Henry Winslow is the founder and editor of Tricycle Day, a twice-weekly newsletter that distills psychedelic research, policy, and culture into a 10-minute read.

In just two years, Henry’s grown an audience of over 65,000 subscribers by combining brute-force outreach, diversified revenue streams, and community building.

In This Episode, We Cover:

(05:39) Evolving Tricycle Day’s Business Model

(08:04) Growing Subscribers with Brute Force

(11:08) Newsletter Formats: Roundup vs. Q&A

(16:36) Turning Readers into a Community

(22:19) Upstream Marketing: From Problem to Solution

(28:06) Email Deliverability & Censorship Battles

(34:00) Customizing Your Community Platform

(39:22) Using Events to Build Your Brand

(45:01) The MDMA Therapy Approval Rollercoaster

Dan Barry’s Ad Sales as a Service helps media brands (especially newsletters) land more direct sponsorships and ad deals.

In this episode, Dan reveals the three biggest pitching mistakes and their simple fixes that will maximize your sponsorship ROI.

Chapters:

(00:00) Three Sponsorship Mistakes to Avoid

(05:33) Why Newsletter Sponsorships Stand Out

(10:53) Earning Sponsor Trust Quickly

(20:39) The Best Time to Monetize

(26:07) Essential Sales Skills for Sponsorship Pitches

(31:35) Boosting CPMs

(37:02) Low-Budget Marketing Hacks

(43:33) Crafting High-Conversion Lead Magnets

Nic Conley built his B2B sales newsletter, The Follow Up, to 7,000 subscribers in only 2 weeks. We sat down with Nic to break down exactly how he did it.

Chapters:

(02:04) Launching The Follow Up with the "Early Referral" Experiment

(07:42) Scaling with Paid Ads: Facebook & Twitter Tactics

(10:33) Owning Local Distribution

(21:22) Learning From Reader Replies

(30:00) Debriefing Virality vs Audience Fit

(35:00) Newsletter Advertising for Brand Marketing

(42:11) Content Lessons from the Wolf of Wall Street

Learn More About Orbit Marketing:

→ Visit Our Website: https://orbitmarketing.io/

→ Book A Call: https://api.leadconnectorhq.com/widget/booking/onkh0t7y3dIlC2Njpybl

→ Join Our Newsletter: https://newsletter.orbitmarketing.io/

Connect with Nic Conley:

→ Nic Conley's LinkedIn: https://www.linkedin.com/in/nicholasaconley/

→ Nic Conley's IG: https://www.instagram.com/itsnicconley/

→ Nic Conley's Twitter: https://x.com/niconley

→ Nic Conley's YouTube: https://www.youtube.com/channel/UCj88BHCCZgiBYNv4QryNEdQ

Read The Follow Up:

→ The Follow Up's LinkedIn: https://www.linkedin.com/company/the-follow-up/

→ The Follow Up's Website: https://www.jointhefollowup.com/subscribe

Jordan Mix is the Operating Partner at Late Checkout, a holding company that creates, grows, and buys "community-based" products.

In This Episode We Cover:

(05:16) Simple, Effective B2B Newsletter Playbooks

(09:49) High-ROI Outreach (“Shake the Tree”)

(12:40) Monetizing Micro-Lists (200 subs → $10k+)

(14:50) The Power of Parasocial Relationships

(17:36) Why Making Content Makes You Better At Sales

(27:30) Experimentation vs Focus

(30:05) Permissionless Projects & Cold DMs

(33:30) Using Free Work to Reduce Customer Acquisition Costs

(38:52) Building Engaged Communities with AI

Learn More About Orbit Marketing:

→ Visit Our Website: https://orbitmarketing.io/

→ Book A Call: https://api.leadconnectorhq.com/widget/booking/onkh0t7y3dIlC2Njpybl

→ Join Our Newsletter: https://newsletter.orbitmarketing.io/

Connect with Jordan Mix from Late Checkout:

→ Late Checkout: https://www.latecheckout.studio/

→ Late Checkout LinkedIn: https://www.linkedin.com/company/late-checkout/

→ Jordan's LinkedIn: https://www.linkedin.com/in/jordan-mix1/

→ Jordan's Twitter: https://x.com/jrdnmix

Watch on Youtu

Ariel David credits Upward News's success to one powerful strategy: building an engaged, loyal email list.

As the founder and Editor-in-Chief of Upward News, Ariel has grown the platform to over 400,000 readers across social media, providing must-know U.S. news and insights.

In This Episode We Cover:

((00:00) The Power of an Owned Audience

(06:37) Building Trust in Independent Journalism r

(20:02) Challenges in Journalism and Censorship

(26:34) The Evolution of Instagram Growth Tactics

(33:07) Understanding Lead Indicators in Social Media

(39:45) Bias in The New York Times Opinion Section

(46:30) Unexpected Benefits of Content Creation

(53:18) Passion Over Networking

Gui Costin is the Founder & CEO of Dakota, an expert in fundraising, and a trusted coach for investment firms.

Dakota specializes in helping boutique investment managers raise capital and grow their businesses, providing services and software that have contributed to raising over $30 billion since 2006.

In This Episode We Cover:

(00:00) Why Sales is Emotionally Challenging

(03:02) Mastering Cold Outreach

(06:09) Gui’s Core Principles

(09:28) The Importance of Believing in Your Product

(12:29) Understanding Millennial Buying Behavior

(15:49) Strategies for Creating a Valuable Email Newsletter

(25:36) Networking Strategies

(28:49) Leveraging SEO

(35:18) Lessons Learned from Russell Brunson

Learn More About Orbit Marketing:

→ Visit Our Website: https://orbitmarketing.io/

→ Book A Call: https://api.leadconnectorhq.com/widget/booking/onkh0t7y3dIlC2Njpybl

→ Join Our Newsletter: https://newsletter.orbitmarketing.io/

Connect Gui Costin and Dakota:

→ Dakota's Website: https://www.dakota.com/

→ Dakota's LinkIn: https://www.linkedin.com/company/dakota-about/

→ Gui's LinkIn: https://www.linkedin.com/in/guicostin/

→ Gui's Website: https://www.guicostin.com/

Dickie Bush is the Co-Founder of Ship 30 for 30, Premium Ghostwriting Academy (PGA), and Write With AI, where he helps freelance writers, ghostwriters, and entrepreneurs scale their writing businesses with cutting-edge strategies and tools. At PGA, Dickie equips writers to become premium ghostwriters, land high-value clients, and build thriving ghostwriting agencies. With Write With AI, he shares actionable insights on leveraging AI platforms like ChatGPT to become your own Digital Writing Assistant.

In this video, Dickie dives into the latest trends in digital consumption growth, strategies for differentiating in saturated markets, and optimizing content for revenue growth. He also shares practical tips on building a successful newsletter, managing financial risks in entrepreneurship, and creating social proof for online courses. Dickie emphasizes the power of consistency in mentorship, personal habits in driving sales success and using internal insights to craft impactful content.

If you want to improve sales funnels, tackle cold traffic, and overcome ad fears, this episode offers insights to scale your business and seize new opportunities.

Chapters:

(03:47) Trends in Digital Consumption Growth

(07:47) Strategies for Differentiating in Physical Delivery Markets

(11:47) Optimizing Content for Revenue Growth

(15:44) The Power of a Weekly Newsletter

(19:40) Navigating Financial Risks in Entrepreneurship

(23:29) Building Social Proof for Online Courses

(31:28) The Importance of Consistency in Mentorship

(35:18) The Role of Personal Habits in Sales Success

(39:12) Leveraging Internal Insights for Content Creation

(43:11) Optimizing Employee Efficiency and Responsibilities

(50:46) Sales Funnel Metrics

(54:53) The Challenges of Selling to Cold Traffic

(59:07) Overcoming Fear of Paid Advertising