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Deep Dive with Ali Abdaal

How Writing Online Will Make You A Millionaire - Nathan Barry

When investing, your capital is at risk and you may get back less than invested. Past performance doesn’t guarantee future results.

Ali AbdaalhostNathan Barryguest

Dec 14, 20232h 38mWatch on YouTube

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CHAPTERS

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Chapter summaries

Growing Up Without Money and Learning That Making Money Is a Skill
Nathan describes a childhood marked by money struggles and how Jason Fried's idea that making money is a skill changed his outlook. He compares business to learning piano, made up of many small learnable skills like sales, pricing and design.
- •Nathan grew up in a family with little money and watched money stress shape his childhood
- •Jason Fried's point that making money is a skill reframed it as something to practice
- •Business is a thousand small skills, like music theory and timing
- •Skills such as landing pages look natural to experts only because they have rehearsed them for years
- •Design polish and packaging affect how content is perceived
Job vs. Business and Refusing the Slow Pace
Ali asks why Nathan chose a business over a job, and Nathan explains that job earnings are tied to time. He tells how he protected his speed at a startup by finishing his work in three hours a day and using the rest to learn iOS app building.
- •In a job, earnings are closely tied to time, and Nathan wanted to earn millions
- •Speed at Wendy's and in per-project web design showed him how efficiency can benefit you
- •At the startup he felt his focus slipping and decided to do his job in three hours a day
- •He spent the rest of the day learning iOS design and coding, building apps that were earning when he left
You Set the Pace: Fixed Work vs. Fixed Time
Nathan traces his 'you set the pace' mindset to homeschooling, where he finished high school early. Ali connects it to fixed work versus fixed time in jobs and school, and both discuss using spare time on side projects.
- •Nathan's mom taught him school was a fixed amount of work, not fixed time
- •He finished the high school curriculum between ages 13 and 15
- •Derek Sivers describes classes moving at the pace of the slowest student
- •Ali says most jobs and school feel like fixed time but are really fixed work
- •Nathan used the overlap between his job and side learning to build skills
Is a Side Hustle Necessary? Skills as Lifelong Assets
Ali says a day job can be a fine path to happiness, while people who feel stifled might consider a side business. Nathan adds that side income stacks on top of existing pay and that skills learned last for life.
- •Ali says the goal is happiness, contentment and meaning, not a big business
- •Some of Ali's team members are happy without side hustles
- •Side income is extra money on top of existing earnings
- •Large companies often have someone else covering every adjacent skill
- •Nathan sees new skills, like his current pilot lessons, as gifts that last decades
Setting Goals Around Who You Must Become
Ali raises building a productivity app and the trade-off of effort versus learning. Nathan says he sets goals by asking what he will learn and who he must become, and Ali shares a journaling prompt about what he would do even if he knew he would fail.
- •Nathan frames goals around skills required, such as hiring and understanding users
- •If the required future self isn't appealing, pick a different goal
- •Ali asks what he'd do even if he knew he'd fail, and the app wasn't on that list
- •Nathan says to fall in love with the process rather than the destination
- •He journals past hard problems to see how much he has grown
From Day Job to iOS Apps
Nathan describes building One Voice, an iPad app for non-verbal children, and learning to code by building specific projects. By 2011 he was making about $3,000 a month from three apps and quit to freelance as an iOS designer.
- •One Voice was an iPad alternative to expensive $7,000 communication devices
- •He learned to code by building and getting help from developer coworkers
- •He built a habit tracker called Commit and a flashcard app
- •Three apps earned about $3,000 a month when he quit his job in 2011
Getting Into eBooks and the 1000-Words-a-Day Habit
Inspired by Chris Guillebeau, Nathan self-published an app design book, sold $12,000 on day one, and stopped taking design clients. His habit app's streak led to writing 1000 words a day, and he reached 600 days in a row.
- •Chris Guillebeau's free eBooks and self-publishing path inspired him
- •The first book launched to a 798-person waitlist and made $12,000 on day one
- •Email proved the main sales driver
- •A second book made $26,000 on its first day
- •The habit produced 600,000 words and three books in seven months
How the Daily Writing Practice Works
Nathan describes using Scrivener with outlines and placeholder pages, counting all writing toward the quota, and talking ideas into voice memos. Teaching everything you know follows, with the idea that people are seen as experts because they teach.
- •Scrivener's word tracking and outline folders let him write sporadically
- •Marketing copy and editing counted toward the daily goal
- •Voice memos and writing like you talk help beat writer's block
- •He wrote flagship essays to unpack ideas he intuitively knew
- •The Authority premise is that people seem like experts because they teach
Working in Public and Writing for the Right Audience
Nathan explains working in public, from his launch post to the Web App Challenge for ConvertKit. Ali worries niche writing gets less reach than a broad video, and Nathan answers with funnel thinking and documenting your knowledge.
- •Writing about how a launch went is easier than doing it and attracts new audiences
- •The Web App Challenge blogged ConvertKit's early journey weekly
- •Nick Huber's funnel mixes broad top-of-funnel and niche bottom-of-funnel content
- •Writing documents processes like team retreat playbooks so knowledge isn't tied to your time
Simple, Not Easy: Practical Tips for a Writing Streak
Ali feels overscheduled and Nathan says simple is not easy, so the habit must be a non-negotiable priority. He then gives tips on running out of ideas, publishing cadence, managing several book ideas and making up missed days.
- •Ali describes overscheduling and commercial incentives squeezing out writing time
- •Nathan says a simple habit still needs the day designed around it
- •He suggests switching up what you consume and using consistent prompts like 'play chess instead of checkers'
- •He recommends picking a publishing frequency, such as weekly, and sticking with it
- •He made up missed days by writing double, aiming for 600,000 words rather than a literal daily count
Personal Blogs and the Secret Money Newsletter
They discuss whether to keep a personal blog alongside a business site, with Nathan favoring flagship guides and raw personal writing. He describes segmenting his audience with a paid email course called the Secret Money Newsletter.
- •Nathan separates ConvertKit's content from nathanbarry.com
- •He advises flagship guides over ghostwritten one-off ranking posts
- •Both want personal blogs that feel like a place to get lost in
- •He created a $100 one-time email course for people making over $200,000 a year
- •The course lets him write without caveats and builds community through reader replies
Sharing Wealth, Fame and Transparency Online
They debate how much income and lifestyle to share, including the risk of being unrelatable and Ali's grandmother's concerns. They compare recognition across creators like James Clear, Mark Manson and Casey Neistat.
- •Nathan says you don't owe creators' ongoing content to anyone
- •Sharing a plane or house can draw attention but changes how you're perceived
- •Seeing people like yourself succeed makes success feel possible
- •Authors like James Clear and Mark Manson get less face recognition than YouTubers
- •Ali enjoys being recognized a few times a day because his content is educational
The Ladders of Wealth Creation
Nathan walks through four ladders: time for money, services, productized services and products. Each ladder requires different skills and offers more leverage, and Ali maps them onto his own career.
- •Time-for-money skills include reliability and following a process
- •Charging by the project separates time from money and introduces leverage
- •Productized services standardize delivery and sales, as with Hey Friends
- •Products range from eBooks to software, marketplaces and social networks
- •Trying to jump straight to the top ladder means learning too many skills at once
2:11:16 – 2:22:54
The Billion-Dollar Creator
Nathan explains pointing an audience at the highest-ROI target, using examples like Primal Kitchen, Glossier and Ryan Reynolds. He and Ali discuss easing into equity businesses rather than leaping, and what he learned from his agency Paperboy.
- •Mark Sisson's blog audience seeded Primal Kitchen, sold to Kraft for $150 million
- •Emily Weiss's blog led to Glossier
- •Jumping several ladders at once is a sure way to fail
- •Building skills step by step, like managing teams, prepares you for bigger bets
- •Paperboy showed Nathan a business that needs little of his time
Creator Flywheels and Final Advice
Nathan explains flywheels using a hand-pump in Lesotho, defining three laws and giving examples like a reply-driven content idea loop and Sahil Bloom's sponsorship-funded growth. They discuss designing flywheels and Nathan advises creating every day.
- •A flywheel flows into itself, gets easier each rotation and produces more
- •A newsletter reply-collecting loop generates content ideas automatically
- •Sahil Bloom reinvests sponsorship revenue into paid subscriber acquisition
- •Nathan maps flywheels in Figma and tests constraints to find other ways to close the loop
- •His final advice is to create every day, with strategy downstream

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