“Just Say Yes, You’ll Figure It Out” 

Sometimes an idea doesn’t go anywhere. But this one did

Writing the story of our journey wasn’t something I (Sara Orsborn) ever imagined doing. But recently, while overseas on a work trip—with a bit of R&R at the end—I met a woman who was genuinely curious about MyTrucking. She asked me, “Have you ever thought about writing some of this down? Your learnings, your failures, your wins?” 

That question stuck with me. So here it is. The journey of me, I guess, – and MyTrucking. Not polished or perfect, but real. Because sometimes, the most unexpected ideas turn into the most meaningful journeys. 

It’s been 11 years since we started growing this little tech business. What began as a simple idea to help a transport operator manage things more easily has grown into something far bigger than we ever imagined. We’ve faced setbacks, celebrated wins, and learned more than we ever thought we would—not just about tech, but about people, resilience, and what it means to build something that matters. 

I’m a rural girl from Mahia Peninsula. I went to the local Te Mahia primary school and then headed off to boarding school in Hawkes Bay. After that, I studied a Business Studies degree at Massey University, majoring in Agribusiness, and completed a postgraduate diploma in Marketing. 

Straight out of university, I landed a graduate role at Richmond Meat Company. On day one, I was handed white overalls, gumboots, and a hairnet — and sent straight to the slaughter floor for six weeks. I was horrified! But I stuck it out and rotated through every part of the business — from the freezers and boning room to load-out and finally the office. It was a gritty, hands-on start to my career, and I wouldn’t change it for anything.  

Lesson #1: “Start at the ground level. Understand every part of the business. It gives you perspective you never lose.” 

After 12 months, I moved into a marketing assistant role, then took a leap into a marketing executive role at a global meat company, Bernard Matthews. It was a huge step, and I was lucky to have a manager who encouraged me to go for it. I ended up managing customers across Australia, the UK, and the US — travelling a lot, learning even more, and often being the only young woman in a very male-dominated industry, the meat industry. 

Lesson #2: “I just kept saying YES. Even when I didn’t know how to do something, I’d learn how to figure it out.” 

After 4 years in that role, I wanted to do something for myself. I started a marketing consultancy and event management business, and moved to Wairarapa to be with Sam, my husband to be. I also had a commercial property management business on the side — quite a diverse mix, but again, I learned a lot. 

Also, jointly with a good friend, we started a women’s networking event called Bubbles & Inspiration. It ran for 10 years and grew from 20 women to 200, with events every two months. It was a great way to connect with other women — business owners, mums, and anyone juggling life. 

Around the same time, I started helping with Sam’s family business, Sharpes Stockfeed, in Marketing and Sales. Sam had built over the years a simple Microsoft Access system to streamline the family business operations. Later, some good mates of Sam’s bought a local transport company and asked if he could build something like what he’d done for the stockfeed business—something to help them run more efficiently. So, he did. He built an Access database tailored to their transport needs. They used it for years, and word started to spread. 

Sometimes an idea may not eventuate into anything… but this one did. 

We got a quote from a local tech company and launched MyTrucking into the cloud. That was 11 years ago. Our goal in year one was 10 customers—we got 25. We worked from the kitchen table, then a cabin, a portacom, a house, a converted container, and now, a dedicated office. 

In the early days, we didn’t have a mobile app—just a web app. But we had a gut feeling that a driver mobile app was the next step. When we asked our early customers, most said, “Nah, we’ll just ring our drivers or print out the day sheet.” But we built it anyway. 

Lesson #3: “This is what innovation is — thinking ahead and seeing what’s possible before it’s obvious.” 

When you start a business, you’re involved in every part of it. From day one, we were doing it all – sales, marketing, partnerships, customer support, and product planning.  

We’ve been lucky. Sam and I are a good team. Sam has a passion for product and the tech side, and I’ve always had a passion for sales and marketing. We seem to complement each other, and it has worked well in our businesses. Often in tech businesses, companies can start with a strong product focus but haven’t got the marketing side set up. I guess that’s where we’ve been lucky — we’ve done both, right from the start. 

One of the big things early on was coming up with our company values. It’s something that can feel hard to define, but it’s been one of the most important things we’ve worked through. Our values guide everything — from how we build the product to how we support our customers and grow our team. At MyTrucking, our values are simple: Customer, Simple, Efficient, and Family. 

Customer referrals have always been our number one source of growth. After 11 years, it still stands out as the most powerful way we’ve grown. We’ve tried and tested all sorts of marketing channels, spent money on different campaigns and tools, but nothing has ever come close to the power of a happy customer telling someone else, “It’s awesome.” That kind of trust is gold — and something we never take for granted. 

We originally only registered the domain name mytrucking.co.nz, thinking we’d only be in New Zealand. But as we expanded, we realised we needed the .com domain — but it was already taken by someone in the US. It was a classic startup mistake. Luckily, we managed to track down the owner in the US and negotiated a purchase for $1500 USD. It was a huge win for our brand. 

Expanding into Australia was scary

There were weeks of cold calling, long road trips, late nights, and early mornings. We drove thousands of kilometers, meeting people, listening, learning. It was exhausting — but it helped us understand the market, refine the product, and see just how differently every business operates. That experience shaped how we built MyTrucking and how we support our customers today.  The support of NZTE (New Zealand Trade and Enterprise) was hugely helpful in this phase — helping us navigate and build connections. 

Another key factor in our journey has been the numbers. It’s always important to crunch the numbers. Sam was previously a farm consultant for 10+ years, and we’ve been very lucky to have his skills on the financial side of things. 

Over the years, plenty of people have encouraged us to consider capital funding. We’ve never been keen—and sure, we probably could have grown faster—but we’re proud of the path we’ve taken. We’ve grown steadily, added great people, built better systems, and stayed true to our values. Today, we’re a team of 25. But for us, it’s never been about headcount—it’s about building smart systems, working efficiently, and putting people and customers at the heart of everything we do. 

Lesson #4: “Growth isn’t just about speed—it’s about direction, discipline, and staying true to what matters.” 

Over the years, I’ve learnt by staying curious and giving things a go. I do like to experiment, try new things, and I’m always looking for better ways to do things. Whether it’s through chatting to others, podcasts, blogs, or reading on LinkedIn, I’m constantly hunting for those small golden nuggets, and still learning every single day!
 
One of the biggest challenges of being a founder is, you’ve touched every part of building it from the ground up, made the key decisions, and know the story behind every system and process. That depth of involvement makes it hard to step back—but it’s a necessary part of the journey. With a great team around us, I’ve been able to shift my focus more toward marketing and growth, while still staying connected to the heart of the business. 

Our go-to apps

In the early days, we did all our support by phone and email. Then we came across Intercom – a customer support tool, and it’s been a game changer for us. We’ve always loved Intercom, and I get genuinely excited every time they launch something new. It has enabled us to grow and deliver the excellent support we pride ourselves on. I’m not so involved in the day-to-day of Intercom anymore, but I still tune into every podcast and release—they continue to inspire me. 

Right now, my go-to app is Copilot AI. I use it constantly—sometimes instead of bugging Sam, or the team, I just plug my questions into Copilot. It helps me think things through and gives me the inspiration to keep going. If you haven’t embraced AI yet, or you’re still sitting on the fence—just do it. It’s a game changer. 

We use a lot of apps: PipeDrive, Slack, Xero, Figured, GoCardless, Stripe, Jira, Confluence, Office365, Semrush, Ahrefs, Yoast, Zapier – and more. One Christmas break, I played around with an amazing app, Zapier, after hearing about it on a podcast. That little experiment turned into something we now use daily to connect our systems. It’s been a real game changer app, as it can pretty much connect anything!

Lesson #5: “Progress doesn’t come from knowing everything—it comes from being willing to try, learn, and adapt.” 

About six years into the journey, we did a brand refresh—not a full rebrand, but a visual and messaging update. It gave us a fresh boost and helped modernise our look and feel while staying true to our roots. 

One of the biggest learning moments on the marketing side came when our Facebook page was hacked. Seven years of building a strong following across New Zealand and Australia—gone overnight. A hacker took over, sold underwear on it, and ran ads using my credit card. I tried everything to get it back. No luck. We had to rebuild from scratch. It was a huge setback, but we did it. And we learned a lot. 

Lesson #6: “You don’t realise how strong your brand is until you have to rebuild —and your community pulls together to help.” 

We now have customers across New Zealand, Australia, and the UK — and we’re still growing month by month. We’re about to explore the UK market even further, and it’s exciting to see what’s ahead. 

Alongside all this, Sam and I have three kids—now teenagers—and we’re also juggling two other businesses in the rural sector. The lessons we’ve learned across each business often overlap. Whether it’s systems, people, or problem-solving, we find ourselves applying those learnings across the board—and even into everyday family life. It’s all connected. 

If you’re starting a business, already in one, or just thinking about it—know this: it’s hard work. Really hard. But the rewards? They’re so worth it! 

As an owner, you carry the weight of everything. It’s not an 8 to 5 job. You’re thinking about the numbers, dealing with customer calls (sometimes grumpy ones), stepping in when team members are away, handling payroll, paying bills, networking, and fielding ideas from all directions. There’s a lot that goes on behind the scenes that people don’t always see. 

Lesson #7: “You don’t need to have it all figured out. You just need to begin—and be willing to keep going.” 

From domain name hiccups to social media disasters, expanding into new countries, and building a tech business from a rural town in the middle of a paddock—the MyTrucking journey has taught us so much. 

If you’re building something of your own, I hope these lessons help you avoid a few potholes along the way.

“Just say yes. You’ll figure it out!” 

ABOVE: Sara & Sam – celebrating 10 years of MyTrucking – April 2024