Founder Stories

The 4 Big Ways That “Founder” and “CEO” Are Different Jobs

Lessons, learned mostly the hard way, from building and running a company

Joel Wish
Published in
5 min readNov 4, 2019
A silhouette of Steve Jobs’ profile against the Apple logo during the 2004 Apple Worldwide Developers Conference keynote.
Photo: Justin Sullivan/Getty

InIn startups, “founder CEOs” have a kind of mythic power — visionaries who not only give birth to new ideas, but bring them to life across every stage as the organization grows. Zuckerberg. Jobs. Benioff. A few names that embody that myth.

But the truth is, founder and CEO are different roles. Very few people are cut out to make the transition from the former to the latter. In fact, only around a quarter of founders manage to hold on to the title of CEO by the time the IPO comes around, and the majority, nearly 80%, are pushed out.

Yet a lot of founders, myself included, believe they can make the transition, despite the odds. The truth is, most founders underestimate the abrupt shift in approach, thinking and sometimes even philosophy, required to successfully maneuver from one to the next. I’d like to share some of the lessons I’ve learned in transitioning from founder to CEO of Simple Health with the hope that these will help more of you be part of the surviving 20%.

But before we dig in, let’s confirm the differences between a founder and a CEO.

Lesson #1: Everyone loves the founder, not so much the CEO

In the beginning, before you get to product/market fit, the founder’s role feels both incredibly overwhelming and incredibly exciting at the same time. The possibilities often seem limitless. You have a small team, everyone fully believes in the vision, and you see meaningful progress every day.

But as the company grows and the founder transitions to CEO, a lot of that changes. Your job is to define the focus of the organization: What to pursue, and what not to pursue. Inevitably, some of those decisions will bring you into conflict with the visions and ideas of other people within your company.



Joel Wish

3x founder, advisor, angel investor. Most recent @getSimpleHealth @frontlinefoods @parsley_health @everlywell @mindbloom. Long $BTC $DOT