Ask HN: Move to SF or Start a Lifestyle Biz?

10 points by anonbayarea ↗ HN
I'm in a mentally tricky situation. (1) I have an offer to join a Bay Area payments company (ex. Stripe, Square, etc.) I would earn ~200K/yr + 500K in units (over 4 years) but this is a fairly lateral career move for me. Moving to the Bay Area is the main appeal here (from Canada). I've already accepted the offer but having second thoughts.

(2) I've already resigned from my current job, where the comp was similar (but in CAD).

(3) My wife is on contract until Sept this year. I have a window from now until Sept to really try to start a lifestyle business. I would absolutely love this and if I didn't have an offer already I wouldn't have applied right now.

(4) After Sept our plan is to travel for ~6 months. If I move to the Bay, it would be pushed back a year or so.

(5) We're both 30, no kids, financially stable. Financially, doing my own startup wouldn't be a risk right now.

I'm struggling to justify the opportunity cost in either direction. I feel like if I reject this offer I may not see similar comp again (but that sounds silly as I even type it out). I also really want to move to LA in the future, not really the Bay but this felt like a step closer. It's worth mentioning that I work in Product (although have a CS degree). I've also started and sold a company before but that was VC-funded, not a lifestyle business.

Just looking for some opinions and guidance here. What would you do? I also understand how lucky I am to be in this position so am super grateful for that.

8 comments

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First congrats on being in a good position. It is awesome you have been able to accomplish it and still be only 30, you should be proud.

This is a tough choice, if you want to move, using the job offer to get you into the states, paying for relo etc seems like a smart idea IMO. Stay there for a year, gain some more contacts and friends in the area and work on your idea on the side a little. At least flush it out etc. You'll have to stay likely 1 yr to pay back your relo, but that would give you time to adjust after the move and do so on someone else's payroll. Then you can start your business.

If the idea is the business would be best kept in Canada than by all means it is doable to reject the offer after accepting but recognize it may shut that door for a while with that specific company (rarely for too long).

To be fair, I think you have a harder decision in many ways. It is very much so that when we are stable and things are going well that upsetting that can be the hardest. At the same time you are still in a really solid position as you don't have to worry about kids etc, so this is the time.

Guess I haven't been of much help, but the reality is no choice you make here is probably bad, you obviously understand the risks of being a founder so it is what do you want more?

Why not take the job, and start a lifestyle business simultaneously?

Lifestyle businesses (aka “small business”) are notoriously difficult to time. It may take you 6 months, 10 years, or something in between. You can also use some of your excess income to invest in the business.

If it turns out that your lifestyle business can’t support your lifestyle, and you have devoted several years to it, you will be in the position of having to go back to a “day job” with a big blank spot in your resume, as well as habits that aren’t suited to the corporate world.

You could consider giving yourself 3 months full time to launch it, then work part time on it after you take a new role.

Best of luck on your new adventure!

This is the exact advice I was going to give.

- Take the job in SF, you'll be a couple hour drive from LA

- Start working on a lifestyle business immediately

- Once you reach some initial traction (whenever that is) move to LA

Hang on a sec, it's more like a 4-5 hour drive. (I live in LA.)
One other thing to consider is the immigration aspect, since you're from Canada.

Will the new company sponsor your visa or apply for the employment based green-card? Visa can be tricky because you are generally tied to an employer, and it might be considerably more difficult to get permanent residency later on and takes a long time.

If they sponsor your green-card then that's a big benefit from the immigration stand-point, especially if you want to move to LA later on

What kind of lifestyle business are you looking to start? do you have experience in it? You could also look at buying business which would be a whole lot less risk.

Also, if its some kind of food thing just send me half your money now and you save yourself a lot of time and trouble. ;)

I think you should start a business and travel. Now is the time, it's going to be much harder later on when you're working full time. You won't be able to take the time off later...

You'll also be able to get another job no problem, go travel if it is important to you!

I see a lot of people suggesting that you both take the job and start the business at the same time. You really need to talk to a lawyer before you do that. Because of California law you would own your side project. However, depending on your visa you might run into problems with USCIS.