentially, even though it might not be in your lane, you can still be aware of it. Like we try to cultivate a lot of transparency and I think that goes into like sort of the [00:53:00] self honesty side. It’s like, okay, well, this is a, this is an awkward truth to admit, but like we know that we have to admit it to ourselves and to the surrounding people so that we can all collectively come to an understanding.

This is, this is what’s happening. That short traveled between, the customer writing in with, a complaint or, some feedback that how far it needs to go to hit the very top of the organization is very far. uh, whereas if it was an Amazon, like they, they have like AI models that make sure things get categorized before they even hit a person.

so it’s definitely, maybe it may be a strength in that regard. I think ultimately we’re all sort of trying to solve the same issue. So no matter how big or how smaller, how scarce your resources are, like there’s always going to be a better or different way to do something. And that’s why our philosophy always comes back to just trying to have fun at work.

 I love that you hit on something. All of that was, was fantastic. and you hit on something that I think is really important, which is this idea of self-awareness and having awareness of the things that are [00:54:00] outside of your swim lane. And I think that’s really powerful and facing those awkward truth because there is always something that could be, could be done better or could be improved and when we can come together and that, that’s how we’re able to be a little bit better than we were yesterday.

 Becca and Jake, thank you so much for being with us today. This, feels so special to have you here. Like I said, uh, the Dubsado name is a familiar one in our community, and I know that all of our listeners are going to be just absolutely blown away by the fact that they got to hear from both of you about what you’ve done.

And, I want to acknowledge you for just building something that is really. Has a lot of depth to it, both from like a technological perspective, right? Like depth and features and, and depth in, functionality, but also the depth of the humanness, right? From your website to your customer support team, to this conversation, to, getting, you know, a packet in the mail when you sign up, like it’s, there’s so much depth to the [00:55:00] brand that you’ve built.

And that is so uncommon in the technology space. And, as a user. I can feel it. And I want to acknowledge you for that because I know how much commitment and how much work it takes to build that. And you’ve done it in a relatively short amount of time. So congratulations on everything that you’ve built.

And, thank you so much for offering us your words of wisdom today.

Of course, that means so much to us. Like we always, we have shirts at that say software with heart and that’s, that’s all we are. Thank you. Yeah, that was, it was a great conversation and it’s always, it’s always fun diving into questions with Jake. When Jake and I get on these together, it’s nice falling in love with it again.

And, we always are, but then just diving back through the memories and stuff like that. So it’s, it’s always, this was a great conversation. Thank you so much for having us. 

Thanks for having us. 

It was so cool to see how Becca and Jake balance each other out. So well to hear about the [00:56:00] culture that they’ve created at Dubsado for their team and how community-based their business is. I love that they decided not to take funding. That they prioritize talking to the people who use their technology, how they describe that persistence and commitment, tangify our businesses and the importance of leaving the room better than you found it You can find out more about Dubsado at www.dubsato, D U B S A D O dot com. And you can use our code CURATE10 when you sign up.


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