Don't Let Past Success Blind Your Current Vision

When Amy Katz and I co-launched After Nines Inc. in Sept. 2014, a lot of friends and family checked in and made a statement like this: "You've succeeded before. It will be even easier this time around." In some ways, life is easier these days. But in other ways, I believe past success can cloud your judgment as you plot a path forward. You've got to fight that reality. Here's why.

Amy and I have known each other since around 1998. We've worked together at big IT media companies (example: Ziff Davis). We've worked together for the founders of another startup (Microcast Communications). And by 2008, we went off and launched our own business -- Nine Lives Media Inc. With a lot of hard work and a ton of luck, we grew that business rapidly and sold it to Penton in 2011. We remained with the business until May 2014 before exiting, unplugging, relaxing -- and then re-emerging with After Nines Inc. in September 2014.

Same Vision, Different Year?

I think a lot of industry pundits assumed we would go back to doing what we had done before: Launch a few blogs then wrap media services around the blogs -- while hitting the road every week to evangelize the business.

But here's the reality: We leveraged that model way back in 2008, just when the shift from traditional IT media sites to community- and personality-driven blogs was accelerating. It was perfect timing. And we were happy to be road warriors in undiscovered territories.

Fast forward to 2014 and that startup playbook is a bit dated. Plus, we wanted to avoid the "repeat" syndrome.

Lessons From the Mac

Think of it this way: Some of my favorite artists avoided temptation to simply "repeat" what they had done before.

After Fleetwood Mac's massively successful Rumours album arrived in 1977, the music studio essentially wanted the band to deliver Rumours II. Instead, self-proclaimed band leader Lindsey Buckingham took the group in a new direction. The result was the wildly ambitious, experimental Tusk album, which initially generated mixed reviews in 1979. But looking back, Buckingham considers it his favorite Fleetwood Mac studio album.

Why's that? Probably because Buckingham and the band insisted on complete creative freedom -- even when corporate powers were pressuring them to stick with a past formula for success.

Instead of trying to repeat Rumours' success note for note, Buckingham, Mick Fleetwood, John McVie, Christine McVie and Stevie Nicks followed their hearts and experimented. The results weren't always perfect. But then again, tunes like Sara and the title track Tusk became classics.

Lessons for I.T. Entrepreneurs

We've seen similar examples across the IT market, where folks like Gary Read (Nimsoft to Boundary), Jeff Leventhal (OnForce to Work Market), Marketing Hacker Tristan Barnum (Digium to Tellient) and Rajat Bhargava (seven startups to JumpCloud) continually reinvent themselves. Sure, those entrepreneurs leverage lots of past learnings. But they aren't blinded by past success, nor do they stick to yesterday's script. Instead, they keep experimenting in front of our our eyes.

Here at After Nines Inc., we aspire to do the same. 

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