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Chiefs of Staff Living in a Not Boring world

Chiefs of Staff Living in a Not Boring world
Please see the following summary of the core ideas from this conversation at the Summit. We did our best to clarify the ideas for you. Please refer to the video for specific details, ideas, and context.

Tell us about the middle steps between starting the Not Boring Newsletter and where the newsletter and your company is now:

Packy: I spent 2019-2020 trying to leave Breather and wanted to find new hobbies outside of work. In addition to the newsletter, I wanted to start Not Boring Club, which was an adult version of what you'd get in college with extracurriculars activities. 

How the 2019 and 2020 experiments helped Packy get to where he is now:

Packy: I got the name Not Boring out of that experience, which I think is good. I think frankly even the time spent doing things that ended up being embarrassing was helpful because it helped me get over potential fear. My whole job is not being embarrassed about putting my thoughts on the internet - so that was really helpful.

How your prior experiences and work can help you years later:

Packy: I think part of the reason I'm able to kind of connect with founders (as a writer and investor) is because I've also really done [worked at] a heavy operational business and done all of the hard stuff -- written internal strategy docs at Breather, and then actually to go execute that strategy. So there's like a little bit of empathy.

How Packy decides on what to experiment on:

Packy: there's value to being different, even if only to get your employees to rally around. There's also this idea of differentiation for differentiation sake… I just love trying a bunch of new things, and it's kind of a gut feel on like "did this do anything good? Or did this not? Or did I like doing this? Or did I not?"

You lose a lot of security when you end up working for yourself. I think I've tried to take advantage of the freedom that it brings as much as possible to just keep doing things that I'm interested in.

How Packy organically became an investor as well:

Packy: I had a friend who was building [a company] that can span real estate and software, and he was having a hard time explaining to investors why it wasn't just a real estate company and why it should trade at a software multiple... So, I wrote up an investment memo, and he then had other investors that were interested in investing in the company. And so he's like: “you should just start your own syndicate” and so it just kind of came out naturally from writing. 

On why its an exciting time to be building digital products and media companies: 

Packy: There are a few moments that have happened where it's just like the internet is just a magical place. I think that's probably the other place that the optimism in my writing comes comes from now is that like I said I had like no Twitter followers, no newsletter, no network even really. And the fact that it's been able to kind of grow from there just based on engagement with strangers is a pretty magical thing.