Yeah, some of the recommendations are specific to his application and business, generalizing poorly to other startups.
For tech startups actually doing real tech development, like a new class of distributed database, the advice about (1) hiring freelancers and (2) needing front-end dev skills is obviously incorrect. Sometimes, the best first hire is a very senior software engineer that has the domain expertise and experience to lay the groundwork for a code base. The parts you can outsource effectively are the parts that are not core to your business success and you have to be able to identify which parts are which.
A first hire should be able to lead a role working on a core part of the business, whatever that business may be. The competent execution of the core part of the business will be a primary determinant of success.
there is also nothing wrong with hiring a friend in a funded tech startup (as employee #1). I'd actually recommend it, because you are still in that phase where you are looking for people to work with you and not for you. And just like when finding a co-founder, getting along with a person is very important.
I thought about this more after my comment. Yes, this is very true. Finding employee #1 is different from finding a co-founder but not by much, especially if you want them to stick around and work well with you. And founding a company with someone you are already friends with is I think much more common that founding with someone who you've just met.
Clearly you'll need both devs and designers. The theory behind hiring a good designer/frontend dev is that it'll allow you to iterate on UX much quicker, which is usually a bigger win for your customers.
Clearly this is generalized advice so take it with a grain of salt.
It might be a good idea in your blog posts to not write them as so absolute and more circumspect (for some of the points) since the devil is in the details for most things like this. And it's hard to cover all bases with the appropriate caveats in a short blog post.
Statements like this clearly indicate what has worked for you and are good "One thing that has always worked really well for me is to hire a freelance designer and developer to build the first version of the product." (helpful) while a statement like this is to absolute "I’d recommend your first employee should be a designer with strong frontend dev skills. Do not hire a customer support person." in part because there is no caveat as to which cases and types of startups this applies to. Good info though just something to think about.
For tech startups actually doing real tech development, like a new class of distributed database, the advice about (1) hiring freelancers and (2) needing front-end dev skills is obviously incorrect. Sometimes, the best first hire is a very senior software engineer that has the domain expertise and experience to lay the groundwork for a code base. The parts you can outsource effectively are the parts that are not core to your business success and you have to be able to identify which parts are which.
A first hire should be able to lead a role working on a core part of the business, whatever that business may be. The competent execution of the core part of the business will be a primary determinant of success.
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