Brian Samson

Brian Samson

[00:00:00] This is an undiscovered legacy production and proud member of Pod Nation Media Network.

Speaker: Once I became aware of it, like self-aware of. There's actually a benefit to doing this. So my scope has just exploded broadly over the last 10 years, starting different companies getting into boring businesses like locksmiths and cleaning companies, and doing angel investing and all sorts of stuff in real estate investing.

And just kind of like learning how to do all these things because I. I had this confidence now of I can figure stuff out and everyone starts somewhere. You just gotta start.

skoob: Simulation School believers, and we are here again with another amazing entrepreneur today. We're here with Brian. Hey Brian, how are you? 

Brian: I am thrilled to be here. 

skoob: All right. Thank you so much for taking the time outta your day to be on The Undiscovered Entrepreneur, get across the start [00:01:00] line.

Super appreciate your time. 

Brian: Absolutely. 

skoob: All right. So, uh, right here off the bat, I'm gonna have kind of a semi-serious question to ask. Are you ready? You ready there, Brian? 

Brian: Let's do it. 

skoob: Okay, here we go. Are you a SC believer? 

Brian: I think I am. 

skoob: Alright. We have another SC believer. Thanks Brian. Really appreciate that.

Alright. Alright. Like, so what I'd like to do right here up front is get an idea of, uh, who you are, what your entrepreneur adventure is, and how you got across a start line in your entrepreneur adventure. 

Brian: Yeah, sure. I love this question and I love the show premise because I a hundred percent relate to all the listeners here.

I grew up Midwest. My dad worked for the same company for 30 years. Mom stayed home and. It wasn't like in an entrepreneurship family, like I didn't have any uncles or grandparents or anybody, you know, people just kind of seemed to [00:02:00] work at a company and that was that. And and it wasn't until, uh, I was 30.

I moved to San Francisco and, um, so I didn't have any entrepreneurship contacts, you know, I didn't know any, like plumbers or electricians or the guy that owned the store, you know, the deli. And then I, I got, this exposure right away to the Silicon Valley entrepreneur, which is kind of a different breed.

You know, you're, you're looking at you know, they. Go to Stanford and Berkeley and they've got this big tech idea and they're not thinking about, you know, how do I make a couple hundred grand and provide for my family? They're thinking, how do I raise enough capital? To build this massive business that has to have potential to be a billion dollar business.

So my investors are happy and everybody's happy, so it's just like a totally different kind of thinking. But I spent five [00:03:00] years, in that environment. And, you know, you talked about in the pre-show imposter syndrome. 

skoob: Mm. 

Brian: And had that in spades because, you know, I went to a school in the Midwest called Southern Illinois University and nobody in California had ever heard of that.

I did I came up in like the talent world by the way, and I did what a lot of people as kind of a rite of passage. You do a year long contract at Google as a contract recruiter. So, you know, I did like the whole, you take the Google bus, you know, from San Francisco down to Mountain View. It's about an hour.

And wifi and the bus, and there's everything you, you see in YouTube, you know, there's ball pits on campus and these little yellow Google bikes you ride around and 20 plus different cafes and a gym and everything. But where I'm going with that is. [00:04:00] They, um, they were very open about how they scored different universities.

So, uh, if you went to Stanford or Berkeley or Caltech, you know, that's like a tier one USC and maybe like Cal Poly Pomona or University of Illinois, Indiana. These are kind of tier two and there's tier three, and right at the bottom was. My university. So I immediately had this kind of imposter syndrome chip on my shoulder.

Do I even belong to be in the room here? Then I ended up working as a head of talent, uh, which is like a recruiting plus, 'cause recruiting's really the, the biggest spender of funds, I should say. You know, when companies raise capital, it's okay, now we gotta go hire a bunch of people. So, um, I was with all these early stage founders and exposure to, you know, as they're working out [00:05:00] their big billion dollar idea and some really, really smart people.

So, uh, five years of just trying to like, get confidence and feel like I could be in the room. And I never had any real entrepreneurship experience. And then, I started to gain a little bit more confidence. I, I could see like, hey, they're smart, but I think I'm smart too, it makes me think of the, like Stewart Smalley character, you know, from Saturday Night Live a long time ago. You know, of I'm good enough, I'm smart enough and gosh darn people like me. You know? So after five years of that, you start to kind of build a little. Little more self-esteem and think you can hang.

And and then I had a whole thesis, um, that I can get into that kinda launched that first business out of the gate. But origin, you know, I was, uh, low confidence. Didn't think I could, I could hang with that crowd. 

skoob: I think we all come across at one [00:06:00] point or another whether we're just growing up or just getting into a kind of like a new area that we're not really a hundred percent sure on.

And, and I, I think you coming from a, a non entrepreneur family give you a different kind of perspective of what Entrepr. Entrepreneurship means. 'cause a lot of times if you have family members that are in entrepreneur and they've been in it for quite some time, they're kinda like, okay, this is the way I did it, so this is the way you need to do it too.

But you went in there basically raw, like, I've never been in entrepreneurship before. Let's see what I could learn with what's around me. And I'm, I'm a, I'm originally from the San Francisco Bay area, so like I kind of get where you're coming from that area. 

Brian: Yeah, yeah. 

skoob: But it's interesting to me that.

Even though you were feeling imposter syndrome going through what you were going through day after day after day for five years, you still pushed through that and still came out ahead. Um, what, what was the breaking point for that? I mean, when did you finally realize, Hey, you know what, I could do this.

What, what was that like for you? 

Brian: Yeah. [00:07:00] Yeah. I realized, um, that I had two things going for me. At the very beginning, it was work ethic. Like I wasn't afraid to work hard and, you know, realized, and it sounds so cliche, but you know, you can, you can control that, right? You, you can't control a lot of other cars you're playing.

But it's funny, you know, when I grew up I mean I was about as average as you could get. I was probably the middle of my class rank. I was an average athlete, you know, average intelligence, average, you know, looks everything. Um, and then, um, and then, you know, as I but I, but I still kind of had, I think like a type a mindset, but really all that meant is I was kind of uptight and stressed all the time and, you know, put a lot of pressure on myself.

And even when I'd play like Little League Baseball, I was always put all this pressure on myself to succeed. And I think, 'cause I got to. San Francisco, I learned a little more about how to think of it maybe from a tech perspective. And and [00:08:00] you could you could work 20 hour days. And there were some startups I was at where that was kind of the norm.

And by the way, no one's really working 20 hours. They're taking breaks to go play Xbox and taking breaks to like have dinner. And they counted like, oh, I was at the office for 20 hours. You, you probably worked 11 hours. Okay. Still, still a lot, but not 20. But, um, but anyway, I think I started to shift more into this like type B mindset, which played into the other part of how can I do this with the least amount of hours.

And I started to uh, and I think a book that I read. The, the title's misleading, but it's the Tim Ferris book, the Four Hour Work Week. You know, I read that when I got to San Francisco in 2011 and and it just kind of got me thinking about leverage and how could I do more with less. [00:09:00] And if I, if I worked fewer hours, could I still be as productive?

And I kind of took this as a challenge. And, um, funny enough, I don't think I've, I've, I've told some people this, so it's not a, it's not a true shocker, but, um, but I actually got fired from Google because of this. You know, I was like. Working essentially two hours a day. You know, like I take the bus and go screw around at the cafe and screw around at the, at the gym and take the early bus home.

And and my numbers were like right there with everybody. In some cases beating, but I was barely there, you know, didn't have the FaceTime. But. I wasn't discouraged. I wanted to see if I could do more of this, you know, in these tech startup environments. So I would always be the last one to get to the office, usually the first one to leave.

But found like little patterns and angles that I could break and ended up uh, one of the places I was at again, I was leading the talent function. So a company [00:10:00] that actually went through an IPO, an initial public offering. We, uh, were rated the, the world's top recruiting department for companies under a thousand people.

And you know, I was the architect of that. And I wasn't killing myself. I was just trying to think creative and, you know, and find patterns that maybe people weren't, weren't looking at it. So, um, long story short. I think the, the frameworks that I kinda learned were you could choose to work yourself to death.

And I think that's how most people might give advice. You know, especially when you're young, you don't have a ton to offer besides hours. Um, but I will say there's a lot to be said about, we all have a totally different view of how we see the world and, um. You have a very unique view. Everyone, everyone watching, listening to this has a very unique view.

And, um, you might see a pattern that other people don't, [00:11:00] which allows you to do things much different, maybe way more efficient and effective. 

skoob: And then, then you you know, it's funny to me that Google would fire for something like that. I would've, I would've given you a promotion personally, just because, I mean, if you're, you're able to work that efficiently.

Why wouldn't I want you, not only you to work that efficiently, but everybody else to work that efficiently too. 

Brian: Where were you 20 years ago? I don't 

skoob: know. Yeah, right. But yeah. And, and it's funny to me, especially in, in a corporate environment, and this is one of the reasons why people tend to shy away or get away from a corporate divide, if you don't fit the mold, they don't want you there.

Brian: Yeah. Yeah, 

skoob: and it's, it's very unfortunate that we've gotten to that point. But the nice thing is now that you know you can do these things, what can you do for yourself that fits all these ducks in a row that you can make into a business? So. At that point, after going away from Google [00:12:00] or Google, going away from you, however you want to put it, what, what did you build from there?

Because it sounds like this turned into a, to a positive thing more than a negative thing. 

Brian: Yeah. Yeah. So I ended up getting in into some early to mid stage tech startups, you know, did, did four or five years of that. And then I had a thesis I should back up for a second because I, I didn't. Fully intend to go the entrepreneurship route.

But I had. There's a lot of luck in this story too. So, funny enough, I really wanted to be an expat in Asia. I just had this like vision in my head. My wife's dad was a expat in Asia. When she grew up. So she grew up, um, you know, in Japan and Korea. I just thought that was so cool for me though, it was, it would be like Shanghai or Singapore.

I just really wanted, wanted to have that experience and, um, I. I had this thesis about I, you know, from being from San Francisco, there's [00:13:00] fintechs everywhere and San Francisco, New York, there's all sorts of the next generation of lending companies and wealth management, all that, all these, you know, tech startups.

And I saw that they didn't really care about the tech stack or how it was built, but they had lots of capital and a good product vision. So what if I could do this? So as my expat thing didn't really happen as much as I wanted it to, I did reach out to somebody in China who was very successful, had a lot of capital, and I told him about my idea and he said, you know what?

I like it. Let's go a little deeper. So I spent about a month like. Building a deep pitch deck and forecasted models and all sorts of stuff I kind of learned on the fly. Which by the way, uh, say yes and figure it out is something that, that I'm not afraid to do. I don't get stressed by stuff. I don't know.

I just figure it out. 'cause you know, that's, that's [00:14:00] life. And you also have to remember that you're learning it for yourself, right? This is all compounding for you. Um. After about a month of preparing, um, I convinced him and it was a t tranched investment. So little bits of investment over time, but the cumulative was $2 million.

And, um, I never raised capital. And this all of a sudden, you know, I've got this $2 million check. That led me to getting this business off the ground, which was technically a services company 'cause we were building platforms for tech product companies. And, um, I did, I did get my expat experience, but not in Asia.

Ended up moving to, uh, Buenos Air Argentina, where, um, kind of did entrepreneurship on hard mode, you know, where different language, really difficult place to do business. And figured out how to get an office, set up payroll, set up [00:15:00] taxes, accounting pay my team, and we grew that to about 80, 80 software engineers.

So kind of learned it all on the fly and made a billion mistakes. And thankfully I had someone funding it so I could make some mistakes. But the other companies I've founded since then have all been my own money. And there's a little bit of a different lens you, you have when it's someone else's money and it's your own money I can get into, but that's kind of how it all, all got going was um, building software for FinTech companies.

skoob: Fantastic. And I think the, my favorite part of that story is, number one, you were accidentally became an entrepreneur. Those are the fun. Those are the best ones, I gotta tell you. 'cause it's like, oh, by the way, I'm an I, what? I'm an entrepreneur now. How does that work out? But I, the, the experience that you had and then you went away, but because of meeting somebody.

Yeah, even though the rest of the experience [00:16:00] probably wasn't that great, you met that one person during that experience that helped you along with, you know, your, your new adventure. And if you didn't go through that experience or you didn't have that negative or go into the place you didn't really want to go to.

You wouldn't have had that opportunity. Sometimes at the, at the point that we're at now, may not seem so great, but the reason we're here is because something's supposed to happen in our lives that's gonna lead us to the next thing we need to be at. 

Brian: Mm-hmm. So 

skoob: don't, don't be really upset that sometimes that you're not really exactly where you want to be.

You're supposed to be there for a reason. You're there too. Yeah. Meet somebody or you're there to make a connection somewhere that's gonna help you along. I've had to tell a lot of new entrepreneurs that too. I don't really like what I'm doing. Are you doing it? Yeah. You're supposed to be doing something that's gonna lead you into, which I actually do love and yeah.

Saying Yes. You know, those are the most exciting entrepreneurs. You say yes, and then learn [00:17:00] the thing, you know. My mentor, pat Flynn, when he was an architect they were looking for somebody to do a computer wire framing. I'm not a technical guy, but like a computer wire framing of a room, and he was like, I'll do it.

He had no idea what he was doing. He actually had to learn how to fly too, and he, he, it was accepted. So sometimes that's, that's sometimes that's fun. Sometimes it's like, yes, okay, I'll do it. What am I doing? You know, ask, ask questions later. So that's awesome that you've experienced that. I do have a question though, and it does kind of go into imposter syndrome and that kind of thing too.

Brian: Yeah. 

skoob: When you were experiencing imposter syndrome while you were in Google and working for Google, did you, let's see, how, how would you get over that imposter syndrome or that particular point? Because personally I feel that. If you're feeling imposter syndrome, you're actually going the right way. You know that you're working hard towards something.

So I'm just kinda curious what your feeling was on that. 

Brian: So that was a really formative time for [00:18:00] me because I think and I'll give the flip side of that in between, uh, the Midwest and San Francisco, I lived two and a half years in Orange County. Beautiful place to live, um, right by the beach. And, you know, I rushed home through the traffic of SoCal and grab my boogie board, you know, and ride the waves.

But um. I realized that I I don't think I was hanging out with like, the most elite people in, in southern California, by the way. Um, but I felt like I was, um, me meaning that this comment if I was hanging out with. Smart people. I probably wouldn't have said this, but I wasn't. So, um, uh, so I felt like I wasn't growing, you know, after two, two and a half years, my career was just kind of stuck.

And then when I went, when I came to San Francisco, it was just the opposite, you know? Um, I didn't have as much play time, but I was pushed and pushed hard mentally all the time. And in the moment you feel. [00:19:00] You're the dumbest person in the room. And that was the case of Google. That was the case of all these tech startups with all these Stanford people.

And then, um, I was also doing grad school. I didn't mention that uh, at UCLA and I didn't even wanna apply to UCLA. I thought there's no way they'd accept me. And by the way, like ucla, LA is not Stanford, by any, any stretch. But you know, it's, uh. Top 12, top 15, whatever year they're doing the survey.

And I thought that was like way too much of a stretch. And thankfully my wife, you know, really pushed me to do it. So I got in and there was. 38 people in that cohort. I thought I was ranked 38th in terms of intelligence and what I had to offer. And I mean, I was like afraid to even speak up. And these MBA classes are all about, you know, being aggressive, share your opinion, disagree.

And I mostly, I was like the quiet guy and that whole program just observing and like, what do I have to offer here? [00:20:00] But I think I realized, during all those, those three experiences, which all happened to be in this five year period in the Bay area of, I can't think of another five year period where I grew this much because I was I wouldn't say okay, but.

I was mostly okay being the dumb guy, all the time. And then but I think it, you know, pushed me to look for patterns, pushed me to try to find different ways to, to look at things. Um. Then I think once I became aware of it, like self-aware of there's actually a benefit to doing this. So, my scope has just exploded broadly over the last 10 years.

You know, starting different companies, getting into. Boring businesses like locksmiths and cleaning companies and um, doing angel investing and all sorts of stuff and real estate investing and just kind of like learning how to do all these things because I [00:21:00] had this confidence now of I can figure stuff out and everyone starts somewhere.

You just gotta start. 

skoob: And that's what I call getting across the start line. That's, yeah. It's so important to get started. 'cause if you don't get started, you're not gonna go anywhere. Yeah, you're gonna be stuck right where you're at for however long it is that you're gonna be at. I personally, now, personally, I don't want to be the smartest person in the room.

Brian: Yeah. Yeah. 

skoob: I, I would much rather be the dumbest person in the room. Learn everything I can from the, the other 34 people that, that are in the room. Mm-hmm. But don't be afraid to walk up and actually talk to 'em. Ask questions, Hey, what about this? And you said this. Can you elaborate a little bit more on that?

Learn as much as you can from the people that are around you. A lot of people have the misconception that these people are competition for you. Mm-hmm. And I don't know in this case, personally, I think these people are in competition. These people are there to help you, but you have to be able to take that first step [00:22:00] with your hand out saying, Hey, my name is this.

I'm looking for this. Take that first initial step. They're not gonna come to you. They don't even know who you are yet. Why would they want to come to you? You need to take the initiative to go up to these people and ask them the questions that you need. And because of that and everything that you've learned from those people, the imposter syndrome starts to get less and less and less.

'cause now you know, these are the steps that you need to take. So that's fantastic. That's a great story. Brian. Thank you so much. Uh. 

Brian: Appreciate 

skoob: that. Um, if you were to come across a brand new entrepreneur that's just getting started, that's literally just getting started. They say, Hey, I'm starting this business.

What advice would you give 'em? What steps would you have them take? 

Brian: This is something I I say a lot, which is learning from my own, my own mistake. So I, I technically did like a. Pseudo entrepreneurship, but I was really like a contract recruiter, for a, for a year, I think. Between Google and these tech startups.

I'm like, I, I'll, I'll, I'll go out on my own and, you [00:23:00] know, find my own projects. But, um, I legitimately, had a website I incorporated and I was gonna try to scale this and, bring other people in. But the biggest mistake that I made by far is I, was so distracted by things that make you, make you feel busy.

Like the grammar on my website, you know, and I'm up at like two o'clock in the morning, you know, looking for typos on this or, um, spending a week. Should I be an S corp or just a regular LLC or should I do a C Corp in Delaware? Like, no. Get a customer. That's all you should be thinking about when you're starting a business is how do I get a customer and then how do I get a second customer and then how do I deliver for them?

It's so easy to get to fall in this trap because there's information overload out there, there's a billion videos on entrepreneurship and [00:24:00] articles and blogs and AI ideas and all sorts of stuff. Don't get distracted. Get a customer service, the customer, and just try to keep learning on your service or product.

skoob: That's right. That's right. That's awesome. Yeah. Fir, first of all, don't get distracted by perfectionism. It's not gonna be perfect. I mean, you could get down into the nitty gritty details of trying to make sure all your commas and all your i's in lowercase j's are dotted or whatever, but I mean, you're, you're still not doing much of anything except for correcting something over and over and over again.

So be, be careful with that. But if you're first getting started, first of all, you need to find your zone of genius and know what your zone of genius is so you can hone in on that one particular thing. Then when you get that, find one person. With one problem that you have one solution for. Get that first customer and then after you get that first customer, get feedback from that cus first customer [00:25:00] and just use that information and get onto your next customer and so on and so on.

Pretty soon you get a couple, three, four people underneath your belt and it just goes from there. So that's amazing. 

Brian: Absolutely. 

skoob: Alright, so Ryan, I have a, a tradition that I have with all my guests in the next six months. Where do you see yourself in your, your business? I mean, do you have a six month goal for yourself?

Brian: Yeah. Um, well I've got five different companies now, uh, that I operate, and, um, each one has, has a different goal. Um, but the biggest is, uh, a Latin America staffing company with about a hundred people today. And you know, our goal is to, uh. Scale to the mid-market. So in six months I'd like to have several customers in that, the medium sized world.

And then, you know, maybe in a couple years later, we'll we'll be at that enterprise game. [00:26:00]

skoob: Alright. Awesome. So what I'd like to do with you, if it's okay, Brian, is I'd actually like to follow up with you in six months. 

Brian: Yeah. 

skoob: See if you've actually reached those goals. I'd also like to follow up with you and see what kind of new experiences you've had.

Sure. Between the time, between whatever now is and whenever later is, and we talk to you. Is that okay? 

Brian: Sounds great. 

skoob: Alright. 'cause now you're not just accountable to me, you're accountable to all my scuba believers out there. So don't, don't mess this one up. No, I'm just kidding. 

Brian: I like it. 

skoob: Alright. 

Brian: Sounds great.

skoob: Alright, Brian, this is your time to shine. This is the time where I want you to advertise yourself, how do we get ahold of you and all that good stuff. Okay. Ready, set. Go. 

Brian: Yeah. Uh, plug Technologies, PLUG, do Tech is our website and you can go right to our contact page and, uh, all those notes go right to me.

skoob: Alright. Awesome. Brian, thank you so much for being on The Undiscovered Entrepreneur. This was awesome. I loved all your stories about Google and where you've been, and I'm really looking forward to see where you're going with this. Okay. [00:27:00]

Brian: Thank you so much. 

skoob: Alright. Alright, school believers, make sure you stay tuned for the wrap up.

Okay everybody. Thank you. Bye-Bye.

Speaker 3: Alright, school believers. What a fantastic conversation we had with Brian today. , I, we had a lot in common. Both of us came from California. I, I love his stories, but I did have two major takeaways I wanted to make sure that you caught in our conversation.

Being the dumbest person in the room is your greatest competitive advantage. Stop avoiding rooms that intimidate you and start seeking them out because this discomfort you feel is not a warning sign. It's a growth signal. When we go into a room and everybody in that room is smarter than we are, then more than likely we're gonna learn something from each and every one of those people that are in that room in some way, shape, or form.

That's what helps us grow. That's what gets us across the start line, is the people around [00:28:00] us that will teach us, that are willing to sit down with us and show us what we need to do, and those are the smart people we need to learn from. So make sure when you go into a room, whether you're in a classroom to learn something, whether you're networking. Make sure you're absorbing as much knowledge as you can from the people that are smarter than you, and stop perfecting your website at 2:00 AM to get a customer. Every hour you spend on commas, business structures, and logos is an hour stolen from your only action that actually builds a business.

And that's talking with people and that's getting out there. Learning and being with the people that you need to be around to make your business and your dreams come true. There is a place for the commas and making sure everything looks okay and make sure your logos are good, but spending all that time to be [00:29:00] perfect in those things is just a waste of time.

Instead, talk to somebody. Get on a Zoom call. Contact somebody, network. Get into your local areas. There's so many other things you could be doing to make your business grow than, making sure there's a period at the end of every sentence.

And with that, I'm gonna say thank you SC Believers. Make sure you. Subscribe if you can, if you feel like you want to, I know I don't say this too often, but if you could please gimme a five star rating or whatever podcast platform that you're listening to right now or on YouTube, that would be amazing.

It would mean the world to me to be able to get that, and

we have some more great stuff in the work, so make sure you follow and subscribe. Okay, everybody. Thank you. Bye-bye.