The rise of the Portland serial entrepreneur

Anyone who has chatted with me about “hurdles the Portland startup scene has yet to overcome” has heard me describe one of those problems as the dearth of serial founders in town. You know, the folks who founded companies or were early employees, built something, exited, and then started something else. Lather. Rinse. Repeat. Well, a few recent news stories have me thinking that might be starting to happen with a little more consistency, finally.

And it’s that recycling of knowledge and connections and capital and other stuff that will help build momentum and sustainability for the Portland startup ecosystem. And that’s always a good thing.

Here are just a few examples:

Dave Hersh

If you caught the recent news about Portland’s Cloudability acquiring RipFog, you may have also noticed a secondary theme there. You see, RipFog was cofounded by Dave Hersh. Dave was the original CEO of Jive, a company that settled in Portland early in its life and went on to be one of the first major exists of this generation of startups.

While Dave doesn’t call Portland home these days. He’s still a tangible influence here. And the bulk of the RipFog team? Yep. All Portland based.

Not to mention that Dave has a good working relationship with a16z.

Dave Shanley

One of the cofounders of CrowdCompass, which was acquired by CVent a while back, Dave is onto his next pursuit now. It’s called Notion. And this time, Dave is not only a founder, he’s the CEO.

Raven Zachary

Raven has been a long time contributor to the Portland startup and open source community, including helping to stand up BarCamp Portland, way back when. But he’s perhaps best known as the cofounder of Small Society, one of the first creative agencies to take on iPhone app development. After landing customers like a little coffeeshop and a small car rental company, the company was acquired by Walmart Labs.

Now Raven is chasing his next platform ahead of the crowd. And the learnings from Small Society will no doubt influence this pursuit.

Greg Rau

One of the more prolific serial founders just announced his latest pursuit.

After experience in a number of startups, Greg set out as the cofounder of StepChange, a Web app developer that happened upon the potential of Facebook apps before selling to Dachis Group.

That experience—and those cofounders—then parlayed that into Upstart Labs, an early stage startup accelerator that funded and augmented startup teams. Upstart found success in its model, but eventually wound down as it threw resources behind Chirpify, one its alumni.

Now Greg is onto his next project, Rivetry. And it’s tapping into his previous experience building solutions for an emerging industry.

And those are just few obvious stories. I’m sure there are more. And I hope—sincerely—that there are many more to come.

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