The LetterStack Podcast

What if you could build a 6-figure newsletter business… in a completely untapped market?

In this episode of the LetterStack Podcast, we sit down with Fernando Caralt, founder of Espresso Matutino — one of the largest tech newsletters in Mexico with 145,000+ subscribers.

Fernando shares how he:

Started with paid ads from Day 1 (no organic-first playbook)
Built a Morning Brew-style newsletter for Mexico
Achieved break-even in just 3–4 months per subscriber
Expanded into podcasts, WhatsApp, and video
Runs a lean team powered by AI workflows
Navigates emerging markets vs US playbooks

If you're building a newsletter, media brand, or audience-first business — this episode is a masterclass in market adaptation + monetization.

🚀 What you’ll learn:
Why audience-first businesses beat product-first models
How to adapt US newsletter playbooks to new markets
The economics of paid acquisition for newsletters
Why WhatsApp might be the future of distribution
How to scale with a small, high-leverage team

⏱ Timestamps
00:00 Intro: Building Mexico’s Morning Brew
01:27 Why Fernando started Espresso Matutino
03:00 From engineering → entrepreneurship → newsletters
04:30 Audience-first vs product-first businesses
05:30 Adapting Morning Brew for Mexico
07:00 Why traditional media failed at newsletters
08:40 Content strategy: tone, brevity, and no politics
10:00 Email vs WhatsApp in Mexico
11:30 Launching WhatsApp newsletters (85% open rates)
13:00 Growth strategy: paid ads from Day 1
14:30 What failed: giveaway campaigns
15:00 Unit economics: CAC, CPM, break-even
17:00 Early growth: skipping organic entirely
18:30 Linear growth over 3 years
20:00 Hiring key team members (Steve Saldana)
21:00 Expanding into podcast & video
22:30 Content repurposing across formats
23:30 Scaling with a small team + AI workflows
25:00 Competition and defensibility
27:00 Mexico tech ecosystem insights
29:00 Why not expand to LatAm yet
30:30 Advice for new newsletter founders
32:00 Biggest mistakes and lessons

Subscribe to LetterStack for operator-level interviews on building, monetizing, and scaling newsletters.

Building one newsletter is hard.

Building multiple local newsletters that actually grow organically? That’s a different game.

In this episode of the LetterStack Podcast, we sit down with Danya Henninger, who scaled the Billy Penn newsletter from 8K to 40K subscribers without paid acquisition and now leads a multi-local newsletter ecosystem at Technically Media.

We break down:

How referrals drive real newsletter growth

Why local newsletters are still massively underbuilt

The exact content strategy that makes people forward newsletters

How to run multiple newsletters with a small team

Why weekly newsletters outperform daily in niche markets

The truth about organic growth in 2025

If you're building a newsletter, media brand, or local content business — this episode is packed with real operator insights.

⏱ Timestamps

00:00 Intro: Why local newsletters are exploding

01:00 Growing from 8K to 40K subscribers (no ads)

02:10 The #1 growth lever: referrals

03:30 Creating content people can’t find elsewhere

05:00 Experimenting with newsletter sections (A/B testing content)

07:00 Metrics that actually matter (beyond open rates)

08:30 Inside Technically’s multi-newsletter ecosystem

10:30 Do job boards really drive growth?

12:00 Audience overlap across newsletters

14:00 Newsletters as “community connective tissue”

16:00 Why niche local content wins

18:00 Running a newsroom: workflows, Slack, async ops

20:00 Why they moved from daily to weekly newsletters

22:00 The philosophy: newsletters as a product, not marketing

24:00 Mistakes, lessons, and funny newsletter fails

26:00 Launching a new newsletter in a new market

27:30 Discovery before launch: how to validate demand

29:00 Partnerships and distribution strategy

30:30 Monetization: underwriting vs ads

32:00 Final thoughts on building sustainable newsletter businesses

👉 Subscribe to LetterStack for operator-level interviews on building, monetizing, and scaling newsletters.

What if you could skip the start-up grind and acquire a newsletter business that’s already thriving?

In this episode of the LetterStack Podcast, Renga speaks with Alexis Grant, Founder of They Got Acquired — a media and education brand uncovering the hidden world of six, seven, and low eight-figure business sales.

Alexis has built and sold two content businesses, experienced both an acquihire and a full exit, and now helps founders learn how to sell their companies the right way.

You’ll learn:
✅ How Alexis built They Got Acquired into a trusted resource for founders and buyers
✅ How to find & segment serious buyers and sellers in your email list
✅ Why small acquisitions (under $10M) are the next big wave
✅ The secrets behind building a sustainable media business
✅ How Lexi revived her podcast and scaled content with minimal resources
✅ Why newsletter acquisitions are rising and what drives their valuations

Timestamps:
00:00 – Intro: Why acquiring is smarter than starting from scratch
02:10 – How They Got Acquired began and early subscriber growth
04:17 – Selling two businesses: from acquihire to full exit
06:15 – Understanding the small business M&A landscape
07:38 – How Lexi grew TGA’s audience via LinkedIn and pre-launch signups
09:08 – Segmenting subscribers by intent and collecting first-party data
11:10 – Identifying investors and buyers within the audience
12:13 – Convincing founders to share deal details transparently
13:53 – Educating founders on realistic valuations and multiples
16:36 – The sustainable content model behind They Got Acquired
19:03 – How Lexi repurposes stories into long-form reports
22:16 – Why volume doesn’t always win in media anymore
23:56 – Relaunching the They Got Acquired podcast and building trust via voice
25:36 – Lessons from How I Built This & focusing on relatable founders
27:19 – Are newsletters the next media assets being acquired?
29:05 – How audience value compares to ad revenue in media deals
31:18 – What makes email lists more valuable than social channels
33:42 – How to start and grow a newsletter for niche audiences
35:49 – Lexi’s upcoming course for founders who want to sell their businesses
37:13 – Outro: where to find Alexis Grant and They Got Acquired

Episode Overview

In this episode of the LetterStack Podcast, Renga speaks with TJ Larkin, who has built and partnered on more than 10 local newsletters with roughly 60,000 subscribers.

TJ explains how to launch a local newsletter, grow through Meta ads, choose content readers value, and monetize through sponsorships, directories, events, and related services.

Key Takeaways

Episode Chapters

About TJ Larkin

TJ Larkin is a local newsletter operator and entrepreneur behind a growing network of newsletters across the United States. He also runs LocalNewsletter.com, where he shares resources for building local newsletter businesses.

Final Takeaway

A successful local newsletter doesn't require a large newsroom. Start by sharing useful information about the community, build a broad audience, and gradually add sponsorships, services, directories, events, and other revenue streams.

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 job03:54 – First taste of remote work (2016) and the travel itch05:27 – Launching RemoteBase inside a Slack community (112 subs day 1)07:42 – The very slow road to 1 K & why that was OK09:09 – 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 split17:17 – How long-stay deal curation actually works (team, tools, “magic”)22:35 – Trip Reports: community-generated content + list micro-acquisition28:05 – 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.

🔔 Hit the bell so you never miss an episode!

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.appAudienceDoctor - 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!

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