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

Trendingnow

1

26 Meta employees accuse Mark Zuckerberg of using AI to target 8,000 layoffs against workers on medical, parental or family leave

2

MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly

3

After donating $48 billion to the Gates Foundation, Warren Buffett is quietly ending one of the biggest philanthropic relationships in history

1

26 Meta employees accuse Mark Zuckerberg of using AI to target 8,000 layoffs against workers on medical, parental or family leave

2

MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly

3

After donating $48 billion to the Gates Foundation, Warren Buffett is quietly ending one of the biggest philanthropic relationships in history
Commentary

9 Questions That Will Determine Your Entrepreneurial Success

By
Cliff Johnson
Cliff Johnson
and
Bethany Cianciolo
Bethany Cianciolo
Down Arrow Button Icon
By
Cliff Johnson
Cliff Johnson
and
Bethany Cianciolo
Bethany Cianciolo
Down Arrow Button Icon
May 25, 2017, 11:53 AM ET
1
GirlbossKaren Ballard/Netflix
Add Fortune on Google for similar content.

The Entrepreneur Insiders network is an online community where the most thoughtful and influential people in America’s startup scene contribute answers to timely questions about entrepreneurship and careers. Today’s answer to the question, “What should budding entrepreneurs know about building a business?” is written by Cliff Johnson, co-founder and chief development officer of Vacasa.

There’s no blueprint for how to launch a business, and in entrepreneurship, things rarely go according to plan. Fortunate founders blunder their way to success, and then years down the road, step back to reflect on the wild ride. One strategy I found to be helpful when we were starting Vacasa back in 2009 was developing a state of startup self-awareness. Making time to ask the right questions in the early stages will help you shape direction and priorities over the inevitably rocky road to come.

Here are some tips to get your wheels turning:

Determine your level of influence
You’ve spent time building an operations plan, defining a target market, and thinking about how much working capital you’ll need. Now take a minute to think about what you’re willing to give up to make it all happen. Some investors are silent; others want total control. You could become an industry leader or you could hire one. Knowing the level of influence you want to retain will help drive the decisions you make.

Do you want your business to be a reflection of you, your investors, or the people you hire to run it?

Identify your best self
Once you know what you’re best at, build a career around it. For example, I’m at my best when impacting something tangible. At its heart, the vacation rental management business is about customer service and cleaning homes. I love that. I wouldn’t be a good GM of a SAAS company, for example, unless there was a meaningful connection to something tangible.

What are you doing when you hit your golden gait?

Embrace unexpected strengths
Founders have to be nimble. From customer service to board meetings, you’ll do it all, and along the way, you’re going to discover strengths you never realized you had. As an attorney, I was surprised with my business development ability. I found cold calling to be fun because closing a property is about building relationships—something I enjoy.

How will you identify and nurture surprise strengths?

See also: What Every Entrepreneur Should Be More Prepared for When It Comes to Money

Identify your weaknesses
Recognize your weaknesses early on. I’m overly optimistic, which can be a double-edged sword: Pushing too hard tends to throw off the balance of quality, efficiency, and growth.

What’s your biggest weakness?

Champion your values
How you’ll treat customers, employees, and the communities in which you operate is core to your business model. You want to get to a place where values drive decisions. If you can’t think of any values (don’t worry, you have them), create a list of words describing how you’d like future customers to feel about your service. Do it again for your employees and community.

What five words define your business?

Get uncomfortable
Being a founder is an exercise in awkwardness and poverty. Prepare by throwing yourself into uncomfortable situations. Try a new physical activity and find your limits. Push yourself to try something you’ve never done before. Do some volunteering so you appreciate how hard life can be for those who do not have as much as you do, and try to give back to the causes as often as you can through volunteering and eventually donating when your business can afford to.

What makes you uncomfortable?

Solve a difficult problem
If your business isn’t hard, it’s probably not going to be around for long because it will be easy for competitors to replicate your model. At Vacasa, we manage cleaning and maintenance operations for homeowners around the world. It’s logistically challenging. It’s also what sets us apart and what we’re most passionate about.

What’s difficult about your business?

 

Register for the future
It’s important to start thinking early on about where you want to register your business. There are pros and cons to having a simple or tax-advantageous structure. You might anticipate doing all your business online. Then again, you might someday want brick and mortars across the country. Make the right decision for where you want to be in the future.

How will your idea grow?

Prioritize tech
Regardless of industry, every business is a tech business. If you can’t digitize your dream, make sure to hire someone who can as early as possible.

What are your technical challenges?

Launching a business isn’t easy, but you’ll stand a better chance of succeeding if you embrace what you don’t know. Talk to founders. Ask questions. Reflect. The more startup self-awareness you develop, the better equipped you’ll be for the unexpected challenges ahead.

About the Authors
By Cliff Johnson
See full bioRight Arrow Button Icon
By Bethany Cianciolo
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

sb
Commentarynational debt
The national debt is over 100% of GDP and most of Congress is ignoring wishes to rein it in. It’s time to amend the Constitution
By Steve H. Hanke and David M. WalkerJuly 15, 2026
12 hours ago
Is your AI really working? Why productivity isn’t the same as progress
Future of WorkBrainstorm Tech
Is your AI really working? Why productivity isn’t the same as progress
By Jamie GarverickJuly 15, 2026
14 hours ago
r
CommentaryFDA
Trust in the FDA is collapsing. It’s time to get really transparent about our food and our drugs
By Jeffrey Sonnenfeld, Megan Ranney, Sten Vermund, Patricia Greenstein and Steven TianJuly 14, 2026
1 day ago
mm
Commentaryregulation
Exclusive: Delaware proposes testing the AIC, a new legal entity for agents in a regulatory sandbox
By John Nay and Charuni Patibanda-SanchezJuly 14, 2026
1 day ago
jobs
CommentaryLabor
Black women’s unemployment rate fell. That’s not the good news you think it is
By Katica RoyJuly 14, 2026
2 days ago
b
CommentaryWorld Cup
Columbia Business School professors: What the Balogun red card can teach us about AI and judgment
By Oded Netzer, Christopher Frank and Paul MagnoneJuly 13, 2026
2 days ago

Most Popular

26 Meta employees accuse Mark Zuckerberg of using AI to target 8,000 layoffs against workers on medical, parental or family leave
Law
26 Meta employees accuse Mark Zuckerberg of using AI to target 8,000 layoffs against workers on medical, parental or family leave
By Barbara Ortutay, Alexandra Olson and The Associated PressJuly 15, 2026
14 hours ago
MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly
Newsletters
MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly
By Sydney LakeJuly 14, 2026
1 day ago
After donating $48 billion to the Gates Foundation, Warren Buffett is quietly ending one of the biggest philanthropic relationships in history
North America
After donating $48 billion to the Gates Foundation, Warren Buffett is quietly ending one of the biggest philanthropic relationships in history
By Marco Quiroz-GutierrezJuly 14, 2026
1 day ago
Jamie Dimon understands why people are anti-rich: 'We have, in fact, left the lower-income folks behind' and 'that's kind of annoying'
Economy
Jamie Dimon understands why people are anti-rich: 'We have, in fact, left the lower-income folks behind' and 'that's kind of annoying'
By Eleanor PringleJuly 15, 2026
16 hours ago
He sold his last company to Palantir. Now he's betting $32 million that robots can fix construction's labor crisis
Innovation
He sold his last company to Palantir. Now he's betting $32 million that robots can fix construction's labor crisis
By Lily Mae LazarusJuly 15, 2026
15 hours ago
FedEx CEO says we are in the middle of the biggest supply chain shift he’s seen in 35 years: ‘We are the referendum’
C-Suite
FedEx CEO says we are in the middle of the biggest supply chain shift he’s seen in 35 years: ‘We are the referendum’
By Fortune EditorsJuly 15, 2026
12 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.