Root Cause of Solopreneur Success
Before, During, and After AI
In this episode of Root Cause we sit down with Orel the solo builder behind WriteStack, the biggest tool out there for Substack creators. Orel spent close to 600 days shipping around ten products that made zero dollars, then picked one thing, stuck with it for six months, and turned it into a six-figure business. He has lived three versions of solo building in three years: before the current AI tooling, as it arrived, and now. We get to the root cause of what AI actually changed for one-person companies and what it didn’t. Building got faster, but knowing what to build, and sticking with it long enough to find out if it works, is exactly as hard as it always was. Honest and unfiltered, including the messy parts most “become an entrepreneur” content leaves out.
Watch & listen:
Below you’ll find the text version of this episode, for those, who prefer reading :)
Guest: Orel Zilberman — Solo builder and creator of WriteStack
Orel Zilberman spent 599 days building around ten products that made exactly zero dollars. Then he picked one thing, stuck with it for six months, and turned it into WriteStack, now the biggest tool out there for Substack creators and a six-figure business. He started before the current AI tooling existed, kept building as it arrived, and is still building now, which makes him a rare person to ask what AI actually changed for one-person companies, and what it didn’t.
You don’t have to build something new
Nune: I have friends who, when I tell them what my business does, or what my previous startup did, say “well, doesn’t it exist already?” The sentiment is that you need a revolutionary, unique idea to have the right to be a startup or a creator. I don’t think that’s the case. People build for different reasons. What’s yours? Why did you start?
Orel: First, the idea that you have to be novel and create something new is absolute nonsense. When I started creating tools for Substack creators, there were probably a dozen other tools out there. They were not good, in my opinion, but they were there and people knew about them. I came in, I fixed a lot of things, I built something that was already there. And right now WriteStack is the biggest tool out there for Substack creators by far. You don’t have to build something new. You just have to improve something that exists.
As for why I started, it began during COVID. About three months in, I read my first ever nonfiction book. It was about self-development, growth, and a little bit of entrepreneurship, and I got really hooked. I read more and more on the topic, and one thing led to another and I slowly developed that itch to do something besides work in a nine to five. Even though the salary for a software developer, which is my background, is very high, I just hated going to work every day. The people were extremely nice, but I still didn’t feel like it was my place.
I started investing in the stock market, and that made me some money and reassured me that I could do something beyond working. I also came out of a video game addiction around then. At one point I decided I wanted to quit everything and just focus on building something people would be willing to pay for. So on August 2023 I quit my job, and ever since then I’m building. And just to correct you, it’s actually 599 days that I built things that didn’t make any money. If only that first payment had come a day later, it would have been a clean 600.
Nune: You’re one of those people who keep statistics about everything.
Orel: You’d be surprised, but I’m very messy. Very messy. I have papers that I write random stuff on, I have Linear, I have Trello, I’m talking to Claude. I’m all over the place.
Nune: That’s important for people to hear, because some of those “become an entrepreneur” books give the impression of a well-organized person who gets up at six AM, goes for a run, and never misses anything. In reality it’s a very creative process, and as a consequence a very personal one. There are people who are well organized and people who are messy, and that doesn’t prevent them from creating something.
You don’t have to build something new. You just have to improve something that exists.
What Substack and WriteStack actually are
Nune: Some people listening might not know what Substack and WriteStack are. Can you explain Substack itself and what your tool does?
Orel: Substack is a social platform that combines something like Twitter and Medium, where you can write both short form content and long form articles. It lets you have followers in the form of subscribers, and those subscribers subscribe to your newsletter by giving you their email. So they took the good thing about a social platform, the short form content and the feed, and integrated it with email collection and newsletters, and combined it into one platform. It’s a crazy achievement. X is following suit, and LinkedIn as well, adding their own long form part.
WriteStack is a tool that helps you manage everything around Substack. The notes you need to put out consistently, what to write about, replying to comments, statistics, and a lot more. It helps you manage everything in one place with automations.
Nune: What I like about Substack is that it gathers people who like long form, which is what’s lacking from a lot of social platforms. It’s also a way to be in touch with your readers, because you get immediate reactions and comments on your long form. I also expect a lot of actual fiction writers to be there, writing the kind of novels you used to write on the forums and getting feedback while you write. It can get a bit noisy with people who write on Substack about Substack, which you have to do because your tool is all about Substack, but I find it sometimes too noisy. Still, I enjoy it, even though I joined not that long ago.
They took the short form content and the feed, integrated it with email and newsletters, and combined it into one platform.
Why even bother building at all?
Nune: This brings me to the “why bother” comment I hear a lot. If you’re building for a platform, or a tool related to a platform, what if that platform releases tools that do what you do? They have the competitive advantage: more customers, more users, a bigger team. Why even bother if they’ll come and replace your tool?
Orel: I have several answers. First, I’ve learned so much from building WriteStack that if something happened and I had to end it, I could build another product and make it profitable quite fast. I know what to do. That’s something I didn’t learn in my first year and a half of solopreneurship, not even close to what I learned in the past year.
Second, you can make money and get users into your app while they’re still working on theirs, even if you don’t know whether they’re working on anything like it.
Third, why would they even bother? WriteStack currently makes ten thousand in monthly recurring revenue, and ten thousand dollars is literally nothing to them. It doesn’t move the needle. They’re better focused on things that bring bigger creators to the platform, like improving the newsletter, the statistics, adding drip campaigns, rather than spending hundreds of thousands of dollars on engineers to build WriteStack 2.0. And even if they do, you’ll have enjoyed the journey and learned a lot. Let’s say in a year they build everything you have and shut you down. Or they don’t even build it, they just say “we don’t want third-party tools, get out.” I still had plenty of time to learn what works and what doesn’t, how to move on and create something new, and I made money along the way.
Nune: Only benefits. It’s a very powerful feeling once you build something and it works and brings you good feedback, because then you’re empowered to build more. It’s similar to what you said about feeling miserable in your nine to five. Part of it is that you understood you can make money with a nine to five, you can force yourself to find another position. That’s already in the realm of your possibilities. So why not reach out for something new, challenge yourself, and not be miserable while you’re doing it?
Orel: Another great benefit is that I’m not worried I’ll have to go back to work. I was on vacation for three and a half weeks, a complete vacation, and nobody was telling me “hey, you have to come back right now.” It’s a liberating feeling.
Even if they shut me down, I still had plenty of time to learn. And I made money along the way.
Nune: There’s a third “why bother” going around, and it’s all about AI and how easy it is now to write a product. The sentiment is that anyone can take AI and build what you’ve built, that SaaS in general is dead, that product development is dead, because anyone can do it. So why would somebody pay extra for your product when they already pay for their Claude Code subscription?
Orel: First of all, you can build almost anything today, that’s true. But you have to be very technical. You need to maintain it, make sure everything works, and know what’s going on behind the scenes. I tried to build a complete app from scratch with Claude Code Opus 4.7, a very simple app that collects feedback from people and emails it to me. That’s it. And it failed miserably. It had a lot of bugs. I tried to fix it many times. The moment it’s a little bit complicated, the AI struggles, and you need to know what to do, where to point it, what to add, what services to use.
For personal use you’ll probably get there eventually and build something for yourself. But if you’re making an app to sell it, having a complete product doesn’t mean you’ll have users. There’s a lot of competition, you need to be unique, you need a distribution channel to get people to use it, to pay you, and to trust you. Just having an app doesn’t mean you’ll have users. And building for yourself means spending a lot of hours, a lot of days, making it work exactly the way you want with all the features you want. People prefer to pay someone who built it, adds features, and maintains it a few bucks a month, and save those hours for something more valuable. You can spend a week building your perfect app for one specific use case, or pay someone twenty bucks a month and make something else worth way more than twenty bucks in that week.
Nune: Thankfully people are starting to understand that AI building can bring you a prototype, a working first version, but nobody saves you from the continuous iteration. And the person who has dedicated their whole time to one specific problem has an endless advantage over you, who just built it in a week and said “that’s it, I have other things to do.” So no, SaaS is not dead.
Orel: Exactly. I invested the last year and a half into learning Substack, knowing what works, what doesn’t, what any creator needs, and I’m still improving and iterating. People come to me and say “I can build a scheduler for myself now,” and I say okay, you can. How long will it take you? Then I ask a few technical questions. How would you import notes? How would you create a bunch of them and schedule them? And that’s just the scheduler, not all the other features WriteStack has. You can build something very simple, but to make it really good and not waste your time, you need to spend a lot of time.
Nune: Plus, after you build it for yourself, the second stage for any product is making it work for thousands of users, which is a whole other story, and I think you’re dealing with that now.
Orel: Yeah. I don’t think AI can replicate WriteStack as it is, because I have around ten different projects that each do something else. One gets the data, one reminds users about certain things, and there’s a lot of infrastructure in AWS and Google. It’s a lot of things beyond just having code that runs.
Just having an app doesn’t mean you’ll have users.
Choosing what to stick with
Nune: You mentioned those 599 days of no income. Before WriteStack you tried other things, and I’ve read that you said what made WriteStack a success is that you stuck with that one thing. People often hear “stick with it and you’ll succeed.” But the problem most of the time isn’t the patience to stick with it, it’s choosing what to stick with. There’s a lot of unknown. You don’t know if it will work, and it’s hard to believe the promise that if you do this long enough, one day it will pay off. So how do you know the thing you’re doing is worth sticking with?
Orel: Now I know. Now it’s easy to say. But back then I had no idea what was going to work, and I’ll let you in on a secret: I thought every single one of my ideas was a killer, the one I was going to break through with. There were a lot of unknowns. I had a lot of times when I felt miserable and depressed and didn’t know if I’d ever make enough money to live off of. It’s hard. It’s definitely hard.
The way I kept myself going is that I read books, a lot of books, and every book about entrepreneurship and self-growth says it takes time. People say 98% never make it, that 50% of businesses close, whatever. It doesn’t mean you can’t do it. And even if you fail, that’s 100% okay, because then you learn from it and move on to the next idea, and you keep learning until you get something working. And even then nobody promises anything. It’s up to you to keep trying, because eventually you’ll get the opportunity to succeed.
Nune: I like a quote from a science fiction book that says there is no such thing as luck, there is only adequate or inadequate preparation to cope with a statistical universe. If you’re prepared enough, you’ll get a lot of chances in your life, and if you’re prepared to take the chance and try something, eventually one of them works out. But to get practical: with all of those ideas you thought were genius and that didn’t work out, when was the point you said “this isn’t working, I should switch focus”? Can you draw a pattern, or was every one unique?
Orel: Before WriteStack, every idea I had I gave maybe a week or two or three at most, and if I didn’t see any traction I dropped it. That was my number one mistake. I didn’t stick to one product long enough to even start marketing it, talking to people about it, getting feedback, and improving it. What I believed from what I read online was that you need to ship fast and kill even faster, get as many products out there as you can and see what works. That can work for a big creator, because when you have a lot of followers you can put out an idea and see how people react really fast. When you don’t have an audience, you can never know until you try and ask people manually, one by one, “hey, can you try this and tell me what you think?”
And about luck being preparation, I think it was Robin Sharma who said luck is preparation meeting opportunity. That’s exactly what happened to me. I used to spend a lot of time on Substack. I started on YouTube, moved to LinkedIn, then Twitter, then Substack. I was trying to be consistent on X and not really managing. But one day I opened the app and saw a tweet from Thibaut, the founder of Taplio, Tweet Hunter, SuperX, Revid, and a lot of other products. He was looking for a co-founder to build a Tweet Hunter competitor. Tweet Hunter is essentially WriteStack for Twitter. His previous co-founder hadn’t worked out, so he was looking for a new one, and I thought this could be a great opportunity to get myself out there, get people to know me, build something and make money.
So I sent him a message, then another one, then a video, then another video, until he replied. We started talking and he gave me about two weeks to add a feature to one of his apps. He had that Tweet Hunter competitor, SuperX, already built, but not the way he wanted it. He gave me the code and the data and asked me to add a feature. I had to learn so many new technologies I didn’t know back then, and I did it and learned them and sent him the code. Eventually I didn’t get to work with him. But doing that and learning those technologies made me realize it could all transfer into Substack. Everything I learned from SuperX I could transfer over. That opportunity is what got me into building WriteStack.
Nune: So if you hadn’t taken that step that some people would call a failure, it wouldn’t have brought you to the idea, and it wouldn’t have given you enough knowledge to start it. Once you decide to give yourself time for experimentation, you also have to give yourself time to fail, because it’s not a failure, it’s a learning cycle. And if you grab enough of those opportunities, one of them works out.
Orel: Exactly. And you need to take those opportunities.
Even if you fail, that’s 100% okay, because then you learn from it and move on to the next idea.
The cold start problem
Nune: What I also liked is what you said about followers. When you have a lot of them, it’s easier to experiment with short-lived ideas, even short-lived content. You can drop thoughts that contradict each other just to check the market’s feedback. But there’s the cold start problem: if you don’t have a lot of followers, what do you do? I think you partially answered it, you really spend time with every individual user and ask them for feedback. Right?
Orel: Right, that’s what I did in the beginning. I sent thousands of direct messages. I got on probably hundreds of calls trying to get people to use it. I’d give it to them for free, just use it and tell me what you think. Once people started using it more, around April 6th, I got my first payment, then another one, then more users. Then I’d ask again in the direct messages: I’ll give you a month for free if you jump on a call with me, sign up, and show me what you do. And I learned from that.
Today I use PostHog, which records the sessions of people who use WriteStack and summarizes them, and I learn from that and create papers with things I need to do to improve. I have a support chat in WriteStack that I reply to personally, and I learn from everything. I summarize all the conversations I’ve had, send it to Claude, and it gives me things to improve. It’s just the manual work at this stage.
Nune: It’s a lot of manual work, but I think the whole point is the manual work, because that’s the only way you actually learn from the feedback process.
It’s just the manual work at this stage.
The tools that help, and the ones that hurt
Nune: A lot of people would want to hear which concrete AI tools you use and how they help you, and maybe if there’s something where you’d say AI is making it worse.
Orel: AI definitely helps with a lot of things, though I don’t use that many of them. I’m a bit behind in the AI game. I use Cursor for coding and Claude for daily use, talking to it, thinking about ideas, consulting with it, brainstorming, creating content. I also use Revid, another product from Thibaut, to create the reel videos I make every day.
Generally AI helps me a lot, but it also sometimes makes me very unproductive. I catch myself thinking, “okay, I can complete that really fast with AI, so I can procrastinate and do it in thirty minutes,” and then I find myself doing other things instead of working, because I know I can finish it quickly. If you look at the big picture, it’s saved me weeks or months of work. But in the day to day it sometimes makes you less productive and more prone to procrastinate.
Nune: I just yesterday published a small article about how these AI chats are like social media. You get into a conversation and it’s one more turn, one more question, and it even offers you questions, so you get dug into the hole. It’s like scrolling an endless reel, but on a specific topic. You have to get yourself out of that conversation and actually go do something.
In the day to day it sometimes makes you less productive and more prone to procrastinate.
Will AI take your job?
Nune: You took the leap, you quit your job. A lot of people right now are anxious about AI taking over their job. Do you see AI taking over software engineering positions? And as someone who decided to leave the nine to five, do you think anyone can do that, or does it take a special kind of character?
Orel: I don’t think AI is taking over any sector in software development soon, because it requires a lot more than coding. You need to understand so many things beyond it, especially for bigger products. AI cuts development time by a lot, so software developers who aren’t good enough will probably be laid off. But if you’re really good at what you’re doing, you’ll find a way to be better with AI, and then there’s no reason to fire you unless a company closes an entire branch.
From my experience there aren’t a lot of good software developers. Most people just come in, put in the hours, and go home. They don’t care about anything besides their paycheck. That’s the reality. If you tell somebody “I need you this weekend to work on something important,” they’ll never do it. And that’s fine, it’s their decision. But if you want to be better than everybody else, you need to do the things that nobody wants to do.
Nune: True, you need to put in the extra effort. We just had an episode recorded yesterday where we discussed that a software engineer’s job is so much more than coding. It’s knowing the domain, being able to communicate with your peers, with customers, with clients.
Orel: Right, it’s being able to connect the dots, to understand one thing in one area and apply it in another, and to think in a broader way. And actually wanting to be better and improve as a software developer, not just clocking in for the money.
Nune: Meta thinking.
If you want to be better than everybody else, you need to do the things that nobody wants to do.
Pick one thing and give it six months
Nune: We talked about what AI changed and what it didn’t, that you still need to focus and iterate. Anything else you’d advise someone who has an idea and is unsure whether to try it, unsure whether anybody would use it?
Orel: This is my number one advice, honestly: give yourself a few months to focus on that one thing. You’ll build it in a few days, you’ll have the first MVP ready, and then you’ll need to get people to use it. When you’ve set aside a lot of time for that product, after you’re done building it you start thinking, okay, what do I do next, how do I improve?
What I did personally was take five books I really love about marketing and tell myself I was going to read them on repeat until I made my first dollar. It took me four months, rereading them time and again. Three books by Russell Brunson and two by Alex Hormozi. In that dead time after I finished building the first MVP, my brain started looking for things to do, and as I read I got points I started implementing. Whereas if I’d read them before, I wouldn’t have tried to implement them, because it wasn’t the right time for me to get that knowledge. When you’re in the state of mind of doing something and you read something related to it, it’s much more effective than just reading about it and later trying to recall it.
Nune: That’s very true. When you read those books they make you think in a certain way, but reading them while you’re doing things, it clicks in a whole different way. A lot of those books are written by people who actually tried it and wrote it during that trying period, and that’s why they click in the process itself.
Orel: Right. You’re doing it, and suddenly the writer says “and then you’ll hit this point and you’ll need to do this,” and you think, he’s right, let’s try this.
Nune: I really liked a quote by Christina Koch, one of the crew members who flew around the moon in the last flight. She said, “find what you can do the slowest for the longest and still absolutely love it, and go in that direction.” Sticking to one thing and doing it slowly, every day, is what you need to find. Not something that excites you right now and then is gone, but something you can stick with.
Orel: In my opinion it’s less about the thing and more about the goal you want. I had dozens, maybe hundreds of points where I felt I’d had enough, that it sucked and I really wanted to stop. What kept me going was being stubborn and knowing that if I pushed through, I’d be better than anybody else. I’m like a kid in that sense. I want to do the opposite of what people think. So I knew that if I kept pushing, eventually I’d get to my point, and I needed to do better where most people break.
For example, I used to go to a spin class with a lot of people. When everyone was at the hardest point, when I saw people around me suffering and barely pedaling, that’s when I felt I needed to be better. I can’t let it break me where it breaks others. That mindset honestly came from reading David Goggins three times and listening to his audiobook. It really inspired me to be better when others are struggling.
I can’t let it break me where it breaks others.
Books, learning, and the major he’d choose again
Nune: To go the extra mile. You’ve already mentioned a lot of books, and I’m a big bookworm too. Do you have more recommendations?
Orel: For sure. I don’t have my phone, but I have an app a friend built five or six years ago that we still use, with all my books and favorites. The latest one I read is The Obstacle Is the Way by Ryan Holiday. I absolutely loved it. Storyworthy, also about storytelling, is very interesting, crazy good if you’re into storytelling even a little bit. The Wealth Money Can’t Buy by Robin Sharma is great. I have 235 books I’ve read in there. And another book that made me take the step and quit my job is The Millionaire Fastlane by M.J. DeMarco. That’s the one that differentiated between me working the nine to five and me quitting.
Nune: You’ll send me the list and I’ll post it. I’m happy there are still people around who learn from books. From what I’m hearing, maybe you can write a book someday. What do you think?
Orel: Not in the near future. I’m struggling to write an article every week.
Nune: What I also like, and want to tell the audience, is that you’re documenting your journey. You have the newsletter, Indiepreneur, where you write these things down, which will hopefully help someone avoid some mistakes or be more courageous where they’re worried. There’s a tradition that every guest leaves a question for the next one. In the previous episode, Ia asked: if you had to start your career or learning journey and pick your major right now, would it be different from what you had, and if so, what and why? What’s your take on learning computer science now in the age of AI? Is it still valid, and would you do it, or take something else?
Orel: To answer her question, I wouldn’t change my major. I have a software development degree, a bachelor of engineering. I wouldn’t change it, because even though you can do stuff with AI, AI is not taking the entire sector, not anytime soon. So many people predicted it. Jensen Huang, the CEO of Nvidia, said AI is going to take over software development jobs. And the CEO of Anthropic recently said he was wrong about it and it won’t actually happen. So I wouldn’t change my major. I’d do exactly what I did.
Nune: A lot of them are taking it back. Sam Altman took back his words, Dario Amodei from Anthropic took back a lot of what he said about replacing engineers. Whether that’s political, economical, or reality is a bigger question. But a lot of people who are hands on in IT all say the same thing: there’s no replacing, it’s still the same job with a different tool set.
Orel: And it’s interesting that the media makes it look so much worse than it is. Take Wix, for example, laying off thousands of software developers and employees. That’s because the competition is so strong that they’re losing ground, so it doesn’t make sense for them to hold as many developers as before. AI had its impact too, but it’s not only AI, and people make it look like AI is completely killing the market. Companies like Meta, Microsoft, and Amazon that are laying people off all hired so many software developers during COVID. Back then, finding a software developer job was as easy as finding a job at a supermarket. They overhired, they overstaffed, and now they’re reducing staff. Obviously AI had its impact, but there are a lot more things behind their decisions.
Nune: It’s easy to blame AI and say it’s all AI.
Orel: Exactly. And that’s what people want to read. It makes them feel something, so they want to consume more of that content and see that AI is killing the industry.
Nune: What would be your question to the next guest?
Orel: My question to the next guest would be: what is the one thing you would tell yourself at the beginning of your journey that you know now but didn’t know then?
Nune: What would be your answer in your case?
Orel: Pick one idea, focus on it, and give it at least six months. Especially when I first started, when there was no AI to write for you.
Nune: Stick with it.
References
Quotes mentioned in this episode
“There is no such thing as luck. There is only adequate or inadequate preparation to cope with a statistical universe.” — Robert A. Heinlein, Have Space Suit—Will Travel
“Find what you can do the slowest, for the longest, and still absolutely love it, and go in that direction.” — Christina Koch
Orel also reached for Robin Sharma’s version: “luck is preparation meeting opportunity.”
Tools and products mentioned. This is not a commercial, but if any of those want to become a sponsor for my show, get in touch with me 😀
PostHog (not a sponsorship, just what Orel shared he uses. But if you are PostHog and want commercial, get in touch with me :D )
Revid (same)
Cursor (what Orel uses for coding)
Claude (daily brainstorming, and the Claude Code Opus 4.7 app-building experiment that didn’t go to plan)
Thibaut’s stack that shows up in Orel’s origin story: Taplio, Tweet Hunter, and SuperX
Books mentioned
The Obstacle Is the Way by Ryan Holiday
The Wealth Money Can’t Buy by Robin Sharma
The Millionaire Fastlane by M.J. DeMarco (the one Orel credits with making him quit his job)
My article that came up: “AI isn’t a tool, it’s social media”
The build-compression is measurable. The trust timeline doesn't move. I've watched teams celebrate deployment speed while the adoption curve stayed flat for months - the tool was there, the willingness to use it visibly in front of each other wasn't.
You can ship faster. You still can't shortcut the part where people decide whether to show up.
Downloaded. Will listen in the plane 😊