Calacanis, Kaplan and Dachis… Just Lucky or Good?

Will lightning strike twice for these entrepreneurs… or did they just get lucky? Fortune Small Business magazine did a spotlight on the few entrepreneurs that ended up starting a hot internet company, then ended selling for millions. Now the question is, are these players one hit wonders, or can they strike gold again. Let’s put the spotlight on Jason Calacanis, Philip Kaplan and Jeff Dachis.

Jason Calacanis
(publisher of Silicon Alley & owner of Weblogs Inc.)
Calanis’ claim to fame was selling WebLogs Inc. to AOL for a reported $25 million dollars. Since then he has focused his time on creating his own human powered search engine, called Mahalo.com. In addition to spending time on Twitter and posting new Mahalo links (tweets) and videos to his 20,000+ followers, you will also find Jason stirring up controversy with his outspoken opinions towards the affiliate marketing and SEO industry marketers.
FSB Lesson Learned: “Sell when someone offers you 10 to 15 times revenue”

Philip Kaplan
(Founder of F*ckedCompany.com)
Kaplan’s new focus is on his advertising network AdBrite.com, but what made Kaplan an internet superstar was his F*ckedCompany.com. Featured as the dot com dead pool, F*ckedCompany.com was a resource and gossip-like site viewed by millions, as employees and insiders at companies would send Kaplan the insider info, whether it be layoffs, earnings figures or ridiculous emails sent through the company to their employees.
FSB Lesson Learned: “Transparency with your employees” - it makes them less likely to air dirty laundry on gossip sites.

Jeff Dachis
(CEO of RazorFish)
After Microsoft bought aQuantive, the parent company of Razorfish, Dachis went on to be the founder of Bond Art & Science, a web design and consultancy firm. The biggest hit (or stike) for Jeff and RazorFish, was when their stock public, to trade at over $100 per share, then plummeting to less than $1 per share.
FSB Lesson Learned: “Humility”

In addition to the players above, you can read about more industry movers in a new book called “Once You’re Lucky, Twice You’re Good“. Did players like Calacanis and Dachis, just get lucky or did they really earn their millions? It’s not rare for huge companies like AOL & Microsoft to put up millions/billions of dollars to acquire new companies… but do these guys have what it takes to strike lightning twice… or where they just lucky?

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