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Ask HN: I want to start a new company, but I'm CEO at a funded startup

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11–20 of 69 posts

Re: Ask HN: I want to start a new company, but I'm CEO at a funded startup

#11
If the business is growing fast, why bother about competitiveness?

If you switch to this new business idea, and you find another better idea again, how do you deal with that?

Big or smaller opportunities? How do you justify that?

Also, how long did you involve in the funded business?

Re: Ask HN: I want to start a new company, but I'm CEO at a funded startup

#12
post #2

(1) the grass is always greener on the other side (2) serial entrepreneurs are more common than parallel ones (3) don't you have a performance requirement with your investors? (4) does your shareholder agreement allow any of this? (5) have you talked this over with your investors? (6) it all depends on the cap table (7) you could always sell your stake in the current company or engineer an MBO (8) doing another compa…

Well phrased. Will just add at (2)...

(2) serial entrepreneurs are _more successful_ than parallel ones for the most part.

Re: Ask HN: I want to start a new company, but I'm CEO at a funded startup

#14
Most b2bs take 7-10 years to see through, with derisking inflection points at say 100k, 1m-3m, and 10m arr. So much matters in terms of valuation, kiss of death, etc, around those that generic advice seems unlikely.

It does sound like your heart isn't in it either way + it's early, so I worry for your team both if you stay OR leave. They are your bigger responsibility, so a transition discussion w cofounders seems like the real thing. But again... Vague. Good luck!

Re: Ask HN: I want to start a new company, but I'm CEO at a funded startup

#15
I don't see why your investors wouldn't be interested in pivoting the current company to a bigger opportunity with less competition. What are the objections going to be? They are not going to get mad at you for finding a bigger opportunity when you were out talking to customers.

Re: Ask HN: I want to start a new company, but I'm CEO at a funded startup

#17
Do NOT mix the companies up. Corporations were invented specifically to separate unrelated concerns.

You are not enslaved. You can move on. It will just look irresponsible.

Just be responsible.

Also startups and marriage are the same in so many ways. If one is having a seven year itch the reason is not the spouse but a fear of commitment.

Dance with the one that brung ya.

Re: Ask HN: I want to start a new company, but I'm CEO at a funded startup

#19
Don't ask us - ask your board. Clearly they already have confidence in you, this opportunity came from your current work, and you would need capital anyway. So see if they will fund/find investors for it, whether they agree it should be separate, and see which effort they want you to lead. Maybe they will surprise you and let you run with the new thing, and bring someone new up to your current CEO role.

Re: Ask HN: I want to start a new company, but I'm CEO at a funded startup

#20
post #2

(1) the grass is always greener on the other side (2) serial entrepreneurs are more common than parallel ones (3) don't you have a performance requirement with your investors? (4) does your shareholder agreement allow any of this? (5) have you talked this over with your investors? (6) it all depends on the cap table (7) you could always sell your stake in the current company or engineer an MBO (8) doing another compa…

(11) Ambition is the enemy of consistency

beware

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