Brian Benitez


I've always fantasized about making my own company

How did you end up founding Collective Ray. Why do that and not join a company like Weebly or Facebook?

I started Collective Ray as a way to take on freelance projects with my good friend Josh Guffey just before moving to SF. When I moved, I joined Disqus and continued moonlighting CR.

Disqus was awesome and a great introduction to the whole startup scene—but I really wanted to learn everything I could, more so than just design, but also about how it relates to and empowers business.

For me, the best way I've been able to learn things is by throwing myself in the deep end and learning how to navigate it. So, we lined up enough business to sustain us for a few months and I bit the bullet and took the plunge.

That's wild. So you started Collective Ray outside of SF?

It was just a side thing back then, but yep!

Gotcha. Had you done freelance before?

Totally. That's how I'd gotten into product design—taking on freelance projects with whoever would give me work hah.

Freelance to me was always super weird. I always had a FT job and did freelance on the side, but never knew how much to charge, whether I should send them an actual invoice or what.

How did you figure it out?!

Yeah, sort of—really it was learning about how to run a business, how to try to grow a team and the impact of design on business.

I'm not sure I have figured it out!

Still learning everyday, I felt like I learned most of what I could within the context of running a small business, so it was time to change context and continue to learn (now it's things like navigating an organization, getting buy-in on concepts, how to communicate with a team and ensure good communication across departments).

We're in a very helpful (or at least it was very helpful) industry—I used to ask a lot of questions and people seemed happy to share what they knew. Connected with people at conferences and built relationships.

And a lot of googling haha

What about the lack of stable income. Was that ever an issue?

Fortunately, in lining up enough work before making the jump we were able to have regular payroll and thankfully were able to maintain it

That's such a scary jump, though!

It was scary—and strangely exciting

It never meant a sacrifice in life style for you?

Well, I basically had just moved to SF at that point—but no, luckily not really. I always knew I could jump out if it got too bad

I spoke at this conference in Florida a while ago, and in it there was this guy Taylor Pearson who wrote a book called The End of Jobs who argued that the most financially sound thing to do is start your own business.

That the 9-5 job is outdated now and it doesn't allow you to make as much money as you could if you used that time to make your own business

That may be true but potentially so much more volatile

What do you mean?

In terms of how well your business does from one year to the next. There will always be the risk of inconsistent revenue from one year to the next

But if you're able to maintain a steady baseline, and have payroll it pays off I guess

I didn't really make anything from the company other than regular payroll and benefits but just having that was enough to keep me doing it

Interesting. I usually think of totally selfish reasons for choosing a job so I'm curious how that changes when you have a family?

Yeah, life in general gets way more complex hah

Sometimes I have FOMO though, having a family so young

Was Erin a surprise or did you guys plan to have a family this young?

She was certainly a surprise

But once we were in it, it changes everything

how was that transition?

Did you feel "ready" at the time?

No haha

I still don't know what I'm doing

I just know it's changed my thinking

Given life purpose outside of "myself"

Oh man, tell me more

Outside of the same old cliché answers like having little people that came from you that now have to learn to navigate the world and you're their only guides, I don't have much

It's just one of those inexplicable things.

haha I guess that's why it's a cliché

Did you see yourself having kids one day?

Oh yeah, for sure.

when i was young i always planned on it some day

So I've been thinking about it quite a bit lately and what scares me the most is that there are *so many* things I don't understand about the world

Like I literally don't have an opinion on what's right or wrong for so many things

And I feel that I would be forced to make up my mind when I have a little person asking me how the world works

And that's kind of terrifying

I don't think that will ever change. We can only share what we know, and share how you process new things and your approach to figuring things out.

It is scary for sure

no families are perfect i don't think, i'm just always trying what i think is the best thing to do. i don't always get it right

sometimes, admittedly, i am selfish in some decisions

Parenting is kind of selfish in a way, right?

I mean, I don't know... clearly

but I imagine you inevitably teach a person how to be according to your standards


your standards are also your perspective

and that's one of the only things you can share

I imagine there comes a point where they will break free of your perspective and develop their own

which is terrifying because that's where there can be room for disappointment, right?


Theirs will be based on yours—whatever they agree with and whatever they don't

And that'll be their perspective

There was a time I was really disappointing to my parents

So that stage should be fun -_-

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Brian Benitez


Brian is a designer, father, and hip hop conosseur. He currently works at Weebly making the web more beautiful.

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