Want to start an online business but feel like there aren’t enough hours in the day? What if you could build a successful digital business while working full-time and raising young children?
Meet Jason and Sally, a remarkable couple who transformed their evenings from Netflix sessions into entrepreneurial success. Despite juggling 50-hour corporate workweeks and raising three kids under 10, they’ve built multiple thriving online businesses – including an award-winning wine podcast that’s attracting major industry sponsors.
In this inspiring story, you’ll discover how they went from complete digital beginners to winning the eBusiness Institute award for “Best Website Build of the Year” within just 12 months. Their journey reveals:
- The practical strategies that took their first website to Google’s front page
- How they turned their wine passion into “The Wined Up” – a podcast now attracting celebrity guests like Merrick Watts
- Their innovative approach to building a digital agency that has clients happily paying $5,000+ per project
- The mindset shifts that helped them overcome self-doubt and recognize their true value
- Smart partnership techniques that helped them scale despite limited time
Whether you’re a busy professional, a parent juggling multiple responsibilities, or someone who thinks they lack the technical skills to succeed online, Jason and Sally’s story proves that with the right approach, anyone can build a successful online business.
Discover how they did it – and more importantly, how you can too.
From Corporate Life to Digital Entrepreneurs
“I had no experience. I don’t do much on the computer besides my corporate role,” Sally recalls of their starting point. As a full-time mom juggling a corporate career with managing three young children aged 4, 8, and 10, the idea of building websites seemed far outside her comfort zone.
Jason, working 50-60 hours weekly in a senior operations role, was equally new to the digital world.
Building websites is not something that I’d frequently do. Often what I’d be asked to do is help Sally’s parents with their iPhone issues
But the couple had one advantage that proved crucial – they both worked primarily from home, with Sally remote four days a week and Jason in a similar arrangement. This flexibility, combined with their determination to build something of their own, gave them the foundation they needed to begin their digital journey.
Building Their First Success: The Wined Up
Rather than trying to master everything at once, Sally and Jason started small, building their first website for a family member’s business. This initial project allowed them to test their new skills in a low-pressure environment. Within seven months, they had successfully gotten the site ranking on the first page of Google for local search terms.
This early win gave them the confidence to pursue a bigger passion project – The Wined Up, a podcast and website dedicated to making wine more approachable for everyday enthusiasts.
We feel that the wine world can seem so complicated, it can seem a bit snobby, and there just feels like there’s this gap around how can we make it more approachable
Their timing and approach proved perfect. Wined Up quickly gained traction, attracting major wineries as directory clients and landing interviews with prominent figures like Merrick Watts, a well-known radio personality and wine enthusiast. The site went on to win “Best Website Build of 2024” at the eBusiness Institute awards.
Scaling Through Strategic Partnerships
One key to their success was recognizing they couldn’t do everything alone. They partnered with another couple – also juggling corporate careers and young children – to divide responsibilities across the team. While Jason and his business partner handle podcast interviews, Sally manages the digital infrastructure and directory, and their partner’s wife runs social media and networking.
“We found that this team that we have together has just worked quite well in kind of complimenting each other’s skillset,” Jason notes. This collaboration allowed them to build a substantial business despite everyone’s time constraints.
From Side Hustle to Digital Agency Success
Alongside Wined Up, Sally spearheaded the launch of their digital agency. Initially charging $2,000 for website builds, a pivotal mindset shift occurred after consulting with their business coach. When encouraged to raise their rates to $5,000, Sally was hesitant: “I was already scared to charge $2,000…but Greg’s like, ‘No, you’ve got to charge $5,000.'”
The result? Their next client accepted the $5,000 quote without hesitation. This experience taught them valuable lessons about properly valuing their skills and the importance of mindset in business growth.
Making Time for Success
Perhaps the most remarkable aspect of Sally and Jason’s story is how they managed to fit everything in. Their secret? Ruthless prioritization and a willingness to let go of perfection.
Sometimes just have to put that aside and do more important stuff, rather than folding the clothes or doing the house chores, I’ve put that aside and actually just sit down at end of the night and start working every single night.
Jason adds, “Normally we’d be on Netflix or something like that. Sal would be watching a Korean drama late through the night, but now it’s like put the kids down. Sal would wake me up so we can get to work.”
Leveraging Technology and Talent
After ten months of building everything themselves, they finally began hiring help through Upwork. They now work with three technical contractors and a content writer, allowing them to scale their business more efficiently.
This move to outsourcing proved transformative. “When you get a person from Upwork and he, a tech does it and he does all the touchup, at least you can correct him and say this is wrong,” Sally explains. “You get so much more leverage that way.”
Key Lessons for Starting an Online Business
Sally and Jason’s journey offers valuable insights for anyone looking to start an online business while managing other commitments:
- Start small and build confidence through early wins
- Partner with others to leverage complementary skills
- Don’t undervalue your services – charge what you’re worth
- Be willing to sacrifice some personal time initially
- Outsource strategically once you’ve mastered the basics
Their story proves that with the right approach, even the busiest professionals can build successful online businesses. As Jason reflects, “If we didn’t hear these stories, I don’t know if I would’ve probably self-sabotaged and said, let’s not have this opportunity.”
The key is getting started, even if you can only dedicate a few hours each evening. As Sally and Jason have shown, those small pockets of time, when used strategically, can build something remarkable.
