And then there was Aiza. I’d only met her recently—a beautiful morena from the Philippines with a quiet strength in her eyes. The first time I saw her, I knew. It wasn’t gradual; it wasn’t cautious—it was the kind of certainty you can’t explain without sounding foolish. At the time, she was working as a receptionist at Cushman & Wakefield in Bonifacio Global City—BGC for short—a modern, glass-and-steel commercial district that could take anywhere from one to three hours to reach from La Vista, depending on the caprices of Manila traffic.

Photo: Aiza and I on her birthday, Sept 2015

Traffic in the Philippines isn’t just an inconvenience—it’s a fact of life, a structural part of the day. If you live outside BGC or Makati, the main commercial hubs, every trip into the city is a commitment, often planned with military precision. On some days, Aiza’s commute meant leaving before sunrise and returning long after sunset.

Our relationship moved fast—recklessly, some would say. Three months after she moved in with me, she was pregnant. I was over the moon. I’d been ready for over a year—my own quiet longing to be a father had been building in the background, and here it was, suddenly real. So there I was: living in a mansion, with a driver, a maid, a cook, a pregnant girlfriend, and two dogs—Bruce, a big-hearted Labrador with the run of the place, and Bugsy, a lhasa apso x poodle who was small enough to fit in your arms but carried himself like he owned the block.

Photo: Bugsy, Bruce and Aiza in the living room at La Vista.

It was a far cry from my first startup years, in a run-down apartment building with peeling paint and a rusty gym in the basement that smelled permanently of damp iron and old sweat. Back then, every scrap of comfort had been earned slowly. Now, it was all here at once.

I didn’t see it then, but these niceties were making me soft. Not lazy—I’ve never been lazy at work—but soft in the way a fighter can be softened by comfort. The best boxers often come from harsh beginnings: rough, sometimes dangerous neighbourhoods, where meals aren’t guaranteed and the air hums with the tension of wanting something better. That environment breeds hunger. Once they’ve made it—once they’ve tasted the trappings of success—some lose that raw edge. The greats know this, and some will deliberately return to those harder environments before a big fight, just to remind themselves of the taste of struggle.

I still had drive, but it was cushioned now—muffled under the warmth of having money in the bank, staff to take care of the small frictions of daily life, and a house that made me feel more successful than my bank balance really justified. The hunger that had once felt sharp and urgent was quieter now, easy to miss in the comfort.

And beneath all that was the one detail I hadn’t yet reckoned with. I’d signed the lease while still with Frontier—twenty-four months, no escape clauses. At $1,300 a month (rising to $2,000 after two years) it was an absurd bargain for what it was. But bargains have a way of becoming burdens when circumstances shift—particulary when you realise the monthly electricity bill is almost the same amount as the rent. Once Frontier was behind me, the commitment loomed larger. The house was still my sanctuary—but it was also a golden cage, a reminder that my new chapter was starting with less flexibility than I’d hoped for.

Lesson (cost discipline): Peaks rarely last. You have to plan for the rainy days when the fees dry up. Businesses are exposed to so many externalities that can shake the P&L—politics, markets, regulation, and even a client’s change of leadership.

Back in business school, I was taught to run a PESTLE analysis and map out Porter’s Five Forces. At the time, I dismissed them as textbook nonsense, exercises to pad out assignments. But standing on the other side of a payroll cliff, waiting for contracts to land, I realised how important those tools really are. They aren’t about theory; they’re about building the habit of scanning the horizon—so you see the storm clouds before they break overhead.

Becoming Bold Native

By that stage, I knew one thing for certain: I wanted to be based in the Philippines for the long haul. I’d fallen for the place—not just the climate, the food, or the chaos of its streets, but the people I worked with and the rhythm of business here. I’d done consulting work for some of the country’s most established groups—Metro Pacific, Aboitiz, Ayala, the First Pacific Group, First Balfour—each a cornerstone in the nation’s corporate landscape. I found them good clients: decisive, sharp, and often surprisingly warm in their dealings.

I could see it clearly. A future here, deeply rooted. No plans of leaving, no “this is just a chapter” in my head. This was it. Which meant that if I was serious about staying, I needed to plant my own flag—build my name here, in the Philippines, not as a transient expat but as someone who belonged.

So I asked myself the most obvious question: What is it you can actually do?

The answer was right in front of me. I could do the kind of consulting work I’d done at Halcrow—technical, engineering-focused, feasibility studies, transaction advisory. I could also do management consulting, drawing on my experience with EC Harris in London, advising big corporations and navigating boardroom politics. Layer onto that the experience I’d gained as a founder at Frontier—the bruises and the lessons from building something of my own—and I could see the outline of a business taking shape.

It would be a blend: technical consulting grounded in infrastructure expertise, paired with management consulting for strategy, operations, and organisational improvement. The combination felt right. It played to my strengths.

But there was one problem. I hated the idea of doing it alone. For most of my career, I’d been part of a team—selling the collective capability of a group, not just myself. Selling my own CV as a product? That didn’t sit well with me. I wanted to be surrounded by strong CVs—people whose credibility I could champion to clients as part of a portfolio of services.

Enter Richard “Frosty” Frost—a very intelligent, methodical transport planner who was hilarious after a few beers and your “phone-a-friend” for Who Wants to Be a Millionaire? Frosty had come into Frontier right at the tail end of that venture and was keen to follow me into something new. He’d be based in the UK; he’d just married a Brazilian and settled into a new home. Moving halfway across the planet to found a new startup didn’t make sense. But he had tonnes of experience in the Philippines—he’d been there in the early ’90s with Halcrow before moves to the US and then Brazil for various projects.

Picking a Name for the Company

I have strong views on naming companies: it doesn’t matter what you call it, provided it’s not offensive. What matters is how you bring the name and brand to life. Brand agencies make a killing convincing companies that the name is important. Not once have I heard a VC say, “We’re not going to invest because your name isn’t good enough.” It’s bollocks. Pick a name and get on with it.

To choose the name for this company, I decided to run a fun, alcohol-and-hors d’oeuvres-powered workshop. In my world, a workshop meant flip charts, sticky notes, structured brainstorming. This one… was a little different. My “team” that day was our maid, our cook, our driver, and Aiza—my girlfriend then, now my wife. I honestly cannot recall if Frosty was there. I think not—he tended to fly over only for trips paid for by business; he may well correct me.

Frontier had been about pushing into new frontiers. But that was a different phase of my life. I didn’t want to be the outsider coming in to break new ground anymore. I wanted to be seen as a native, embedded in the place, part of the fabric.

We went back and forth, tossing ideas around. Then my driver, Patty, piped up:

“What about… Bold Native?”

I stopped. Bold Native. It landed instantly. I liked the sound of it. It said something about courage, about not just being in a place but belonging there. “Yes,” I told him. “That’s it. That’s the one.”

What I didn’t know—and no one volunteered to tell me until later—was that in Tagalog the phrase translated loosely into “naked native.” By the time someone finally mentioned it, the name had already stuck. It became a running joke that travelled with the company for years, and in a strange way, it made me like it even more.

Lesson (branding): Names are containers. Your execution, not your syllables, fills them with meaning.

Photo: working shopping in the grand hall of the home in La Vista

Incorporation Realities

We first established a company in the UK—because it was much easier. The Philippines scored very low on the ease-of-doing-business index; setting up a PH entity was a headache. Back then, to avoid forking out roughly $200k in paid-in capital, I needed a 3:2 formation—three Filipinos to two foreigners. The next challenge: find three Filipinos willing to own the majority on paper and sign side agreements that made me responsible for risks while retaining practical control of decision-making. This is the sort of nonsense you come up against in certain countries.

Through friends and Aiza I found the people I needed, and six months later we had a PH entity. The PH entity was crucial for serving local clients because of something called Expanded Withholding Tax (EWT). In practice, when you invoice a PH customer, the customer pays a portion of your tax directly to the government and remits the balance to you. At year-end there’s an assessment; you either pay more or claim back any overpayment. In reality—at least in 2016—you almost always overpaid and never saw the refund. (Things have improved; how much, I’m not sure. Do your own research if you’re thinking of setting up a company in the Philippines.) Not having a PH company while residing in the Philippines made it difficult for customers to interact with me. So it was a necessity. There were workarounds, but I pride myself on doing things by the book.

So, two companies set up. Ready for business.

Lesson (market entry): Build for how a jurisdiction actually works, not how a deck assumes it works. Align your corporate plumbing with buyer friction points.

Where’s the Business?

Whilst setting up BoldNative, with companies now established in both the UK and the Philippines, I was out chasing business. I turned first to clients I’d worked with before in Manila. The work with Encourage Capital—formerly EKO, after merging with Wolfensohn Limited—had come to an end. So I began knocking on old doors, and soon enough we were invited to bid on a project called the Plaridel Bypass.

It was classic transport-planning work: revenue forecasting, feasibility analysis, route alignment. I’d oversee a team of engineers and environmental consultants to assess the design, projections, and the social and environmental safeguards. Metro Pacific, a client I knew well and had served for years, looked certain to award us the contract. We submitted the proposal and waited. And waited.

Meanwhile, months ticked by. The money I’d taken out of Frontier was evaporating faster than ice water in the Manila heat. My son was due to be born in April, and this was already January with no income in sight. Aiza and I sat at our desk one evening, both silently wondering when our first break would come. On YouTube, a song played—A Great Big World, Christina Aguilera - Say Something.

“Say something, I'm giving up on you

I'll be the one, if you want me to

Anywhere, I would've followed you

Say something, I'm giving up on you”

We laughed at the timing, but the lyrics hit close to home. I had Frosty, a small equity partner, who needed a salary. A handful of young staff had transferred across and were already on payroll. I was carrying the cost of an expensive house and household staff. Overheads couldn’t have been higher. In hindsight, it was a terrible way to launch a startup—but sometimes you only learn by living through it.

Then, the very next day, word came in: Metro Pacific had awarded us the job—fees of around $120,000. The first payment landed, and suddenly the pressure lifted. We got to work. A couple of months in, the project hit a stall—not through anyone’s fault, just the usual politics and timing that come with infrastructure. But for us, that contract was everything. It was proof that BoldNative was alive, that we’d made it onto the board.

Lesson (pipeline): Single-threaded hope is not a strategy. Map your cash runway to decision cycles in your buyers’ world, not your own.

Birth, Work, and the Cost of Momentum

The delay on the Metro Pacific project created a slow, grinding pressure across everything—payroll, operations, and the dozens of little costs that never stop arriving. We had just enough in the bank to cover salaries and the essentials, but only just. It bought us time, not comfort. We needed more work—badly. With Harry’s birth getting closer by the day, I was out hunting for new projects, pushing harder, looking for any opening. But the work simply wasn’t coming.

Meanwhile, Aiza was enduring a very difficult pregnancy. The first trimester had been rough; the third was worse. We were in and out of hospital more times than I can count—so often it felt like a second home. I wasn’t at my best during this period. Trying to launch a startup while your girlfriend is struggling through a complicated pregnancy is a terrible combination, and the stress was relentless. We were holding everything together with hope, stubbornness, and the last of the cash.

On the night of April 4 2016, Aiza woke me gently after we had spent the whole day waiting for the right moment, and said, “I think it’s time—I need to go to the hospital. In Manila, the trip could take 30 minutes or three hours depending on traffic, so we had bags packed and ready. Patty, our driver, was on standby. He drove us straight to St. Luke’s Hospital in Bonifacio Global City.

Shortly after we arrived, Aiza’s water broke. After ten hours of labor, the doctor told us a C-section was necessary. I held her hand throughout the procedure - excited, scared, and worried all at once and then Harry was born. I cried my eyes out—properly—like any good dad would. And he arrived with a curveball: a bright blue bottom. I had no idea that was common with Asian mixed-race kids; it was news to me in the moment and, frankly, hilarious. I was so wrapped up in the joy of holding him, taking photos, and soaking in those first moments that I forgot Aiza was still on the operating table because of an internal haemorrhage. When I went back into the room, she looked at me and said, “I haven’t even seen him yet.” That brought me straight back to earth.

We were moved upstairs. Aiza was resting in bed, Harry sleeping beside her, the room finally quiet after the chaos. And then my phone buzzed—my good friend Elka. She had a potential job: an EU bid, an EU project that needed help. Could I start now? We needed the money, so there wasn’t a decision to make. Within sixty minutes of Harry being born, I was sitting in a hospital chair next to Aiza’s bed, laptop open, working.

Elka flew over two or three days later. I don’t think she stayed at the house—pretty sure she booked a hotel just around the corner—but either way, we got to work immediately. For the first two weeks of Harry’s life, I worked continuously throughout the day. Frosty flew in to help as well. I caught glimpses of my son—little pieces of him between calls and drafts and deadlines—but I missed most of those first moments. It was highly stressful for Aiza, and I would never recommend anyone put themselves through that. Thankfully, her mum was there to help, which was a real relief, but still: I missed it. Those early days were gone, and I’ll never forgive myself for that. It’s one of those things founders sometimes go through—paying for the privilege of building something with moments you’ll never get back—but knowing that doesn’t make it easier.

After that initial two-week sprint, the pace shifted a bit and I finally got to spend more time with Harry. And then, mercifully, the business turned. We secured Elka’s project. Then Metro Pacific came through. Then First

Pacific. Then Aboitiz. These names won’t mean much to most people outside the Philippines, but they’re tied to three of the largest families in the country—groups that operate across almost every infrastructure sector. For a firm like ours, it was the signal we needed. We went from clinging on to full attack mode.

That year we worked on ten, twelve—maybe fifteen—transactions. It was a phenomenal run. We expanded the team. The energy was electric. We were guns blazing, and for a while it felt like the only direction was up.

More to come in My Founder Journey Part 5…

If this story resonates, or if you’re navigating your own founder journey and need someone to talk it through with, I’d love to hear from you. Drop me a line at bensheppardxyz@gmail.com