Interview with an Entrepreneur: Jake and Becca Berg from Dubsado

Jake and Becca Berg are based in Burbank, California. Parents of two young boys, they created a client management system for creatives like themselves who wanted to make time for their families and creative pursuits. We sat down with them at their regular table in Studio City’s Aroma Cafe to talk about their entrepreneurial process.


Jane: Talk us through what was going on in your lives when you realized the need for Dubsado?

Becca: I was photographing weddings at the time. I remember I had booked my first wedding and I realized I didn’t have a contract, so I created one. I sent that off, and when it came time for the wedding I couldn’t find any of the questionnaires, contracts or anything I had sent because [they were] all lost in a deleted email. I just kept losing things, so I needed to find a system and I knew there were other options out there. But I found that they were too robust and had too many features that were cumbersome to set up. I knew that we needed to create something a little bit simpler, but [that] still had the features that people needed, and was affordable for a person like me. I wanted it to be simple and affordable, for the average freelancer.

Jake: I already had created a smaller version of Dubsado for myself.  I just did it for practical reasons. And I kept telling Becca that I wanted to make software that tracks your ‘to-do’s’ and your business and you can tag people and things and yada yada yada, literally for years. And she’s like, ‘That’s dumb.’

[Becca laughs]

Becca: I thought it was boring!

Jake: [She said,] ‘Let me know if you have any more exciting ideas.’ So then she comes out of the bathroom one day, years later, and says, ‘I have an idea. I want a place where I can track my ‘to-do’s’ and things in my business,’ and I said, ‘Okay, sounds good.’ But I’m going to go ahead and say that I’m the one who started this idea…

Becca: He did, he did. I’ll give him that.

Jake: And that’s it. It was birthed a long time before. It was really simple, but now it is a lot more advanced, faster.


Jane: How have you designed this program to save time for users?

Jake: It all kind of starts at the data level, how you are keeping track of things like jobs and contracts. There’s a model behind it, [and] if you don’t pick it right from the beginning, you’re totally screwed and your program will reflect that. So the first three months of developing, Becca’s like, ‘Can I see what you’ve worked on so far?’ and I showed her my journal. Everything was written down in bubble charts and I was sketching out how everything should piece together.

Becca: Literally, we sat–no joke–at this table. Because date night was on Fridays. We would sit here at this table most of the time, because no one wanted to sit here because the sun was always here at that time. And it was just going over notes. It was the hardest thing in the world, just designing something that we knew worked for us but we also knew would work for everyone else as well, or for any kind of business.

Devon: What steps did you take to make this a reality?

Jake: Like what was the carrot in front of our head? The first website we made, we decided to create when Becca first thought of the need for it and we agreed to start. We picked the name and WordPress theme that night. It was just one page that said “coming soon” and then some really vague ideas of what Dubsado would be. So that’s what we held on to for a long time.

Becca:  We were able to promote ourselves on Instagram through the landing site. We were able to receive feedback from our website, get an idea of what people were looking for. Since we were in this design process still, hearing what they wanted, we were able to make better decisions on what to include. So for a while we were doing the little bubble charts and we were taking feedback from those people into consideration.


Jane: Do you look to build a relationship with your clients, make it as face to face as you can get?

Becca: Yeah, and we’ve been talking about that for a long time. Our main goal is making sure our clients know that they can come to us if they need anything. I try to make that very clear in the emails that we send them, they are all very personable. As soon as they sign up and pay they also get a welcome gift. It’s a thank-you for joining the Dubsado family. We want our clients to know that they’re family. I just started up a Facebook community for our users too. I want people to be a part of the vision.

Jane: I was getting that sense because of your blog. It’s a different element for a company like Dubsado. What was the vision behind the blog?

Becca: The hardest thing, probably, of the entire business is keeping up with the blog. Finding content can be difficult. Since it’s just Jake and me at the moment, I’m the one who is trying to figure out the content and I want to get a few more guest writers and things like that in the future! But right now it is just about entrepreneurship, and once in a while [we post] tutorials on there as well. I definitely want the blog to be something a little bit more participatory and interactive.


Jane: We’ve been really struck by your emphasis on family time. Why have you fought so hard to achieve that?

Becca: Being small business owners, it’s kind of impossible to find a perfect balance. My parents own their own business as well and I always remember them talking about work at the dinner table. It’s not a bad thing–I learned business because my parents brought that into the house. But our first son, he’s kind of a crazy, wild kid and it was just kind of hard to bring work home because he needed our attention. Since I was struggling when I was doing my photoshoots [to] keep up with stuff, I knew that other people could probably benefit from this. And also on the other end, we wanted our Dubsado users to know that we are a family. I wanted to make it obvious that the people who are running this–we’re real people. We go home at night and don’t sleep because our three year old right now doesn’t sleep. I want them to know that we’re going through the exact same things they are. You know, we hope that we can make people’s lives just a little bit easier by creating and sharing this.

Jane: What would you say that you have learned creating your own business? And what would you go back and do differently?

Becca: The hardest part of starting it up was finding the balance.

Jake: That was a pretty early struggle, and then working at home with our son jumping all over us and that turned into having to work all day because we weren’t getting as much done. So we had to spread out our time, which was really stressful on us and our kid. When we decided to hire a nanny, we were able to work as hard as we could during the day so that we could focus entirely on him in the evening. It helped his behavior and level of happiness and ours too.

Becca: I had no idea what it was like to build such a system. Still to this day I wonder, ‘Is that going to get done tomorrow?’ Just trying to understand the process, I think, has been the hardest thing for me. Since we each handle such different aspects of the business, it can be hard to understand what the other is doing. Working with your spouse is a whole new level of entrepreneurship and it’s literally all just about understanding and communicating. If I would have told myself that before we probably could have avoided some stress.


Jake: The crunch time came when we did the soft launch, when I finally started writing the program which happened in three days straight. I had all of the foundation with the notes and sketches and now had to make everything work right. And that’s when Becca saw my process. Day one I was like, ‘Okay Becca, I’m going to have it done by ten tonight.’ Ten comes and I said, ‘I’ll have it done by six in the morning.’ Six in the morning came and I said, ‘I’ll have it done by ten tonight.’ And then that went on for three days.

Becca: That’s another thing I learned–deadlines. It’s really hard to say it’s gonna be done by this date. You really never know. Yes, he did think he was going to be done at that date, it’s just that things kept popping up that he didn’t even foresee. So I have learned to estimate more time, because you never know what else could pop up. You could have slept that week, Jake, if we had given people a later date! [Laughs]

Jake: Yeah, I wouldn’t take it back though because it got done. It required an immense amount of energy which built up and then came out when it needed to. And then I slept for a week and was back to normal after that. Now we try to give a more realistic estimate. It’s been good since then.

Becca: We’re looking into a person to work with Jake as well now. Someone to help him work the back end. We just had someone do some front end work for us for the first time, and it was a lot easier on Jake, a lot less stressful. So, help is amazing. You can’t do it all on your own. Even though it’s our thing to just go and do it, we realize we need help. We’re still doing it but there are only so many hours in the day.

Jake: Yeah, she doesn’t necessarily want to spend the money all of the time.

Becca: [Laughs] Yeah, it’s hard, but it’s worth it. The best thing that you can invest in is your own business. And that’s just what I keep telling myself! That’s the best thing, it will pay off.

Learn more about Jake and Becca’s company on the Dubsado site. All photos from this interview were taken by Devon Johnson.