Year off of school vs. starting a company

I'm also a sophomore (in CS) at Berkeley. My background is a bit similar - I took a year off before college to take a software course and work at a startup. The year I took off was probably one of the periods of greatest personal growth I've ever had in my life. I learned a lot technically, but that wasn't the most important thing I gained (or even the second or third-most important thing). The most important things I gained were friendships and connections with people older than me, and greater perspective on my goals and on college. I like to think I'm a bit more street-smart than I used to be, having been exposed to the real world. It's important to note that taking income minus taxes/expenses, I earned next to nothing over the course of that year (and have a bit of stock that isn't worth much even if the startup continues to do well), so I gained nothing financially.

I don't put much faith in the arguments that "you'll never go back" if you take a year off - I did, and when I made the decision to go back, it was precisely that - a conscious decision, rather than how most students go to college (which is by following the default path). At any time, the decision is yours to return to college - if you decide not to return to school it will only be because you judge your current opportunity (the startup or wherever your career takes you) to be better than going to school.

Obviously the details of this opportunity are pretty important - how much equity are you getting? How much control? Who do you get to work with (the people you meet and/or work with is probably the single greatest factor in your early career)? How much funding do you get? How flexible is the parent company in letting you make decisions (remembering that if you don't have >50% of the equity, they have final say in all decisions)?

If you want to take this offline, my email is in my profile. I wouldn't be so quick to dismiss an opportunity like this. If you think your skills are up to it, it's worth considering. At the very least, I would take the trip to Japan, and come prepared with tough questions for the executives (questions about control, autonomy, flexibility, the conditions of funding, how they make decisions, their philosophy around product management, etc.)

Thanks for the reply! I would appreciate talking to you; I can't seem to find your email in your profile however. I was going to ask you anyways what other questions you would ask? I really have no experience with regards to many of the business side and harder questions you have proposed. What critical points besides equity and funding should I look at?

I just finished grad school and undergrad right before that (I lumped them together in 4 years; not to brag, this matters for what I'm about to say). I spent most of undergrad tempted by a few nibbles to take a gap semester or year and see what happens. The way I see it (and others on here may disagree with me), you should stay in school unless the golden opportunity comes along. Here's why: you are earning your education at one of the top schools in the world for EECS. You, provided you don't screw up, will have any number of opportunities post-graduation that others won't have, especially when it comes to startups. I graduated in 5 semesters from undergrad because I wanted to 1) go deeper into a technical background (undergrad in information systems / business - yes, I'm from "the dark side") during grad school 2) work for a startup

I chose to go to grad school, and along the way wound up working for a healthcare informatics startup. Great team, I trusted them a lot, even when they had a major product pivot. Last fall, I had to make the choice, wait for a spring offer to join them full time (yes, please and thank you) and reject other fall offers, or "play it safe." I took the handshake agreement and it wound up falling through. Am I pissed? Yes. Am I glad it happened? Well, I got a great learning lesson out of it, and am now doing my own startup in data analytics, commercializing a side project I did during grad school.

What I'm trying to get at is that yes, you will always regret the "what ifs?" However, be rational about the team, the product, and the vision, and the opportunity cost of putting your education on hold. Yes, you can always go back, but I've had friends do it, and it is hard(er). I'm happy to talk more about this or follow-up, since I know from semi-first-hand experience a bit of what you're going through. You have a lot of options on the table, but just look long-term and be true to yourself, more than anything else.

I've sent you an email. I would like to talk about this some more, thanks for replying.

Background: Did my Bachelor's in EECS at Berkeley, and I've lived in Japan for longer periods of time (including startup-related stuff). I would claim to understand the Japanese culture and work environment pretty well.

I a huge advocate of taking time off (whenever, before college, after college, during college), and I believe that starting a company or building a product is one of the best ways to spend that time. I have taken time off multiple times and looking back it has always been the best decision/experience. HOWEVER, I would be wary of this particular opportunity as, from what it sounds like, it probably won't pan out as you imagine. It sounds a bit fishy.

Just some thoughts:

- Take a very good look at the exact terms and make sure they are not using you as cheap labor. "Get some equity" sounds as if you will be working 80h/week (typical for a founder), not getting paid very much, and not even receiving a large portion of equity. Do they want you to recruit other people? How so?

- This is a generalization (but still applicable in 98% of all cases): Japanese companies are extremely bureaucratic, very old-fashioned, and you will most likely have much less freedom that you currently think you will. A lot of your work will consist of doing fake work (reports, spreadsheets, etc) to fulfill some bureaucratic requirements (typical for all Japanese companies) as opposed to being actually productive.

I'm also happy to talk offline, see profile.

Hey, I've replied to you as well. Thanks for the insight, a lot of people are warning me to be cautious and I was definitely wary of this offer from the start.

A few things to think about:

1. Everything is negotiable, try to work it in your favor to not have to choose. If your going to lead a company, negotiation is a good skill to pick up.

2. I have always felt there is far too much anxiety around technology/startups ... will it be there when I arrive? Will I still be relevant? Urgency is great when you jump in, but rest assure it will be here when you come back, if you choose to take the time off.

3. Do you want to run from regret or follow your heart?

4. Put your degree as a priority unless you are absolutely passionate about what you are postponing it for. As a 30 year old drop-out, sure it's nice when you have money to walk around and look like a genius because your successful, but it brings on additional insecurity and uncertainty when you do not have that paper behind your name on the way up. How much time do you spend climbing vs. time spent at the peak? Prepare yourself for the climb.

5. Take the trip, discuss your flexibility, listen to the idea, take time to evaluate. When an idea connects with you, the question changes from "what should i do?" to "how do i make this happen?"

Lot's of great advice from the others also. Good luck none the less, you have two really exciting paths in front of you, so its already a win-win.

Do neither. Stay in school. If you leave, you'll never go back. (trust me, this happens 99% of the time when people leave school) You can take a year off after you graduate. And job opportunities come and go. This one certainly doesn't sound like you're getting in on the ground floor of something great.

Ok, I realize it is cool now to tell everyone on the internet your business...but what you have written here could be interpreted as suggesting that this company is stupid for "dumping money into me when I have no product, no team, and no background experience." You are doing this in a post on Hacker News...which many, many, many people read.

Why are you sharing the exact names of both the company and the startup you work for? Do you think that some of the people at those companies may not read Hacker News?

Do yourself a favor and scrub this article of references to who you are talking about before you ruin this opportunity for yourself. If they believe you are someone who posts all their business dealings on the internet for everyone to see, they are not going to want to fund you anymore.

Thanks for the reply. I put up the names in case anyone had experience with them or was able to find more information on them than I could. I don't know the parent company very well (hopefully I will soon), but they've given me much more important information than this that they've told me not to disclose and I haven't. In hindsight, it was probably better not to include the company names, but I can't edit my post anymore. Lesson learned.

Since you're directly asking for advice: no. Finish school as planned (earlier? awesome). There will be plenty of opportunities ahead. Don't set yourself on a path of failure because startups are very risky, these guys have no experience funding them and it seems like you're a technical guy having lots of fun (but are you an entrepreneur at heart?). Think about the odds of "startup being a success, in your perspective" vs "startup failing and I still haven't finished my studies". Just my 2 cents.

People invest in individuals they know and trust. So you're Johnny-On-The-Spot for this deal. No need to drop out of school completely. Try a semester with an extra light course load. Be upfront, let them know that you'll need some schedule flexibility. Moving forward, do get your agreement and action plans buttoned-up on paper. This will increase your odds of success.