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

Trendingnow

1

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI

2

Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 

3

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises

1

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI

2

Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 

3

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
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
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
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
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in

CDC to escalate Ebola response after WHO declares emergency
HealthHealth
CDC to escalate Ebola response after WHO declares emergency
By Jessica Nix and BloombergMay 17, 2026
1 hour ago
Markets are jittery as the global oil crisis bleeds into a global debt selloff, while Trump weighs new military options on Iran
EnergyOil
Markets are jittery as the global oil crisis bleeds into a global debt selloff, while Trump weighs new military options on Iran
By Jason MaMay 17, 2026
2 hours ago
Four crew members ejected safely after two Navy jets collide and crash during air show in Idaho
North AmericaMilitary
Four crew members ejected safely after two Navy jets collide and crash during air show in Idaho
By The Associated PressMay 17, 2026
3 hours ago
Gundlach says it’s ‘just not possible’ for the Fed to cut rates
EconomyFederal Reserve
Gundlach says it’s ‘just not possible’ for the Fed to cut rates
By Jordan Fitzgerald, Sam Kim and BloombergMay 17, 2026
4 hours ago
Supply shocks weren’t random. They were strategic—and should be seen as ‘supply coercion’ instead, former Fed official says 
Economysupply chains
Supply shocks weren’t random. They were strategic—and should be seen as ‘supply coercion’ instead, former Fed official says 
By Jason MaMay 17, 2026
4 hours ago
U.S. says China to buy $17 billion of agricultural goods annually
EconomyChina
U.S. says China to buy $17 billion of agricultural goods annually
By Yash Roy and BloombergMay 17, 2026
6 hours ago

Most Popular

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloMay 16, 2026
1 day ago
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
Politics
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
By Jason MaMay 16, 2026
1 day ago
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
5 days ago
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
Innovation
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
By Jason MaMay 16, 2026
1 day ago
Oil markets could be a month away from the moment of truth. Brace for a 'non-linear' price spike and panic buying, analysts warn
Energy
Oil markets could be a month away from the moment of truth. Brace for a 'non-linear' price spike and panic buying, analysts warn
By Jason MaMay 16, 2026
1 day ago
'No one was coming to save me': How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn't fix
Success
'No one was coming to save me': How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn't fix
By Sydney LakeMay 17, 2026
13 hours 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.