Patrick O’Shaughnessy, the visionary behind the podcast Invest Like the Best and co-founder of Colossus, shares his journey from finance to media. He reveals how his podcast blossomed into a thriving network, producing diverse investing shows. The discussion highlights innovative monetization strategies, the significance of audience engagement, and exclusive networking events for investment professionals. O’Shaughnessy also emphasizes quality over quantity in content creation, aiming to build a self-sustaining ecosystem for listeners and sponsors.

Professional travel photographer Gary Arndt pivoted to podcasting during the pandemic, creating Everything Everywhere with 1.5M monthly downloads. He discusses audience building, episode ideas, and leaving social media. The podcast covers diverse topics beyond travel, uses SEO-friendly name for content variety, and focuses on daily scripted episodes for search visibility and revenue growth through affiliate advertising and sponsorships. Arndt shares plans for business expansion with tours and merchandise.

Jared Newman, Founder of Cord Cutter Weekly, discusses launching his newsletter during the streaming boom, gaining 32,000 subscribers. He shares insights on monetization, strategies for promotion, and potential transition to full-time newsletter growth.

My newsletter: https://simonowens.substack.com/   Today, the personal finance content niche is absolutely ginormous. You can’t open up YouTube, TikTok, or Instagram without encountering an influencer who gives advice on how to make and save money.   Today’s guest Philip Taylor anticipated this content explosion all the way back in 2011. That’s when he launched FinCon, a conference specifically designed for personal finance content creators. That first year he attracted around 250 attendees, but over the next decade it grew into the largest conference in this niche, attracting over 3,000 attendees a year.   In our interview, Philip walked us through how he got into the personal finance space, his strategy for growing the conference, and his ambitions for launching similar conferences in other niche categories.  

My newsletter: https://simonowens.substack.com/   I’m sure just about everybody has had the experience of looking at a celebrity memoir and wondering: did they actually write that? In many cases, they didn’t, at least not by themselves. There’s actually an entire shadow economy of ghost writers who do the bulk of the work on these books – not just for celebrities, but all kinds of public figures ranging from big-name CEOs to politicians.   But how does one go about hiring a ghost writer? And what’s it like to work with one? To answer these questions, I turned to Dan Gerstein, the founder of Gotham Ghostwriters, an agency that specializes in connecting clients to professional ghostwriters.  

Ben McCarthy shares how his blog on Salesforce evolved into a booming media company with 1M pageviews/month. He delves into monetization strategies, niche content creation, team growth, and future plans for expansion into other cloud technologies.

Joe Pulizzi, entrepreneur, shares insights on building successful media companies, transitioning to the creator economy, and the growth strategies behind his newsletter and conference business. He discusses the importance of networking, event planning, and sponsorship dynamics for content entrepreneurs.

Brad Hargreaves, founder of a rental property management company, discusses his transition to launching a paid newsletter focused on real estate investment. He explains why he chose a paid-only model, differentiates his content, and shares plans for a data platform. Topics include challenging transitions, growing a subscription-based newsletter, diversifying content, and building a real estate developer database.

My newsletter: https://simonowens.substack.com/   I spend most of my time on this show interviewing entrepreneurs who founded English-language media outlets – mostly because that’s the only language I speak – but that doesn’t mean I’m not interested in the media ecosystems from other regions in the world. That’s why I was super excited to talk to Andreas Sator, the host of one of the most popular podcasts in Austria.   Andreas got his start at a major newspaper, and after a few years at the outlet, he got to experiment with writing an explainer journalism column about personal finances. He found this sort of reporting to be much more enjoyable, so in 2018 he launched a podcast that roughly translates to “Explain The World to Me.”   In our interview, we discussed the Austrian podcast market, how he monetizes the podcast, and why he decided to launch a new show about climate change.  

My newsletter: https://simonowens.substack.com/   Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump into 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:   Which media companies are succeeding with native advertising The best ways for media outlets to run live events How to grow your audience in a world where Google and Facebook are sending less and less traffic What a Substack advertising platform would look like.