Re: Packy
Shay Silvertooth
Public and Not Boring are a perfect match: like Not Boring, Public makes the investing conversation fun. Public is an investing app AND a social network for talking about business trends, and the social features make it easy to share ideas.
A year ago, we knew that Dev was coming, but I had no idea what I was going to do. I had quit my job, launched an in-person company that got crushed by lockdowns (and was probably a bad idea anyway), and to top it off, I caught COVID the week I decided to start writing Not Boring. I was lost.
I wrote about education and IRL Member Communities to make sure there was a real opportunity. One of the problems with being good at writing is that you can convince people that bad ideas are good. You can even convince yourself.
One year ago, I was locked in my Brooklyn apartment with COVID, feeling incredibly stuck and a little hopeless. Not Boring Club was on indefinite pause. In February, Puja and I found out we were having a baby, and I had zero income. The pressure was on.
My brilliant plan? To turn the newsletter into something that could at least pay rent at some point in the future while I tried to figure out what I wanted to do next. Maybe it would even help me find a new job.
When I started writing, I wanted to write about tech and strategy (one of the first pieces I wrote was on Natively Integrated Companies and another was on Shen Yun and Startup Economics), but I thought the space was too crowded (the first piece I ever wrote was the Best of Ben Thompson).
In May 2020, one year into writing a newsletter, I wrote Looking Back, Forward, and Up to reflect on one year of writing and set goals for the future. My first goal was to hit 5,000 subscribers by the end of the summer, and then turn on paid subscriptions. From that piece:
The most important growth levers over the past year ended up being really simple: quality and consistency. Show up enough for good things to happen every once in a while.
Polina Sharing Per My Last Email in The Profile. In November 2019, Polina Marinova shared Per My Last Email in her excellent newsletter, The Profile, after I won a contest to receive a tote bag full of some of her favorite books. I picked up 49 subscribers in two days, and I thought that was the most incredible thing in the world. Thanks, Polina!
Asking People to Share and Launching Not Boring. While I wrote Per My Last Email, I was afraid to ask people to share -- it felt so self-promotional -- so I buried the ask at the bottom of emails. When I announced that I was switching to Not Boring and making it a thing, I asked people to share front and center.
First and foremost, he said that we should set up a landing page for Not Boring so that we could launch on Product Hunt. He built a landing page using Usmo, I sent an email introducing the homepage to our 1,885 subscribers, and we launched on ProductHunt.
Tommy also launched a Referral Program through which many of you have invited over 2,000 people to join the Not Boring family -- thanks to all of you for telling your friends! Props to the top three referrers: Joakim Jardenberg, Hunter Walk, and Johannes Sundlo. NB ? ?? .
The Passion Economy is taking off, enabling thousands to make a living off of what they create. Personally, I love the idea that covering the basics doing something that I love will allow me to take bigger swings elsewhere.
At the time, after listening to all of the Substack hype around subscriptions, I assumed that I, too, would charge people to read the newsletter. Ultimately, I decided that was the wrong move for Not Boring. Why?
Math. I did some rough math when I was making the decision, and realized that I could probably make a lot more money over time with sponsorships assuming that keeping the newsletter free meant growing faster.
I surveyed Not Boring readers to learn more about their backgrounds, professions, and preferences, and with examples of previous sponsorships in hand, put together a rough sponsorship deck. Instead of doing outbound sales, because I hate selling, once I had the deck, I decided to tweet it out into the universe.
So far, sponsorships have proven to be the right path for Not Boring. After many months of generating no revenue, the business side of Not Boring is starting to pick up steam, and April is set to be the best month yet:
Just writing about companies is one thing, but putting my money where my mouth is, and giving readers the opportunity to do the same, gave me more skin in the game. Plus, I thought that we could give portfolio companies an early advantage by helping them tell their story to potential customers, employees, and investors.
As an added bonus, the Syndicate has been a fun way to let readers participate and build relationships without launching a traditional community. Michael Batnick wrote about the experience as an LP in Everyone is an Investor. That made my week.
Working closely with companies on Sponsored Deep Dives has created some of my strongest relationships in tech, led to investment opportunities for the Syndicate, and introductions to more companies to write about and invest in (thanks especially to Nick Abouzeid and Mike Wenner for spreading the word about Not Boring!)
I still view this newsletter today as just a bigger version of the little thing it was a year ago with a few friends and random internet people, but I also realize that with more readers comes more responsibility.
One small, irritating nitpick: Maybe it's because I read this essay a couple of times, but I noticed several minor grammatical errors. In your quest for perfection, I would suggest you edit perhaps one more time before you have the urge to hit "Send."
Good luck. I enjoy reading your stuff, though often several weeks after it hits my inbox. I have about 4-5 tabs of Not Boring columns on my Chrome browser (and several more on Safari on my phone) awaiting reading or re-reading.
Instead of writing about a very big company, which I normally do on Monday, I\u2019m writing about a very small one: Not Boring. It\u2019s been a crazy year, I\u2019ve learned a ton, and it\u2019s just going to get better from here. But it was not at all obvious that this was going to work out a year ago.
Before we get to it, I just want to say a big thank you. Nothing in this story would have happened without you reading, commenting, conversing, and sharing. I feel very lucky that you\u2019re willing to take time out of your day to read what I write.
Thank Public for making Not Boring possible by hitting the link below and joining me over there. If you want to transfer your account from somewhere else, they\u2019ll even cover the fees.
I legitimately didn\u2019t believe this was possible. I would see people with big followings on Twitter or big subscriber lists and think that they had some special je ne sais quoi. I still think that it could end at any moment.
Today, I want to share the Not Boring story as honestly as possible -- it often looks way easier from the outside -- with lessons I\u2019ve learned on writing, growth, business models, investing, and creator psychology sprinkled in. We\u2019ll cover:
If anything in this story seems planned, premeditated, or in any way clean, that\u2019s just my brain going back, filling in gaps, and connecting dots. As much as I write about strategy, this story is about working hard even when it seems silly and following serendipity.
A couple weeks into the new regime, Ben Rollert (then VP, Product at Breather, now CEO at Composer) and I presented at an exec team offsite about the need to differentiate and dig moats in an increasingly crowded and bubbly flex office market. We got cut off halfway through with something to the effect of: \u201CMoats? This is a big market, we don\u2019t need to worry about moats. We have a brand. That\u2019s what Apple has.\u201D
I realized that my brain was going to shrivel up and rot if I didn\u2019t do something. Ben\u2019s always been smarter than me. He saw the writing on the wall and quit. I couldn\u2019t quit right then -- I managed a 150 person team and didn\u2019t want to abandon them -- so instead, I used my annual learning & development budget to take David Perell\u2019s Write of Passage course.
That was one of the best decisions I\u2019ve ever made. One of the assignments for the course was to launch a Substack and get twenty people to subscribe. I reserved packym.substack.com, named it Per My Last Email, and begged my few hundred Twitter followers to sign up:
Two days later, I had 28 subscribers, and we were off to the races. I wrote Per My Last Email on the side, spending a few hours each weekend or early in the morning curating links to essays, books, podcasts, and videos with a dash of commentary. It grew to about 400 subscribers in eleven months. It didn\u2019t make a dollar and I didn\u2019t expect that it ever would.
But I had always told Puja and my family that if I ever got really rich and retired early, all I\u2019d want to do is read and write and talk to really smart people. Per My Last Email let me start doing that in a small way. As someone who\u2019d been so singularly focused on work for a decade, it felt good to have a hobby.
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