How I arrived at TWiT.tv

The brief version (who knows, maybe a longer version later) of how I ended up at TWiT involves my Leo-fandom from The Screen Savers days followed by me relentlessly emailing the CEO asking for a position as a co-op through Northeastern. It took about a year, but I made it. I was expected to sit at the front desk, run errands etc… until I started automating processes and talking about the business side of things. My role evolved, and I had to go back to school… but still worked for TWiT. I was getting closer to graduating and knew they were interested in discussing a full-time gig. It was less money than I was hoping for, it was in Petaluma (which at the time I didn’t really mind) and I already knew what I was getting into organizationally… But it was TWiT, and it was Leo, and I was excited and optimistic and maybe a tad naive.

For that version of me, the dream job had been acquired. I was working on the business-side of a small internet media company whose focus was tech. I was going to build internal data systems and automation tools. It checked all the boxes.

But dreams change. Reality sets in. However you want to put it… the dream job was not really fulfilling the dream anymore. A question one must ask themselves is which of those actually happened? Did your dream change? Did reality set in? The first exemplifies personal growth or a change in interest. There’s no mistake to admit. But the second basically admits a personal flaw. Maybe you thought the job would be something else, maybe you forced yourself into thinking it was your dream, maybe it’s pride-related and you couldn’t admit to taking a job that wasn’t a dream job… Who wants to come to the realization that they settled?

For me, it was definitely a mixture, my dreams changed a little, but that was overshadowed by reality setting in. I will admit when I am wrong, and I was wrong. Things were great, until they weren’t. This was actually pretty soon, ~5 months at TWiT. There were ups and downs, periods of bliss, followed by periods of misery. It was only once the frequency of the latter outpaced the former that I knew it was really time for a change. So I emailed somebody I had a lot of respect for and I thought would be knowledgeable and helpful on the subject. I had a plan. I had to find a new job.

But what was the early 2015 Jeffrey’s dream job? It was still very similar, data-focused, internal, business-related. But I was at a crossroads: did I want to look at startups?, did I want to try again for the big tech-giants? Honestly the idea of a startup seemed less scary to me. Not from the career perspective, but from the idea of moving on. I’d tried for the big tech companies (Apple, Google, Facebook, Twitter etc…) — they didn’t want me. It could’ve been my resume, my background, my whatever… but my concern was that they’d reject me (again), I’d be in a slump, and I’d end up just giving up and staying at TWiT.

THEN MEERKAT HAPPENED.

I started meeting amazing people. I started being more open and public. I started sharing projects and ideas. I pretty much knew I wanted to work for a startup. A key driver in this was moving to SF, which I was going to do no matter what. It was an arduous process (hey, another topic for later!).

I spent weeks cultivating an audience and having fun while learning about the product deeply. In building MeerkatStats I learned the ins and outs of the data. I worked with the team, constantly providing feedback and support to the community. I knew it wasn’t my resume that’d land me a job anymore, it was my work and my actions.

So, I quit my job on a Monday, without a replacement lined up. I thought about consulting, trying to be be independent, but in the back of my mind I thought “hey, maybe Meerkat would hire me?” I knew I had to be free to find the next dream. Wednesday, I got a message asking me to come visit Meerkat on Friday and have a “conversation” with Sima Sistani (newly hired VP of Media at Meerkat)… that conversation really solidified that a role there would be a dream for me… I was fortunate that it ended like this:

Sima: “So do you wanna come work at Meerkat?” Jeffrey: “Absolutely!”

We shook hands and I had realized my next dream job had been found. It was mine. I was ecstatic. In watching me on Meerkat and seeing the work I’d done with MeerkatStats, she knew what she needed to know. I truly think I earned this role. I had put in the work to understand the product and built not only a reputation in the community but also a valuable product.

Am I saying Meerkat is the end-all, be-all for me? Absolutely not. I thought my role at TWiT was my dream job for a short while. Right now, I’m extremely thrilled to be doing something I love for a company I believe in.

‘Dream jobs’ are a fluid thing. I don’t really think there is any one way to determine where you want to end up in your career. You may have an inkling of an idea, but grasping it or pursuing it too narrowly can only cause you to miss potential opportunities that might come around. It’s important to keep an open mind, it’s important to be willing to take risks, and it’s important to find what motivates you at each stage in your life and career.