Casey Woo is the co-Founder of Operators Guild, an invitation-only group that is built by operators, for operators.

Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I was born and raised in Los Angeles County: eight years in Alhambra and ten in West Covina. My parents were immigrants from China and Taiwan, so we had a classic sort of work-hard, education-focused family dynamic.

Dad was an old-school patriarch — always working, showed love through providing. Didn’t throw the ball with us. Vacations were pretty much nonexistent, and there was no such thing as “eating at the dinner table together.” My mom worked six days a week and made most of the income. She was incredibly soft-hearted and sweet. Unfortunately, my parents didn’t have the healthiest marriage, and as a result of all of this, my sister and I are incredibly independent — I personally am working on being far more “in touch with my feelings” as opposed to burying them — something that was conditioned into me to survive a “colder” upbringing where showing emotions was a sign of weakness.

Confidence, work ethic, and finding “family” through work and friends led to a “successful” academic career by traditional standards (West Point, Harvard, Wall Street, Silicon Valley), but there is certainly work to be done on the personal front in terms of conflict resolution, my marriage, etc.

What is something you wish you would’ve realized earlier in your life?

Over time, I’ve realized that success is all about how you make people feel — it’s not just about getting your homework done. EQ is just as important as IQ. Like pretty much anything in life, it all comes down to relationships and communication. At the end of the day, it’s people who will be giving you opportunities, teaching you new things, helping you achieve your dreams. So in that sense, the best thing you can do for your career is good at your job and a joy to be around.

Incompetent + Cold = Dead on arrival Incompetent + Warm (liked) = Pitied

Competent + Cold = Respected
Competent + Warm (liked) = Admired and Loved

Focus on people — they’re what will matter in the end. Relationships! In traditional Chinese culture, it’s all about action and tactics, and execution. We don’t hug a lot. My parents didn’t ask me how I felt a lot. I had to teach myself to actively listen (I’m still learning).

What are bad recommendations you hear in your profession or area of expertise?

Especially when you’re starting out, they tell you that networking is everything. Let me be clear: “Networking” doesn’t work. Building social, deep, and meaningful relationships works spectacularly well. People can sniff out disingenuous interactions immediately, and no relationship should be seen as purely transactional. A couple of years back, I sat down with a spreadsheet and wrote down everyone who had helped me in my career and how I’d met them. Almost all of the most important people in my professional life, I met as colleagues, friends of friends, mentors/mentees… friends! That’s what creates power and influence, not empty networking. I’d rather have ten friends than a hundred “contacts.”

Another one I’d love to note is that there’s a big difference between “business school” and the “school of business.” I’m not trying to knock business school, there’s value in it, but the value isn’t necessarily in learning business. There’s only one way to learn business, and that’s by putting yourself right in the thick of things.

Lastly, there’s a common misconception that it’s a badge of honor to take on more work, say “yes” to more, or know every single detail. That’s a quick path to burnout and failure — there’s much more value in setting boundaries, managing upward, outsourcing trust of details to a capable team, and focusing your energy only on the highest-value efforts.

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

My dad’s final words to me were “Next Christmas, son. Next year.” I’d begged him to quarantine so he could come for the holidays and meet his only granddaughter for the first time, but 50 days later, he died alone in the ICU of multiple organ failure due to COVID-19 — 2 weeks before his vaccine appointment.

Three years back, I’d already lost my mother, who succumbed to terminal ALS over the course of 22 brutal months. Time was a blessing and a curse — there was more time to say our farewells, but there was also more time to watch her suffer. Losing both parents in the span of a couple of years taught me a lot about death, and—by extension—a few things about life too.

1 – Make memories.
2 – Health is Wealth. Without health, you have nothing.
3 – Tomorrow is not guaranteed.
4 – Be grateful for all that you have (don’t waste time dwelling on what you don’t).
5 – Life is about the journey and the relationships made along the way, not the destination. Ask yourself — who will grieve the most when you pass? The deeper the grief, the sadder the loss, the more you meant to that person. Make a difference in someone’s life.

No one is ever “ready” to lose both their parents, but this experience made me more determined than ever to make every second count. You think business is life and death until you experience real life and death. Then you realize business is just business.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

My pure love of synergy and collaboration. I spend a lot of my mindshare understanding the skills, talents, and motivations of others — this has led me to the ultimate superpower, in my opinion: the ability to build incredible teams that can tackle any problem.

It’s not about a playbook or recipe, it’s about addressing every problem or situation with a unique set of ingredients and a custom recipe. So now… there are a few things “I” can’t do if the team is built correctly.

What is your morning routine?

The kids wake me and my wife up at 5:30 every morning. They jump into bed, and I love it. Coffee always. At 7 am, I head into work (yep, in-office, not WFH!). Pretty boring. Wish I could say I wake up at 4 am and get in a 90-minute workout, eat a healthy breakfast, et cetera. But no — kids, coffee, off to work!

What habit or behavior that you have pursued for a few years has most improved your life?

Helping others. Having accidentally built, I have had 1:1s with over 1,000 individual operators over 8 years. Before that, I was heavily involved in recruiting for my school, my employer, etc. I always try to give back, help, guide, or advise wherever I can. This has made my relationships and the people I surround myself with a very rich part of my life, and as a result, I’m far wiser and more fulfilled as a person. It brings me great joy to know I’m paying it forward and helping others.

What are your strategies for being productive and using your time most efficiently?

Outsource the things that other people can do better than you or the things that give you the time to focus on where you personally can drive the most value. A classic example is an amazing assistant (I’m so lucky to have one)… this is a game-changer in allowing me to stay focused on a select few major value drivers (whatever those may be, from major company initiatives to spending time with family).

It’s all about your team. I often say I’m the “hardest-working, laziest manager” you’ll ever meet. The quicker someone can supplement or even replace themselves with a team they can trust, the more value you can bring to your own life, your employer, etc.

You can’t be one of those “Rambo” leaders who take on everything on their own. They spend too much time “doing” as opposed to hiring, developing, and building out a team or selectively outsourcing in order to optimize their own time and maximize their specific value as a leader. It all goes back to where you spend your time — most of the time, it’s better to “pay” or have someone else do certain work to free yourself up to focus on “higher-value/pay-generating initiatives”. Otherwise, you will lose the war. Being “Atlas” works when you’re small… but as you grow and scale anything, Rambo will always lose the war. MacArthur is the one I have my money on. Let’s just say he’s doing 1/100,000th of the total “work.”

What book(s) have influenced your life the most? Why?

I wish I read more. Honestly, I’ve always been influenced and inspired more by experiences than media — I tend to learn by doing, so while I’m an avid reader, I’ve always done it more for pleasure than to improve my life or nurture anything inside myself.

Do you have any quotes you live by or think of often?

“Tomorrow is not guaranteed.”

My parents worked their asses off for decades, insistent that they’d travel and enjoy themselves when they retired. Both of them passed away before they could make that dream come true. Ever since then, I’ve been determined never to save all the good stuff for some abstract “tomorrow.” Don’t wait until you’re 75 to travel to Paris. Leave tomorrow!

“We don’t want to improve the blackberry, we want to build the iPhone.”
Otherwise known as: “I don’t want a faster horse, I want a car.”

As a leader, I like to focus on the goal in order to innovate. Don’t get tied to what is just because it’s the way we do it right now. Open-mindedness and risk-taking breed innovation and advancement.

“Business First, [function] second”

The purpose of any person is to make the business better. So always put business first — a good lawyer that puts business first, the legal second says “Okay, let’s stay out of jail. That’s the goal. How do we get there.” Don’t lead with your profession. “If you’re a hammer, everything’s a nail.” Be a toolkit! Hire toolkits. This is how I hire – I’m known for building amazing teams, identifying people’s strengths, and putting people with business mindsets together to create something powerful.

“Nine women can’t make a baby in one month.”

Know when to invest in things vs. when to rush them. I subscribe to the idea of “business physics,” or business as an organism. It’s got DNA, a heartbeat. I’ve been at companies with anywhere from 10 to 10,000 employees, and they all behave and develop in different ways. You can’t skip a kid from four years old to 15 years old, and in the same sense, you can’t rush things with companies either.

“Managers manage tasks. Leaders manage mindset.”

A business is just a group of people who decided to work together. In that sense, business is people! As you become a senior leader, it’s all about motivation, communication, and influence.
Instead of micromanaging, you have to elevate your thinking above granular tasks, above the day-to-day, and see that fourth dimension of what drives employees — work around that.