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Ava Bookbear Started a Substack That She Now Lives off (6-Figures). I Studied Her Unconventional Path.

by | Sep 25, 2023 | Writing

“Bookbear” doesn’t sound like a 6-figure newsletter name.

If you didn’t know any better you’d think it was just another newsletter written by an employee who writes on the side.

That’d be naive. Stupid, even.

I’ve been a reader of Ava Bookbar (a.k.a NoamPomsky) for about a year. Her newsletter caught my attention because it’s highly sharable.

She’s the only one I know who’s had the opportunity to have her Substack recommended, not once, but twice by Tim Ferriss on his podcast. So as I began fangirling (for Tim not Ava), I researched her newsletter journey.

And I confirmed something I didn’t expect:

Screenshot taken by author

That’s right, Ava doesn’t work a job in the San Francisco tech scene anymore. She’s a full-time Substack writer. You go gal!

Here’s how she makes 6-figures doing it:

She goes where the eyeballs are

I run a Substack newsletter that’s about to pass 100,000 subscribers.

One thing I’ve noticed is writers are so romantic about newsletters and writing books. They think you just show up and write and all your dreams come true. LOL. Not quite.

As I studied Ava’s journey, I noticed she used Twitter/X a lot over the years. She’s built an audience on there of 48,900 followers. If she launched a Substack without this audience no one would read.

The hardest part about a newsletter is finding readers, not writing.

Ava learned this lesson early on. She writes tweets and then links to her Substack in her bio and by replying to her own tweets.

Every successful Substack I’ve ever researched follows this formula. Go where millions of eyeballs are, be helpful, then direct them to your paid newsletter.

She writes about the most popular niche on the internet

The gurus crap on about “niches” like it’ll save your goddamn life.

No it won’t. Niches are overrated. The niche Ava writes about? The human experience. This niche will never grow old or die.

We all struggle with the premise of what it means to be human. Any writer who’s making our experience being alive just a little bit easier is going to build a cult following. That’s what Ms Bookbear does.

She finds a way to take your day, screw with it, throw it around the room, stomp on it, then fill up your head with new ideas.

She makes you feel.

It’s hard to describe. She’s so raw it makes an uncooked steak that’s been sitting on the kitchen counter for a month taste delicious.

She strips away all the bullsh*t and just gives it to you how it is. And so people listen because all the ego and hashtags aren’t in the way.

Tie your favorite topics to what it means to be human.

Substack Chat is her secret weapon

Substack has a lot of features. Many of them never get used.

One feature that confuses the crap out of me is Substack Chat. Part of the reason is because they’ve changed the name of it multiple times.

Essentially, this feature is a WhatsApp group for you and your readers. You can paywall it but Ava doesn’t. It’s how I was able to ask my question to her and get a response.

Most social media apps are one-way conversations. A dude with a big ego and a million followers says something and we’re all supposed to go “Bro, you’re so right” and heart them. But that’s boring.

Readers crave deeper relationships with writers.

I predict the trend of a private group chat with readers — where they don’t have to accept an invitation or leave the platform — is going to be huge.

Ava uses this feature like a pro. Readers love it and she was early to this trend. I suspect it’s one reason people love paying for her newsletter.

The secret the biggest writers will never tell you

Amateur writers often believe great writing is the secret.

They’re wrong. The real writers who rake in the cash know that it’s the network you build behind the scenes that has a lot to do with your audience growth. On the outside Ava looks normal.

If you dig deep you can see she has internet friends like Jeremy Giffon. No doubt influential people like him help share her newsletter.

This reality isn’t limited by privilege.

Any of us can network in the DMs and make friends with those who have Substack newsletters or decent-sized audiences on LinkedIn and Twitter.

Make friends with other writers. Dah.

Turn on paid (not for the reason you think)

This one might seem obvious but it’s not.

To be successful on a platform, contrary to popular belief, you have to align your incentives with theirs. For Substack to make money you have to change your newsletter from free to paid. That’s what Ava did.

When you make your newsletter paid Substack is more likely to:

  • Mention it in staff picks
  • Boost it in topic pages
  • Feature it under a reader’s personalized recommendations

And if your Substack is paid, then it’ll show higher on the topic leaderboards than if you keep it free (example below).

Screenshot by author

If you stay free, though, like I have, then these cool things won’t happen for you. Here’s a kickass hack:

If you’re not ready to make your Substack paid, then just turn on the ability for readers to pay a flat monthly fee ($5 is good) and tell no one.

She’s shown up for more than 365 days

In some ways the internet has been hell for writers.

It’s easy to think you can start a Substack and have Justin Timberlake share it in the next 30 days before you score yourself a new Tesla and a badass attitude that makes you a millionaire.

Not quite.

Ava has been writing her Substack since 2019. She’s been on Twitter/X since 2015 and has been seriously tweeting since about 2020. None of her success happened overnight.

It never does, except Hollywood wants us to think it does.

If you show up on Substack for a year or more, according to my research, there’s a good chance you’ll join the Top 1%.

She has a free versus paid post strategy

If all your Substack content is paid then there’s no way to market your newsletter. The writing IS the marketing.

Readers need to read your work before they’ll pay for it.

Ava publishes at least one free Substack a month. She then shares it on social so readers can find it and get a taste. She then paywalls the rest of her content. What’s different is she let’s a reader read a significant chunk of her Substack before the paywall comes up and asks for a Visa/Mastercard.

Most writers share 1–2 paragraphs and then paywall your ass.

Think about the free versus paid balance carefully. Have a strategy, and a way to share your work to attract readers.

She’s got badass attitude

Let’s finish here.

Most writers put me to sleep. They just write. They put words on a page. Ava doesn’t do that. She blazes it up. She’s sassy, a little edgy.

If you’ve ever read GriefBacon then it’s the same kind of vibe. Or if you’ve read the writer, The Last Psychiatrist, then you know what I mean. They have a voice and they don’t filter what they write.

It’s as if you’re hardwired into their brain and can’t unplug. It sometimes feels like they know you better than you know yourself.

You may think this is an impossible task. It’s not.

We all have this superpower when we stop giving a crap what strangers think, or worse, what our boss thinks. Or even worse, what our mother thinks. Nobody is hanging out thinking about you and your writing as much as you think. *Shares ‘nobody gives a sh*t’ meme of kid sitting on a bus*

Stop self-rejecting. Stop muzzling your own mouth.

When you do, people will share your Substack for reasons they can’t even explain. And maybe, just maybe, you can make 6-figures from your newsletter and quit the cubicle job.

Even if it doesn’t work out that way, you’ll still be better off.

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