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Hi friends 👋,

Happy Monday! The week is young and Elon’s already rugged Twitter. What will the rest of the week hold?!

Over here at Not Boring, we’re celebrating a missed birthday and bringing on some smart, curious people. We hope they last longer than Elon.

Let’s get to it.

The Not Boring Liquid Super Team

One of the pieces of advice that people give to those in the middle of a whirlwind is to pause and appreciate the milestones. Whoops. 

Not Boring turned two on April 2nd, nine days ago, and I completely missed it. It was only while writing Not Boring Capital’s quarterly LP Update over the weekend that I realized that we’d had a birthday. 

To be fair, a second birthday isn’t as special as the first one. Making it through the first year is unlikely; making it through the second after getting through the first is much more likely. That’s the Lindy Effect.

I’ve also told the Not Boring story a bunch already over the past year: 

• I wrote A Not Boring Adventure, One Year In on our first birthday and covered the whole journey from Breather to basement to Not Boring. 

• Ben and David had me on my favorite podcast, Acquired, to analyze Not Boring.

• When we crossed 100,000 subscribers in January, I wrote about what had changed going from writing for nobody to writing for so many of you in The 100,000 Foot View.

So instead of looking back again, we can quickly hit some highlights that have taken place in the last twelve months:

• Grew from 42,200 to 113,600 subscribers, 169% growth - nice! 

• Wrote over half a million words

• Launched Not Boring Capital, and invested over $30 million in nearly 200 companies. 

• Passed my stretch goal:

Packy McCormick @packyM

I want Not Boring to make $1 million this year. Which sounds fucking crazy for a free newsletter but I think it’s possible.

February 28th 2021

18 Retweets857 Likes

This is all still very wild to me, and it wouldn’t be possible without all of you reading, sharing, engaging, and pushing back – thank you! 

With the benefit of hindsight, it seems like each of Not Boring’s first two years have been defined by one thing: 

• Year 1: Newsletter Growth and Survival 

• Year 2: Not Boring Capital  

The first year, I started writing the newsletter full-time while Puja was pregnant and I was unemployed and making no money, hoping that it would grow enough that it could at least pay rent. I was surprised it grew as fast as it did and that it got big enough to be a real business. I was also surprised that writing a newsletter helped me get access to invest in early-stage companies. 

So the second year, I launched Not Boring Capital to invest in startups and help tell their stories. That had an impact on the newsletter, too: I wrote more about startups and web3 in the past year because that’s where I was spending all of my time, and less about public companies. When I decided to go for it, I didn’t have expectations beyond, “This will be easier to manage than needing to spin up a new SPV every time I want to invest.” Writing a newsletter and managing the fund – through Fund I and into Fund II, with a growing number of portfolio companies to support – has been a ton of work, and I’ve loved every second of it. 

I didn’t really have a long-term plan. I was just riding the growth.

When I started talking to LPs to raise Fund I, and even into Fund II, I’d often get a question along the lines of: “What do you want this to become in the next 5-10 years?” 

Depending on when you asked me that question, I probably gave a different answer, but most often, my answer was something like, “Not sure! I’m just having fun and following this wherever it takes me!” 

That was partially because I was working so much I didn’t have time to plan ahead, partially because the curve felt so steep that any answer would get stale in a couple of months, and partially because, after a decade of working for only two companies, having all of that freedom felt really great. 

Any good manager will tell you that having employees feels like a bigger responsibility, and challenge, than having a boss. When someone puts their career in your hands, the pressure is on to deliver. That felt like a lot to take on again when the solo thing was so much fun.

Fun doesn’t mean easy. Being solo has meant working seven days per week, every week, for two years (with a week-long break when Dev was born and a recharge over the holidays). Running the fund and newsletter has meant that my calendar is this weird Tetris of meetings whenever founders happen to be free combined with couple-hour writing blocks squeezed in where possible. I work weekends partially because it’s the only time I can be sure there won’t be any distractions. Puja is a hero for making it work, and I’m grateful that we both work from home so I can still spend a ton of time with her and Dev throughout the week. 

Anyway, it’s been a lot, but it’s been working. Hard can be comfortable when it’s familiar. Even if hiring people would take off some of the load (post-onboarding), I thought that bringing more people in would necessarily mean a drop-off in content quality. Last June, in Not Boring AMA, I wrote probably the clearest encapsulation of my thinking in response to Tanay’s question, “How might Not Boring ‘fail’ from here on in?”  

Second, Not Boring could fail if I try to turn this into something it’s not. People often ask when I’m going to hire a team, or add more writers, or even get a ghost writer to take off some of the load. The answer is probably never, unless there are incredibly compelling opportunities to do so or areas that I know you want to learn about that I just don’t think I can analyze well and that no one else covers particularly well. 

No one wants more content. They want something unique that they can’t get anywhere else. The more I try to systematize this and bring in other people to do the creative work for me in the name of more, the faster I fail. 

Reading back on that answer, I made a couple of mistakes: 

1. I framed the team question the wrong way, viewing more people as just a way to add more content as opposed to adding their own unique twist. 

2. I thought too narrowly in terms of just the newsletter, and not the bigger thing I was starting to build across the media business and fund.

3. I couldn’t predict the quality of the people I would be able to hire in the future. 

If you let a therapist in my head, I’m sure they’d come up with more interesting explanations for why I thought there was something special and honorable about going it alone. The long and short of it, though, is that what I’d been doing seemed to be working, and I didn’t want to ruin the magic. 

But over the past couple of months, and especially as I was writing this quarter’s update to Not Boring Capital’s LPs (the fund’s investors, or Limited Partners) over the past week, I realized that there was too much cool stuff to do to not bring some smart people on to do it. 

There are more ways that we can use Not Boring to put our thumbs on the scale for the founders we back than I could manage myself, even with a suite of new products that makes it easier than ever to get leverage from small teams.  

And there are more areas that fascinate me and that I’d like to invest in than I can possibly get smart on by myself, or understand deeply enough to make early, high-conviction investments. Pretty much every day, I read about a new company or scientific advance and think, “Damn, I wish I had time to understand this better” and “I’d love to write a Not Boring on this.” 

Plus, I think if this is just my ideas, it stagnates. We need some fresh spice. 

So we’re going to grow the team, but we’re going to do it in a Not Boring way: we’re going to create a Liquid Super Team. 

We don’t need to build a huge, permanent monolithic structure to have a big impact.

I want to bring in really smart, passionate people who are deeply knowledgeable about hard things and who can translate their knowledge into engaging essays, podcasts, papers, and more. If they want to pop in for a week and co-write a piece, great. If they want to build a career at Not Boring and spin up their own newsletter and fund under the umbrella one day, I would love that. A summer of research, meeting with companies, writing, and building up a reputation works just fine too. I’d love it if people who work for Not Boring explore spinning up a company while they’re here.

After resisting it, I think I know what this third year of Not Boring’s life is going to be about… 

Year 3: Growing a Team at Not Boring While Enhancing the Magic

I was hesitant to hire people because I pictured them trying to write the same things that I did, but just a little bit differently (and if I’m being honest, in my head, worse). It’s funny that I wrote about Liquid Super Teams, but didn’t fully appreciate that the concept applied to Not Boring:

Importantly, Liquid Super Teams allow each individual involved to bring their full powers to bear. They expose each person’s full surface area, rather than hiding away parts inside of a larger sphere. If you compare one big sphere that has the same volume as ten smaller ones combined, the ten smaller spheres have roughly twice as much surface area as the big one. 

I want to bring on people who are experts in things that I’m excited about but not nearly knowledgeable enough on. I want to be able to invest in companies pushing the boundaries earlier because of their knowledge. I want them to pull me back from the ledge of overexcitment when the story is compelling but the science isn’t there. I want people who are really, really smart on different things to explore what happens when they smush their expertise together.

Not Boring’s business model supports a structure like this better than I could have hoped for. Because of the media business, things that would normally cost funds money, like hiring smart people or helping with recruiting, can actually generate a profit for Not Boring. We can sell ads against research reports, spin up a podcast or YouTube series to go deep into a particular area with the people building there, and build a talent collective that’s free for portfolio companies but not for other companies. 

All of those things can drive revenue while increasing the likelihood that we see and get allocation in great deals and give our portfolio companies a better chance of succeeding. Likewise, the fund means that we’re seeing more of the biggest ideas, and we can use that knowledge to make the newsletter and media business better. 

It’s the Not Boring Flywheel on hyperdrive:

Someone on the Not Boring Liquid Super Team has a lot of paths to contribution, all of which involve following their curiosity. We just need to make sure that we have the right structure in place to maximize everyone’s impact for the benefit of all of you and our portfolio companies.

So what’s it going to look like? Glad you asked.

Each quarter, I share the (lightly redacted) LP Update to give you a peek behind the curtain and learn as I’m learning. If you want to read this quarter’s LP Update, you can check it out here:

Not Boring Capital LP Update IV

Today, I want to go deeper on one of the sections from the update in particular: Growing Not Boring.

Building the Not Boring Liquid Super Team

From Not Boring Capital LP Update IV, Expanded Here

For the two years I’ve been writing Not Boring, and the one year I’ve been running Not Boring Capital, one of the things that I appreciated most about it was the fact that it was just me. 

No set meetings, no structure, no boss, and no reports (reports can often be more demanding than a boss). After 10 years in just two companies, most recently managing a team of 150 people, the lightness of being solo was freeing. 

Over the past few months, though, I’ve started to realize that, while I could keep doing everything pretty well on my own, I’d need other people if I wanted to do it exceptionally well. Pretty well would have been fine. If you’d told me two years ago that I could make a living off a newsletter and run a pretty good small fund, I’d have taken that trade in a heartbeat. 

But things change, and as Not Boring has grown, we’ve built up assets that shouldn’t go to waste: 

• A portfolio of ~200 companies, many of which are growing fast and tackling bigger opportunities than they originally set out to tackle. 

• A newsletter with 113k+ smart, curious readers and a Twitter following of 149k.

• A media property – the Sponsored Deep Dive – that is likely one of the most valuable on the internet and has been a better-than-expected way to meet great founders and help bend their companies’ trajectories upwards.

• A diverse, non-institutional 235-person-strong LP base, and demand from 1,500 more readers to back the Fund. 

Each time I think we’ve plateaued, new things start happening that convince me that there’s so much more room to run. Great founders introduce us to other great founders. A chance conversation about a piece turns into an investment opportunity. A podcast conversation kicks off a relationship with a genius founder. The Not Boring Flywheel spins faster and faster, in unexpected ways. 

Ultimately, we’ve quasi-accidentally built something rare – a differentiated VC fund – and I want to lean into that to build something special. 

To get there, there’s plenty of room for improvement. In the first memo, I wrote that there were three things the fund needed to do to be successful: 

• Pick the Right Investments

• Win Allocations

• Help Portfolio Companies Succeed

Pick the Right Investments

If picking the right investments is a combination of sourcing and picking, I’d say our sourcing engine is a B+ and our picking from that group is still too early to tell, but I really like our portfolio. 

I give sourcing a B+ because while the newsletter and network we’ve built has been very good for a one-person operation, there’s more we could be doing to both proactively source early stage companies in particular, and learn when companies are raising a little bit earlier when allocation is more available. On the picking side, I could get a little more ambitious – push a little further out the weirdness curve – if there were people on the team with deeper technical knowledge. 

Win Allocations

We have been successful in winning allocations. I can only think of one or two deals that we wanted to get into and didn’t, and we’ve recently been able to write larger and larger checks in competitive rounds.

It’s still TBD whether and how often we’re able to scale to even larger checks, which I believe will be a function of the resources we can bring to bear for companies.

Help Portfolio Companies Succeed

Lastly, I think we’ve done a pretty good job at helping certain companies succeed – when I write a Deep Dive, that no doubt helps, and I try to be helpful behind the scenes too – but I can’t write Deep Dives on every company. That said, there are some low-hanging ways to leverage Not boring’s unique assets to help companies even more. 

Ultimately, after self-analysis, I realized that we have too incredible an opportunity to give away, and that all of the shortcomings we have can be fixed by bringing on talented people. 

So we’re hiring. 

The lowest-hanging fruit, and something I should have done a long time ago, is to bring on an Executive Assistant (EA). I’ve avoided this for too long because I’ve been worried that it would take more time to onboard them than I’d save, or because I thought I’d look like an asshole “looping in my EA,” but enough people have told me that I’m an idiot for not doing it that I pulled the trigger. I have an onboarding call this afternoon with an EA from Double. Hopefully I get some more leverage and can do more myself with an EA, and at the very least, my inbox and calendar won’t be such minefields. I also won’t miss as many emails, which, ironically, will make me look like less of an asshole. 

More importantly, I’m building out a lightweight but talent-dense team to make us great where we’re only OK currently.

First things first: helping portfolio companies succeed. That has direct benefits in the form of more valuable companies, and indirect benefits in the ability to get more follow-on allocation and in founders introducing us to other great founders. 

To that end, at the start of the month, my brother Dan joined me as Chief of Staff for the media business and the fund. He’s been helping out for free – editing essays, strategizing on growth, and more – while running Finance & Operations at Parade, which recently raised $20M at a $140M valuation in a Stripes-led Series B. 

Dan has been an unofficial fixture, which I highlighted a year ago when I wrote A Not Boring Adventure, One Year In: 

To start, Dan will be leading the business side of Not Boring Media, freeing up more of my time for writing and investing, along with setting both the media business and the fund up to scale. (If you want to sponsor or partner with Not Boring, hit him up!)

One of the advantages that Not Boring has is that we can build new business lines on the media side that we can also leverage to help our portfolio companies. That should mean that we can afford to do even more things to help companies than a similarly-sized fund could on management fees alone. 

So Dan’s primary mandate is to figure out more ways to scalably help our portfolio companies – to work with the smart, curious audience we’ve built to help founders in the highest-leverage way possible. Even as we scale our check sizes, we want Not Boring to be the most bang for the buck on the cap table, and we want to be able to continue to write smaller checks into earlier stage companies without breaking the model. I couldn’t do that alone, and Dan’s already making strides. His first two initiatives were launching a revamped Not Boring Founders podcast and setting up the Not Boring Talent Collective with Pallet. 

Not Boring Founders Podcast

Over the past year or so, I’ve been casually interviewing founders on and off on our podcast feed, but it’s been sporadic and unstructured. I’m no Ben Gilbert, David Rosenthal, Harry Stebbings, or Patrick O’Shaughnessy. 

Dan has already begun to revamp Not Boring Founders (subscribe to meet some of your portfolio founders). He landed FTX US as a presenting sponsor for the podcast, set up a Notion with takeaways from each convo, and pushed me to make it more structured. Now, we start every conversation with three questions: 

1. What does the world look like in a decade if you’re wildly successful? 

2. What does [company] do today? 

3. What will it take to get from here to there? 

Since re-launching, we’ve had seven conversations with founders (six from the portfolio and one outside of it). 

We’re aiming to do two per week, one every Tuesday and Friday. Not Boring Founders is a lighter-weight way to help founders tell their story than a full Deep Dive, and it’s a great touchpoint with founders we’ve invested in or would like to invest in. 

I’m not a great interviewer yet, but I’m starting to get more comfortable. We’re going to lean into making the podcast great and growing the audience over the next few months. Follow Not Boring on Twitter and share when you hear an episode you like to help us grow it.  

Not Boring Talent Collective 

In practically every investor update email we receive from companies, the #1 ask for investors is always the same: HIRING.

As a solo GP, I wasn’t particularly helpful in this area. Larger funds have teams dedicated to sourcing and hiring talent; I was lucky if I happened to know someone looking who might fit a role. That meant I was often left replying. “Great month! Will keep my eye out for anyone who would be a good fit for [x role].” Which is weak. 

Luckily, Not Boring portfolio company Pallet recently rolled out talent collectives, and Dan worked with them to launch the Not Boring Talent Collective. 

The Not Boring readership is full of smart, curious people – people willing to read ~10k words per week – many of whom are looking for their next thing. So far, we’ve admitted over 500 of you from places like Google, Stripe, Meta, Amazon, Citadel, Peloton, Instacart, and many more top companies into the talent collective. Then we give our portfolio companies free access. 

(If you’re looking for a new job or looking to hire Not Boring people, sign up here. If you’re a portfolio company founder, reach out to Dan to get set up with free access!)

So far, nearly 100 connections have been made between hiring companies and talent. Already, 35 portfolio companies have signed up. Here’s early feedback from one of them: 

This is exactly the kind of thing I want us to be doing with Dan on board: finding scalable ways to help portfolio companies by leveraging our unique assets without needing to build out an enormous team to do it. Bonus points if we can use portfolio companies’ products. 

We have a couple of other things in the works, as well: 

{Redacted New Content Series Coming Soon}

👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀👀

Website

We’ve survived two years without our own website. It’s probably time to grow up. There’s nothing revolutionary about a website obviously – we’re in the small minority of funds who don’t have one – but I think we can do some valuable things with ours given Not Boring’s audience. We’re planning to get this live in the next couple of months, working with a couple portfolio companies of course. 

Having Dan onboard and letting him loose on the tools at our disposal is a multiplier – we should be able to add more value to portfolio companies without needing to build out a platform team. 

Having him onboard also means that we can bring on more people without slowing down. 

Hiring Research Analysts 

To that end, we’re opening up two roles I’ve been dreaming about for a while: 

• Atoms Research Analyst 

• Bits Research Analyst

When Not Boring is at its best, we’re explaining and investing in new things that push the limits of what’s possible. 

Writing about a SaaS company can be interesting, but there are a lot of people who do it better than I can. Explaining DAOs or NFTs before most people knew what they were, or writing about Hadrian and what it means for America and space, is where I think we can have the biggest impact. The world continues to get crazier, and I want people to meet all of the change with curiosity and optimism instead of cynicism and fear.  

But I’m more curious than smart, and I’m probably a little too optimistic. 

So I want to hire two people to the team who are: 

• Up-and-coming experts in their fields, 

• Much more technical than I am, and 

• Know how to write well. 

I realize that we’re looking for needles in a haystack, people who have a lot of amazing options, and in return, I’m hoping that I can offer them space to explore broadly, a platform, and a chance to hone their storytelling skills. Technical people who can tell a compelling story are hard to beat. 

The Atoms Research Analyst will be someone who loves reading (and writing) research papers and doing science in the physical world. They might specialize in Climate, Space, Biotech, or some other corner of Deep Tech, but above all else, I want them to have a passion for, and familiarity with, everything going on at the frontier, and an ability to explain those things to normal people, like me. They’ll help source and analyze deep tech investments, write company memos, and write research reports that go out to all of you. 

The Bits Research Analyst will be someone who thinks at the speed of the internet and understands all of the latest, wildest things happening in web3. They can see a pile of Legos and make an educated guess as to how they might snap together. They’re ideally technical, or technical enough to be dangerous, familiar with the most interesting people and projects in web3, and able to explain complex concepts simply and engagingly. They’ll help source and analyze web3 investments, live in Discords and Telegrams, write project memos, and put together research reports that go out to all of you. 

In both cases, I want people who share my optimism, but who are willing to tell me when I’m being more optimistic than the science or vibes suggest I should be. 

We’re open to interns, fellows, x-in-residences, part-time analysts, or full-time analysts, local in NYC or remote, pseudonymous or doxxed. Those titles are written in pencil; we can specialize and expand. If building a Liquid Super Team means being able to bring people we otherwise couldn’t onboard, I’m all for it. I just want the best and brightest. We’ll expand to more positions over time as people specialize.   

Hell, if there’s a different role that you think we should be hiring for instead of these roles and aren’t, hijack the application and let us know. 

I just want Not Boring to be known as a place where really smart people can come to both learn and teach, for as little as one newsletter or as long as a career. I want it to be cross-disciplinary – I think that some of the greatest opportunities will come at the intersection of Bits and Atoms, and I hope that we can both discover and generate the coolest things happening at those intersections. Above all else, I want it to be fun, an opportunity for high-horsepower people to relax, explore, dream, and translate what they find to our audience. 

You can find job descriptions and applications here. Be warned: applicants are going to have to write: 1,000 words on the most fascinating company or trend in their space.

Apply to Join Not Boring

Onward and Weirdward and Funward

After two years, it’s time for Not Boring to grow. Instead of more people making it more corporate and stuffy, I hope that adding new brains to the mix is going to make Not Boring even weirder and more fun. 

If you’re reading this, thank you for making the past two years the best two years of my life and career. I feel very lucky to get to do this as my job. Now that we’re growing, please please please give us feedback, tell us when we’re moving in the wrong direction, and point us towards the things that you want to learn more about. 

All of this is only possible because you’re willing to read thousands of optimistic words per week. I hope that growing the team means even more reasons for optimism.

Thanks to Dan for the edits and analysis.

Thanks for reading, and see you on Thursday,

Packy