Starter Story

He Quit His Job And Makes $10M/Year Writing Online | Starter Story

21 min
•Oct 2, 20257 months ago
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Summary

Dickie Bush shares how he built a $10M writing business while working full-time on Wall Street, starting with a viral tweet and $5,000 first client. He details his portfolio of four writing-focused businesses and reveals the exact systems, mindset shifts, and daily routines that enabled him to scale from side hustle to seven-figure income.

Insights
  • Ghostwriting and borrowing existing audiences is the fastest path to monetization for writers, generating $5-10K/month without requiring large personal followings
  • Consistent daily publishing (30-day challenges) combined with strategic timing can generate viral moments that unlock business opportunities
  • The skill of persuasive writing is universally applicable across all business models and industries, making it a foundational income-generating skill
  • Operating from abundance (having stable income first) enables better decision-making and allows pursuit of passion projects without desperation-driven choices
  • Eliminating perfectionism and shipping imperfect work is more valuable than optimizing systems, tools, and processes before starting
Trends
Writing-as-a-service business models scaling to multi-million dollar revenues with minimal overheadCreator economy shift from audience-building to direct monetization through premium services and coursesAI writing tools becoming integrated into creator workflows and business offeringsPortfolio approach to online business where multiple revenue streams (courses, coaching, SaaS, newsletters) reinforce each otherSide hustle to full-time transition only after reaching $1M annual income thresholdEmphasis on skill-building over tool optimization in creator educationCommunity-powered learning models (cohort-based courses) outperforming traditional self-paced offeringsWall Street talent migration to creator economy and online businessPersonal brand monetization through multiple product tiers (free content, paid courses, premium coaching, SaaS)
Topics
Online writing monetization strategiesGhostwriting business modelsCohort-based course designPersonal brand building on Twitter/social mediaSide hustle to full-time transitionWriting skill developmentContent creation systems and routinesAI writing tools integrationSaaS product development for creatorsNewsletter strategy and growthPersuasive copywriting techniquesAudience building vs. direct monetizationProductivity and time managementEntrepreneurial mindset and risk managementCreator economy business models
Companies
BlackRock
Dickie's former employer where he worked as a hedge fund trader before transitioning to full-time writing business
Ship 30 for 30
Dickie's community-powered writing course for beginners, generating approximately $3M annually
Premium Ghost Writing Academy
Dickie's group coaching program for freelance writers, generating approximately $5M annually
Write with AI
Dickie's paid newsletter training users on AI writing tools, on pace for $500K annual revenue
Type Share
Dickie's SaaS platform providing templates, analytics, and hosting for online writers
Princeton University
Dickie's alma mater where he studied math and computer science and played college football
People
Dickie Bush
Founder of $10M writing business portfolio, former Wall Street trader, primary subject of the episode
Pat Walls
Host of Starter Story podcast, interviewer conducting the conversation with Dickie Bush
Nicholas Cole
Business partner in Ship 30 for 30, co-author of 'The Art and Business of Online Writing'
Naval Ravikant
High-profile figure whose retweet of Dickie's Day 27 post triggered viral growth and audience expansion
Quotes
"If I wanted to work harder, if I wanted to bring more intensity, nothing would happen. And that was a freak out moment where I said, time to go find something I could do that with."
Dickie Bush•Early career realization at BlackRock
"You never know what's going to go viral, you never know what's going to work, you just have to keep showing up and hitting publish."
Dickie Bush•After Day 27 viral tweet
"The fastest way to monetize is actually build the skill yourself and then borrow someone else's audience and go straight for them."
Dickie Bush•Monetization strategy discussion
"When you recognize that the foundation for every single piece of content, every product, every video, every podcast is writing. It's the most applicable skill."
Dickie Bush•On writing importance
"There's never a perfect time to start anything. If you can't get started on something today thinking there'll be a better time in the future, that's never going to come."
Dickie Bush•Final advice segment
Full Transcript
This guy built a $10 million business thanks to one simple skill. Writing. What's even crazier is that he started this business while he had a 9-5 job and didn't quit that job until he was making a million dollars a year. He invited us into his studio in Miami, Florida to tell us exactly how he made his first dollar and his exact routine to build a million dollar business while he had a full-time job. They kept it for 30 a.m. right for two hours. Get back to my desk at 7 a.m. Do my black rock work during the day. Log off as soon as I could and then build in the evenings. Before the success, Dickie was crushing it by all accounts. New York City, Wall Street, 6-figure job, but deep down, he was unhappy, slaving away at a job that gave him no freedom. Then, one day, he wrote a tweet that changed his life forever. That was how I earned my first $5,000. I didn't have 20,000, 100,000 quarter-fellows at the time. In this video, Dickie shares his exact blueprints on how to master the $10 million skill of online writing, how to scale your writing business to $800,000 a month, and the best way to get to $10,000 a month as a beginner. The fastest way to monetize is actually... I'm Pat Walls, and this is Starter Story. Thanks for having me, Dickie. Pat, what's going on, man? I'm in the shipyard. Appreciate you being here. Tell me about who you are and what you built. I'm Dickie Bush. Two years ago, I was a Wall Street hedge fund trader working 60-hour weeks under fluorescent lights trying to make $90,000 a year. That led me to start writing online. Now, two or three years later, I am a full-time writer with a portfolio of writing based businesses on pace to do $10 million in 2024. Break down all the businesses that you run. It's a portfolio right now of four businesses. The first is Ship 30 for 30, which is a community-powered writing course that helps beginners who've never written anything start writing online. That one does about $3 million per year. The second is the Premium Ghost Writing Academy, which helps beginner freelance writers to position themselves as premium ghost writers. That's a group evergreen group coaching model. That one does about $5 million a year. Then we have Write with AI, which is a paid newsletter for training AI writing tools to become your personal writing intern. That one's on pace to do $500,000 this year. And then the last one is Type Share, which is a SaaS business with everything you need to start writing online, templates, analytics, hosting, all of that in one place. So all four of those, they're in the writing area. They all kind of build on one another. And three years ago, I didn't know how any of this worked. Tell me a little bit about your backstory and how do you get into entrepreneurship? So my backstory, you could trace back to when I was pretty young. I had a handful of obsessions. Luckily, hit an athletic streak, which allowed me to play football in college at Princeton. Studied math and computer science there. And then as a sophomore, I got an internship at BlackRock. I was like, wow, this is the coolest thing ever. This is a dream job. I'm going to go work for a hedge fund. That led to taking that full-time job when I graduated. I was checking every single box. I got good grades, on track to be 22 years old, making $180,000 in New York City. I'm like, I did everything right. Amazing. 18 months later, I was doing well at the job. But if I showed up at 5 a.m. and worked till 8 p.m., I might make 10% more money. But if I worked as little as possible, I would make the same amount. And that kind of messed with me because I couldn't apply the level of effort that I wanted to because my incentives weren't there. If I wanted to work harder, if I wanted to bring more intensity, nothing would happen. And that was a freak out moment where I said, time to go find something I could do that with. So you're working your dream job on Wall Street, making good money. What was your turning point that got you into writing online? I witnessed someone I worked with ask for permission to go to their son's Little League game. And he was probably 37, 38 years old. And his boss said no. So if I do everything right for 14 more years, I might be sitting here having to ask for permission to go to my kids' Little League game. Uh-oh. I got to get out of here. I didn't quit right away, which I think is a big mistake a lot of people do because then I would have been operating from a place of scarcity the entire time. Instead, I said, how can I look for ways to passively pursue new opportunities? I started a newsletter inside BlackRock as a way to get my name out there more. After three or four months of doing that, I said, why am I capping myself with people working in this company when I could use social media and the internet, do the same thing and unlock millions of new eyeballs? And that is what led me to starting my newsletter in January of 2020, which was kind of my gateway into writing online. Dickie is the perfect example of someone who was able to turn a simple idea into a million-dollar side project while still working a 9-to-5 job. But that's because he was working on the right idea and had a solid blueprint on what to execute on every day. And that's why I built Starter Story, a library where you can access over 4,000 business ideas, breakdowns and blueprints that real entrepreneurs use to turn a simple idea into a million-dollar online business. That way, you can study and get inspired by what's already working instead of trying to reinvent the wheel. So if you're serious about building a profitable side project and you're still working a 9-to-5 job, then head to the first link in the description and we're going to give you a free breakdown of 160 solopreneur business ideas to help you get started on your journey. Much love and hope you guys enjoy the rest of the video. Alright, so tell me about the early days of writing online, getting your start. So I'm still working on Wall Street, but realized, okay, a lot of the work that I was doing on a daily basis was kind of made up. I went from working 12-hour days down to 3 or 4 and spent the rest of the 10-hour workday learning, reading, immersing myself into different things, and then writing in my newsletter, hey, here's what I read this week, here's what I wrote, here's what I listened to, here's what I'm thinking about following everything that I thought was right, but I had something like 250 subscribers. And so I committed to a 30-day personal writing challenge where I'm going to write and publish something every day for 30 days, and at the end of this challenge, if it doesn't work, I'm going to go out and find something else. Day 27, I hit publish, zero likes, zero comments, zero retweets. I went to bed, thought, okay, cool, this is almost over, like what am I going to do? And at the time I was working on a different side project, which was SAS, that's the better business model, whatever. I went to bed, woke up, that post got retweeted by Naval, apology, a handful of other kind of high-profile people, it had four or five thousand likes. I dropped my newsletter at the bottom and went from 250 subscribers to a thousand, and the big takeaway that I made at the time was you never know what's going to go viral, you never know what's going to work, you just have to keep showing up and hitting publish. And that set the fly-a-will that's been spinning ever since. So now you got a little bit of popularity on Twitter, how do you actually turn this into something that makes money? The viral post was a breakdown of apology. The result of that was people who wanted me to write a thread on them were now reaching out to me saying, hey, I really like these worldview creation threads that you've been putting together, would you be willing to do one for me? And I had someone reach out to me, he approached me, said, would you do this for me? I showed, sure. He goes, okay, how much should I pay you? And here I am, I have no clue, I don't want to say something because I've been doing this for free. I don't want to say something that would get him to say no. So I'm like, look, I don't know what to say, I don't know what to charge. I'm like, what this? I'll go do this for you. You just let me know how valuable it is at the end of this and you pay me that much. It's like, sure, great, go for it. I was going to ask for $250, but again, I didn't ever say that. So I spent the weekend, Saturday, Sunday just immersing myself 15 hours all the way down the rabbit hole. And I put together a really great product for him. Email's been back like two days later, he's like, dude, this is amazing. Thank you so much. I can't wait to use all this. Can't wait to tell my friends like, hey, you can go do this for them. Putting you in touch with my assistant who will help coordinate payment. So his assistant emails me and says, Hey, where can I pay you? I spun up a PayPal, sent her the link and then $5,000 at my account the next day. I thought it was a typo. And so I sent him a message like, dude, that was so generous. Do you mean to send this much? And his response was like, dude, this was amazing. Is that enough for you? Like, that's plenty. Thanks so much. Like anything else you need, I'm happy to help. And that was the very first time in many years I felt that I again had something where more effort, more intensity led to more results. And that completely broke my brain of, wow, the attention that I generated from writing led to a business opportunity that paid me five grand. We're clearly onto something here. So you make your first $5,000 with ghostwriting. What happens next? Over the next week or two, had a couple more people reaching out where I was probably on pace to make 10 grand a month. But to scale up a ghostwriting side hustle beyond five to 10 K as a side hustle is very difficult. So I zoomed out and said, what was the input that led to this opportunity? Well, it was writing and publishing every day for 30 days on my own. So I tweeted out, hey, I just completed a 30 day writing challenge. It changed my life. Would anyone be willing to do this with me? Because I knew that was intense. I'm going to need some accountability if I want to do it again. Again, I was terrified to charge money because it was like literally a Slack accountability channel. Like how much would someone be willing to pay? But there were so many responses that I couldn't just make it free. So it was $50 and you got your money back if you completed all 30 days. People loved it. The Slack channel was blowing up and I wanted to figure out if I was going to actually charge money for this, what do I need to deliver? So I held over 50 one-on-one interviews, ended up packaging everything that I learned from those interviews into a much better product and charged $99 for it. And then that made 30 grand in December. You're starting to make a little bit of money online. You have this product that's working, but you're still working your full-time job. Tell me about that experience. I've realized I have a scalable vehicle that I can dump a ton of effort into. I partnered with Nicholas Cole to come on and transition this from just a Slack accountability channel for $99 to a full, immersive 30-day digital writing education. So that was all of 2021. Wake up at 4.30 a.m. right for two hours, be at my desk ready to log in for my 7.30 a.m. BlackRock call. Do that during the day. Log off as soon as I could and then build Ship 30 in the evenings. By the end, it ended up working. So 2021, Ship 30 did a million, like 90% margin. I had hit my goal of doubling my full-time job income from my side hustle. FaceTimed him, said, hey, this has been awesome, but I really want to take my kind of life trajectory in another direction. Thanks for everything. And it ended up working out luckily. Yeah. You had this amazing story about how you built this business just from writing online. But tell me, why is the skill of writing important? When you recognize that the foundation for every single piece of content, every product, every video, every podcast is writing. It's the most applicable skill. And so if you can learn that, plus learn to write in a persuasive way or in a compelling way, you basically write your income ticket for the rest of your life. Because you can apply it to any business, you can apply it to any venture, you can apply it in any company. Schools do such a horrible job teaching it. People leave it in the real world and go, what is writing going to do? A thesis statement and like a five paragraph essay and a word count. But that's totally not what writing is. Yes. What's your advice for becoming a good writer and a great writer? So I can help with becoming a good writer because that's all I consider myself. But the best writer I know is Nicholas Cole, who's my business partner. He wrote a book called The Art and Business of Online Writing, which is the first book I read on writing on the internet. I think it's the number one book any person should read who's interested in writing on any kind of social platform. It's going to give you a full crash course of everything you need to know. So that'd be my first piece of advice. It's after this video. Go on Amazon, check that book out. And then my second piece of advice would be always zoom out from the lens of it doesn't matter who you are, how much time you spend on it. The reader does not care about any of that. They care about what the writing can do for them. And if you write with that, what we call an empathetic lens, putting yourself in the reader's shoes and say, how can I create something that they're going to stumble into with a problem? I'm going to solve their problem and I'm going to solve it as quickly as two minutes by the end of this Twitter thread or tweet or long form. It's really just solving people's problems and figuring out how you can do that in the most concise, clear, compelling way. I think when a lot of people think of writers, they think of not necessarily making a lot of money. You've been able to make a lot of money with writing. What's your recommendation for writers who want to make a lot of money? The fastest way to monetize is actually build the skill yourself and then borrow someone else's audience and go straight for them. That was how I earned my first $5,000. I didn't have 20,000, 100,000 Twitter followers at the time. I had 1,000 and I had one person reach out to me that I could charge $5,000 for. That's by far the most sustainable way too because you can build an income stream that's 5 to 10K a month. That doesn't take 40 hours to do. So you have enough to support yourself and then you can go work on building your own audience on the side. So that's our advice to anyone who's looking to write as a career. It's figuring out first how to become a ghost writer and then you're operating from abundance of, I have enough money. I can then pursue my passion project or write about this topic that I know will take longer to monetize than starting right away trying to sell your own thing. Tell me about the tools you use as a writer. Any specific tools you recommend for writers? So if you're spending time thinking you have to have the perfect note-taking system and publishing cadence and content calendar and editing system before you start writing, that's the first thing to avoid. Just hit publish. That's the best tool. So I don't really have any kind of complex to organize system. If I need to find something I've written in the past, I just search my own Twitter. I use type share for all my publishing. So that's a shameless plug for our SaaS that helps you write tweets, long form, LinkedIn, carousels for Instagram, things like that. And then I just use Apple Notes. I have Apple Notes on my phone, syncs to my computer. Anytime I come up with an idea, I just jot it down, wake up right for 90 minutes and expand those ideas. So there's a lot of advice on use this tool, use that tool. It's going to end up being kind of a productive procrastination exercise. So I try to avoid giving too much of a prescription on that. All right, so we're here. This is where you get your work done here. I try to. I lock myself away. I lock the door behind me and try to eliminate all the distractions. I lock into a little bit of a cave, but it's good. Mix it up. What's a day in the life like for you? So what I realized is either be in a full build mode, which is my monk mode, 5 a.m. wake up. I have everything scheduled down to the minute, working out twice a day. Every single meals taken care of in advance. Going to bed at 9 p.m. I know exactly when that's going to start, when it's going to end, so I can sprint very hard during it. And there's a single outcome we're trying to accomplish. That only happens like three or four times a year now. So if I'm not in a monk mode, I call it maintenance mode. I take it down a notch. I try to sleep for like nine hours. I spend more time at the beach and take my foot off the gas because that's where those ideas actually start to percolate for the next sprint. Tell me about some of the struggles that you've had in your journey as an entrepreneur, even going back to some of the days when you're starting. If there's anything that's holding someone back from creating on the internet more than any other factor, it's what their high school friends are going to think about them if they see them on Twitter like writing. It clicked with me that those people are far too busy thinking about themselves to pay any attention to you. You are not that important. I was letting the imaginary opinions of people I didn't even like hold me back from getting started right. When that clicked for me, I go, OK, I should probably just hit publish on this. And I remember hitting publish for the first time and no one read it. Get away! So embarrassing! They're growing up. Won't be long before the thought of a family holiday is just. But with Hilton's staycations all over the UK, we don't need to go far to feel close. Welcome! And with connecting rooms confirmed when we book, we'll have plenty of space to make the most of every moment. Everyone in the photo! When time away means time together, it matters where you stay. Book now at Hilton.com. Hilton for this day. Now I have a new problem. No one cares what I have to say. So this big idea that the whole world's going to laugh at you is actually the opposite problem, which is actually harder to solve of, oh wait, no one cares what you have to say. Why do you actually put something out there that people want to engage with? Alright, last question that we asked to all founders that we interviewed on Starter Story, if you could sit on Dickie's shoulder when you're just starting out, what advice would you give them? So the first one we talked about a ton, which is if the current vehicle you're in is not leading to more income or more skill if you double your effort, find something else. I wish I'd have made that realization right when I started working instead of waiting two years. The second one was once I made that realization, I started down the path of productive procrastination where all I was doing was reading business books without a business, reading writing books without writing, reading leadership books without a team to lead. None of that actually helped me do anything until I had something to work on where I could stop learning just in case and start learning just in time where, okay, I'm starting a newsletter, I need to learn how to write a compelling subject line. Now I can go read that copywriting book, jump to the single chapter on subject lines, surgically read it. Now I have that skill, now I can move on to the next thing. And you end up learning so much quicker when you have a project or something to work on that provides that relative context. And then the last one is that the people you look up to are no more special than you or more talented or smarter, they're just more than likely been doing it for longer. So just zoom out, extend the time horizon and you'll end up getting there too if you just stick with it. And then I'd say the last one is there's never a perfect time to start anything. That's a big fallacy I had that was once I quit my job, then I'll start this thing or once my mom gets better, then I'll do this thing or once work slows down or once I move jobs, that never ends. And so if you can't get started on something today thinking there'll be a better time in the future, that's never going to come. So anytime you can just throw all that out and say, how can I take one step forward on it today? I call it killing your once's. If you can kill all the once's in your life, he'll be in a better spot. Thank you, Dickie. Dude, appreciate you having me. Awesome. This is great. Follow this advice and you'll have a $10 million business ghost writing. Peace. Alright guys, that's it. I hope you liked this video. Personally, I think the coolest part about Dickie's first business is that you don't need any employees or insane funding to start. All it really requires is a laptop, an idea, and a couple of hours of work per day. So if you're curious about building a profitable side project, head to the first link in the description to get our free breakdown of 160 solopreneur business ideas, just like Dickie's. So you can get started on your own journey. Alright everyone, I'll see you in the next one. Much love and again, thank you guys all for watching. Peace.