Ask HN: Successful web company founder/CEO looking for experienced advice

1 points by tempestn 11y ago ↗ HN

I run a successful small web-based company around classifieds search and aggregation. (I don't refer to it as a start-up since the goal has never been to get big and exit; we're bootstrapped into comfortable profitability and I'm happy to continue organically growing the business.)

I come from a tech background, and I've picked up a number of skills along the way related to the business side - everything from interviewing to accounting - but I expect I could benefit from talking to someone who has successfully navigated all of this before.

I won't get into all the specific questions I'm pondering here, but they are things like, for example, what's the best way to hire for positions where you yourself have little knowledge? I have no difficulty hiring developers, but I find the idea of hiring a dedicated marketing or sales person rather daunting. Or how best can you grow the business without growing your own workload proportionally? I know delegating is important, and I try to do as much of that as possible, but I find that while each new hire tends to increase our work capacity, it's more likely to slightly increase my workload than decrease it. I expect that's also related to only having hired developers so far. (Although compared to some of the horror stories you read around here, I have it really easy; I've very rarely had to put in the insane hours that seem so common in the world of startup founders.)

Anyway, if you think you might have some useful input and would like to chat, let me know! I appreciate it immensely. And of course, if you're reading this and think I might be able to help you, feel free to reach out for that too.

1 comment

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olegh123 11y ago ↗

>>but I find the idea of hiring a dedicated marketing or sales person rather daunting

Sure that makes sense. I think of it in terms of my goals. If possible I set up projects and staff those (rather than ongoing position). Main advantages are 1. clear goal. 2. clear end date. To control the project - create intermediate milestones to your goal.

Finally an analogy - if you're to hire contractors to work on your house (in area outs of your expertise) you'd collect bids for project, structure compensation in way that's tied to performance (no more than half before completion, bonuses). If cabinetmaker bungles some preliminary steps to building your kitchen you have leverage (a long the lines you dont get paid till completion/repair the demage -- whatever case may be). Hope that helps.