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?
Absolutely !! they will do it again… guys like these, you can take everything away from them…leave them in a beat up broken down bug on the side of the road with just the clothes on their back…and they will just do it** again
ironically, they are both in my poker group and have been friends of mine for over 10 years!
best jason
Jason is definitely a smart guy and a hard worker, but I'm going to say he got lucky with Weblogs Inc. If he were the real deal he'd just go about his business building multi-milliion dollar companies instead of pimpin his ideas and biting off people's heads at conferences.
Affiliate confession: for the record, my first business Silicon Alley Reporter reached 11.6M in revenue in its fourth year…. so I got much luckier on that one.
Yep Jason, you did earn a pretty penny with that one as well.
I just went to check out F'd Company and it gave me this message (edited for language):
F*ckedcompany is… temporarily f*cked
Yes, it is unfortunate… has been that way for some time now. It was a good site, I liked it.
They were extremely lucky, but it takes a good bit of work to put yourself in the position to get lucky!
You forgot to mention how old they are
I love to know the ages of great entrepreneurs 
-Mike
I'm 37 and I think Dachis is older than me and Phil is a little younger.
I don’t know abut the others, but Kaplan was lucky.
If by luck they mean busting your ass, networking with the right people, seeing an opportunity that no one else sees, being smart enough to gauge where the market and the industry is going, hiring the right people, planning every quarter for growth or consolidation, sacrificing, risking, and getting up every time you get knocked down, then yeah they’re lucky.
If by luck they mean walking in the door and getting handed millions of dollars, then I want to know what color the sky is in that world, because it’s not this one.