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 today’s episode, I’m joined by PJ Taei, Founder and CEO of Uscreen, an all-in-one video monetization platform for content creators that helps them build their brands and grow their businesses. 

The creator economy has changed a lot since PJ first founded Uscreen in 2015. And in that time PJ has managed to grow Uscreen to $20 million a year in revenue, representing sought-after clients and their channels, like Yoga with Adrienne and Justin Rhodes’s streaming platform, Abundance Plus. 

Our conversation gets into some pretty fascinating topics, like what to do when major competitors enter your field, the trial and error involved in getting your pricing right, and why true fans are so valuable for content creators looking to monetize. PJ also sheds light on what motivated him to bootstrap his company and expands on why it’s so important to stay in touch with the needs of your customers as you grow!

In this episode, you'll learn:

• How Uscreen supports creators by helping them sync their offerings on one platform.
• What helped PJ recognize the need for a service like Uscreen.
• When to fear a major competitor coming in and why you should never underestimate a small company.
• The importance of continued focus on the customer as you grow along with actionable advice on how to stay in touch with their needs.
• How to find the right balance between trial periods, free content, and attracting paying customers.
• Why PJ decided to bootstrap instead of pursuing funding and what he has learned from the experience.

Links & Resources:

Uscreen
Uscreen on YouTube

PJ Taei’s Links:

PJ’s website

PJ’s email

Follow PJ on LinkedIn

Follow PJ on Twitter

Follow PJ on YouTube 

Listen to PJ’s Podcast

In this episode, I talk to Susie Bulloch, who runs Hey Grill, Hey, which started as a wildly successful food blog (to the tune of a million dollars or more a year in revenue). Then she did something that I absolutely love: she used her online business to kickstart a physical products company. Her sauces and rubs company in the barbecue space is now about to overtake the blog in revenue.

The online world of content creation is vastly different to the product manufacturing space, and as Susie explains, she is grateful that she didn’t know too much before she made the transition. Her top piece of advice for anyone interested in doing the same thing is to make products with the intention of fulfilling a need, not just because you have an audience online. 

Susie describes herself as “terrifyingly driven,” and during our conversation, she talks about how she went from “I could never” to doing it all, the importance of celebrating business milestones, the value of having someone ask you, “Why?” regularly on your entrepreneurial journey, and her goal of increasing the representation of  women-owned brands in the barbeque space!

In this episode, you'll learn: 

• The value in working for other people before starting your own company. 
• Why it’s always worth taking the time to be grateful for the journey you are on and celebrating your achievements.
• What the life of a “terrifyingly driven” entrepreneur looks like. 
• How to build trust within your community so they are happy to pay for your offerings.
• The only piece of advice Susie would give to someone interested in transitioning from online content creation to product manufacturing. 

Links & Resources:

Hey Grill, Hey

The Grill Squad

‘The Billion Dollar Creator’

Susie Bulloch Links:

Follow Susie on Twitter

Follow Susie on Facebook

Follow Susie on Instagram

Follow Susie on YouTube

Subscribe to Susie's Grill Squad

Today, I sit down with the Head of Deliverability at ConvertKit, Alyssa Dulin, to shed some light on the often mysterious game of getting your email into the right inbox. Alyssa's expertise about what creators need to focus on and the most recent developments in the email marketing space can truly take your company's reach to the next level!

Deliverability has always been a huge part of what we offer at ConvertKit, and Alyssa unpacks the most important pieces of this puzzle, covering sender reputation, effective cadences, and setting and delivering on expectations. As with so much of our philosophy, it is all about playing the long game over short-term wins and shiny statistics. 

You’ll get a look behind the scenes at how the world of email actually operates and evolves, the important conversations that happen between providers, as well as some helpful practical tips and common mistakes to avoid. Be sure to join Alyssa and me for this illuminating chat. 

In this episode, you'll learn:

• The biggest factors that contribute to reaching your audience's inbox.
• A simple and comprehensive definition of deliverability.
• How to think about the important aspect of reputation management. 
• The real value of custom domains and dedicated IPs.  

Links & Resources:

ConvertKit's Creator Network

Eventbrite

Warby Parker

Emma

CM Group

Tim Ferriss

Susan Cain

James Clear

Bitly

Spamhaus

M3AAWG

Figma

Substack

SparkLoop

Alyssa Dulin Links:

Follow Alyssa on Twitter

Listen to Alyssa's podcast

Subscribe to Alyssa's newsletter

Today I’m talking with Thomas Frank. Thomas built a YouTube channel called College Info Geek to over a million subscribers. Since then, he’s rebranded and grown the channel to nearly 3 million subscribers. He’s also built a massive business around courses and Notion templates.

In this episode we talk about making a pivot as a creator. Thomas has an interesting and understated approach that’s worked quite well. We also talk about the Notion templates he’s selling, the YouTube productivity channel he started strictly about Notion, and how it’s driving hundreds of thousands of dollars in sales per month.

Thomas also explains why it’s easier getting started on YouTube today than it was 10 years ago, and I get Thomas’ candid thoughts on how Gumroad’s new pricing has affected his business and creators in general.

In this episode, you’ll learn:

• Why now is a great time to get started on YouTube
• How to pull off a successful rebrand of your creator business
• Why your subscriber count isn’t as important as you think
• Was Gumroad’s price increase a mistake?

Thomas’ Links (H5)

• Thomas’ website
• Follow Thomas on Twitter
• Subscribe to Thomas’ YouTube channel
• Download Thomas’ Notion templates
• Check out Thomas’ Notion YouTube channel
• Thomas’ Nebula.tv content
• Follow College Info Geek on Twitter
• Thomas’ Skillshare page

In this episode I talk to Brian Feroldi. Brian is an incredible creator in the investing space. He Tweets about money, investing, and self-improvement. He also has a free newsletter with over 40,000 subscribers.

Today Brian talks about his recent experience migrating his newsletter to ConvertKit. He’s also a member of the ConvertKit Sponsor Network. I haven’t said much about the Sponsor Network, so Brian shares how he’s using it to book sponsors.

The bulk of our conversation, however, is about Twitter and how he’s grown his account to over 400,000 followers. Brian has an interesting idea using your Twitter profile as a sales page, and he explains why conversion rates are important. We also pull up my Twitter profile and Brian gives it a tear down live on the show.

In this episode, you’ll learn:

• How to get more followers on Twitter
• Twitter profile strategies that increase your conversion rate
• Why your Tweets aren’t getting more impressions
• How to write Twitter threads that people will share

Links & Resources (H5)

• ConvertKit Sponsor Network
• Sahil Bloom
• James Clear
• Tim Urban
• Blake Burge
• Austin Lieberman

Brian’s Links (H5)

• Brian’s newsletter
• Follow Brian on Twitter
• Connect with Brian on Facebook
• Brian is on Instagram
• Check out Brian on YouTube
• Brian’s LinkedIn page

The podcast is back! Today I’m talking with Turner Novak. Turner is someone I’ve followed for a long time. He has an amazing Twitter account where he drops hilarious memes, talks about life as an investor, and makes fun of venture capitalists and founders.

He also posts deep dives on companies like Snapchat about how their earnings work, what’s going on in TikTok ads, and a lot more. It’s an interesting balance, and he does all this while investing in early-stage companies as a venture capitalist.

In today’s episode Turner and I talk about how he creates content. We get into how he uses his funnel to raise capital, and how to generate the highest return on investment (ROI) for your audience. We also talk about how he grew to 130,000 followers on Twitter, why he failed to get a job in venture capital and had to start his own firm, and how to create a successful newsletter.

In this episode, you’ll learn:

• Easy ways to grow your newsletter audience
• How Turner varies his content to get more engagement
• Why getting to know your audience is so important
• How Turner used writing to expand his venture capital network

Turner’s Links & Resources (H5)

• Subscribe to Turner’s newsletter, The Split
• Follow Turner on Twitter
• Banana Capital’s website
• Follow Banana Capital on Twitter

In this episode I talk to Katelyn Bourgoin. Katelyn is a creator and entrepreneur. She’s built several successful companies and agencies, and built a consultant company that she later sold.

We dive into why customers buy, and how to market and sell to them through the Jobs-to-be-Done framework. Katelyn has a wealth of marketing knowledge she shares with us today.

We talk about different business models. We get into why you should focus on selling checklists, cheat sheets, and outcomes rather than the traditional video courses. We also talk about how she grew her newsletter to 10,000 subscribers, and got to over 50,000 followers on Twitter.

In this episode, you’ll learn:

• Tips and strategies for acquiring more users
• A subtle mindset shift to make your marketing more effective
• What content should be free, and what should be paid for
• Why Katelyn transitioned away from launches and courses

Links & Resources

• Episode 061: Rachel Rodgers – Simple & Consistent: How To Build an 8-Figure Business
• April Dunford
• Nathan Barry: Authority

Katelyn Bourgoin’s Links

• Customer Camp
• Follow Customer Camp on Twitter
• The Why We Buy newsletter
• Jobs-to-be-Done
• The Trigger Technique
• Twitter thread about The Trigger Technique
• Follow Katelyn on Twitter

In this episode I talk to Laura Roeder. Laura and I have been friends for a long time. I’ve learned so much from her, and it’s great to have her on the podcast.

Laura started an online community and a course called Creating Fame. She’s done a bunch of stuff in the internet space. She’s one of the people who’s been doing it since the early days.

She got into software with a company called MeetEdgar, which is a social media scheduling service, and grew it into a successful company before selling it. She recently started another company called Paperbell. Paperbell is the all-in-one software that solves all the problems of running a coaching and consulting business.

There’s so much to learn from Laura. I love her direct, blunt style. She’s given me great advice over the years, and you get to tune in as we jump on a call, hit record, and start catching up.

In this episode, you’ll learn:

• Benefits of choosing a narrow niche for your business
• Common branding mistakes to avoid when starting out
• Laura’s advice for writing great copy
• Tradeoffs between hiring freelancers and employees

Links & Resources

• Mama Gena
• MeetEdgar

Laura Roeder’s Links

• Laura’s website
• Follow Laura on Twitter
• Laura is on Instagram
• Paperbell
• Follow Paperbell on Twitter
• Paperbell is on Instagram
• Follow Paperbell on Facebook
• Check out Paperbell on Pinterest