Facing Some Difficult Truths: From burn-out to $100M in ARR with WP Engine


Jason Cohen – CTO & Co-Founder / WP Engine



Metrics are important, but so is making the tough, gut-wrenching decision to part ways with a key employee. Product strategy is important, but a fixation on the competition is counter-productive. A successful exit can set you up financially, but how do you avoid the fate of (statistically) the majority of founders who become sad and unmoored after an exit, rather than ecstatic over their newfound wealth and entering the next chapter of life?

We can manage products and even people, but managing our own minds can be hardest of all. Ironic, since biologically it ought to be the thing we can control most of all. Bad management of the mind results in poor strategic decisions, focussing on the wrong things, and unnecessary negative emotions and stress over what someone said on the Internet, what a competitor did, what an employee did, or how the company evolves away from its roots. Startups are difficult enough and risky enough as it is, even without this added burden.

Through personal stories and commiseration with your fellow entrepreneurs, you’ll face the truth, take solace in seeing you’re not alone, and overcome these challenges using a specific set of tools.



21 our of 22 Founders were depressed after selling in a survey recently conducted

Make emotionally tough decisions

Holding on too long:

  • There’s the good reason
  • and then there’s the real reasons

Stuck in your craw – The notionally tough choice is usually the right choice.


Be an editor, not a writer

Results vs action orientated when hiring

  • Need to hire results oriented people!
  • Event manager example – talks about what they did vs the outcome of the event

Hire impactful people – the founder is not the power of the business, they steer the ship but they are not the engine room


The below image was included in Jason’s slide deck.. it is such a good representation of today’s society that don’t want to work for change but expect it without doing anything about it. Be the one to put your hand up and make a difference.


The below slide shows Jason’s first business, Smartbear, exit. He sold it to Insight in 2007. Insight sold it to Frisco in 2017. He was very happy with his decision to sell at the time and doesn’t regret it. How would you feel when you see your company grow and sell for $450m+.