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

Trendingnow

1

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year

2

The river that supplies 40 million Americans is down to 23% — and about to make a $25 million bet on one fish

3

Jamie Dimon said the American Dream was slipping away. JPMorgan just put $40 million on the table to fix it

1

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year

2

The river that supplies 40 million Americans is down to 23% — and about to make a $25 million bet on one fish

3

Jamie Dimon said the American Dream was slipping away. JPMorgan just put $40 million on the table to fix it
FinanceStartups & Venture

Why good startups shouldn’t obsess over price when selling

By
Fred Wilson
Fred Wilson
Down Arrow Button Icon
By
Fred Wilson
Fred Wilson
Down Arrow Button Icon
October 25, 2010, 2:55 PM ET

Most people assume that price is what matters most in a financial transaction. When you are raising money, you want to get the money at the highest price (least dilution). When you are selling, you want to get the highest price for your company. But that is not always the case.

Price matters, but my experience says that it often does not matter the most. In many of the venture deals we have done in the past few years, our transaction valuation was not the highest price offered to the entrepreneur. But the entrepreneur chose us as their partners anyway.

In the majority of the sale transactions that have happened in our portfolio, there were higher bidders for the company than the chosen acquirer.

You can get away with this behavior if you have a closely held business. If you have a public company, then you cannot. The Board has a fiduciary responsibility to get the best deal for the shareholders. And if you are a public company, that effectively means the highest price. That is one of many reasons I don’t like being on public boards and operating as a public company.

Let’s say you are one of two or three investors in a closely held startup company. Let’s say that between the investors and the founders, the group owns ~90% of the company. And let’s say that there are two purchasers. One is willing to pay $250 million in a clean transaction and the Board thinks they will be good owners of the business, will do everything possible to keep the team intact and the service vibrant. The other is willing to pay $300 million in a complex transaction, has a reputation for blowing up teams, and has been known to mess up the services they acquire. That would be a no-brainer. The board should take the lower offer in a heartbeat, assuming they really want to sell the business.

When you are doing an important financial transaction that brings a new influential owner into the company, price matters but is not the most important issue. The most important issue is the chemistry between the existing owners and the new investor/owner and the reputation of the new investor/owner. You want to use the market to surface the right valuation band and you should do the transaction in that band. But once you have done that, you should optimize for chemistry and fit. And let price fall somewhere in the “market band.”

If you cannot find an investor/owner who is a good fit in the “market band” then you should kill the process and not do a transaction unless you need to transaction to stay in business. If you are doing a transaction to stay in business, you have screwed up and put yourself in a bad position. And you should be prepared to be in a worse position soon. But that’s the subject of another post.

So price matters but don’t optimize for it. Not in a financing transaction. And not in a sale transaction. If you do, you will often regret it.

Fred Wilson has been a venture capitalist since 1996, and currently serves as managing partner of Union Square Ventures. He blogs regularly at AVC.

About the Author
By Fred Wilson
See full bioRight Arrow Button Icon

Latest in Finance

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 Finance

A Google engineer is facing federal charges after allegedly using his employer’s confidential data to pocket $1.2 million on Polymarket
Investingfraud
A Google engineer is facing federal charges after allegedly using his employer’s confidential data to pocket $1.2 million on Polymarket
By Marco Quiroz-GutierrezMay 28, 2026
1 hour ago
a woman looks at the produce she's buying
Economyaffordability
More Americans are going hungry now than during the pandemic, as people face a ‘remarkable’ rise in food insecurity, New York Fed says
By Jacqueline MunisMay 28, 2026
3 hours ago
ron
Personal FinanceFlorida
UBS says Ron DeSantis has a problem with his plan to help 92% of homeowners save on property taxes: His own state’s data
By Nick LichtenbergMay 28, 2026
4 hours ago
Jane Fraser defied the ‘glass cliff’ to engineer Citi’s long-awaited turnaround
NewslettersMPW Daily
Jane Fraser defied the ‘glass cliff’ to engineer Citi’s long-awaited turnaround
By Claire ZillmanMay 28, 2026
5 hours ago
Costco CEO Ron Vachris says tech is ‘elevating’ workers,’ not replacing them—as IBM and Delta bosses make the same bet on humans
Successthe future of work
Costco CEO Ron Vachris says tech is ‘elevating’ workers,’ not replacing them—as IBM and Delta bosses make the same bet on humans
By Preston ForeMay 28, 2026
5 hours ago
Boos, AI-washing, and ‘low-value human capital’: The psychological traps CEOs are falling into when they botch their AI messaging
C-Suitechief executive officer (CEO)
Boos, AI-washing, and ‘low-value human capital’: The psychological traps CEOs are falling into when they botch their AI messaging
By Claire ZillmanMay 28, 2026
5 hours ago

Most Popular

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year
Success
Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year
By Preston ForeMay 21, 2026
7 days ago
The river that supplies 40 million Americans is down to 23% — and about to make a $25 million bet on one fish
Environment
The river that supplies 40 million Americans is down to 23% — and about to make a $25 million bet on one fish
By Dorany Pineda, Brittany Peterson and The Associated PressMay 27, 2026
1 day ago
Jamie Dimon said the American Dream was slipping away. JPMorgan just put $40 million on the table to fix it
Banking
Jamie Dimon said the American Dream was slipping away. JPMorgan just put $40 million on the table to fix it
By Nick LichtenbergMay 27, 2026
1 day ago
Even if every California billionaire left tomorrow, it would take 25 years for the state to lose as much as it stands to gain from proposed wealth tax
Economy
Even if every California billionaire left tomorrow, it would take 25 years for the state to lose as much as it stands to gain from proposed wealth tax
By Tristan BoveMay 27, 2026
1 day ago
Techlash grows in education: 'My daughter went to middle school and was sent home with a screen addiction in her backpack'
North America
Techlash grows in education: 'My daughter went to middle school and was sent home with a screen addiction in her backpack'
By Jocelyn Gecker and The Associated PressMay 26, 2026
2 days ago
Current price of oil as of May 27, 2026
Personal Finance
Current price of oil as of May 27, 2026
By Joseph HostetlerMay 27, 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.