The cheerful stewardess on my red-eye to Argentina was delivering her pre-flight speech. Her soothing voice washed over me as I sat in a window seat, reading a business plan for a technology start-up on my laptop.

“There are 10 emergency exits on this Boeing 777 aircraft: 4 in the…

“Wait a second,” said my girlfriend. “Aren’t you supposed to be showing people how to make money?”

I’d just shared this week’s essay topic with her. Now she was looking at me like I had three heads.

She had a point. It’s true that we generally try to show you…

Last Thursday morning, as I was browsing headlines on The New York Times, I saw an article entitled, “Which Start-Up Could Be the Next Big Thing?”

That’s a serious newspaper and an exciting topic. Coffee in my left hand, mouse in my right, I clicked on through.

After the author…

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Tags: Company valuation Equity value Exit strategy Liquidity Price Startup equity Valuing a-startup

Few things are certain in this world; few things are actually guaranteed.

Ben Franklin famously put death and taxes on his list. But on a sunny summer day in August, I’m not so interested in addressing those dreary topics.

Guaranteed money, on the other hand — now there’s something that…

“Jumptap just sold for $200 million!”

The breaking news about Jumptap, a mobile advertising company, came to me by email.  It made me smile. It’s not every day that an early-stage company sells for 9 figures.

And with a $200 million sale, the investors must have made a fortune!

I…

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Tags: 500 startups Accelerators Angel Crowdfunding Demo days Early stage Ideas Investing Qwiki Techcrunch disrupt Techstars Ycombinator

The cylinder of the .38 mm handgun spins around and around. It makes the familiar “whirrrrrrr” sound – but this time the sound isn’t coming from a movie or TV show.

The hammer of the revolver clicks into place. I involuntarily shudder. It’s my turn.

Hands shaking, I slowly lift…

Remember a game called “Follow the Leader” from when you were a kid?

One kid, the leader, would stand up at the head of a line. He’d touch his nose, zig and zag, click his heels. Everyone else would have to copy what he did.  

If…

The champagne was flowing.

Music filled the air.

Beautiful people were dancing, lounging, and having the time of their lives…

That’s the image I had in my head when I wrote a check for what turned out to be the worst investment of my life.

Dim Lights, Big City

I…