Brian Samson on Entrepreneurship, Nearshoring & Building Global Teams

From Midwest Roots to Global Business: What Brian Sampson’s Journey Teaches About Entrepreneurship

Entrepreneurship rarely begins with having all the answers.

More often, it begins with curiosity, discomfort, risk-taking, and a willingness to step into unfamiliar environments. That’s exactly what stood out to me during my conversation with Brian Samson on the You're the Boss Podcast.

Brian is the founder of Plug, a nearshoring staffing company helping U.S. businesses connect with highly skilled talent across Latin America. But what makes his story so compelling isn’t just the business success — it’s the journey that got him there.

Brian grew up in the Midwest in a very traditional household. Entrepreneurship wasn’t something he was exposed to early on. His parents followed stable career paths, and naturally, he did too after graduating college.

Like many people, he initially pursued the “safe” route.

But everything changed when he moved to San Francisco.

Being surrounded by startups, innovation, and ambitious founders completely shifted his perspective on what was possible. Working within early-stage tech companies gave him a front-row seat to the realities of scaling businesses, especially the importance of hiring the right people.

One thing Brian emphasized throughout our conversation was how critical talent acquisition is to business growth.

And honestly, I couldn’t agree more.

So many businesses focus heavily on product development or sales strategies, but the reality is this:

your business can only grow as fast as your team can support it. Hiring the right people isn’t just an operational task — it’s a growth strategy.

What I also appreciated was Brian’s honesty about imposter syndrome.

Despite building a successful career, he admitted feeling intimidated when surrounded by graduates from institutions like Stanford and Harvard. Coming from Southern Illinois University, he questioned whether he belonged in Silicon Valley’s competitive startup world.

That feeling is something many entrepreneurs experience, especially when stepping into bigger rooms or unfamiliar industries.

But instead of allowing self-doubt to stop him, Brian used it as motivation.

Eventually, he made the leap into entrepreneurship himself. After pursuing an MBA through a joint program between UCLA and the National University of Singapore, he explored opportunities internationally and began pitching business ideas to investors.

His persistence paid off when he secured a $2 million investment to launch his company.

One of the most fascinating parts of Brian’s story was his strategic decision to build his business in Buenos Aires.

After traveling extensively, he recognized both the incredible talent pool available in Latin America and the advantages of nearshoring for U.S.-based businesses.

For companies today, especially in a remote-first world, nearshoring has become an increasingly attractive solution. Businesses gain access to highly skilled professionals, aligned time zones, and stronger communication while often reducing operational costs compared to traditional outsourcing.

But beyond business strategy, Brian’s story is really about adaptability.

It’s about recognizing opportunities outside traditional paths, being willing to take calculated risks, and understanding that growth often happens when you place yourself in environments that challenge you.

And perhaps most importantly, it’s a reminder that entrepreneurship isn’t reserved for people who have it all figured out from the start.

Sometimes, the people who build the most impactful businesses are simply the ones willing to keep moving forward despite uncertainty.

To hear the full conversation with Brian Samson and learn more about nearshoring, startup growth, and building global teams, listen to the full episode of the You're the Boss Podcast.

Key Takeaways

• Talent acquisition is one of the biggest drivers of business growth

• Nearshoring offers businesses access to skilled global talent with operational advantages

• Imposter syndrome is common among entrepreneurs at every level

• Strategic location choices can significantly impact business success

• Entrepreneurship often begins by stepping outside traditional career paths

👉 [Click here to listen to the full episode]

Take the free Personal Brand Power Scorecard and find out exactly where you stand in five minutes.

👉 Take the free scorecard now