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Hi friends 👋,

Happy Monday! Last week, we crossed a big, round milestone: our little Not Boring family is now 100,000 strong.

While I’ve been excited about the small victory, I’ve also noticed something new: a voice in the back of my mind asking me what the cynics and trolls are going to think of what I write.

If having more subscribers and followers means that I get more cautious in what I write, this whole thing falls apart, or at least gets a lot less fun. I want to be able to take risks, write about things that are more complex than I could possibly comprehend but try anyway, make wild predictions that are likely to be wrong but make you (and me) think, and explain businesses that I find fascinating regardless of whether I think their price will go up. 

The opportunity to be misunderstood grows with every new person who joins Not Boring, so I want to take this milestone opportunity to be clear: I’m going to get a lot of things wrong, there’s no correlation between audience size and intelligence (I’m the same idiot today I was when 400 people read this), and if I stop getting things wrong, we can all go home. 

I’m writing this to get that voice out of the back of my head so that I can take bigger swings and be even more wrong in the next two years than I have been in the first two. Consider this my auto-reply to the trolls.

Let’s get to it. 

The 100,000 Foot View

On Thursday, we hit a milestone that wasn’t even in the realm of possibility when I started writing this newsletter in April 2020 at the beginning of the pandemic: 100,000 subscribers.

That is an absurd amount of people. The biggest stadium I’ve ever been inside of was Alabama’s Bryant-Denny Stadium (Roll Tide) which seats 100,077. 

(My friend Ryan Dempster tweeted this comparison to Texas’ stadium, which works too.)

If everyone receiving this email tried to go to an Alabama game at the same time, 606 of you wouldn’t get a seat. Of course, not everyone reads every email – open rates have been hovering between 50-54% – so to torture the analogy, a little under half of the people in the stadium would be asleep, but still… holy shit. 

THANK YOU!

None of this makes any sense. I’m not an expert on any of the topics I write about. Getting here was not a foregone conclusion, or even a goal, when I started writing. I just wanted to explore the things I was curious about. When I started hitting send on newsletters, I thought all of my friends were talking shit about me in a group chat. 

I won’t go over the whole story again here. If you’re newer here and want to get the backstory, you can read A Not Boring Adventure One Year In or listen to the Not Boring Acquired Episode. 

Long story short: I’ve had a charmed ascent. 

I get to do the two things I would have wanted to do if I were retired – write and invest. I’ve gotten to meet a lot of my tech and business heroes. And for the most part, people have been really nice. 

I’d heard that once you get more than 10,000 Twitter followers, the experience gets toxic and negative. I didn’t have that experience. We made it all the way to 100,000. The Great Online Game has been really good to me. 

With all the good, I’ve also noticed something turn over the past month or so, as we approached 100,000. Friends aren’t talking shit in a group chat (as far as I know), but strangers have been talking more shit on the internet. There’s more trolling and negativity than there was before.

Admittedly, I brought some of it on myself.

Every week, I write about topics and industries that other people spend their whole lives working on. I get things wrong. I started an asynchronous debate with a very popular marketer, which drew the ire of some of his fans, and wrote a sponsored post on a public company, which got a bunch of pseudonymous accounts on fintwit riled up. I’ll keep pushing boundaries, within the bounds of what is legal and ethical, and listen when you push back constructively. 

But some of it just comes with the territory.

More followers and subscribers means: 

There’s a higher ROI to dunking on me. More people will see the dunks in my replies or comments, and there’s more to be gained by taking me down. As AppliedDivinityStudies wrote last week, “By criticizing someone more prominent than yourself, you sap their life force, attempt to take their reputation for your own, and challenge their high standing.” Damn.

The things that I tweet and write get outside of the circle of people who have context on Not Boring more quickly. It’s a very weird feeling. There was no point on this graph where I felt that I got any smarter or that my word became bulletproof, where I switched from “I’m just learning this out loud” to “accept this text as Gospel,” but there’s a point on here after which new people reading Not Boring for the first time probably think I think I’m more right than I am. There’s missing context.

An essay will read differently to someone who’s read a lot of Not Boring essays than someone who’s coming in fresh, like this person… 

Even the most stoic person would read that comment and feel a momentary displeasure, and I’m not the most stoic person. This newsletter is me and I’m a people pleaser (probably a blessing and a curse). Reading comments like that hurts, and now, there are comments like that, and worse, every day.

Maybe I need to meditate more, but it’s very possible for a pseudonymous account with like seven followers to ruin my day.

That said, it’s objectively very funny to have my day ruined by @frogdick42069 or similar. This is the internet, baby! This is the weird I signed up for, and love.

There’s this famous Eugene Wei tweet from 2018 that I didn’t really appreciate until recently: 

Eugene Wei @eugenewei

The rhetorical style of any Twitter account that continues to gain followers converges on that of a fortune cookie.

May 21st 2018

344 Retweets2,116 Likes

At the time, I thought the point of the tweet was that as peoples’ followings grew, so did their egos. That they tweeted like fortune cookies because they believed their pithy thoughts were profound and worthy of thousands of likes. 

Recently, I’ve come to realize that the real point is that as peoples’ audiences grow, the risk of being misunderstood or running into trolls grows exponentially, to the point that the safest move is to just tweet or write dumb, simple shit, stop experimenting, stop taking risks, and avoid controversy above all else. Pander to the lowest common denominator. 

So people either retreat to simplified, dumbed down versions of their thing, or they go full heel turn, embracing and feeding off of the hate. That sounds kind of fun for the right kind of person, but it doesn’t work for me. 

Another is to own it. I was going to write a whole piece expanding on the last few paragraphs about how strange it feels to go from being nobody one day to – after working non-stop for two years – being somebody people like dunking on. 

But then I realized: 

1. This is the greatest job in the world.

2. I have fun writing what I write.

3. If you had told me this would be the situation I’d be in two years ago, I would have laughed.

This is the first time I’ve had to deal with consistent trolling, and now that it’s here, it’s probably going to be here for as long as I continue to do this. So I’m going to do a couple things: 

1. Appreciate that two years ago, I would have loved to have even a single troll.

2. Recommit to the things that the 99.9% of non-trolls reading this are here for.

Not Boring is for the optimists, and for the skeptics who are willing to keep an open-mind. It’s not for the perma-cynics. They’ll always find something to bash. That’s OK. 

I’ll remind you at every opportunity that I’m an idiot. I often write, “This is not investment advice,” and I know that’s a form disclosure that people have to write even when they don’t mean it just to avoid getting in trouble, but I legitimately mean it. I’m not a very good trader. I fall in love with my positions. That’s why I’m drawn to VC – where the holding periods are many years – instead of a trading desk. Plus, I don’t write how I’m sizing investments, expose my whole portfolio to show how a certain asset fits within it, or write follow-ups to say, “Hey I sold this position,” all things I’d expect of someone from whom I was actually taking investment advice. 

I’ll try to keep it positive, but I also won’t shy away from mixing it up with people who I think are dunking on others for their own personal gain or bending the facts to fit their own narrative, like I did last week. There’s a difference between positive and meek. I’ll call out scammers, but I’ll never knock people who are building something they think is important in good faith. 

I’ll continue to write and invest and work with sponsors to tell their stories in one big mix. I’m a firm believer in “no conflict, no interest.” Everyone has incentives, mine are just more clear. I’m always going to be conflicted and biased; my promise is to disclose my incentives more clearly than anyone else, to never write about things I’m not genuinely excited about, and to always be fair and honest.

Sponsored, invested, or not, I’ll always write about the things that I’m most curious about, where the delta between my current understanding and my desired understanding is the widest. I want to explain complex but important topics as simply and approachably as possible. That means that I’ll often get things wrong, or miss important pieces of the story. If I get everything right, it means that I’m leaning too heavily on comfortable or easily understood topics. 

I’m lucky that there are 100,000+ of you smart, curious people who want to explore with me. Please don’t take what I write as the final word. If you’re interested in a topic I write about, use my piece as a starting point. The best way to approach Not Boring is to learn with me, not from me, and then go off on your own learning adventure. 

This is going to be a particularly interesting time – the first bear market in Not Boring’s young life. I’m almost certainly going to write positive pieces about companies and projects whose prices will proceed to tank 10% on the very same day. Trolls are going to skewer me, I’m going to hurt for a second, stew, formulate a witty response, delete it, move on, and hopefully appreciate the absurdity of the fact that that’s all part of my job.  

My worst call ever – short Bill.com – is a great reminder that I don’t play the bear very well. It’s not who I am, and there are plenty of bears out there. You should read Not Boring for the optimist-leaning analysis (I only write about things I’m excited about) and then read other people who are better bears to form a full picture. 

But before we get to whatever’s next, I want to take this opportunity to pause and let you know how much I appreciate that you let me do this for a living. Thanks for being one of the first 100,000. As web3 people are fond of saying, we are still so early.

In a decade, there will be more than a million of us smart, curious Not Boring people. The closer we get, the funnier it will be that that many people read the things that I write. I promise to get things spectacularly wrong, get dunked on, shake it off, and continue exploring and learning. I don’t think my skin will get any thicker, it hasn’t yet, but maybe I’ll read back on this and remember that I knew it was coming and that I signed up for it.

No matter what happens, I won’t start writing fortune cookies. You’re too smart for that. If you catch me doing it, you have my permission to troll, dunk on, and eviscerate me. 

The world is only going to get crazier and faster and more complex. I’m going to do my best to keep up and translate the incredible things people build into words.

Viva the Optimists.

Thanks to Brett, Puja, and Dan for editing!

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Thanks for reading and see you on Thursday,

Packy