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Yes. You need a clear focus and direction. Although a 3-6 months break is more than enough to find out if you want to start a company or just want “more” free time to experiment with technology ideas. I think I am more in the second camp.


I left the same company after 5+ years ( 6 years ago ) with a few goals -

1. Spend time with family ( parents )

2. Work on a side project

3. Travel

4. New language ( Spanish )

5. Learn something new ( tech and non tech )

I am very happy with 1,3,4,5. ( ongoing )

Regarding 2, I worked on making a no code platform for Voice apps and had a working demo/app but the market was just not ready and it still is not … Next I tried making some simple web apps - but no success financially. I keep on experimenting with technology so I still love my current state of affairs.

My personal learnings/experience (also from YC Startup School online ) is that you need to have some form of demand/audience before building the product for the consumer space. My friends in the Enterprise space seem to have much better luck.

PS: The fruit company is pretty strict about moon lighting (speaking from experience of a very good friend ) so just be careful about that aspect if they find that out while you are employed. I left in positive terms, in-fact a week back my boss mentioned to let them know when I am done with everything and would like to be back.


Thank you for sharing your story! Have a couple of questions, if you don’t mind sharing a bit more: 1. How are you supporting yourself financially? Are you consulting or living off you savings? 2. Based on your friend’s story, do you have any tips on what not to do when trying to moonlight?


1. I am primarily living off my savings. However, I haven’t had to sell any investments for expenses during this period and they have likely grown ( as per Mint.com ) I don’t actively track my investments ( I have vested stock from the fruit company + use robo investing ) so I am mentally free to enjoy other things without worrying about market volatility … I think my average monthly expense ranges from $1500 - $2500 depending on the country. A lot cheaper than a Bay Area down payment + plus so much time to do anything. Also unmarried and no kids.

2. My friend ( at Fruit Inc ) was working with a undergrad friend from the East coast on a side project. The other friend posted a Craigslist ad needing help on the project and mentioned my friends credentials on the posting. Somehow a recruiter found out about it and so my friends VP called him … that he can’t do so and so, and that the fruit company owes everything and he needs to turn it all to them, and he can be terminated etc. And even after termination they will come after him. Long story short, he stopped working on the project and he was NOT terminated but he did eventually leave to a different company. (For context: the project my friend was moonlighting on was not some cutting edge secret or some hard problem )

Bottom line: If no one knows about your project you are fine. And if you decide to leave the company and work on your idea … might make sense to ensure that the start date of the code etc looks a little after your resignation.

Happy to answer if you have any other questions


Thank you for such a detailed response - really appreciate it!


regarding (2) did this happen recently? or years ago? I've heard the culture or policy around this has "changed" but that could all be BS.


If you remember Flipboard, Evan Doll was in the iOS team and also taught the CS183 at Stanford. As per his LinkedIn as soon as he left, the same month he cofounded Flipboard although the app was released 1 year later.

I have a few coworkers from my team that cofounded companies and they too have 1-2 month gap after they quit and they all got funding :)


It was around 2011.

I don’t think the policy changed as per se. It’s just they found proof of him trying to hire a part time help.

I had a co-worker around 2013 ish who just wanted to blog and put personal projects code to GitHub. It was not recommended and needed VP permission … basically a hassle.


i wonder how this stuff is dealt with during hiring conversations like when you have a project already …. or how acquihires happen


I had no idea either and had a similar visual image of @dang. I just had to google and find his full name and a picture to put a face to the name :)


> and a picture

I thought it was the only picture not published on YC and kept private.


It’s worth learning as an important CS concept, as it can be intuitive to express an idea and understand the algorithm on a conceptual level. Although implementing recursion can sometimes feel very confusing, apart from the fact that you might also hit a stack overflow and it runs slower than an iterative solution.

In fact, a few days ago I implemented a flood fill algorithm for a drawing app I am developing. I later converted it to an iterative solution. Here’s a comparison between the two solutions

https://zkpunk-xyz.vercel.app/posts/recursion_vs_iterative/


Paul Hudson has an amazing library of content at his website/YT for 100 days of Swift, and SwiftUI online for free.

https://www.hackingwithswift.com/100


Blockchain technology helps you create applications without the need to have a trusted 3rd party.

What it solves?:

- Sending money from Alice to Bob without the need of a trusted party like Venmo/Paypal/Bank.

- Vehicle registration / House title deeds are maintained by the local government. A decentralized application can potentially mint an NFT (ERC-721) and maintain such a DB. (Although, the physical society would need to come with laws to tie up physical good's with NFT's)

- In today's Gaming Economy all the digital goods bought/earned are controlled by the company (Zynga/Roblox). A blockchain powered game will allow the owners to have actual control of the digital goods ( money - tokens, wearables - NFT's) bought/purchased that they can sell/exchange in the open market. Imagine buying a souvenir from Disney Land and then not being able to sell/exchange it.


In my opinion, none of those things are real problems that need solving. They’re fabricated to fit a technology.


I don't subscribe to Netflix because I'm not entertained by such things. That doesn't mean others don't have a need for low-cost narrative diversion.

The fact that you don't acutely feel the need for a trustless digital money is very telling of your position in the world. I would recommend you read the book "Check Your Financial Privilege", by Alex Gladstein. You will find that, as an absolute fact, the use case is in extremely dire need of solving, and Bitcoin is the solution.


It's a huge space and I got into it around Feb/March of 2021. Some interesting applications I noticed are:

1. Lending Apps - A trusted decentralized application to deposit collateral and earn more interest than a traditional bank. And then use the same application to take a loan on the basis of the deposited collateral. Example Apps: Compound / AAVE / TraderJoe.xyz to name a few

2. Exchange Tokens - A simple application to swap between two tokens (ERC-20). Example: Uniswap, QuickSwap, etc

3. Ownership of digital goods - Imagine if all the digital goods someone owned in Farmville could be sold, traded, exchanged. All of this is possible due to NFT's - ERC 721 Standard Example: Aavegotchi, Axie Infinity, etc

Interesting research is happening in the field of cryptography - Zero Knowledge Proofs, Verkle Trees. Foundations/Companies: Matterlabs, Arbitrum, Optimism, Polygon

A lot of work is happening in app development tooling: Solidity, Ganache, Brownie, etc


Infact, the Spanish built a temple on a hill in Cholula only to be discovered that it was actually a Pyramid!

https://en.m.wikipedia.org/wiki/Great_Pyramid_of_Cholula


Actually I am currently not looking as I am backpacking :)

I am just exploring the OpenCV library for fun things to do and in the process documenting simpler and smaller stuff for my reference. I do plan to have a follow up post that will automatically find the corners!


Yes, Indeed that’s the direction I am heading towards, but I am initially starting with simple posts to keep the flow ( for myself) and also easier for people to notice the simplicity of openCV.


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