Operators Guild Co-Founder Casey Woo Featured on “Founders & Friends” Startup Podcast


Casey Woo, co-founder and managing member of the Operators Guild (OG), was recently interviewed on Founder & Friends, a startup podcast by Kruze Consulting. Kruze is an accounting, finance, tax, and HR partner for venture capital-backed startups, so they’re all about innovation and wisdom in the startup sphere.

Casey talked to COO Scott Orn, about why your environment matters, the importance of knowing who you are, and the story behind the Operators Guild. You can listen to the full episode here, but here are a few highlights from the interview:

Your Environment Matters

From day one, we’re taught to follow our skills and our passion. However, it’s equally important to make sure your work environment is conducive to happiness, growth, and success.

Take team sports, for example. Playing as part of a team teaches you how to work well with others, cooperate, compromise, and deal calmly and strategically with wins, setbacks and failures. 

“No one ever told me when I was growing up that you need to play team sports,” says Woo, who left a career as a hedge fund manager when he tired of the isolating work. “I never realized how important the (team sport) environment is. Now I know that I need to be with people.” 

If you love working alone, find a job that lets you do that. If you thrive in team sports, make sure you’re entering a field or a company where teamwork and camaraderie are a top priority.

Casey also remarked on the importance of “going where the best are” — it’s what led him to Harvard to study economics, New York to work in finance, and San Francisco to dive into tech. Not only will you learn from the best, but you’ll also be constantly inspired and motivated to be better. 

“If you want to go into the military, go to West Point and get your butt kicked,” said Woo (after all, he did it himself for two years). “If you want to do film, go to Hollywood. If you want to do tech, go to the Bay Area.”

The Who, What & Why of the Operators Guild

You know what the Operators Guild (OG) is all about, but do you know the how and why behind its inception? On this episode of the Founders & Friends podcast, Woo shared that he started OG because he was looking for “his people.” He wasn’t even sure that he knew who they were, but he definitely knew that he hadn’t found them. Relatively new to the Bay Area startup scene back in 2013, he was eager to connect with like-minded people who wanted to build things — operators, as he called them.

“I had an idea. I wanted to create a ‘moms group’ for operators — confidential, hard-hitting, helping, friendship, therapy, best practices,” says Woo.

Besides friendship and authenticity, there were only a few rules for the OG: no promotions/solicitation, show up, and what’s said here, stays here. New members were all thoroughly vetted through a nomination process.  

Casey is particularly proud of the fact that not a single OG member has ever been sold or marketed to — in fact, the OG doesn’t have a marketing person and isn’t a business. Their astronomical growth from eight members to more than 500 was entirely organic.

“It grew with word of mouth,” explains Casey. “What happens when you have a completely organic community is it has a whole different feel and ethos compared to a traditional professional community.”

Scott Orn, himself a member of the Operator’s Guild, had nothing but great things to say about the OG, namely its efficiency and value as a resource.

“I can just ask a question when I need to or I’ll answer people’s questions when I have a thought,” says Scott. “It’s like efficient networking … but I don’t have to sit at a cocktail party through someone’s terrible stories.

And so much more …

Again, this is just a snippet of the podcast interview — check out the full episode for more, including how the Covid pandemic affected operators themselves and the Operators Guild. You don’t want to miss this podcast.

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