Founder Playbook · The Bootstrapped Founder
10 tactics from Nicolas Cole
Nicolas Cole — Harnessing the Written Word for Profit
Watch the full episode“nobody wants to go to the gym but everybody wants the results of going to the gym right nobody wants to eat healthy everyone wants the results of eating healthy and writing is sort of no different a lot of times the process of writing isn't always easy or enjoyable or fun but the outcomes are worth it”
Sell the outcomes of writing, not the writing itself
Stop pitching "write more!" — almost nobody wants to write. They want zero-CAC customer acquisition, category-defining thought leadership, passive income from digital products, status, or money. Each of those outcomes is achievable through writing, and writing happens to be the most scalable / lowest-barrier vehicle (50% of the internet is text). Lead conversations with the outcome the listener actually wants; writing is the means.
“I think about writing actually in the opposite direction I think about it as if I invest time in building a library that's a library I can use over and over and over again... I've started uh reposting a lot of my old long form content on Twitter SLX right now and just this morning I saw someone comment and go how do you have so much time to write so much long form every day and I'm sitting there going you have no idea that I'm posting long form essays that I wrote seven years ago”
Build a reusable writing library — not a daily-content treadmill
Most founders frame content as a treadmill — "if I commit to LinkedIn, I have to post forever." Reframe it as library construction: every piece you publish is an asset you can repost, rewrap, recompile, and re-publish for years. Cole reposts 7-year-old long-form essays as fresh Twitter content and readers can't tell. After 12-18 months of consistent shipping you have a multi-year remix arsenal; new readers see today's content as fresh regardless of when it was written.
“I treat my writing like an athlete and I train every single day and I at the end of every year I'm I'm constant asking myself the question like okay my my right hand is more dominant than my left hand what do I have to do to cross train and I'll I'll put myself through exercises... reading the a page or two of the thesaurus every morning or I'll read books in genres that I have absolutely no real interest in”
Train writing like a pro athlete — daily reps and deliberate cross-training
Most creators write to publish — pure output. Athletes train to compete — deliberate practice across weaknesses. Apply the athletic model: daily writing reps, plus weird targeted drills nobody else does. Read genres you hate to study foreign voice patterns; highlight a single book in three colors (voice / plot / structure) to reverse-engineer construction; read a thesaurus page every morning. The unsexy cross-training is what compounds into a voice nobody else has.
“you could you could say that an even easier place to start writing on a platform like X or LinkedIn or whatever is not you broadcasting but you just replying to other people's exactly yeah right and I yeah I I am a big believer in what is the simplest action Simplicity is velocity”
Start by replying to others, not posting from a blank page
The blank-page trigger paralyzes most beginners. Replace it with the lowest-barrier action: reply on someone else's post. There's already a topic, a context, and an audience watching the thread. You don't have to invent anything — you just have to add one specific thought. After 100-200 high-quality replies on the same handful of accounts, you'll have followers, a voice, and natural compounding into your own posts. Simplicity is velocity.
“if we have to you know use that structure I would clarify the language and call it more something like like reader problem fit like you're not starting with you you're starting with the other person and you're not starting with here's what I want to say you're starting with well what's their problem what's their question”
Optimize for reader-problem-fit, not product-market-fit — write "you content", not "I content"
Reframe writing as reader-problem-fit, not self-expression. Start every piece with the reader's question (not your topic): what does this person actually need to know? Even Harry Potter and David Foster Wallace answer specific questions readers carry into the book. The shift from "here's what I want to say" to "here's what you need" is what unlocks the audience response everyone wants. The product is the reader's outcome; the writing is just the delivery.
“most writing can be reverse engineered back into these four different buckets it's either actionable aspirational analytical or anthropological... what's happening in that moment is your friend loves aspirational books and you hate aspirational books you love actionable books right”
Pick one of the 4A buckets — actionable, aspirational, analytical, or anthropological
Every piece of writing falls into one of four buckets: (1) Actionable — "here's how to do X"; (2) Aspirational — "I was broke, now I'm free, you can be too"; (3) Analytical — "here's what's happening in this trend"; (4) Anthropological — "here's what this group of people is going through." Pick the one you enjoy writing AND the one your target reader prefers consuming. Mismatch creates the "my friend loves this book but I can't get past page one" effect — both writer and reader were valid, the bucket didn't match.
“you as the conduit don't always have to be the source of wisdom or Brilliance one of my favorite examples is Ryan holiday has now dominated this category of stoicism right he invented stoicism right right exactly... his entire career is not based off of his insights it it's based off of Marcus aurelius's insights that he's a conduit for and he makes it very easy and accessible for other people”
Be a conduit, not a source — credibility transfers through curation
You don't need to be original to be valuable as a writer. Ryan Holiday turned Marcus Aurelius into a multi-million-copy stoicism empire. Tony Robbins translated existing financial-literacy ideas into accessible bestsellers. Curated experience counts as credibility — your job is making something already-known easy to access for a specific audience. Pick a body of work nobody in your niche is translating yet and become the conduit, not the source.
“the person who would be your client has a lot of knowledge so they've been in their industry for you know 10 20 30 years they have a significant amount of knowledge but they have a bottleneck called I don't have the time to write... the writer has the complete opposite problem right the writer goes I don't have 30 years of knowledge but I have the time and I have the skill set”
Ghost-writing is symbiotic — clients have time-shaped knowledge problems, writers have writing-shaped time solutions
Ghost-writing is not "writer fakes being the client." It's a two-sided bottleneck trade: the executive / founder has 20-30 years of pattern recognition but no time and no writing skill; the writer has time and writing skill but no decades of pattern recognition. Pair them and both win. The writer accelerates a decade of learning by working alongside the expert; the expert ships the body of work their knowledge deserves. Frame the engagement explicitly as bottleneck-trade, not impersonation.
“productizing yourself as a writer is very difficult in the beginning so the benefit of productizing yourself with with in creating some sort of digital product is that it is quote unquote infinitely scalable... if you're providing writing as a service it's a whole lot easier to find one person who's going to pay you 5 grand a month right rather than find a 100 people who are going to pay you 20 bucks a month”
Service first to $10-20K MRR, then productize — the barbell writing career
Two career paths in writing have opposite shapes. Service (ghost-writing, retainer copy) lets you hit $10-20K MRR fast with a handful of clients but caps near $30-50K before you need an agency. Productized (paid newsletter, books, courses) starts slow because you need volume, but ceiling is unbounded. The fastest stable career: service first to financial security, then reinvest into digital products. Once productized starts working, clients buying the product become new high-ticket service leads — the flywheel goes both ways.
“ship 30 caters to beginners it caters to I've I've really never written on the internet before how do I get started and it has really humbled me and made me realize that making things simple is difficult if you want to explain it to a beginner you can't you have to you have to have a level of clarity of someone who's mastered it in order to really explain it in a way that a beginner can understand”
Writing for beginners is the hardest writing — and the biggest opportunity
Writing for experts is easier than writing for beginners because experts share vocabulary with you. Writing for true beginners forces ruthless clarity — you can't use any unexplained term. That bar is exactly why most experts can't do it: they don't have the meta-clarity yet, even if they have the underlying mastery. Pick your craft and challenge yourself to write a beginner-grade explainer of it. The reps build the highest leverage writing skill — and beginner content has the largest addressable audience.