When to Sell Your Startup: Kevin Ryan Shares Expert Exit Strategies
The Visionary Behind NYC’s Tech Boom
Kevin Ryan stands as one of New York City’s most influential tech figures. As founder and CEO of AlleyCorp, he’s shaped numerous startups while co-founding industry leaders like Business Insider, MongoDB (formerly 10gen), and DoubleClick - which Google acquired for $3.1 billion in 2007, revolutionizing digital advertising.
Decoding the Sell vs. Scale Dilemma
In a recent TechCrunch Disrupt masterclass for Startup Battlefield 200 founders, Ryan distilled decades of experience into actionable insights about one of entrepreneurship’s toughest decisions: when to sell your company.
Key Considerations for Acquisition Decisions
Ryan emphasizes there’s no perfect formula, but founders should evaluate:
- Growth Trajectory: “How much are we growing? What will this company look like in three years?”
- Market Position: “How are we doing relative to compe*****s?”
- Exit Options: “How many potential buyers exist?”
- Time Value: “If we’re worth \(100 today, we need \)200 in four years just to break even when considering risk and capital costs.”
The Hidden Risk of Holding Out
Ryan warns founders against underestimating market volatility:
“Markets can close at any time. Over 25 years, we’ve seen unexpected events like the Ukraine war or inflation spikes that suddenly freeze opportunities.”
He advises most founders should consider selling earlier rather than chasing unicorn status:
“You’ll hear about the $20B company that refused acquisition, but there are countless examples of founders who should have sold.”
The Psychology of Founder Exits
Ryan highlights a critical blind spot in founder psychology:
- Life-Changing vs. Life-Affirming Wealth: “\(30M is life-changing money. \)60M doesn’t make you much happier, but $30M makes a monumental difference from zero.”
- Opportunity Cost: Selling allows founders to pursue new ventures with financial security
Watch the Full Masterclass
For more insights on startup growth strategies and exit planning, view Ryan’s complete interview.
This content was originally featured as part of TechCrunch Disrupt’s Startup Battlefield 200 program, which provides elite founders with masterclasses from top investors and operators.
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