August 23, 2023

How to Become a Content Machine and Building a Business from Scratch with Colton Sakamoto (DF#111)

How to Become a Content Machine and Building a Business from Scratch with Colton Sakamoto

Why Content Will Give You Tons Of Opportunities

Join us for an insightful episode as we unravel the journey of Colton Sakamoto, co-founder and former CEO of Infection Points, and currently the Chief Party Officer at Office Party. In this jam-packed conversation, Colton takes us through his remarkable path to success, from humble beginnings to building thriving ventures.

Colton Sakamoto is the Chief Party Officer at The Office Party. Prior to The Office Party, he co-founded Inflection Points, an employment-focused company that helped 1,500+ job seekers start new careers.

In this episode, you'll discover:

- How Colton started his entrepreneurial adventure from the comfort of his childhood bedroom, overcoming challenges and eventually selling his company, Inflection Points.
- Valuable insights into the world of content creation and its synergies with entrepreneurship, as Colton shares his experiences transitioning from a content creator to co-founding Office Party.
- The impact of Colton's decision to pursue an MBA on his career trajectory, with candid reflections if it really added value to his professional growth and decision-making.
- Strategies and secrets behind building a loyal following and nurturing a thriving community for aspiring entrepreneurs and content creators.
- A glimpse into Colton's visionary ideas for the future of Office Party, including innovative approaches to monetization and platform expansion.

We dive deep into the nuances of entrepreneurship, content creation, and starting a business from scratch.

Whether you're an experienced business owner or contemplating starting a side hustle, there's something valuable for everyone in this episode.

Don't miss the chance to learn from Colton Sakamoto’s journey and insights to elevate your own path to success.

Enjoy the episode!

Want to make a huge career change?

Sick of applying to jobs and hearing nothing back?

If that's you, then check out our Career Change Crash Course. We'll teach you how to identify the skills you need to get the work you want, how to craft a story around your past experience, and how to sell your skills to your future employer!

Like, subscribe, write us a review, and if you have a question or want some advice email us at [email protected]

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Want to learn how to go from trades to becoming a 6-figure engineer? Check out the previous episode!

Links and Notes from the Episode

Episode Transcript
Please enjoy this transcript or our episode!

Please note the transcript may have a few errors. We're human. It can be hard to catch all the errors from a full length conversation. Enjoy!

Colton Sakamoto [00:00:00]:

Putting yourself out there is super, super important. There's basically infinite potential with it. It's a massively asymmetric opportunity. The downside of posting more is, hey. I'm waste some time and nothing comes a bit. The upside is, you know, job opportunities. It's entrepreneurship. It's investment opportunities. It's all sorts of things. Those things will never come to you unless you start to put yourself out there more.

Ryan Maruyama [00:00:25]:

Hello, folks, and welcome back to degree free, where we teach you how to get hired without a college degree. I am your host, Ryan Maruyama, Before we get into today's episode, I'd love to tell you about the degree free network. It is a free community for people just like yourselves, all trying to get hired get ahead and reach your career goals. It is a free community, and you can sign up at degreefree.co4 slash network. Once you're in there, you can take a couple of free courses like the 7 day get higher challenge. Not as gonna teach you in 7 days how to get hired without a college degree and also the 5 degree free pathways course. If you have no idea what you wanna do, but you know that you're ready for a change then the 5 degree free pathways course and the 7 day get higher challenge course are gonna help you get there and make that career change. And if you haven't already, you can sign up for free weekly newsletter, you can go to degree free dotcoforward/newsletter. The newsletter comes out every week and it has different degree free jobs. degree free tips on how you can get hired without a college degree. And now today's guest is Colton Sacamoto Colton Sacamoto is the chief party officer over at office party. You can sign up for their twice weekly newsletters by going to join Colton is also the co founder and former CEO of inflection points. We go over a lot of things in this episode and it is jam packed with value. We go over the value that he got out of his MBA. his decision to get his MBA, what it was like starting inflection points from his childhood bedroom, and what it's like becoming a content creator and starting office party now. I will say for those long time listeners, this is gonna be a little bit of a different interview. We get into the weeds about a lot of things, particularly entrepreneurship, getting followers, content creation, There is something in this episode for everyone. If you have ever thought about starting a side hustle or starting a business, This episode goes into detail of how he started inflection points. We also go over how he started office party and his ideas for monetization going into the future. We talk about the decision making behind him going back to school and getting his MBA. Like I said, there is something in this episode for everybody. You can say hi to Colton on LinkedIn. He is Colton Sacamoto. that is sakam0t0. And as usual, I will have links to everything that we talk about atdegreefree.coforward/ podcast. And without any further ado, please enjoy my conversation with Colton Sacamoto. Hello, folks, and welcome back to the degree free podcast. I am super excited today to have on our guests, Colton Sacamoto,

Colton Sakamoto [00:03:17]:

Colton, thank you so much for taking the time. Yeah, man. Thanks for having me. Really happy to be here.

Ryan Maruyama [00:03:22]:

Colton, I am excited to have you on You are the chief party officer over at office party. I love it. You were the former CEO of inflection points. You're founder there. We could talk about that in a second. I'm really excited to have you on because I think that our conversation today can go a lot of different directions, entrepreneurship, content creation, different job seeker tactics. Really, really excited, but I'd love to start at what you are currently doing over at Office Party?

Colton Sakamoto [00:03:57]:

Yeah. So the Office Party is a free newsletter. And sort of the problem that we're trying to tackle with the office party is that career news, HR news is is really boring, and it's bland. And you don't really Get good news unless you're scrolling through your feed, whether that's Twitter or TikTok or LinkedIn. And the problem with that is the nation is often unreliable. You're sort of getting it through the grapevine. It's hard to verify. And so what we're aiming to do is really target people working in HR crewman and even job seeking and just provide them with the latest information in the industry, keep them up to date with layoffs, with hiring trends, with who's raising money, all that sort of stuff. So what we're trying to do is basically compile all of the HR news and present it in a fun, entertaining way. It's a newsletter. Does it go out daily, weekly? What can people expect if they sign up? Twice a week. So Tuesday Thursday morning, a fresh office party hits your inbox. The goal is to make you laugh a couple times, sort of brighten up your day. I think we're bombarded with the negative news a lot of time. And so we try to put a positive spin on everything try and make you laugh, and we try and sort of brighten your week up, you know, with this newsletter hitting your inbox every Tuesday or Thursday morning. That's awesome. And, yeah, it's definitely

Ryan Maruyama [00:05:11]:

good change of pace. It's in a welcome change of pace instead of all the, doom scrolling on Twitter even on LinkedIn too. Where can people sign up? I won't bury the lead. Where can people go? Yeah. Join office party dotcom. Tons of memes, tons of information, tons of resources, check it out. Perfect. Perfect. Now, I would love to kind of go back to the beginning. So this is the degree free podcast. It is our goal to help people succeed in their career, in their life, really whatever success means to you all without having to go back to college or go to college in the first place, we think that there are avenues out there that you can take to get to different places. That being said, you have a degree I believe you have an MBA as well. I would love to start with the MBA. The reason why I'd like to start at the MBA is because I have talked about this on this podcast before. The MBA seems to be the most utilitarian masters degree that there is. And what I mean by that is that it seems to be one of the most easily marketable to people because they'll look at a MBA and they'll say, well, it says it in the title. It says masters of business administration. And so if I get this MBA, I am going to be a master of business. there are a lot of people that I know personally that have gotten MBAs from different schools from all over, really. I mean, from actually now that I think about it, I know people that have gotten MBAs from University of Phoenix that have gone all the way to the 1 word schools. I would love to know what your own experience with the value of MBA. And I wanna clear to the audience that we have not talked about this before, and this question might be out of left field. So you might say that it's super valuable, but I would love to know what your experience

Colton Sakamoto [00:07:18]:

with the MBA program that you went through is. Yeah. So first off, I feel like a bit of a hypocrite being on the degree 3 podcast because I have 3 degrees, but I wholeheartedly believe in your guys' mission that you guys are are preaching and conveying. You know, long and short, I believe that my MBA truthfully doesn't have a ton of value. I mean, that's why I resonate so much with sort of the message that you guys are spreading. I think it makes sense to sort of backtrack and and talk about why I got MBA first, and then we can talk about sort of, you know, what that led to and how I valued the MBA. So I was a college baseball player. It was always my dream to play in the MLB. Obviously, I I feel, you know, pretty considerably short of that, but baseball led me to the University of Oregon for my undergrad degree. Truthfully, I wasn't ready to compete at the division at one level, but I love the school. And so what I ended up doing was dropping back to a junior college, which is right up the street, I do enroll at both Lane Community College and the University of Oregon, which allowed me to keep playing baseball, but also stay enrolled at the university that I really enjoyed going to. I graduated with my bachelor's and associates degree in 3 years, and then I had 2 more years of baseball eligibility left. And so I was sort of left at this crossroads in my baseball career where it's like, okay. I could hang it up early, you know, which I wasn't ready to do. or I can try and go get my MBA somewhere and play for a couple more years. I opted for the ladder, and I didn't really have a plan, you know, with my MBA. I did knew that I wanted to keep playing baseball. And if I can use baseball to pay for my NBA, then maybe someone will think it looks good on a resume, and it'll help me get a job. So I went at the Gardner Webb University in North Carolina. It's a really small division 1 school that most people haven't heard of. It's like a one stoplight town. total culture shock from from what I was used to, but it was a really good experience. We gotta play, you know, Georgia Tech and Clumpson at Wake Forest and a lot of big name schools, and I got to do my MBA while competing on the baseball team. And so that was a huge blessing, but after I graduated, I was sort of expecting to just walk into a great high paying job immediately. And what I found was people didn't really care about the credentials that much. You know, I graduated during the pandemic, and so the job market was a bit tough. but, you know, I really don't feel like my MBA, you know, brought me a ton of value. I think it brings people value at maybe when they're going to the harvards and the yields and their networking, you know, maybe they already have a high paying career that their company is sort of paying for their education. you know, but truth be told with my MBA, I don't feel like I really learned a ton and I don't feel like there's a ton of benefit from it other than, hey. I gotta keep playing baseball. What position did you play? outfield. outfield. center field, right field? I liked some of the best, but I wasn't quite fast enough to to play at the division 1 level. So I would play I put left field, and I was basically just concerned with when I was up to bat next, not so much the defense. I was just about to say you must have been a pretty good hitter. A little bit. Yeah. I I enjoyed hitting quite a bit more than the defense truthfully. Yeah. Baseball is a

Ryan Maruyama [00:10:15]:

very secret passion of mine. I'm not very loud about it, but, I love it. Yeah. I love baseball. I'm a huge San Francisco Giants fan. Yeah. They're actually turning out to be okay this year too, which -- Yeah. Good team. Yeah. Which is I did not think that was gonna happen. But, so you went from college straight to your MBA program. Are the days of requiring years of people to go to work with prior to an MBA program, are those done? Because When I was thinking about getting my MBA, this is over a decade ago or about a decade ago, I was looking at it, but then all of these programs that I were looking at, they were like, oh, you need to go to work for, like, 2 years at some prestigious job that was like, I'm never gonna get hired. At least back in the day, like, consulting or something like that. Exactly. Exactly. Are those days

Colton Sakamoto [00:11:11]:

gone? So I saw that a bit with Gartner Webb, it wasn't so much an issue. But when I was looking at some other programs, you know, they want people who are already in the business world and prior to coming in to to get the MBA. When

Ryan Maruyama [00:11:25]:

you graduated with your MBA. How did you end up with inflection points? Like, did you go and get a job afterwards? Did you just start inflection points in college?

Colton Sakamoto [00:11:35]:

What did that look like? Great question. So COVID hit during my senior year. It was my 2nd year of B MBA program when I basically got my truck. I was in North Carolina and drove across the country, and I really had no clue what I wanted to do. You know, when I was in the MBA program, people would always ask hey. You're getting this MBA. You know, what are you gonna do? And my famous answer was just, I don't know, to a lot of people that wasn't that wasn't a great answer. and in hindsight, it it probably wasn't a great answer either. But I really didn't know when COVID hit and kind of everyone's world flipped upside down, and I had to really think about what I wanted to do next. And so I moved home. I finished out my MBA online, and I just hit the job boards. I hit LinkedIn and and some of these other ones. I was sort of mass applying to everything that looked semi interesting, and I wasn't having much luck at all. And so I I got pretty frustrated. I was like, hey. I'm a division athlete. I got great grades, you know, and I'm struggling to get a job. I was told, basically, go to school, get good grades, you know, maybe do some extra curriculars, and, you know, everyone will offer you a job type thing. And it turns out that's that's not really how it works. There's a lot of other strategies which we can get into later. But, really, I had no clue what I wanted to do. And so I spent that summer kind of finishing out my MBA, you know, doing some fun stuff with friends and all that. but didn't really have too many leads. And I ended up working in a in a sales role right out of college, which is great. I got some good experience cold calling and stuff that I wasn't quite so comfortable with. But starting to kinda tinker on my own, and that sort of led to inflection points, which I can get too. We started that out of my childhood bedroom, me and my cofounder, and that grew rather quickly. And so I ended up actually stepping down from from my first job out of college to to pursue that full time. Yeah. I would love to talk about 1. What were you selling? Mortgage.

Ryan Maruyama [00:13:22]:

Oh, okay.

Colton Sakamoto [00:13:24]:

Awesome. did you like it? So I it was a great time to sort of enter the industry because I gotta learn really how mortgage is working. I think that's sort of an import important life skill. I also feel like I develop cold emailing and getting comfortable with some of those things that I wasn't so comfortable with. Additionally, it was a great time in the market too because interest rates were at historic lows. And so everyone was, you know, buying new houses and refinancing and and migrating because of COVID. And so, you know, gotta kinda jump right in and sort of learn these things that I I don't think I would have learned, you know, otherwise in a different job. Yeah. Awesome. And I do wanna point it out for the audience that to sell mortgages to work in the mortgage industry. You definitely don't need a masters, you know, for those people that wanna do that. Definitely not. You don't even need a college degree to to do it. In fact, a lot of people that I know in that industry And I'm trying to get a couple of them on the the show. A lot of them didn't even finish high school, like other GAD, you know, and that they just they can sell. Yeah. It was a great industry for me to to enter for that reason because it's, like, semi entrepreneurial in a sense. You're also you know, learning how to to sell, which is important in basically anything that you do, whether that's, you know, interviewing, whether that's entrepreneurship, whether that's another job when you're advocating for a pay raise, right, like learning some of those skills are are really important. And so I'm I'm glad I took that job.

Ryan Maruyama [00:14:45]:

Yeah. One of the biggest things that we always tell people or I try to tell people is learning to sell will change your life. And one of the best ways to learn to sell is to go and get a sales job. And I know a lot of people are like, well, I hate talking to people. I hate people. Oh, okay. You know, that that's fine, but we still have to figure it out. the best way that I tell people to get into sales instead of, you know, going the full on entrepreneur route at the very beginning is basically do what you did, and it follows my own career very similarly, which is go and get a job as a salesperson. The reason why is because you work for a company that has a established product or service. You don't have to worry about the fulfillment of it. You don't have to worry about order processing or whatever it is that you're trying to sell. All you have to do is sell it and then more than likely service it, but you kinda just let the fulfillment. All of that, you pan that off to those other people.

Colton Sakamoto [00:15:55]:

Yeah. No doubt. I think, you know, for anyone listening, you don't need a degree to to be good at sales. You know, I'm someone who's more introverted, and so think I can resonate a lot with with you, Ryan, and that talking to people isn't always something you enjoy, but it's a really important skill for everyone to learn, you know, whether that's tech sales, whether that's mortgages, whether that's medical device. My younger brother just graduated college, actually, and he's pursuing a a career in medical device sales. And we're talking a lot about career stuff and you know, my advice to him, he wants to be an entrepreneur down the road too, but it's, hey. You know, get a good job where you can learn to work with a team in a professional environment

Ryan Maruyama [00:16:32]:

where you can learn to sell and sort of develop these skills that'll that'll serve you in the long run. Yeah. Absolutely. Medical device sales is a really good one, and you were kinda touching on it. with the industry as far as real estate, you can sort of be an entrepreneur within the own company. You're gonna have to build your own book of business and Do all of that. But, yeah, there are a lot of industries like that just to give some ideas for those people listening. There's like, Terminix or they'll call it pest control. Anything having to do with, like, the house. There's, like, windows, things like that. Those are really good places to start medical sales is another one. Car sales, at least get inbound leads. So that is just a couple of places to start for those people listening. For you, can we talk about what inflection points was before we talk a little bit more about

Colton Sakamoto [00:17:25]:

how you started it and how it went? Yeah. So inflection points was an employment focused company specifically in the crypto industry. And our goal was basically to, you know, help these companies find the best talent in this new emerging exciting industry. And so while I was there, we help 1500 plus people starting your jobs. We had a job board, I know, similar to, like, a LinkedIn or indeed, but very much more niche. We had a training program which kinda went through where it's networking. It's, you know, you're gonna get educated about what Bitcoin and crypto is, and then you're gonna hear directly from companies on what they look for from candidates. Down the road, we raised some money. We raised a pretty decent size series a, and then we went and acquired the largest recruiting firm in the crypto industry to sort of help fulfill that that mission of helping more people work in the industry. And that was a a traditional head hunting firm. where they go find candidates and they make, you know, anywhere from 15 to 25% per placement in the industry.

Ryan Maruyama [00:18:22]:

Amazing. Now when you put it so succinctly like that, it's very neat and it's very tidy. I'd love to start at the beginning. when you were saying that you started it in your childhood bedroom with your cofounder. You basically said maybe 4 or 5 different things that inflection points was and became to be, at least by the time that you left, is it still an active company now? Yep. Yes, sir. And What can we talk about what it looked like at the beginning?

Colton Sakamoto [00:18:54]:

Yeah. So I actually met my cofounder through Twitter DMs, you know, I I sent them a couple memes. He thought they were funny, and then we hopped on a call, and we sort of came up with this idea to launch a job board. the crypto industry. And so he wasn't in my childhood bedroom with me. I I was there for the record. It was in my he he was not in my childhood bedroom. So we started with a with a job board, and I basically built the job board. It was off the shelf software. So it wasn't, you know, coding or doing anything too intense. It was very much no code. And so I spun that up pretty quickly, and we brought it to market super quick. I think this was January 27 2021. and pretty much immediately gained traction. I can talk about sort of why it took off so quickly, but it was really fun to see. You know, I'd always wanted to be an entrepreneur. I was working this 9 to 5 job. And then I started this side hustle that sort of took off, and it was really exciting. Yeah. This is definitely what I wanted to talk about because there are a lot of people that are listening to this program that would love to get solid paying job

Ryan Maruyama [00:19:56]:

they would love it if they were to make 6 figures, work 4 days a week, work remotely, whatever their goals are. But then once they achieve that, they start to realize, like, Oh, this is nice. I have all the things that I wanted 2 years ago, but I still work for somebody. You know, I still have to ask for days off. I still have to do all the things that an employee has to do. I would love to start at why crypto what the

Colton Sakamoto [00:20:27]:

business model behind a job board is just to give the idea for people that are listening to this that might not have any idea out there of, like, what a business can be. So I think let's start with my introductions to Bitcoin. I'd heard about it, you know, pretty early on, but, like, everyone sort of thought it was a scam, you know, didn't really think much of it, but I had a good opportunity that I passed up to buy it really low. I was a sophomore in high school, though, so I'd this was, I believe 2013 or 24 team. So I think I was a sophomore junior in high school. So I passed on the opportunity then. The wave of, you know, 2017 came, and I actually bought some than an still hold it, you know, from back then, but I didn't really understand. And then when COVID hit, I realized how much money the US was printing and I apologize at the time that inflation was gonna get pretty out of control, and I thought Bitcoin would be a pretty good hedge against that inflation, and I think it's important to separate money from state. Turns out some of those things were true, but I still didn't have, you know, much money to invest. Oh, I'm coming to me and she said, hey. There's this hair salon. They need someone to paint it. and no one's in there because of COVID right now, but they want a totally new paint job. Well, I've never really painted anything my whole life outside of arts and crafts in, like, 2nd grade, but let's give it a shot. And so I went during COVID to the salon and painted the walls, moved stuff around. It was I think I did a good job. You'd have to ask them. I did about as good as twenty three year old, due to what that no opinion experience could do, but I got paid a thousand bucks, actually, which is which is pretty good. And what I did was I took all that money with the exception of I bought 2 pairs of chubby swim trunks because it was summer and why not. But I put I put the rest in Bitcoin And so this was pretty early. And then from there, I was sort of hooked. I just went down the rabbit hole of, you know, what this technology and what it is. And why it's important. And I was hooked. I was getting baseball lessons too, and so I was doing sort of these, like, little side hustle type things. I was taking all of the money, basically, that I was earning and putting into Bitcoin. And the few people that I I did tell were, like, dude, you're crazy. Like, know, because of scam, yada yada yada. I turned out to to be pretty good. I'm happy I I made that decision, you know, if you're someone who's young, and listen to this, you know, find a way to make some extra cash, make that pay off, invest it, invest in yourself. I think that's, that's really important, and I'm really glad I did it. So you've went down the rabbit hole of Bitcoin. You're a believer.

Ryan Maruyama [00:23:01]:

You put in the money that you had $1000 net into Bitcoin. How did you think that, okay, I'm going to start a crypto job board. How did you even know that a job board was, viable business?

Colton Sakamoto [00:23:18]:

Yeah. That's a great question. So I I really went down the rabbit hole, and I was trying to consume as much information as I could. And, obviously, a thousand bucks was a a ton to me at the time. And so it's like, if I'm gonna make this big crazy investment into Bitcoin, I better know what I'm getting into and educate myself. And so that brought me to follow a lot of, you know, people on Twitter and in the podcast space as well. And that's how I met my cofounder. And I think, you know, what really resonated for me is I was someone who struggled in the job search. And so if I can sort of create something that makes it easier, know, for people like myself, and I can solve a problem that I've had, you know, firsthand. You know, that's that's basically why, you know, we decided to launch it in the crypto space. Who was your cofounder?

Ryan Maruyama [00:23:59]:

Anthony Pompeo. And so you just went and DM ed him some memes and said, hey. I can build a job board. What did that? So

Colton Sakamoto [00:24:13]:

so he actually, said that he wanted to hire a chief name officer. so I've been making memes just like with my with my teammates in college on the bus, like, trying to make them laugh, making fun of, you know, coaches or whatever, just any kind of shitty situation. We turned it into a meme. And so I thought, hey. I can I can make some memes. And so I sent him a meme. He thought it was pretty funny. And then We hopped on a call and it turns out I didn't get hired as chief meme officer, but rather, you know, we decided to to launch a company together. ridiculous on l?

Ryan Maruyama [00:24:46]:

What what is a chief meme officer?

Colton Sakamoto [00:24:49]:

You know, that's a great question. I I still don't really know. It's probably similar to a chief party officer, honestly.

Ryan Maruyama [00:24:57]:

Amazing. Amazing. That's awesome. And that makes a lot of sense because I've seen some of the memes that you've posted. And

Colton Sakamoto [00:25:06]:

they're pretty on point. They're pretty good. Some of them really hit and some of them do not. And it feels really good when you know, hits and resonates, and people think it's funny. But I'll tell you what, when you when you post a meme that no one likes or thinks it's funny, it's just It's a different kind of pain.

Ryan Maruyama [00:25:24]:

Yeah. I think that's creating content in general, but especially when you're trying to to elicit, like, obviously, the call to action content is is important and you want you wanna drive sign ups to this or want somebody to buy this, and that's all that that's all important. But for me, when I feel the most pain is when I'm trying to elicit an emotion from somebody, whether or not -- I don't get it. Yeah. I'm just, like, bleeding at the keyboard. I'm like, let me tell you my life story. and or or exactly the opposite, or I'm just like, this is gonna be hilarious. And then you you -- It's not. Yeah. And then it just crickets. and and I will literally I'll press post or I'll press send upload. And then like, a week later, it still didn't hit. And I'm just, like, thinking about that content. I'm like, oh, god. You're so dumb. why why did you why did you press post?

Colton Sakamoto [00:26:22]:

Oh, yeah. It's the worst when you're in a group chat with your friends and you think you did something funny and it turns out they just start roasting you. Like, dude, that wasn't funny at all. Like, go back to the drawing board.

Ryan Maruyama [00:26:33]:

So you guys were starting the job board.

Colton Sakamoto [00:26:38]:

And what software did you use? You said off the shelf? it's called smart job board. Yeah. So it's off the shelf. no code software. And the way the job board works is, you know, companies would come in to pay to post their roles, and so that's how it it drives revenue. And then the other sort of component of a successful job board is is driving traffic to it because, obviously, the company's on there. They don't wanna have their jobs up. and advertising them with no one coming in. So it's a bit of a balancing act between, hey. You want a bunch of companies on your paying to drive revenue. also to drive users, but you also gotta have the users for the company.

Ryan Maruyama [00:27:12]:

Yeah. Amazing. And for those listening, we don't normally go down like, this deep of rabbit holes. I'll dig ourselves out of it in a second, but this is the type of thing that if you are thinking about creating a business, having these little, like, Actionable. Like, I use this thing. You know, I use this tool. We did it this. This is the business model. At least for me, It is very, very helpful to have somebody just explain it all. And at least you have an idea. I mean, like, oh, that's a that's a business, you know, that we can we can actually make money doing that.

Colton Sakamoto [00:27:43]:

Right. I think the the tools are super, super important, but the thing I wanna hammer home to the audience too is you gotta find a way to acquire customers and you've gotta find a way to acquire users. It doesn't, the tools matter. They definitely do, and the product matters. but you have to find a way to acquire customers. you know, that can be done by, you know, getting on social media and sort of telling your story, talking about your product, driving traffic that way. It can be done on on YouTube. It can be done, you know, if you raise money from some investors and they have some ends with company or with other companies, but the tools are super important, but more so, the acquisition strategy for customers, the distribution is what's really gonna take, you know, your your product, your company, to the next level.

Ryan Maruyama [00:28:26]:

Absolutely. Absolutely. And with job boards, there's the classic chicken and egg problem. Correct. Exactly. For those listening, it's Do you just post jobs on there and, like, for free? Like, are you just scraping the internet? and then posting jobs on there for free, or are you going to companies and saying, like, this is a crypto job board wanna post your jobs here? But then the company's gonna ask you, they're gonna be Well, how many users do you have? Like, what's your monthly traffic? And they're gonna be and you're gonna be like, I don't know. 0. Yeah. It doesn't exist. The domain is like, 2 days old, you know, I just bought it. And so when you're going through that beginning phase, How did you guys

Colton Sakamoto [00:29:12]:

attack that problem? Great question. So what we did personally, and I've seen a number of other ways people do this, which I can talk about in a sec, is we went to a few of the more prominent companies in the space. We basically said, hey. We're gonna launch this thing. We're gonna make it easier for you guys to hire you know, people at an affordable price, you know, will you go in and post your jobs for free? You'll be a launch partner with us. It'll get press coverage. and you guys will have free lifetime access. And so we did that with a few of the kind of bigger names going base of Gemini. blocked by it now extinct RIP. We had a bunch of jobs on there. And so when we went to announce the launch, there were established companies, exciting companies on the job board, and so the job seekers were excited by that. The companies that, you know, were were our prospects, we're looking at and said, hey. You know, Coinbase is on here. We should get our rolls up too. And so that's sort of how we solve the chicken and the egg problem. did get a lot of press coverage and drove a lot of users and stuff that way too, which was which was certainly good, but those launch partners were were definitely essential I've seen people, you know, scrape job postings from all over the internet to get started. SEO is a great strategy for people. It just takes a while takes a lot of content, you know, for that stuff to hit. You know, advertising works too, but it has to make sense, you know, from a numbers perspective, there's a number of different ways that you can sort of tackle it, but I think kind of the big thing for us was getting some social proof on there because social proof is is super, super important.

Ryan Maruyama [00:30:38]:

Yeah. And for those thinking about job boards and really any company or any side hustle that you're thinking about, the more that you niche down, the better. Right? So you guys pretty much had a cornerstone on that marker, you cornered the market on those types of jobs. You guys pretty much owned that niche. There are a lot of job boards out there and a lot of companies out there that think, okay. Well, I'm just gonna create a job board for anything, you know, just -- Yeah. Yeah. It doesn't really work that way because you don't you don't have traffic, and then you don't have targeted traffic. So there are a lot of good job boards out there. Jeremy, there's job boards for every different niche imaginable. There's remote job boards. There's content job boards. There's crypto job boards. And then there's, like, Bitcoin only job boards out there. And so if you're thinking about doing a job board or any company, you have to really niche down, think, okay. What am I gonna do? And then am I going to target users? What's my, you know, unique selling proposition?

Colton Sakamoto [00:31:48]:

Correct. Yeah. I mean, the the odds overwhelmingly say that you're not gonna be the next LinkedIn or indeed. And so like you're you're saying, to your point, it really makes sense to corner a specific market where there's a need I think for us too, why we gained traction so quick was we sort of captured the upside of the Bitcoin in crypto industry, you know, on the upswing. And so it was getting a ton of media coverage, a ton of press coverage. And so that sort of was a big catalyst for our growth, just the growth of of the market but I think you have to niche down at least in the beginning, and then you can sort of expand everywhere, Peter Teal, you know, talks a lot about this in his book 0 to 1. He's actually an investor in in inflection points, which is super cool, but talks about, you know, cornering a specific niche, catering to a specific person first and then sort of expanding outwards as it makes sense. Yeah. Yeah. Definitely. I was actually having a conversation with a

Ryan Maruyama [00:32:41]:

software engineer at Twitch the other day, and he was talking about how he positioned his career. He is a software engineer at Twitch, so he focuses on web RTC, which is web real time communications, which is, like, stuff like what we're using right now. And he was just talking the reason why he chose it is one he's super interested in it, but also it is extremely niche. And then it is in incredibly high demand. That recipe of those 3 things skyrocketed his career and his earning potential. And I think that that's a very good framework for anybody listening to this. You could do how he did in his career

Colton Sakamoto [00:33:25]:

or how you did by starting your own company. Yeah. No doubt. I think it the same goes for I've been posting a lot on on LinkedIn and sharing a lot of insights, you know, from the company I started and and stuff that I think will resonate with job seekers. And initially, when I got started, I was riding to a very specific kind of person, and that helped me really gain traction because I knew that person well. I understood their pain points and the stuff that they dealt with, and I could help solve that person's problem. And since I've gained more traction, I've sort of opened it up and became a bit more general to talk my interview stuff, all that, but I think the key point to hammer home is, you know, get started trying to solve a specific person's problems first. and then you can expand outward from there. Yeah. Yeah. Absolutely.

Ryan Maruyama [00:34:10]:

Because you were so closely ingrained in the employment market, would love to talk about some of the problems that you saw commonly for the job seekers. and that you see today for specifically

Colton Sakamoto [00:34:25]:

the crypto industry, but maybe just job seekers in general. Yeah. So when I started the company, you know, as I spoke about earlier, I really struggled in in my own job search. And so it felt a bit hypocritical to kind of create employment focused products when I, myself, wasn't clear on what I wanted to do in my career. Kind of the way I started was Okay. If I could, you know, make my job seeking experience better, how would I design it? And I think that speaks a lot to the training program that we built What it really was was a community of people looking to break into this industry. It was, you know, a big slack group, which is great for networking. was people sharing resources and interview tips and tricks. And, also, we brought the companies in to talk to the candidates directly about what they're looking for. And so it wasn't me saying, hey. You need to do x, y, and z. It was people from Coinbase saying, hey. You know, this is exactly what we're looking for. you know, follow these best practices if you wanna have a chance at working for us. We gotta hear from from startups. We gotta hear from midsize companies. We gotta hear from, you know, post IPO things like Coinbase. And so I think the way we did that was basically just driving, like, the optimal candidate experience and, you know, how we would design the job search and sort of, you know, backing into to the program.

Ryan Maruyama [00:35:42]:

For job seekers out there, especially for the crypto market, one of the things that's so difficult about all of these new and emerging different technologies or industries is finding a good fit within that industry. So, like, crypto They're like, I need so I need a product manager of this crypto product, but Nobody has any experience in this crypto product because it literally didn't exist, you know, 5 years ago. 3, you know, 3 years ago. And I suppose a similar thing now would be, you know, like in the AI space. People are like, you know, I wanna prompt engineer or whatever, like, you know, with 6 years of experience. You know, it's like, it's, yeah, it's it's only been around for x amount of years. as a job seeker, how do you find where you fit in, like, I'm convinced. I wanna work in crypto. I need to work in crypto, but I don't know the different jobs out there. I don't know where I can bring value. Like, there's such new roles popping up.

Colton Sakamoto [00:36:56]:

How do I find my way? I think it's very similar to entrepreneurship in a sense that it makes sense to niche down and you got to kind of look yourself in the mirror and say, you know, what do I wanna do, where do my skills fit in, and sort of that overlap in the Venn diagram is sort of your sweet spot between, you know, what you like doing, what you're interested in and what you're what you're good at. And so I think, you know, only yourself, you can answer that question of, you know, what you want from there, it's just a matter of doing your research and your homework. Okay. Does this company support the values that I support? You know, do I resonate with their mission? you know, do I value the same things they value in terms of remote work or, you know, size of company or autonomy So I think it's first a matter of defining very clearly this is what I wanna do and what I'm interested in. And then from there, doing your research and then mapping out a plan, to to get there?

Ryan Maruyama [00:37:48]:

I would love to fast forward a little bit in your story. And so you major exit from inflection points. And now you're doing this office party, but prior to your office party, you know, launch, you were basically

Colton Sakamoto [00:38:06]:

just making content on LinkedIn of what were you doing? Yeah. So I stepped down in January of this past year. I knew it was time. There were a number of things going on that I couldn't get on board with, so I decided to to leave without much of a backup plan, and it was super hard to do so. I walked away from you know, a really high salary. I walked away from, you know, more money than any twenty six year old should make. I walked away from a ton of invested equity and great apartment in Miami and the company that I had built out of my childhood bedroom. And so it wasn't an easy decision to make, but I feel that it was the right one. And so I stepped down without much of a plan at all, but I said, hey. You know, I I feel like I've learned a lot. I feel like I can sharing my story. I can share, you know, how I struggled in the job search. I can share, you know, some unique clever things that other job seekers did. I can share out about how I help job seekers, you know, land awesome, exciting jobs. And so that's why it took to to LinkedIn. I really didn't know what I wanted to do, but I feel like putting yourself out there and creating content is a good thing no matter what. I would encourage, you know, the listeners here to start to do that, whether that's a podcast, YouTube, Twitter, LinkedIn, Instagram, whatever, you know, you have some unique insights and and value to bring to other people. And I was someone who I very much didn't post on, you know, Twitter linked in anything. you know, prior to my departure, and I I regret doing that. I should've done that earlier. I post a little bit on Twitter, but it literally should be, like, random memes and a bit of shit posting and stuff like that. but then I really took it seriously. I said, hey. I'm gonna post every single day on LinkedIn and just see what happens. And, hopefully, this, you know, resonates with people. And very quickly, it did. I grew pretty quickly on there. It took me, I think, 85 days to hit my first 1,000,000 impressions. And then I think from there, took 39 days to get from 1,000,000 to 3. So the doubling time is very quick. It's a very asymmetric opportunity to put yourself out there and start creating content I've had a lot of jobs, you know, come inbound because of it. A lot of opportunities pop up. You know, I actually grew from, I think, 2000 followers on LinkedIn to now almost 13. 1000, you know, and a handful of months. And so it's been super exciting. There's been times where I've been discouraged and thought, hey. This is stupid. No one wants to listen to my story. the whole imposter syndrome deal, but I just, you know, committed to doing it and and I have good days. You're gonna have bad days. And over the long haul, it's gonna, you know, pay off. And so I'm really glad, you know, that I've done it. It's really helped a lot of people. A lot of people have said, hey. This helped me land a job and sort of those stories and anecdotes are what keeps me motivated to need to to produce content.

Ryan Maruyama [00:40:40]:

Amazing. Amazing. Thank you for sharing that. I wanna make it clear that my question wasn't meant to be like a derogatory clash in. I just didn't know how to make the transition smoothly, but you handled it very well. Thank you very much. And, but, you know, I wanted to key in in a couple of things that you said there, which was, you know, LinkedIn, especially as far as creating, content on that platform. There really is an extremely asymmetric opportunity on that platform specifically for people to gain eyes for everybody listening. Like, well, the reason why is because it's a professional platform. And majority, I think it's like I don't know. Maybe you know this, the stat, but it's, like, 95% of people are basically just lurkers or something like that. And they're -- Correct. Yeah. Like, something that. Something like that. It's something crazy. And 5% of people create all of the content on LinkedIn because nobody wants to you know, post on LinkedIn because they don't want their boss to see that they're having margaritas at their, you know, at their off-site. if you want to garner some sort of attention, LinkedIn is a really good place to do that. Also, because of the nature of the platform where it is not anonymous, you actually have people's faces and their, you know, resume basically right there if you post something that's dumb or that people don't agree with or whatever -- Their identity is tied to it. Yeah. Their identity is tied to it. So there's not as much, like, you're an idiot, whatever, whatever, whatever, whereas, like, you go to Twitter or she come come to TikTok. We get called an idiot, like, pretty much every day. and the YouTube comments is just one dude on YouTube who just literally. He, like, there's that saying, like, living in people's heads rent free. Like, we live in his head rent free. That guy is, like, on every and he's just calling us an idiot. All that's not like you realize the more that you interact with my content, the more that you're gonna see it. Oh, yeah.

Colton Sakamoto [00:42:44]:

Yeah. You'd be surprised though. Some people will come after you on LinkedIn, and they don't care. But, you know, that's a doesn't bother me too much. It's a it's just it comes with the territory. And I think you brought up a a unique point in LinkedIn. Now it's mostly professional. I think that's where the opportunity is to sort of differentiate yourself and capture eyes. You know, most people that are posting, it's just, you know, here's a link to something cool my company did. And that's, you know, great, but, you know, people are drawn to authentic content. Something I've been doing on there is is post names, and it's a bit ridiculous on a professional platform to be, you know, posting memes. I mean, it's absolutely ridiculous, but that's where the opportunity is because no one else is really doing it. And so if there's something that's slightly funny on LinkedIn, it's, you know, bringing in a ton of eyes and and people are engaging that and it is a bit awkward when, like, you know, my friend's dad who's, like, you know, super professional is, like, interacting with with my content. It makes me feel a bit weird I think that's where sort of the the unique opportunity is is on LinkedIn.

Ryan Maruyama [00:43:50]:

I wanted to spend a little bit of time on the content creation and how you decided to do it because exactly your story from what you said is how it looked from the outsider's perspective. Like, before this conversation, we didn't really know each other. We were aware of each other's existence and I followed your content since you've been starting content. I've known about your career at a at a distance from inflection points. So from the outside looking in, It really looked exactly how you said it, which is you weren't creating a lot of content when you were at inflection points when you founded it when you were running it. But now you've stepped down, and now you started to create content. And I will say you're a content machine now. And like, props to you. That's amazing.

Colton Sakamoto [00:44:40]:

How did you get started? Yeah. That's a great question. So I think a couple points there. You know, I was running the company. It was very busy. And so I wasn't thinking about content at all, and I should have been because it's important, but I just, you know, wasn't making the time to do it. I stepped down I've always enjoyed writing. I've always enjoyed the memes, like, instead of making people laugh. And so that part, you know, wasn't too difficult for me. It was just a matter of, you know, how can I sort of write, you know, my story, other people's stories, anecdotes, and data points in a way that'll resonate and help people. And so, you know, really, it was experimentation. It was just getting on LinkedIn every morning and just letting something rip. and sometimes it was really good, and sometimes it was really bad. And then from there, I had some data points as to, you know, what worked well, what resonated well, I can sort of craft my strategy around that. you know, I do some other things where, you know, I just go on a walk and sometimes something pops in my head, so I just throw it in the notes app. or I see someone on LinkedIn doing with a particular pain point that I don't how to address. And so I turn that into a post. You know, I see a funny meme, I repurpose it to be more, you know, career related and resonate with people who are, you know, in the office. And so it's very much experimentation but I think the big thing to hammer home is just being ultra, ultra, consistent. I post every morning at, you know, 9 AM EST, I usually post 2 more times on weekdays. Those are usually more like memes or sort of quick hitters that I post once on weekends too. So it's an everyday thing, and it really doesn't take up that much time. I think people, you know, eat up all this time, which I thought prior to doing it. it really doesn't take me too long to write a solid LinkedIn post. If you're on the fence about it, I would just start laying a rip and just, you know, experiment and see see what works. A couple other things that have helped is just engaging with other people's content, leaving insightful comments, useful comments on other people's stuff. you know, that really helps drive people to to my LinkedIn and, you know, helps build trust and and community.

Ryan Maruyama [00:46:41]:

How often are you creating content out of your day or of your week. Oh, man. I do 3 posts on weekdays. That usually takes,

Colton Sakamoto [00:46:48]:

honestly, 10 to 15 minutes a day if I'm gonna you know, let 3 rip on a day. I mean, if I'm doing, like, a longer form 1 or a carousel or something like that, it takes a bit more time. I'm not great with, like, design and stuff like that. So I'm, you know, messing around in camera longer than I probably should, but it really doesn't take too long. I think you know, it helps to ideate and go on walks and and sort of think about everything. Jerry Seinfeld had a good quote where he was like, everything is a bit. And so he's going through his day with this lens of I'm looking for a bit and everything I do, intel proven otherwise. And so know, maybe something funny happened at the gas station. That's a bit. Maybe something funny happened when he was, you know, walking his dog. That's a bit. The same with content. I'm looking through the lens of everything is content until proven otherwise. And so that turns out to be, you know, pretty helpful in sort of the ideation process and to help streamline things a lot as well. Do you

Ryan Maruyama [00:47:43]:


Colton Sakamoto [00:47:44]:

Do you use a scheduler? So I do. LinkedIn has a scheduling feature, and so sometimes I'll schedule, like, the memes further in advance. Sometimes I'll schedule the morning post in advance. Like, if I know, I'm gonna wake up later than, you know, 9 AM Eastern time. I'll schedule it out in advance. So I do utilize the scheduling feature just through LinkedIn app, though. Perfect.

Ryan Maruyama [00:48:05]:

And I did wanna backtrack and talk about the value of creating content for those people listening. And we dove into the how to and the nitty gritty of it all, but touching on what you said before, which was by creating content, by putting yourself out there, you were able to work with different people. You are able to get job offers from different people, and it's the same thing for everybody listening. And it's just Something that I say all the time on this podcast is just doing things in public. And content is one of those things. It's the easiest thing. that you can do in public. Good example is you starting your LinkedIn content creation journey prior to the office party even being a thing. And for us, we started degree free when Hannah and I both had full time jobs, and we were running another business. There's no business behind a podcast. We were just like, I don't know. Let's just start talking about these things that we care about. And, hopefully, in the future,

Colton Sakamoto [00:49:13]:

it'll it'll pay dividends. Yeah. It's intimidating to to put yourself out there and as I shared, I'm more introverted. And so I kinda want to, you know, I tend to not wanna share things, but I really had to step outside my comfort zone and battle some imposter syndrome and you know, battle some of the ups and downs, but I think, yeah, putting yourself out there is super, super important. There's basically infinite potential with it. It's a massively asymmetric opportunity. downside of posting more is, hey. I might waste some time and nothing comes a bit. The upside is, you know, job opportunities. It's entrepreneurship. It's investment opportunities. It's all sorts of things. But those things will never come to you unless you start to put yourself out there more. The upside is basically uncapped. And what I'm seeing now is it was slow, slow, slow, slow, slow, slow, and then it starts to exponentially increase. So it's important to play those sort of asymmetric games. It was similar to where I wanted to invest in Bitcoin. I saw the asymm through there. Basically, the upside is uncapped. The downside is 0.

Ryan Maruyama [00:50:12]:

Yeah. Totally. Totally. When you're talking about the downside, and experimenting and things. A lot of people are thinking, well, I don't want something out there, and I don't want to be out there if it's crappy. Like, I only wanna put out great content, and that's all I wanna be known for, which is totally understandable. I'm in that same boat. the reality is that if you just post it and it's crappy, nobody's going to see it. nobody sees it. Nobody remembers, but everybody remembers those things that go viral. I remember when you said x or y, you know, and content is one of those things that it's like that. And mister Beast talks about this. I forget he was on Rogan or or whatever, but he talks about it's much easier to create a video that gets, like, a 100,000,000 views than it is to create a 100 videos to get 1,000,000 views each. If you're not in the content creation space as I wasn't, you know, years years ago. That didn't make any sense to me. You know, you're just like, I don't even know what that means. Right? But You just have to get out there and experiment. And if you're flooding everybody's feed with content that you're always optimizing on it,

Colton Sakamoto [00:51:31]:

you're gonna hit on something, and eventually something's gonna take. Yeah. You have to really sort of battle your own self doubt. And really the worst that can happen is, you know, your friends arrest you in in a group chat or something like that, which it's not the end of the world. Those are your friends anyways. So it doesn't matter, but you have to, you know, be willing to to put yourself out there and to ship fast, it's easy to say, like, oh, I'll start doing it next week. And then next week rolls around, you go, I don't really feel like doing it. You just have to commit to doing it and commit to being, you know, consistent with it. And eventually, it'll hit. You'll find out what'll work. You'll take that, you know, sort of feedback from the market and forward your strategy moving forward. it's very much the same with how we built the training program. It's like, hey. We're gonna put this thing out there. People are gonna, you know, give us feedback on the surveys. They're gonna message us feedback. we're gonna tweak it and we're gonna iterate, and it's never gonna be a finished product. It's the same thing, you know, with with content creation. You're putting something out there. and then you're tweaking and iterating, you know, based on feedback from the market. Yep. Absolutely.

Ryan Maruyama [00:52:33]:

Can we talk about the importance of distribution in entrepreneurship and then it really in in any job. out there. There's a saying that and I don't I don't know who says it. Abraham link Abraham Lincoln herself. Well, you know, I don't I'm not sure. Yeah. Right. Yeah. Thomas Jefferson, one of those guys, and it was, like, first time founders are focused on like, the product and sales and everything like that. And then the second time founders are I'm botching this, but second time founders are focused on distribution and how and how we're gonna get out there. And so I would love to just talk about, like, what are the plans for office party going out there now that you have this new thing. What is the plan for distribution and getting it out there? Is it just LinkedIn content? Or is there is there a greater plan?

Colton Sakamoto [00:53:29]:

Yeah. So with office party, I have this absurd goal that I put out there. And so it's out there on LinkedIn. and so people can hold me accountable to this. I have an absurd goal of getting it to a 100,000 free subscribers in 1 year, which is totally, totally absurd. That's gonna require a massive growth, but I think it can be done. I believe it can be done because of the asymmetry where we're gonna start here, and then, you know, we're gonna start to do some things that are really gonna take off. We're gonna find the strategies that work better than other gonna double down on those, but the plan is to to really grow and scale it. LinkedIn content creation is a good funnel into the newsletter. I'm at almost 13 k now. I think by the end of the year, I'd like to get up to 30 k or so and convert a lot of those into the newsletter right now, it's doing a lot of things that don't scale. So I'm literally messaging my connections on there manually saying, hey. You know, will you subscribe? It's free. I think you'll like it. then there's a bunch of other sort of, like, step function things that I think will happen, one of which is just the growth of of My Linkedin by Tyler who doing this with me as well. He's been posting on Facebook and HR groups, and that's driven a ton of sign ups. Reddit is another great strategy. And so there's all these sort of, like, free sort of unscalable things that we're doing right now that are really making a difference. We're at 1500 subscribers after 1 week, which is pretty damn good, and the feedback on the content has been positive. And then you start to see other things like people start to share it with with other people they share it on their LinkedIn pages, their Facebooks, their Instagrams, or they forward the message directly to to other people. There's all sorts of things like referral programs with other creators and newsletters that we're capitalizing on. There's, you know, paid ads. There's all sorts of late magnets and giveaways that you know, we're gonna do as well, but it's just a matter of gaining that initial traction, you know, being willing to sort of persist through that pre hyperbolic phase. So I think the getting started part is is gonna be a challenge. It's gonna require a lot of manual effort, but I think once we get to 20 k or so is when we start to see a lot of those step function changes where things start to go vertical. And a 100 k is the goal. There's been a couple of newsletters that have done it. The Mope Road's a great example. They sort of capitalize off the away. Superhumans another one. They're at, like, 300 k in, like, 8 months, which is absurd. They're sort of riding the AI way. And so these things have been done. know, part of it, I think, is the industry in which they're operating, but I think we deliver something valuable and the feedback has been good. And so I'm super optimistic that we can reach that stretch goal So with a newsletter,

Ryan Maruyama [00:56:02]:

what is the business model? Like, it's free to distribute or it's free as a subscriber. So everybody 1, everybody should sign up. But then as a business,

Colton Sakamoto [00:56:14]:

how do you make money? Yeah. Great question. So I thought a lot about what I wanna do post stepping down. and there's all sorts of job seekers products that I create consulting, you know, recruiting, etcetera, etcetera. And, ultimately, I just didn't wanna charge job seekers at this point. And so what I wanted to do is create a bunch of free information, whether that's on my LinkedIn or or through the office party, and just make everything free and super valuable to people. And the way to to monetize it right now is we're referring subscribers to other newsletters. And so when they go through the sign up process, they sign up with office party at 3, and then they're prompted to join a couple other newsletters who then pay us for the referrals. And so that's a good way of sort of getting started to make some quick and easy revenue. From there, once it gets big enough, paid ads will be a big one. So HR is is a high value niche. So companies, whether that's an applicant tracking system, whether that's a LinkedIn or Indeed, you know, will pay to advertise and get in front of these HR career professionals. The ad monetization strategy is a good one that we're gonna be utilizing down the road. Off the back of that, you can also do, you know, paid communities products and things like that too. I'm not so much thinking about that right now. I'm more so just focused on how do we drive as many free sign ups as possible. and then monetize down the road. So it's a bit, you know, challenging to look and to not make a ton of money in the short term and to think about this from a a long term perspective, but I'm confident we do the right things, you know, it'll it'll pay off down the road. And there's, you know, just so your listeners are clear, like newsletters are are a great business. You still have to build the distribution, but there've been a number that I've sold for, you know, 7, 8 figures. Morningbrew sold part of their business for, like, 65,000,000 Milk Road. I'm not sure how much, but it was 7 figures, a peak, which is a Canadian newsletter. They just sold for 5,000,000. So, you know, these things are are businesses just gotta really find a way to scale them. Yeah. Definitely. Newsletters can be great businesses.

Ryan Maruyama [00:58:09]:

Some people say that newsletters are dead or that email is dead. But, really, it is one of if not the most intimate form of communication that we have with people. you arrive in their inbox every Tuesday Thursday. Ideally, they tell their friends about it and everything like that, but you can also just consume it quietly. The outside world will never know. So it's one of those things that you can be like a closet office partier.

Colton Sakamoto [00:58:39]:

Exactly. Exactly. And the thing to hammer home about the importance of email is, like, social media can lock you out. You can get hacked there's talks of tick tock being shut down. I don't think that'll happen, but when that stuff goes away, you're kind of left, you know, sitting there empty handed. When you have an email list, like, you have the email list. You can continue to email them. And so I think it's important to sort of drive people off the platforms into something that you own more intimately.

Ryan Maruyama [00:59:06]:

Totally. Being reliant on the platforms to you know, not ban you. And then on the flip side of, like, just not banning you, also distribute your content is very volatile. We see it in our business, like, the reason why we have a free community that people can sign up for. And I had a conversation, like, 18 months ago or so with this guy who is a little further ahead in the entrepreneur, you know, space than I am. And he was just like, you need to go and start a free Facebook community right now, Facebook group right now. And I was basically telling him, was like, our content gets flagged on Facebook all the time. And, like, it constantly gets taken down, like, people really don't like our content on Facebook. And and apparently telling people that they don't have to go to college, is illegal because it gets flagged all the time. But so that's just a example from our own experience.

Colton Sakamoto [01:00:11]:

Yeah. super important to to own the audience and the algorithms change. You know, I've had times where I'm like, this post is gonna hit, and then it does nothing. And it's like, maybe it was me, but, you know, potentially there's another factor, which is the algorithm. And with email, it's more sort of black and white. You know, people like to content and open it, or they don't. is getting a little granular,

Ryan Maruyama [01:00:31]:

but you can read a lot of these different articles online And they are telling you how to start a newsletter business and, like, how to do all of these things But since I have you here, at what point do you start to go out and go and sell ad space on your newsletter. Is it at 2000 subscribers? Is it at 5000 subscribers? And then at the same time, how as the entrepreneur do you think about

Colton Sakamoto [01:01:06]:

acquiring those customers? That's a great question. I'm still in the very early innings here, so I don't wanna come across like I'm an expert in in building a newsletter. Hopefully, a year from now, we're catching up again, and I'm at a k, and then I could be the the newsletter expert. I've consumed a lot of content around newsletters and, you know, was pretty methodical about the research that I did. my advice to the listeners here is is learn by doing. Don't use YouTube and social media to procrastinate, you know, get started and learn and iterate. and consume that content simultaneously, but don't use the content to sort of, you know, procrastinate. I think in terms of you know, your ad question, the general rule of thumb that I've heard is around 20,000 is a good time to start selling ads just because the audience size is significant at that point. and basically leading up to 20,000, all the efforts should be focused on growing the list, growing the list, growing the list. From there, you know, from a pricing perspective, then it starts to make sense for companies, you know, from an open rate and the click through rate starts to make sense for the companies to invest in the advertisements So the way I'm thinking about it right now is how fast can we go from 0 to 20 k and just really drive subs? And then from there, start to So I had we've actually already had some inbound interest come in, which has been really a positive sign of people saying, hey. How can I advertise in here? I've turned them down because we're not ready to to do that yet. I just wanna grow, grow, grow, and and write good content. But I think from there, it'll be a mix of you know, going outbound to companies that sponsor other newsletters, you know, that are looking to get in front of a high value niche of people, but also I think, you know, our reader base provide a lot of leads inbound because they, you know, really enjoy the content as well. Perfect. And, yeah, I definitely wanted

Ryan Maruyama [01:02:47]:

to get into this because for the audience, it is really nice to talk to somebody who is in the growth stage of the process. Right? Like, they get a little bit of a snapshot of where you are, and they can see that, hey, maybe Colton doesn't have it all figured out. Right? Like, you you have a good plan, but, exactly, maybe when we catch up in a year, it's gonna be completely different. Maybe office party looks totally different, but at least right now, you know, they can see, okay. Well, he's got a good plan. but maybe it doesn't maybe it doesn't work out. And so maybe that's the same thing for me. Maybe I should just make a plan and then just start doing it.

Colton Sakamoto [01:03:32]:

Yeah. Exactly. I think there's a lot of great content out there, but I think a lot of times you hear a lot of survivorship bias, which is like I just did a few things and then, like, worked out great. And a lot of it was, like, you know, the time of the market or, you know, certain things by your way, and it a lot of luck and obviously props to the entrepreneur for for making stuff happen. But I think kind of getting down to the nitty gritty and and following along the way, you know, is important and there's a lot to learn from that because to your point, the office party could look totally different in 6 months, a year, 2 years from now. I just don't know what that'll be. And so I think following, you know, that along is is super important for for your listeners as well. know, one thing that I'm doing is I'm building this thing in public on LinkedIn. So I'm actually creating content around the growth of the newsletter. And what that does is a number of things. One thing it does is it creates buy in, you know, from community of, hey. This person has this outrageous goal. know, he's gonna go try and accomplish it. I wanna be a part of this. It also attracts, you know, like minded people who say, hey. building a newsletter. I'm struggling with these things. You know, your post really helped me and vice versa. I can learn from them and the things that have really helped them. And then the third thing that it does is it, you know, potentially brings in advertisers. They know, hey. You know, we have 20,000 subscribers at a 50 open rate thing. That's pretty good. I wanna get in front of, you know, 10,000 people every day. I'm going to advertise with this. So I'm building this thing in public. I wish I could have a crystal ball and, you know, exactly how it's gonna work out, but the truth is I don't. I'm gonna build it in public and and see what happens and iterate along the way. Amazing. My last thing, I don't wanna take up your whole day. But I wanted to key in on something that you said,

Ryan Maruyama [01:05:12]:

which was don't use content to procrastinate. That is such an important point. There are so many things that you will consume when you are trying to Like, just get out of this position that you're in. Like, for me, for example, the way that I got out of the restaurant industry and the way that I got out of the bartending lifestyle, and there's a whole lifestyle it. Right? Like, you're just drinking party every single night. And, like, I didn't know anybody that was outside of that sphere. So what I did was I listened to podcasts. like, on my walk to work. I had a 45, 30, 45 minute walk to work, and I would listen to podcasts all the way to work. That content helped me to expand my mind of what was possible, help me to surround myself in air quotes with people that were going places that I wanted to go or already at places that I wanted to go. It did help me change my life, make different decisions, see my goals, and my problems clearer, but at a certain point, It did become procrastination. It did become entertainment. It's such a fine line of where that is. And something that I still to this day struggle with. I'll listen to maybe some job seekers stuff, or I'll listen to some marketing or entrepreneurship content. And I'm like, oh, I'm gonna implement this in my business or I'm gonna do this with my stuff. But then 5 hours later, I'm still I'm like, watching my 7th TED Talk on whatever or my 7th sales presentation that's got, like, 73 views on YouTube, and I'm, like, 5 of them. I'm, like, wait a minute. what's going on? Or shouldn't I just, like, go to my computer and, like, get this done? So where is that line of using content constructively and procrastination?

Colton Sakamoto [01:06:58]:

Yeah. I wanna be very clear. Like, I think content is great. I think you should definitely do your research, do your homework, learn as much as you can, but I think a good way of putting it is, like, you know, say you want to get healthier, get stronger, right, you know, and so you start consuming all this content about what's the optimal way to go to the gym. You know, what's the best time to go to the gym? What's the best supplements that I need to take? What's the latest diet that I need to be doing? What strategy should I be using in the weight room? when in reality, all you need to be doing is going to the gym. Right? And so it's like, it becomes this form of procrastination where oh, I wanna, you know, get everything perfect before I go to the gym where it's like, no. The person that's really gonna see results is someone that's going to go to the gym every single day. and they're gonna consume the content, you know, simultaneously, but it's not one or the other. They're gonna be doing both, and they're actually gonna be doing the thing that's gonna be making an impact And so I think for your listeners, the key is to do the thing that's gonna make the impact. You know, it's okay to learn and consume content, but don't let the content take away from doing the thing. Sometimes you just gotta do the damn thing.

Ryan Maruyama [01:08:04]:

Yeah. Totally. And I I totally agree with the, the working out example. That's a really simple one. I mean, I've gone down that rabbit hole myself of like, man, what's the new workout? I'm gonna go do that. We're like, why don't I just go downstairs and like, bang out, like, 300 push ups. And -- Yeah. Why don't I just go on a walk. Right? Yeah. Exactly. You can listen to the podcast as I'm on a walk, but podcast itself is not gonna make me stronger. Yeah. Exactly. Exactly. And then a couple of last questions before we go. Colton where can people go to follow along with office party and LinkedIn? Where can we send people to follow along with what you're doing? Yeah. So the office party is

Colton Sakamoto [01:08:45]:

It's free. So go sign up. Tell your mom. Tell your sister. Tell your cousin. tell your wife's boyfriend, tell everyone about about the office party. LinkedIn, you can find me. I'm just Colton Sacamoto. I'm posting on the lamp on the other socials as well, but don't post so much on there. So, you know, if you found this valuable, go check out the information on LinkedIn. I try and provide as much free value there as possible, you know, with some good humor and some shit posting in memes. So coolant Sacamoto. That's s a k a m o t o on LinkedIn. Perfect. Perfect. And for everybody listening, I'll have links to everything. atdegreefree.coforward/

Ryan Maruyama [01:09:18]:

podcast. You can check it out there. And last Colton, thank you for taking the time. Is there any

Colton Sakamoto [01:09:25]:

last words, requests, or words of wisdom that you'd like to tell the audience before we go? Yeah. Thank you so much for having me. I wholeheartedly believe in in your guys' mission, and and I do tend to think degrees are overrated. And if, you know, something hits home with your listeners, it's, you know, put yourself out there, be willing to take risks, you know, go try and start something on your own, but you're not gonna do it unless you get started and try and you persist. And there's gonna be ups and downs. There's gonna be a lot of times where you feel like quitting. the good things are are worth persisting through and they're worth doing right. And so, you know, stick it out, put your head down, get to work. It's not gonna be easy. I'm not gonna sit up here and tell you everything's gonna be, you know, roses and sunshine and things like that. It's gonna be hard, but, you know, it'll be worth it. So create a good process and and stick to it.

Ryan Maruyama [01:10:09]:

Awesome. Amazing. Colton, thank you so much for taking the time. Thank you so much for having me. How was that episode? Colton dropped some knowledge. Remember that you can always come back to this episode, and you can go over the actionable steps that he's taken. to create content and how you can use that for yourself or to start your 1st business or your side hustle. Do me a favor. With this interview, I try to do something different than all of the interviews that we've done before. I try to go deeper into the weeds on our particular subject, mainly content creation, starting a side hustle entrepreneurship. Let know how you like that compared to all the other interviews that I've done. If you liked it in the future, I might start doing the podcasts more like this where we go deeper on one subject rather than going all the way into their past and telling their entire story. I would love to hear your comments, either go to YouTube or you can join the degree free network by going to degree free dotcoforward/network and you can comment on the threads there about the degree free podcast. Let me know what you thought of this episode and let me know what you thought of this interview style. Personally, I really liked to get into the weeds and get really, really actionable content on very, very specific things. but I also feel like I lost a lot of listeners. So let me know what you think. Go to YouTube, sign up for the degree free network. And if you haven't already, go to degree free dot co forward slash newsletter and sign up for our free weekly newsletter. And that's pretty much it until next time, guys.

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