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Jumping out of a rocket ship to be an indie hacker

This is the story of why I left a few million in unvested stock options to be a full-time indie hacker.

Almost 3 years ago, I joined a tiny startup that has since become a multibillion-dollar juggernaut.

When I first joined, I fell in love with making stuff that grew the business and made customers happy. It was my dream job. Every day was different, each experiment worked differently. It was, quite honestly, the best dopamine.

The next opportunity became hiring and managing. It was a new challenge. I was building society-approved career momentum. More dopamine.

As the novelty wore off, I came to the realization that I wasn’t interested in the next level up. Being a Director/VP is gratifying in theory, but not so much up close. I lost interest in the game.

Still, it was hard disentangling my identity from being an early employee at a successful company. I felt massive FOMO.

If you’re on a rocket ship, why would you jump out mid-flight? Yet somewhere along the way, our paths had already quietly diverged.

The company has grown 20X in size since I joined. Whenever that happens, you end up doing multiple tours of duty. You take on different missions based on the company’s needs. And you hope dearly that you scale with the company, which is corporate speak for growing the scope of your contributions proportionally.

For the most part, I was scaling. But the journey that was once an exciting adventure turned into an exhausting slog in my final months. A new revelation began to dawn on me: I wanted to build freely, and on my own terms. Even if it meant making less money, and taking on more personal risk. Working at a startup is hard enough without feeling like your heart's not in it.

A steady paycheck and a lot of unvested stock options is hard to turn down though. When you get good at trading your time for money, it’s hard to imagine replacing it with something else. I narrowly escaped this trap by reminding myself that it’s always worth trading money I have today for something I would regret at the end of my life.

I used to think a career meant working at a company. Then I learned you can start a company. Now I believe a career is simply about making something people want, and capturing some of that value.

Why trade time for money when you can trade value for money? The internet has massively expanded the spectrum of possible careers — a generational shift that remains highly under-appreciated.

Even so, I’m still terrified to embark on this third act. Act 1 was learning to analyze businesses as a consultant. Act 2 was learning to operate a business as a PM. Act 3, I hope, is learning to bootstrap a business.

I’ve never identified as an entrepreneur. Is building a business a learnable skill? Stay tuned.

The first idea I’m playing with is around productizing my experience. Setting metrics, building products, and storytelling are valuable skills. It’s taken me years to learn, and they tend to be gated behind the walls of select places. I plan to build in public, and teach everything I know.

New to this community, but grateful it exists!

You can read my full story here, including learnings on money and startups: https://productlessons.substack.com/p/this-is-my-stop

  1. 2

    Welcome to the party! I resonate with your feelings that you never thought of yourself as an entrepreneur. I never wanted to be one either, and tried every other possible work arrangement I could think of to find the right fit (freelance, partner, part-time, full-time...). But in summer of 2018, even my "dream job" (high paid, remote, full ownership) had gotten boring. I just didn't have any other options than to start my own company if I wanted to keep growing.

    I assumed it was gonna be hard, but the right word is more like BRUTAL 😅. However I've grown as much in the past 2.5 years than in 5 years prior, which is the most important thing for me in life.

    Even starting with a lot of cash, it gets scary and stressful eventually. Way more than I imagined (and I tend to be conservative). However I do learn to figure it out as I go, and it becomes more and more manageable. I wouldn't have it any other way.

    Godspeed!

    1. 2

      Aw thank you! I will brace for the brutal journey ahead :) Very glad to hear that you've accelerated your personal growth, I hope for the same

  2. 2

    Good luck and safe landing! Great articles so far, just subscribed.

    1. 1

      Thank you Steven! I too hope for a safe landing haha

  3. 2

    I love hearing inspirational stories like these on IH! 😄

    Best of wishes for what the future holds!!

    1. 1

      Thank you Brayden!! Will share updates on the rest of this story :)

  4. 2

    So nice to see you share about the start of your Indie Hacker journey! We are going to learn so much from you :)

    I’m a big fan of your newsletter since I found it, and of you!

    It takes a lot of courage to make that leap. I’m confident you’ll do great things. You know I’ll be rooting for you in this journey.

    1. 1

      Thank you Janel!! Following your lead here and on Twitter ❤️

  5. 2

    Thanks for sharing your story! I've been a reader of your Substack since July, and it's been a joy learning from your journey. I was actually going to reach out and suggest joining IH, but was glad to see you're already here! I think there's lots to explore in productizing your experience and am excited to see what you come up with.

    I've truly found so much value in your weekly newsletters, so if you feel like i'm your ideal target user, I'd be happy to help in any testing/feedback down the line.

    Good luck!!!

    1. 1

      Aw thank you Darlene! Appreciate your support, and will probably reach out to you sometime soon :)

  6. 2

    Good luck and thanks for sharing! You mentioned you're planning to"retool yourself as a fullstack creator" - does that mean you're going to teach yourself to code? I consider myself a "recovering business person" who previously worked in various line roles in Big Tech and eventually quit and taught myself to build my own products and consider it the best decision I've ever made.

    1. 1

      I left it open-ended because I'm curious how far no-code will take me. :) I probably will find myself needing to pick up some coding skills though. What worked for you?

      1. 1

        Based on my own journey, I think the best thing is to have something concrete in mind in terms of you want to build (even if it's just a project for learning) and what platform you want to start with (e.g., web vs. mobile). Then, see if you can find an open source or sample app(s) on github that already provide some of your app's functionality that you can mess around with just to see how things change.

        Simultaneously, sign up for like a Udemy course or something that provides an intro to your desired platform or coding language (e.g., Ruby on Rails or Android development). That will help you at least get your environment set up (which in and of itself can sometimes cause show-stopping frustration in the early days). And then get really good at just Googling errors, because someone out there has definitely had the same problem.

        All in all, if you're motivated by your project, problem-solving in general, and find you get immense satisfaction from the "hey it worked!" moment where it kind of feels like play, I think you'll be well-positioned to hack together your own MVP.

        1. 1

          Really curious about your experience, I spent 6 months with nocode and frankly its a superpower for very basic things like static websites and some abstract automation if tools support APIs. However, building something more complex with dynamic features just makes it a struggle with trying to glue different pieces together, using tonnes of tools, and obviously the ramp-up in price. After that experience, I just decided to ramp up on vanilla JS and node to be able to spin-off something more like SaaS rather than job boards. How was your journey from learning to product?

          1. 1

            Awesome! Yes, I'm a vanilla JS + node man myself - I actually don't know any frameworks (yet) and have a sense of a lot of them are overkill for my purposes, as my apps are pretty simple - though I probably also have a lot of bad habits / practices being self-taught where knowing a framework might help.

            My journey was pretty ugly and I'm still on it. I've been fortunate where I gradually stair stepped up with various projects and needs. I started messing around with code a few years ago using Google Apps Scripts / automating Google Sheets, so I knew some basic Javascript and how to do fetch calls with APIs. Then I ended up teaching myself Android development to build a private B2B Android app for clients.

            Starting in the late spring, I had to build a Shopify POS integration for some of my existing clients. Prior to this, I had no idea really how the web worked - I literally didn't know how sites got on the web (someone had to explain to me that you upload .html and .js files to a service like Netlify). So I began diving in - a simple html + js list view with checkboxes, and using their App Bridge API to add line items to the cart.

            After I got that working, I had an idea for my own standalone apps for the Shopify app store. I learned how OAuth worked, learned Node.JS in the process and eventually got my apps approved. So that brings me to today. If I were to not build on a platform, I would likely use Firebase for my user accounts / db (since I already know it) and then Stripe for billing.

            I've made a lot of mistakes and am still learning and trying to improve my workflows. I'm using Google Cloud Functions / Node.JS and for the longest time I didn't even realize you could do local development with GCF - so I was deploying after each commit and waiting minutes at a time to test minor changes! I also didn't incorporate pull requests and merging changes until somewhat recently.

            Hopefully there's something in there that helps. I wonder too if there are easy ways to string together certain no code aspects along with roll your own components? Anyway, good luck!

        2. 1

          Ah thank you! That's very helpful. I've made the mistake of trying to learn coding without a serious project before only to have it go nowhere.

  7. 2

    This is quite the leap. It takes a lot to give something up when the other side of the deal is unknown. I appreciate your ability to take that risk. I look forward to seeing what you build. While your journey thus far was common, I think this single move is definitely uncommon. Congratulations on going against grain and actually DOING something rather than tweeting some contrarian nonsense and going back to your job at a FAANG company like a good number of folks on tech-twitter.

    Good luck with everything. You are going to do great :)

    1. 2

      Hahaha I appreciate your support! Struggled a lot with it, but knew it was the right decision when I felt the greatest relief after sharing the news.

  8. 1

    Cool story! Good luck!
    Do you have any cash stashed aside? Otherwise, it will probably be a really bumpy ride...

    1. 1

      I do, thankfully! :) Hope to weather the bumps

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