Today's guest, Ernie Smith, has been writing for the internet for 15 years. He's been writing his current newsletter, Tedium, for almost 10. We spoke about his approach to newslettering, turning down money from Substack, and making cool stuff for the internet purely for the sake of it.

00:00 Who is Ernie Smith?

01:30 Why (and how) Ernie coded his newsletter himself

05:35 Has personality been stripped from the internet?

12:44 How Ernie grew his audience

15:20 UDM14 — Google without all the fluff

18:56 Ernie’s approach to side projects

31:39 Is the creator economy good for the internet?

41:28 Hopes for the future of the internet

45:10 What’s next for Ernie?

Intro music produced by J. & Doug Organ.

Today’s guest, Justin Gordon, seems to have more energy to expend in a day than we do in a week. Literally: we put out one ~50min podcast episode per week; he once put out one ~50min podcast episode per day for 112 days straight.

Justin has been a podcaster, vlogger, producer, and newsletterist, sometimes all at once, for the last 12 years. In this episode:

00:00 Who is Justin Gordon?

01:24 Lessons from 500+ interviews

04:30 Podcasting every day for 112 days

12:55 6 Lessons from podcasting every day

15:23 Why start a newsletter?

18:17 How to grow a newsletter

19:50 Writing deep dives about entrepreneurs

28:33 The athlete-creator mindset

31:14 Making money as a creator

36:17 The best and worst interviews he's ever done

39:43 Advice for podcasters and writers

Intro music produced by J. & Doug Organ.

Kate Lindsay is a freelance writer and newsletter editor whose own newsletter, Embedded, is pushing 35k subscribers. She's one of the best people out there writing about the internet for the internet. This is an episode about why more newsletters should be run by two people, an indie newsletter born from a shuttered publication, and paying NYC rent with premium newsletter subscriptions.

00:00 Who is Kate and what is Embedded?

05:33 How Embedded evolved from a killed publication

09:56 Kate's other projects (as a newsletter editor and writer)

13:35 Blowing up with the Millennial Pause

16:44 Being an editor vs. a writer

19:09 What is a newsletter? What is a creator?

27:42 The stats — how to grow a newsletter

34:22 Are creators the new journalists?

38:49 Advice for online creators

Intro music produced by J. & Doug Organ.

Today’s guest, Andrew Southworth, always wanted to become a musician. To do so, he became a mechanical engineer. Last year he quit his day job to make music and help other people market their music full time. He does YouTube, newsletters, courses, he has an agency — he does it all. We spoke about:

• 📆 A 13-year long bet to become a creator-entrepreneur
• 🪴 How to diversify, effectively, as a creator
• 🤔 Can you over-diversify?

00:00 Andrew Southworth's many businesses

04:27 When to hire as a creator

07:47 How Andrew makes money

09:42 16 years of being a YouTuber

19:33 Why Andrew started a newsletter

22:47 Andrew's future plans and dreams

25:10 Advice for other creators

Today’s guest is Akhil Chauhan, who runs The Writer’s Job Newsletter (TWJN). But he didn’t create the newsletter — he acquired it.

Akhil has been running TWJN solo (besides occasional social media help) for two years. The guy he bought it from ran it for only one year. We spoke about:

• 💰️ The economics of a newsletter acquisition
• 🤐 Keeping his personality (mostly) out of the newsletter
• 🤝 Pulling off a seamless handoff after acquiring the newsletter
• 🧑‍💼 Being accountable to subscribers who rely on the newsletter for jobs

00:00 Acquiring a newsletter

08:05 Researching solo

14:10 The differences in journalism in the UK vs US

15:35 Growing a newsletter to 10k+ subscribers

23:18 Work/life balance as a creator

29:23 Premium subscribers and monetisation

33:04 Keeping a distance from your audience

36:50 Advice to creators, from a creator

41:05 The future of TWJN

45:30 The biggest regret as a creator

Intro music produced by J. & Doug Organ.

Today’s guest is Peter Ramsey. He runs Built for Mars, a UX consultancy and content library he started almost by accident after the company he founded during university was acquired in 2018. I was drawn both to his story and the undeniable quality of his content.

Peter is a rare type — an obsessively detailed researcher but not pedantic about it. He’s just as talented at spinning that research into fun, useful, and easy-to-digest narratives.

In this episode:

00:00 Who is Peter Ramsey and what is Built for Mars

05:30 The MrBeast of UX

09:47 Using every bank in the UK

13:19 Who are Built for Mars readers?

16:30 How Peter monetizes the newsletter

19:30 Is the website fantastic, or does it suck?

25:20 Why start a newsletter?

27:43 The stats

30:23 Peter’s most viral posts

31:40 Why Peter hates social media

33:38 The gamification of education sites/apps

38:11 The different types of written content

40:46 Growing an online business

47:00 The future of Built for Mars

Intro music produced by J. & Doug Organ.

Today’s guest is Caitlin Murray, better known by her Instagram handle @bigtimeadulting. After her son was diagnosed with leukemia in 2016, she started writing about it to friends and family — nearly 8 years later, she has 1.4 million Instagram followers. It’s a great story.

In today’s episode:

00:00 The origin story

05:50 How to gain over 1 million followers

10:15 The 4 chapters of @bigtimeadulting

14:15 Turning Instagram into a business

19:25 Building a positive community

24:08 Growing an Instagram following, organically

29:22 Podcasting is hard

33:41 Monetizing as a creator

38:31 Starting and building a newsletter

47:45 Having multiple monetization streams

51:53 Advice lightning round

Intro music produced by J. & Doug Organ.

Today's guest is Tyler O’Shea, creator of Joker Mag, a website and newsletter about sports underdogs. He started the project in that “what am I gonna do with my life” period after graduating college. Nearly 7 years of posting later, he’s still doing it as a side project, but it’s also led him to a career in SEO (search engine optimization).

In this episode, we talk about:

• 🐶 Learning how to write for the internet
• 🌟 What writing and posting content online can do for you
• 🔎 How posting led Tyler to discover and start working in SEO
• 📱 How to figure out which social media platform is most useful for you

Note: Yes, Francis' sound is slightly off in this episode. Good thing Tyler does most of the talking!

00:00 Tyler’s motivation and the mentality of a creator

05:37 The inspiration to start writing

08:40 Is Google’s AI killing SEO ?

11:36 The average Joker Mag reader

14:44 Finding amazing sports stories

18:37 How to grow a loyal audience

23:25 How much time does it take to grow a newsletter?

27:38 The different monetization channels

32:03 Hiring other writers

37:21 SEO tips: How to make your website the best

39:06 Advice for creators

43:40 Future goals

49:30 Quick Q&A

Intro music produced by J. & Doug Organ.