We were lucky to catch up with Kai Sato recently and have shared our conversation below.

Kai, appreciate you joining us today. Let’s kick things off with your mission – what is it and what’s the story behind why it’s your mission?

The vision for Caddyshack to Corner Office (CCO) is to build an enduring golf media franchise. Not just rags to riches stories but to provide the voice for the self-made golfer, those who didn’t grow up at country clubs – THE community for the feel good stories in golf. This includes all races, all genders, all religions, and all geographies.

Why? By inspiring kids to caddy, it not only gets them to play the game but gives them the tools, training, and most importantly the relationships to alter the trajectory of their lives. Furthermore, while golf is the most philanthropic sport by a wide margin, it’s still viewed as elitist, despite such endearing stories that permeate the game but have yet to be properly brought to life.

I know this because I’m living proof of it. I put myself through college working as a caddy at Bel-Air Country Club and later became the 3rd person to ever go from a caddy to a member. Having grown up without my father around, caddying not only provided me with myriad mentors but also taught me about various industries, afforded access to internships, and ultimately a number of job opportunities. With so many doors open to me thanks to caddying, I went to work for a real estate executive, who was my main loop, after graduating from USC. Shortly thereafter, I started a tech company and was able to join Bel-Air at 29 years old. Due to the great fortune of belonging to such a special club, I have gotten to play many of the best courses in the country and met many people who also caddied. The fact that many immensely successful people grew up working as caddies is really the worst kept secret in golf, but no one has maximized its potential. I’d started working on the concept of CCO over a decade ago and tried to get some golf blogs to run with it, but none of them really got it because they hadn’t caddied. When Kobe Bryant died, I was inspired to just do it myself, and here we are. Approaching it like a startup, I’ve built the foundation. As it naturally evolved into a podcast in order reach a broader audience, we’re now establishing strategic partnerships to take the next big leap on production and distribution. While many golf podcasts have surfaced along with the sport’s newfound popularity, very few of them have anything to say and even fewer can truly scale. COO can excel on both fronts.

Kai, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I have always been fascinated with companies. To me, they are puzzles that can never be completely solved, constantly navigating elements, like cultural evolution, capital allocation, and creative destruction. I’m the son of a failed entrepreneur that led to our family’s bankruptcy and also my becoming the patriarch around 10 years old. I earned a scholarship to attend Cate School as a William New, Jr. Scholar. I earned a merit scholarship to attend USC as a Presidential Scholar, where I studied business administration and the business of the entertainment industry. And through the years, I’ve been published in Inc., Entrepreneur, and HuffPost, spoken at a number of industry conferences, like SXSW, and been quoted by publications, like the Associated Press, US News & World Report, and The Los Angeles Times.

After college, I co-founded a software company in what’s become the sportstech industry; it later became one of the later-stage companies in the first Dodgers Accelerator and has continued to thrive. Like a lot of founders, I naturally began to advise and then invest in startups but found that I didn’t love it when founders would take your money but ignore your battle-proven advice.

I later became the chief innovation officer of a mid-sized company and helped it find growth avenues internally and externally, including corporate venture capital. That led to becoming the entrepreneur-in-residence of an accelerator and a good bit of international business dealings, helping build startups in Norway, Ireland, Singapore, and Kona, Hawaii. I’ve also advised select corporations and family offices on venture investments, helping source, vet, and structure deals that add unique value to their existing assets.

During COVID, I wrote my first book, which helps startup founders improve their marketing efforts, provided that they have a good product. It’s called Marketing Architecture: How to Attract Customers, Hires, and Investors for Any Company Under 50 Employees.

At the same time that I started Caddyshack to Corner Office, I was also the co-president and chief marketing officer of a Nasdaq-listed microcap, focused on decarbonizing existing office buildings. Especially now that I’m a parent, I remain committed to aiding innovation that will combat climate change, but my day job is in private equity, working as a general partner for a unique firm called Mauloa.

How do you keep your team’s morale high?

Culture is everything, even when you’re small a small team. Great cultures are basically cults. You must hire and fire by a standard, ideally surrounding yourself with people are both a cultural fit and also far more talented than you are in as many ways as possible. I messed this up multiple times earlier on in my career, but here is my favorite quote on the topic from Lou Gerstner, Jr.

“Until I came to IBM, I probably would have told you that culture was just one among several important elements in any organization’s makeup and success — along with vision, strategy, marketing, financials, and the like… I came to see, in my time at IBM, that culture isn’t just one aspect of the game, it is the game. In the end, an organization is nothing more than the collective capacity of its people to create value.”

3 Best Books on Corporate Culture: https://www.kaizenreserve.com/book-recs/3-best-books-on-corporate-culture

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

Many, I’m an avid reader but only became one as a first-time founder. Since the business can’t improve until its leaders do, they must be learning continuously, and one of the best ways to do that is by reading books about how others have overcome similar obstacles. In addition to having written a book, I try to share my best book recommendations, including this one that I wrote for Inc. years ago: 6 Books Entrepreneurs Should Read Every Year. https://www.inc.com/kai-sato/6-books-entrepreneurs-should-read-every-year.html

Contact Info:

• Website: https://www.caddyshacktocorneroffice.com/
• Instagram: @caddy2corner
• Linkedin: https://www.linkedin.com/company/caddy2corner/?viewAsMember=true
• Youtube: @caddyshacktocorneroffice