Comment by graycat | Hacker News Reader

Comment by graycat | Hacker News Reader

IMHO, the OP is missing a big, huge point: He is really in the best position. So, here is what he should do:

Step 1: Create a small business. For this, he should pick a product or service that can be that of a significant business, e.g., the one he would like to manage as as technical CEO and where initially he can develop the product or service mostly just by programming on his own. Then from that product or service, get revenue.

Step 2: Be the CEO of the business, still just a one person startup except with as much outsourced as possible -- e.g., rented offices, bookkeeping, accounting, taxes, benefits, business insurance, legal, colocation or cloud for the server farm, consultants for specialized technical topics he is not already good at, etc.

Then as the first hire, hire an office manager later to grow to one of an administrative assistant, chief of staff, head of HR, or COO. Hire the product development staff and then the CIO to manage that staff. Hire a CFO, CMO, etc.

Then for this business, be the leader he wished he'd been in the past.

His abilities as a programmer let him do well in Step 1 and also be good at the technical parts of management in Step 2.

Step 3: Profit?

(Seriously, it is easier said than done. Do you know how many small businesses failed?)

Depends on how you define success and failure. I've had 7 failed startups (#8 is in the process of failing at the moment). I consider them all failures because I didn't end up with FU money. Funny thing is startup 6 & 7 really got me close.

Although, even if I won a billion dollar lottery, I'd still move on to startup #9. Half the fun is in the building anyway :-)

Agree that fun is in building the companies. But how long can you afford keep doing it (assuming you have family/commitment)? Success is what i call, you can keep doing what you like, not dependent on money, etc - iow, financial independence.

BTW, would be interesting to know the geographies of people who comment in this thread - say SF Bay Area, TX, MA, etc. That really adds new perspective to this discussion. My 2c.

I live in Oklahoma currently. I have done 5 of the startups in OK, one in CA (SF) and one in Texas.

You make choices in life and there are tradeoffs. I don't have kids nor do I anticipate having any. If they come, so be it. I partially left the Bay Area because I couldn't see even raising a hypothetical family there. That, the sticker shock never completely wore off and I never donned my rose colored glasses either :-)

I can afford to do it until the day I die. I've set myself up rather nicely in that regard. I'd be retired already if it weren't for my startups & first marriage. But being retired in your mid 30s sounds boring as well (I'm in my 40s now). However, I waffle on that position, so take it with a grain of salt.

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