• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
Entrepreneurship

Clif Bar’s Former CEO Opens Up About the Emotional Toll of Entrepreneurship

By
Jeremy Quittner
Jeremy Quittner
Down Arrow Button Icon
By
Jeremy Quittner
Jeremy Quittner
Down Arrow Button Icon
November 28, 2016, 8:00 AM ET

These days, it’s becoming almost trendy for entrepreneurs to openly discuss their depression and other emotional afflictions. They’re getting hip to what some researchers have known for a while: the same obsessive drive that makes a good entrepreneur also has a dark side.

Yet Sheryl O’Loughlin, the co-founder of Plum Organics and the former chief executive of Clif Bar, says this dark side needs to be addressed even more openly.

In fact, it’s the subject of her new book, Killing It! An Entrepreneur’s Guide to Keeping Your Head Without Losing Your Heart. In it, O’Loughlin, who has taught entrepreneurship at Stanford University, tells the tale of her own struggle with personal demons. She hopes those tales and her advice about running a business will start a conversation with other entrepreneurs, and entrepreneurs-to-be.

O’Loughlin, who is now CEO of herbal drink company REBBL, sat down with Fortune to discuss her book.

The following interview has been edited for grammar and clarity. The book will be released on Dec. 6.

What was your motivation for writing the book?

O’Loughlin: I had these students who would come in with dollar signs in their eyes, and they were so excited to change the world with their companies. And that was incredible, but as an entrepreneur, there is the great light side, but also a dark side. When people hear about entrepreneurship in the media, it is all about this person who was a huge success [and] who made all this money. Students get the impression that is what it is all about. There is also drug abuse, divorce, depression, and suicide, and those are things that people don’t talk very much about. Entrepreneurs tend to talk about it after they’ve already been through it, and they will say, “I had a really hard ride.” I wanted people to understand this as they go into it, so it is not so scary.

 

Why do you suppose entrepreneurs have such tough time with depression?

O’Loughlin: As an entrepreneur, you are selling a vision in something that does not exist. You need investors to invest in it and employees to work for you when you can’t pay anything. Part of our job is being optimistic and positive and sunny. But it’s not only depression. We have a higher incidence of attention-deficit hyperactivity disorder and a higher propensity for drug abuse. The psychiatrist Michael Freeman says it’s a spectrum. On the one side, entrepreneurs are obsessive and dedicated and persistent, and that is the light side. That’s what makes them good entrepreneurs. But if I am also this person who is obsessive, it can result in depression.

So is this a business book or a self-help book?

O’Loughlin: There are a lot of gaps this book is filling. Most business books are: Here’s how you start a company. That’s in Killing It, too, and this is part of the story. The other part of the story is life and the human experience of life. That is also connected to the experience of the startup. I go into romance, marriage, children, [and] friendship. I talk about physical and emotional well-being. All of these are important.

Related: This Company Delivers Honey Bees Straight to Your Home

What is your story, about your demons?

O’Loughlin: At the same time I co-founded Plum Organics, my husband started a company that was the antithesis of [fast food]. It was an indoor place to bring your kids, to have creative activities, and healthy food. The day it opened — it had been freezing cold — it was beautiful and sunny, and it stayed that way for a couple of months. Two months into this, he came home and was a white as ghost saying we had run through all the cash. We had to close the doors, with a $20,000 a month lease still on us.

I had also started Plum. And I had a really, really rough investor who would tell me I was the greatest CEO one second, and the next, he would berate me. I would be in a board meeting telephonically, and he would text me that everything I was doing was wrong. I had the stress of starting my company, the stress of this investor, and the stress of my husband who then could not get out of bed for two months because of his depression. I was holding it all together, and over time, I developed an eating disorder.

What have you learned from all of this?

O’Loughlin: I have learned how to make the right choices. I know that every moment does not mean the company will fall apart, and I don’t tie [the company’s success or failure] to my self-worth anymore. That is what creates these demons. I also know how to make the right choice on investors. You need to go through entrepreneurship with a partner who supports you through the ups and down. We can be a tribe of entrepreneurs, who are connected and talk to each other in ways we are not talking now. Think of entrepreneurship in terms of your life as a whole.

About the Author
By Jeremy Quittner
See full bioRight Arrow Button Icon

Latest in

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in

cooper
EnergyIran
UK accuses Iran of Hormuz ‘hijack,’ holding global economy hostage
By Jill Lawless, Nick Lichtenberg and The Associated PressApril 2, 2026
4 minutes ago
musk
EconomyIPOs
Elon Musk, world’s first trillionaire: one implication of the massive SpaceX IPO
By Bernard Condon, Ken Sweet and The Associated PressApril 2, 2026
8 minutes ago
Current price of Ethereum for April 2, 2026
Personal FinanceEthereum
Current price of Ethereum for April 2, 2026
By Joseph HostetlerApril 2, 2026
9 minutes ago
mcdonalds
RetailMcDonald's
McDonald’s joins the value menu simpler is better trend with 10 items at less than $3 each
By Dee-Ann Durbin and The Associated PressApril 2, 2026
11 minutes ago
Major 4-day workweek study suggests that when we work 5 days we spend one doing basically nothing
SuccessProductivity
Major 4-day workweek study suggests that when we work 5 days we spend one doing basically nothing
By Orianna Rosa RoyleApril 2, 2026
11 minutes ago
Current price of Bitcoin for April 2, 2026
Personal FinanceCryptocurrency
Current price of Bitcoin for April 2, 2026
By Joseph HostetlerApril 2, 2026
38 minutes ago

Most Popular

Gen Z fled San Francisco for Texas and Florida. Now they’re turning ‘welcomer cities’ into the next big tech towns
Real Estate
Gen Z fled San Francisco for Texas and Florida. Now they’re turning ‘welcomer cities’ into the next big tech towns
By Fortune EditorsApril 2, 2026
8 hours ago
Current price of gold as of April 1, 2026
Personal Finance
Current price of gold as of April 1, 2026
By Fortune EditorsApril 1, 2026
1 day ago
Two-thirds of parents say their adult Gen Z kids still rely on them financially  for support—even though it's putting them under strain
Success
Two-thirds of parents say their adult Gen Z kids still rely on them financially  for support—even though it's putting them under strain
By Fortune EditorsMarch 31, 2026
2 days ago
Current price of oil as of April 1, 2026
Personal Finance
Current price of oil as of April 1, 2026
By Fortune EditorsApril 1, 2026
1 day ago
Jerome Powell says the $39 trillion national debt is ‘not unsustainable,’ but warns the trajectory ‘will not end well’
Economy
Jerome Powell says the $39 trillion national debt is ‘not unsustainable,’ but warns the trajectory ‘will not end well’
By Fortune EditorsMarch 30, 2026
3 days ago
2 years after Musk challenged Zuckerberg to a cage match, they were texting about DOGE and a joint OpenAI bid, court records reveal
Law
2 years after Musk challenged Zuckerberg to a cage match, they were texting about DOGE and a joint OpenAI bid, court records reveal
By Fortune EditorsMarch 31, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.