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
Hitting the primary inbox (not spam or promotions) is make-or-break for every newsletter and cold-email campaign. In Episode 4 of the LetterStack Podcast, Renga sits down with Anthony Baltodano, founder of Mission Inbox and a decade-long deliverability expert, to unpack the exact tech and tactics that keep your emails landing where they belong.
What you’ll learn:
Email Deliverability 101 – why SPF, DKIM & DMARC are the “carrier, wax-seal & security guard” of email
How to warm up domains (and why skipping it tanks reputation)
Plain-text vs HTML: balancing design with inbox placement
The hidden risks of cheap domain registrars (and why you should move DNS to Cloudflare)
Tools Tony recommends for beginners (Beehiiv + MailReach) & for scale (Mission Inbox)
Weekly health checks: simple placement tests that take 10 minutes
Real-world horror stories: platform outages, blacklists, and how to dodge them
Timestamps
00:00 – Intro & why deliverability matters
02:33 – Tony’s background: SDR → deliverability consultant → Mission Inbox
05:35 – What actually happens after you hit “send”
06:56 – SPF, DKIM, DMARC explained with a “letter & seal” analogy
11:32 – Copy, links & images: how content triggers spam filters
15:54 – Why Apple & Yahoo open emails before users do
18:45 – Domain warm-up: what it is and best tools (WarmE.io, MailReach)
23:10 – Domain reputation factors: registrar, age, blacklists
30:38 – Affordable starter stack: Beehiiv + placement testing
35:30 – Tony’s 3-step deliverability checklist for creators
👉 Subscribe to LetterStack for more operator-level interviews on scaling, monetizing, and protecting your newsletter business at letterstack.co.
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Check out MissionInbox.com to explore Tony’s deliverability infrastructure platform.
Curious why top newsletter creators obsess over their subscriber data? In this episode of the LetterStack Podcast, we dive deep with Niklas Wenzel, founder of MegaHit and the Audience Doctor newsletter, to reveal how understanding who’s on your list can transform your newsletter into a revenue machine.
What you’ll learn:
Why knowing your subscribers is CRUCIAL from day one (not just when you’re “big”)
Scrappy (and free!) ways to collect and enrich your newsletter data—before you can afford fancy tools
How data leads directly to higher ad sales, better sponsorships, and even new product ideas
Real examples of creators doubling their ad rates and landing high-value sponsors
How to use first-party data, surveys, and smart outreach to create new revenue streams—starting with as few as 1,000 subscribers
When to invest in newsletter data enrichment tools like MegaHit
The right mindset for early-stage creators: why 1-on-1 conversations are still your growth superpower
Practical tips to avoid “AI for everything” traps and keep quality at the heart of your newsletter
About our guest:
Niklas Wenzel is the founder of MegaHit, the tool that top B2B newsletters use to unlock the true value of their audience. He’s helped names like CJ Gustafson (Mostly Metrics) grow and monetize through better subscriber insights—and now he’s building the Audience Doctor newsletter to share his strategies with you.
Timestamps:
00:00 – Intro to LetterStack Podcast
01:25 – Meet Niklas Wenzel (MegaHit, Audience Doctor)
05:16 – Why subscriber data matters for creators of ANY size
10:34 – Easy ways to collect & enrich your list (even without paid tools)
15:54 – Demo: What “enriched” data looks like (dummy data)
18:45 – The link between data, ad sales & sponsorship revenue
21:12 – How to reach out to your best-fit sponsors
24:32 – When to start monetizing: 1K, 5K, or 10K subscribers?
27:27 – Expanding to events, info products, and more
29:55 – How to (and when not to) use AI in newsletter growth
33:18 – Outro & where to find Audience Doctor
Subscribe to LetterStack for more episodes with the world’s best newsletter founders and operators.
Check out audiencedoctor.com for more actionable tips from Niklas!
Megahit - https://www.megahit.app
AudienceDoctor - https://www.audiencedoctor.com
#newslettergrowth #datastrategy #newslettermonetization #MegaHit #AudienceDoctor #LetterStackPodcast
Are you struggling to grow your newsletter beyond those first 1,000 subscribers? In this episode of LetterStack, we sit down with Nathan May how to use newsletter advertising to scale your newsletter. Nathan is the founder of Feed Media, the growth agency behind The Rundown, The Neuron, Bootstrap Giants to name a few!
Before we forget, subscribe for more such episodes at LetterStack.co
Nathan shares hard-earned lessons from consulting and scaling newsletters from zero to hundreds of thousands of engaged readers.
We break down:
When should you start running paid ads for your newsletter?
The mindset & math behind profitable paid subscriber acquisition
Budgeting: How much to invest before seeing real results
Choosing the right ad networks: Meta, Reddit, and beyond
The best ad formats for early-stage creators (including UGC & AI-powered content)
How to research copy that resonates with your audience (using Reddit & Quora!)
Case studies and real-world examples
Whether you’re still searching for audience-content fit or ready to test your first campaign, this episode is packed with actionable advice to help you scale smarter, not harder.
Don’t miss out! Subscribe for more expert interviews and growth tips for newsletter creators, and check out Feed Media to connect with Nathan May!
#newslettergrowth #newslettermarketing #paidmedia #feedmedia #ugc #aiads
00:00 Intro & Nathan’s background
05:26 When to start using paid media
10:30 Paid ads for early newsletter growth
14:41 Budgeting & burn rates
17:15 Winning ad formats & UGC
21:50 Researching copy that converts
24:30 AI UGC: Hot takes
27:11 Would Nathan do it differently today?
32:08 Closing advice & how to connect with Nathan
Sebastian Lindner and Chevy Cassar grew Web3Daily, a daily crypto and web3 newsletter, from 0 to 55k in the span of 28 months. Learn how the Web3Daily team grew their newsletter to eventually getting acquired by The Milk Road, one of the biggest newsletter brands in the web3 space.
Renganathan Padmanabhan talks to Sebastian to understand their newsletter journey, from their origins in building products to making the newsletter content a product in itself. He also unpacks what it takes to build a crypto newsletter with trust and integrity in an ecosystem which is riddled with scams and misinformation even in 2025.
Learn from Web3Daily and more such successful content creators at LetterStack.co, the one and only destination you need to head to create, grow, and build a successful newsletter business.
Learn more: letterstack.co