Pursuit

Case Kenny launched Pursuit four years before this interview as a traditional online publisher monetized through programmatic advertising and banner ads. However, he watched the digital publishing landscape shift dramatically as Facebook, Instagram, and Google algorithm changes made direct advertising increasingly unreliable. After observing successful email-only models from competitors like The Hustle and Morning Brew, Case realized he didn't want to "build on rented land." He saw an opportunity to leverage his most engaged asset—his email list—and pivot the entire business to a daily newsletter focused on self-development content.

The transition wasn't just a technical pivot. Case moved from a contributor-driven model (with over 600 contributors including Gary Vaynerchuk and Mark Manson) to a personal, first-person voice. He became the sole writer, publishing 400-500 word daily emails about self-development. This required him to invest heavily in content creation—spending time writing, podcasting, and speaking, then having a single editor in Chicago refine his work. By the time of the interview, Pursuit had 172,000 subscribers on a simple landing page with one option: sign up for the email.

Case built direct relationships with advertisers rather than using email marketplaces. He developed a CPV (cost per thousand opens) pricing model at $30-40 per 1,000 opens—a competitive rate for an emerging media company. Within eight months, he'd secured over 40 brand sponsorships including Eight Sleep, Burrow, Casper, The Points Guy, MVMT Watches, and Mack Weldon. The model worked because email proved to have strong ROI; when Case asked brands about their highest-ROI channels, they consistently said podcasting and email. Inbound interest was strong, and he was strategic about inventory—never taking so much from one brand that he'd oversaturate his audience.

Case's most effective tactic was obsessive list hygiene and subscriber segmentation. He maintained a 39% open rate by actively purging inactive subscribers—a strategy most publishers avoid. He used Active Campaign's scoring system to segment subscribers, only exposing new subscribers to advertisers after 28 days and a certain engagement score. This meant a 60,000-person open on a single day could generate roughly 1,200 advertiser clicks at 2% click-through rate. He also capped advertiser exposure at 1-3 sponsorships per brand per month, spreading demand across Instagram (150,000 followers), his podcast, and a private ambassador group. Most advertisers prepaid for sponsorships based on projected opens, giving Case immediate cash flow and inventory control.

In 2019, Pursuit had just completed its first full year with approximately $100,000 in revenue from sponsorships alone. Case projected $800,000-$900,000 for 2019 by diversifying beyond ads: he planned to launch events in Chicago, LA, and New York (with low initial overhead), then develop digital products for his audience. The two-person team—Case and one Chicago-based editor—operated as a lean lifestyle business. Case deliberately kept headcount minimal, viewing Pursuit as a three-to-four-person operation maximum. His willingness to discount sponsorship rates early and reinvest in audience understanding positioned him to eventually monetize products directly to his highly engaged subscriber base of young professionals seeking self-development.