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sbilsteinHNSource author
Lessons learnedExperience excerpt · English

Oh absolutely

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! …

Original discussionI lost $209,640 of my own money trying to start a business224 source comments · at import
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JR
jrochkind1HN

So, if it's very hard to start a software company based on paying contractors for software development -- which seems true to me -- there's another warning here for software contractors/consultants . If someone is paying you, as contracting engineering talent for hire on a consulting/hourly/iteration basis, to develop an app or product they hope will be the foundation of a new business -- chances are high this won't actually work out for them (despite your competence and best efforts), and chances are high they will end up angry at you for taking so much of their money to develop something that didn't end up developing the business they wanted, with possibly legal action to try to claw back some of those funds. I have some personal observation of this. Even doing work agilely with review every two weeks and the client only paying once they've reviewed and approved the work in that two we…

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FL
flashgordonHN

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

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KE
kevstevHN

> 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.

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