10 lessons from 10 years of building a SaaS company


Hi Reader,

2023 marks a big milestone for me: I've now spent a full decade building ConvertKit!

10 years ago, I started my first SaaS company. In that time, I’ve grown it to $33.4 million in annual recurring revenue.

Here are 10 lessons I’ve learned over the last decade:

1. It takes longer than you think

Two years in, I was only at $2k/month in revenue, not profitable, and smart friends were saying I should shut down the business.

A year later, we were doing $100k/mo.

I was so close to moving on to other projects, but I’m grateful I didn’t.

2. Go all-in sooner

I ran ConvertKit part-time while also blogging and selling digital products.

While that can work to test an idea, I wish I’d gone all-in as soon as I had initial traction rather than waiting 2 years and rebuilding momentum after a slump.

When a project isn’t working, you can admit that it’s a failure, shut it down, and move on to something else…

…or you can give it the time, money and attention it deserves to build a real business.

My framework for deciding:

3. Do direct sales

The key to restarting growth after I went all in was direct sales. As a content marketer, I was only interested in scalable growth channels. I was so wrong!

Do things that don’t scale, because that enables the channels that do scale.

​ConvertKit got stuck at $1,500 MRR until I learned this trick »​
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4. Choose a niche

I couldn’t have done direct sales without a target audience.

Part of the reason ConvertKit was failing is I was targeting everyone who needed marketing.

Focusing on professional bloggers early was pivotal. Later we expanded & now serve creators of all kinds.

5. Focus on product quality

Talk to your customers, find the most painful parts of the product, and fix them. Use your product yourself every day.

Scaling without focusing on product quality increases churn.

A polished product was key to get us to 99.8% revenue retention.

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6. Build a culture of execution

Overly focusing on bootstrapping attracted a group of people who wanted work/life balance over everything. Growth stalled.

I later pivoted to:

  • Hire pros with experience scaling software companies
  • Paid more with equity
  • Pushed for results

7. Don't underestimate deliverability and fraud

We’ve hired a great compliance team and built machine learning models to find and prevent issues, but had I known up front how much time we'd spend fighting spammers and fraudsters, I might not have started ConvertKit.
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8. Meet customers and partners in person

Zoom meetings are easy, but there's no match for connecting with people face to face.

You will stand out if you fly to a city and meet with your key partners and customers in person. Those relationships are invaluable.
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9. Use workshops to create urgency

For someone to make a purchase, they need a reason to buy now (as opposed to later).

Webinars and workshops are a great way to give prospects a deadline. Since events happen in real time, the end of the event creates a natural deadline.

In 2016, we created a flywheel of partner workshops with affiliates to scale from $100,000 to $500,000 in MRR that year. Sometimes teaching as many as 20 workshops per month.

Offering a sign up bonus at the end of the workshop drove thousands of customers.
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10. Move from cost center to revenue center

Most creators pay ConvertKit and earn their ROI through other activities. But we're working hard to make sure ConvertKit is paying you.

Through Commerce and our sponsor network, we are now paying creators $1+ million per month.
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What I'm most proud of is the creators we serve

In the same day, I helped Arnold Schwarzenegger, Tim Ferriss, and Ryan Holiday with their ConvertKit accounts.

My wife had some music on. The artist used ConvertKit.

It hit me: Nearly all of my favorite creators use ConvertKit!


Did you find these takeaways useful? Consider forwarding this email to a friend, or feel free to retweet the Twitter thread.

Thanks for reading, and Happy New Year!

—Nathan

P.S.

If you're a creator who's looking to land sponsorships and brand deals in 2023, Justin Moore, founder of Creator Wizard, is a great resource for this.

Learn how to pitch and price your partnerships so you don't leave thousands on the table.

​Sign up for the free weekly report »​

Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

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