[zaidf]

Problem with that is most specialists suck or have very little interest in generalist work.

People became specialists because they particularly enjoy that kind of work. When you put them in an environment where things are changing rapidly, including their day to day nature of work, in my experience most specialists don't respond well to it.

I actually think hiring too many specialists is one of the biggest mistakes early stage startups can make.

[p4wnc6]

I agree specialists will not be satisfied with just doing generalist work without any other offsetting compensation, but this is why I said you have to pay them well and be very flexible about work style and work environment. You're already selecting for specialists who were open enough to the idea of working at a start-up that they even applied at all. That self-selects for some things, and an open mind towards generalist work is probably part of it. But just because they are open to the idea of sacrificing time they could otherwise have spent gaining more specialist experience in order to do early-on generalist work for your start-up, that doesn't mean they'll do it cheaply or be willing to fit into cultural situations they don't feel compatible with.

It's hard for me to believe most start-ups can really say anything conclusive about the quality of early-on specialists, because so few start-ups are willing to be flexible with office layouts, introvert v. extrovert working styles, and many other things. If a start-up is simultaneously rigid about those types of things and also claiming they can't get a good early-on specialist, well it's no surprise why they can't.

For legitimately cash-strapped start-ups, I think your point would hold true. Even if they are very flexible, they just won't be able to afford a good early-on specialist at all, even such a specialist who is already sympathetic to start-up lifestyle and willing to trade some salary for flexibility on certain working conditions won't go for it.

[pottereric]

The other factor to consider here is that not all specialists are focused on a technology. Some specialists focus on a process or a business domain. If a startup is working on financial software, finding someone that has a deep knowledge of finance software might be incredibly valuable. This could be very true if your software needs to meet regulatory requirements like Sarbanes Oxley.

[zaidf]

I assumed the context here was developers. For other kind of specialists, they can be INSANELY valuable from the get-go. In fact, one of the first hires I'd recommend anyone doing enterprise startup is hiring a domain specialist. These people are relatively inexpensive and add tremendous value in giving product feedback between early iterations. They can also talk to early customers with more credibility and thus help adoption of certain features that the customer may other not see much value in.

[pottereric]

Actually, I was talking about developers. In my experience working on projects that needed FDA part 11 compliance, it can be incredibly helpful to have developers that know how to write software that meets to compliance rules from process, validation, and auditability standpoints. I presume the same is true for SOX or HIPPA.