Freelancing, Hiking The PCT and Paying Off $17k Of Debt



Sterling's success has been amazing.

In the last six months, he's:

  1. Paid off over $17k in credit card debt,
  2. Increased his income as a freelancer by becoming a revenue producer, and
  3. Budgeted his money to live out his desired lifestyle.

His story's below.

Along the way we've highlighted key learnings from Sterling's journey to help you make similar changes for your life.

If you want to jump around here's a table of contents.

Let’s start!

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Alright, man. Let's roll. What's your background? Your money story?

So I grew up in Texas, in a pretty middle class town just North of Houston.

As a kid, I remember my grandpa would always give me a $100 bill for my birthday.

It felt like the most money ever. I’d hide it in this used DVD case in my closet and try to save it as long as possible.

I was all about saving money.

So after I college I moved up to San Francisco and straight into $1200/mo rent.

That $1200/mo was more than half of my income then, which thinking back on it was totally insane.

I was living in an expensive city and to do normal things it was just like I had to spend money.

It made it tough to get in a habit of saving then because I was just draining everything just to simply hang with friends.

At the same time, I also had moved in with a group of older, more established guys. And yeah, they weren’t trying to eat $2 tacos every meal. hah


I guess in the beginning period, I tried not to think about my finances.

It was my way of coping.

If I didn’t check it, it wouldn’t stress me out. So I hid my personal finances. Buried ‘em. haha

And slowly I started to have some credit card debt. But over time it started to snowball.

God, I mean I even knew that it wasn’t cool back then.

I remember thinking I’ll just make more money and pay it all of then, which I guess is what happened, but it just took longer than I would have like to get started.


What job were you working at that time?

I was joining the startup thing trying to get into marketing.

And I guess another curveball hit around that point.

After 3 months of my first job I got let go because the start up I was at didn’t raise as much funding as they had planned on.

It made sense. I was entry level, fresh out of college with no experience to keep me on board.

Income Security

Your next paycheck isn't always a gaurantee. Keep tabs on how volatile or "at-risk" your income stream is.

Here's a great list of 10 things you can do to lessen the risk of your income stream running dry.

My goal was to just get hourly pay at like any rate. Haha

I wanted to be doing marketing stuff, but I was willing to do anything to get in somewhere.

So I called this company I had interned at while in college. They were just about to launch a product, needed some extra marketing help and offered me a position doing basically admin stuff.

But they told me they’d take the marketing stuff as it went.

And so it was kind of like I had to prove myself.

I had to learn on the go. I had to just figure out how to use marketing to help grow the company and app.

It was a super cool process for me.

There’s kind of two schools of thought around growing your skills:

  1. Go to a big company like a Google and get trained, or
  2. Go scrappy and figure it all out.

I’m really thankful I went the scrappy route. I learned a lot from it. And I think it’s more fun too.

It definitely has higher “highs,” lower “lows” but I liked the challenge.


After a few years at that second job, you took off to hike the Pacific Crest Trail, right?

Yeah, so I in January of 2016 I was mapping my yearly goals and that was one.

My current job was cool, but I knew it wasn’t the end all be all.

So I talked to the CEO, and he was super receptive to it.

He actually suggested I take on work on the side to supplement funds for the trip and my future life.

That’s where I got my first freelance client — through connections from my job and current work.

So as I took off on the trail, I was able to coordinate on/off work with my client.

And on May 7th I took my first step of the five month hike.

Make Money While Traveling

Keeping an income stream going while traveling can help you return from traveling without the stress of $0 in the bank.

Here's a great site to use to find remote work while you travel.

Though be aware that working while traveling does take away from the "freedom" of traveling that comes from hard work and stashing up front. Sterling comments on this below.



So as you were on the trail what was happening?

When you’re on the trail things are cheap.

Your day is just made up of walking.

I probably spent around $7k for my 5 months. And I wasn’t at all the most frugal. Nor did I really want to be at that point.

That definitely contributed to some of my debt.

As cool as the PCT is, it’s a lot cooler when you’re net positive.

If there’s something I would revisit, it’d be telling myself to do it net positive. It’s just way more sustainable.

So what happened while on the trail was I took the false security in using my credit card as opposed to using my debit card.

My thought was that I wanted to keep the $5-6k of cash I had on hand to pay rent when I came back.

But then the interest started to build up, and then I was just like, “Ohh, shoot.”

And then I got back, and I kept that false mindset that it was safer to use a credit card then to use my cash.

I definitely learned you don’t need to do that. Haha

Use a Credit Card, But Pay It Off

Using a credit card isn't bad. But using it and not paying off 'last period's balance' in full every month is.

The best thing to do here is automate your entire personal finance system, including your credit card payments.

But I wasn’t doing anything except spending every second outside walking. I wasn’t buying a bunch of stupid shit.

And I was eating cheap, horrible food. But it all tasted amazing because I was working for it.

My happiness level was at an all time high, and I was spending almost nothing.

It seems cliche how simple it is.


I remember when we first met.

You had come back from some awesome long term travel. But you also came back with credit card debt from beyond your trail time.

What had happened? What were you feeling?

Yeah, so I was very much scrambling around when I got back from the trail.

I had like $8-$10k in credit card debt when I got back.

And I still had this thing in my head to not think about money as much as I should.

So the first thing I did when I got back, actually before my first paycheck (I actually got an advance), was go straight to buy this truck.

It was an ‘82 Toyota flatbed.

The idea was to build out a frame on the back, live in it, work and payback my debt that way.


I thought it would allow me to save money rather than renting back in San Francisco like I had been.

So I told my dad about it, and he told me he knew this guy in Texas that could do exactly what I wanted for pretty cheap.

I was like, “Cool. I’ll make the road trip. I need to put the truck to the test anyways.”

Off I went.

And a few days in, the truck broke down in Marfa, Texas.

So after some mechanic fees and making it to my parent's place, my goal was to get the car running, add the frame and get it back to the Bay Area.

I had the frame put on, but it had cost $1500, and I had already paid $3k for that stupid truck.

And again I was putting all this cash into this idea, so I was still living on credit.

I kept having this mindset of once I get this truck up, I’ll pay it off the debt.

So after Christmas I tried to head back and it broke down again in El Paso. haha

I ended up having my buddy towed me back 8 hours with the truck on a Uhaul all the way home.

The truck never happened after all that. Haha

It’s still at my grandma’s house in Texas. I actually think my dad showed it to someone yesterday. Jeez! Haha

The Art Of Purchasing A Car

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So I flew home to actually take off on another adventure.

While I was on the PCT I had previously decided to purchase this ticket to Southeast Asia with my friends as a reunion trip.

While I was on the trail it was just like I had to do it. And I wasn't paying attention to my finances.

So when I got back from all that in February my debt had snowballed to almost $18k.


This was right around when we started to get going with coaching, right?

Yeah, I was totally scrambling.

All this stuff was falling apart — my living situation, my truck, my finances.

Work was still going okay.

I thought that when I came off the trail I could just sprint for the door, get out of the door and I’d be all good.

But it just didn’t happen that way. And I ended up digging myself into a deep hole.

If everything went according to plan it would’ve been sick, but it just didn’t.

I just swung the pendulum to other side, and I knew I needed to buckle the fuck down.

Clearly, I had been the opposite of "buckle down." haha

I came across The Hidden Green from a friend, and was like, “This is sick.”

I’m a sucker from self improvement stuff. But it was like spot on and I could use the financial help.

My problem wasn’t, “I need a Roth IRA right now.”

I needed to fix my lifestyle. And I thought that was something we could do together.


We’ve worked together for 6 months now, and you just paid all $17k of your debt off. Congrats, man. Not easy.

What's been some of the most helpful changes you've made money-wise over the last few months?

I guess getting to a point of knowing how much my daily budget is. Like knowing this is what I spend usually on this and that.

And then putting a few limits on myself. Simple stuff, like not buying a meal over $10 today.

And also, just taking action. Having a coach there to just say, “Nope, we’re going to do this and here’s why.” Was really helpful.

My biggest weakness is to procrastinate. Like I said, even if I had the cash before, I still wouldn’t pay the debt off.

I didn’t want to face it or check my account. But forcing myself to do that every week was really helpful.

Before I was ashamed about money. It pissed me off. But it really became approachable, doable, an “I can crush this” type of thing.


Another big thing was the alignment of lifestyle and goals.

That was a big selling point for me.

The Hidden Green isn’t just a Dave Ramsey save money thing.

It’s like a how can you hack your life to actually live the life you want to be living.

Start By Defining Your Beautiful Life

Most of the first world builds life around money. What you should do is build money around your life.

That starts by becoming crystal clear with what you want out of life. Then you build money back into that picture.

My friends and I always chat about how we can get past living the lifestyle of everyone else.

And it was cool to have a program that doesn’t subscribe to that norm.

It didn’t just help me financially, but it set me up more than that. That’s a whole another side to it.

There’s a lot of blog posts out there telling you to create the life you want.

But it was just cool to combine that with money because that is actually what you need to focus on to make it happen, not just, "Follow your passion." you know?


You and your friends do this awesome “Goals Trip” thing every year. Tell me more about that.

Haha, Yeah the idea came from my friend, Brendan.

The idea behind it was kinda how a president has his cabinet around him to go to for different needs, help, etc.

He wanted to surround himself with a group of friends that were strong at different things.

So we gather a few of us up once or twice a year and go to town on goals, personal development.

We’re like, “What are we struggling with?,” And brainstorm how we can solve it.

It’s been a cool way to hold eachother accountable.

In reality it’s kinda like we all go surf all weekend and talk about goals for two hours really. Hah

But it’ll be cool if we are still doing it in 15 years. That’d be so sick.

Taking that time once a year is important. And we send each other updates on it and stuff every once in a while.

I don’t know how effective it is really. Well I guess “not effective” in the sense that everyone is not hitting all their goals or doing everything on their list.

But just having a support group is huge.

Importance Of Accountability and Support

Sterling is right on here. When he told me him and his friends did this, I loved it.

If you don't have a supportive group around you, build one. It could be as simple as sending one friend an update email once a week.

It's also a great way to stay in touch with friends who are out of town.

We’ve just built it into our ethos as friends.

Half of the shit we talk about is what we’re trying to do.


If you could talk to 22-year-old Sterling, knowing what you know now, what one piece of advice would you give him?

So, at 22 I would have been finishing up school.

You know, I’d tell myself, “Yo, Go learn as much as you can online. Go learn how to run ads. Reach out to people and simply ask, ‘How can I help you?'"

If I had my hand on how to generate more income for myself then, it would have been huge to know.

A lot of people still don’t have that control when they get employed.

But the crazy thing is once you figure out people pay you when you create value for them there’s literally no ceiling.


If I need to make more now I can take those steps. I may fail, but I have some sort of control over that.

In college I had this thought that “I can’t make more” at this point.

But I mean if I had just taken control over income at that point, it would have been ideal.


So how have you taken more control over your income now?

I’ve justified it.

I go out everyday now and focus on adding the most value possible to my clients.

In an ideal world this value is a simple return on investment (ROI) — “If I do this, you make more.” — but if you’re ripe out of school you may not have that many skills that can do that.

But you can save people time.

Just everyday take actions by making people’s lives easier. People will pay for that.

It’s funny. It’s kinda hard to see into the income-side until you see it for yourself.

Become A Revenue Producer

Most people are just another expense for a business. They are a warm seat in a chair doing the minimum to get a paycheck.

If you want to make more, then you need to figure out how you can help the company make more money.

This can happen in any position. We teach this in our free 9 lesson course and call it being a revenue producer, not another expense.

And number two is something client told me once.

He said, “It’s important to add value. But part of the game is someone has to believe that you’re valuable.”

That’s what keeps you around and growing.

If it’s not a ROI driven thing, then as long as the person feels good about having you around then you are providing some type of value.

Don’t go do this just to promote a facade.

The point though is to just remember that you have to show your value, and make sure your client, customer or boss recognizes you are adding value.


So what's next for you, man? Where do you want to go from here?

That’s something I think about all the time.

I’m still in buckle down mode.

I’m still working hard and getting things in a pretty good spot.

I guess my freelance work is a focus.

I want to build out more of a team for two reasons:

    1. I know that working alone is not going to be a sustainable thing for me.

    2. I want to be more able to scale the value that I bring to someone.

I find myself doing things now that I don’t have time to do.

Better said, I could provide more value somewhere else, but the task just has to get done.

I’d like to have extra hands or automation on deck, that allows me to work less and provide more value.


So that’s a focus right now. But long term…

Yeah, I think about leaving San Francisco. But it goes against my focus on work and balance to get straight in my life.

I’ve been in San Francisco for 4 years. And four years to me represents a college career. It’s holist time to be somewhere.

As I enter into the next four, those determine a lot too.

But yeah, I’m also a millennial 20-something that wants to explore the world and do something else.

Starting and running my own business that provides me with the lifestyle I want is on the top of that list. So yeah, I guess that’s what’s next.

Short Term Thinking Kills Your Chance At Becoming Rich

Note here how Sterling isn't just taking off immediately on his next adventure now that he's out of debt. He's gotten past living for the present known pleasures.

He's now focused on creating the life he wants, and that takes focusing in on creating the future unknown pleasures.

He's now going after the long-term pleasure of financial freedom.


If anyone wants to reach out to you with questions or for advice, how can they get in touch with you?

Yeah, man. I’m totally happy to talk to anyone if they have questions...

The best place to contact me is via Instagram @sterling.montes.

You know what, man? This whole convo kinda makes me feel less bad about 2017.

I guess I knew how I got there, but after this I’m like, “Oh, yeah.” Because I dropped $1k to go to SouthEast Asia, $1.5k on the stupid truck frame, $4k on the stupid truck, etc. hahah

That adds up pretty quick to stupid money, and that's just not cool.

I guess this gave me some good perspective. I’m stoked for what’s to come.



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Sterling is a freelance growth marketer, and past student of The Hidden Green.


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