Product-Led Sales (PLS) AMA: Packy McCormick

Community builder, Web3 expert, investor, and founder of Not Boring

Alexa Grabell
April 12, 2022
Product-Led Sales (PLS) AMA: Packy McCormick

Alexa, CEO of Pocus, hosts Product-Led Sales (PLS) AMAs with PLS experts to share best practices, frameworks, and insights on this emerging category. These AMAs are an opportunity to ask PLS leaders any question — ranging from hiring to sales compensation to tech stack — in a low-key, casual environment.

The PLS AMAs are for members of the Product-Led Sales community, the go-to-place to learn, discuss, and connect with go-to-market (GTM) leaders at product-led companies. The goal of the community is to bring together the most thoughtful and innovative GTM leaders to build the next generation of sales together.

Interested in joining? Request an invite here.

Now keep reading for a recap of what we discussed in this week’s AMA chat.

Introducing Packy, Founder of Not Boring 👋

Packy McCormick was previously in the startup world at Breather, where he exited as VP of Experience to strike out on his own and start another real estate-based business. 

However, COVID forced him to pivot and today he’s built a community, a brand, and an investment fund around an email newsletter with 100,000+ subscribers.

In this recap of the AMA discussion we had with Packy, we’ll share the highlights around how he did it and, on a related note, his take on how Web3 is changing the modern tech landscape.

How Did The Not Boring Brand Get Started?

Packy’s brand Not Boring is built on an email newsletter-based educational resource that offers a fun (aka not boring) way to learn about the latest in business news and strategy. The Not Boring community is full of over 100,000 folks from all over the globe who work in tech, finance, real estate, design, and more.

Packy also founded Not Boring Capital, an $8 million venture fund that invests in “companies with stories to tell” — including Pocus and many other companies in the product-led growth (PLG), data, and Web3 space. 

And it all sprang from a kernel of a not-so-great business idea and a good ol’ pandemic pivot. 

Packy: “At first I had a community business in mind — a fun idea that probably would've been a bad business. The idea was called Not Boring Club and it was essentially Soho House meets college extracurriculars. I had a Slack community going and I had also started writing on the side. 

“When COVID hit and that business idea fell apart, I already had this newsletter that I'd been writing, so I decided to go all in on that. It worked out that I was writing a newsletter when I was stuck inside and when everybody else was stuck inside and could read the very long pieces that I wrote. That was ultimately super helpful.” 

“Nobody cares. Just go start experimenting because, especially in the beginning, nobody's going to be watching anyway.” 

Differentiation, Consistency, Experimentation: How to Grow Your Brand Through Content 🖊️ 

What, aside from timing, helped Packy grow his writing side hustle into a full-time gig?

For him, he focused on differentiating the way Not Boring looked and sounded compared to everything else he saw on the market. On top of that, he recommends brands also focus on two very achievable tactics as they start carving their niche in the content marketing space: 

  • Consistency
  • Willingness to experiment 

Packy: “My most generalizable advice for how to do something like I did would be to figure out what your unique voice is. I think that’s really, really important when you're talking about a brand, and even more so when you're talking about community. Figure out what you're trying to say, how you're trying to say it, and how you're different.

“Though the tone has shifted a bit, in the early days of Not Boring, I thought about Ben Thompson [biz analyst and writer]. I thought: Ben Thompson is way smarter than I am at writing about businesses and strategy, but he can’t use silly memes and jokes because he has a reputation to uphold. I had no reputation, so I could have any voice I wanted. Yes It's all the same research, but presented differently. That was, I think, a big differentiator that helped.

“Business model differentiation can also help. Ben Thompson is famously subscription based. I went with the opposite model — ads, sponsors, etc.
“And then, just consistency. I've published at least once a week for the past two years. I've written something every day. That builds up over time.” 

And imposter syndrome? Yeah, even the best of us get it. In Packy’s opinion, there are at least 10 million other people who are more qualified than he is to cover the topics that he writes about. So what thought kept him going at the beginning when doubts crept in?

Packy: “Nobody cares. Just go start experimenting because, especially in the beginning, nobody's going to be watching anyway.” 

How to Dive Into Technical Topics Without Scaring Away Your Audience

One thing we think Packy’s newsletter is really good at is presenting technical topics in a way that’s digestible. We wanted to know how he manages to create complex content that’s approachable but also not overly simplified. 

Packy’s approach is three-fold: 

  1. Write as you’re learning about a topic, and just take the audience along for the ride.
  2. Don’t be afraid to cover the technical stuff, but always follow it up with a more high-level explanation. 
  3. The secret is empathy. Think about your reader and include the information that’s really going to resonate with them — how the topic will impact their job, real-life examples of the topic that readers might be able to see around them, etc.

Packy: “I think readers can tell that often I'm learning about the topic right alongside them. I’m only maybe a day ahead of the readers, and I’m just translating as I learn. But I’m not dumbing it down or talking down. In fact, I end up going way too long. My last couple Monday posts were 14,000 and 10,000 words respectively, which isn’t necessarily the right thing to do, but I think shows that there are no real rules. I like that length because I can cover both the really technical explanation and the higher-level explanation.

“It requires empathy for readers, which can be hard when you spend every waking hour thinking about your company's product. But as you're thinking about communicating to an audience that doesn't live and breathe your specific product every day, just think about the journey that they're going through to help create content that resonates with them.”

What Comes First, Community or Product? 🐔

Many people in our PLS community and in the product-led space as a whole often debate over which should should be developed first — a community that proves product-market fit or an MVP of the product itself.

For Packy, who doesn’t consider himself a technical person, the answer is surprisingly product. Which, in his case, is his content. He was able to build a community by regularly creating high-quality content that was shared on platforms like Twitter. 

However, that doesn’t mean going out there and spamming your followers. It’s about adding value, staying present, and engaging in thoughtful conversations. If you’re consistent, a community should eventually come together. 

Packy: “In terms of community versus product, I've done very little intentional community building or intentional growth measures. It's really just all been focused on the content. The weeks that I've grown the most have been because that week’s content was shared the most. In my experience, I'd say focus on the product first and then the community will form. And look for signals in who's engaging with the product to find early, passionate people to seed your community with.”

A Scrappy Tip for Content Distribution

While quality and consistency are cornerstones of community-building content, there’s another little something that can help get you there faster — content distribution. 

We wanted to know what scrappy tactics Packy tried in the early days to get his content in front of more people. No surprise that he took a similar route many early-stage marketers do: post to Reddit, Facebook, and Hacker News; get banned for self promotion; repeat. 

Eventually, he found a more useful “hack” in creating content about companies that he thought the people inside those companies would appreciate and share. 

Packy: “The tactic that probably had the biggest impact was when I wrote about specific companies, the content would go viral inside of those companies. This worked particularly well for companies where the employee base has pride in their employment at that company.

For example, I've written about Slack a couple of times and I know those pieces were shared a bunch inside of Slack. I wrote about Stripe and I know it was shared inside of Stripe because I got a lot of subscribers from Stripe after that. I had to start thinking about who would read and share a piece, then create for that audience. That probably speaks to niching down even further into something that only a few people really, really care about and then going from there.”

Looking Toward the Future: Web3 and the SaaS Landscape 🎱

Web3 is a term used to signify the burgeoning version of the World Wide Web. Web2 is our current iteration, where the focus is on consuming and creating information. In Web1, the focus was on simply consuming information. And in Web3, the focus will be on consuming, creating, and now owning information. 

In Packy’s words “Web3 is trying to take the great parts of Web2, which is that it's easy to use and billions of people are interacting via it, and combine it with the ability to not be deplatformed and actually own the thing that you're building — which ironically harkens back to Web1.” 

There are a few core elements of Web3 that Packy is most excited about:

  • Ownership
  • Composability
  • Open data upon which anyone can build 
Packy: “What I view as Web3 is just the ability to give people who use your products ownership over what they build using those products. That's the first piece. Another piece is the fact that everything is open source by default, has incentives baked in, and can ‘snap together’ — it’s composable. The third key element is this shared open data layer that anybody can build on top of. I think this is a really interesting aspect of Web3 that we'll probably start seeing used more often.”

Where Packy sees these Web3 elements impacting the SaaS space the most is in the experience sector.   

Packy: “There are a lot more data infrastructure tools coming out in Web3 this year. This idea is that you will be able to show up to a website, log into it, and then it will populate with your inventory of tokens, NFTs, and experiences that you've had in Web3. To me, it’s exciting to have sites that are a little bit more personalized to the things that you care about. I hope we'll see that this year, or at least some early attempts. In 2023 and beyond we should definitely start seeing these things.” 

“You’re not asking people to spend a ton of money and you're not asking them to speculate, what you’re saying is ‘Hey, you're as important a part of this community as we are. You should own this thing and get to control it as well.’ That’s what Web3 can offer.”

What’s Web3 Got to Do With PLG? 

Interestingly, a fair amount of people in the Web3 infrastructure space have signed up for our waitlist at Pocus, so that got us thinking about the intersection of Web3 and PLG.

In our opinion, and Packy shares this thought process, businesses with Web3 elements won’t be totally alien. At the end of the day, they’ll still need to grow. They’ll still need to attract leads, add value, and use data to inform next best steps to close sales. They’ll still need a product-led motion. 

Packy: “I think one of the reasons that my Web3 writing has done fairly well is that Web3 has to abide by the same general concepts and some of the same rules as traditional business. In Web3, businesses will still need to get people to try their products and to retain users. There are a lot of things that are similar, there are just a couple new elements like the use of tokens and shared data. There are a lot more similarities than the haters would have you believe.” 

When Should PLG Orgs Start Thinking About Web3? 💭

Packy predicts Web3 will roll out in phases, starting with plug-and-play elements and then expanding as business capabilities advance and user understanding grows. 

But one of the most important considerations with Web3 isn’t that the tech works — it’s that your community is on board with using it. Technology will never take the place of communication, not even in a Web3 world. 

Packy: “I'm seeing a lot of companies now that are building the tools that will make it much easier for communities to plug in Web3 features. On the technical side, we’re probably months out, if not less, from having the ability for businesses to create tokens. 

“Next will be figuring out how to use these tokens. Maybe you just use the tokens to gate content. That version might happen before the full Web3 experience, which is when you're giving full ownership of the community to the people in the community. That will require there to be real rules around decentralization and also that you figure out how to get liquidity for tokens, so they’re tradeable and have value for the people holding them. I think we're probably a couple of years away from all of that being sorted out.

“Finally you have to understand that you'll need to communicate this idea to your community. You’re not asking people to spend a ton of money and you're not asking them to speculate, what you’re saying is ‘Hey, you're as important a part of this community as we are. You should own this thing and get to control it as well.’ That’s what Web3 can offer.” 

Don’t Miss the Next PLS AMA

As always, we had so much fun and learned so much from our chat with Packy about growing Not Boring and the pending impact of Web3 on the SaaS and PLG landscapes.

To get involved with more enlightening conversations like the one we had with Packy, all you have to do is request to join Pocus’ PLS community! Once inside, you’ll be able to engage with plenty of PLG experts and attend AMAs in real-time to ask all your burning questions. 

We’ll see you there!

More reading from Packy:

Alexa Grabell
Co-Founder & CEO at Pocus
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