🤑 How Nathan Barry Turned $50K Into a $30M/Year SaaS Empire

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Hey, Deal Lifters.

Sometimes the best investment is in yourself. And sometimes… you’ve gotta burn the boats 🚢🔥

That’s exactly what Nathan Barry did when he poured his entire life savings — $50,000 — into a startup that was barely crawling.

Today, that gamble is paying out $30M+ per year 💸

Here’s how he did it 👇

🎓 From Student to Six-Figure eBooks

Nathan wasn’t born into this. He studied marketing at Boise State, then kicked things off as a freelance web + software designer. 📱

He dipped into app dev, then started publishing eBooks about it. And hey — they worked. Real well. He was raking in $200K+ per year just from writing about what he knew.

But Nathan didn’t want a hit. He wanted a machine. Something scalable, something SaaS-y.

🚀 The $5K SaaS Challenge

So he set a personal challenge:
6 months. $5K budget. Build a SaaS that makes $5K/month.

The idea? He didn’t have one yet.

But frustration became inspiration 😤

He was using Mailchimp at the time — and he hated it. It wasn’t built for people like him… creators, bloggers, makers. It was made for marketers in suits.

So he built something better:
An email marketing tool for creators, by a creator.

And just like that, ConvertKit (now called Kit) was born 🎉

😬 The Struggle Was Real

The launch was... underwhelming.

6 months in? $2K MRR.
2 years in? $1,330 MRR.
Meanwhile? His eBooks were making $200K+ a year. Wild.

Most people would’ve folded right there 🫠

But Nathan got a wake-up call from a friend:

So he did the unthinkable — shut down the eBook biz that was printing cash, and went all-in on the struggling SaaS.

🧨 $50K All In. Sink or Scale.

He poured his entire $50K savings into ConvertKit.

Hired a developer. Brought on customer support. Time to scale.

And… nothing changed. For months.

By May 2015, the money was gone. The tank was empty.

But Nathan had one card left: direct sales.

He hit up creators personally. DMs, cold emails, anything. Showed them why ConvertKit was different. Why it was built for them.

That gritty, hands-on approach? 💯 It worked.

💸 From Flatlining to $100K MRR in One Year

Nathan zeroed in on his niche: professional creators. No fluff. Just tools that worked.

By 2016, ConvertKit exploded:

• MRR jumped from $2K → $100K

• Team scaled up

• Product evolved

• Community grew

Today, it’s known as Kit — the email-first OS for creators.

And in 2022? The company pulled in $33.4M in ARR 🚀

All from a $50K bet on a failing business.

🧠 Big Lessons from the Kit Come-Up

• Don’t chase mass appeal. Serve a niche deeply.

• Growth isn’t always sexy. Sometimes it’s cold DMs.

• Bet on yourself. But back that bet with relentless execution.

Nathan never hit his $5K/month challenge.

But he built a $30M/year beast instead.

Not bad for a “failure” 💀

🧠 TL;DR

• 📚 Nathan was making $200K/year from eBooks

• 💡 Got frustrated with Mailchimp → built ConvertKit

• 😰 After 2 years, MRR dropped to $1,330

• 🎲 Went all-in, put in $50K savings

• 💬 Doubled down on direct sales → MRR grew to $100K in 1 year

• 💰 ConvertKit (now Kit) did $33.4M ARR by 2022

⚔️ So, Founder... Are You Willing to Bet It All?

Building something great usually means getting uncomfortable.
Really uncomfortable.

So... what’s your all-in moment going to be? 👀

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