The Nathan Barry Show – Details, episodes & analysis

In today’s episode, I sit down with investor, entrepreneur, and content creator, Sahil Bloom (in front of a live audience) to unpack the key strategies and lessons that will help you achieve longevity and sustainability in the creator economy.

Sahil has had a fascinating journey, transitioning from the world of private equity to making a name for himself in the creator economy (his bi-weekly newsletter alone has more than 400K subscribers). Upon entering this new sector, Sahil found himself occupied with the question of how to ensure longevity and set about putting together the ideal business operating system for content creators. 

In today’s conversation, you’ll get a behind-the-scenes look at how Sahil built a thriving ecosystem as a content creator by acquiring businesses that would resonate with his audience and partnering with the right collaborators. You’ll also hear Sahil’s answers to live audience questions where he sheds light on finding the right partner, knowing when to pivot, and the future of the creator ecosystem.

In this episode, you'll learn:

• How Sahil became one of the first people to popularize the use of long-form on Twitter
• Why to focus on building an audience with whom your work resonates rather than chasing vanity metrics
• How to figure out if you're creating inspiration-driven content operation-focused content (and where you lie on the spectrum)
• How to escape the need to create new content daily by putting strategies in place
• How to use flywheels as the operating system for your business
• How to find the right collaborators
• How Sahil uses agencies to turn cost centers into profit centers
• When to pivot on a project or company
• Habits for creating and managing your time as a creator

Links & Resources:

The Sweaty Startup

Wait But Why

Justin Welsh

Tim Ferriss

Sahil Bloom Links:

Sahil’s website

Follow Sahil on LinkedIn

Follow Sahil on Twitter

Follow Sahil on Instagram

Follow Sahil on YouTube

Follow Sahil on TikTok

Subscribe to Sahil’s newsletter

Today, I talk to Darrell Vesterfelt, who is a longtime friend who helped grow ConvertKit in our craziest growth times (from $100,000/mo when he joined to $500,000/mo in just over a year).

Darrell is one of the best marketers I know. He is the Founder and former CEO of Good People Digital, the Co-Founder of Homestead Living, and Co-Founder and COO of the School of Traditional Skills.

In this episode, Darrell breaks down the goal and execution of an online summit that accumulated an astonishing 101,000 attendees as a brand-new brand! Tune in to find out why you can’t have a marketing strategy without value and vice versa.

In this episode, you'll learn:

• Darrell’s transition from New York to homestead; how his marketing skills translate to homesteading.
• The importance of authenticity in the homesteading world.
• A rundown of Darrell’s various businesses.
• The publication and publishing house, Homestead Living: what inspired it and where it’s going. 
• The structure, marketing strategy, execution, and conversion rate of the School of Traditional Skills Summit.
• The best marketing strategy according to Darrell.

Links & Resources:

Homestead Living

Homestead Living on Instagram

School of Traditional Skills

Homesteading Family

Good People Digital

Everything Worth Preserving

Darrell Vesterfelt Links:

Darrell’s website

Follow Darrell on LinkedIn

Follow Darrell on Twitter

Follow Darrell on Instagram

In this episode I talk to Justin Moore. Justin is a Sponsorship Coach & the founder of Creator Wizard, a school & community that teaches you how to find & negotiate your dream brand deals.

In today’s episode Justin reveals how narrowing in on sponsorship coaching was a huge boost for his business. We talk about him growing multiple audiences between different YouTube channels (he and his wife, April, have well over a million combined followers on YouTube).

My favorite part of the episode is when we dive into From Boise, my side project newsletter. Justin breaks down what we’re doing wrong with sponsorships, how we should be selling them, and how there’s quite a bit more to be earned. We also dive into the way he runs his newsletter and how he’s grown it.

In this episode, you’ll learn:

• The differences and similarities between sponsorships and newsletters
• Justin’s tips for starting your newsletter and getting traction
• How a simple change in Justin’s Twitter headline led to amazing growth for his brand
• Why you need to charge your sponsors different amounts

Links & Resources

• Deepak Malhotra: Negotiation Genius: How to Overcome Obstacles and Achieve Brilliant Results at the Bargaining Table and Beyond

Justin Moore’s Links

• Justin’s website
• Justin's newsletter
• Follow Justin on Twitter
• Join Justin’s group on Facebook
• Justin’s TikTok
• Justin is on Instagram
• Check out Creator Wizard on YouTube
• Trending Family
• AprilJustinTV on YouTube

In this episode I’m joined by Kaya Yurieff. She is the Creator Economy Newsletter writer for The Information. It’s the publication I read when I want to know what’s going on in startups and funding, learn about Spotify’s latest launch, find out what’s going on with Instagram, and things like that.

Kaya has a great approach. I love her writing. I love the way she profiles both individual creators and the moves happening from big businesses in the creator space.

We talk about her writing process and her system for publishing four days a week. We talk about how they’ve grown the newsletter and what they pay attention to for monetization. We also talk about what it means to be a creator through crises like the pandemic, the social justice issues of the last few years, and now the war in Ukraine.

In this episode, you’ll learn:

• Tips for finding your niche in a crowded field
• How to get more paid subscribers
• Benefits of adding visual content to your newsletter
• How to balance free content and paid content

Links & Resources

• Embedded
• Kate Lindsay’s post on Embedded: You don't need to post through a crisis

Kaya Yurieff’s Links

• The Information’s Creator Economy Newsletter
• Follow Kaya on Twitter

In this episode I talk to Wes Kao, co-founder of altMBA. Her latest startup is called Maven, and it's all about cohort-based courses.

Wes is fantastic at course design. Before Maven, she did a bunch of amazing things working with a lot of different creators.

We talk about the State Change Method, which is something I use to make my presentations much more interesting. We talk about building an audience on Twitter. We also talk about course design, cohort-based courses, and a lot of other fun things.

In this episode, you’ll learn:

• Tips for writing short-form content that boosts engagement
• A big advantage Twitter gives you over other platforms
• How to know if your content is ready to publish
• Why cohort-based courses are so lucrative

Links & Resources (H5)

• Seth Godin
• altMBA
• Gagan Biyani

Wes Kao’s Links (H5)

• Maven
• Wes’ website
• Follow Wes on Twitter
• Wes’ blog post: Course Mechanics Canvas: 12 Levers to Achieve Course-Market Fit
• Wes’ blog post: The State Change Method: How to deliver engaging live lectures on Zoom

On today’s show I’m talking with Brennan Dunn. Brennan is a longtime friend. He's been around since the very early days of ConvertKit. He helped me review pull requests from our very first developers.

These days Brennan is an expert in all things email marketing and automation. He’s fantastic at segmenting lists, personalizing content, using Liquid, and other advanced techniques to create a custom experience for subscribers.

We talk about some of the ways you can gradually get into automation. We go over some examples of the advanced things Brennan does with Liquid and snippets to create custom experiences for subscribers. We also talk about how you can earn more money from email with these systems, and much more.

In this episode, you’ll learn:

• Strategies for tailoring your website to boost engagement & sales
• How to free up more time so you can focus on growing your audience
• Brennan’s tips for creating and sharing the right content for your audience
• How to make your repurposed content feel fresh & relevant

Links & Resources

• ConvertKit
• Shopify’s Liquid
• RightMessage

Brennan Dunn’s Links

• Create & Sell
• Creator Email Template Pack
• Double Your Freelancing
• Brennan’s book: Double Your Freelancing Rate
• Mastering ConvertKit
• Follow Brennan on Twitter

In this episode I talk to Sahil Bloom. This is Sahil’s second time on the show. He’s doubled his audience from an already large number since then, and he’s now a full-time creator.

Sahil is someone I’d love to have on the show every six months or every year. He’s putting out incredible content. I’ve probably learned more from Sahil in the last few months than I have from any other person.

We talk about Twitter growth, monetization, growing a podcast, and newsletters. I also try to sell him on switching to ConvertKit. You can be the judge of how well I did to convince him.

In this episode, you’ll learn:

• Two game-changing habits that can lead to big results
• How Sahil categorizes his content for more engagement
• Sahil’s strategies for growing a new podcast
• How Sahil monetizes his newsletter

Links & Resources (H5)

• James Clear
• Shane Parrish
• The Generalist (Mario Gabriele)
• Greg Isenberg
• The Tim Ferriss Show, episode 362: Talent Is the Best Asset Class — Graham Duncan

Sahil Bloom’s Links (H5)

• Follow Sahil on Twitter
• Listen to Sahil’s podcast, Where It Happens
• Visit Sahil’s website

On today’s show I talk to Isa Adney, a resident storyteller at ConvertKit.

Isa came to ConvertKit as our webinar producer. You get to hear the arc of what she was doing before, how she joined the team, and how it morphed into her current role.

Isa is very good at systems. She shares how she uses systems to free up time for creative activities. We also talk about reusing content, and how to create systems and flywheels to make one piece of content work across many platforms.

In this episode, you’ll learn:

• How to connect with popular creators you admire
• The best medium for building a relationship with your audience
• Isa’s advice for hosting workshops and webinars
• How Isa utilizes systems to create content across multiple mediums

Links & Resources (H5)

• ConvertKit
• ConvertKit podcasts
• Don Hahn: Brain Storm: Unleashing Your Creative Self
• Kimberly Brooks
• The Nathan Barry Show 053: Kimberly Brooks – Taking Intentional Breaks To Reignite Creativity
• Harlem's Fashion Row (HFR)
• The Nathan Barry Show 026: Khe Hy – How You Can Do $10,000/Hr Work
• ConvertKit Creator Stories

Isa Adney’s Links (H5)

• Follow Isa on Twitter
• Isa is on Instagram
• Follow Isa on TikTok

In this episode, I talk to Ellen Hyslop, Co-Founder of The Gist.

The Gist is a newsletter all about sports, written entirely by women. Ellen and her co-founders have scaled a massive team to 20 people. They’ve grown The Gist to almost 400,000 subscribers, and they’re earning fantastic revenue from it.

Ellen talks about how they grew The Gist in the early days. She also talks about their process of testing, how they launched with a launch party, and a bunch of other things.

In this episode, you’ll learn:

• How to get subscribers when you’re first starting out
• Why you need to create a style guide for writing your newsletter
• Tips for growing your newsletter to 400K subscribers
• When niching down can lead to more revenue

Links & Resources

• The Gist Co-Founder Jacie deHoop
• The Gist Co-Founder Roslyn McLarty

Ellen Hyslop’s Links

• The Gist website
• The Gist newsletter
• The Gist of It podcast
• Follow Ellen on Instagram

In this episode I talk to Rachel Rodgers. Rachel is an attorney turned business coach. She’s someone I’ve admired and respected for a long time. She helps small business owners understand contracts and the legal side of running a business, and helps them scale their business.

Rachel is a lot of fun, and she’s brilliant at business. She’s my hero because of the way that she approaches scaling a massive and successful business, and how she thinks about brand and everything else.

On today’s show we talk about why business partnerships are a bad idea. Rachel shares her keys to building a successful membership community, and the benefits of publishing a book. We also talk about why you should take expensive vacations, how to build a great team, and much more.

In this episode, you’ll learn:

• Why offering more products can hurt you in the long run
• Rachel’s clever method for scaling a business
• The relationship between current events and a successful creator business
• How Rachel builds an effective team

Links & Resources (H5)

• Nathan Barry: Authority
• Denise Duffield-Thomas
• ConvertKit

Rachel Rodgers’ Links (H5)

• Hello Seven
• The Hello Seven podcast
• We Should All Be Millionaires: The Club
• We Should All Be Millionaires: A Woman’s Guide To Earning More, Building Wealth, and Gaining Economic Power
• Small Business Bodyguard
• Follow Rachel on Twitter
• Rachel is on Instagram