Mar 15, 2019 · 16m · top-founders
1329 His Product? A Daily Email, 172k Milennial Subscribers and $100k+ in Revenue
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Top Entrepreneurs, host Nathan Latka interviews Case Kenney, founder of the self-development newsletter Pursuit, detailing how he scaled a daily email publication with 172,000 millennial subscribers into a high-margin business pacing toward $800,000 in revenue.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 41% of the talking time here. How this is scored →
Nathan as informed peer 4.8 Guest teaching 2.0 Guest disagreement 1.0 Nathan pushing back 1.8
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 14:22 Defending a two-person lean operation
Case pushes back against the expectation of a larger overhead structure, insisting a lean two-person team is intentional for a lifestyle business.
Hardest push from Nathan ▶ 14:18 Pressing on editing team claimsNathan checks Case on his phrasing of having an editing team, forcing him to clarify that it consists of a single employee.
Biggest teaching moment ▶ 11:10 Explaining the 28-day ad gating logicCase educates Nathan on his specific list-warming funnel, explaining why subscribers do not see sponsorships until reaching engagement benchmarks after 28 days.
Nathan holds their own ▶ 12:01 Demonstrating ActiveCampaign conditional logic expertiseNathan explains the precise conditional formatting and lead scoring triggers inside ActiveCampaign before Case can explain how it works.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Episode Preview and Executive Summary | 4 | 2 | 1 | 1 | Nathan frames the episode around newsletter models like The Hustle, while Case explains his transition away from 600 contributors to a solo personal voice. The dynamic is collaborative and informational without friction. | |
| Content Creation Process and Editorial Voice | 6 | 3 | 1 | 2 | Nathan actively calculates open rates, clicks, and daily sponsorship revenue on the fly to pressure-test the unit economics. Case clarifies why he prices on cost per open rather than traditional CPM or CPA models. | |
| Brand Partnerships, Invoicing, and Direct Sales | 6 | 2 | 1 | 2 | Nathan demonstrates direct technical knowledge of ActiveCampaign's automation rules when Case describes delaying ad exposure for 28 days. Both discuss inventory scarcity and direct brand relationships smoothly. | |
| Welcome Copy, Reply Incentives, and Product Expansion | 5 | 2 | 2 | 3 | Nathan calls out Case's earlier reference to an editing team by confirming it is literally just one other person in an office. Case clarifies the lifestyle business framing and details his revenue targets. | |
| The Famous Five Lightning Round | 3 | 1 | 0 | 1 | A rapid-fire Famous Five conclusion where Case shares standard biographical and operational details in full alignment with the host. |
Statements from this episode (15)
Kenney: Email Remains One of the Most Personal Forms of Digital Communication
“I think it's one of the most personal forms of communication in this day and age where you can get DM'd anywhere. You can get hit up on LinkedIn. Like it's personal. It's literally your home address. So I firmly believe in the future of email.”
Pursuit Pivoted From 600 Contributors to a Single-Author Newsletter
“We had over 600, we had folks like Gary Vee, Mark Manson, James Altucher, big name guys, as well as anyone who can contribute open contribution.”
Latka: Every Brand Is a Media Brand That Needs Owned Channels
“So I think by the way, every brand right now, whether you're SAS company or anything, every, every brand is a media brand. And if you don't have some kind of your own channel, you're really screwed.”
Kenney: Pursuit signed over 40 brand sponsors in eight months
“We've had over 40 in the past call it eight months. Authority brands and that's, it's sponsorships, right?”
Kenney Charges Newsletter Sponsors $30 to $40 Per 1,000 Opens
“It's between 30 and 40 dollars. But we're about to increase that to be more in line with the industry, but for us being a somewhat emerging Media company.”
Kenney: Pursuit sells about 30% of its ad inventory
“We're not even selling all of our inventory right now. We're about probably selling about 30% of it and for some specific reasons.”
Kenney: Pursuit email open rate hovers around 39%
“Our open rates of brown just hovering just around 39%.”
Kenney Drives a Two Percent Advertiser Click-Through Rate on Newsletter Opens
“Really the metric that I'm interested in is advertiser click-through rate, which for us is about two, it's about two percent which is high relative, relative to my, at least my knowledge of other email newsletters.”
Brands Rank Podcasting and Email as Their Highest ROI Marketing Channels
“Anytime I ask a brand and say, Hey, what's, what's your highest ROI marketing channel? They'll usually say podcasting and then email.”
Kenney Withholds Ads From New Email Subscribers for 28 Days
“In fact, one of the things that we do is the way that our funnel works when we take a subscriber in is we don't introduce, we don't expose them to our advertisers until they've been in our funnel for at least 28 days until they hit a certain score within our s…”
Kenney: Pursuit will expand into events first, then digital products
“Probably digital and probably events. Frankly, there's a lot of interest. Everyone's always asking, oh, when are you going to do Chicago meetup, LA, New York, something like that. I think that'd be easy for us to scale it. There's no overhead initially. So we'…”
Kenney Discounts Newsletter Sponsorships to Test Internal Product-Market Fit
“One of the reasons that we're adamant about testing and we even discount our rates for brands right now is to understand what types of products resonate with our audience, whether they are digital, whether they are service or whether they are some kind of offl…”
Kenney Plans to Cap Pursuit at Four Employees for Lifestyle Business
“I've always envisioned it more of a lifestyle business. And to me, that's three, four people max. I really don't envision the need for a huge team.”