Jason Cohen - Building 2x unicorns, scaling, funding, WordPress stagnating and more

Today we’re joined by a titan of industry, Jason Cohen. He’s most well known for being the co-founder of WP Engine. You might also know Jason as A Smart Bear 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? Thanks for being a listener of the Make Lemonade show. Hosted by JR Farr & James McKinven— brought to you by https://lemonsqueezy.com. Follow us Lemon Squeezy -   / lmsqueezy   James -   / jmckinven   JR -   / jrfarr   Follow Jason Twitter -   / asmartbear   Blog - https://longform.asmartbear.com WP Engine - https://wpengine.com