The image above is courtesy of one of my kids Leo, who wanted to throw Gondola some love.

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There's a particular kind of energy that comes with building something from nothing. It's not the energy of achievement or arrival - it's the energy of becoming. Of watching an idea that existed only in conversation transform into something real, tangible, and increasingly inevitable.

I'm writing this from the thick of it: nearly a year since founding Gondola, when everything is still being shaped, when every conversation might change our trajectory, when the team is small enough to fit around a single table but ambitious enough to reimagine an entire industry.

And I have to tell you - this is the fun part.

Assembling the Team

The early days of a company are essentially a long process of asking people to believe in something that doesn't exist yet. You're selling a future that lives only in your head, and you're asking talented people to bet their time, their money, or their reputation on your ability to make it real.

Ruby, my wife, was the first and most important recruit. Before anyone else could believe in Gondola, she had to believe in it - and in me. She had to be willing to risk a good income, watch us torch our savings, find a job of her own whilst juggling three kids, all to pursue this vision. That kind of conviction doesn't come from a pitch deck. It comes from something deeper: a shared belief that some things are worth the sacrifice.

Then came my parents. Their support has been unwavering from the very beginning - believing not just in Gondola, but in me. They've backed this vision in ways both tangible and intangible, and without their support, none of this would have come to life. When you're asking people to believe in something that doesn't exist yet, having your parents stand behind you with complete conviction gives you a foundation that's impossible to overstate.

Then came Adam - not just a qualified customs broker who understood the industry's pain points from the inside, but a trusted former colleague who shared the same values and the same commitment to serving customers well. He'd lived the frustrations of legacy systems.

But Adam didn't say yes immediately. In fact, he said no. Twice.

Each time, I came back with more conviction, more clarity about why it had to be him specifically. Not just any customs broker - Adam. Someone who understood the industry's problems, yes, but more importantly, someone I trusted completely to build something meaningful alongside me.

Looking back, I'm not sure whether his initial rejections were good negotiating skills on his part or whether he simply underestimated my persistence and conviction that it really had to be him. Either way, he eventually agreed to join the uncertainty of an unknown next pay cheque to build something better. That kind of conviction is contagious.

Then there was Nick - my brother, but also the CTO of a tech company with deep expertise in emerging technologies being applied in the procurement space. Nick had always been a strong supporter, but this time his contribution went beyond brotherly encouragement. He brought a technical lens that completely transformed how we thought about the opportunity. Where I saw customs clearance pain points, Nick saw how modern technology - especially AI and automation - could fundamentally reimagine the entire process. His perspective broadened our vision beyond simply digitising existing workflows to actually rethinking what customs clearance could become. Having someone who understood both the technical possibilities and believed in the mission added a dimension to our thinking that shaped everything that followed.

Then came Paloma. Out of 500 applicants, they backed just two ventures - and we were one of them. That validation opened doors. Not just financially, but psychologically. It told us we were onto something. It told others that serious, experienced people believed in what we were building.

Then came the early believers - advisors, industry experts, and supporters who saw the potential before we had anything to show. Not because we had traction or revenue, but because they could see the clarity of the vision, the strength of the team, and the size of the opportunity. Each conversation refined our pitch, sharpened our thinking, and expanded our network.

This is where you discover something profound about building a company: every person who joins your journey doesn't just add their individual contribution - they multiply the value of what you're creating. They bring their networks, their insights, their credibility. They make the idea more real, more credible, more magnetic to the next person considering whether to believe.

It's a flywheel effect. The first person who says yes makes it easier for the second. The second makes it easier for the third. Each addition to the team, each advisor who lends their expertise, each operator who agrees to pilot - they all add momentum. They all make the impossible seem a little more inevitable.

And then came the Advisory Partners - the logistics operators who were willing to work with us as we built. They're not just validating the vision; they're co-creating it with us. Every conversation surfaces new insights, new edge cases, new opportunities to build something genuinely better.

The Moments That Make It Real

But beyond the big milestones - the funding rounds, the partnerships, the first customers - there are smaller moments that mark the transition from idea to company. Moments that might seem trivial from the outside but carry unexpected emotional weight when you're living them.

The very first of those moments came on November 21, 2024, when we incorporated as… Hightail.

Hightail?!

Quick digression on the name story: I'd spent weeks landing on that name - it captured the speed and urgency we wanted to bring to customs clearance. We made it official, got the paperwork done, and started building under that banner.

Then came the trademark issues in March 2025. Hightail was already taken in ways that would create problems down the line.

Working with Adam and the Paloma team, we landed on Gondola within just a couple of days. The moment we said it out loud, it felt right - maybe even better than Hightail. Gondolas in the Swiss Alps carrying people through the air (air freight). Gondolas in Venice carrying people over water (sea freight). Gondolas in North America as empty rail carts (rail freight). Many modes of transport, captured in one word.

So we changed it. Filed the paperwork, updated the branding, and became Gondola in March 2025. That moment - when the idea became a legal entity, even if under a different name than we'd end up with - marked something significant. We existed.

End of digression. Back to November 2024:

After we officially incorporated as Hightail on November 21, Adam and I went back to the spot where we'd first agreed to pursue this venture together and raised a drink to what we were building. It felt right to mark the moment where it became official in the place where it had all begun.

Then came our first Christmas party that December - a sailing trip on Auckland Harbour with Adam. An experience that might have seemed like an extravagant expense for a bootstrapped startup. But here's what I've learned: you can't come back and celebrate these milestones later. You can't recreate the feeling of those early moments once they've passed. The investment in celebrating success and recognising the people who've made it possible has always felt worthwhile, even when money is tight.

I remember the first time I wore a Gondola-branded t-shirt. After years of wearing other companies' logos - proudly representing their brands, their visions, their missions - I was finally wearing my own. It's just a t-shirt. Just a logo on fabric. But it felt significant in a way I didn't anticipate. This thing we'd built had become real enough to exist in the physical world.

Then there was the first time I sent an expense receipt to our own finance email account. After years of forwarding receipts to other companies' finance teams, I was suddenly sending them to us. That simple email address represented something significant: we'd crossed the threshold from idea to infrastructure.

Then there was the day our landing page went live. Suddenly, gogondola.com existed. Anyone, anywhere could stumble upon what we were building. The idea had escaped from our small circle and entered the world.

Shortly after that came another milestone: publishing my first blog post about why we started Gondola. After months of building in relative quiet, it was time to articulate publicly what we'd been working towards - the problem we'd identified, the vision we were pursuing, and why now was the moment to reimagine customs clearance. Writing that post forced me to crystallise our thinking in a way that internal conversations hadn't. And hitting publish felt like another threshold crossed: we weren't just building anymore, we were beginning to tell our story to the world.

But perhaps the most thrilling moment was our first (of many!) inbound form submission. Not someone we'd reached out to. Not a warm introduction from an advisor. Just a complete stranger who'd found our website, read what we were doing, and decided to learn more. That single notification - "New contact submission" - validated something fundamental: other people, people who didn't know us, could see the same problem we saw and believe we might have the solution.

These moments might not appear in our investor updates or feature in our pitch deck. But they're the moments when you feel it viscerally: you're not just talking about building a company anymore. You're actually doing it.

The Cost of Conviction

Let me be honest about something that doesn't always make it into these kinds of stories: building Gondola has been expensive. Not just in time and energy, but in actual money.

I've torched a small fortune to bring us to this stage. The kind of investment that makes you lie awake at night doing mental arithmetic. The kind that requires explaining to your family why you're betting the house on customs clearance software. The kind that means saying no to things you'd rather say yes to, and making peace with a level of financial risk that would make a sensible person reconsider.

My son Bastian, who's 11, wants a phone for Christmas. I've had to tell him simply that we don't have that kind of money right now. But I've also sat down with him and explained what we're building with Gondola, and why it matters, and what we're working towards. And he understands. He's okay with it. He's on the journey with us.

That conversation - explaining to your own child why you're making the choices you're making - that's when the reality of what you're doing truly hits home. This isn't just my risk to manage. It's a family endeavour. Everyone around me is making sacrifices for this vision.

And yet, through all of it, I've never doubted what we're doing.

That's not bravado or blind optimism. It's something more fundamental. When you've found a problem worth solving, when you've assembled the right team, when you can see the path from here to there with clarity - the risk stops feeling reckless. It starts feeling like the only rational choice.

But here's what I've learned: you can't make this journey alone. Bringing people along requires being honest about both the upside and the cost.

When I convinced Adam to join me as co-founder, I wasn't selling him a guaranteed outcome. I was selling him on the potential upside balanced against very real risk and financial implications. Early startup life means uncertainty. It means constraints. It means betting on something that might not work. Adam understood that, weighed it, and chose to build alongside me anyway.

Our investors have made a similar calculation. They've had to develop comfort with risk and manage that alongside belief. Every pound they've invested represents not just capital, but faith - faith in what we're building, faith in our ability to execute, faith that the market is ready for what we're creating.

This is the part of the founder's journey that's hardest to explain to people who haven't done it. The simultaneous experience of financial anxiety and absolute certainty. The knowledge that you're asking everyone around you - family, co-founders, investors, advisors - to believe in something that doesn't exist yet, and to make real sacrifices for that belief.

We're extraordinarily lucky to have so many believers around us. People who understand that building something meaningful requires taking risks that sensible people might avoid. People who've chosen to be part of this journey, with eyes wide open about what it costs and what it might become.

The Industry as Co-Founder

One of the unexpected joys of this stage has been how much we learn from the industry itself. When you're building enterprise software, especially in a specialised vertical like customs clearance, your customers don't just buy from you - they teach you.

Every discovery call reveals something we hadn't considered. Every pilot surfaces a workflow we need to support. Every conversation with a customs broker or logistics operator adds nuance to our understanding of how the industry actually works, not how we assumed it worked.

This is where being small becomes an advantage. We can take a Tuesday afternoon conversation with an operator and have it influence our Wednesday morning product decisions. There's no bureaucracy, no layers of approval, no six-month roadmap carved in stone. Just a tight feedback loop between what we're hearing and what we're building.

The Speed of Small

I won't romanticise the challenges of being a small team with limited resources. The constraints are real and consequential. We're operating with limited runway where mistakes aren't just setbacks - they're existential threats.

But here's what I've discovered: those constraints create a level of financial discipline and focus that's harder to maintain once you're well-funded. Every decision matters. Every dollar counts. That clarity is exhilarating.

And there's something else - the speed and simplicity of our current size. We don't have meetings about meetings. We don't have committees or approval processes or political dynamics to navigate. We have a small group of deeply committed people who talk constantly, decide quickly, and execute immediately.

When we spot an opportunity, we move. When we identify a problem, we fix it. This agility - combined with a visceral reality of our runway - is our competitive advantage. It's one that diminishes as you grow, so we're extracting every ounce of value from it whilst we have it.

The End of the Start

2026 is the year we launch Gondola to Australia. The year we kick off our marketing campaigns. The year we formally engage with the industry bodies we've spent time building relationships with - FTA, IFCBAA, CBAFF. The year we launch our product to the market and present the results of our ambition, our risk, our vision, and the collective effort of our teams.

We're pumped.

We're at what I've started calling "the end of the start" - that pivotal moment where the foundation has been laid, the team assembled, the vision crystallised, and now we're ready to step into what comes next.

The next twelve months will bring challenges we can't yet see. We'll encounter obstacles we haven't imagined. We'll make mistakes and course-correct and learn and grow.

But right now, in this moment, what I feel most strongly is gratitude. Gratitude for the people who've chosen to build alongside us. Gratitude for the industry professionals who've opened their doors and shared their expertise. Gratitude for the investors who've backed us when we were just an idea and a pitch deck.

And beneath that gratitude, there's something else: excitement. Pure, uncomplicated excitement about what we're building and where we're going.

This is the builder's high. The feeling of constructing something meaningful from raw materials - code, conversations, conviction. The thrill of assembling a team around a shared vision. The satisfaction of watching abstract ideas crystallise into concrete product.

If you're thinking about starting something, or you're in the early days of your own journey, I hope you're savouring this stage. It's chaotic and uncertain and occasionally terrifying.

But it's also the best part.

And to everyone who's chosen to believe - to Ruby, to Adam, to our investors, to our advisors, to our industry partners, to our family and friends who've quietly supported us through every step, to my kids who understand why we're saying no to some things now so we can say yes to bigger things later - thank you. Your belief in what we're building isn't just appreciated. It's what makes this possible.

This journey belongs to all of us.

-  Johnny MacAvoy

CEO & Co-founder, Gondola