Why Your First Hire and Your Tenth Hire Need Different Rules

Most founders apply the same hiring instinct at every stage of growth, and that instinct usually stops serving them somewhere around hire number four or five. Hiring isn't one decision repeated, it's a sequence of different decisions that each require a different approach. In a recent conversation on my podcast, this idea was laid out clearly, stage by stage, in a way that reframed how I think about team building.

There's a strong case for remote and nearshore talent almost everywhere in a growing business, except at the very beginning. Early-stage decisions happen through fast, informal, in-person context, the kind of conversation that shapes culture and direction in ways a scheduled call rarely captures. Your first few hires, especially anyone with executive potential, benefit from physical proximity in a way that later hires simply don't need.

Capital used to move fast. Startups could reasonably expect to raise again within 18 months, and hiring plans were built around that rhythm. That timeline has stretched considerably for anything outside a narrow set of hot sectors, which means the old approach of hiring aggressively between funding rounds is riskier than it used to be. Founders need a hiring strategy that can survive a longer runway, not just a shorter one.

Brian Samson, founder of a Latin America-focused staffing company, described nearshoring's real advantage as two-fold when we spoke: significantly lower cost than local hiring, combined with overlapping working hours that keep collaboration genuinely synchronous. A question that would take a week to resolve over asynchronous email can be solved in a single call when both sides are awake and available at the same time. That's a meaningfully different working rhythm than hiring across a twelve-hour time difference.

It's tempting to assume the best talent comes from the most stable environments. In practice, people who've had to navigate genuine volatility, economic, political, or otherwise, often develop exactly the resourcefulness and comfort with ambiguity that early and mid-stage companies need most. Highly stable environments can quietly produce less adaptable talent, simply because adaptability was never required.

For a first few international hires, freelance platforms are a reasonable way to learn how remote collaboration actually works. But once you're scaling past a handful of hires, a specialised recruiting partner becomes worth the investment, bringing established networks, vetted candidates, and trust that's difficult to build from scratch on your own.

There's no single right way to hire, there's a right way to hire at each stage. Get your early core team in the room together, then build outward with the flexibility, cost efficiency, and resilience that nearshore talent increasingly offers.