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Ready to turn a travel side-project into a full-time, six-figure newsletter? In Episode 5 of the LetterStack Podcast, Renga chats with Chris Cerra, founder of RemoteBase and Digital Nomad Trip Reports, about bootstrapping a lean media empire (and why he runs it under the delightfully named Mad Banana Media).
What you’ll learn:
How Chris went from a niche UK tax job ➜ remote-work globetrotter ➜ newsletter founder
Launch playbook: 112 Slack-group subscribers on day 1 → the slow grind to 10 K+
Free vs Paid vs Sponsorships: why he swings the “revenue pendulum” toward sponsors
Platform wars: Mailchimp pains, Beehiiv migration hacks and running two ESPs at once
Content ops: sourcing Airbnb-style long-stay deals and crowd-sourcing trip reports
Buying a small list? Chris’s real-world micro-acquisition story (and what he paid)
The “banana” brand strategy & his 3-tier consulting offer (audit, strategy, email-doctor)
Starting today: Chris’s advice for building the next RemoteBase in 2025–26
Timestamps:
00:00 – Intro & name pronunciation (it’s Chera!)
02:12 – Life before RemoteBase: from marketing grad to tax-tech desk job
03:54 – First taste of remote work (2016) and the travel itch
05:27 – Launching RemoteBase inside a Slack community (112 subs day 1)
07:42 – The very slow road to 1 K & why that was OK
09:09 – Quitting the day job: part-time → “burn the boats”
12:24 – ESP saga: Weebly → Mailchimp → Beehiiv (free first, paid later)
15:14 – Free list vs RemoteBase Premium numbers & revenue split
17:17 – How long-stay deal curation actually works (team, tools, “magic”)
22:35 – Trip Reports: community-generated content + list micro-acquisition
28:05 – What is Mad Banana Media & the “Email Doctor” service?
34:03 – Chris’s playbook for new creators: start organic, engage 1-on-1, keep it fun
👉 Subscribe to LetterStack for operator-level interviews on building, monetizing, and scaling newsletters.
🌐 Explore RemoteBase deals → remotebase.co
🍌 Mad Banana Media consulting → madbananamedia.com
📩 Digital Nomad Trip Reports → tripreports.remote-base.co
#newslettergrowth #digitalnomad #remotework #RemoteBase #Beehiiv #MadBananaMedia #LetterStackPodcast
5 episodes
