The Cold Call That Turned Into an 80-Person Company

Most founder stories about moving abroad start with a plan. Brian Samson's started with a Skype call to a guy in Shanghai he barely knew, asking if he could come work for him, and getting told no because he didn't speak Mandarin. Host Jet Bunditwong pulled that story out of Samson on a recent episode of The Personal Side of Business, and it's a much better explanation of how nearshoring actually gets built than any pitch deck could offer.

Bunditwong runs The Personal Side of Business specifically to surface these kinds of stories, the real, unpolished path behind a company rather than the highlight reel. His conversation with Samson, founder of Plugg Technologies, traces exactly how a rejected pitch to move to China turned into a fintech-focused MVP shop in Buenos Aires, and eventually a full nearshoring business built on everything Samson learned navigating Argentina's notoriously difficult bureaucracy.

Samson has spent 11 years in nearshoring since that first move, and has made more than 500 placements connecting Latin American professionals with U.S. companies. He has built three companies to $4 million in annual recurring revenue each, and the Argentina venture Jet asked him about grew from a two-person plan to 80 engineers before Samson exited. He's now based in Hawaii, but the lessons from those early years in Buenos Aires still shape how Plugg Technologies operates today.

Getting Rejected From Shanghai Led to Buenos Aires

Samson told Jet Bunditwong that his path to nearshoring wasn't a straight line, it was a rejection followed by an improvisation. He wanted to become an expat in Asia and cold-called a former colleague running a company in Shanghai, only to be told his lack of Mandarin was a nonstarter. The colleague's counteroffer was simple: come back with a real business idea, and maybe.

Samson landed on a thesis around fintech companies in San Francisco. These startups had capital and product vision but no efficient way to build a minimum viable product, so he pitched building an MVP shop that could serve them. The pitch worked, he secured roughly $2 million in funding, but building the software team back in San Francisco didn't make financial sense. He needed a location, and rather than defaulting to Asia, he picked Argentina based on a solo backpacking trip he'd taken years earlier.

Jet Bunditwong asked what his wife was doing at the time, and Samson explained she was already winding down a career in talent and academia, which made the leap easier logistically even though, as he put it, Argentina wasn't the Asia she'd originally signed up for. That detail matters because it shows how much of this decision was opportunistic rather than strategic from day one, a theme that runs through the entire episode.

The Bureaucracy Story That Explains Why Nearshoring Is Hard

The most memorable section of the conversation is Samson's account of registering a business in Buenos Aires. His attorney, a man named Mariano with 25 years of experience, warned him upfront that what takes four hours in a country like Singapore might take four months in Argentina, and that even then, approval wasn't guaranteed. Samson didn't believe him until he watched Mariano, a seasoned professional, visibly nervous walking into a bureaucratic office with a full binder of paperwork.

The appointment was denied on the spot for a missing power of attorney form, despite Samson standing right there in person with his passport. The absurdity of the moment, needing a form that grants someone else authority to act on your behalf when you are physically present to act on your own behalf, captures exactly the kind of ambiguity Samson says defines doing business in the region. He was candid that some kind of resolution eventually happened between Mariano and the official, without specifying details, and the approval came through not long after.

Samson also described a related, more practical lesson: Argentina runs largely on cash rather than credit, because trust in contracts and institutions is low. A deal that would be completely normal in the U.S., delivering goods against a 30-day invoice, doesn't work the same way there. If you want the product, you need the cash ready that day. It's a small detail, but it's the kind of operational knowledge that only comes from actually doing business on the ground, which is exactly what Plugg Technologies was built on.

First-Time Founder Ego Is a Real Cost

Jet Bunditwong asked Samson directly whether there was ever a point where he considered the whole move a mistake. Samson's answer was refreshingly honest: as a first-time founder, ego made that question almost impossible to ask himself in the moment. He had told his peers what he was doing, had skin in the game, and treated every obstacle as something to brute-force rather than reconsider.

Jet picked up on the personal dimension underneath that stubbornness, suggesting it was less about proving something to peers and more about not wanting to go back to his wife and admit the move had been a mistake. Samson didn't disagree. He now looks back at that period as a source of funny stories, but acknowledged that a second or third-time founder would likely have made different, more flexible decisions. It's a useful admission for any entrepreneur currently white-knuckling their way through a hard decision: sometimes what feels like determination is really just the inability to admit a sunk cost.

Reframing "Chaotic" Countries as a Talent Advantage

One of the more thoughtful moments in the episode came when Samson pushed back on how Americans tend to perceive countries in Latin America. He pointed out that cartels in Mexico or currency collapse in Venezuela are the product of leadership failures, not something the general population caused, yet those headlines shape how outsiders judge an entire workforce.

Samson's argument is that living in a genuinely unpredictable environment builds real skills: flexibility, adaptability, and resourceful problem solving, the exact traits any employer would want on a team. He connected this directly to customer service quality, contrasting it with the scripted, rigid support style common at some offshore Asian call centers, where a call that veers outside the script can quickly frustrate an otherwise loyal customer.

Jet Bunditwong had his own version of this experience to share. "I've been on customer service calls in, let's say, like Mexico City, and that person actually has lived in California at one point. So there's that connection," said Jet Bunditwong, describing how that shared cultural context made it easier for the representative to understand his tone and the actual problem he was calling about, rather than forcing the conversation into a rigid script.

Samson tied this back to the math companies run internally, joking that some firms calculate they'll save a large sum on offshore labor while quietly absorbing an almost equally large loss in customer churn from frustrated interactions. Nearshore support in a shared time zone and cultural context, in his experience, avoids a lot of that hidden cost.

Nearshore Talent Isn't Just Virtual Assistants

A recurring point in the conversation is that nearshoring gets pigeonholed as a virtual assistant service when it's capable of much more. Samson described hiring full managers and team leads through nearshoring, not just individual contributors, and shared a specific example: waking up in Hawaii to an email chain where a customer issue had already been identified and resolved by his nearshore manager hours earlier, without Samson ever being looped in until it was already handled.

Jet Bunditwong summarized the deeper implication well. "This is having someone as a part of your team. They're just not in the US, so this is like a part of your business family in sense," said Jet Bunditwong, capturing the shift Samson was describing from transactional outsourcing to genuine team integration.

Samson's advice for anyone building out a nearshore hire, whether through Plugg Technologies or another agency, is to run the same interview and onboarding process used for a domestic hire. Treating nearshore team members as interchangeable low-cost resources, rather than as people who can grow into leadership roles, is the fastest way to underuse the talent available.

How to Get Started

Based on what Samson covered with Jet Bunditwong, a founder considering nearshore hiring for the first time should approach it in stages.

1. Start small if you're new to this. Platforms like Fiverr and Upwork are reasonable starting points for a first virtual assistant hire, even though talent tends to move off those platforms as engagements grow longer.
2. Research the specific country, not just "Latin America." Costa Rica and Nicaragua are neighbors but differ enormously in cost, English fluency, and ease of getting equipment across borders. The right market depends on the role.
3. Treat the hiring and onboarding process like any domestic hire. Run real interviews, invest in onboarding, and think of nearshore team members as an extension of your team rather than a lower-cost substitute.
4. Get a customer before you polish everything else. Samson's clearest regret from his early years was spending time refining an LLC structure and website copy before he had a paying customer. Solve a real problem for someone first.

The Bigger Point

What comes through in this conversation is that nearshoring worked for Samson not because he planned it perfectly, but because he stayed adaptable through a rejected pitch, a bureaucratic maze, and a first-time founder's stubbornness. The traits he eventually learned to value in Latin American talent, flexibility, resourcefulness, and grit under pressure, are the same traits that got him through building the company in the first place.

🎧 Listen to the full episode: Brian Samson on The Personal Side of Business 🔗 Learn more about nearshore hiring: plugg.tech 🎙 The Nearshore Cafe Podcast.

Frequently Asked Questions

What is nearshoring and how is it different from offshoring?

Nearshoring means hiring talent in a country close enough to share most of the workday, while offshoring typically means crossing an ocean and a significant time zone gap. Brian Samson of Plugg Technologies explains that for U.S. companies, offshoring usually means Asia while nearshoring usually means Latin America, though the labels shift depending on where a company is based.

Why do U.S. companies prefer nearshoring Latin America over offshoring to Asia?

Workday overlap is the main advantage, allowing real-time collaboration through calls and messages instead of delayed email exchanges. Brian Samson also points to cultural familiarity, noting that many Latin American professionals are deeply familiar with U.S. media and communication styles, which reduces the friction that can occur with scripted, less flexible offshore support models.

What roles can be nearshored beyond virtual assistants?

Brian Samson emphasized on the episode that nearshoring covers far more than administrative support. Companies hire nearshore software developers, marketing specialists, operations managers, and even full team leads and department heads. He described personally hiring nearshore managers capable of running teams and resolving customer issues without daily oversight.

How much can a company save by nearshoring instead of hiring in the US?

Brian Samson estimated cost savings can reach 50 percent or more compared to equivalent U.S. hires, though he cautioned against treating cost as the only factor. He described how some companies save heavily on offshore labor costs but lose a comparable amount in customer churn from frustrated service interactions, making total value a better measure than hourly rate alone.

What challenges come with registering a business in Argentina?

Brian Samson described Argentina's business environment as full of bureaucratic ambiguity, sharing a story about a business registration that was expected to take four hours but instead took months, and was initially denied over a missing form despite Samson being present in person. He also noted that business in Argentina often runs on cash rather than credit due to low institutional trust.

What does Plugg Technologies help companies do?

Plugg Technologies, founded by Brian Samson, helps U.S. companies identify the right Latin American country for a given role and manages recruiting, hiring, and onboarding for nearshore talent. Samson advises companies to treat nearshore hires with the same interview and onboarding rigor used for domestic employees rather than viewing them as low-cost, replaceable resources.

Brian Samson is the founder of Plugg Technologies and host of The Nearshore Cafe Podcast. This post is based on his appearance on The Personal Side of Business.