How to Know if Your Startup has Gone Full Corporate

People often ask me, “Maboo, you had such a chill, cushy life over at Rap Genius - why did you have to blow it? You were eating all this free Whole Foods, you had investments from Ben Horowitz and Dan Gilbert and all these ballers - why couldn’t you simply keep your stupid mouth shut?!”

I often wonder about this myself, too. But the only thing I can come up with: I had an unconscious wish to leave Rap Genius at the time when I did. Things were getting too corporate for me. I started having to use gCal and fill out forms - it felt like I was in jail.

However, the changes in Rap Genius were in fact a necessary evil: my little baby had grown up, and I had to set it free. A self-perpetuating Rap Genius needed to have lots of rules - and I am not someone who can live with rules. To quote the famed philosopher Flea, I am a Nihilist, Lebowski: I believe in nothing. Even ISIS is too corporate for me, and I am basically the Persian Unabomber - I swear.

BUT… in those formative years at Rap Genius, I saw my cofounder Tom Lehman most artfully turn my energy into a company. Tom was basically my uterus: he gave Form to my Substance. And there were a few really important methods I saw him implement - although these were painful to me at the time, and ultimately I don’t understand them thaaat well, I thought I would share them in this article:

First, You Need An Org Chart

It’s one thing to say it, but do you know what this ACTUALLY means? It is not simply a chart with a list of everyone’s names. What org chart means is everyone actually needs to concentrate on performing a set function now. This is anathema to an early stage startup! In the early days of Rap Genius - I was doing whatever, and so was Ilan. Tom was a bit more focused because he was the only one who knows how to code - but then again, it’s insane how many different coding tasks he was performing at once!

Once you get an org chart, you can’t perform a variety of tasks even if you want to, because it will piss off other employees. I used to be the maitre’d of the Rap Genius party circuit. I threw some of the best startup ragers of all time, you should’ve been there! But once the company got the org chart, I wasn’t allowed to even pick the prosecco anymore, because the CFO’s (“Chief Fun Officer” - cute, right?) in charge of that were Jael and Ezra.

Org Charts basically mean the “Death of Fun” - it signals the death of the spontaneous creativity that is necessary to get a startup off the ground. But - alas - it is also necessary to do as your company begins to scale.

Next, You Need To Do Performance Reviews

In the early days of Rap Genius, when Tom and Ilan would give me feedback on my shit, I would usually tell them to fuck off. I am very sensitive to criticism, and I don’t want to improve - I’m happy just the way I am! This is why I don’t go to therapy even though my entire family has been begging me to go for years. Even if I ended up taking the criticism (which I usually did, believe it or not), I would do it several months down the line, hoping they had already given up hope and didn’t think their advice would be heeded.

It is because criticism is so annoying and hurtful that - as a company grows - it needs to be turned into a corporate shitshow. Even though turning it into a systematic thing might seem to make the process more painful, it in fact (counterintuitively) does the exact opposite. Because everybody knows that everyone else is going through the exact same shit, it makes the process a little bit more chill.

Furthermore, at least in the early days, I was trying my hardest. Maybe not everything I did was perfect, but my heart was in the right place. I was trying. This is no longer true when a company scales - as it grows, more and more people are perfectly happy to simply sit around and not do shit - and that’s the other big reason why performance reviews need to become systematized as you grow.

Last, You Need To Systematically Consult Investors

This third one is the most annoying one of all, especially because most tech investors don’t use the Internet. But as the company scales, you need cooperation of other dumbasses to make money (big corporations, for example), so your investors are just a sample of what is to come. You need to learn how to communicate with them.

One thing that I think makes Everipedia’s experience in MuckerLab more valuable than Rap Genius’ experience in Y Combinator is that the investors already sit down with us every week and give us feedback. They actually care, whereas in Y Combinator you simply feel like you’re at an amusement park - you get lost in the crowd.


UGH - I can’t believe I just wrote that! What have I become? I’m turning into the corporate goon I once loathed! I think it’s because I’m getting older - I’m almost 33 now, kids. Even though I will always stay true to the “Thug Life”, aging is kinda making me want to chill out and settle down.

For a startup to work, you need to have both the genius/vigor of youth as well as the restraint and corporatude of old age. One thing that’s turning me more corporate is that my cofounder’s for Everipedia are a lot younger than I am. They are like my sons. I feel like I have to set a good, corporate example for them. From Dadbod to you, here’s hoping my advice helps you turn more corporate, too.