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Brian Samson

Sep 23, 2026

6:51
What happened between December in December 2025 until September 2026?
6:58
Yeah, so maybe I'll talk about a couple initiatives we've done as a company.
7:04
And then I'd love to talk about the macro trends that we're seeing.
7:10
I love that conversation, yeah.
7:11
Even if people aren't a buyer of near-source services, we still want to know what we're seeing in different parts of the economy and politics, how things are moving the needle, where allocation's going, all that stuff.
7:26
Um, so as far as like our strategy, we've, um, when, when we started, and I think this is like a lot of service business owners.
7:37
You say yes to anything you can at the very, very beginning.

9 MINS LATER

16:22
yeah.
2:36
What are some things, as a little bonus here at the beginning of the episode, what are some things they should watch out for or be thinking through early on in their business to be planning and building recurring revenue?
2:50
Yeah, so I think there's a plus and a minus of that.
2:55
Especially from the agency standpoint.
2:57
So I'm not talking about, you know, SaaS, software as a service.
3:00
I'm talking about, you know, agency where, you know, it's really time and materials that you're billing.
3:07
And the benefit of not doing ARR, especially in a recruiting sense, is recruiting, you know, like how a lot of us know it.
3:20
It's kind of like real estate agents, you know.

12 MINS LATER

15:20
What do you think she should watch out for, Brian?
7:54
10
7:54
years ago, I was living in San Francisco, and funny enough, I had never really been an entrepreneur, but had this thesis that fintechs, which stands for financial technology, if you use Robinhood or Wealthfront or any of these little apps for finance.
8:24
That's what FinTech is.
8:26
And about 10, 11 years ago, they were all over San Francisco, all over New York.
8:34
Companies had lots of capital, good product ideas.
8:39
They wanted to build these FinTechs, and they could kind of care less about how it was done.
8:44
So my thesis was, well, what if I had a software company that could build the financial products for these companies so like the initial software and um i found an investor and raised about two million dollars which felt like an enormous amount of money and then you start to look at how expensive it is to be in san francisco so i realized um this this is not this probably buys me like 20 servings of avocado So where could I put my dev team? And I decided on Buenos Aires, Argentina.

7 MINS LATER

16:27
What advice would you give your younger self or also the youth who's watching and who's also craving this kind of like expansion experience? part of business?
22:35
So how do I go about that? How do I, how do I sort of get into this space other than, you know, posting something on Facebook?
22:44
Yeah.
22:45
Yeah.
22:46
So a couple of things.
22:47
Um, it's not, exceedingly different than if you were to hire in your own city so let's say you're a five million dollar company in dallas you know how might you hire somebody um if they lived in houston you know uh you're gonna do some remote recruiting um job post you know uh have your recruiters source candidates now because latin america it's a different continent you know we we feel maybe a little anxious like where do we start what do we do um now what i what i tend to recommend if you're say like a very small company let's say you know you're a one or two person shop there's no shame at all in the do-it-yourself hiring and there's platforms that have existed for a long time upwork fiber right now i'm going to talk about the drawbacks to those but um but the positives are these are mature there's thousands upon thousands of candidates to choose from you post a job they apply you go through your vetting process you realize what's important to you because if everything's important to you then nothing's important to you you go through the interview and You're probably going to make a mistake that happens, you know, but you learn and you get better.
24:14
And it's kind of a low consequence, you know, type of mistake.
24:19
Once you've scaled up a little bit, so let's say you're that $5 million company and you start to really like Latin America, you'll realize there's limitations with at least Upwork because they changed their model.

17 MINS LATER

41:52
So tell us the, the Brian Sampson entrepreneur story.
1:05
tell us a little bit about when you learned that lesson.
1:09
Yeah, you know, I've had kind of maybe a couple different pivots in my career, you know, was a W2 individual contributor, you know, in the Midwest, worked for a bunch of tech startups in San Francisco, been an entrepreneur now for 11 years.
1:32
But I think it all, you know, they each have meaning, they each have their own meaning and they built on each other.
1:39
But from a personal standpoint, I think what has given me the most meaning was something outside of work.
1:46
So my wife and I, in 2020, became licensed as foster parents here in Hawaii.
1:54
And it was a journey.
1:57
It was rough.

24 MINS LATER

25:41
Um, and it
16:22
like
16:22
hundreds and hundreds of thousands of dollars per engineer.
16:25
There are companies that can't get enough mid to senior level engineers.
16:30
And the this could change, you know, monthly, but it's people like see all the vibe coding and, And they think like, well, wait, is that the death of software development? Not exactly.
16:49
It's making it really easy for anybody to build like an MVP or like a mediocre web application.
16:59
But once you start to worry about scale, reliability, security, all that, you need the mid to senior level engineers that can tie it all together.
17:08
AI is notoriously bad at integrating the legacy code.

8 MINS LATER

25:10
um,
2:01
That's
2:02
right.
2:03
Yeah.
2:03
Yeah.
2:04
Yeah.
2:05
Absolutely.
2:06
So just so your audience knows, I didn't grow up in a family of entrepreneurs.
5:01
this a decade later, you know.
0:58
Did you see that? Was that like a goal that you had or how did that all come about?
1:03
Yeah, I mean, I think I love the ethos of your show because I did not grow up in an entrepreneur family.
1:12
I waited a long time to become an entrepreneur.
1:15
I was I've been one going on 11 years, but that meant like my mid 30s is when I finally, you know, had the.
1:26
courage whatever insanity to you know go out on my own um uh and you know i i kind of did it in a weird way where um my well i should say i i actually did like a kind of a first level entrepreneurship, you know, way back in 2012, where I think this is where most people start.
1:54
And if they've ever read like the Robert Kiyosaki books, you know, cashflow quadrant, you know, there's like the four quadrants of, you know, employee, self-employed, business owner, and then investor.
2:08
So I've kind of been like moving my way, you know, through the Kiyosaki quadrants.

21 MINS LATER

23:26
Like, did you have mentors or did you take part in coaching program? What did you do?
CaitlinHOST
3:45
So I hate to start off by asking you about maybe the not-so-success stories, but I find that they honestly help us all understand what it really takes to become an entrepreneur and what can happen that a lot of people don't tell us.
4:00
Yeah, yeah.
4:01
So, um, plenty of those, don't worry.
4:04
Um, so maybe, like, a couple I can get into.
4:10
Um, so I started my first, like, real entrepreneurship journey, um, what I call, like, easy mode and hard mode.
4:21
So I actually raised money, which is unusual for a very first business unless you're in, like, San Francisco and you're around all the, the tech startup stuff.
4:30
So I raised about $2 million, which sounds like a ton of money, and, and it was.

24 MINS LATER

CaitlinHOST
28:07
Because we're in the online space, like, to us, tech is so natural, but there are so many businesses that have been around for so many years that have no clue, like, what any of us [laughs] are talking about, you know? [laughs]
1:01
Kinda what broke down in the business that made you wanna rethink about how you built a team?
1:06
Yeah.
1:06
So I was...
1:07
Just so people who've never worked in this environment, I was in the VC-funded tech world.
1:12
You know, you know it, being in Austin.
1:14
San Francisco is the same.
1:16
Everywhere, you know, there were startups.
4:02
If someone's listening right now and they, they wanna start a home service business, let's just stay in that category, what are some, like, top things that they should be looking for from nearshore talent, like position-wise, that a home service company could take on?
3:16
estate
3:17
in Hawaii.
3:17
What's been your experience with real estate in Hawaii? Yeah.
3:21
Well, I think, you know, there's this element of a wise investor told me, you know, about front pockets and back pockets, you know, so you kind of make your money from your business.
3:32
And you put it, it goes into your front pocket.
3:35
But you want to diversify a little bit, put some money in your back pocket.
3:39
So the way that we diversified in Hawaii, we actually only had like really one intentional investment property.

16 MINS LATER

19:19
work from home, work from home environment.
6:40
So, uh, what macroeconomic or geopolitical trends currently influence nearshoring decisions in tech?
6:48
Yeah.
6:48
[chuckles] This has been a very wild time.
6:53
Um, it doesn't matter where you are on the aisle, if you're pro-Trump, pro-Trump, anti-Trump, Trump impacts geopolitics, and there's winners and losers in this administration.
7:06
Uh, China and India are two countries that, um, used to be mega exporters, you know, both physical goods and labor to the US.
7:19
Uh, now they're in the doghouse.
7:21
Um, so you're seeing a lot of physical good manufacturing moving to Mexico, other regions.
9:44
So how do you navigate country-specific nuances like talent pool quality, costs, culture when you're building teams across Latin America?
5:37
Probably,
5:38
yeah.
5:39
You look at India has been the IT offshoring center for forever.
5:44
I mean, they graduate more software engineers every year than some countries have people.
5:50
I mean, it's just insane.
5:53
And then the Philippines have really established themselves as the back office, call center, virtual assistants, researchers, medical billers, things like that.
6:05
And Asia has always come out on top when it comes to price.

13 MINS LATER

19:34
So I wanted for you to share about how you got into fostering and share a little bit about that.
11:20
So tell us a bit more about what you did before or after or during, what you actually do to other customers, companies,
11:36
for people to know.
11:38
Sure.
11:38
I appreciate that question.
11:41
So I didn't start off as a nearshore guy.
11:43
I grew up just outside Chicago and got into the recruiting world.
11:49
I was a recruiter, technical recruiter, then eventually moved to where all the action was in California.

29 MINS LATER

40:58
Sure.

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