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

Trendingnow

1

Even as Elon Musk calls philanthropy ‘very hard,’ everyday Americans gave a record $617 billion—despite feeling the squeeze over the cost of living

2

Egg companies made $1.22 billion in profit off a $6 carton — now they’re buying their way out of a price-fixing case with 53 million donated eggs

3

Meet the Zillennials: The luckiest micro-generation in the workforce, born between 1993 and 1998

1

Even as Elon Musk calls philanthropy ‘very hard,’ everyday Americans gave a record $617 billion—despite feeling the squeeze over the cost of living

2

Egg companies made $1.22 billion in profit off a $6 carton — now they’re buying their way out of a price-fixing case with 53 million donated eggs

3

Meet the Zillennials: The luckiest micro-generation in the workforce, born between 1993 and 1998
Commentary

The Only Time It’s Okay To Pass Up a Great Opportunity

By
Cheryl Black
Cheryl Black
Down Arrow Button Icon
By
Cheryl Black
Cheryl Black
Down Arrow Button Icon
February 20, 2016, 11:30 AM ET
175591101
Teenage student is thinking in front of the blackboardPhotograph via Getty Images
Add Fortune on Google for similar content.

The Leadership Insider network is an online community where the most thoughtful and influential people in business contribute answers to timely questions about careers and leadership. Today’s answer to the question: What did you learn from your biggest failure? is written by Cheryl Black, CEO of YOU Technology.

After a dozen years in corporate America, I cofounded my first startup. I wrote the original business plan and financial model, and one of my partners recruited someone he knew for the CEO role. We moved to a house in San Francisco to operate the company. While we all paid rent, I was the only one putting in hard cash for business expenses prior to funding. I worked night and day on partnerships, engineering, professional services, and managing our clients. I am embarrassed to say that I had no idea who owned what percentage of the company — other than what I owned. I hadn’t seen the cap table. I went to board meetings — but only the open sessions. I wanted to build the company so badly, that I didn’t insist on any terms in exchange for the funding I was providing. I trusted my partners to do the right thing.

We eventually obtained funding from a top-notch VC and our staff grew to 55 people — all working in our house — before moving to a ‘real’ office and adding another 20 or so employees. We had vastly different styles and our CEO called the shots on how we spent our money. He hired a firm and spent a lot of money on rebranding and hired an expensive VP of Marketing. Although we had built an entire platform, revolutionized the telecom agency model, and had several paying clients, the market was tough in 2000 and 2001, so we eventually had to shut our doors, and sell the assets. Needless to say, I lost everything I invested. Stepping away from the whole experience I realized there were several lessons that I learned the hard way. The most important ones were:

See also: What to Do When You Make a Huge Mistake at Work

Chemistry matters
The only way to partner effectively is with the people who share the same ideals, goals, and styles. Don’t ever settle for working with someone you don’t know or don’t agree with on the basics. Just because they have experience, past success, look good on paper and can attract funding, does not mean you should trust them. If they hide things from you, run.

Check your gut
Alarm bells were going off for me from day one, but I had so much passion invested in building the company — forging partnerships and building a model — that I instantly agreed to work with someone I didn’t know because I thought he could bring funding and get us off the ground. I loved the team I worked with, how hard we all worked, and how much we accomplished. I was so involved in the journey that I turned a blind eye to what my gut was screaming.

Don’t compromise
When it comes to foundational elements of a business — don’t compromise. Don’t be afraid to walk away or pass on what seems like a great opportunity if it doesn’t feel right — even if you are deeply emotionally invested. I certainly learned this from my expensive experience. Though it cost quite a bit more than my MBA, the lessons were more deeply felt and life altering. I have come to appreciate that I had the opportunity to make this mistake without losing more than some cash. Needless to say, it has absolutely shaped the way I approach business
to this day.

About the Author
By Cheryl Black
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in Commentary

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 Commentary

k
CommentaryBox office
How Hollywood’s youngest filmmakers are exposing Gen Z’s real problem with AI
By Reid LitmanJuly 5, 2026
9 hours ago
k
Commentary250 Years of Innovation
Media leadership unity in defying Trump’s assault on free speech: standing tall against historic comparisons
By Jeffrey Sonnenfeld, Jeff Bewkes, Kay Koplovitz, Tom Glocer and Marvin KalbJuly 4, 2026
1 day ago
ds
CommentarySoftware
I argued with the father of open source for 2 years. Now the AI fight is the same — only bigger
By David SiegelJuly 3, 2026
2 days ago
ashok
Commentary250 Years of Innovation
The greatest startup in history: What we can learn from America’s founders at today’s AI frontier
By Ashok N. SrivastavaJuly 3, 2026
2 days ago
2
Commentary250 Years of Innovation
America’s secret weapon isn’t just innovation — It’s the freedom to fail
By Keith KrachJuly 3, 2026
2 days ago
rn
CommentaryCryptocurrency
Former Iran director at NSC: Crypto legislation is a ticket to sanctions evasion
By Richard NephewJuly 2, 2026
3 days ago

Most Popular

Even as Elon Musk calls philanthropy ‘very hard,’ everyday Americans gave a record $617 billion—despite feeling the squeeze over the cost of living
Success
Even as Elon Musk calls philanthropy ‘very hard,’ everyday Americans gave a record $617 billion—despite feeling the squeeze over the cost of living
By Preston ForeJuly 4, 2026
2 days ago
Egg companies made $1.22 billion in profit off a $6 carton — now they’re buying their way out of a price-fixing case with 53 million donated eggs
Law
Egg companies made $1.22 billion in profit off a $6 carton — now they’re buying their way out of a price-fixing case with 53 million donated eggs
By Wyatte Grantham-Philips and The Associated PressJuly 2, 2026
3 days ago
Meet the Zillennials: The luckiest micro-generation in the workforce, born between 1993 and 1998
AI
Meet the Zillennials: The luckiest micro-generation in the workforce, born between 1993 and 1998
By Nick LichtenbergJuly 3, 2026
3 days ago
$25 billion CEO says one-hour interviews are a waste of time—he puts candidates through six hours of tests and wants them to order wine at lunch
Success
$25 billion CEO says one-hour interviews are a waste of time—he puts candidates through six hours of tests and wants them to order wine at lunch
By Orianna Rosa RoyleJuly 3, 2026
3 days ago
Economists have found an answer to slowing cognitive decline: Avoid retiring early, study finds
Economy
Economists have found an answer to slowing cognitive decline: Avoid retiring early, study finds
By Sasha RogelbergJuly 2, 2026
3 days ago
Russia's fuel crisis is so bad that a mom and her baby waited in line for 18 hours to get gas — 'Are we in the Soviet Union?'
Energy
Russia's fuel crisis is so bad that a mom and her baby waited in line for 18 hours to get gas — 'Are we in the Soviet Union?'
By Jason MaJuly 4, 2026
22 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.