EPISODE · Mar 6, 2026 · 20 MIN
Scared to Hire Overseas
from Freelance to Founder · host Millo
Hannah is ready to make her first hire and is seriously considering looking beyond U.S. borders — but she doesn't know what she doesn't know. In this episode, Preston is joined by Brian Samson, a three-time founder who has scaled recruiting agencies to $4 million ARR by building teams across Latin America and beyond. Together they walk Hannah through exactly how to approach international hiring for the first time: where to start, which regions tend to excel at what, how to think about time zones, and the blind spots that trip up most first-time international managers — including the costly "follow-the-sun" communication trap that can burn a full week on a single misunderstood task. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices
What this episode covers
Hannah is ready to make her first hire and is seriously considering looking beyond U.S. borders — but she doesn't know what she doesn't know. In this episode, Preston is joined by Brian Samson, a three-time founder who has scaled recruiting agencies to $4 million ARR by building teams across Latin America and beyond. Together they walk Hannah through exactly how to approach international hiring for the first time: where to start, which regions tend to excel at what, how to think about time zones, and the blind spots that trip up most first-time international managers — including the costly "follow-the-sun" communication trap that can burn a full week on a single misunderstood task. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices
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Scared to Hire Overseas
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