Real Entrepreneurs Get Back Up

I asked Mark Jeffrey for an interview because I knew he’d be open with me about the periods in entrepreneurship when things fall apart and you feel like there’s no way out. Mark helped launch 4 startups, including SuperSig, which was a disaster and Mahalo, a rising star.

Mark Jeffrey

Mark Jeffrey


Mark Jeffrey is an award-winning serial entrepreneur of innovative technology companies backed by Tier One investors.

A few lessons from this program

Network by evangelizing

In the mid-90’s, Mark was just another guy working at Time Warner, but he loved the project he was working on, an avatar-based chat community called “The Palace.” He evangelized it to anyone who would listen, that’s how he made connections with people in the industry.

He knew that a behemoth like Time Warner was no place to grow an innovative startup. So he tapped his connections and got Intel and Softbank to buy pieces of The Palace and let him grow it. Within 3 years of launching, The Palace was sold and Mark was a superstar entrepreneur.

“There’s no joy in my life”

His followup venture was SuperSig, a service that let users personalize their emails’ signatures. Raising money was easy because he was a superstar and the dotcom market was hot. But then the dotcom bubble burst and he lost his investors’ and his own money.

He remembers telling his partner at the time, “There is no joy in my life right now except when I’m asleep.”

SuperSig closed down, but he fought till the end. When it was over, Homer Luther, Mark’s investor, sent him a note congratulating him for fighting long after everyone else gave up. If you’re ever in Mark’s office, ask him to show you the note. When you read it, you’ll feel the pride of putting up a strong fight.

The bust made us better entrepreneurs

I’ve interviewed a few entrepreneurs here on Mixergy who told me that the dotcom bust of 2000 made them better entrepreneurs. In Mark’s case, it taught him to cut costs to the bone.

His next startup was ZeroDegrees, an early MySpace. He launched it with ZERO outside investment. He ran it lean and sold it to InterActiveCorp. It gave him a big victory and financial freedom.

Today he’s working on his latest startup as the CTO of Mahalo. If you listen to the interview, you’ll notice that he’s as proud of the way it’s capitalized as he is of how cool a company it is. I feel like our generation of web startups was improved by the bubble’s burst the way the World War II generation was fortified by their reaction to the Great Depression.

“Being broken in half allowed me to write”

Aside from being a better entrepreneur, going through the dotcom bust helped Mark start writing books.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.