ARR Milestones, Cohort Differences, and Perseverance

CJ and Kyle kick things off celebrating their global rise to fame (#10 in Croatia) before diving into what it really takes to grow a podcast from scratch, why second place doesn’t matter in a winner-take-all world, and how only 2% of startups ever make it to $25M ARR—plus a Business Blunders detour into panels nobody wants, children’s play-place pricing gone wild, and the strange genius of The Wonder.

Timestamps:

00:00 Intro: Croatia & Rankings

01:10 #10 in Croatia

02:30 Growing the Pod

04:05 Building an Audience

05:22 Why Most Pods Die

06:30 Finding Audience Fit

07:42 Breaking Into the Top 4

09:15 No Guests, No Problem

10:20 LinkedIn Beats TikTok

11:18 Apple, Spotify, YouTube

12:32 Top of Funnel Focus

14:05 Referral & SEO Plays

16:00 Second Place Doesn’t Count

17:25 Winner Take All Economics

19:10 Uber vs Lyft Example

21:05 The 2% That Make It

23:12 Be Niche or Die Trying

25:00 Pick Fewer Channels

27:50 Harder Than Harvard

30:40 Business Blunders

41:55 Pricing in the Real World

46:00 Wrap Up: Mostly Memberships

Episodes Referenced:

How to Give a Killer Keynote (Without Having a Panic Attack)

996 Culture, Exploding AI Bills & SaaS Chaos

Why Founders Are Posting Sad Dinners

Cowboy Forecasting: The Power of Fast Informed Estimates on the Back of an Envelope

5,762 Job Applications. Zero Offers.

Links:

https://medium.com/@alasagilbert/90-of-podcasts-only-survive-their-first-3-episodes-heres-how-to-keep-yours-strong-sold-4e4466585b52

https://web.archive.org/web/20060328070331/http://backend.userland.com/discuss/msgReader%24108?mode=day

https://en.wikipedia.org/wiki/History_of_podcasting

https://www.patriots.com/audio/unfiltered-podcast-archive

https://topline.beehiiv.com/p/the-era-of-haves-and-have-nots

https://substack.com/@kylepoyar/note/c-159017468?

https://www.linkedin.com/posts/kyle-poyar_new-data-from-6525-saas-startups-its-easier-activity-7382033365652348928-Afoo

https://thewonder.fun/memberships/

https://www.park9dogbar.com/