The decision to hire outside management for your growing business is never easy. Investors and owners are flooded with questions: Is now the right time? How should founders behave? And most of all, How will I cope?

That's the topic of an honest and thoughtful post by Jonathan Strauss, who founded After devoting blood, sweat, and tears to his startup for four years, investors told him there needed to be a change at the top, or else he'd be forced sell. It was a painful wake-up call that forced him to recalibrate his mindset:

"I put hiring a CEO in the same category as taking an acqui-hire or just closing up shop and moving on--things I would think about at 4am in the office on those darkest nights when I’d have a bout of sobriety about the insanity I’d turned my life into. And ultimately, things that represented the one unacceptable option motivating me to push even further beyond my limits I’d long surpassed: failure.

"In the early days, the only way for me to keep from failing was to tie my fate with the company’s. If failed, I failed. But as we switched from lean startup to growth company, I didn’t fully realize how making my ego a shareholder went from being necessary for survival to being a limitation on what we could achieve."

Giving up control would be painful, but his emotions were much more complex. 

"After three and a half years of fusing my self-worth with the success of the company in the crucible of startup survival, it was impossible to tear them apart without pain. But while my first reaction was disappointment and failure, it was almost immediately washed away by a wave of relief. I knew change was inevitable, but I had no idea how stressful and exhausting maintaining my internal reality distortion field had been until they gave me permission to turn it off."

Strauss details the pros and cons of selling his company versus hiring a new CEO. He doesn't shy away from admitting his mixed feelings--or the fears that kept him up at night. 

If you're facing a similar decision or just up for an unvarnished view on one of the toughest decisions a founder can make, the post is well worth a read.

Could you ever resign as CEO of your company?

Published on: May 22, 2013
The opinions expressed here by columnists are their own, not those of