🚀 How 7 Founders Got Their First 1,000 Newsletter Subscribers (And How You Can Too)

Written By Rhone Findlay

Launching a newsletter today feels like launching a podcast in 2018 — everybody’s doing it. But unlike social media, email newsletters build something deeper: a direct connection.

They’re not just content. They’re a habit.

Think about it — your newsletter can become a weekly ritual, like a Tuesday night TV show. It can be the thing your readers look forward to, week after week.

But how do you start building that kind of relationship?

It all begins with your first 1,000 subscribers. And that number is more powerful than you think.

🧠 Why Your Newsletter Matters More Than Just "Followers"

Social media gives you awareness — people know you exist.

But newsletters build affinity — people love what you do.

Here's the difference:

  • Social = scrolling + forgetting

  • Email = opening + connecting

That inbox spot? It’s sacred. You’re not competing with memes. You’re speaking directly to someone.

💡 7 Real Examples: How Founders Got Their First 1,000 Subscribers

These aren’t theories. These are play-by-plays from actual creators who built newsletters worth thousands (even millions) of readers.

1. Morning Brew — Classroom Pitches

Founder: Alex Lieberman
How they did it:

  • Asked college professors and club presidents for 3 minutes to pitch in business classes

  • Handed out slips of paper to collect emails

  • Manually entered each one
    → This grassroots approach got them to 2,000 subscribers before graduation

✅ Takeaway: Find niche groups IRL and pitch in person. Small rooms build big lists.

2. Raisin Bread (MarketerHire) — Slice + Repurpose Content

Founder: Chris Toy
How they did it:

  • Turned blog traffic into email subs

  • Designed newsletters to be broken into social content

  • Used LinkedIn to post bites and drive opt-ins

  • Made content so shareable it spread on its own

✅ Takeaway: Build once, slice it everywhere. Social + word-of-mouth = compounding growth.

3. The Generalist — Start with Value, Add Hustle

Founder: Mario Gabriele
How they did it:

  • Added his newsletter to his email signature

  • Cold DMed PE/VC club leaders and got his newsletter shared in Slack groups

  • Targeted MBA students who’d care

✅ Takeaway: Solve a real pain point and people will do the sharing for you.

4. Payload — Cold DMs Done Right

Founder: Ari Lewis
How they did it:

  • Used LinkedIn search to find people in the space industry

  • Sent them personal messages about the newsletter

  • Shared space updates on Twitter to build curiosity

  • Cross-promoted with his own audience of 11K followers

✅ Takeaway: Targeted cold outreach still works — if it’s relevant and respectful.

5. The Green Paper — Interview & Share Strategy

Founder: Matthew O’Brien
How they did it:

  • Launched with LinkedIn audience already engaged

  • Hit a plateau at 250 subs

  • Interviewed cannabis industry leaders and included them in the newsletter

  • Encouraged them to share it

✅ Takeaway: Make others look good → they’ll share it → you grow.

6. Bootstrappers (MicroAcquire) — Pick a Fight + Go Viral

Founder: Andrew Gazdecki
How they did it:

  • Called out TechCrunch for ignoring bootstrapped startups

  • Created content for the underdog

  • Let startup founders submit stories directly

  • Turned stories into Twitter threads that exploded

✅ Takeaway: Great content plus controversy creates a flywheel of shares.

7. The Bear Cave — All-Out Outreach

Founder: Edwin Dorsey
How they did it:

  • Tweeted at launch and got first 200 subs

  • Turned newsletter into viral Twitter threads

  • Cold emailed investing clubs

  • Personally DMed 2,000 followers asking them to join

  • Said yes to every podcast invite

✅ Takeaway: Hustle + smart distribution builds a loyal list fast.

🔁 10 Repeatable Tactics to Grow Your Newsletter

Want to follow in their footsteps? Here are the highest-impact, lowest-fluff growth strategies:

  1. Create viral loops – Make your newsletter worth sharing. Add social CTAs.

  2. Do content swaps – Partner with other newsletters for shoutouts.

  3. Use email signatures – Subtle but effective. Add a subscribe link to every email you send.

  4. DM real people – Thoughtful cold outreach can 10x your early subs.

  5. Interview experts – Feature them in your newsletter. They’ll share it.

  6. Add lead magnets – Checklists, cheat sheets, or tools in exchange for email.

  7. Make your newsletter “clip-friendly” – Chop it into posts for LinkedIn, Twitter, etc.

  8. Build inside communities – Indie Hackers, Facebook Groups, Discords, etc.

  9. Accept every podcast invite – You never know which one unlocks new readers.

  10. Start a referral program – Reward sharing with access, perks, or tools.

📈 Final Thought: Your First 1,000 Sets the Stage

Don’t aim for a million right away. The first 1,000 subscribers teach you:

  • What content resonates

  • What drives shares

  • Who your audience really is

Build that core community. Treat them like VIPs. Give more than you ask.

And when the growth hits — you'll be ready.

Rhone Findlay
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