• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
Startups & Venture

Illiquid Till Exit: Is the golden era of secondary share sales over for startups?

By
Erin Griffith
Erin Griffith
Down Arrow Button Icon
By
Erin Griffith
Erin Griffith
Down Arrow Button Icon
July 21, 2014, 12:30 PM ET
Careers
contact Armin harrisKyle Bean for Fortune

Any startup that’s raised capital with a valuation in the hundreds of millions is on the radar of hedge funds, secondary market players and various other boiler rooms for private company stocks. (Call them “spawn of Advanced Equities.”) And it’s creating a thorny issue for startup CEOs.

With startups waiting longer than ever to go public (and thus, leaving less hyper-growth on the table for public market investors), public market investors are under pressure to find high-growth opportunities in the private markets. When Dropbox raises $350 million, or Uber raises $1.2 billion, it’s basically like an IPO, except it’s not open to all retail investors.

So these funds are getting aggressive in their quest for private company shares. One way they’re doing that is by blasting out solicitation emails to startup employees, offering to buy their shares at astronomical valuations. The offers might not be serious — it’s hard to know — but its enough for employees to get dollar signs in their eyes. It’s enough to prompt them to ask management about cashing out.

This poses a problem: The company ’s board has a fiduciary duty to take any offers seriously, but at a ridiculous valuation, how can it? Further, if the company does say yes, it now has a random fund in its cap table, at a valuation much higher than the rest of the shares. There’s little precedent for deciding what class of shares the new buyer gets, and at a higher valuation, how many they get. “It’s a CFO’s nightmare,” one VC said. Not to mention, the insider trading laws for public companies apply to private companies as well, making compliance expensive and cumbersome as the shareholder base expands.

Those issues are why, increasingly, companies are following the lead of startups like Dropbox and Uber and saying no to employee share sales. Based on an informal survey of investors, that’s been the trend since Facebook, which turned into the Wild Wild West of secondary shares before its IPO. At the time, SecondMarket and its peers were hailed as an innovative, entrepreneur and employee-friendly way to do business. It creates a real market with real values for private company stock, with less volatility, declared the New York Times. Secondary markets “act as a stent, relieving the congestion in the arteries of capital formation,” proponents told Businessweek in 2011. But the accounting nightmares it created left investors and CEOs who witnessed it turned off by the idea.

The pendulum has since swung in the other direction, the investors Fortune surveyed said. (They requested anonymity to avoid the appearing unfriendly to entrepreneurs.) Venture firms now make strong recommendations to their portfolio company CEOs as early as a Series A fundraising that employee stock sales remain forbidden until a liquidation event. Companies have always had the right to refuse a potential share sale — they’re simply refusing a lot more now. If employees want to cash out, they have to wait for an honest-to-goodness exit.

There’s one little issue with this shift: Saying no to employee requests for share sales becomes a poaching issue. Top executives at companies like Uber and Dropbox are among the most in-demand talent in Silicon Valley, and that’s not lost on Google, Facebook and Apple. The big public companies can offer an executive, say, a $5 million stock package with full liquidity. Uber can offer the promise of an IPO… someday.

The move to more conservative secondary sale policies hasn’t stopped funds and advisory firms focused on buying shares from startup employees. (Take Battery East Group, a firm founded by former BlackRock exec Michael Sobel, and former Maveron advisor Barrett Cohn, for example.) But the new twist on secondaries seems to be loans over share sales. Earlier this month, 137 Ventures raised $137 million to lend money to private company shareholders and employees who are rich on paper with illiquid shares. Another firm called VSL Partners, founded by GSV Capital partner Dave Crowder will offer the same thing.)

So, if startups are becoming stricter about employee share sales, where will the funds hungry for private company shares invest their capital? Turns out, it’s all about who you know. CEOs are much more likely to approve a secondary sale if it’s to a firm they know and trust, and many of the firms springing up to facilitate sales start out with a relationship. Growth-hungry hedge funds and boiler rooms take note — befriend the next Drew Houston or Travis Kalanick, and you might have yourself a deal.

About the Author
By Erin Griffith
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

Trump vows to reduce U.S. troops in Germany ‘a lot further’ than 5,000 as defense official says armed services were blindsided by move
EuropeMilitary
Trump vows to reduce U.S. troops in Germany ‘a lot further’ than 5,000 as defense official says armed services were blindsided by move
By Kirsten Grieshaber, Emma Burrows, Aamer Madhani and The Associated PressMay 2, 2026
3 hours ago
 Trump says he is reviewing a new Iranian proposal to end the war but ‘can’t imagine that it would be acceptable’
PoliticsIran
 Trump says he is reviewing a new Iranian proposal to end the war but ‘can’t imagine that it would be acceptable’
By Aamer Madhani, Sarah El Deeb, Cara Anna and The Associated PressMay 2, 2026
3 hours ago
Can the ‘blue economy’ deliver on its promise? Investors are starting see the ocean as an asset worth protecting
CommentaryConservation
Can the ‘blue economy’ deliver on its promise? Investors are starting see the ocean as an asset worth protecting
By Natalie Sum Yue ChungMay 2, 2026
4 hours ago
Iran juggles oil cuts and storage strain to resist U.S. blockade
EnergyIran
Iran juggles oil cuts and storage strain to resist U.S. blockade
By Anthony Di Paola, Ben Bartenstein, Patrick Sykes, Weilun Soon, Charles Gorrivan and BloombergMay 2, 2026
6 hours ago
Disney’s new CEO is exploring a ‘super app’ for theme park tickets, movies and more
Big TechMedia
Disney’s new CEO is exploring a ‘super app’ for theme park tickets, movies and more
By Thomas Buckley, Lucas Shaw and BloombergMay 2, 2026
6 hours ago
Apple raises Mac Mini’s starting price to $799 after AI frenzy drains supply
AIChips
Apple raises Mac Mini’s starting price to $799 after AI frenzy drains supply
By Chris Welch, Mark Gurman and BloombergMay 2, 2026
6 hours ago

Most Popular

Scott Bessent on financial literacy: 'it drives me crazy' to see young men in blue-collar construction jobs playing the lottery
Personal Finance
Scott Bessent on financial literacy: 'it drives me crazy' to see young men in blue-collar construction jobs playing the lottery
By Fatima Hussein and The Associated PressMay 1, 2026
2 days ago
Gen Z is rebelling against the economy with ‘disillusionomics,’ tackling near 6-figure debt by turning life into a giant list of income streams
Economy
Gen Z is rebelling against the economy with ‘disillusionomics,’ tackling near 6-figure debt by turning life into a giant list of income streams
By Jacqueline MunisMay 2, 2026
13 hours ago
Current price of oil as of May 1, 2026
Personal Finance
Current price of oil as of May 1, 2026
By Joseph HostetlerMay 1, 2026
2 days ago
A Chick-fil-A worker got fired and then showed up behind the register to allegedly refund himself over $80,000 in mac and cheese
Law
A Chick-fil-A worker got fired and then showed up behind the register to allegedly refund himself over $80,000 in mac and cheese
By Catherina GioinoMay 1, 2026
1 day ago
Stop donating to Harvard and the Ivy League. There's a better option that MacKenzie Scott already figured out
Commentary
Stop donating to Harvard and the Ivy League. There's a better option that MacKenzie Scott already figured out
By Ed Smith-LewisMay 2, 2026
19 hours ago
The American household just took an 81% margin cut. Wall Street hasn’t priced it in
Commentary
The American household just took an 81% margin cut. Wall Street hasn’t priced it in
By Katica RoyMay 2, 2026
16 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.