[sbilstein]

Oh absolutely. Twice I made the mistake of coming onto a startup to fix the “mess” the previous dev shop had made.

Both times the founders had developed an incredibly negative relationship with their dev shop. Hell, the company with the Series A was withholding payments, the preseed company at least paid their bills.

I naively thought “of course they hate working with a dev shop, the incentives are wrong. I’m FTE with percentage points equity. I’ll fix it.”

Of course, things got better, but growth stalled or never happened, blame gets shifted, suddenly that founder who was excited to hire top tier talent is very disappointed in the very equity and salary expensive engineer you are. You end up being the new target of their animosity. You start to empathize with the folks in India, China, Ukraine or Argentina whose history lingers in the git blame. They’re not stupid, the incentives were just wrong!

The thing is…the CEO who failed to find a technical co-founder, retain them, or replace them with the same equity agreement has already demonstrated their inability to work with technical people. If they are coming from tech, the fact that they couldn’t convince a former colleague to work with them means they’ll be a terrible manager. If they come from finance, as many founders do, you are a line item.

At the end of this, hopefully sooner than later, you’ll quit, you’ll get fired, or you’ll collect paychecks while looking for the next better thing.

As an engineer, stay away from mediocre CEOs.

[kevstev]

> If they are coming from tech, the fact that they couldn’t convince a former colleague to work with them means they’ll be a terrible manager.

I kind of disagree here. I have been a manager at F*NG and just below those places in terms of pay, and getting my guys to jump to a startup without market fit, for the pay that those types of places tend to offer, I don't see how they would make the jump. The product/idea would have to be VERY enticing for this to happen, while for me personally, a CTO title would be enticing enough to maybe roll the dice on something.

[sbilstein]

Well, in this scenario, you are actually the 'former' colleague getting recruited to be a co-founder while the other folks stay stable. You just admitted you would and I wouldn't be surprised if there is a PM or even another engineer who would want to join forces. That's different than a complete stranger recruiting you -- I would be very wary.

[kevstev]

This was a real scenario I faced and the company/founder was a complete stranger to me- I forget if he just found me on LinkedIn or it was through angel list- I would not have been a cofounder just their CTO. Either way I ended up taking another offer with somewhat lower risk- they were extremely successful but turnover there was on the order of 25% per year. And I did end up taking some people with me and lasted about 5 years there so it all worked out.

I check in to see if the other company ever made it anywhere and nothing ever comes up so I guess I wasn't missing out on startup riches.

[flashgordon]

Great advice. Any guidance on asking the right questions as a way if filtering out these traits/behaviors in CEOs?

[sbilstein]

Be nice but remember you have objective skills and you need to suss out the CEOs objective skills.

1) Can they raise money? Proof is good here. Sometimes someone will say "I want you as my co-founder to go and raise my seed round" and you can condition leaving your current job on getting at least some checks in. Remember, this founder _knows_ you can deliver the goods, you are an employed software engineer. Can they?

2) Can they recruit? The process might be a mess but are they treating your time and concerns with respect?

3) Do they view you as an equal partner? Make sure you nail down exactly what they want. If they want a true co-founder, ask for 50%. If they don't, make sure you understand what it means to be an employee to a non-technical founding team.