Today we’re joined by Jason Cohen. He’s most well known for being the co-founder of WP Engine. You might also know Jason as @asmartbear on Twitter and from his popular blog with the same name, started almost 2 decades ago. Jason is a 2 times unicorn founder so has some incredible startup wisdom at all stages of growth.

This is a wide ranging conversation where we talk about Jason’s day to day life at WP Engine, how he deals with big business problems, if his writing is done on WP Engine, how he would scale to $1m if he was starting from scratch and we also get his thoughts on Lemon Squeezy’s growth going into 2024.

Timestamps

• 00:00 Intro
• 02:51 Why there is so little content on the scale up stage
• 07:00 Is WordPress growth stagnant?
• 09:47 What does Jason's day look like?
• 13:02 Doing the boring things
• 16:08 Does Jason miss the early days?
• 20:03 Dealing with people challenges at scale
• 27:56 How does Jason fit writing into his schedule
• 30:41 Andertoons
• 32:33 Going from 0-$1 million
• 39:22 On side projects
• 40:13 Thoughts on Lemon Squeezy fundraising
• 47:42 Advice on Lemon Squeezy growth in 2024
• 55:16 The future of WP Engine
• 01:00:32 Should Jason invest in Lemon Squeezy?

As always thanks for being a listener of the Make Lemonade show. Hosted by @jrfarr & @jmckinven— brought to you by LemonSqueezy.com. 

If you're looking to sell digital products online, be sure to check out Lemon Squeezy or follow us on Twitter @lmsqueezy.