👾Leveling Up 👾

WPEngine does over $400M ARR today.

I asked Founder Jason Cohen when he thought the timing was right to raise money. His previous company, A Smart Bear, was completely bootstrapped before he sold it in 2007 (it sold again for $450M in 2017 and then $2B in 2020).

Initially, he built WPEngine to only serve bloggers. But the reality was WordPress was growing like a weed. The total addressable market (TAM) was much larger than just the blogger world (it was 10% of the internet at the time).

They raised an initial round of $1M, which isn't much by today's standards. Along the way, they always raised at 'fair valuations' where they weren't getting diluted too much and the investors were getting their fair share. Because of that, there wasn't unreasonable pressure placed on them.

Even when they were raised hundreds of millions of dollars, their ARR was already in the 9 figures.

Jason's take is there are good sides and bad sides to both bootstrapping and raising.

You just have to choose what makes the most sense to you.

Eric Siu :)

Our Skool Community

The Agency Owner's Association (AOA) is our paid community on Skool that is for expert agency owners looking to scale.

It’s $199/month, and you’ll receive:

• Access to both mine and Neil Patel’s network

• Access to all of our best training courses

• Special deals on software

• Strategies and frameworks

• Resources and templates to build the right systems, processes, and structure

Interested?

Apply here (link).

Links You Might Like

Here are some of the best links I’ve found since our last email. 

🏢 Business

“You’re allowed to make less money for more joy” (link)

✉️ Email

Apple’s latest email campaign reversed-engineered (link)

💰 Finance

How marketing agencies structure their finances (link)

🤖 AI 

10 AI websites that will save you hours (link)

📈 SEO

The biggest winners and losers since Google’s August update (link)

How I Can Help You

If you enjoy this newsletter and would like to collaborate with me, there are a few options available:

1. You can apply to work with my marketing agency (link)

2. You can join my Skool community for agency owners (link)

Interested in working at Single Grain? We have some new open roles:

• Business Development Representative (link)

• Paid Media Manager (link)

• SEO Manager (link)