
Ask HN: Did anybody bootstrap a successful business by hiring a freelancer? - danr4
How would you rate your experience?
======
danieltillett
I have hired a lot of freelancers over the years and I run a successful
bootstrapped business. I don't outsource core activities, just smallish things
that we don't have skills in house to do. Overall it is hit and miss, but my
advice for what it is worth.

1\. Only hire individuals. Never hire a team.

2\. Watch out for individuals who are secretly fronting a team.

3\. Make sure that you have a keyword in your project description that has to
be mentioned in the bid by the freelancer. This will allow you to weed out 95%
of freelancers who bid without reading.

4\. Chat to the freelancer about the project first and if possible hire them
for a small private project to scope out the details.

5\. Despite all these steps expect only 50% of freelancers to workout. Either
hire two at once or schedule enough time to do it sequencially.

~~~
crystalPalace
As someone who works on a freelance team, why do you only hire individuals?

~~~
danieltillett
A few of reasons

1\. It is very hard to pin down who is responsible for anything.

2\. You end up explaining everything twice - once to your front wo/man contact
and then again to the clueless intern who is tasked with implementing what you
want.

3\. It is near impossible to determine the competency of the person who will
be doing the work in advance. The front person is usually quite good, but the
person who actually does the work is often not. You can’t work that out until
you are well into the project.

Teams on average are probably better than individuals, but from a project
management perspective they are a pain to deal with.

~~~
crystalPalace
Here are my personal anecdotes:

>1\. It is very hard to pin down who is responsible for anything.

Fair for some situations but my team and I use git and share the repo with our
clients so they can see who is committing code.

>2\. You end up explaining everything twice - once to your front wo/man
contact and then again to the clueless intern who is tasked with implementing
what you want.

My team and I always make sure we are in the same email thread with the
client.

>3\. It is near impossible to determine the competency of the person who will
be doing the work in advance. The front person is usually quite good, but the
person who actually does the work is often not. You can’t work that out until
you are well into the project.

I've had situations were my entire team has interviewed separately but I can
see how this is unfeasible for some teams especially past a certain size.

~~~
danieltillett
I am sure there are good teams (and you sound like you are part of one), it is
just really hard to work out who is a good team and who is not until you are
well into the project.

I think if you had a really large project then a team would be a good idea
especially if you require skills in a lot of different areas, but in my case
all my projects have been smallish and focused.

I have worked with some amazing freelancers over the years who can do things
in days that would have taken me months.

------
wayn3
I helped someone non-technical hire a competent freelancer. works just fine.

the problem is usually in the skill of the freelancer, not the fact that
freelancers dont work period.

if you need a website and a stripe integration, then thats all you need. you
dont need someone "oh my god fully committed to the business".

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sheraz
I'm bootstrapping a couple of side-projects by training up an intern, and
starting in January I will be paying him a monthly retainer against hours
worked. The coming tasks will include:

\- Stripe payment integration \- Marketing automation

This has been a great experience for both of us, and we will be self-
publishing a PDF book on this process.

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taphangum
I basically built MyAppTemplates.com off of Elance. IMO the key thing was in
working with freelancers who 1. Were very responsive by email and 2. Didn't
need a lot of explaining in order to 'get it'.

This apart from the obvious requisite skills necessary to do whatever the job
was ofcourse.

------
arielm
We've been bootstrapping (successfully) for a few years now and so far almost
every instance of using a freelancer failed (some more miserable than other)
and cost us money and time.

We're in a unique situation where we outsourced for lack of time and not
skill, which is a double edged sword...

My two cents - if you can do it then do it. If you can't, and can't learn fast
enough, then try to freelance it.

