The Long Story with Simon Owens

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David Kushner had the kind of mainstream success that most writers dream of. His writing regularly appeared in glossy print magazines like Wired and Rolling Stone. Several of his books became national bestsellers. And his work has even been adapted into multiple TV shows and movies.

But in 2021, David decided to bypass legacy media entirely and start publishing his work to a Substack newsletter. What drove him to do this? In our discussion, David explained how the changing norms over IP rights and his own desire to experiment with serialized storytelling motivated him to make the move.

Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump in the comments section of the post and ask me any questions they have about the media industry or creator economy.

Several of you did pipe in with some amazing questions. I then invited on Alexis Grant, the founder of They Got Acquired, to help me answer them.

We answered questions on a range of topics like

1. How to monetize newsletters on LinkedIn
2. How we’d go about launching a local news outlet from scratch
3. The future of paid newsletters
4. How The Messenger should have spent its $50 million in VC cash.

This Q&A episode is actually part of an ongoing series. Every single month I’ll allow my subscribers to submit questions, and I’m going to do my very best to answer at least one question from every single subscriber. The only way to submit questions is by becoming a paid subscriber to my substack newsletter.

Subscribers also receive a calendly link from me that allows them to book a half-hour introductory phone call. Many of my subscribers use it as an opportunity to tell me about their own media businesses and pick my brain on strategy.

To subscribe, go to https://simonowens.substack.com/

My newsletter: https://simonowens.substack.com/

My newsletter: https://simonowens.substack.com/

When Jack Karmer and Nick Martell launched their daily newsletter Market Snacks in 2011, they kept their names off the publication so that it wouldn’t jeopardize their finance day jobs. But once the newsletter started to attract readers and sponsorship revenue, they decided to come clean. Luckily, their bosses let them continue on with their side hustle.

Flash forward about a half decade, and Market Snacks had gained enough traction that they both decided to go to business school so they could learn to scale the company. Around that same time, they teamed up with a large podcast network to launch a daily companion show, and almost immediately it was featured on the Apple Podcast app.

This success didn’t go unnoticed. Robinhood, which at the time was a fast-growing stock trading app, came on at first as a sponsor, but a few months later decided to outright buy Market Snacks to leverage it as a marketing channel for the app.

Jack and Nick continued to host the podcast while managing the rest of the Market Snacks team, and then in 2022 they went to the Robinhood executive team with a radical proposition: they wanted to spin off the daily podcast and acquire it from Robinhood. Amazingly, their bosses went for it, and that year they renamed the podcast to The Best One Yet.

In my interview with Jack and Nick, we discussed how they came up with the idea for the newsletter, why Robinhood allowed them to take the podcast back, and what they’ve done with the company ever since they became full owners.

Per Grankvist had the kind of media career most journalists only dream of. He was a high-profile columnist for a leading newspaper and a regular face on one of Sweden’s top broadcast networks. But over time he grew disillusioned with mainstream media and its tendency to dumb down coverage of complicated policy issues.

So Per quit his traditional media jobs and launched his own outlet. It started with just an Instagram account that explained thorny election issues, but from there it blossomed into an entire media outlet that spanned across social media, podcasts, and newsletters.

I recently interviewed Per about how he built the company, his approach to monetization, and whether he misses working for mainstream media publications.