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> Sell something that sells. Sell what other people sell because that is what sells.

Agreed. I tried for ~3 years to sell ‘general development services’. Got tangled up in mobile apps, SharePoint, web development, basically anything that I didn’t consider to be “IT”.

It was a financial and professional disaster. The solutions all sucked, because I didn’t have deep expertise in anything and there was never enough budget to “do things right”. There was no opportunity to develop any kind of reputation for anything. It is insanely hard to sell “well, I can build things”.

As soon as I started focusing on a single, well-understood, boring business problem (“we need a good website”) everything changed. I started getting good at it, margins became healthy, referrals started to happen. Try getting a referral when the problems you solve are too vague to describe.

> There probably is someone who might buy that. You are unlikely to find that person because there are not enough days in the world for you to meet them and close the sale.

If there’s a market for CTO-as-a-service, or anything really, you need to be able to reach it. A hyper niche service can be OK if you can reach the people that need it. Broad markets can be just as hard because you tend to need to reach lots of people (think advertising). For me, the sweet spot turned out to be “small to mid-size regional companies” because you can identify them and sell to them as a freelancer.




^ There's nuggets of gold in this comment. I went through a very similar cycle. Learn from our mistakes friends!


Is this the nugget of gold? “As soon as I started focusing on a single, well-understood, boring business problem (“we need a good website”) everything changed.”


It’s the generalist vs. focused part. Many of us who have been successful in tech have done so because we are good generalists. But, that doesn’t transfer well as something that you can market. So there is great power in narrowly focusing on some skill that has demand you can meet.


It's also important to identify the thing that people request first, such as a good website. Plenty of work is done after that problem is solved or in addition to that problem.

The person who solves the "we need a website" problem gets to solve those additional problems if they want to.


That is a great point. Advertising as a generalist is hard because at the point a generalist is needed they already have a website and a developer.

You need to meet them at where they are, when they are in the market for a developer.


There is an entire industry of headhunters for stand-in for directors and senior staff.


What you are saying is gold and rings true for my experiences. Spot on.




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