I quit my 1+m$/year job to work full-time on my own project

At the beginning of January 2021, I quit my job, left the Bay Area, and moved to Houston, Texas, with my family. Since then, I have been working full-time on my own project Riddey (former Coolboard). Riddey is a visual collaboration space for engineering teams. It aims to make remote work more effective by leveraging machine learning and novice UI techniques.

It has been a tough half a year with many ups and downs. I have been working day and night to make it happen. Still, I have a feeling that the project is moving at a snail's pace. I manage, code, design, deal with the money, do the marketing, hire and let people go. I take part in everything and feel that I don't do anything.

I bootstrap and already spent a small fortune on the project. Meanwhile, I have to pay the bills and sustain my family. We are in the red, and I cannot see the light at the end of the tunnel yet. It is not easy, nay, it is very hard.

Why am I doing this - you may ask - if I could become a multi-millionaire within 3-4 years if I stayed in employment? The answer is simple: because it makes me happy.

I was always fascinated to see an idea turning into reality. As a kid, my favorite toy was the Lego blocks. I love to build, and now I can do it as much as I want. I also enjoy the freedom: it is up to me how to schedule my time. It is me who makes the decisions. All the responsibility is on me, and it is me who has to face the consequences.

I constantly learn, and this is the best. I wear many hats, and this pushes me to study, research and practice. I learned more during these six months than in the previous two to three years: product-, project-, and engineering management; hiring, negotiation, taxation, UX design, and more.

Last but not least: I met great people. I received support from many, even from strangers. I am lucky to have an incredible team and am astonishingly proud of what we have achieved so far.

What we achieved? We reached our first milestone and just launched our private beta. If you are interested, you can read more in the release notes. Also, please sign up for beta testing by sending a PM if you want to help. We are in great need of feedback so that we can build a useful application. Thanks for reading!

  1. 4

    What is "1+m$/year"? Do you mean $1m+?

    If so do you care to elaborate on that; it's quite a big statement given that the average CEO salary is a lot less than that. What do you do (no need to be super specific) that pays over a million dollars a year?

    PS Riddey looks great. How do I get an invite?

    1. 1

      Hey! Yes I meant $1m+. Sorry. I knew that people will doubt it, and it is very reasonable to have doubts.
      If you don't mind I won't paste my w-2 :)
      I wasn't anything super interesting, I was a staff level software engineer at a publicly traded company. In the Bay Area staff level means ~$600k/y see levels.fy. I was lucky, because the stock prices were low when I joined, and during my tenure their value quadrupled. If I stayed, I probably would make around $1.5m this year. If you need more info, pm me.

  2. 4

    just a few thoughts - I think an explainer video would be beneficial, show two or three people, maybe on a zoom meeting, talking and filling out a board collaboratively using most of the features but hop around to show them doing it using disparate devices that prove the accessibility.

    Also, show me a few samples of what a fully populated board would look like, you show a flow chart, add a few more, mostly because people want to see what the maximum amount of data it can display looks like even if the information displayed is fake and/or alien to them.

    Can I keep going outside the confines of the screen? Is it effectively "edgeless"?

    In your release notes, I would move "renewed frame" to the bottom below the triangles - it's such an "inside the app already " issue people might struggle to understand how or why that was any kind of concern or requirement. Cool feature, I just can't know enough about it yet to appreciate it.

    I am guessing Accessibility is Riddey's Unique Selling Proposition - I am not an online whiteboard user so I don't know if that's the pain point that's the worst thing about online whiteboards. You lead with it on your website but you might need a tag line or H1 header under your logo that says "The online whiteboard that's accessible to everyone".

    I see a logo then huge letters saying "Accessibility" and under it "Accessible to everyone" but I don't find out what Riddey is until I get to the paragraph-sized print below it.

    I would suggest logo, under it my tag line suggestion, then pick one or the other of "accessibility" or "accessible to everyone" because it's redundant - let's say you keep the "Accessibility" then consider changing the text to say:

    "Unlike other online whiteboards, Riddey can be accessed from any device. No matter if it's a laptop with a touchpad or an iPad Pro® with the best pencil. The experience will be seamless across devices allowing everyone to collaborate."

    The "allowing everyone to collaborate" closes the loop on your accessibility USP, dumb as it seems you should be completing the thought for them.

    ditch the colon, make "Riddey" the same color as the text so it doesn't look like a clickable link and appears in a color different than the logo.

    Under the accessibility text block with the four device pics on the right maybe add a screenshot on the left and bullet points on the right with AI at the top of the list or alternately add a sentence about how you use AI to turn a freehand drawing into crisp shapes. That is likely your other USP - fire all your USP bullets on your main page.

    1. 2

      Wow this is AWESOME feedback.

      +1 for the explainer video idea (hence my post from today)

    2. 1

      Thank you for the detailed feedback! Let me process it

  3. 1

    Your website is gorgeous. I love the combination of fonts and colours.
    I personally would prefer if you have a "try a demo" button where I can see how it works without signing up. If you have that, it can be the main CTA. And if I scroll a little too much it goes straight to the end of the page.
    I'm also not a big fan of the way the page scrolls, as it jumps to sections.

    1. 1

      Thank you! Yes, there are drawbacks with this design, but I guess this true on all full page scrolling solution.

  4. 1

    This is wonderful John, I'm glad you shared this.

    I resonate with the part where you invest a small fortune for something that might fail, but still prioritise happiness and adventure.

    I left my tech job to run my dream project a couple of years ago now, and I'm down a lot of money trying to make it work. But as long as I see progress and have a plan , I keep on pushing. That freedom is something else 😍

    Also, I'm glad to see someone else take the plunge and take real risk, instead of just running a side project that ends up going nowhere. Wrote about this here a few months back.

    1. 2

      Thank you! I read your post, it is great. Do you have a follow up post? I am very curious.

      1. 1

        Thanks I appreciate it! I sort of continued our story in this one.

  5. 1

    I wish you good luck, may I ask why the change of name? Coolboard seems to me easier to recall and less prone to be misspelled.

    1. 1

      Thank you! We changed the name because there is an unrelated company with the exact same name Coolboard - they building a balance-board. And there are two competitors with very similar names: Collaboard, and Collboard. So it seemed reasonable to change, also with riddey I could buy the .com domain which was not available for coolboard

      1. 1

        I supposed something along those lines was happening. Please keep us posted, it looks like an interesting project.

  6. 1

    Thanks for sharing! I totally agree with the sentiment to pursuit what makes you happy over economic intensives, I think that it is better on the long run.
    Good luck!

  7. 1

    Good luck on the journey. FYI: I am checking out your site and since I am a slow reader/scroller - your site is... really difficult for me. It keeps wanting to snap to a section, but I scroll only to part of the next section. The product looks interesting though.

    1. 1

      Thank you! Yes sometimes this full page scroll needs some adjustment from the users. I noted your feedback.

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