How Freestyle Rap Can Make You Better at Life; 6 Things I Learned at a Rap/Tech Startup

Randa Sakallah
5 min readAug 6, 2013

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Ever wonder what would happen if you put a white girl in Detroit at a freestyle rap startup? Let’s just say you can now refer to me as Randa Tha Rhyma. How freestyling is relevant to life and more things I learned at rapt.fm below.

1. Stalk your audience. Show up at every place they’re at. (On the internet, that is.)

Growth hacking was one of my responsibilities this summer, and I learned very quickly that getting your first users is not easy. Whoever said, “If you build it, they will come” was a blatant liar (I just googled it and it was some ghost in a Kevin Costner film. Figures.) It took some guerrilla marketing and creative thinking, but we did it. Some of my user acquisition techniques included but were not limited to:

Posting clever YouTube comments

Editing WikiHow pages

Creating an alter ego

This general principle can be applied to any business or organization you’re trying to grow. Try EVERYTHING you possibly can to draw people. After all, when you’re just starting you don’t have much to lose (your internet dignity is not your real dignity).

2. Your first users are your most important users. Befriend them. Learn about them. Show them you care.

Rapt.fm had just launched a testable version of the site when I joined the team. We connected with each and every user that signed onto the site, and made sure they were having a good experience. If they were unhappy, we found out why and made sure they knew we were making an effort to fix it—turning frustration into gratitude, one rapper at a time. Your first users are the best evangelists you’ll ever have, and they “should feel that signing up with you was one of the best choices they ever made” (Shoutout to Paul Graham). As you might have imagined, I also made some friends.

Interesting fits better than awesome. Gonna remember that one.

3. Learn the lingo of all parties involved.

Working at rapt.fm involved communicating with a bunch of different people—investors, writers, and users, to name a few. Talking to each group required certain vocabularies, and I wasn’t well acquainted with any of them. Nothing compares to working in a place where you’re surrounded by startups and venture capitalists. I can assure you that you’ll get absolutely nothing out of an investor meeting if you can’t keep up with the lingo. Thanks to asking lots of questions I now know what it means to use a CRM tool, find an angel investor on AngelList, and manage my web presence with SEO.

As for the users, I had to keep up with the hip-hop slang to communicate effectively (and look cool). I knew a couple words, but found myself furiously urban dictionary-ing and can now proudly say I know that “yay” is slang for cocaine, getting “daps” is a good thing, and if someone says “stamp” they’re really just saying “ok” with an exclamation point or two.

4. Earn trust and build a friendship before asking someone to do something for you.

Don’t tell someone what to do unless you’re a) paying them or b) you’ve built some social rapport. Plenty of people said the site was the “greatest idea ever” and they wanted to “be a part of it”. We took this as an opportunity to build a promoter system. To get the word out, I tried the tactic illustrated in slide 10 here, and for the record, way less than 90% of the promoters filled out the spreadsheet. I thought their interest in the product would be enough to motivate them, but after several iterations of the promoter system, I learned something. It wasn’t their interest in the product that would make the system successful; it was my interest in them.

5. Sales isn’t about being a robot, it’s about being human.

I saw sales as an opportunity to improve my conversation skills and train myself to speak clearly. I thought I was going to have to memorize some kind of script and practice my intonation and stuff. This turned out to be mostly wrong. I do tend to speak quietly and trail off, which with the guidance of a few good people, I learned that no matter what I say, I sound something like “I am an unconfident piece of shit who hates myself and everything around me. Don’t buy my product. It sucks. Just like me.” After fixing that, I started making calls, and actually found that calls went much better when I skipped the script and just talked to the customer like I would to a friend. Not like my best friend, more like that one friend that I still crack jokes with but around whom I avoid saying anything that isn’t politically correct. Anyway, being yourself (your knowledgeable and enthusiastic self) is how you make a sale. Knowing how to navigate LinkedIn to find the people you’re calling and having patience with automated telephone operators also helps.

6. Freestyle rapping has useful real-life applications.

I’m not referring to looking cool at parties. The first time I tried freestyling was on rapt.fm before I worked on the site. I heard about it in an MPowered meeting, and decided I’d check it out. In an effort to disguise myself, I wore a beanie and some aviators, grabbed some friends for support, and signed on. I was absolutely awful at rapping, but enjoyed it. I kept at it and here I am, 6 months later, signed to a major record label and in negotiations with NBC for my own talk show. Okay, maybe not, but that’s not the point—freestyling is not only a form of creativity that stimulates a certain part of your brain but it also builds confidence and allows you to express yourself, unfiltered, without caring what other people think.

I did improve though, in case you’re wondering. No tracks or shows anytime soon, but if you see me around I’ll gladly spit a couple bars. Randa Tha Rhyma lives on.

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Randa Sakallah

University of Michigan CS grad. Formerly at Spotify, True Ventures. All life success attributed to playing Neopets.