Cole’s Exact Path To Creating His First Digital Product

Dickie Bush & Nicolas Cole

Ultimate Guide Table of Contents

Ahoy and happy Monday!

Welcome to another week of Start Writing Online—where every week we dive into 1 of the 10 biggest problems all writers face:

  • Distractions
  • Over-editing
  • Perfectionism
  • Procrastination
  • Self-confidence
  • Generating ideas
  • Impostor syndrome
  • Writing consistently
  • Finding time to write
  • Loose feedback loops

(And, of course, if you want to crush all 10 of these AND master the fundamentals of Digital Writing in just 30 days, we'd love to have you in the next cohort of Ship 30 for 30!)

This week, we want to inspire you with an in-depth “behind-the-scenes” example of what it’s like to go from 0 to $1 to your first $5,000.

Cole here, and this is my story about the path I took to create my very first digital product and how I made my first $5,000 online.

Strap in!

Here we go…

Building A Daily Writing Habit

I started writing online in 2007, when I was a junior in high school.

However, I didn’t launch my first digital product until I was 24 years old—a year out of college. (Had I know what a “digital product” was back in high school, even with the novice technologies that existed back then, I probably wouldn’t have even gone to college!) I had just graduated college with a degree in fiction writing, and spent my first 6 months in “the real world” commuting an hour to and from work every single day for minimum wage—only to return home to a shoebox studio apartment with no air conditioning, an air mattress, and a $20 desk from Goodwill. It didn’t take me very long to realize I was on the fast-track to going nowhere, and with 10+ hours of my day consumed by a full-time job, my dream of becoming a writer was quickly slipping through my fingers.

Until finally, I reached a breaking point.

If I didn’t start building momentum in a different direction, I knew this was going to be my life. I was going to work my way up the ladder at this advertising agency. I was going to be kept moderately happy with incremental raises and meaningless title changes. And (doing some napkin math), it was going to take me approximately 87 years to save up enough money to “retire.” (And not retire in a villa on the beach. Retire in a slightly upgraded version of the studio apartment I fell asleep in every night.)

So, enough was enough.

Out of desperation, I challenged myself to write 1 Quora answer every single day for a year straight. I’d been actively reading other writers on the platform and thought, “I have questions I can answer too. I can do this.” But I knew that if I started writing online “when I felt like it,” I was never going to make any progress (playing video games as a teenager had taught me this). So I made a promise to myself: no matter what, I was going to write every single day on Quora. 100 words. 200 words. 800 words. 8,000 words. Didn’t matter. I was going to write something, every single day, for a year.

  • Best case scenario, I’d build an audience and see some success with my writing (I had no idea what “success” looked like, I just figured something good would happen).
  • Worst case scenario, I’d spend a year practicing my craft, doing what I already enjoyed.

And with that, I dove right in.

You can read my very first Quora answer here.

The Breakout Data Point

Like most people (everyone starts at 0!), it took me several months to see any real traction on my digital writing.

My first hundred Quora answers looked a bit like this:


And so on...

But, just like we teach in Ship 30 for 30, I paid close attention to which answers attracted “more views” (relative to everything else I’d written) and which answers attracted less. For example, if everything I wrote was hovering around the 10-20 view range, and something all of a sudden got 40+ views, I would sit there and think about it. That’s 2-3x more readership! So, why did that happen? Was it the topic area? Was it the voice I used to tell the story? Did I tell a story, or did I just answer the question? How did I format it? How long was it? These were all questions I’d ask myself, trying to figure out what readers were interested in versus what they ignored.

And I came to a few conclusions:

  • Self-Improvement: Right away, I realized that every time I wrote in the self-improvement category, I always attracted 2-5x more views. But the reason is very simple: self-improvement is a biggest category on the Internet. So of course, writing in a bigger category = higher average views. Whereas if I would write a Quora answer about blogging (smaller category), I’d get less relative views. (So if “all I cared about was views,” then I should write more self-improvement stuff!)
  • Personal Stories: I also noticed, early on, that whenever I would answer a question with a personal story, that answer almost always attracted comments. Whereas if I would just answer a question literally, no one would comment. Within my first 1-2 months of writing on Quora, I started to make “including some sort of personal story” part of my signature toolkit for writing online.
  • Mentality: Another big early takeaway for me was that nobody cared about my writing when I was trying to give tactical advice. I was very into bodybuilding in my early 20s, and so I would try to write these Quora answers where I'd explain nutrition, fitness tips, lifting routines, etc., and they would always fall flat. Why? Because even though I was an active gym-goer, I lacked the credibility a pro bodybuilder or pro fitness model had. Those writers on Quora were who readers wanted to read—not me. So I had to swallow that and try something different. And what I learned was that people really loved reading about my gym “mentality.” I was very good at articulating the importance of good habits, repetition, mindfulness, self-awareness, consistency, etc., and whenever I would write about those topics, viewership would skyrocket.

The more I doubled-down on the above takeaways, the more views my Quora answers got, the more readers commented, the more followers I attracted, until....

One day, I wrote my most viral Quora answer ever.

And still, almost 10 years later, this is one of my most viral pieces of writing ever on the Internet.

As always, this happened on a day I really debated not writing. I really thought about it. I hadn’t missed a day yet, and I’d been at it for almost 3 months. “Who is going to notice?” I told myself. But I knew it would drive me nuts if I broke my streak. So right before I left the office for the day, I pulled out my laptop, sat down, scrolled through my Quora feed, found a question that grabbed my attention, and wrote 2 quick paragraphs.

Hit publish. Left for the train.

And 45 minutes later, I was on the front page of Reddit.

You can read the viral Quora answer here.

My First Digital Product

That Quora answer went absolutely bonkers.

A million views in 48 hours.

At the top, I had posted a Before/After image of my fitness transformation—on the left, me weighing less than 100 pounds, sick, undiagnosed with Celiac Disease, with a giant “S” curve in my spine, and on the right, me weighing 175 pounds, shredded, in my god damn underwear (something my teenage self would have had an insecure mental breakdown even considering). It was a stark contrast, and the two paragraphs I paired with it must have resonated.

Immediately, my inbox started getting filled with guys who were just like me.

And every single one of them had the same 2 questions:

  • “What is your diet to put on muscle as an ectomorph?”
  • “What is your training routine as an ectomorph?”

If you don’t know, an “ectomorph” is a certain body type, and it basically means your metabolism is like a rampaging garbage truck that eats and eats and eats and still wants more. As a result, it’s very hard to put on weight and muscle because you are constantly in a caloric deficit. You literally can’t give your body enough calories because it’s burning them up faster than you can supply them.

Well, turns out, I wasn’t the only “freakishly skinny kid” on planet earth who had this problem.

I received, hundreds, thousands of emails and direct messages from guys all over the world who said, “That picture of you on the left? That’s me. Please help me.” And all of a sudden I realized I had stumbled upon a niche that was being massively underserved. There was tons of bodybuilding, fitness, and wellness content online, but very little catered specifically to “ectomorphs.” And my Before/After transformation was one giant neon sign of credibility.

“I did it—and you can too.”

So that weekend, over the course of 48 hours, I whipped up 2 eBooks. My very first digital products. I had never done this before, and I also felt very insecure about the fact that I didn’t know how to design or create anything that looked “professional.” But every hour that went by, my inbox filled with more and more guys all asking the same question, and creating 2 eBooks that answered those 2 questions seemed like the most scalable way to give them the answers they were looking for.

I called it: Skinny to Shredded.

And I created a lifting guide, and a nutrition guide.

Each eBook was less than 20 pages and looked like it had been designed by a 3rd grader, but the content inside of it was all that mattered. These were my exact workout routines, and exactly what I ate for breakfast, lunch, 2nd lunch, and dinner. Now, was I a nutritionist? No. Was I a personal trainer? Nope. I just figured: people are emailing me non-stop, and if they want to know, then I’ll tell them.

That Sunday, after I finished creating these 2 eBooks, I bought my first website domain (same one I have today). I picked a template on Squarespace and made an ultra-simple 2-page website. And I uploaded my 2 eBooks for sale. (This was long before there were platforms like Gumroad that made this process exponentially easier.)

And first thing Monday morning, I turned them live for sale.

How I Made My First $5,000 Online

To capitalize on my viral Quora answer (and every other fitness-related answer I’d written to date on Quora), I went back and added a CTA at the bottom that directed readers to my new website and digital products.

The CTA I added to my viral Quora answer was this:

Since I've been getting so many requests about my training routine and diet, I decided to put together an e-book including the 4 routines I've used in my years of training. You can download it here.

Since that Quora answer was still accumulating hundreds of thousands of views, that one CTA essentially drove $5,000 worth of sales in the first week of being online.

I’d priced each eBook at $19.99 and both as a package for $29.99, and I will never forget sitting in our Monday morning meeting at work, my phone buzzing in my pocket from all the Stripe notifications:

  • $19.99
  • $19.99
  • $29.99
  • $19.99
  • $19.99
  • $29.99
  • $19.99
  • $19.99
  • $29.99

This was my Zero to $1 moment—not just because I made my first dollar online, but because I couldn’t see the world the same way anymore. Making my first dollar on the Internet fundamentally changed the way I thought about earning income, and showed me a different path forward in my life and my career.

I was hooked.

I was hooked.

Collecting Dividends

For years after that, I collected dividends on those two products. (I also went on to create a core workouts eBook, specifically for ab workouts, as well as a gluten-free/dairy-free cookbook with some of my favorite recipes.)

Every time I wrote a Quora answer related to health, fitness, or wellness, I would link to one of those eBooks somewhere—within the answer, in the CTA at the end, or in the comments to someone asking me questions. And almost every day, if not a few times per week, my phone would buzz with another Stripe notification. At that time (2014), I was making around $35,000 per year as an entry-level copywriter at an advertising agency, which meant I was taking home around $2,100 each month after taxes. After the initial spike of sales (from my viral Quora answer), these eBooks continued to generate around $250 per month for me—passively, like a dividend.

$250 in the context of $2,100 per month meant I had essentially given myself an 8.4% raise.

And I didn’t even have to ask my boss’s permission!

Mistake #1: Not Doubling-Down Again

In 2015, about a year after the success of these initial digital products and fitness eBooks, I made probably the biggest mistake I could have made (from a financial perspective).

I decided to start all over again in a new category.

It was very, very clear to me that I had stumbled into (and had the opportunity to create) the “Skinny to Shredded” category. I could have been the guy who rallied all the ectomorphs around the world and given them the education, the training, the motivation, and the community to put on a bunch of muscle and “get shredded” just like me. But, to be honest, I didn’t want to be that guy. I was already starting to reach a point where I was getting bored in the gym. I’d been living like a hardcore bodybuilder for 5 years, eating 6 meals per day, spending 2-3 hours per day in the gym, taking 10 different supplements (never steroids!), and repeating the same dozen exercises over and over and over again. I loved lifting, but I knew deep down it wasn’t going to be my career. I didn’t want to compete. I didn’t want to become a fitness model. I didn’t have the genetics (or the desire) to put on another 100 pounds of muscle and become an actual bodybuilder. And I didn’t want to become a personal trainer. I was very aware that I had stumbled into some initial success, but had to make a choice: either I was going to make this my life, or I wasn’t.

And I came to the conclusion I didn’t want to be “the ectomorph bodybuilder.”

I wanted to be a writer.

Now, this decision wasn’t really a mistake (things clearly turned out OK). But I say it’s a mistake because, looking back, I think there was a middle ground. I think I had discovered an untapped niche, and I could have very easily dominated that niche for a few years, helped a lot of people, and monetized it really, really well. In fact, not long after, another guy basically did just that. His name was Greg O’Gallagher and he was basically an ectomorph who decided to cater to other ectomorphs—and built nearly a $10 million business running YouTube ads and selling people a very similar digital product to the same one I’d created by writing on Quora.


Pivoting Into A New Category

Instead of doubling-down on fitness-related content, I decided I wanted to pivot in a new direction.

I had started writing on Quora because I wanted to build an audience for my forthcoming book—a memoir I’d been working on about my years as a pro gamer in high school, called Confessions of a Teenage Gamer. I wanted to be a writer, so I figured I’d better start making a more conscious effort to work in that direction (this was after nearly a year of writing on Quora AND creating/selling my first digital product in a completely unrelated category! Remember: it’s not a marriage decision.). But now I knew how the game worked: write on Quora, gather data/feedback, double-down on what works, expand “what works” into digital products, repeat.

So, I started writing in new topic areas.


  • Gaming (to build an audience for my memoir).
  • Writing advice (because I wanted to attract people interested in writing)
  • Entrepreneurship (because my boss was a serial entrepreneur, I was learning a lot from him, and was already starting to think, “Maybe one day I’ll quit my job and start my own business of some kind as well)

And, as you can probably imagine, those first few months were a transition.

As soon as I stopped writing about being an “ectomorph” and catering to that niche that had just gone viral, I started losing followers. Lots of them. And when I would write about other topics like gaming, writing, or entrepreneurship & business, people would STILL comment, “Where can I find your fitness content?” It was a frustrating few months because I felt like I had just spent a year building an audience, and now my audience was yelling at me saying: “WE DON’T LIKE THIS NEW DIRECTION.”

But if you want to pivot, that’s what happens.

I lost a bunch of followers. My viewership tanked.

And then slowly but surely, I swapped out all the people who followed me for fitness advice for new and different readers who followed me for digital writing advice.

My 2nd Digital Product

Halfway through 2015, Quora released their list of Top Writers for the previous year.

If you don’t know, Quora used to have this incredible program where their team would select a few hundred writers on the platform and acknowledge their contributions by giving them Top Writer badges. These badges unlocked an invitation to a meetup in New York City where you could meet other Top Writers on Quora—and if you went, you also received a Patagonia jacket with “Quora Top Writer” stitched on the front.

Well, when their list came out, I was named as one of Quora’s Top Writers in 2014. Out of 200 million users, I was one of a few hundred (less than 0.01%) on that list—alongside some pretty incredible writers, thinkers, and industry experts. When I told my boss (who had become a close mentor to me) at work that I’d gotten invited to this meetup in New York, he insisted I go. And when I told him I couldn’t afford it (cough cough because I was still being paid like an intern) he took it upon himself to take me. He bought the flights, the hotel, and that December he took me to the meetup. It was a life-changing experience.

That meet-up (with maybe 100 Quora writers) showed me how much progress I’d made in just 2 years of writing online. When I walked in, people recognized my face and name from a bunch of my viral Quora answers. And I even had other Top Writers come up to me and say how much they loved reading my writing. It was truly the first time I realized I’d started down a different path, and that I was “on my way” to becoming a writer. (This meet-up was also where someone from Quora pulled me aside and told me that in 2014, I was the fastest user to go from creating a new account to becoming a Top Writer, and in 2015 I was the #1 most-read writer on the entire website.)

All of this gave me the idea for my 2nd digital product.

A mini-course teaching people how to become a top writer on Quora.

I came back from New York and right before I went home for Christmas, end of 2015, I holed up at the office for an entire weekend and outlined this mini-course. I made my own slides (again, looking like it had been designed by a 3rd grader). I wrote out a script for each of the modules. And then from 8am to about 10pm that Sunday, I practiced, I recorded the videos, and I uploaded them to Teachable.

I priced the mini-course at $27, and added a link to it in my Quora profile.

You can still find my old Quora Top Writer mini-course live on the Internet here.

Mistake #2: Not Actively Selling The Course

Since my first digital product (Skinny to Shredded) had started selling copies right away, I sort of assumed that once you created something new, people would just buy it.


I was still very much transitioning out of fitness and into this new category for myself as a digital writer, and so even though I had my mini-course linked in my Quora bio, and I would occasionally mention it in writing-related Quora answers, nobody really bought it. I made a few hundred dollars right when it launched (a far cry from $5,000), and then after that, sales went dead.

And so I just sort of gave up.

This was a giant mistake.

Here’s what I should have done:

  • Write more Quora answers specifically about writing on Quora. I had a ton of credibility here being a Top Writer AND knowing in 2015 I was literally the most-read writer on all of Quora. What I should have done was dominate the Quora ecosystem and write obsessively about writing on Quora. Instead, I wrote about writing online “broadly,” and a lot of times people would comment on my answers asking me about blogging, or writing on other platforms—which made my “How To Become A Top Writer On Quora” course seem irrelevant.
  • Create a free opt-in and start building an email list. I didn’t have the digital marketing knowledge back then that I do today, but what I should have done was take the first 1-2 modules from the video course and give them away for free on a separate landing page—and start collecting people’s emails. If I wanted to build an audience of digital writers, and one day monetize that audience, then I should have started gathering their contact info and educating them on why they should consider writing on Quora as well.
  • Made my course more expensive. I started $27 for that mini-course, when the truth is I could have easily charged double or triple that. I priced it so low because I thought, “Well, the cheaper it is, the more people will buy it!” Wrong. This is a huge myth in digital entrepreneurship. In fact, it usually sends the opposite signal: “Why is this so cheap? It must be worthless.” I should have made it a $99 course, at least, and spent more time educating people on why it was worth $99.

Since I didn’t do these things, I came to the (false) conclusion that maybe I’d just gotten lucky, and that digital products were harder than I thought. I had been trying to teach myself about digital marketing funnels, but every time I started going down that rabbit hole, I just felt like there was something I wasn’t “getting.” In reality, I was making it much harder than it needed to be.

My Top Writer mini-course would have sold just fine had I put even a little bit of attention behind it, wrote about it more often, drove people to it, gathered testimonials from the people who took it, and then used those testimonials to encourage others to take it too.

Instead, I did none of those things.


Scaling Outside Of Digital Products

At the beginning of 2016, I decided I was going to start tracking all the income I was generating outside of my full-time job.


  1. I now had multiple digital products: my Skinny to Shredded eBooks were still up for sale on my website (even though I was trying to pivot out of fitness), and I now had this Quora Top Writer mini-course.
  2. I wanted to quit my job: I knew that in order to have the confidence to quit my job sometime that year and go all-in on being a writer, I would need visibility into how much money I was actually generating outside of my 9-5.

So, I created a spreadsheet to document all my different income sources (I still use this exact same template today, years later):

At the start of 2016, I had 3 buckets of revenue: my eBooks being sold on my website, my Quora Top Writer mini-course sales via Teachable, and the $1.87 per month I was making as an Amazon Affiliate. (Hey, every penny counts!)

But looking at the above screenshot, you can see how in May, 2016, something changed.

I started writing for Inc Magazine as a columnist—where I got paid per page view (which meant, if I wanted to make any real money, I needed to write A LOT and hope something went viral).

Between May and September, I started consistently generating about $1,000 per month from Inc. In addition, I’d learned that a lot of writers were using their own Amazon Affiliate codes and linking to books/products inside their Incarticles to collect extra revenue. This was really my 3rd “digital product,” where I was effectively monetizing other people’s products by acting as the affiliate driving attention to them. For example, some of my most popular Inccolumns were book lists—and when I would link to the books on Amazon, I’d use my affiliate code and collect a small piece of the transaction. You can see my Amazon Affiliate revenue started to make me an extra $50-$100 per month, on average, on top of my Inc revenue being around $1,000 per month, give or take.

Plus my eBook sales, plus the occasional Quora Top Writer sale, and by August/September of 2016, I could objectively see that I was generating about 50% of my full-time income by writing online.

Even if it was a bunch of unrelated revenue streams Duct-taped together.

End of September, 2016, is when I quit my job.

At the same time, I had my first big viral hit on Inc—earning me almost $5,000 in a single month.

AND, that same month, is when I landed my first ghostwriting client.

By the end of 2016 (last row), I was making $20,000 per month as a ghostwriter (plus my other revenue sources). And in those final 3 months of the year, I’d essentially earned more than the entire 9 months prior.

Scaling Services

If I could do it all over again, I wish I would have kept trying to create digital products.

Instead, after “taking the leap” and quitting my job, I dove head-first into the world of ghostwriting. It was a lot of fun, paid very well, and allowed me to meet a ton of fascinating people. However, it was a LOT of work. 2017-2020, I was ghostwriting for anywhere from 7-12 hours per day, 7 days per week. I never took vacations—and whenever I would travel with my girlfriend, or friends, I would inevitably have to escape for a few hours to ghostwriting a handful of pieces. And when one of my closest friends and I decided to scale my talent for ghostwriting into a business, called Digital Press, things only got more demanding, complicated, and stressful. At our height, we employed 20 full-time writers, editors, and salespeople, had 80 clients, and were doing $2 million in yearly revenue. Meanwhile, my co-founder and I were taking modest salaries (we had employees making as much as we were), with the business barely banking any profit.

It was a terrific learning experience, but not a very fruitful or profit-filled one.

After 3 years of building that business, I walked away with about $10,000 in savings.


My 4th Digital Product: The Art & Business of Online Writing

In 2020, a little less than a year after my co-founder and I decided to fire everyone from the business and scale the agency back to just us two again, I wanted to write a book:

The Art & Business of Online Writing.

I had learned A LOT about digital writing—from years spent writing on Quora, to writing 400+ columns for Inc Magazine, to ghostwriting for 300+ CEOs, founders, Silicon Valley investors, Grammy-winning musicians, professional athletes, New York Times best-selling authors, and more. And I wanted to put it all together in a book that I could give to any and every writer emailing me the same handful of questions:

  • “Where should I be writing online?”
  • “How do I go viral?”
  • “What topics are most popular?”
  • “How do I write better headlines?”
  • “How can I start contributing to major publications like Inc, Forbes, Business Insider, etc.?”

The more I wrote online about writing online, the more these same handful of questions kept popping up in my inbox. So, burned out from spending 3 years building a service company, I decided to go back to what had originally worked so well for me: take the questions people were asking, and answer them. That’s how I made my first $5,000 online (with my Skinny to Shredded eBook series), and I figured, if I kept trying that path again and again, something would hit.

Well, I was right.

The Art & Business of Online Writing became an instant hit. I made over $5,000 my first month of publishing in sales. But then, learning from my mistakes (particularly with my Quora Top Writer mini-course), I didn’t just sit back and “wait for people to buy.” In 2020, sitting at home during the pandemic, I went all-in on writing online about digital writing. I wrote that book, and then I started writing Quora answers again, Medium articles, and Twitter Threads constantly. And in everything I wrote, I would link to the book. Over and over again.

After a few months of that, I started an email list.

And then at the end of 2020 I met Dickie (he’d heard about my book), and by January 2021 we were working together on building Ship 30 for 30.

And here we are today!


The reason I wanted to write all of this out is so that you can see, step by step, how the process works.

I was once at Level 0, just like you.

I had all the same fears, just like you.

I didn’t know what was going to work, just like you.

But I kept trying things, kept listening to the data, kept listening to myself, and kept moving forward. I am a 10 year success story. And I had to go through a lot of chapters where “nothing seemed to be working” in order to get to here.

I know it can be hard to trust the journey, so that’s why I want to share mine. So you can see how each step slowly, weirdly, leads to the next one.

And if you stick with it long enough, one day, you’ll pick your head up and realize how far you’ve come.

That's it for today!

Chat next week!

–Dickie Bush & Nicolas Cole

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