Hypothetical Journal Entries Written by AI

This is a paying-subscribers-only supplement to “Simulating One-way Door Decisions With AI.” It contains hypothetical journal entries written by Claude Opus, trying to predict how I would feel about raising money for Every.

Raising a small round

Prompt: Based on these journal entries, please write a new journal entry as me with how I’d feel if we raised a small $700k round for Every. Try to simulate me and my personality as accurately as possible.

Response: We decided to raise a small $700k round for Every, and I have to admit, I'm feeling a mix of emotions about it. On one hand, I'm excited about the possibilities this funding opens up for us. It's a vote of confidence in what [[Nathan Baschez]] and I are building, and it gives us some runway to really focus on creating something amazing.

At the same time, I can't shake this lingering unease. I keep coming back to this vision I have of building a company on our own terms - something that reflects our unique perspectives and values. I worry that even with a smaller round, we'll still feel that pressure to hit certain metrics and make decisions that prioritize growth over craft.

I had to do a lot of soul-searching to get comfortable with this decision. I kept thinking about founders like [[Andrew Wilkinson]] and [[Jason Fried]] who have built these incredible businesses while maintaining control and staying true to their vision. That's what I aspire to.

But I also have to remind myself that every path is different. Just because we're taking on some funding doesn't mean we're locked into a certain trajectory. We can still build something that aligns with our values and allows for the kind of creative exploration and flexibility that's so important to me.

I think the key is that [[Nathan Baschez]] and I need to stay aligned and keep having these honest conversations about what we want Every to become. We need to make sure we're not compromising our core needs and values in the process of growing this business.

I'm trying to lean into the discomfort and uncertainty, recognizing that building a company is inherently challenging. But I also need to keep listening to my intuition and advocating for the things that matter most to me.

I believe in what we're creating with Every. I have to trust that we can navigate this path together, even if it feels a little scary and unknown at times. We've taken a small, controlled bet, and now it's on us to make the most of it while staying true to ourselves.

Here's to the next chapter of this wild ride. Let's build something amazing on our own terms, $700k richer but with our vision intact. I have to believe it's possible.

Raising a big seed round

Prompt: Based on these journal entries, please write a new journal entry as me with how I'd feel if we raised a $5m seed round. Try to simulate me and my personality as accurately as possible.

Response: Well, we did it. We raised a $5 million seed round for Every, and I'm honestly feeling pretty overwhelmed and conflicted about it.

On one hand, it's an incredible validation of what [[Nathan Baschez]] and I are building. It means we have the resources to really scale this thing and pursue some of our biggest, most ambitious ideas. And there's a part of me that's undeniably excited about that - the potential to build something truly transformative in the world of business writing and storytelling.

But if I'm being completely honest with myself, this isn't the path I envisioned for us. When I close my eyes and picture the kind of company I want to build, it looks a lot more like a [[Basecamp]] or a [[Tiny Capital]] - something that's intentionally small, sustainable, and founder-driven. A company where we prioritize craft and creativity over hyper-growth and where we're not beholden to anyone else's expectations or metrics.

I worry that with $5 million in the bank and a whole host of new stakeholders, we're going to feel immense pressure to grow at all costs. That we'll get sucked into this cycle of constantly raising more money, chasing vanity metrics, and losing sight of what really matters to us.

I can't shake this feeling that we're strapping ourselves into something that's going to be really hard to control or escape from if it doesn't feel right anymore.

I keep thinking about this idea of building my own "weird wonderland company" - a business that's a true expression of our creativity and values. And I fear that the bigger we go and the more outside money we take, the harder it will be to maintain that vision.

At the same time, I don't want to let my fears hold us back from building something truly impactful. I believe so deeply in Every's potential, and I know that this funding gives us an incredible opportunity to bring our vision to life on a larger scale.

I guess what I'm realizing is that my job now is to double down on staying true to myself and my values even as the stakes get higher. To keep advocating for the things that matter most to me - the craft, the creativity, the independence - even as we step into this new chapter.

It's going to be a balancing act, for sure. But I have to believe that with [[Nathan Baschez]] by my side and a clear sense of our north star, we can navigate this path in a way that feels authentic and aligned.

Here's to the next wild leg of this journey. $5 million richer but also a whole lot more responsibility on our shoulders. Let's build something amazing, but let's not lose ourselves in the process.

I'm scared, I'm excited, I'm determined. And more than anything, I'm committed to staying true to the vision that brought us here in the first place, no matter how big this thing gets.

Not raising any money

Prompt: Based on these journal entries, please write a new journal entry as me with how I’d feel if we didn’t fundraise at all. Try to simulate me and my personality as accurately as possible.

Response: After a lot of deep conversations and soul-searching, [[Nathan Baschez]] and I have decided not to fundraise for Every right now. And I have to say, as soon as we made that decision, I felt this huge wave of relief wash over me.

It's not that I'm totally opposed to the idea of fundraising ever, but right now, it just doesn't feel aligned with what I want to build. I keep coming back to this deep desire to create something that is truly an expression of our unique perspectives and values - a "weird wonderland company" as I've been calling it in my head.

I know that for me, the idea of having investors with expectations that might not align with my own was causing a lot of stress and anxiety.

When I tune into my intuition, it keeps telling me that I need to build something where I feel a sense of control and ownership. Where I'm not constantly straining to hit someone else's metrics or compromising my values in the name of growth.

I look at founders like [[Andrew Wilkinson]] and [[Nathan Barry]] who have built these incredible, profitable businesses on their own terms, and that just resonates so deeply with me. I want the freedom to prioritize craft, to have unstructured time for creative exploration, to make decisions based on what feels right rather than what will drive the most growth.

That's not to say that this path will be easy. Building a company from scratch with no outside funding is a huge challenge, and I know there will be moments of uncertainty and discomfort. But somehow, that feels more energizing to me than the pressure of having investors to answer to.

So here's to betting on ourselves and our vision. To building a business that prioritizes craft, creativity, and doing things our own way. It's a scary and thrilling prospect, but I know in my gut that it's the right path for us.

Let's see what kind of wonderland we can create when we're fully in the driver's seat. I have a feeling it's going to be pretty magical.

My actual journal entries

• So we told [[Eric Stromberg]] yes which means we’re officially going to be a VC-backed company :)
• I feel really good that this happened—I’ve been extremely up front about the business I want to build, and we are going to have a set of investors that are aligned for us to do that. 
• I feel like my partnership with [[Nathan Baschez]] is extremely strong and we’re in an extremely good place.
• I feel really aligned with what we’re doing—if we’ve built a business that actually is the center of gravity for business writing on the internet, and we’re paying writers well, and putting out good, beautiful, useful words every day to a huge audience it will just be such a satisfying thing for me.
• I feel like I’m building a home for myself. For the first time since Firefly I know what I’m going to be doing with my life in a year, two years, maybe 10 years. But definitely for the next couple of years. It’s set: the company and the book. 
• It’s a good feeling. This is the company I was supposed to start. Of course this was the company I was going to start. 
• I’m really grateful. I’m a little tired. I want to remember this feeling because there are going to be times when I’m shaky and I’m like “WHY DID I DO THIS.” “I DIDN’T WANT TO BUILD SOMETHING BIG I JUST WANTED TO WRITE BY MYSELF.”
• Let me remind future me: no. You wanted to do something big and ambitious that was also from the heart, that you could do your way, and you specifically filtered down every opportunity and every potential partner and every potential investor to land at the business that you are currently running.
• And even though it’s REALLY HARD a lot. It’s what you’re meant to be doing—just writing alone in your room would not have been the highest use of your skills.
• At the same time, don’t let go of writing. It’s your soul. And this business is going to be an extension of your soul, but writing will still be at its center. Don’t let it go. Get better at words over the next 10 years, drink them in. You have time.
• You’re going to run this business in a humane and ethical way, and make it into a playground for you and for the writers that you hire.
• But it won’t be a cake walk. There are going to be tough times. Times when you wished you hadn’t done this. Times when you want to crawl in a hole. 
• But you’re going to get up. And you’re going to gut it out because that’s who you are—and at the end of it you’re going to be able to say you built something that was meaningful, and that along the way, moment by moment, you had a lot of beautiful moments. 
• You’re going to make room for the beauty in your life every day. You’re going to make room to think and create. It’s going to happen.

Dan Shipper is the cofounder and CEO of Every, where he writes the Chain of Thought column and hosts the podcast How Do You Use ChatGPT? You can follow him on X at @danshipper and on LinkedIn, and Every on X at @every and on LinkedIn.