• 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

crew aboard artemis II
Innovationspace
‘It’s 13 minutes of things that have to go right’: Artemis II splashes down despite faulty heat shield
By Catherina GioinoApril 10, 2026
2 hours ago
Fed seeks details on U.S. banks’ exposure to private credit firms
BankingBanks
Fed seeks details on U.S. banks’ exposure to private credit firms
By Katanga Johnson, Dawn Lim, Silla Brush, Lydia Beyoud and BloombergApril 10, 2026
2 hours ago
The Navy confirmed an ‘abundant amount’ of Uncrustables when the Artemis II crew lands. Smucker’s just offered them a lifetime supply
PoliticsFood and drink
The Navy confirmed an ‘abundant amount’ of Uncrustables when the Artemis II crew lands. Smucker’s just offered them a lifetime supply
By Catherina GioinoApril 10, 2026
4 hours ago
Three people sit behind a desk and look at the phone screen of the person in the middle.
Future of WorkConsulting
Meet ‘trendslop,’ the new, AI-fueled scourge of workplace consultants everywhere
By Sasha RogelbergApril 10, 2026
4 hours ago
How to get out of debt: 9 proven strategies that actually work
Personal Financedebt relief
How to get out of debt: 9 proven strategies that actually work
By Joseph HostetlerApril 10, 2026
6 hours ago
Alpha Brain Review
HealthDietary Supplements
Alpha Brain Review (2026): Expert Reviewed Nootropic
By Emily PharesApril 10, 2026
6 hours ago

Most Popular

The U.S. government is spending $88 billion a month in interest on national debt—equal to spending on defense and education combined
Economy
The U.S. government is spending $88 billion a month in interest on national debt—equal to spending on defense and education combined
By Fortune EditorsApril 9, 2026
2 days ago
A Meta employee created a dashboard so coworkers can compete to be the company's No. 1 AI token user—and Zuckerberg doesn't even rank in the top 250
AI
A Meta employee created a dashboard so coworkers can compete to be the company's No. 1 AI token user—and Zuckerberg doesn't even rank in the top 250
By Fortune EditorsApril 9, 2026
2 days ago
Mark Cuban admits he made a mistake letting go of the Mavericks: 'I don't regret selling. I regret who I sold to'
Investing
Mark Cuban admits he made a mistake letting go of the Mavericks: 'I don't regret selling. I regret who I sold to'
By Fortune EditorsApril 9, 2026
1 day ago
Schools across America are quietly admitting that screens in classrooms made students worse off and are reversing years of tech-first policies
Innovation
Schools across America are quietly admitting that screens in classrooms made students worse off and are reversing years of tech-first policies
By Fortune EditorsApril 10, 2026
18 hours ago
Scottie Scheffler joined Tiger Woods and Rory McIlroy in golf's $100M club—and donated his entire Ryder Cup stipend to charity
Success
Scottie Scheffler joined Tiger Woods and Rory McIlroy in golf's $100M club—and donated his entire Ryder Cup stipend to charity
By Fortune EditorsApril 10, 2026
10 hours ago
'I hate working 5 days': Zoom CEO says traditional work schedules are becoming obsolete—and predicts a 3-day workweek by 2031
Success
'I hate working 5 days': Zoom CEO says traditional work schedules are becoming obsolete—and predicts a 3-day workweek by 2031
By Fortune EditorsApril 9, 2026
1 day 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.