Direct to Entrepreneurship vs Traditional Job Path

I think a lot of early career engineers are seeing peers jumping into entrepreneurship and making a big and flashy impression (likely through LinkedIn). These impressions are surface level and I highly doubt these peers are going to be honest about their current situation. This is to hold up an illusion of success when reality is likely much more stark and harsh. No one's going to be jealous of someone living of discount ramen from Walmart, so why post it?

Honestly for junior engineers, there are 2 general truths.

• They can't do anything meaningful. Internships, clubs, etc. build experience, but that experience isn't deep since the durations of those efforts are short and shallow. To build something, you must understand something deeply. If you have not understand something deeply, how will you be able to build a solution for it that people need? And if you need the company to make money, that just increases the activation energy for success 100x.
• They don't know how to work with people. Similar to experience + expertise above, it takes a long time (more than however many months spent on a club or internship) to have a relationship with people. At some point, you need to interact with people: a potential cofounder, a potential customer, a VC. If you (in your current state) try to reach out to the people that will move your company forward (even with the best idea in the world on hand), nearly all of them will ignore you. And you will have no idea why.

I'd recommend that you should just work both a standard tech job and doing your entreprenurial work on the side. Your day job will set up foundations of people you can interact with and potential build deep relationships in, give you a baseline of code to write and some structure for you to improve, and work experience to make your background look stronger. You can pull in your learnings about software into your soon-to-be startup & you have a pool of coworkers that could be a potential customer/cofounder or potentially route you to someone who can help you.

There's also nothing stopping you just finding a job that better aligns with your goals (joining a smaller company) or just shifting your behaviors at work to better align with your goals. My very hot take here is that the folks (working a decently sized company) who are complaining about their work not aliging with their goals just have skill issues & don't want to admit it.

You have no idea how much pain running a startup can bring. It really can be like having broken glass for breakfast every single morning.

I think the premise of your questions should be different. Life is a marathon. Instead of jumping the gun and trying to learn everything at once, why not learn aggressively at a sustainable rate? Most of the time, the way to do this is to get a hybrid/on-site SWE job and moonlight on the side. Then, you can go 100% remote for even more freedom. Then, you can quit your job once the startup makes $10-20k USD/month.

I know you have this patience: you stuck around for a CS degree. But going 5 years at full speed doesn't do you any good if it requires 2 years of therapy to recover.

I quit my very well-paid "traditional" tech job to do Taro, so I'll chime in with a couple thoughts for consideration:

• Doing a startup is hard - It is almost always harder than people think it will be. I knew it would be hard going in, and getting Taro off the ground was still 2x harder than what I thought it would be. The vast majority of engineers, especially juniors, are already struggling to do the engineering part right. As a founder, you need to also be a product manager, designer, data scientist, salesperson, and so much more. These are all disciplines that normally take years to master.
• You (probably) need a cofounder - I seriously don't know what I would do without Rahul by my side, and I'm sure he would say the same for me. Yes, solo founders exist and are successful, but they are the exception, not the rule. Only ~5% of our YC batch was solo founders. Being a founder is such a slog, and the emotional toll is near impossible to bear by yourself.
• Startups only produce learning if you find some traction - This is because you can't really be learning much when you are dead, and making your startup not just flounder and die is already a tall order. It's true that startups teach you way more than any "traditional" tech job, even FAANG (this is something I have said many times and experienced myself), but the caveat is that the startup needs to have some sort of momentum to draft off of. If you spend 1 year agonizingly pivoting 5 times and failing to find any semblance of product-market-fit, you probably would have learned more working at Google or whatever.

So, if you do not have a income source or financial stability, going Entrepreneurship will mean you have to rush, and so not make anything that can really stand out. Also the pressure of paying bills and eating/having a roof over your head will not allow you to focus of what you are trying to create. That is not a good place to be.

Also you need a lot of skills to run a company, and also to create the MVP of the product, sell it before you can hire others.

If I were you, I would take it a bit more slow. Get 2-3 years of industry experience first and then seriously pursue the startup route. If you can find a job with solid work-life balance, you can hedge and build side projects that hopefully blow up like mine did, opening up a very organic path to creating a startup.

There are many benefits of getting the work experience first, especially at a top company:

• Your skills improve - People skills, technical skills, product direction skills (if you work at the right company): There are so many things that working at an already established company helps you with.
• You create a financial foundation - If you're single, you can save a lot of the money and throw it into index funds (ideally American ones). The US stock market is white hot right now, and I don't see that stopping. You can reap a lot of gains across 2-3 years.
• You build a network to find a cofounder(s) - Coworkers are the best cofounders as you know that you work well together and how to synergize.
• You get clout - Clout is helpful in many ways, but tactically, it will help a lot with fundraising. For example, if you're a Google MLE, you are going to have a 5x easier time raising money for your AI startup compared to an MLE that worked for no-name companies.

In terms of company to work for, I recommend working for a top unicorn like Notion. At these companies, you will still get the startup vibe, but you also get the high pay and prestige for your resume/founder profile. If you can't get into a top unicorn, FAANG is also pretty good, especially Meta (with Google being a respectable 2nd IMHO).

Particularly interested in hearing from people who've successfully made the transition from corporate to entrepreneurship - what would you do differently if starting over?

I would have started sooner. As I mentioned before, I think 2-3 years is a good foundation. It only gets harder to start a company as you age (it's still possible, just hard), so you want to do it when you're very young and have more energy. In a vacuum, I wish I could have started with 5-6 years of industry experience instead of 8.

I recommend checking out this playlist too: [Taro Top 10] Entrepreneurship And Tech Startups