From Reddit Comment To A Job At A Funded Startup

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I consistently struggle with balancing my belief in the power of serendipity and my brain’s inherent need for strategic planning. It’s an epic, never-ending battle, one that pulls me in opposing directions on the daily. You could say my mind’s playing tricks on me. On the one hand, you simply can’t ignore the world’s seemingly random forces that create special alliances nobody would expect. And on the other, you have the hustler, grinding through carefully crafted plans to reach a predetermined goal. Every time I consider this topic, I’m reminded of how Steve Jobs approached the layout for Pixar’s headquarters.

The story goes like this: When Jobs was helping to design a new home office for Pixar, he apparently “obsessed” over the layout of the atrium, down to specific locations for bathrooms. Just part of his style-first ethos? Nope. He was optimizing physical space for serendipitous personal encounters amongst employees.


Here’s a quick review of how my last few projects, gigs, and startups came to be:

  • In reading through Medium, I stumbled across this post about “The Lonely Freelancers Club”, a weekly video chat designer Jehn Glynn implemented with her fellow freelancer friends simply to talk shop and stop working in their enclosed bubbles for a few minutes each week. As someone who worked from home for many years as both an agency employee and a freelancer, I had been thinking about this significant pain for a while. On a whim, I found Jehn’s email and sent her a note sharing similar sentiments. We ended up video chatting a few different times. Turns out we were both passionate about meaningful freelancer networking and we each had an interest in starting a side project. So we launched Collabo as a concept together. (It’s since been back-shelf’d as Jehn and I take on other projects, but it’s something we both still believe in big time.)
  • Like all good startup consultants, I’ve had a CoFoundersLab profile for a good year now. It was on there that Mike Hoy found me and asked to have a phone chat. He was looking for a marketing co-founder for IndieBundles and though I didn’t have the bandwidth at the time, we really hit it off and kept casually talking every few weeks. Mike eventually decided to kill IndieBundles and asked me for any last minute growth thoughts. We brainstormed a pivot concept – give the music away for free and focus on getting indie artists new fans – and it eventually became MusicBox, a startup we run together today.
  • Right when MusicBox started gaining some steam, I received a cold email from the founder of another NYC music startup, Audiokite, asking about potential partnerships. At that point I was taking any meetings I had time for, so I met with Alex at a coffee shop in Union Square. Even though there was no immediate need for a partnership, we met a couple more times just to talk music startup game. We vibed with each other, and quickly realized that the glaring needs each of our startups had were the exact skill sets we each owned. Alex is a brilliant product dev leader and I’m not too shabby at business development. Boom! We’ve been trading services ever since and both MusicBox and Audiokite have been doing very well because of this.
  • While I don’t spend a ton of time on Reddit’s r/startups, when I do drop in I look for legit questions and topics on which I can drop some knowledge. A little while back I ran across a great post asking for advice on what type of marketing person to hire at an early stage startup. I tried to share some practical advice (amidst a whole bunch of bullshit) and ended up direct messaging with one of the founders. Fast forward a few more phone conversations and a flight down to ATL and I’m now leading growth for Campus Bubble.

Steve Jobs wasn’t directly manufacturing serendipity, but he was building an environment conducive to its presence. Now, if all the Pixar employees moving through the atrium were heads-down 24/7, too busy with daily tasks to consider impromptu what-are-you-up-to’s, then the experiment would have failed. It’s on you to put yourself out there in order to woo Serendipity properly. Nobody gets a date by staying home; you gotta get out there and socialize, talk to people, take some chances. You never know when magic will happen.


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2 responses to From Reddit Comment To A Job At A Funded Startup

  1. Love this post. Reminds me of the concept of being “lucky” and how many entrepreneurs say you do need some luck, but you need to be there for when it shows up.

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