My Origin Story, Part 2: The Hardest Year of My Life

₱150,000 and a dream

I quit my job in 2013 with ₱150,000 ($3,000) in savings and the absolute conviction that I'd triple my income in three months. I had read the books. I had seen the blogs. Other people were doing it. There was no reason I couldn't too.

The first thing I did was get a list of 100 dentists in Alabama.

Why dentists? I read that dentists make good money and have a chip on their shoulder about not being respected as much as doctors. Why Alabama? It's the first U.S. state alphabetically. That was the full extent of my market research.

I used an online direct mail service to send them physical letters. Real paper, real stamps, and real mailboxes in Alabama.

Nobody wrote back. It's fine, I told myself.

I also started a productized travel booking service, Location Asia. It was basically me acting as a glorified assistant booking flights and hotels for American digital nomads living in Thailand and Vietnam.

None of it worked.

Meanwhile, I was writing SEO articles for $5 each. The first money I ever made online was $30. It took me a whole week. The articles were about how to clean a specific type of window I had never seen in my life.

I was supposed to be tripling my income.

The Debt

I didn't know anything about business and marketing and sales and copywriting... That was the problem. I needed to learn so many things! So I took courses: IWTYTBR, AWAI… They cost $1,000 to $3,000 each. I read tons of books, from How to Win Friends and Influence People to Think and Grow Rich.

I spent my $3,000 savings very quickly.

Then I put the courses on my credit card.

Then I borrowed money from my mom.

I was spending money I didn't have to learn skills I wasn't using because I was too scared to use them before I felt ready. 

When was I ever going to feel ready?

Zig Ziglar

One afternoon, I was sitting in Serenitea — a milk tea place in Banawe in Manila — reading See You at the Top by Zig Ziglar.

It was 3pm. I was supposed to be working. I wasn't sure what working even meant anymore. All I knew was that I needed to make money, but I had no idea what I should be doing to make it happen. So I was reading a book about how to stay motivated, set goals, and be disciplined.

I remember thinking:

If I could just find the right book, it would tell me what to do. If I could just fix the procrastination, everything else would follow.

James Chartrand

In the meantime, I also wanted to get better at writing but writing was so hard. There was no Claude in 2013. Just me, a blank page, and resistance.

James Chartrand ran a popular blog called Men with Pens. It was one of the best blogs on writing and freelancing at the time, one of the blogs I read obsessively.

They had a course. It cost $1,500. I really didn't want to spend any more money.

But then they opened up a scholarship.

I almost didn't apply. They had a huge audience. What were the odds of me winning?

Then I remembered something Tim Ferriss wrote:

Most people overestimate the competition that nobody even showed up.

So I wrote my entry. It’s the first ever blog post in my blog.

I won.

The course taught me how to write. I learned to separate outlining from drafting from editing. I learned to prep the page. For the first time, writing felt like something I could actually do.

But the best thing that came out of it had nothing to do with writing.

In the course forum, I met a financial advisor. For dentists!

Can you believe it??

He had seen all my dentist content. He was also struggling with procrastination; that's why he joined the course. We got on a call. I pitched him a 5-email sales sequence for $1,000.

He said yes.

That was the first real money I ever made online. 

Not from the dentists in Alabama… From a guy who advises them.

Sebastian Marshall

Around the same time, I sent what is possibly the most cringe email of my life.

Sebastian Marshall was (and still is) one of my favorite writers. He tweeted asking what interested people. I found his email and replied to him there.

Here’s the email I sent: 

He wrote back!

Wow Chiara, thanks. By the way, if I can ask — how did you get so ambitious and driven?

He said let's get on a call. I almost didn't do it. I was terrified of the phone. Also, we only had dial-up internet at home, which was too slow for Skype. So I went to a Coffee Bean & Tea Leaf, found a corner, and got on the call anyway. It was noisy, I was nervous, but we did it.

We ended up working together. I helped with his nonprofit GiveGetWin for free. In return, he helped me with my consulting business. He taught me everything: how to do outreach, how to write emails, how to respond to introductions, how to make double opt-in introductions. He recommended books. He pushed me to do stuff in 1 hour when I thought they should take 1 week!

Then he asked me to do my first ever sales call. And record it.

Here’s the recording.

The call lasted almost 5 minutes. But – and I only knew this because Sebastian told me – I lost her within 20 seconds.

I had also asked Sebastian what questions prospects might ask so I could prepare answers. I felt so diligent, like the prepared student I am. He said:

No, no, no you're thinking about this all wrong. You should be the one asking the questions. Lead the conversation.

I have run every sales call, and every job interview, that way ever since.

Kevin Dewalt

By this point I was so sick of myself.

Sick of reading. Sick of courses. Sick of knowing what I should do and not doing it. Sick of the procrastination dressed up as preparation.

So I did something stupid. 

Or audacious. 

Probably both.

I had heard about Kevin Dewalt through Jeremi Joslin, a French entrepreneur traveling through Manila. Kevin was pioneering this idea of Helpful Marketing, the idea that the best marketing is just being genuinely helpful to people. I loved it so much I wrote about it on my blog.

Kevin was also running a company called SoHelpful, and I wanted in.

I had just seen a new book about “digital analytics”. I hadn't read it (hadn’t even bought it). I basically copied the description from the back cover, pasted it into an email to Kevin, and essentially said: Your business needs this, I'll do it for you, will you hire me?

He saw right through it.

But he read my blog posts. And he said:

Wow Chiara, your writing is so compelling.

He hired me to do marketing for SoHelpful.

And then I lived happily ever after

Just like that, I was in. My first tech startup job. Remote, location independent, in 2013.

I had set out to become a digital nomad with $3,000 and a plan to triple my income in three months. It took a lot longer than three months. It cost me more than $3,000.

But I got there.

I was no longer going to be poor. I was working for an American tech startup from wherever I wanted. I didn't even know tech startups were a thing in 2013.

That year taught me something I have never forgotten.

I had spent most of it trying to read my way to ready. Courses, books, Zig Ziglar in a milk tea shop at 3pm… I kept hoping that the right information would make it easier. That one day I would wake up and the fear of reaching out, the fear of the phone, the fear of being told no… It would just be gone.

It was never going to be gone.

The only thing that made it easier was doing it. Sending the emails anyway. Getting on the call even when the internet was too slow and the café was too noisy. Pitching Kevin with a blurb I copied from a book I hadn't read.

That year, I learned you don't read your way out of fear. 

You rep your way out.

Not because you get braver, but because you do it enough times that no single attempt feels fatal.

That was the real lesson of 2013. And it's the lesson I now build my program around.

The job lasted for 16 months.

Then I got fired.

But that's the next post.

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This is Part 2 of my origin story. Part 1 is here. It starts with a spreadsheet, a client meeting in Little Rock, and the day I learned that doing the work and getting credit for it are two completely different games.