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

#61
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…

Thanks for the feedback, I'll answer this by providing some more context. a) I've done well when you consider revenue/global brand reach/spread b) I've spoken informally to trusted board members nobody seems to have clarity on the best way forward c) Option 7 seems to be the best way out d) on point number 9, yes I'm distracted, but I've understated how much thought has gone into the second idea; it's something that'…

Interesting example with retail and CRM (called "point-of-sale" in retail, but I understand this is not your real product.)

You're right that POS is the #1 pain point retailers have, even though you used it only as an example.

I bring this up because the problem is not what you'd think it is.

You can't just "build another one and they will come", because each different business who might be a customer has slightly different needs and wishes to implement the software in a different manner.

For clarity's sake, we run 8 retail stores, and since I have a background in software my partner wanted me to build a POS, since none of them on the market met our needs. I know enough to stay far away from that gig, though, because it's a rabbit hole of custom engineering.

I don't know what your business is or what people have asked you to build, but if it's anything like what I described above, you'd essentially be downgrading yourself from "funded software company CEO" to "paid consultant."

And even if you think you can sell it with minimal modifications to other customers, you better be 101% sure of that before jumping off this cliff.

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

#64
post #45

Earlier quoted context omitted.

> unless you are Jack Dorsey I guess Well Twitter can't ship product, and many people within Twitter blame @jack. See for eg that article about the woman who setup their original abuse proceedures. Plenty of quotes in that which show how he stops anything getting fixed. Maybe Musk might be a better example.

Musk is not a good example. Tesla is in flames and there is worry it could affect SpaceX which is the more important company. The Boring Company also seems like a pivotal waste.

What flames? You cookin'? Last I read tesla is up for the quarter and the shorts are being squeezed.

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

#65
post #45

Earlier quoted context omitted.

> unless you are Jack Dorsey I guess Well Twitter can't ship product, and many people within Twitter blame @jack. See for eg that article about the woman who setup their original abuse proceedures. Plenty of quotes in that which show how he stops anything getting fixed. Maybe Musk might be a better example.

Musk is not a good example. Tesla is in flames and there is worry it could affect SpaceX which is the more important company. The Boring Company also seems like a pivotal waste.

I think Tesla is a big, risky bet. But he has delivered a lot more than Dorsey has.

Musk took over Tesla in 2008, which was two years later than Twitter was founded.

In that time Twitter has:

  Stopped crashing all the time

  Increased the Tweet size from 140 characters to 280 characters.
I'm no Musk apostle, but it seems to me he's done a bit more than that.

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

#67
If the new idea is sound and you've got others that believe in it, then go for it! Don't waste any time following a path, when you rather want to go another. Talk with the board and say you want to pivot, if they don't like it, then consider starting a new company, take the loyal people with you and offer them some equity.

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

#68
post #50

Having being a CEO for around 10 years singly mindedly focussed on a single company, I am coming around to the view that maybe running multiple companies is better. Though most people here would disgaree with me, and even me myself 5 years ago would have vehemently disagree with my current self, I am of the view that you should consider running both businesses. The critical insight that fosters this view is that afte…

What you have described is the serial entrepreneur model i.e. someone who founds companies, runs it past seed stage and leaves it to a professional CEO at the growth stage. I wouldn't call it "parallel".
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