What is Nathan Barry doing?

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Hey honeys and hustlers,

Sometimes, smart people do things that seemingly don’t make sense. Nathan Barry is the founder of Kit (formerly ConvertKit), and he bootstrapped the company to $40M in annual revenue. By comparison, both Substack and beehiiv have raised venture capital and still haven’t reached that amount in annual revenue. Yet many of his recent actions don’t seem to coincide with a person who’s achieved this incredible feat.

• He started a podcast with Rachel Rodgers, but she is no longer a part of it for some reason. Nathan Barry's show has got to be one of the worst-produced shows. So much of the talking just gets off topic so quickly. The audio quality is inconsistent. The guests are inconsistent. Not sure what happened to Rachel, truly. It's just a mess.

• He spent a ton on a rebrand that reportedly messed with some email lists and sends of users, making a frustrating adoption period for current users. It’s unclear if the rebrand, website redesign, and pricing restructuring have helped them attract new users and increase retention.

• He’s opening podcast studios across the US for Kit users. As Kit is an email-first company, myself and others are struggling to understand if there is enough demand for this among Kit users to warrant the investment and fanfare.

Contrary to what seems to be a string of incoherent actions, I don't think someone who bootstrapped a $40M/year business is suddenly off his rocker.

There are many things that Kit gets right. When I was looking into moving from Substack, Kit was attractive for their ability to sell digital products natively (complete with landing pages for products) and their many native integrations with so many apps (like Canva, Senja, Transistor.fm, and more). These things may not have swayed me, but they have attracted some top creators. According to Nathan Barry, here are a few people who have joined recently:

• Ellen Degeneres

• Jay Shetty

• Amanda Goetz

• Justin Moore

• Lil Jon

• Morgan Freeman

• Matthew McConaughey (I subscribe to this one)

• James Clear (I subscribe to this one)

My theory? I think he's trying to put himself in the shoes of the next top creators - podcasters and educational video creators - so that he can better lead a company that’s making an ecosystem where they can thrive via email. However, now that Substack has made the pivot from email-first platform to media-first platform with a social feed, he may be facing some stiff competition for well-known creator acquisition.

The Substack Caveat

The founders of Substack aren’t doing any of the things Nathan is doing to build their revenue and attract users. In fact, they’re putting in a fraction of the effort and making way less popular choices in the eyes of their user base. But there’s something to be said for Substack’s social feed, called Substack Notes, organically attracting top creators who have historically used Kit. I think it speaks to a larger desire of people wanting greater organic discovery for their email newsletters, and a calm social feed without ads. Notable Kit users that I’ve seen on Substack lately include

• Jay Clouse, writer of Creator Science. He’s moving his personal blog to Substack.

• Justin Welsh, writer of Saturday Solopreneur. He’s writing Unsubscribed on Substack.

• Felicia Pride, founder of Honey Chile. She moved her newsletter, The Sweet Build, to Substack.

• Chenell Basilio, writer of Growth in Reverse. It looks like she did a daily newsletter challenge on Substack and is decently active on notes.

• Dan Koe. He’s writing future/proof on Substack

I’ve also seen some well-known creators and brands beginning their journey on Substack that I think would be the type of creators Nathan Barry would want to attract.

• Bandcamp (Bandcamp Fridays, support for your favorite indie music artists pls)

• Pop Crave (a surprising news source that has ventured outside of Twitter)

• Ava DuVernay (got two free tickets to Shadow Force from her newsletter)

• Ziwe (the icon herself, we are honored by her presence)

• Vic Mensa (the rapper who’s now sober)

• David Perell (made an account for How I Write, his podcast)

I’m unsure if we’ll ever know the outcomes of the fruits of his labor, but I think when you look at them through the lens of a CEO looking to scale his company, he seems to be playing the long game. Making himself relatable but also a better leader seems to be the name of the game. I also think, as someone who just started their journey in digital products, that he’ll be knocking on Kajabi’s door next with full-fledged course creation within Kit (they currently offer email courses but not cohort-based courses or self-paced courses to my understanding). For creators who want to generate revenue from their email newsletters outside of paid newsletters, which he spoke about on this episode of Creator Debates, I think Kit may be a more formidable contender for many in the near future. AND he won’t have to worry about paying back investors when he reaps the revenue rewards.

I could be completely wrong though, just my 2 cents. Tell me what you think! What are you using for your email newsletter? Would you consider switching to Kit?