Inspiring Conversations with Rebecca Berg of Dubsado

Today we’d like to introduce you to Rebecca Berg.

Hi Rebecca, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
My story really starts with photography. I was 13 when I started doing headshots, and what I loved wasn’t the technical side of it. It was watching people’s faces change when they felt good about themselves. That feeling of creating an experience where someone walks away feeling seen and supported, that’s always been the thread.

When I was a photographer running my own business, I was a mess organizationally. I was losing track of project details, missing invoices, chasing down payments. My husband Jake is a developer, and one day he just started building something for me. It was this little system to help me keep track of my clients and actually get paid on time. That was Dubsado in its earliest form, a love letter in code from my husband so I could stop drowning in admin work.

We weren’t ready to start a company. We had no outside funding, no certainty it would work. Jake literally set an expiration date in the code because he wasn’t sure it would last. Three years ahead. One day everything just shut off and we were scrambling to figure out what happened. Turns out we’d lasted longer than he expected.

That’s honestly how we’ve built everything. We jump and figure it out on the way down. We’ve never taken venture capital. We’ve grown this completely self-funded over 10 years, and served around 120,000 creative entrepreneurs.

Along the way, I’ve learned a lot about myself too. I recently got tested for ADHD and autism, and so much suddenly made sense. Why certain parts of running a business felt impossible while others felt totally natural. Why I stack all my meetings on one day so I can recover the rest of the week. Why I need routines like my 5am workouts to function. I’m learning to work with my brain instead of against it.

I’m a mom of two. I run a tech company with my best friend from childhood. And I’m still figuring it out every single day. I just don’t pretend otherwise.

We all face challenges, but looking back would you describe it as a relatively smooth road?
Not even close to smooth. I think anyone who says building a business has been easy is either lying or selling something.

The early years were scrappy. We were building Dubsado while I was still figuring out how to run my own photography business. There was no playbook. We just kept solving problems as they came up and hoped we were making the right calls.

Around 2022, we went through a really difficult season internally. Culture stuff, leadership challenges. I had to look hard at myself and how I was showing up as a leader. I realized I’d been so focused on building that I wasn’t always listening the way I needed to. That was a painful but important turning point. It taught me that people are the whole point. It’s not just about me and my vision. It’s about creating space for others to be heard.

We also made a massive bet recently. We paused feature development for two and a half years to completely rebuild our platform from the ground up. Two and a half years of telling our users “it’s coming” while we worked on something they couldn’t see yet. That required a lot of conviction and a lot of trust from our community. We launched 3.0 in November, and I finally feel like we’re building the product I originally envisioned.

On a personal level, I spent a long time feeling like I had to prove myself to other people. I was told growing up that I was too delicate, that I couldn’t do certain things. For years my motivation was proving them wrong. But that fuel runs out eventually. I’ve had to shift to proving myself right instead. Believing in my own capabilities because I know what I’m capable of, not because someone doubted me.

The hard days still come. I just don’t let them make the decisions anymore.

As you know, we’re big fans of Dubsado. For our readers who might not be as familiar what can you tell them about the brand?
Dubsado is business management software for creative service providers. Photographers, designers, coaches, consultants, wedding planners, virtual assistants. People who started a business doing something they love and then realized they also have to chase invoices, send contracts, onboard clients, and somehow keep track of it all without losing their minds.
We help them streamline operations, create repeatable processes, and deliver a professional client experience. All from one platform. So instead of bouncing between five different tools to send a proposal, get a contract signed, schedule a call, and invoice a client, they can do it all in one place.

What sets us apart? A few things.
First, we’re self-funded. Always have been. We’ve never taken venture capital, which means we answer to our users, not investors. Every decision we make is about what’s actually best for the people using the product, not what looks good on a growth chart. That matters to me. A lot.

Second, we actually care about how our product makes people feel. I love focusing on the experience. Whether it’s the experience someone has walking into my home or the experience a business owner has onboarding their first client through Dubsado. It should feel seamless. It should feel like you’re being taken care of. The little details matter. That’s baked into everything we build.

Third, I think we genuinely understand our users because we’ve been them. I was a photographer struggling with the exact problems Dubsado solves. Jake built this for me before it was a company. That origin story isn’t just marketing. It’s why empathy runs through everything we do.

What am I most proud of? Honestly, the community. We’ve served hundreds of thousands of creative entrepreneurs over the past 10 years. These are people who bet on themselves and decided to build something of their own. That takes guts. And getting to be a small part of their journey, helping them look professional and stay organized so they can focus on the work they actually love, that’s everything.

We just hit a milestone recently: 100 updates shipped in a single week. After spending two and a half years rebuilding our platform, we’re now moving faster than we ever have. The energy on our team is completely different. We’re building the product I always dreamed Dubsado could be.

If there’s one thing I want readers to know, it’s this: running a business is an adventure. It’s not easy. But it’s worth it. And you deserve tools that actually support you on that journey, not add to your stress. That’s what we’re here for.

Can you talk to us a bit about the role of luck?
I’ve thought about this a lot, and I’m honestly not sure how much of it is luck versus just showing up consistently and being willing to figure things out.

Was it luck that Jake happened to be a developer who could build the first version of Dubsado? Maybe. But he also spent years learning those skills. Was it luck that I was a photographer who desperately needed better systems? I guess. But that frustration came from actually being in the trenches trying to run a business.

I think what looks like luck from the outside is often just timing meeting preparation. We started Dubsado at a moment when more people were becoming solopreneurs and realizing they needed tools to manage their businesses. The gig economy was growing. Creatives were going out on their own. We didn’t plan that. But we were building something that happened to meet a real need at the right time.

If I’m being honest, I think the “bad luck” moments have shaped me more than the good ones. The seasons where everything felt like it was falling apart. The culture challenges we faced. The times I doubted whether I had what it takes to lead a company. Those moments forced me to grow in ways I wouldn’t have otherwise.

There’s a quote I think about sometimes. Something about how the harder you work, the luckier you get. I don’t love the hustle culture implication of that, but there’s truth in it. We’ve been at this for 10 years. We’ve stayed self-funded when people told us we couldn’t compete without raising money. We rebuilt our entire platform when it would have been easier to just keep patching things. That’s not luck. That’s stubbornness and conviction.

But also, I’m incredibly grateful. For Jake. For Biz, my best friend who now helps me run this company. For the team we’ve built. For the users who stuck with us. If luck means having people in your corner who believe in what you’re building, then yeah. I’ve been pretty lucky.

Pricing:

• Starter Plan: $35/month USD
• Premier Plan: $55/month USD

Contact Info:

• Website: https://www.dubsado.com/
• Instagram: https://www.instagram.com/dubsado/
• LinkedIn: https://www.linkedin.com/company/mydubsado/