New Media

Ryan Deiss, founder and serial entrepreneur in digital marketing and education, explains why he shut an eight-figure course business after an 80% sales drop. He argues AI is outcompeting courses and shows alternative monetization: build owned media, sell AI trained on your IP, productize services, and scale revenue with events, sponsorships, and licensing.

Brian Morrissey, founder of The Rebooting and former Digiday editor, offers big-picture media instincts. He outlines three media archetypes and why balance matters. He explains why many streaming clones will fail, how webinars and podcasts build real connection, and why SMS and collecting phone numbers are surprisingly strategic tools.

Jonathan Barshop, podcast growth strategist who engineers viral clips. Alyssa Dulin, email deliverability lead focused on AI and inbox health. Ethan Brooks, local newsletter founder who monetizes via services and events. They discuss monetizing local newsletters with services, how AI reshapes deliverability and inbox curation, and growth tactics that make podcasts and clips spread in 2026.

They discuss using AI tools to write marketing emails, subject lines, and landing page copy. New AI-powered workflows, prompts, and tools built into their program are outlined. Practical resources like swipe files, templates, generators, and ad creative are highlighted. They also explain limited-time pricing, enrollment dates, and why there’s a special sale.

Neville Medhora, founder of Swipefile and copywriter behind AppSumo wins, shares his journey from high-school dropshipping to building a growing swipe library. He discusses why his Copywriting Course faded while Swipefile thrives, how he structures high-value sponsorships, and his content workflow that turns swipes into newsletters and social posts.

Walker Deibel, author and acquisition entrepreneur who built Buy Then Build and huge newsletters. He recounts grassroots book-launch tactics, turning a book into courses and communities, and how an email list enabled a $4M+ capital raise in hours. He also explains frameworks for standout content, building private-market investing communities, and why newsletters are the most powerful business asset today.

They unpack OpenAI’s surprising nine-figure acquisition and why talent mattered more than audience size. They debate media as a PR play and the risk to editorial independence under corporate ownership. They highlight TBPN’s rapid growth tactics like daily live shows and clip strategy. They explore whether media buys reshape creator incentives and acquisition playbooks.

Taylor Cromwell, writer of Creator Diaries who tracks creator-to-founder shifts, joins to unpack what makes creator-led media ready for acquisition. They discuss the Starter Story case, how to de-risk a brand beyond a single face, the power of IRL events, and practical moves like building an email list and diversified revenue streams.

Chenell Basilio, newsletter growth strategist and author of Growth in Reverse, shares her 30 Days of Growth playbook. She breaks down cross-promotion mechanics, pop-up newsletters for re-engagement, and why repeat frameworks make creator work scalable. They also explore SMS, live streaming, YouTube, and the sustainability of creator empires.

Brent Davidson, founder of the U.S. Heat Pump Summit and events entrepreneur for HVAC and plumbing pros, explains how he built a 500-person trade show from scratch. He covers revenue models like booth and sponsor pricing, designing attendee flow and buyer-seller matchmaking, using media and newsletters to drive attendance, influencer strategies, and scaling trade events into larger cross-trade marketplaces.