In 2023, I fulfilled a long-term dream of learning to fly, bought my own airplane, started a new company, bought another company, captained a 50 foot sailboat in the Caribbean, took a sabbatical, added more $7.5 million in annual revenue to ConvertKit, and had a whole ton of fun.  Let’s dive in.  ConvertKit In January of this year, we celebrated ConvertKit’s 10th birthday on the beach in Mexico. Hilary flew down, the team made a wonderful video, and we had a big party. In the last decade, the company has grown from a way to fix what frustrated me with MailChimp to the platform poweri ..read more

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 ..read more

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 w ..read more

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 o ..read more

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 phil ..read more

2022 was a good year, but a busy year. Far too busy. I found myself overly involved in the details of the business and handling many responsibilities I needed to delegate. All of that took a toll on me. We had some key executives leave (more on that below), and it left me in charge of doing too many different jobs. A lot of energy went into hiring the right new people for these leadership roles. It was time-consuming work, but necessary to make 2023 look a lot more calm in comparison. ConvertKit 2022 was a big year for ConvertKit. Here are a few of numbers: We grew ARR 15% from $29.14 million ..read more

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 p ..read more

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 usin ..read more

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 subscribe ..read more

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 Frame. 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 tha ..read more